Non-Oxygenated Sesquiterpenes in the Essential Oil of Copaifera langsdorffii Desf. Increase during the Day in the Dry Season
Identifieur interne : 000375 ( Pmc/Corpus ); précédent : 000374; suivant : 000376Non-Oxygenated Sesquiterpenes in the Essential Oil of Copaifera langsdorffii Desf. Increase during the Day in the Dry Season
Auteurs : Luiz Fernando Rolim De Almeida ; Roberto De Oliveira Portella ; Jennifer Bufalo ; Márcia Ortiz Mayo Marques ; Roselaine Facanali ; Fernando FreiSource :
- PLoS ONE [ 1932-6203 ] ; 2016.
Abstract
The present study aimed to evaluate the effect of seasonal and diurnal events on the chemical profile of the essential oil obtained from the leaves of
Url:
DOI: 10.1371/journal.pone.0149332
PubMed: 26886431
PubMed Central: 4757570
Links to Exploration step
PMC:4757570Le document en format XML
<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Non-Oxygenated Sesquiterpenes in the Essential Oil of <italic>Copaifera langsdorffii</italic> Desf. Increase during the Day in the Dry Season</title><author><name sortKey="De Almeida, Luiz Fernando Rolim" sort="De Almeida, Luiz Fernando Rolim" uniqKey="De Almeida L" first="Luiz Fernando Rolim" last="De Almeida">Luiz Fernando Rolim De Almeida</name><affiliation><nlm:aff id="aff001"><addr-line>Department of Botany, Institute of Biosciences of Botucatu, Univ. Estadual Paulista, (UNESP), 18618–970, P.O. Box: 510, Botucatu, Sao Paulo, Brazil</addr-line></nlm:aff></affiliation></author><author><name sortKey="Portella, Roberto De Oliveira" sort="Portella, Roberto De Oliveira" uniqKey="Portella R" first="Roberto De Oliveira" last="Portella">Roberto De Oliveira Portella</name><affiliation><nlm:aff id="aff001"><addr-line>Department of Botany, Institute of Biosciences of Botucatu, Univ. Estadual Paulista, (UNESP), 18618–970, P.O. Box: 510, Botucatu, Sao Paulo, Brazil</addr-line></nlm:aff></affiliation></author><author><name sortKey="Bufalo, Jennifer" sort="Bufalo, Jennifer" uniqKey="Bufalo J" first="Jennifer" last="Bufalo">Jennifer Bufalo</name><affiliation><nlm:aff id="aff001"><addr-line>Department of Botany, Institute of Biosciences of Botucatu, Univ. Estadual Paulista, (UNESP), 18618–970, P.O. Box: 510, Botucatu, Sao Paulo, Brazil</addr-line></nlm:aff></affiliation></author><author><name sortKey="Marques, Marcia Ortiz Mayo" sort="Marques, Marcia Ortiz Mayo" uniqKey="Marques M" first="Márcia Ortiz Mayo" last="Marques">Márcia Ortiz Mayo Marques</name><affiliation><nlm:aff id="aff002"><addr-line>Agronomic Institute, IAC, 13001–970, P.O. Box: 28, Campinas, Sao Paulo, Brazil</addr-line></nlm:aff></affiliation></author><author><name sortKey="Facanali, Roselaine" sort="Facanali, Roselaine" uniqKey="Facanali R" first="Roselaine" last="Facanali">Roselaine Facanali</name><affiliation><nlm:aff id="aff002"><addr-line>Agronomic Institute, IAC, 13001–970, P.O. Box: 28, Campinas, Sao Paulo, Brazil</addr-line></nlm:aff></affiliation></author><author><name sortKey="Frei, Fernando" sort="Frei, Fernando" uniqKey="Frei F" first="Fernando" last="Frei">Fernando Frei</name><affiliation><nlm:aff id="aff003"><addr-line>Department of Biological Sciences, Univ. Estadual Paulista (UNESP), 19800–000, Assis, Sao Paulo, Brazil</addr-line></nlm:aff></affiliation></author></titleStmt><publicationStmt><idno type="wicri:source">PMC</idno><idno type="pmid">26886431</idno><idno type="pmc">4757570</idno><idno type="url">http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4757570</idno><idno type="RBID">PMC:4757570</idno><idno type="doi">10.1371/journal.pone.0149332</idno><date when="2016">2016</date><idno type="wicri:Area/Pmc/Corpus">000375</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en" level="a" type="main">Non-Oxygenated Sesquiterpenes in the Essential Oil of <italic>Copaifera langsdorffii</italic> Desf. Increase during the Day in the Dry Season</title><author><name sortKey="De Almeida, Luiz Fernando Rolim" sort="De Almeida, Luiz Fernando Rolim" uniqKey="De Almeida L" first="Luiz Fernando Rolim" last="De Almeida">Luiz Fernando Rolim De Almeida</name><affiliation><nlm:aff id="aff001"><addr-line>Department of Botany, Institute of Biosciences of Botucatu, Univ. Estadual Paulista, (UNESP), 18618–970, P.O. Box: 510, Botucatu, Sao Paulo, Brazil</addr-line></nlm:aff></affiliation></author><author><name sortKey="Portella, Roberto De Oliveira" sort="Portella, Roberto De Oliveira" uniqKey="Portella R" first="Roberto De Oliveira" last="Portella">Roberto De Oliveira Portella</name><affiliation><nlm:aff id="aff001"><addr-line>Department of Botany, Institute of Biosciences of Botucatu, Univ. Estadual Paulista, (UNESP), 18618–970, P.O. Box: 510, Botucatu, Sao Paulo, Brazil</addr-line></nlm:aff></affiliation></author><author><name sortKey="Bufalo, Jennifer" sort="Bufalo, Jennifer" uniqKey="Bufalo J" first="Jennifer" last="Bufalo">Jennifer Bufalo</name><affiliation><nlm:aff id="aff001"><addr-line>Department of Botany, Institute of Biosciences of Botucatu, Univ. Estadual Paulista, (UNESP), 18618–970, P.O. Box: 510, Botucatu, Sao Paulo, Brazil</addr-line></nlm:aff></affiliation></author><author><name sortKey="Marques, Marcia Ortiz Mayo" sort="Marques, Marcia Ortiz Mayo" uniqKey="Marques M" first="Márcia Ortiz Mayo" last="Marques">Márcia Ortiz Mayo Marques</name><affiliation><nlm:aff id="aff002"><addr-line>Agronomic Institute, IAC, 13001–970, P.O. Box: 28, Campinas, Sao Paulo, Brazil</addr-line></nlm:aff></affiliation></author><author><name sortKey="Facanali, Roselaine" sort="Facanali, Roselaine" uniqKey="Facanali R" first="Roselaine" last="Facanali">Roselaine Facanali</name><affiliation><nlm:aff id="aff002"><addr-line>Agronomic Institute, IAC, 13001–970, P.O. Box: 28, Campinas, Sao Paulo, Brazil</addr-line></nlm:aff></affiliation></author><author><name sortKey="Frei, Fernando" sort="Frei, Fernando" uniqKey="Frei F" first="Fernando" last="Frei">Fernando Frei</name><affiliation><nlm:aff id="aff003"><addr-line>Department of Biological Sciences, Univ. Estadual Paulista (UNESP), 19800–000, Assis, Sao Paulo, Brazil</addr-line></nlm:aff></affiliation></author></analytic><series><title level="j">PLoS ONE</title><idno type="eISSN">1932-6203</idno><imprint><date when="2016">2016</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en"><p>The present study aimed to evaluate the effect of seasonal and diurnal events on the chemical profile of the essential oil obtained from the leaves of <italic>Copaifera langsdorffii</italic> Desf. This study was performed in a Brazilian savanna named Cerrado. We identified the best harvesting period for obtaining the highest amount of compounds used for commercial and industrial purposes. The chemical profile of the essential oils was evaluated by GC-FID and GC-MS, and the results were assessed through multivariate analyses. The data showed that the time of day and seasonal variations affect the quality of the essential oil obtained. Leaves harvested at the end of the day (5:00 pm) in the dry season resulted in richer essential oils with higher amounts of non-oxygenated sesquiterpenes. To the best of our knowledge, environmental conditions induce metabolic responses in the leaves of <italic>C</italic>. <italic>langsdorffii</italic>, which changes the patterns of sesquiterpene production. Therefore, these factors need to be considered to obtain better concentrations of bioactive compounds for pharmacological studies.</p></div></front><back><div1 type="bibliography"><listBibl><biblStruct><analytic><author><name sortKey="Figueiredo, Ac" uniqKey="Figueiredo A">AC Figueiredo</name></author><author><name sortKey="Barroso, Jg" uniqKey="Barroso J">JG Barroso</name></author><author><name sortKey="Pedro, Lg" uniqKey="Pedro L">LG Pedro</name></author><author><name sortKey="Scheffer, Jjc" uniqKey="Scheffer J">JJC Scheffer</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Lincoln, De" uniqKey="Lincoln D">DE Lincoln</name></author><author><name sortKey="Langenheim, Jh" uniqKey="Langenheim J">JH Langenheim</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Mcgimpsey, Ja" uniqKey="Mcgimpsey J">JA McGimpsey</name></author><author><name sortKey="Douglas, Mh" uniqKey="Douglas M">MH Douglas</name></author><author><name sortKey="Van Klink, Jw" uniqKey="Van Klink J">JW Van Klink</name></author><author><name sortKey="Beauregard, Da" uniqKey="Beauregard D">DA Beauregard</name></author><author><name sortKey="Perry, Nb" uniqKey="Perry N">NB Perry</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Von Rudloff, E" uniqKey="Von Rudloff E">E von Rudloff</name></author><author><name sortKey="Underhill, Ew" uniqKey="Underhill E">EW Underhill</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Voirin, B" uniqKey="Voirin B">B Voirin</name></author><author><name sortKey="Brun, N" uniqKey="Brun N">N Brun</name></author><author><name sortKey="Bayet, C" uniqKey="Bayet C">C Bayet</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Klink, Ca" uniqKey="Klink C">CA Klink</name></author><author><name sortKey="Machado, Rb" uniqKey="Machado R">RB Machado</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Wang, H" uniqKey="Wang H">H Wang</name></author><author><name sortKey="Liu, Y" uniqKey="Liu Y">Y Liu</name></author><author><name sortKey="Wei, S" uniqKey="Wei S">S Wei</name></author><author><name sortKey="Yan, Z" uniqKey="Yan Z">Z Yan</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Coutinho, Lm" uniqKey="Coutinho L">LM Coutinho</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Almeida, Lfr" uniqKey="Almeida L">LFR Almeida</name></author><author><name sortKey="Portella, Ro" uniqKey="Portella R">RO Portella</name></author><author><name sortKey="Facanali, R" uniqKey="Facanali R">R Facanali</name></author><author><name sortKey="Marques, Mom" uniqKey="Marques M">MOM Marques</name></author><author><name sortKey="Frei, F" uniqKey="Frei F">F Frei</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Bakkali, F" uniqKey="Bakkali F">F Bakkali</name></author><author><name sortKey="Averbeck, S" uniqKey="Averbeck S">S Averbeck</name></author><author><name sortKey="Averbeck, D" uniqKey="Averbeck D">D Averbeck</name></author><author><name sortKey="Idaomar, M" uniqKey="Idaomar M">M Idaomar</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Michel, Cg" uniqKey="Michel C">CG Michel</name></author><author><name sortKey="Nesseem, Di" uniqKey="Nesseem D">DI Nesseem</name></author><author><name sortKey="Ismail, Mf" uniqKey="Ismail M">MF Ismail</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Hussain, Ai" uniqKey="Hussain A">AI Hussain</name></author><author><name sortKey="Anwar, F" uniqKey="Anwar F">F Anwar</name></author><author><name sortKey="Sherazi, Sth" uniqKey="Sherazi S">STH Sherazi</name></author><author><name sortKey="Przybylski, R" uniqKey="Przybylski R">R Przybylski</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Rodilla, Jm" uniqKey="Rodilla J">JM Rodilla</name></author><author><name sortKey="Tinoco, Mt" uniqKey="Tinoco M">MT Tinoco</name></author><author><name sortKey="Morais, Jc" uniqKey="Morais J">JC Morais</name></author><author><name sortKey="Gimenez, C" uniqKey="Gimenez C">C Gimenez</name></author><author><name sortKey="Cebrera, R" uniqKey="Cebrera R">R Cebrera</name></author><author><name sortKey="Martin Benito, D" uniqKey="Martin Benito D">D Martín-Benito</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Sartor, T" uniqKey="Sartor T">T Sartor</name></author><author><name sortKey="Xavier, Vb" uniqKey="Xavier V">VB Xavier</name></author><author><name sortKey="Falcao, Ma" uniqKey="Falcao M">MA Falcão</name></author><author><name sortKey="Mondin, Ca" uniqKey="Mondin C">CA Mondin</name></author><author><name sortKey="Dos Santos, Ma" uniqKey="Dos Santos M">MA dos Santos</name></author><author><name sortKey="Cassel, E" uniqKey="Cassel E">E Cassel</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Paolini, J" uniqKey="Paolini J">J Paolini</name></author><author><name sortKey="Barboni, T" uniqKey="Barboni T">T Barboni</name></author><author><name sortKey="Desjobert, Jm" uniqKey="Desjobert J">JM Desjobert</name></author><author><name sortKey="Djabou, N" uniqKey="Djabou N">N Djabou</name></author><author><name sortKey="Muselli, A" uniqKey="Muselli A">A Muselli</name></author><author><name sortKey="Costa, J" uniqKey="Costa J">J Costa</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Telci, I" uniqKey="Telci I">I Telci</name></author><author><name sortKey="Kacar, O" uniqKey="Kacar O">O Kacar</name></author><author><name sortKey="Bayram, E" uniqKey="Bayram E">E Bayram</name></author><author><name sortKey="Arabaci, O" uniqKey="Arabaci O">O Arabaci</name></author><author><name sortKey="Demirta, I" uniqKey="Demirta I">I Demirtaş</name></author><author><name sortKey="Yilmaz, G" uniqKey="Yilmaz G">G Yilmaz</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Kumar, R" uniqKey="Kumar R">R Kumar</name></author><author><name sortKey="Sharma, S" uniqKey="Sharma S">S Sharma</name></author><author><name sortKey="Sood, S" uniqKey="Sood S">S Sood</name></author><author><name sortKey="Agnihotri, Vk" uniqKey="Agnihotri V">VK Agnihotri</name></author><author><name sortKey="Singh, B" uniqKey="Singh B">B Singh</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Veiga Junior, Vf" uniqKey="Veiga Junior V">VF Veiga Junior</name></author><author><name sortKey="Pinto, Ac" uniqKey="Pinto A">AC Pinto</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Freitas, Cv" uniqKey="Freitas C">CV Freitas</name></author><author><name sortKey="Oliveira, Pe" uniqKey="Oliveira P">PE Oliveira</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Nascimento, Me" uniqKey="Nascimento M">ME Nascimento</name></author><author><name sortKey="Zoghbi, Mgb" uniqKey="Zoghbi M">MGB Zoghbi</name></author><author><name sortKey="Pinto, Jebp" uniqKey="Pinto J">JEBP Pinto</name></author><author><name sortKey="Bertolucci, Skv" uniqKey="Bertolucci S">SKV Bertolucci</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Leandro, Lm" uniqKey="Leandro L">LM Leandro</name></author><author><name sortKey="Vargas, Fs" uniqKey="Vargas F">FS Vargas</name></author><author><name sortKey="Barbosa, Pcs" uniqKey="Barbosa P">PCS Barbosa</name></author><author><name sortKey="Neves, Jko" uniqKey="Neves J">JKO Neves</name></author><author><name sortKey="Silva, Ja" uniqKey="Silva J">JA Silva</name></author><author><name sortKey="Veiga Junior, Vf" uniqKey="Veiga Junior V">VF Veiga-Junior</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Gelmini, F" uniqKey="Gelmini F">F Gelmini</name></author><author><name sortKey="Beretta, G" uniqKey="Beretta G">G Beretta</name></author><author><name sortKey="Anselmi, C" uniqKey="Anselmi C">C Anselmi</name></author><author><name sortKey="Centini, M" uniqKey="Centini M">M Centini</name></author><author><name sortKey="Magni, P" uniqKey="Magni P">P Magni</name></author><author><name sortKey="Ruscica, M" uniqKey="Ruscica M">M Ruscica</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Ribeiro, Da" uniqKey="Ribeiro D">DA Ribeiro</name></author><author><name sortKey="Oliveira, Lgs" uniqKey="Oliveira L">LGS Oliveira</name></author><author><name sortKey="Macedo, Dg" uniqKey="Macedo D">DG Macêdo</name></author><author><name sortKey="Menezes, Ira" uniqKey="Menezes I">IRA Menezes</name></author><author><name sortKey="Costa, Jgm" uniqKey="Costa J">JGM Costa</name></author><author><name sortKey="Silva, Map" uniqKey="Silva M">MAP Silva</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Oliveira, Ps" uniqKey="Oliveira P">PS Oliveira</name></author><author><name sortKey="Marquis, Rj" uniqKey="Marquis R">RJ Marquis</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Ribeiro, Jf" uniqKey="Ribeiro J">JF Ribeiro</name></author><author><name sortKey="Waler, Bmt" uniqKey="Waler B">BMT Waler</name></author><author><name sortKey="Sano, S M" uniqKey="Sano S">S.M. Sano</name></author><author><name sortKey="Almeida, S P" uniqKey="Almeida S">S.P. Almeida</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Silva, Ef" uniqKey="Silva E">EF Silva</name></author><author><name sortKey="Santos, Trr" uniqKey="Santos T">TRR Santos</name></author><author><name sortKey="Fernandes Bulhao, C" uniqKey="Fernandes Bulhao C">C Fernandes-Bulhão</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Mclafferty, Fw" uniqKey="Mclafferty F">FW McLafferty</name></author><author><name sortKey="Stauffer, D" uniqKey="Stauffer D">D Stauffer</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Adams, Rp" uniqKey="Adams R">RP Adams</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Van Den Dool, H" uniqKey="Van Den Dool H">H Van Den Dool</name></author><author><name sortKey="Kratz, Dj" uniqKey="Kratz D">DJ Kratz</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Gramosa, Nv" uniqKey="Gramosa N">NV Gramosa</name></author><author><name sortKey="Silveira, Er" uniqKey="Silveira E">ER Silveira</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Chen, F" uniqKey="Chen F">F Chen</name></author><author><name sortKey="Al Ahmad, H" uniqKey="Al Ahmad H">H Al-Ahmad</name></author><author><name sortKey="Joyce, B" uniqKey="Joyce B">B Joyce</name></author><author><name sortKey="Zhao, N" uniqKey="Zhao N">N Zhao</name></author><author><name sortKey="Kollner, Tg" uniqKey="Kollner T">TG Köllner</name></author><author><name sortKey="Degenhardt, J" uniqKey="Degenhardt J">J Degenhardt</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Cascon, V" uniqKey="Cascon V">V Cascon</name></author><author><name sortKey="Gilbert, B" uniqKey="Gilbert B">B Gilbert</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Veiga, Vf" uniqKey="Veiga V">VF Veiga</name></author><author><name sortKey="Pinto, Ac" uniqKey="Pinto A">AC Pinto</name></author><author><name sortKey="Lima, Hc" uniqKey="Lima H">HC Lima</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Zoghbi, Mgb" uniqKey="Zoghbi M">MGB Zoghbi</name></author><author><name sortKey="Martins Da Silva, Rcv" uniqKey="Martins Da Silva R">RCV Martins-da-Silva</name></author><author><name sortKey="Trigo, Jr" uniqKey="Trigo J">JR Trigo</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Sangwan, Ns" uniqKey="Sangwan N">NS Sangwan</name></author><author><name sortKey="Farooqi, Aha" uniqKey="Farooqi A">AHA Farooqi</name></author><author><name sortKey="Shabih, F" uniqKey="Shabih F">F Shabih</name></author><author><name sortKey="Sangwan, Rs" uniqKey="Sangwan R">RS Sangwan</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Gawronska, K" uniqKey="Gawronska K">K Gawronska</name></author><author><name sortKey="Romanowska, E" uniqKey="Romanowska E">E Romanowska</name></author><author><name sortKey="Miszalski, Z" uniqKey="Miszalski Z">Z Miszalski</name></author><author><name sortKey="Niewiadomska, E" uniqKey="Niewiadomska E">E Niewiadomska</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Rodrigues, Tm" uniqKey="Rodrigues T">TM Rodrigues</name></author><author><name sortKey="Buarque, Pfsm" uniqKey="Buarque P">PFSM Buarque</name></author><author><name sortKey="Coneglian, Ag" uniqKey="Coneglian A">AG Coneglian</name></author><author><name sortKey="Reis, Dc" uniqKey="Reis D">DC Reis</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Vidovi, M" uniqKey="Vidovi M">M Vidović</name></author><author><name sortKey="Morina, F" uniqKey="Morina F">F Morina</name></author><author><name sortKey="Mili, S" uniqKey="Mili S">S Milić</name></author><author><name sortKey="Albert, A" uniqKey="Albert A">A Albert</name></author><author><name sortKey="Zechmann, B" uniqKey="Zechmann B">B Zechmann</name></author><author><name sortKey="Tosti, T" uniqKey="Tosti T">T Tosti</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Helmig, D" uniqKey="Helmig D">D Helmig</name></author><author><name sortKey="Ortega, J" uniqKey="Ortega J">J Ortega</name></author><author><name sortKey="Guenther, A" uniqKey="Guenther A">A Guenther</name></author><author><name sortKey="Herrick, Jd" uniqKey="Herrick J">JD Herrick</name></author><author><name sortKey="Geron, C" uniqKey="Geron C">C Geron</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Duhl, Tr" uniqKey="Duhl T">TR Duhl</name></author><author><name sortKey="Helmig, D" uniqKey="Helmig D">D Helmig</name></author><author><name sortKey="Guenther, A" uniqKey="Guenther A">A Guenther</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Ribeiro, Af" uniqKey="Ribeiro A">AF Ribeiro</name></author><author><name sortKey="Andrade, Eha" uniqKey="Andrade E">EHA Andrade</name></author><author><name sortKey="Salimena, Frg" uniqKey="Salimena F">FRG Salimena</name></author><author><name sortKey="Maia, Jgs" uniqKey="Maia J">JGS Maia</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Asghari, G" uniqKey="Asghari G">G Asghari</name></author><author><name sortKey="Gholamali, H" uniqKey="Gholamali H">H Gholamali</name></author><author><name sortKey="Mahmoudi, Z" uniqKey="Mahmoudi Z">Z Mahmoudi</name></author><author><name sortKey="Asghari, M" uniqKey="Asghari M">M Asghari</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Christensen, Cs" uniqKey="Christensen C">CS Christensen</name></author><author><name sortKey="Hummelsh J, P" uniqKey="Hummelsh J P">P Hummelshøj</name></author><author><name sortKey="Jensen, No" uniqKey="Jensen N">NO Jensen</name></author><author><name sortKey="Larsen, B" uniqKey="Larsen B">B Larsen</name></author><author><name sortKey="Lohse, C" uniqKey="Lohse C">C Lohse</name></author><author><name sortKey="Pilegaard, K" uniqKey="Pilegaard K">K Pilegaard</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Fuentes, Jd" uniqKey="Fuentes J">JD Fuentes</name></author><author><name sortKey="Wang, D" uniqKey="Wang D">D Wang</name></author><author><name sortKey="Neumann, Hh" uniqKey="Neumann H">HH Neumann</name></author><author><name sortKey="Gillespie, Tj" uniqKey="Gillespie T">TJ Gillespie</name></author><author><name sortKey="Den Hartog, G" uniqKey="Den Hartog G">G Den Hartog</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Vallat, A" uniqKey="Vallat A">A Vallat</name></author><author><name sortKey="Gu, H" uniqKey="Gu H">H Gu</name></author><author><name sortKey="Dorn, S" uniqKey="Dorn S">S Dorn</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Angelopoulou, D" uniqKey="Angelopoulou D">D Angelopoulou</name></author><author><name sortKey="Demetzo, C" uniqKey="Demetzo C">C Demetzo</name></author><author><name sortKey="Perdetzoglou, D" uniqKey="Perdetzoglou D">D Perdetzoglou</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Toncer, O" uniqKey="Toncer O">O Toncer</name></author><author><name sortKey="Karaman, S" uniqKey="Karaman S">S Karaman</name></author><author><name sortKey="Kizil, S" uniqKey="Kizil S">S Kizil</name></author><author><name sortKey="Diraz, E" uniqKey="Diraz E">E Diraz</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Del Vechio Vieira, G" uniqKey="Del Vechio Vieira G">G Del-Vechio-Vieira</name></author><author><name sortKey="Sousa, Ov" uniqKey="Sousa O">OV Sousa</name></author><author><name sortKey="Yamamoto, Ch" uniqKey="Yamamoto C">CH Yamamoto</name></author><author><name sortKey="Kaplan, Mac" uniqKey="Kaplan M">MAC Kaplan</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Nagappan, T" uniqKey="Nagappan T">T Nagappan</name></author><author><name sortKey="Ramasamy, P" uniqKey="Ramasamy P">P Ramasamy</name></author><author><name sortKey="Wahid, Mea" uniqKey="Wahid M">MEA Wahid</name></author><author><name sortKey="Segaran, Tc" uniqKey="Segaran T">TC Segaran</name></author><author><name sortKey="Vairappan, Cs" uniqKey="Vairappan C">CS Vairappan</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Kobaisy, M" uniqKey="Kobaisy M">M Kobaisy</name></author><author><name sortKey="Tellez, Mr" uniqKey="Tellez M">MR Tellez</name></author><author><name sortKey="Dayan, Fe" uniqKey="Dayan F">FE Dayan</name></author><author><name sortKey="Duke, So" uniqKey="Duke S">SO Duke</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Rigano, D" uniqKey="Rigano D">D Rigano</name></author><author><name sortKey="Arnold, Na" uniqKey="Arnold N">NA Arnold</name></author><author><name sortKey="Conforti, F" uniqKey="Conforti F">F Conforti</name></author><author><name sortKey="Menichini, F" uniqKey="Menichini F">F Menichini</name></author><author><name sortKey="Formisano, C" uniqKey="Formisano C">C Formisano</name></author><author><name sortKey="Piozzi, F" uniqKey="Piozzi F">F Piozzi</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Kucukbay, Fz" uniqKey="Kucukbay F">FZ Küçükbay</name></author><author><name sortKey="Kuyumcu, E" uniqKey="Kuyumcu E">E Kuyumcu</name></author><author><name sortKey="Bilenler, T" uniqKey="Bilenler T">T Bilenler</name></author><author><name sortKey="Yildiz, B" uniqKey="Yildiz B">B Yildiz</name></author></analytic></biblStruct></listBibl></div1></back></TEI><pmc article-type="research-article"><pmc-dir>properties open_access</pmc-dir>
<front><journal-meta><journal-id journal-id-type="nlm-ta">PLoS One</journal-id><journal-id journal-id-type="iso-abbrev">PLoS ONE</journal-id><journal-id journal-id-type="publisher-id">plos</journal-id><journal-id journal-id-type="pmc">plosone</journal-id><journal-title-group><journal-title>PLoS ONE</journal-title></journal-title-group><issn pub-type="epub">1932-6203</issn><publisher><publisher-name>Public Library of Science</publisher-name><publisher-loc>San Francisco, CA USA</publisher-loc></publisher></journal-meta><article-meta><article-id pub-id-type="pmid">26886431</article-id><article-id pub-id-type="pmc">4757570</article-id><article-id pub-id-type="doi">10.1371/journal.pone.0149332</article-id><article-id pub-id-type="publisher-id">PONE-D-15-45404</article-id><article-categories><subj-group subj-group-type="heading"><subject>Research Article</subject></subj-group><subj-group subj-group-type="Discipline-v3"><subject>Biology and Life Sciences</subject><subj-group><subject>Biochemistry</subject><subj-group><subject>Lipids</subject><subj-group><subject>Oils</subject></subj-group></subj-group></subj-group></subj-group><subj-group subj-group-type="Discipline-v3"><subject>Earth Sciences</subject><subj-group><subject>Seasons</subject></subj-group></subj-group><subj-group subj-group-type="Discipline-v3"><subject>Biology and Life Sciences</subject><subj-group><subject>Plant Science</subject><subj-group><subject>Plant Anatomy</subject><subj-group><subject>Leaves</subject></subj-group></subj-group></subj-group></subj-group><subj-group subj-group-type="Discipline-v3"><subject>Earth Sciences</subject><subj-group><subject>Seasons</subject><subj-group><subject>Seasonal Variations</subject></subj-group></subj-group></subj-group><subj-group subj-group-type="Discipline-v3"><subject>Biology and Life Sciences</subject><subj-group><subject>Behavior</subject><subj-group><subject>Diurnal Variations</subject></subj-group></subj-group></subj-group><subj-group subj-group-type="Discipline-v3"><subject>Physical Sciences</subject><subj-group><subject>Chemistry</subject><subj-group><subject>Chemical Compounds</subject><subj-group><subject>Organic Compounds</subject><subj-group><subject>Terpenes</subject></subj-group></subj-group></subj-group></subj-group></subj-group><subj-group subj-group-type="Discipline-v3"><subject>Physical Sciences</subject><subj-group><subject>Chemistry</subject><subj-group><subject>Organic Chemistry</subject><subj-group><subject>Organic Compounds</subject><subj-group><subject>Terpenes</subject></subj-group></subj-group></subj-group></subj-group></subj-group><subj-group subj-group-type="Discipline-v3"><subject>Research and Analysis Methods</subject><subj-group><subject>Mathematical and Statistical Techniques</subject><subj-group><subject>Statistical Methods</subject><subj-group><subject>Multivariate Analysis</subject><subj-group><subject>Principal Component Analysis</subject></subj-group></subj-group></subj-group></subj-group></subj-group><subj-group subj-group-type="Discipline-v3"><subject>Physical Sciences</subject><subj-group><subject>Mathematics</subject><subj-group><subject>Statistics (Mathematics)</subject><subj-group><subject>Statistical Methods</subject><subj-group><subject>Multivariate Analysis</subject><subj-group><subject>Principal Component Analysis</subject></subj-group></subj-group></subj-group></subj-group></subj-group></subj-group><subj-group subj-group-type="Discipline-v3"><subject>Earth Sciences</subject><subj-group><subject>Atmospheric Science</subject><subj-group><subject>Meteorology</subject><subj-group><subject>Rain</subject></subj-group></subj-group></subj-group></subj-group></article-categories><title-group><article-title>Non-Oxygenated Sesquiterpenes in the Essential Oil of <italic>Copaifera langsdorffii</italic> Desf. Increase during the Day in the Dry Season</article-title><alt-title alt-title-type="running-head">Non-Oxygenated Sesquiterpenes in <italic>Copaifera langsdorffii</italic></alt-title></title-group><contrib-group><contrib contrib-type="author"><name><surname>de Almeida</surname><given-names>Luiz Fernando Rolim</given-names></name><xref ref-type="aff" rid="aff001"><sup>1</sup></xref></contrib><contrib contrib-type="author"><name><surname>Portella</surname><given-names>Roberto de Oliveira</given-names></name><xref ref-type="aff" rid="aff001"><sup>1</sup></xref></contrib><contrib contrib-type="author"><name><surname>Bufalo</surname><given-names>Jennifer</given-names></name><xref ref-type="aff" rid="aff001"><sup>1</sup></xref><xref ref-type="corresp" rid="cor001">*</xref></contrib><contrib contrib-type="author"><name><surname>Marques</surname><given-names>Márcia Ortiz Mayo</given-names></name><xref ref-type="aff" rid="aff002"><sup>2</sup></xref></contrib><contrib contrib-type="author"><name><surname>Facanali</surname><given-names>Roselaine</given-names></name><xref ref-type="aff" rid="aff002"><sup>2</sup></xref></contrib><contrib contrib-type="author"><name><surname>Frei</surname><given-names>Fernando</given-names></name><xref ref-type="aff" rid="aff003"><sup>3</sup></xref></contrib></contrib-group><aff id="aff001"><label>1</label><addr-line>Department of Botany, Institute of Biosciences of Botucatu, Univ. Estadual Paulista, (UNESP), 18618–970, P.O. Box: 510, Botucatu, Sao Paulo, Brazil</addr-line></aff><aff id="aff002"><label>2</label><addr-line>Agronomic Institute, IAC, 13001–970, P.O. Box: 28, Campinas, Sao Paulo, Brazil</addr-line></aff><aff id="aff003"><label>3</label><addr-line>Department of Biological Sciences, Univ. Estadual Paulista (UNESP), 19800–000, Assis, Sao Paulo, Brazil</addr-line></aff><contrib-group><contrib contrib-type="editor"><name><surname>Chang</surname><given-names>Ing-Feng</given-names></name><role>Editor</role><xref ref-type="aff" rid="edit1"></xref></contrib></contrib-group><aff id="edit1"><addr-line>National Taiwan University, TAIWAN</addr-line></aff><author-notes><fn fn-type="conflict" id="coi001"><p><bold>Competing Interests: </bold>The authors have declared that no competing interests exist.</p></fn><fn fn-type="con" id="contrib001"><p>Conceived and designed the experiments: LFRA ROP. Performed the experiments: LFRA ROP. Analyzed the data: LFRA ROP JB MOMM RF FF. Contributed reagents/materials/analysis tools: LFRA MOMM FF. Wrote the paper: LFRA ROP JB MOMM RF FF.</p></fn><corresp id="cor001">* E-mail: <email>jenniferbufalo@yahoo.com.br</email></corresp></author-notes><pub-date pub-type="epub"><day>17</day><month>2</month><year>2016</year></pub-date><pub-date pub-type="collection"><year>2016</year></pub-date><volume>11</volume><issue>2</issue><elocation-id>e0149332</elocation-id><history><date date-type="received"><day>19</day><month>10</month><year>2015</year></date><date date-type="accepted"><day>29</day><month>1</month><year>2016</year></date></history><permissions><copyright-statement>© 2016 de Almeida et al</copyright-statement><copyright-year>2016</copyright-year><copyright-holder>de Almeida et al</copyright-holder><license xlink:href="http://creativecommons.org/licenses/by/4.0/"><license-p>This is an open access article distributed under the terms of the <ext-link ext-link-type="uri" xlink:href="http://creativecommons.org/licenses/by/4.0/">Creative Commons Attribution License</ext-link>, which permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are credited.</license-p></license></permissions><self-uri content-type="pdf" xlink:type="simple" xlink:href="pone.0149332.pdf"></self-uri><abstract><p>The present study aimed to evaluate the effect of seasonal and diurnal events on the chemical profile of the essential oil obtained from the leaves of <italic>Copaifera langsdorffii</italic> Desf. This study was performed in a Brazilian savanna named Cerrado. We identified the best harvesting period for obtaining the highest amount of compounds used for commercial and industrial purposes. The chemical profile of the essential oils was evaluated by GC-FID and GC-MS, and the results were assessed through multivariate analyses. The data showed that the time of day and seasonal variations affect the quality of the essential oil obtained. Leaves harvested at the end of the day (5:00 pm) in the dry season resulted in richer essential oils with higher amounts of non-oxygenated sesquiterpenes. To the best of our knowledge, environmental conditions induce metabolic responses in the leaves of <italic>C</italic>. <italic>langsdorffii</italic>, which changes the patterns of sesquiterpene production. Therefore, these factors need to be considered to obtain better concentrations of bioactive compounds for pharmacological studies.</p></abstract><funding-group><funding-statement>This research was funded by the Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP). Luiz Fernando Rolim de Almeida received financial support process n° 2010/15585-6 and Roberto Oliveira Portela scholarship process n° 2013/07629-1 (<ext-link ext-link-type="uri" xlink:href="http://www.fapesp.br/">http://www.fapesp.br/</ext-link>). The funders had no role in study design, data collection and analysis, decision to publish, or preparation of the manuscript.</funding-statement></funding-group><counts><fig-count count="3"></fig-count><table-count count="1"></table-count><page-count count="12"></page-count></counts><custom-meta-group><custom-meta id="data-availability"><meta-name>Data Availability</meta-name><meta-value>All relevant data are within the paper and its Supporting Information files.</meta-value></custom-meta></custom-meta-group></article-meta><notes><title>Data Availability</title><p>All relevant data are within the paper and its Supporting Information files.</p></notes></front><body><sec sec-type="intro" id="sec001"><title>Introduction</title><p>Understanding the seasonal events that change the quality of plant volatile compounds is essential for pharmacological studies. Generally, essential oil constituents are influenced by genetic factors and environmental conditions [<xref rid="pone.0149332.ref001" ref-type="bibr">1</xref>]. The terpenoid composition of aromatic plants can be affected by the photoperiod, light intensity, temperature and harvesting season or month [<xref rid="pone.0149332.ref002" ref-type="bibr">2</xref>–<xref rid="pone.0149332.ref005" ref-type="bibr">5</xref>].</p><p>The Cerrado biome, a typical savanna-like vegetation in the central region of Brazil, displays seasonal characteristics that promote changes in the water availability and quality and quantity of light [<xref rid="pone.0149332.ref006" ref-type="bibr">6</xref>], which, in turn, result in modifications in the essential oil production and chemical composition of plant products [<xref rid="pone.0149332.ref007" ref-type="bibr">7</xref>]. The Cerrado consists of complex types of vegetation that range from grasslands to woodlands [<xref rid="pone.0149332.ref008" ref-type="bibr">8</xref>]. In addition, this biome is subjected to seasonal events such as the occurrence of dry winters (April to September), which result in changes on the phytochemical profile of essential oils [<xref rid="pone.0149332.ref009" ref-type="bibr">9</xref>] and trigger oscillations on their biosynthesis, yield and composition [<xref rid="pone.0149332.ref010" ref-type="bibr">10</xref>]. Previous studies found a significant impact of the seasonal variation on the essential oil composition of several species such as <italic>Zizyphus spina-christi</italic> (L.) Willd [<xref rid="pone.0149332.ref011" ref-type="bibr">11</xref>], <italic>Ocimum basilicum</italic> L. [<xref rid="pone.0149332.ref012" ref-type="bibr">12</xref>], <italic>Laurus azorica</italic> Franco (Seub.) [<xref rid="pone.0149332.ref013" ref-type="bibr">13</xref>] and <italic>Baccharis dentata</italic> (Vell.) G.M. Barroso [<xref rid="pone.0149332.ref014" ref-type="bibr">14</xref>]. Furthermore, changes in the terpenoid concentration of the essential oils due to diurnal variation have also been observed. A reciprocal regulation between α-cadinol and δ-cadinene occurs in <italic>Calendula arvensis</italic> L. [<xref rid="pone.0149332.ref015" ref-type="bibr">15</xref>], and a lower conversion of mentone to menthol under high temperatures occurred in the essential oils of <italic>Mentha piperita</italic> L. [<xref rid="pone.0149332.ref016" ref-type="bibr">16</xref>]. <italic>Rosa damascena</italic> Mill. flowers modified the essential oil composition during the day, showing an increase of oxides concentrations at 12:00 pm and a decrease during other times of the day [<xref rid="pone.0149332.ref017" ref-type="bibr">17</xref>].</p><p><italic>Copaifera langsdorffii</italic> Desf. (Fabacecae-Ceasalpinoidae), popularly known as copaíba, is a native species of tropical regions of Latin America [<xref rid="pone.0149332.ref018" ref-type="bibr">18</xref>] and is widely distributed in the Brazilian Cerrado and other forests [<xref rid="pone.0149332.ref019" ref-type="bibr">19</xref>]. Specialized metabolites are found in <italic>C</italic>. <italic>langsdorffii</italic> cavities and resiniferous channels, which produce essential oils. The main compounds of the volatile section of the oleoresin are germacrene D, spathulenol and caryophyllene oxide, whereas <italic>ent</italic>-kaurenoids are the major components of the non-volatile section [<xref rid="pone.0149332.ref020" ref-type="bibr">20</xref>]. The oleoresin of <italic>Copaifera</italic> exhibits anti-inflammatory, antimicrobial, larvicidal and antineoplastic pharmacological activities [<xref rid="pone.0149332.ref021" ref-type="bibr">21</xref>]. Moreover, the essential oils of <italic>C</italic>. <italic>langsdorffii</italic> have anti-tumor and healing properties and present gastroprotective activities [<xref rid="pone.0149332.ref018" ref-type="bibr">18</xref>]. Furthermore, the oleoresin of copaíba trees exerts strong antioxidant and anti-inflammatory effects and is composed of several sesquiterpenes and unsaturated diterpene acids [<xref rid="pone.0149332.ref022" ref-type="bibr">22</xref>]. <italic>C</italic>. <italic>langsdorffii</italic> has significant importance in popular traditional medicine because it is widely used in more than 14 categories of body treatments and 55 different health disorders [<xref rid="pone.0149332.ref023" ref-type="bibr">23</xref>]. Regarding the influence of the seasonal and diurnal changes on the essential oil composition, this study provides the first investigation of the qualitative variations in the essential oil composition of <italic>C</italic>. <italic>langsdorffii</italic>. The obtained information will be important for the identification of the optimal chemical profile. Here, we analyzed the seasonal and diurnal variations in the essential oil composition in samples of <italic>C</italic>. <italic>langsdorffii</italic> leaves. Our most significant finding is that there are changes in the levels of major sesquiterpenes.</p></sec><sec sec-type="materials|methods" id="sec002"><title>Materials and Methods</title><sec id="sec003"><title>Plant materials and experimental design</title><p>Leaf samples of three individuals of <italic>C</italic>. <italic>langsdorffii</italic> were collected in 2012 from a semideciduous seasonal forest (SSF; Cerrado physiognomy) in Rubião Júnior, Botucatu, São Paulo State, Brazil (22°53’37.86”S 48°29’22.78”W). A voucher was deposited in the Irina Delanova Gemtchujnicov Herbarium (BOTU) under number 29,274 at the Institute of Biosciences of Botucatu, UNESP. We collected one sample per individual at 6:00 am (early morning) and 5:00 pm (afternoon) at the end of dry season (DS) and wet season (WS). According to the literature [<xref rid="pone.0149332.ref024" ref-type="bibr">24</xref>], the climate of Cerrado in this site shows a dry season (April to September) and a wet season (October to March). Likewise, it presents dry winters and humid summers [<xref rid="pone.0149332.ref025" ref-type="bibr">25</xref>,<xref rid="pone.0149332.ref026" ref-type="bibr">26</xref>]. <italic>C</italic>. <italic>langsdorffii</italic> leaves were harvested packed in paper bags and placed at a drying in a forced-air drier at 35˚C for 72 h.</p><p>To study the influence of these seasonal variations, we considered the dry season from July to October with an average temperature of 20.2˚C and an average rainfall of 52.88 mm; we collected the samples on October 03<sup>rd</sup>. The wet season included the months of January through March with an average temperature of 25.0˚C and an average rainfall of 582.88 mm; we collected the samples on March 27<sup>th</sup>. During the sample collecting day, at early morning (6:00 am), in dry season the light intensity was 55 μmol m<sup>-2</sup>s<sup>-1</sup> and in wet season was 3 μmol m<sup>-2</sup>s<sup>-1</sup>. On the other hand, during afternoon (5:00 pm) the light intensity was 147 μmol m<sup>-2</sup>s<sup>-1</sup> in wet season and 173 μmol m<sup>-2</sup>s<sup>-1</sup> in dry season. The water balance, that shows periods of water excess (EXC) and water deficit (DEF) before collecting days can be seen in supporting information (<xref ref-type="supplementary-material" rid="pone.0149332.s001">S1 Fig</xref>).</p></sec><sec id="sec004"><title>Ethics statement</title><p>Necessary permits for the field study was obtained by Dr. Luiz Fernando Rolim de Almeida to Ministério do Meio Ambiente—MMA, Instituto Brasileiro do Meio Ambiente e dos Recursos Naturais Renováveis–IBAMA (the Brazilian Environmental Institute), Sistema de Autorização e Informação em Biodiversidade—SISBIO, process n° 26541–1; authentication code n° 84241528. The location where the plants were collected were not privately owned or protected in any way and the field studies did not involve endangered or protected species.</p></sec><sec id="sec005"><title>Extraction and analysis of essential oils</title><p>The essential oils were extracted by hydrodistillation using a Clevenger apparatus. Each sample consisted of 50 g of dried leaves distilled for 120 min. The essential oil yield was calculated by weight as (g) of oil per (g) of dry material and expressed as percentage of oil in the dried leaves. The quantitative analysis of the essential oil compounds was obtained by gas-chromatograph GC (Shimadzu GC-2010) equipped with flame ionization (GC–FID) and using a DB-5 (J and W Scientific; 30 m × 0.25 mm × 0.25 mm × 0.25 μm) capillary column. Helium was used as the carrier gas, and the injector temperature was 240˚C.; the detector temperature was 230˚C, the gas flowed at 1.0 mL/minute, and it was split 1/20. The temperature program was set at 60˚C-200˚C at 3˚C/minute and 200˚C-240˚C at 15˚C/minute. The injection temperature was 230˚C. The injection volume was 1.0μL and consisted of a sample preparation that included 1.0 μL of essential oils added into 1.0 mL of ethyl acetate. The qualitative analysis of the essential oil compounds was performed on a gas-chromatograph (GC) coupled to a mass spectrometer (MS; GC–MS; Shimadzu QP-5000) operating at a MS ionization voltage of 70 eV. The chromatograph was equipped with a fused silica capillary column DB-5 (J and W Scientific; 30 m × 0.25 mm × 0.25 μm), and helium was used as the carrier gas. The temperature program was 60˚C-240˚C at 3˚C/minute. The injection temperature was 220˚C. The injection volume was 1.0 μL of sample preparation that contained 1.0 μL of essential oils added into 1.0 mL of ethyl acetate. The compounds were identified by comparing their mass spectrum to those of the database on the GC-MS (NIST 62.lib and Wiley 139.Lib) literature [<xref rid="pone.0149332.ref027" ref-type="bibr">27</xref>] and retention indices [<xref rid="pone.0149332.ref028" ref-type="bibr">28</xref>]. The retention index (RI) was obtained by injection injecting a mixture of n-alkanes (C9-C24) and applying the equation of the method of [<xref rid="pone.0149332.ref029" ref-type="bibr">29</xref>]. The data were analyzed with three repetitions per period of data collection.</p></sec><sec id="sec006"><title>Statistical analysis</title><p>We performed multivariate and box plot analyses following the values of major compounds. In addition, an agglomerative hierarchical cluster (AHC) was performed following a 118 squared Euclidean distance dissimilarity matrix, which was calculated by the Ward’s linkage. We also constructed a matrix of correlation by a principal component analysis (PCA) and to identify whether a significant difference exists between the means of two groups—6:00 am and 5:00 pm—during the wet and dry seasons we used Student's t-test (p ≤ 0.05).</p></sec></sec><sec id="sec007"><title>Results and Discussion</title><sec id="sec008"><title>Chemical profile of essential oils</title><p>The phytochemical profile of the essential oils from <italic>C</italic>. <italic>langsdorffii</italic> leaves showed 17 compounds, namely 13 non-oxygenated sesquiterpenes and four oxygenated sesquiterpenes (<xref ref-type="table" rid="pone.0149332.t001">Table 1</xref>). The essential oil yield was an average from 0.03–0.05% without significance difference between seasonal and diurnal variation (<xref ref-type="table" rid="pone.0149332.t001">Table 1</xref>). The major compounds were germacrene D, β-caryophyllene, bicyclogermacrene, spathulenol, caryophyllene oxide and α-cadinol (<xref ref-type="table" rid="pone.0149332.t001">Table 1</xref>). A comparable result was previously reported by [<xref rid="pone.0149332.ref020" ref-type="bibr">20</xref>], who found β-caryophyllene, germacrene D, spathulenol and caryophyllene oxide in the essential oils from <italic>C</italic>. <italic>langsdorffii</italic> leaves. Similar results were reported by [<xref rid="pone.0149332.ref030" ref-type="bibr">30</xref>] for the leaves, fruits, trunk and roots of <italic>C</italic>. <italic>langsdorffii</italic>, all of which contained β-caryophyllene and caryophyllene oxide in their volatile fraction. Germacrene D has been previously reported to be one of the main components of <italic>Copaifera officinalis</italic> (Jacq.) L. among the 25 sesquiterpenes found in the leaf tissues of this plant [<xref rid="pone.0149332.ref031" ref-type="bibr">31</xref>]. Furthermore, other authors have reported the chemical composition of <italic>Copaifera</italic> species [<xref rid="pone.0149332.ref032" ref-type="bibr">32</xref>–<xref rid="pone.0149332.ref034" ref-type="bibr">34</xref>] and revealed the same compounds detected in the <italic>C</italic>. <italic>langsdorffii</italic> essential oils in this study.</p><table-wrap id="pone.0149332.t001" orientation="portrait" position="float"><object-id pub-id-type="doi">10.1371/journal.pone.0149332.t001</object-id><label>Table 1</label><caption><title>Average of essential oil composition and yield of <italic>Copaifera langsdorffii</italic> Desf. from a semideciduous seasonal forest at 6:00 am and 5:00 pm during the wet and dry seasons.</title></caption><alternatives><graphic id="pone.0149332.t001g" xlink:href="pone.0149332.t001"></graphic><table frame="hsides" rules="groups"><colgroup span="1"><col align="left" valign="middle" span="1"></col><col align="left" valign="middle" span="1"></col><col align="left" valign="middle" span="1"></col><col align="left" valign="middle" span="1"></col><col align="left" valign="middle" span="1"></col><col align="left" valign="middle" span="1"></col><col align="left" valign="middle" span="1"></col><col align="left" valign="middle" span="1"></col><col align="left" valign="middle" span="1"></col><col align="left" valign="middle" span="1"></col></colgroup><thead><tr><th align="center" rowspan="2" colspan="1">Compounds (%)</th><th align="center" colspan="2" rowspan="1">Wet season</th><th align="center" rowspan="1" colspan="1"></th><th align="center" colspan="2" rowspan="1">Dry season</th><th align="center" rowspan="1" colspan="1"></th><th align="center" rowspan="1" colspan="1">RI exp</th><th align="left" rowspan="2" colspan="1">RI lit</th><th align="center" rowspan="2" colspan="1">Method of identification</th></tr><tr><th align="center" rowspan="1" colspan="1">6:00 am</th><th align="center" rowspan="1" colspan="1">5:00 pm</th><th align="center" rowspan="1" colspan="1">t-test</th><th align="center" rowspan="1" colspan="1">6:00 am</th><th align="center" rowspan="1" colspan="1">5:00 pm</th><th align="center" rowspan="1" colspan="1">t-test</th><th align="center" rowspan="1" colspan="1"></th></tr></thead><tbody><tr><td align="left" rowspan="1" colspan="1"><italic>Non-oxygenated sesquiterpenes</italic></td><td align="center" rowspan="1" colspan="1"></td><td align="center" rowspan="1" colspan="1"></td><td align="center" rowspan="1" colspan="1"></td><td align="center" rowspan="1" colspan="1"></td><td align="center" rowspan="1" colspan="1"></td><td align="center" rowspan="1" colspan="1"></td><td align="center" rowspan="1" colspan="1"></td><td align="center" rowspan="1" colspan="1"></td><td align="center" rowspan="1" colspan="1"></td></tr><tr><td align="left" rowspan="1" colspan="1">α-Copaene</td><td align="center" rowspan="1" colspan="1">0.24 ± 0.04</td><td align="center" rowspan="1" colspan="1">0.34 ± 0.13</td><td align="center" rowspan="1" colspan="1">ns</td><td align="center" rowspan="1" colspan="1">tr</td><td align="center" rowspan="1" colspan="1">1.49 ± 0.62</td><td align="center" rowspan="1" colspan="1">-</td><td align="center" rowspan="1" colspan="1">1373</td><td align="center" rowspan="1" colspan="1">1376</td><td align="center" rowspan="1" colspan="1">MS, RI</td></tr><tr><td align="left" rowspan="1" colspan="1">β-Elemene</td><td align="center" rowspan="1" colspan="1">0.79 ± 0.29</td><td align="center" rowspan="1" colspan="1">0.82 ± 0.14</td><td align="center" rowspan="1" colspan="1">ns</td><td align="center" rowspan="1" colspan="1">tr</td><td align="center" rowspan="1" colspan="1">1.21 ± 0.50</td><td align="center" rowspan="1" colspan="1">-</td><td align="center" rowspan="1" colspan="1">1389</td><td align="center" rowspan="1" colspan="1">1391</td><td align="center" rowspan="1" colspan="1">MS, RI</td></tr><tr><td align="left" rowspan="1" colspan="1">β –Caryophyllene</td><td align="center" rowspan="1" colspan="1">5.47 ± 6.19</td><td align="center" rowspan="1" colspan="1">2.15 ± 0.79</td><td align="center" rowspan="1" colspan="1">ns</td><td align="center" rowspan="1" colspan="1">1.07 ± 0.77</td><td align="center" rowspan="1" colspan="1">9.02 ± 0.17</td><td align="center" rowspan="1" colspan="1"><xref ref-type="table-fn" rid="t001fn002">*</xref></td><td align="center" rowspan="1" colspan="1">1416</td><td align="center" rowspan="1" colspan="1">1418</td><td align="center" rowspan="1" colspan="1">MS, RI</td></tr><tr><td align="left" rowspan="1" colspan="1">γ-Gurjunene</td><td align="center" rowspan="1" colspan="1">tr</td><td align="center" rowspan="1" colspan="1">tr</td><td align="center" rowspan="1" colspan="1">-</td><td align="center" rowspan="1" colspan="1">tr</td><td align="center" rowspan="1" colspan="1">0.29 ± 0.05</td><td align="center" rowspan="1" colspan="1">-</td><td align="center" rowspan="1" colspan="1">1426</td><td align="center" rowspan="1" colspan="1">1432</td><td align="center" rowspan="1" colspan="1">MS, RI</td></tr><tr><td align="left" rowspan="1" colspan="1">γ-Elemene</td><td align="center" rowspan="1" colspan="1">tr</td><td align="center" rowspan="1" colspan="1">tr</td><td align="center" rowspan="1" colspan="1">-</td><td align="center" rowspan="1" colspan="1">tr</td><td align="center" rowspan="1" colspan="1">tr</td><td align="center" rowspan="1" colspan="1">-</td><td align="center" rowspan="1" colspan="1">1436</td><td align="center" rowspan="1" colspan="1">1439</td><td align="center" rowspan="1" colspan="1">MS, RI</td></tr><tr><td align="left" rowspan="1" colspan="1">α –Humulene</td><td align="center" rowspan="1" colspan="1">0.88 ± 0.89</td><td align="center" rowspan="1" colspan="1">0.40 ± 0.07</td><td align="center" rowspan="1" colspan="1">ns</td><td align="center" rowspan="1" colspan="1">tr</td><td align="center" rowspan="1" colspan="1">1.30 ± 0.14</td><td align="center" rowspan="1" colspan="1">-</td><td align="center" rowspan="1" colspan="1">1450</td><td align="center" rowspan="1" colspan="1">1454</td><td align="center" rowspan="1" colspan="1">MS, RI</td></tr><tr><td align="left" rowspan="1" colspan="1">γ-Muurolene</td><td align="center" rowspan="1" colspan="1">0.56 ±0.26</td><td align="center" rowspan="1" colspan="1">0.54 ± 0.10</td><td align="center" rowspan="1" colspan="1">ns</td><td align="center" rowspan="1" colspan="1">0.40 ± 0.37</td><td align="center" rowspan="1" colspan="1">1.31 ± 0.09</td><td align="center" rowspan="1" colspan="1"><xref ref-type="table-fn" rid="t001fn002">*</xref></td><td align="center" rowspan="1" colspan="1">1476</td><td align="center" rowspan="1" colspan="1">1477</td><td align="center" rowspan="1" colspan="1">MS, RI</td></tr><tr><td align="left" rowspan="1" colspan="1">Germacrene D</td><td align="center" rowspan="1" colspan="1">14.11 ± 14.88</td><td align="center" rowspan="1" colspan="1">7.73 ± 4.98</td><td align="center" rowspan="1" colspan="1">ns</td><td align="center" rowspan="1" colspan="1">4.01 ± 4.44</td><td align="center" rowspan="1" colspan="1">17.99 ± 4.35</td><td align="center" rowspan="1" colspan="1"><xref ref-type="table-fn" rid="t001fn002">*</xref></td><td align="center" rowspan="1" colspan="1">1478</td><td align="center" rowspan="1" colspan="1">1480</td><td align="center" rowspan="1" colspan="1">MS, RI</td></tr><tr><td align="left" rowspan="1" colspan="1">Bicyclogermacrene</td><td align="center" rowspan="1" colspan="1">4.72 ± 5.33</td><td align="center" rowspan="1" colspan="1">2.33 ± 1.14</td><td align="center" rowspan="1" colspan="1">ns</td><td align="center" rowspan="1" colspan="1">1.51 ± 1.86</td><td align="center" rowspan="1" colspan="1">5.68 ± 0.91</td><td align="center" rowspan="1" colspan="1"><xref ref-type="table-fn" rid="t001fn002">*</xref></td><td align="center" rowspan="1" colspan="1">1495</td><td align="center" rowspan="1" colspan="1">1494</td><td align="center" rowspan="1" colspan="1">MS, RI</td></tr><tr><td align="left" rowspan="1" colspan="1">α –Muurolene</td><td align="center" rowspan="1" colspan="1">0.54 ± 0.55</td><td align="center" rowspan="1" colspan="1">0.26 ± 0.06</td><td align="center" rowspan="1" colspan="1">ns</td><td align="center" rowspan="1" colspan="1">0.47 ± 0.48</td><td align="center" rowspan="1" colspan="1">1.38 ± 0.09</td><td align="center" rowspan="1" colspan="1"><xref ref-type="table-fn" rid="t001fn002">*</xref></td><td align="center" rowspan="1" colspan="1">1497</td><td align="center" rowspan="1" colspan="1">1499</td><td align="center" rowspan="1" colspan="1">MS, RI</td></tr><tr><td align="left" rowspan="1" colspan="1">γ-Cadinene</td><td align="center" rowspan="1" colspan="1">0.63 ± 0.27</td><td align="center" rowspan="1" colspan="1">0.51 ± 0.09</td><td align="center" rowspan="1" colspan="1">ns</td><td align="center" rowspan="1" colspan="1">0.79 ± 0.54</td><td align="center" rowspan="1" colspan="1">1.31 ± 0.17</td><td align="center" rowspan="1" colspan="1">ns</td><td align="center" rowspan="1" colspan="1">1512</td><td align="center" rowspan="1" colspan="1">1513</td><td align="center" rowspan="1" colspan="1">MS, RI</td></tr><tr><td align="left" rowspan="1" colspan="1">δ-Cadinene</td><td align="center" rowspan="1" colspan="1">3.07 ± 2.12</td><td align="center" rowspan="1" colspan="1">1.80 ± 0.67</td><td align="center" rowspan="1" colspan="1">ns</td><td align="center" rowspan="1" colspan="1">1.75 ± 1.75</td><td align="center" rowspan="1" colspan="1">2.72 ± 0.33</td><td align="center" rowspan="1" colspan="1">ns</td><td align="center" rowspan="1" colspan="1">1522</td><td align="center" rowspan="1" colspan="1">1524</td><td align="center" rowspan="1" colspan="1">MS, RI</td></tr><tr><td align="left" rowspan="1" colspan="1">Germacrene B</td><td align="center" rowspan="1" colspan="1">1.48 ± 0.64</td><td align="center" rowspan="1" colspan="1">1.72 ± 0.09</td><td align="center" rowspan="1" colspan="1">ns</td><td align="center" rowspan="1" colspan="1">1.36 ± 0.31</td><td align="center" rowspan="1" colspan="1">1.80 ± 1.49</td><td align="center" rowspan="1" colspan="1">ns</td><td align="center" rowspan="1" colspan="1">1557</td><td align="center" rowspan="1" colspan="1">1556</td><td align="center" rowspan="1" colspan="1">MS, RI</td></tr><tr><td align="left" rowspan="1" colspan="1"><italic>Oxygenated sesquiterpenes</italic></td><td align="center" rowspan="1" colspan="1"></td><td align="center" rowspan="1" colspan="1"></td><td align="center" rowspan="1" colspan="1"></td><td align="center" rowspan="1" colspan="1"></td><td align="center" rowspan="1" colspan="1"></td><td align="center" rowspan="1" colspan="1"></td><td align="center" rowspan="1" colspan="1"></td><td align="center" rowspan="1" colspan="1"></td><td align="center" rowspan="1" colspan="1"></td></tr><tr><td align="left" rowspan="1" colspan="1">Spathulenol</td><td align="center" rowspan="1" colspan="1">27.39 ± 16.31</td><td align="center" rowspan="1" colspan="1">35.65 ± 3.54</td><td align="center" rowspan="1" colspan="1">ns</td><td align="center" rowspan="1" colspan="1">25.90 ± 12.28</td><td align="center" rowspan="1" colspan="1">12.55 ± 11.11</td><td align="center" rowspan="1" colspan="1">ns</td><td align="center" rowspan="1" colspan="1">1576</td><td align="center" rowspan="1" colspan="1">1576</td><td align="center" rowspan="1" colspan="1">MS, RI</td></tr><tr><td align="left" rowspan="1" colspan="1">Caryophyllene oxide</td><td align="center" rowspan="1" colspan="1">14.49 ± 7.03</td><td align="center" rowspan="1" colspan="1">16.32 ± 3.63</td><td align="center" rowspan="1" colspan="1">ns</td><td align="center" rowspan="1" colspan="1">16.55 ± 5.56</td><td align="center" rowspan="1" colspan="1">7.40 ± 1.14</td><td align="center" rowspan="1" colspan="1">ns</td><td align="center" rowspan="1" colspan="1">1581</td><td align="center" rowspan="1" colspan="1">1581</td><td align="center" rowspan="1" colspan="1">MS, RI</td></tr><tr><td align="left" rowspan="1" colspan="1">Humulene epoxy II</td><td align="center" rowspan="1" colspan="1">2.12 ± 1.46</td><td align="center" rowspan="1" colspan="1">2.59 ± 0.04</td><td align="center" rowspan="1" colspan="1">ns</td><td align="center" rowspan="1" colspan="1">2.63 ± 0.40</td><td align="center" rowspan="1" colspan="1">1.73 ± 0.08</td><td align="center" rowspan="1" colspan="1"><xref ref-type="table-fn" rid="t001fn002">*</xref></td><td align="center" rowspan="1" colspan="1">1604</td><td align="center" rowspan="1" colspan="1">1606</td><td align="center" rowspan="1" colspan="1">MS, RI</td></tr><tr><td align="left" rowspan="1" colspan="1">α-Cadinol</td><td align="center" rowspan="1" colspan="1">3.25 ± 0.99</td><td align="center" rowspan="1" colspan="1">3.2 ± 0.46</td><td align="center" rowspan="1" colspan="1">ns</td><td align="center" rowspan="1" colspan="1">7.93 ± 4.54</td><td align="center" rowspan="1" colspan="1">5.24 ± 0.94</td><td align="center" rowspan="1" colspan="1">ns</td><td align="center" rowspan="1" colspan="1">1650</td><td align="center" rowspan="1" colspan="1">1653</td><td align="center" rowspan="1" colspan="1">MS, RI</td></tr><tr><td align="left" rowspan="1" colspan="1">Non-oxygenated sesquiterpenes</td><td align="center" rowspan="1" colspan="1">32.49</td><td align="center" rowspan="1" colspan="1">18.60</td><td align="center" rowspan="1" colspan="1"></td><td align="center" rowspan="1" colspan="1">11.36</td><td align="center" rowspan="1" colspan="1">45.50</td><td align="center" rowspan="1" colspan="1"></td><td align="center" rowspan="1" colspan="1"></td><td align="center" rowspan="1" colspan="1"></td><td align="center" rowspan="1" colspan="1"></td></tr><tr><td align="left" rowspan="1" colspan="1">Oxygenated sesquiterpenes</td><td align="center" rowspan="1" colspan="1">47.25</td><td align="center" rowspan="1" colspan="1">57.76</td><td align="center" rowspan="1" colspan="1"></td><td align="center" rowspan="1" colspan="1">53.01</td><td align="center" rowspan="1" colspan="1">26.92</td><td align="center" rowspan="1" colspan="1"></td><td align="center" rowspan="1" colspan="1"></td><td align="center" rowspan="1" colspan="1"></td><td align="center" rowspan="1" colspan="1"></td></tr><tr><td align="left" rowspan="1" colspan="1">Ratio (Non-oxygenated sesquiterpenes/Oxygenated sesquiterpenes)</td><td align="center" rowspan="1" colspan="1">0.69</td><td align="center" rowspan="1" colspan="1">0.32</td><td align="center" rowspan="1" colspan="1"></td><td align="center" rowspan="1" colspan="1">0.21</td><td align="center" rowspan="1" colspan="1">1.69</td><td align="center" rowspan="1" colspan="1"></td><td align="center" rowspan="1" colspan="1"></td><td align="center" rowspan="1" colspan="1"></td><td align="center" rowspan="1" colspan="1"></td></tr><tr><td align="left" rowspan="1" colspan="1">Yield of essential oils (%)</td><td align="center" rowspan="1" colspan="1">0.04 ± 0.02</td><td align="center" rowspan="1" colspan="1">0.04 ± 0.03</td><td align="center" rowspan="1" colspan="1">ns</td><td align="center" rowspan="1" colspan="1">0.03 ± 0.01</td><td align="left" rowspan="1" colspan="1">0.05 ± 0.04</td><td align="center" rowspan="1" colspan="1">ns</td><td align="center" rowspan="1" colspan="1"></td><td align="center" rowspan="1" colspan="1"></td><td align="center" rowspan="1" colspan="1"></td></tr></tbody></table></alternatives><table-wrap-foot><fn id="t001fn001"><p>RIexp.: experimental Retention Index. RI lit.: Retention Index found on literature. tr: trace amount (≤ 0.001). MS, identification based on comparison of mass spectra. RI, identification based on retention index.</p></fn><fn id="t001fn002"><p>*p ≤ 0.05 (statistical significance).</p></fn><fn id="t001fn003"><p>ns: non-significant.</p></fn></table-wrap-foot></table-wrap><p>The weather conditions, particularly light intensity and precipitations, affected the essential oil composition. During the dry season, the average precipitation was 52.88 mm, and this value reached 582.88 mm during the wet season. A decrease in the light intensity was observed during the wet season, with an average of 286 μmol m<sup>-2</sup>s<sup>-1</sup>, whereas the dry season presented an average of 665.67 μmol m<sup>-2</sup>s<sup>-1</sup>. As a result, the main compounds of non-oxygenated sesquiterpenes and oxygenated sesquiterpenes showed higher or lower amounts depending on the average light intensity and precipitation during early mornings and afternoons.</p><p>Previous studies reported that weather parameters, such as atmospheric temperature and rainfall, influence the oil content and composition of several aromatic plants [<xref rid="pone.0149332.ref035" ref-type="bibr">35</xref>]. In agreement with those results, our study demonstrates that the essential oil composition of <italic>C</italic>. <italic>langsdorffii</italic> was affected by environmental factors, such as rainfall and light intensity. In addition, a decrease in the average temperature observed during the dry season could also alter the pattern of sesquiterpene production.</p><p>In <xref ref-type="table" rid="pone.0149332.t001">Table 1</xref>, the ratio of non-oxygenated sesquiterpenes versus oxygenated sesquiterpenes showed an inversion during the dry season at the end the day (1.69). A ratio of non-oxygenated sesquiterpenes/oxygenated sesquiterpenes higher than 1.0 reports an elevated level of non-oxygenated sesquiterpenes observed at 5:00 pm during the dry season. It have been suggested by others studies [<xref rid="pone.0149332.ref017" ref-type="bibr">17</xref>,<xref rid="pone.0149332.ref015" ref-type="bibr">15</xref>,<xref rid="pone.0149332.ref016" ref-type="bibr">16</xref>] that variations in the terpene levels throughout the day constitute evidence of the up and down regulations of a specialized metabolism influenced by environmental factors.</p><p>The non-oxygenated sesquiterpenes, i.e., germacrene D, β-caryophyllene and bicyclogermacrene, showed a higher trend during the early harvesting of leaves and decreased thereafter in the wet season. Therefore, during the dry season, those compounds presented a higher trend at 5:00 pm (<xref ref-type="table" rid="pone.0149332.t001">Table 1</xref>). The oxygenated sesquiterpenes, i.e., spathulenol and caryophyllene oxide compounds, showed a higher trend at 5:00 pm during the wet season and at the early morning harvest during the dry season. α-Cadinol showed a higher tendency at 6:00 am and opposite trend after that time during the dry season (<xref ref-type="table" rid="pone.0149332.t001">Table 1</xref>). In the present study, the non-oxygenated sesquiterpenes decreased in the late harvest during wet season; however, a reverse trend was observed during dry season.</p><p>The most important environmental abiotic factors that influence plant growth and development are water availability and temperature [<xref rid="pone.0149332.ref024" ref-type="bibr">24</xref>], as well as light also can contribute on modifying plant metabolism [<xref rid="pone.0149332.ref036" ref-type="bibr">36</xref>–<xref rid="pone.0149332.ref038" ref-type="bibr">38</xref>]. According with literature, 20% of sesquiterpene emissions are impacted by temperature and 80% by temperature and light together [<xref rid="pone.0149332.ref039" ref-type="bibr">39</xref>,<xref rid="pone.0149332.ref040" ref-type="bibr">40</xref>]. <italic>Lippia origanoides</italic> Kunth showed higher oxygenated sesquiterpenes levels during wet season and a predominance of oxygenated monoterpenes and monoterpenes hydrocarbons during dry season [<xref rid="pone.0149332.ref041" ref-type="bibr">41</xref>].</p><p>Based upon observation, our results show that multiple environmental factors change the specialized metabolism on plants, resulting in production of different terpenes. This suggests that chemical profile showed on this study is result of accumulating environmental signals on leaves such as water availability variation, the raising of light hours during the day and temperature. Furthermore, it should be noted that signaling of the environment in plant metabolism can be seen in our results, mostly by the inversion of the ratio of non-oxygenated sesquiterpene and oxygenated sesquiterpenes at the end of dry days.</p><p>The quality of the essential oils of <italic>C</italic>. <italic>langsdorffii</italic> was affected by the time of the day and seasonal variations. For instance, the two major compounds, i.e., germacrene D and spathulenol, showed opposite results according to seasonal and diurnal variations. Germacrene D (non-oxygenated sesquiterpene) showed an increasing tendency during the early mornings of the wet season as well as during the dry season at 5:00 pm (<xref ref-type="table" rid="pone.0149332.t001">Table 1</xref>). In contrast, spathulenol (oxygenated sesquiterpene) presented an increasing trend during the dry season at 6:00 am and during the wet season at 5:00 pm (<xref ref-type="table" rid="pone.0149332.t001">Table 1</xref>). This result suggests that the light intensity and water availability can influence sesquiterpene biosynthesis and production. Moreover, this variation in the chemical profile of essential oils can alter their medicinal activity because essential oils offer a complex mixture of substances and, generally, the major compounds are the ones responsible for their biological properties [<xref rid="pone.0149332.ref010" ref-type="bibr">10</xref>].</p></sec><sec id="sec009"><title>Multivariate analysis of major compounds</title><p>We applied a principal component analysis (PCA) to assess the composition of the essential oils from <italic>C</italic>. <italic>langsdorffii</italic> and to identify a possible correlation between the main compounds and the seasonal and diurnal variations (<xref ref-type="fig" rid="pone.0149332.g001">Fig 1</xref>). The principal factorial plane accounts for 93.68% of all major compounds. In addition, the PC1 axis (73.69%) shows that the non-oxygenated sesquiterpenes (germacrene D, bicyclogermacrene and β-caryophyllene) were positively correlated with the afternoon (5:00 pm) harvest of the dry season. The oxygenated sesquiterpenes (spathulenol and caryophyllene oxide) were correlated with both harvests (6:00 am and 5:00 pm) of the wet season. In contrast, α-Cadinol was the only compound that was not correlated with seasons and harvesting periods.</p><fig id="pone.0149332.g001" orientation="portrait" position="float"><object-id pub-id-type="doi">10.1371/journal.pone.0149332.g001</object-id><label>Fig 1</label><caption><title>PCA of the main compounds present in the essential oil of <italic>Copaifera langsdorffii</italic> Desf from a semideciduous seasonal forest at 6:00 am and 5:00 pm during the dry season (DS) and the wet season (WS).</title></caption><graphic xlink:href="pone.0149332.g001"></graphic></fig><p>The pattern of the major essential oil compounds of <italic>C</italic>. <italic>langsdorffii</italic> was categorized into three groups through cluster and box plot analyses (Figs <xref ref-type="fig" rid="pone.0149332.g002">2</xref> and <xref ref-type="fig" rid="pone.0149332.g003">3</xref>, respectively). The first group consisted of the compounds present during the wet season at 6:00 am and the wet season at 5:00 pm; the second group consisted of the compounds present during the dry season at 6:00 am; and the third group consisted of the compounds present during the dry season at 5:00 pm (<xref ref-type="fig" rid="pone.0149332.g002">Fig 2</xref>). Our data show that β-caryophyllene, germacrene D and bicyclogermacrene had the highest values in group 3. Likewise, spathulenol and caryophyllene oxide had the highest values in group 1 and 2 (<xref ref-type="fig" rid="pone.0149332.g003">Fig 3</xref>). Furthermore, the PCA analysis reveals a correlation between the oxygenated sesquiterpenes and the wet season as well as between the 5:00 pm harvests of the dry season with the non-oxygenated sesquiterpenes.</p><fig id="pone.0149332.g002" orientation="portrait" position="float"><object-id pub-id-type="doi">10.1371/journal.pone.0149332.g002</object-id><label>Fig 2</label><caption><title>Agglomerative Hierarchical Clustering (AHC) calculated with the Ward’s linkage and Euclidean distance, which correlates the essential oil data from a semideciduous seasonal forest.</title><p>Wet Season at 6:00 am (WS 6am) and Wet Season at 5:00 pm (WS 5pm)—Group 1; Dry Season at 6:00 am (DS 6am)—Group 2; Dry Season at 5:00 pm (DS 5pm)—Group 3.</p></caption><graphic xlink:href="pone.0149332.g002"></graphic></fig><fig id="pone.0149332.g003" orientation="portrait" position="float"><object-id pub-id-type="doi">10.1371/journal.pone.0149332.g003</object-id><label>Fig 3</label><caption><title>Box plot analyses of the major compounds (%) present in the essential oil from leaves of <italic>Copaifera langsdorffii</italic> Desf.</title><p>β-Caryophyllene, germacrene D and bicyclogermacrene (non-oxygenated sesquiterpenes); spathulenol, caryophyllene oxide and α-cadinol (oxygenated sesquiterpenes). Wet season at 6:00 am and wet season at 5:00 pm—Group 1; dry season at 6:00 am—Group 2; dry season at 5:00 pm—Group 3.</p></caption><graphic xlink:href="pone.0149332.g003"></graphic></fig><p>The light wavelength and intensity well as the exposure time are essential features for the biosynthesis of metabolites in plant cells [<xref rid="pone.0149332.ref042" ref-type="bibr">42</xref>]. The flux of terpenes found in <italic>Citrus sinensis</italic> (L.) Osbeck, <italic>C</italic>. <italic>clementii</italic>, and <italic>Picea abies</italic> (L.) H. Karst. followed diurnal variations controlled by temperature, with maximum concentrations during midday and minimal concentrations during the evenings and mornings [<xref rid="pone.0149332.ref043" ref-type="bibr">43</xref>]. The peak emissions of isoprene occurred during mid-afternoon hours. Instead, the α-pinene-to-β-pinene ratio were high during early morning and late afternoon [<xref rid="pone.0149332.ref044" ref-type="bibr">44</xref>]. Moreover, α-cadinol and caryophyllene oxide presented the highest concentrations at 7:00 pm in <italic>Pycnocycla spinosa</italic> Decne. ex Boiss. [<xref rid="pone.0149332.ref042" ref-type="bibr">42</xref>], and high temperatures influenced the release of <italic>trans</italic>-caryophyllene [<xref rid="pone.0149332.ref045" ref-type="bibr">45</xref>]. Sesquiterpenes had the highest levels at 6:00 pm in August, and the main compound of the essential oils from leaves of <italic>Cistus monspeliensis</italic> L. was caryophyllene oxide [<xref rid="pone.0149332.ref046" ref-type="bibr">46</xref>]. The highest levels of carvacrol in the essential oils of <italic>Origanum onites</italic> L. occurred at 10:00 am and the lowest at 06:00 am [<xref rid="pone.0149332.ref047" ref-type="bibr">47</xref>]. The authors reported that the thymol content was higher at 12:00 am (23.76%) and lower at 08:00 pm. These authors also showed a biosynthetic correlation between thymol and carvacrol based on the dynamic levels of these compounds. In the present study, germacrene D, β-caryophyllene and bicyclogermacrene were upregulated during the dry season and downregulated during the wet season. In addition, spathulenol and caryophyllene oxide were upregulated during the wet season and downregulated during the dry season. Therefore, we now have a better understanding of the metabolic adjustments during injuries are regulated by the environmental status. Furthermore, it is necessary to understand the association between the sesquiterpene metabolism and the effects of these compounds on the plants.</p><p>Additionally, we believe that the leaf protection against herbivory and pathogens occurs as a physiological response against biotic stresses. For instance, <italic>C</italic>. <italic>langsdorffii</italic> maintains part of its leaves during stressful events, and it is classified as a perennial species [<xref rid="pone.0149332.ref019" ref-type="bibr">19</xref>]. Hussain et al. found in <italic>Ocimum basilicum</italic> L. a seasonal trend in the oxygenated and non-oxygenated sesquiterpene production [<xref rid="pone.0149332.ref012" ref-type="bibr">12</xref>]. These authors observed high amounts of oxygenated sesquiterpenes during winter and a minimal production of sesquiterpene hydrocarbons and, an opposite trend, during the summer. According to our results, we believe that stressful events, such as water scarcity, increase the production of non-oxygenated sesquiterpenes. Therefore, these compounds display important medicinal properties, as reported by [<xref rid="pone.0149332.ref048" ref-type="bibr">48</xref>], who showed the antimicrobial activity of germacrene D present in the essential oil of <italic>Ageratum fastigiatum</italic> (Gardner) R.M. King & H. Rob. Similarly, the essential oils from <italic>Murraya koenigii</italic> (L.) Spreng. showed antibacterial effects due to the presence of β-caryophyllene [<xref rid="pone.0149332.ref049" ref-type="bibr">49</xref>]; in addition, the essential oils of <italic>Callicarpa japonica</italic> Thunb. were found to exert phytotoxic effects due to the presence of bicyclogermacrene and germacrene D [<xref rid="pone.0149332.ref050" ref-type="bibr">50</xref>]. Furthermore, oxygenated sesquiterpenes also displays biological properties, for instance, spathulenol found in essential oils of <italic>Nepeta glomerata</italic> Montbret et Aucher ex Bentham that showed cytotoxic and antibacterial activities [<xref rid="pone.0149332.ref051" ref-type="bibr">51</xref>] and it was the major constituent (4.5%) in <italic>Achillea cretica</italic> essential oil responsible for antimicrobial activity [<xref rid="pone.0149332.ref052" ref-type="bibr">52</xref>]. Therefore, research on the properties of the compounds found in the oleoresin of <italic>Copaifera</italic> species [<xref rid="pone.0149332.ref021" ref-type="bibr">21</xref>] and studies regarding the environmental influence on the terpenoid metabolism are essential for obtaining the highest concentrations of natural products with beneficial properties to human health.</p></sec></sec><sec sec-type="conclusions" id="sec010"><title>Conclusions</title><p>This study demonstrates that the diurnal variation in light intensity and water accumulation during the different seasons control the sesquiterpene levels of the essential oil composition of <italic>C</italic>. <italic>langsdorffii</italic>. Harvests performed at 5:00 pm in dry days resulted in oils of <italic>C</italic>. <italic>langsdorffii</italic> with a higher percentages of non-oxygenated sesquiterpenes. These data support the importance of monitoring the metabolic responses of plants caused by environmental factors. This type of ecological research revealed a method for obtaining the maximum concentrations of bioactive compounds used for medicine.</p></sec><sec sec-type="supplementary-material" id="sec011"><title>Supporting Information</title><supplementary-material content-type="local-data" id="pone.0149332.s001"><label>S1 Fig</label><caption><title>Water balance per month at semideciduous seasonal forest, Cerrado physiognomy.</title><p>The wet season represent an accumulation of water, as well as dry season a period of deficiency of water availability. EXC–water excess; DEF–water deficit.</p><p>(DOC)</p></caption><media xlink:href="pone.0149332.s001.doc"><caption><p>Click here for additional data file.</p></caption></media></supplementary-material></sec></body><back><ack><p>This work was supported by the Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP), process n° 2010/15585-6 and n° 2013/07629-1.</p></ack><ref-list><title>References</title><ref id="pone.0149332.ref001"><label>1</label><mixed-citation publication-type="journal"><name><surname>Figueiredo</surname><given-names>AC</given-names></name>, <name><surname>Barroso</surname><given-names>JG</given-names></name>, <name><surname>Pedro</surname><given-names>LG</given-names></name>, <name><surname>Scheffer</surname><given-names>JJC</given-names></name>. <article-title>Factors affecting secondary metabolite production in plants: volatile components and essential oils</article-title>. <source>Flavour Frang. J</source>. <year>2008</year>; <volume>23</volume>(<issue>4</issue>):<fpage>213</fpage>–<lpage>226</lpage>.</mixed-citation></ref><ref id="pone.0149332.ref002"><label>2</label><mixed-citation publication-type="journal"><name><surname>Lincoln</surname><given-names>DE</given-names></name>, <name><surname>Langenheim</surname><given-names>JH</given-names></name>. <article-title>Effect of light and temperature on monoterpenoid yield and composition in <italic>Satureja douglasii</italic> Numbers correspond to the affiliation list which can be exposed by using the show more link</article-title>. <source>Biochem. Syst. Ecol</source>. <year>1978</year>; <volume>6</volume>(<issue>1</issue>):<fpage>21</fpage>–<lpage>32</lpage>.</mixed-citation></ref><ref id="pone.0149332.ref003"><label>3</label><mixed-citation publication-type="journal"><name><surname>McGimpsey</surname><given-names>JA</given-names></name>, <name><surname>Douglas</surname><given-names>MH</given-names></name>, <name><surname>Van Klink</surname><given-names>JW</given-names></name>, <name><surname>Beauregard</surname><given-names>DA</given-names></name>, <name><surname>Perry</surname><given-names>NB</given-names></name>. <article-title>Seasonal variation in essential oil yield and composition from naturalized <italic>thymus vulgaris</italic> L. in New Zealand</article-title>. <source>Flavour Frag. J</source>. <year>1994</year>; <volume>9</volume>(<issue>6</issue>):<fpage>347</fpage>–<lpage>352</lpage>.</mixed-citation></ref><ref id="pone.0149332.ref004"><label>4</label><mixed-citation publication-type="journal"><name><surname>von Rudloff</surname><given-names>E</given-names></name>, <name><surname>Underhill</surname><given-names>EW</given-names></name>. <article-title>Gas-liquid chromatography of terpenes—XII: Seasonal variation in the volatile oil from <italic>Tanacetum vulgare</italic> L</article-title>. <source>Phytochemistry</source>. <year>1965</year>; <volume>4</volume>(<issue>1</issue>):<fpage>11</fpage>–<lpage>17</lpage>.</mixed-citation></ref><ref id="pone.0149332.ref005"><label>5</label><mixed-citation publication-type="journal"><name><surname>Voirin</surname><given-names>B</given-names></name>, <name><surname>Brun</surname><given-names>N</given-names></name>, <name><surname>Bayet</surname><given-names>C</given-names></name>. <article-title>Effects of day length on the monoterpene composition of leaves of <italic>Mentha x piperita</italic></article-title>. <source>Phytochemistry</source>. <year>1990</year>; <volume>29</volume>(<issue>3</issue>):<fpage>749</fpage>–<lpage>755</lpage>.</mixed-citation></ref><ref id="pone.0149332.ref006"><label>6</label><mixed-citation publication-type="journal"><name><surname>Klink</surname><given-names>CA</given-names></name>, <name><surname>Machado</surname><given-names>RB</given-names></name>. <article-title>Conservation of the Brazilian Cerrado</article-title>, <source>Conser. Biol</source>. <year>2005</year>;<volume>19</volume>(<issue>3</issue>):<fpage>707</fpage>–<lpage>713</lpage>.</mixed-citation></ref><ref id="pone.0149332.ref007"><label>7</label><mixed-citation publication-type="journal"><name><surname>Wang</surname><given-names>H</given-names></name>, <name><surname>Liu</surname><given-names>Y</given-names></name>, <name><surname>Wei</surname><given-names>S</given-names></name>, <name><surname>Yan</surname><given-names>Z</given-names></name>. <article-title>Comparative seasonal variation and chemical composition of essential oils from the leaves and stems of <italic>Schefflera heptaphylla</italic> using microwave-assisted and conventional hydrodistillation</article-title>. <source>Ind. Crop. Prod</source>. <year>2012</year>; <volume>36</volume>(<issue>1</issue>): <fpage>229</fpage>–<lpage>237</lpage>.</mixed-citation></ref><ref id="pone.0149332.ref008"><label>8</label><mixed-citation publication-type="journal"><name><surname>Coutinho</surname><given-names>LM</given-names></name>. <article-title>Savana concept</article-title>. <source>Acta bot. bras</source>. <year>2006</year>; <volume>20</volume>(<issue>1</issue>):<fpage>13</fpage>–<lpage>23</lpage>.</mixed-citation></ref><ref id="pone.0149332.ref009"><label>9</label><mixed-citation publication-type="journal"><name><surname>Almeida</surname><given-names>LFR</given-names></name>, <name><surname>Portella</surname><given-names>RO</given-names></name>, <name><surname>Facanali</surname><given-names>R</given-names></name>, <name><surname>Marques</surname><given-names>MOM</given-names></name>, <name><surname>Frei</surname><given-names>F</given-names></name>. <article-title>Dry and wet seasons set the phytochemical profile of the <italic>Copaifera langsdorffii</italic> Desf. essential oils</article-title>. <source>J. Essent. Oil. Res</source>. <year>2014</year>; <volume>26</volume>(<issue>4</issue>):<fpage>292</fpage>–<lpage>300</lpage>.</mixed-citation></ref><ref id="pone.0149332.ref010"><label>10</label><mixed-citation publication-type="journal"><name><surname>Bakkali</surname><given-names>F</given-names></name>, <name><surname>Averbeck</surname><given-names>S</given-names></name>, <name><surname>Averbeck</surname><given-names>D</given-names></name>, <name><surname>Idaomar</surname><given-names>M</given-names></name>. <article-title>Biological effects of essential oils–a review</article-title>. <source>Food Chem. Toxicol</source>. <year>2008</year>; <volume>46</volume>(<issue>2</issue>):<fpage>446</fpage>–<lpage>475</lpage>. <pub-id pub-id-type="pmid">17996351</pub-id></mixed-citation></ref><ref id="pone.0149332.ref011"><label>11</label><mixed-citation publication-type="journal"><name><surname>Michel</surname><given-names>CG</given-names></name>, <name><surname>Nesseem</surname><given-names>DI</given-names></name>, <name><surname>Ismail</surname><given-names>MF</given-names></name><article-title>. Anti-diabetic activity and stability study of the formulated leaf extract of <italic>Zizyphus spina-christi</italic> (L.) Willd with the influence of seasonal variation</article-title>, <source>J. Ethnopharmacol</source>. <year>2011</year>; <volume>133</volume>(<issue>1</issue>):<fpage>53</fpage>–<lpage>62</lpage>. <comment>doi: <ext-link ext-link-type="uri" xlink:href="http://dx.doi.org/10.1016/j.jep.2010.09.001">10.1016/j.jep.2010.09.001</ext-link></comment><pub-id pub-id-type="pmid">20833236</pub-id></mixed-citation></ref><ref id="pone.0149332.ref012"><label>12</label><mixed-citation publication-type="journal"><name><surname>Hussain</surname><given-names>AI</given-names></name>, <name><surname>Anwar</surname><given-names>F</given-names></name>, <name><surname>Sherazi</surname><given-names>STH</given-names></name>, <name><surname>Przybylski</surname><given-names>R</given-names></name>. <article-title>Chemical composition, antioxidant and antimicrobial activities of basil (<italic>Ocimum basilicum</italic>) essential oils depends on seasonal variations</article-title>, <source>Food Chem</source>. <year>2008</year>; <volume>108</volume>(<issue>3</issue>):<fpage>986</fpage>–<lpage>995</lpage>. <comment>doi: <ext-link ext-link-type="uri" xlink:href="http://dx.doi.org/10.1016/j.foodchem.2007.12.010">10.1016/j.foodchem.2007.12.010</ext-link></comment><pub-id pub-id-type="pmid">26065762</pub-id></mixed-citation></ref><ref id="pone.0149332.ref013"><label>13</label><mixed-citation publication-type="journal"><name><surname>Rodilla</surname><given-names>JM</given-names></name>, <name><surname>Tinoco</surname><given-names>MT</given-names></name>, <name><surname>Morais</surname><given-names>JC</given-names></name>, <name><surname>Gimenez</surname><given-names>C</given-names></name>, <name><surname>Cebrera</surname><given-names>R</given-names></name>, <name><surname>Martín-Benito</surname><given-names>D</given-names></name>, <etal>et al</etal><article-title><italic>Laurus novocanariensis</italic> essential oil: Seasonal variation and valorization</article-title>, <source>Biochem. Syst. Ecol</source>. <year>2008</year>; <volume>36</volume>(<issue>3</issue>):<fpage>167</fpage>–<lpage>176</lpage>.</mixed-citation></ref><ref id="pone.0149332.ref014"><label>14</label><mixed-citation publication-type="journal"><name><surname>Sartor</surname><given-names>T</given-names></name>, <name><surname>Xavier</surname><given-names>VB</given-names></name>, <name><surname>Falcão</surname><given-names>MA</given-names></name>, <name><surname>Mondin</surname><given-names>CA</given-names></name>, <name><surname>dos Santos</surname><given-names>MA</given-names></name>, <name><surname>Cassel</surname><given-names>E</given-names></name>, <etal>et al</etal><article-title>Seasonal changes in phenolic compounds and in the biological activities of <italic>Baccharis dentata</italic> (Vell.) G.M</article-title>. <source>Barroso. Ind. Crop. Prod</source>. <year>2013</year>; <volume>51</volume>:<fpage>355</fpage>–<lpage>359</lpage>.</mixed-citation></ref><ref id="pone.0149332.ref015"><label>15</label><mixed-citation publication-type="journal"><name><surname>Paolini</surname><given-names>J</given-names></name>, <name><surname>Barboni</surname><given-names>T</given-names></name>, <name><surname>Desjobert</surname><given-names>JM</given-names></name>, <name><surname>Djabou</surname><given-names>N</given-names></name>, <name><surname>Muselli</surname><given-names>A</given-names></name>, <name><surname>Costa</surname><given-names>J</given-names></name>. <article-title>Chemical composition, intraspecies variation and seasonal variation in essential oils of <italic>Calendula arvensis</italic> L.</article-title>, <source>Biochem. Syst. Ecol</source>. <year>2010</year>;<volume>38</volume>(<issue>5</issue>):<fpage>865</fpage>–<lpage>874</lpage>.</mixed-citation></ref><ref id="pone.0149332.ref016"><label>16</label><mixed-citation publication-type="journal"><name><surname>Telci</surname><given-names>I</given-names></name>, <name><surname>Kacar</surname><given-names>O</given-names></name>, <name><surname>Bayram</surname><given-names>E</given-names></name>, <name><surname>Arabaci</surname><given-names>O</given-names></name>, <name><surname>Demirtaş</surname><given-names>I</given-names></name>, <name><surname>Yilmaz</surname><given-names>G</given-names></name>, <etal>et al</etal><article-title>The effect of ecological conditions on yield and quality traits of selected peppermint (<italic>Mentha piperita</italic> L.) clones</article-title>. <source>Ind. Crop. Prod</source>. <year>2011</year>; <volume>34</volume>(<issue>1</issue>):<fpage>1193</fpage>–<lpage>1197</lpage>.</mixed-citation></ref><ref id="pone.0149332.ref017"><label>17</label><mixed-citation publication-type="journal"><name><surname>Kumar</surname><given-names>R</given-names></name>, <name><surname>Sharma</surname><given-names>S</given-names></name>, <name><surname>Sood</surname><given-names>S</given-names></name>, <name><surname>Agnihotri</surname><given-names>VK</given-names></name>, <name><surname>Singh</surname><given-names>B</given-names></name>. <article-title>Effect of diurnal variability and storage conditions on essential oil content and quality of damask rose (<italic>Rosa damascena</italic> Mill.) flowers in North Western Himalayas</article-title>. <source>Sci. Hortic</source>. <year>2013</year>; <volume>154</volume>:<fpage>102</fpage>–<lpage>108</lpage>.</mixed-citation></ref><ref id="pone.0149332.ref018"><label>18</label><mixed-citation publication-type="journal"><name><surname>Veiga Junior</surname><given-names>VF</given-names></name>, <name><surname>Pinto</surname><given-names>AC</given-names></name>. <article-title>The <italic>Copaifera</italic> L. Genus</article-title>. <source>Quím Nova</source>. <year>2002</year>; <volume>25</volume>(<issue>2</issue>):<fpage>273</fpage>–<lpage>286</lpage>.</mixed-citation></ref><ref id="pone.0149332.ref019"><label>19</label><mixed-citation publication-type="journal"><name><surname>Freitas</surname><given-names>CV</given-names></name>, <name><surname>Oliveira</surname><given-names>PE</given-names></name>. <article-title>Reproductive biology of <italic>Copaifera langsdorffii</italic> Desf. (Leguminosae, Caesalpinioideae)</article-title>. <source>Rev. Brasil. Bot</source>. <year>2002</year>; <volume>25</volume>(<issue>3</issue>):<fpage>311</fpage>–<lpage>321</lpage>.</mixed-citation></ref><ref id="pone.0149332.ref020"><label>20</label><mixed-citation publication-type="journal"><name><surname>Nascimento</surname><given-names>ME</given-names></name>, <name><surname>Zoghbi</surname><given-names>MGB</given-names></name>, <name><surname>Pinto</surname><given-names>JEBP</given-names></name>, <name><surname>Bertolucci</surname><given-names>SKV</given-names></name>. <article-title>Chemical variability of the volatiles of <italic>Copaifera langsdorffii</italic> growing wild in the Southeastern part of Brazil</article-title>. <source>Biochem. Syst. Ecol</source>. <year>2012</year>; <volume>43</volume>:<fpage>1</fpage>–<lpage>6</lpage>.</mixed-citation></ref><ref id="pone.0149332.ref021"><label>21</label><mixed-citation publication-type="journal"><name><surname>Leandro</surname><given-names>LM</given-names></name>, <name><surname>Vargas</surname><given-names>FS</given-names></name>, <name><surname>Barbosa</surname><given-names>PCS</given-names></name>, <name><surname>Neves</surname><given-names>JKO</given-names></name>, <name><surname>Silva</surname><given-names>JA</given-names></name>, <name><surname>Veiga-Junior</surname><given-names>VF</given-names></name>. <article-title>Chemistry and biological activities of terpenoids from copaiba (<italic>Copaifera spp</italic>.) oleoresins</article-title>. <source>Molecules</source>. <year>2012</year>; <volume>17</volume>(<issue>4</issue>):<fpage>3866</fpage>–<lpage>3889</lpage>. <comment>doi: <ext-link ext-link-type="uri" xlink:href="http://dx.doi.org/10.3390/molecules17043866">10.3390/molecules17043866</ext-link></comment><pub-id pub-id-type="pmid">22466849</pub-id></mixed-citation></ref><ref id="pone.0149332.ref022"><label>22</label><mixed-citation publication-type="journal"><name><surname>Gelmini</surname><given-names>F</given-names></name>, <name><surname>Beretta</surname><given-names>G</given-names></name>, <name><surname>Anselmi</surname><given-names>C</given-names></name>, <name><surname>Centini</surname><given-names>M</given-names></name>, <name><surname>Magni</surname><given-names>P</given-names></name>, <name><surname>Ruscica</surname><given-names>M</given-names></name>, <etal>et al</etal><article-title>GC–MS profiling of the phytochemical constituents of the oleoresin from <italic>Copaifera langsdorffii</italic> Desf. and a preliminary in vivo evaluation of its antipsoriatic effect</article-title>. <source>Int. J. Pharm</source>. <year>2013</year>; <volume>440</volume>(<issue>2</issue>): <fpage>170</fpage>–<lpage>178</lpage>. <comment>doi: <ext-link ext-link-type="uri" xlink:href="http://dx.doi.org/10.1016/j.ijpharm.2012.08.021">10.1016/j.ijpharm.2012.08.021</ext-link></comment><pub-id pub-id-type="pmid">22939967</pub-id></mixed-citation></ref><ref id="pone.0149332.ref023"><label>23</label><mixed-citation publication-type="journal"><name><surname>Ribeiro</surname><given-names>DA</given-names></name>, <name><surname>Oliveira</surname><given-names>LGS</given-names></name>, <name><surname>Macêdo</surname><given-names>DG</given-names></name>, <name><surname>Menezes</surname><given-names>IRA</given-names></name>, <name><surname>Costa</surname><given-names>JGM</given-names></name>, <name><surname>Silva</surname><given-names>MAP</given-names></name>, <etal>et al</etal><article-title>Promising medicinal plants for bioprospection in a Cerrado area of Chapada do Araripe, Northeastern Brazil</article-title>. <source>J. Ethnopharmacol</source>. <year>2014</year>; <volume>155</volume>(<issue>3</issue>):<fpage>1522</fpage>–<lpage>1533</lpage>. <comment>doi: <ext-link ext-link-type="uri" xlink:href="http://dx.doi.org/10.1016/j.jep.2014.07.042">10.1016/j.jep.2014.07.042</ext-link></comment><pub-id pub-id-type="pmid">25086410</pub-id></mixed-citation></ref><ref id="pone.0149332.ref024"><label>24</label><mixed-citation publication-type="book"><name><surname>Oliveira</surname><given-names>PS</given-names></name>, <name><surname>Marquis</surname><given-names>RJ</given-names></name>. <chapter-title>The cerrados of Brazil: ecology and natural history of a neotropical savanna</chapter-title><publisher-name>Columbia University Press</publisher-name>, <edition>1st Edn</edition>, <publisher-loc>New York</publisher-loc>; <year>2002</year> p. <fpage>289</fpage>.</mixed-citation></ref><ref id="pone.0149332.ref025"><label>25</label><mixed-citation publication-type="book"><name><surname>Ribeiro</surname><given-names>JF</given-names></name>, <name><surname>Waler</surname><given-names>BMT</given-names></name>. <chapter-title>Fitofisionomias do bioma Cerrado</chapter-title> In: <name><surname>Sano</surname><given-names>S.M.</given-names></name>, <name><surname>Almeida</surname><given-names>S.P.</given-names></name> (eds.) <source>Cerrado: ambiente e flora</source>. <publisher-loc>Planaltina</publisher-loc>: <publisher-name>Embrapa Cerrados</publisher-name>; <year>1998</year> pp. <fpage>89</fpage>–<lpage>168</lpage>.</mixed-citation></ref><ref id="pone.0149332.ref026"><label>26</label><mixed-citation publication-type="journal"><name><surname>Silva</surname><given-names>EF</given-names></name>, <name><surname>Santos</surname><given-names>TRR</given-names></name>, <name><surname>Fernandes-Bulhão</surname><given-names>C</given-names></name>. <article-title>Levantamento florístico das lianas lenhosas, arbustos e subarbustos do Cerrado do Parque do Bacaba, Nova Xavantina–MT</article-title>. <source>R. Bras. Bioci</source>. <year>2007</year>; <volume>5</volume>(<issue>2</issue>):<fpage>948</fpage>–<lpage>950</lpage>.</mixed-citation></ref><ref id="pone.0149332.ref027"><label>27</label><mixed-citation publication-type="book"><name><surname>McLafferty</surname><given-names>FW</given-names></name>, <name><surname>Stauffer</surname><given-names>D</given-names></name>. <source>The Wiley / NBS Registry of Mass Spectral Data</source>. <publisher-name>John Wiley Sons</publisher-name>, <publisher-loc>New York</publisher-loc>; <year>1989</year>.</mixed-citation></ref><ref id="pone.0149332.ref028"><label>28</label><mixed-citation publication-type="book"><name><surname>Adams</surname><given-names>RP</given-names></name>. <chapter-title>Identification of essential oil components by gas cromatography/mass spectroscopy</chapter-title>, <edition>4th ed.</edition>; <publisher-name>Allured Publishing</publisher-name>: <publisher-loc>Carol Stream, IL, USA</publisher-loc>; <year>2007</year>.</mixed-citation></ref><ref id="pone.0149332.ref029"><label>29</label><mixed-citation publication-type="journal"><name><surname>Van Den Dool</surname><given-names>H</given-names></name>, <name><surname>Kratz</surname><given-names>DJ</given-names></name>. <article-title>A generalization of the retention index system including linear temperature programmed gas—liquid parttition chromatography</article-title>. <source>J. Cromatog. A</source>. <year>1963</year>; <volume>11</volume>: <fpage>463</fpage>–<lpage>467</lpage>.</mixed-citation></ref><ref id="pone.0149332.ref030"><label>30</label><mixed-citation publication-type="journal"><name><surname>Gramosa</surname><given-names>NV</given-names></name>, <name><surname>Silveira</surname><given-names>ER</given-names></name>. <article-title>Volatile Constituents of <italic>Copaifera langsdorffii</italic> from the Brazilian Northeast</article-title>. <source>J. Essent. Oil Res</source>. <year>2005</year>; <volume>17</volume>(<issue>2</issue>):<fpage>130</fpage>–<lpage>132</lpage>.</mixed-citation></ref><ref id="pone.0149332.ref031"><label>31</label><mixed-citation publication-type="journal"><name><surname>Chen</surname><given-names>F</given-names></name>, <name><surname>Al-Ahmad</surname><given-names>H</given-names></name>, <name><surname>Joyce</surname><given-names>B</given-names></name>, <name><surname>Zhao</surname><given-names>N</given-names></name>, <name><surname>Köllner</surname><given-names>TG</given-names></name>, <name><surname>Degenhardt</surname><given-names>J</given-names></name>, <etal>et al</etal><article-title>Within-plant distribution and emission of sesquiterpenes from <italic>Copaifera officinalis</italic></article-title>. <source>Plant Physiol. Bioch</source>. <year>2009</year>; <volume>47</volume>(<issue>11–12</issue>): <fpage>1017</fpage>–<lpage>1023</lpage>.</mixed-citation></ref><ref id="pone.0149332.ref032"><label>32</label><mixed-citation publication-type="journal"><name><surname>Cascon</surname><given-names>V</given-names></name>, <name><surname>Gilbert</surname><given-names>B</given-names></name>. <article-title>Characterizaton of the chemical composition of oleoresins of <italic>Copaifera guianensis</italic> Desf., <italic>Copaifera duckei</italic> Dwyer and <italic>Copaifera multijuga</italic> Hayne</article-title>. <source>Phytochemistry</source>. <year>2000</year>; <volume>55</volume>(<issue>7</issue>):<fpage>773</fpage>–<lpage>778</lpage>. <pub-id pub-id-type="pmid">11190394</pub-id></mixed-citation></ref><ref id="pone.0149332.ref033"><label>33</label><mixed-citation publication-type="journal"><name><surname>Veiga</surname><given-names>VF</given-names></name>, <name><surname>Pinto</surname><given-names>AC</given-names></name>, <name><surname>Lima</surname><given-names>HC</given-names></name>. <article-title>The Essential Oil Composition of <italic>Copaifera trapezifolia</italic> Hayne Leaves</article-title>. <source>J. Essent. Oil Res</source>. <year>2009</year>; <volume>18</volume>(<issue>4</issue>):<fpage>430</fpage>–<lpage>431</lpage>.</mixed-citation></ref><ref id="pone.0149332.ref034"><label>34</label><mixed-citation publication-type="journal"><name><surname>Zoghbi</surname><given-names>MGB</given-names></name>, <name><surname>Martins-da-Silva</surname><given-names>RCV</given-names></name>, <name><surname>Trigo</surname><given-names>JR</given-names></name>. <article-title>Volatiles of Oleoresins of <italic>Copaifera paupera</italic> (Herzog) Dwyer <italic>C</italic>. <italic>piresii</italic> Dwyer and <italic>C</italic>. <italic>pubiflora</italic> Benth. (Leguminosae)</article-title>. <source>J. Essent. Oil Res</source>. <year>2009</year>; <volume>21</volume>(<issue>5</issue>): <fpage>403</fpage>–<lpage>404</lpage>.</mixed-citation></ref><ref id="pone.0149332.ref035"><label>35</label><mixed-citation publication-type="journal"><name><surname>Sangwan</surname><given-names>NS</given-names></name>, <name><surname>Farooqi</surname><given-names>AHA</given-names></name>, <name><surname>Shabih</surname><given-names>F</given-names></name>, <name><surname>Sangwan</surname><given-names>RS</given-names></name>. <article-title>Regulation of essential oil production in plants</article-title>. <source>Plant Growth Regul</source>. <year>2001</year>; <volume>34</volume>(<issue>1</issue>):<fpage>3</fpage>–<lpage>21</lpage>.</mixed-citation></ref><ref id="pone.0149332.ref036"><label>36</label><mixed-citation publication-type="journal"><name><surname>Gawronska</surname><given-names>K</given-names></name>, <name><surname>Romanowska</surname><given-names>E</given-names></name>, <name><surname>Miszalski</surname><given-names>Z</given-names></name>, <name><surname>Niewiadomska</surname><given-names>E</given-names></name>. <article-title>Limitation of C3–CAM shift in the common ice plant under high irradiance</article-title>. <source>J. Plant Physiol</source>. <year>2013</year>; <volume>170</volume>(<issue>2</issue>):<fpage>129</fpage>–<lpage>135</lpage>. <comment>doi: <ext-link ext-link-type="uri" xlink:href="http://dx.doi.org/10.1016/j.jplph.2012.09.019">10.1016/j.jplph.2012.09.019</ext-link></comment><pub-id pub-id-type="pmid">23253482</pub-id></mixed-citation></ref><ref id="pone.0149332.ref037"><label>37</label><mixed-citation publication-type="journal"><name><surname>Rodrigues</surname><given-names>TM</given-names></name>, <name><surname>Buarque</surname><given-names>PFSM</given-names></name>, <name><surname>Coneglian</surname><given-names>AG</given-names></name>, <name><surname>Reis</surname><given-names>DC</given-names></name>. <article-title>Light and temperature induce variations in the density and ultrastructure of the secretory spaces in the diesel-tree (<italic>Copaifera langsdorffii</italic> Desf.—Leguminosae)</article-title>. <source>Trees</source>. <year>2014</year>; <volume>28</volume>(<issue>2</issue>):<fpage>613</fpage>–<lpage>623</lpage>.</mixed-citation></ref><ref id="pone.0149332.ref038"><label>38</label><mixed-citation publication-type="journal"><name><surname>Vidović</surname><given-names>M</given-names></name>, <name><surname>Morina</surname><given-names>F</given-names></name>, <name><surname>Milić</surname><given-names>S</given-names></name>, <name><surname>Albert</surname><given-names>A</given-names></name>, <name><surname>Zechmann</surname><given-names>B</given-names></name>, <name><surname>Tosti</surname><given-names>T</given-names></name>, <etal>et al</etal><article-title>Carbon allocation from source to sink leaf tissue in relation to flavonoid biosynthesis in variegated Pelargonium zonale under UV-B radiation and high PAR intensity</article-title>. <source>Plant Physiol. Biochem</source>. <year>2014</year>; <volume>93</volume>:<fpage>44</fpage>–<lpage>55</lpage>.<pub-id pub-id-type="pmid">25661975</pub-id></mixed-citation></ref><ref id="pone.0149332.ref039"><label>39</label><mixed-citation publication-type="journal"><name><surname>Helmig</surname><given-names>D</given-names></name>, <name><surname>Ortega</surname><given-names>J</given-names></name>, <name><surname>Guenther</surname><given-names>A</given-names></name>, <name><surname>Herrick</surname><given-names>JD</given-names></name>, <name><surname>Geron</surname><given-names>C</given-names></name>. <article-title>Sesquiterpene emissions from loblolly pine and their potential contribution to biogenic aerosol formation in the Southeastern US</article-title>. <source>Atmos. Environ</source>. <year>2006</year>; <volume>40</volume>(<issue>22</issue>):<fpage>4150</fpage>–<lpage>4157</lpage>.</mixed-citation></ref><ref id="pone.0149332.ref040"><label>40</label><mixed-citation publication-type="journal"><name><surname>Duhl</surname><given-names>TR</given-names></name>, <name><surname>Helmig</surname><given-names>D</given-names></name>, <name><surname>Guenther</surname><given-names>A</given-names></name>. <article-title>Sesquiterpene emissions from vegetation: a review</article-title>. <source>Biogeosciences</source>. <year>2008</year>; <volume>5</volume>(<issue>3</issue>):<fpage>761</fpage>–<lpage>777</lpage>.</mixed-citation></ref><ref id="pone.0149332.ref041"><label>41</label><mixed-citation publication-type="journal"><name><surname>Ribeiro</surname><given-names>AF</given-names></name>, <name><surname>Andrade</surname><given-names>EHA</given-names></name>, <name><surname>Salimena</surname><given-names>FRG</given-names></name>, <name><surname>Maia</surname><given-names>JGS</given-names></name>. <article-title>Circadian and seasonal study of the cinnamate chemotype from Lippia origanoides Kunth</article-title>. <source>Biochem. Syst. Ecol</source>. <year>2014</year>; <volume>55</volume>:<fpage>249</fpage>–<lpage>259</lpage>.</mixed-citation></ref><ref id="pone.0149332.ref042"><label>42</label><mixed-citation publication-type="journal"><name><surname>Asghari</surname><given-names>G</given-names></name>, <name><surname>Gholamali</surname><given-names>H</given-names></name>, <name><surname>Mahmoudi</surname><given-names>Z</given-names></name>, <name><surname>Asghari</surname><given-names>M</given-names></name>. <article-title>Diurnal Variation of Essential of the Oil Components of <italic>Pycnocycla spinosa</italic> Decne. ex Boiss, Jundishapur</article-title>. <source>J Nat Pharm Prod</source>. <year>2014</year>; <volume>9</volume>(<issue>1</issue>):<fpage>35</fpage>–<lpage>38</lpage>.</mixed-citation></ref><ref id="pone.0149332.ref043"><label>43</label><mixed-citation publication-type="journal"><name><surname>Christensen</surname><given-names>CS</given-names></name>, <name><surname>Hummelshøj</surname><given-names>P</given-names></name>, <name><surname>Jensen</surname><given-names>NO</given-names></name>, <name><surname>Larsen</surname><given-names>B</given-names></name>, <name><surname>Lohse</surname><given-names>C</given-names></name>, <name><surname>Pilegaard</surname><given-names>K</given-names></name>, <etal>et al</etal><article-title>Determination of the terpene flux from orange species and Norway spruce by relaxed eddy accumulation</article-title>. <source>Atmos. Environ</source>. <year>2000</year>; <volume>34</volume>(<issue>19</issue>):<fpage>3057</fpage>–<lpage>3067</lpage>.</mixed-citation></ref><ref id="pone.0149332.ref044"><label>44</label><mixed-citation publication-type="journal"><name><surname>Fuentes</surname><given-names>JD</given-names></name>, <name><surname>Wang</surname><given-names>D</given-names></name>, <name><surname>Neumann</surname><given-names>HH</given-names></name>, <name><surname>Gillespie</surname><given-names>TJ</given-names></name>, <name><surname>Den Hartog</surname><given-names>G</given-names></name>, <etal>et al</etal><article-title>Ambient biogenic hydrocarbons and isoprene emissions from a mixed deciduous forest</article-title>. <source>J. Atmos. Chem</source>. <year>1996</year>; <volume>25</volume>(<issue>1</issue>):<fpage>67</fpage>–<lpage>95</lpage>.</mixed-citation></ref><ref id="pone.0149332.ref045"><label>45</label><mixed-citation publication-type="journal"><name><surname>Vallat</surname><given-names>A</given-names></name>, <name><surname>Gu</surname><given-names>H</given-names></name>, <name><surname>Dorn</surname><given-names>S</given-names></name>. <article-title>How rainfall, relative humidity and temperature influence volatile emissions from apple trees in situ</article-title>. <source>Phytochemistry</source>. <year>2005</year>; <volume>66</volume>(<issue>13</issue>):<fpage>1540</fpage>–<lpage>1550</lpage>. <pub-id pub-id-type="pmid">15949824</pub-id></mixed-citation></ref><ref id="pone.0149332.ref046"><label>46</label><mixed-citation publication-type="journal"><name><surname>Angelopoulou</surname><given-names>D</given-names></name>, <name><surname>Demetzo</surname><given-names>C</given-names></name>, <name><surname>Perdetzoglou</surname><given-names>D</given-names></name>. <article-title>Diurnal and seasonal variation of the essential oil labdanes and clerodanes from <italic>Cistus monspeliensis</italic> L. leaves</article-title>. <source>Biochem. Syst. Ecol</source>. <year>2002</year>; <volume>30</volume>(<issue>3</issue>):<fpage>129</fpage>–<lpage>203</lpage>.</mixed-citation></ref><ref id="pone.0149332.ref047"><label>47</label><mixed-citation publication-type="journal"><name><surname>Toncer</surname><given-names>O</given-names></name>, <name><surname>Karaman</surname><given-names>S</given-names></name>, <name><surname>Kizil</surname><given-names>S</given-names></name>, <name><surname>Diraz</surname><given-names>E</given-names></name>. <article-title>Changes in essential oil composition of oregano (<italic>Origanum onites</italic> L.) due to diurnal variations at different development stages</article-title>. <source>Not. Bot. Hort. Agrobot. Cluj</source>. <year>2009</year>; <volume>37</volume>(<issue>2</issue>):<fpage>177</fpage>–<lpage>181</lpage>.</mixed-citation></ref><ref id="pone.0149332.ref048"><label>48</label><mixed-citation publication-type="journal"><name><surname>Del-Vechio-Vieira</surname><given-names>G</given-names></name>, <name><surname>Sousa</surname><given-names>OV</given-names></name>, <name><surname>Yamamoto</surname><given-names>CH</given-names></name>, <name><surname>Kaplan</surname><given-names>MAC</given-names></name>. <article-title>Chemical Composition and Antimicrobial Activity of the Essential Oils of <italic>Ageratum fastigiatum</italic> (Asteraceae)</article-title>. <source>Rec. Nat. Prod</source>. <year>2009</year>; <volume>3</volume>(<issue>1</issue>):<fpage>52</fpage>–<lpage>57</lpage>.</mixed-citation></ref><ref id="pone.0149332.ref049"><label>49</label><mixed-citation publication-type="journal"><name><surname>Nagappan</surname><given-names>T</given-names></name>, <name><surname>Ramasamy</surname><given-names>P</given-names></name>, <name><surname>Wahid</surname><given-names>MEA</given-names></name>, <name><surname>Segaran</surname><given-names>TC</given-names></name>, <name><surname>Vairappan</surname><given-names>CS</given-names></name>. <article-title>Biological activity of Carbazole alkaloids and essential oil of <italic>Murraya koenigii</italic> against antibiotic resistant microbes and cancer cell lines</article-title>. <source>Molecules</source><year>2011</year>; <volume>16</volume>(<issue>11</issue>):<fpage>9651</fpage>–<lpage>9664</lpage>. <comment>doi: <ext-link ext-link-type="uri" xlink:href="http://dx.doi.org/10.3390/molecules16119651">10.3390/molecules16119651</ext-link></comment><pub-id pub-id-type="pmid">22105714</pub-id></mixed-citation></ref><ref id="pone.0149332.ref050"><label>50</label><mixed-citation publication-type="journal"><name><surname>Kobaisy</surname><given-names>M</given-names></name>, <name><surname>Tellez</surname><given-names>MR</given-names></name>, <name><surname>Dayan</surname><given-names>FE</given-names></name>, <name><surname>Duke</surname><given-names>SO</given-names></name>. <article-title>Phytotoxicity and volatile constituents from leaves of <italic>Callicarpa japonica</italic> Thunb</article-title>. <source>Phytochem</source>. <year>2002</year>; <volume>61</volume>(<issue>1</issue>):<fpage>37</fpage>–<lpage>40</lpage>.</mixed-citation></ref><ref id="pone.0149332.ref051"><label>51</label><mixed-citation publication-type="journal"><name><surname>Rigano</surname><given-names>D</given-names></name>, <name><surname>Arnold</surname><given-names>NA</given-names></name>, <name><surname>Conforti</surname><given-names>F</given-names></name>, <name><surname>Menichini</surname><given-names>F</given-names></name>, <name><surname>Formisano</surname><given-names>C</given-names></name>, <name><surname>Piozzi</surname><given-names>F</given-names></name>, <etal>et al</etal><article-title>Characterisation of the essential oil of Nepeta glomerata Montbret et Aucher ex Bentham from Lebanon and its biological activities</article-title>. <source>Nat. Prod. Res</source>. <year>2011</year>; <volume>25</volume>(<issue>6</issue>):<fpage>614</fpage>–<lpage>626</lpage>. <comment>doi: <ext-link ext-link-type="uri" xlink:href="http://dx.doi.org/10.1080/14786419.2010.488623">10.1080/14786419.2010.488623</ext-link></comment><pub-id pub-id-type="pmid">21409723</pub-id></mixed-citation></ref><ref id="pone.0149332.ref052"><label>52</label><mixed-citation publication-type="journal"><name><surname>Küçükbay</surname><given-names>FZ</given-names></name>, <name><surname>Kuyumcu</surname><given-names>E</given-names></name>, <name><surname>Bilenler</surname><given-names>T</given-names></name>, <name><surname>Yildiz</surname><given-names>B</given-names></name>. <article-title>Chemical composition and antimicrobial activity of essential oil of Achillea cretica L. (Asteraceae) from Turkey</article-title>. <source>Nat. Prod. Res</source>. <year>2012</year>; <volume>26</volume>(<issue>18</issue>):<fpage>1668</fpage>–<lpage>1675</lpage>. <comment>doi: <ext-link ext-link-type="uri" xlink:href="http://dx.doi.org/10.1080/14786419.2011.599808">10.1080/14786419.2011.599808</ext-link></comment><pub-id pub-id-type="pmid">21988483</pub-id></mixed-citation></ref></ref-list></back></pmc></record>Pour manipuler ce document sous Unix (Dilib)
EXPLOR_STEP=$WICRI_ROOT/Wicri/Bois/explor/OrangerV1/Data/Pmc/Corpus
HfdSelect -h $EXPLOR_STEP/biblio.hfd -nk 000375 | SxmlIndent | more
Ou
HfdSelect -h $EXPLOR_AREA/Data/Pmc/Corpus/biblio.hfd -nk 000375 | SxmlIndent | more
Pour mettre un lien sur cette page dans le réseau Wicri
{{Explor lien
|wiki= Wicri/Bois
|area= OrangerV1
|flux= Pmc
|étape= Corpus
|type= RBID
|clé= PMC:4757570
|texte= Non-Oxygenated Sesquiterpenes in the Essential Oil of Copaifera langsdorffii Desf. Increase during the Day in the Dry Season
}}
Pour générer des pages wiki
HfdIndexSelect -h $EXPLOR_AREA/Data/Pmc/Corpus/RBID.i -Sk "pubmed:26886431" \
| HfdSelect -Kh $EXPLOR_AREA/Data/Pmc/Corpus/biblio.hfd \
| NlmPubMed2Wicri -a OrangerV1
| This area was generated with Dilib version V0.6.25. |  |