Isolation, Structure Elucidation, and Antiproliferative Activity of Butanolides and Lignan Glycosides from the Fruit of Hernandia nymphaeifolia
Identifieur interne : 000708 ( Main/Exploration ); précédent : 000707; suivant : 000709Isolation, Structure Elucidation, and Antiproliferative Activity of Butanolides and Lignan Glycosides from the Fruit of Hernandia nymphaeifolia
Auteurs : Simayijiang Aimaiti ; Yohei Saito ; Shuichi Fukuyoshi ; Masuo Goto ; Katsunori Miyake ; David J. Newman ; Barry R. O Eefe [États-Unis] ; Kuo-Hsiung Lee [Taïwan] ; Kyoko Nakagawa-GotoSource :
- Molecules [ 1420-3049 ] ; 2019.
Abstract
Seven new butanolides, peltanolides A–G (
Url:
DOI: 10.3390/molecules24214005
PubMed: 31694283
PubMed Central: 6864620
Affiliations:
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<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Isolation, Structure Elucidation, and Antiproliferative Activity of Butanolides and Lignan Glycosides from the Fruit of <italic>Hernandia nymphaeifolia</italic></title><author><name sortKey="Aimaiti, Simayijiang" sort="Aimaiti, Simayijiang" uniqKey="Aimaiti S" first="Simayijiang" last="Aimaiti">Simayijiang Aimaiti</name><affiliation><nlm:aff id="af1-molecules-24-04005">School of Pharmaceutical Sciences, College of Medical, Pharmaceutical and Health Sciences, Kanazawa University, Kanazawa 920-1192, Japan;<email>ismayil507@stu.kanazawa-u.ac.jp</email> (S.A.);<email>saito-y@staff.kanazawa-u.ac.jp</email> (Y.S.);<email>fukuyosi@p.kanazawa-u.ac.jp</email> (S.F.)</nlm:aff></affiliation></author><author><name sortKey="Saito, Yohei" sort="Saito, Yohei" uniqKey="Saito Y" first="Yohei" last="Saito">Yohei Saito</name><affiliation><nlm:aff id="af1-molecules-24-04005">School of Pharmaceutical Sciences, College of Medical, Pharmaceutical and Health Sciences, Kanazawa University, Kanazawa 920-1192, Japan;<email>ismayil507@stu.kanazawa-u.ac.jp</email> (S.A.);<email>saito-y@staff.kanazawa-u.ac.jp</email> (Y.S.);<email>fukuyosi@p.kanazawa-u.ac.jp</email> (S.F.)</nlm:aff></affiliation></author><author><name sortKey="Fukuyoshi, Shuichi" sort="Fukuyoshi, Shuichi" uniqKey="Fukuyoshi S" first="Shuichi" last="Fukuyoshi">Shuichi Fukuyoshi</name><affiliation><nlm:aff id="af1-molecules-24-04005">School of Pharmaceutical Sciences, College of Medical, Pharmaceutical and Health Sciences, Kanazawa University, Kanazawa 920-1192, Japan;<email>ismayil507@stu.kanazawa-u.ac.jp</email> (S.A.);<email>saito-y@staff.kanazawa-u.ac.jp</email> (Y.S.);<email>fukuyosi@p.kanazawa-u.ac.jp</email> (S.F.)</nlm:aff></affiliation></author><author><name sortKey="Goto, Masuo" sort="Goto, Masuo" uniqKey="Goto M" first="Masuo" last="Goto">Masuo Goto</name><affiliation><nlm:aff id="af2-molecules-24-04005">Natural Products Research Laboratories, UNC Eshelman School of Pharmacy, University of North Carolina at Chapel Hill, Chapel Hill, NC 27599-7568, USA;<email>goto@med.unc.edu</email> (M.G.);<email>khlee@unc.edu</email> (K.-H.L.)</nlm:aff></affiliation></author><author><name sortKey="Miyake, Katsunori" sort="Miyake, Katsunori" uniqKey="Miyake K" first="Katsunori" last="Miyake">Katsunori Miyake</name><affiliation><nlm:aff id="af3-molecules-24-04005">Tokyo University of Pharmacy and Life Sciences, Hachioji, Tokyo 192-0392, Japan;<email>miyake@toyaku.ac.jp</email></nlm:aff></affiliation></author><author><name sortKey="Newman, David J" sort="Newman, David J" uniqKey="Newman D" first="David J." last="Newman">David J. Newman</name><affiliation><nlm:aff id="af4-molecules-24-04005">NIH Special Volunteer, Wayne, PA 19087, USA;<email>newmand@mail.nih.gov</email></nlm:aff></affiliation></author><author><name sortKey="O Eefe, Barry R" sort="O Eefe, Barry R" uniqKey="O Eefe B" first="Barry R." last="O Eefe">Barry R. O Eefe</name><affiliation><nlm:aff id="af5-molecules-24-04005">Natural Products Branch, Developmental Therapeutics Program, Division of Cancer Treatment and Diagnosis, National Cancer Institute, NCI at Frederick, Frederick, MD 21702-1201, USA;<email>okeefeba@mail.nih.gov</email></nlm:aff></affiliation><affiliation wicri:level="1"><nlm:aff id="af6-molecules-24-04005">Molecular Targets Program, Center for Cancer Research, National Cancer Institute, NCI at Frederick, Frederick, MD 21702-1201, USA</nlm:aff><country xml:lang="fr">États-Unis</country><wicri:regionArea>Molecular Targets Program, Center for Cancer Research, National Cancer Institute, NCI at Frederick, Frederick, MD 21702-1201</wicri:regionArea><wicri:noRegion>MD 21702-1201</wicri:noRegion></affiliation></author><author><name sortKey="Lee, Kuo Hsiung" sort="Lee, Kuo Hsiung" uniqKey="Lee K" first="Kuo-Hsiung" last="Lee">Kuo-Hsiung Lee</name><affiliation><nlm:aff id="af2-molecules-24-04005">Natural Products Research Laboratories, UNC Eshelman School of Pharmacy, University of North Carolina at Chapel Hill, Chapel Hill, NC 27599-7568, USA;<email>goto@med.unc.edu</email> (M.G.);<email>khlee@unc.edu</email> (K.-H.L.)</nlm:aff></affiliation><affiliation wicri:level="1"><nlm:aff id="af7-molecules-24-04005">Chinese Medicine Research and Development Center, China Medical University and Hospital, Taichung 40447, Taiwan</nlm:aff><country xml:lang="fr">Taïwan</country><wicri:regionArea>Chinese Medicine Research and Development Center, China Medical University and Hospital, Taichung 40447</wicri:regionArea><wicri:noRegion>Taichung 40447</wicri:noRegion></affiliation></author><author><name sortKey="Nakagawa Goto, Kyoko" sort="Nakagawa Goto, Kyoko" uniqKey="Nakagawa Goto K" first="Kyoko" last="Nakagawa-Goto">Kyoko Nakagawa-Goto</name><affiliation><nlm:aff id="af1-molecules-24-04005">School of Pharmaceutical Sciences, College of Medical, Pharmaceutical and Health Sciences, Kanazawa University, Kanazawa 920-1192, Japan;<email>ismayil507@stu.kanazawa-u.ac.jp</email> (S.A.);<email>saito-y@staff.kanazawa-u.ac.jp</email> (Y.S.);<email>fukuyosi@p.kanazawa-u.ac.jp</email> (S.F.)</nlm:aff></affiliation><affiliation><nlm:aff id="af2-molecules-24-04005">Natural Products Research Laboratories, UNC Eshelman School of Pharmacy, University of North Carolina at Chapel Hill, Chapel Hill, NC 27599-7568, USA;<email>goto@med.unc.edu</email> (M.G.);<email>khlee@unc.edu</email> (K.-H.L.)</nlm:aff></affiliation></author></titleStmt><publicationStmt><idno type="wicri:source">PMC</idno><idno type="pmid">31694283</idno><idno type="pmc">6864620</idno><idno type="url">http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6864620</idno><idno type="RBID">PMC:6864620</idno><idno type="doi">10.3390/molecules24214005</idno><date when="2019">2019</date><idno type="wicri:Area/Pmc/Corpus">000722</idno><idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Corpus" wicri:corpus="PMC">000722</idno><idno 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Aimaiti</name><affiliation><nlm:aff id="af1-molecules-24-04005">School of Pharmaceutical Sciences, College of Medical, Pharmaceutical and Health Sciences, Kanazawa University, Kanazawa 920-1192, Japan;<email>ismayil507@stu.kanazawa-u.ac.jp</email> (S.A.);<email>saito-y@staff.kanazawa-u.ac.jp</email> (Y.S.);<email>fukuyosi@p.kanazawa-u.ac.jp</email> (S.F.)</nlm:aff></affiliation></author><author><name sortKey="Saito, Yohei" sort="Saito, Yohei" uniqKey="Saito Y" first="Yohei" last="Saito">Yohei Saito</name><affiliation><nlm:aff id="af1-molecules-24-04005">School of Pharmaceutical Sciences, College of Medical, Pharmaceutical and Health Sciences, Kanazawa University, Kanazawa 920-1192, Japan;<email>ismayil507@stu.kanazawa-u.ac.jp</email> (S.A.);<email>saito-y@staff.kanazawa-u.ac.jp</email> (Y.S.);<email>fukuyosi@p.kanazawa-u.ac.jp</email> (S.F.)</nlm:aff></affiliation></author><author><name sortKey="Fukuyoshi, Shuichi" sort="Fukuyoshi, Shuichi" uniqKey="Fukuyoshi S" first="Shuichi" last="Fukuyoshi">Shuichi Fukuyoshi</name><affiliation><nlm:aff id="af1-molecules-24-04005">School of Pharmaceutical Sciences, College of Medical, Pharmaceutical and Health Sciences, Kanazawa University, Kanazawa 920-1192, Japan;<email>ismayil507@stu.kanazawa-u.ac.jp</email> (S.A.);<email>saito-y@staff.kanazawa-u.ac.jp</email> (Y.S.);<email>fukuyosi@p.kanazawa-u.ac.jp</email> (S.F.)</nlm:aff></affiliation></author><author><name sortKey="Goto, Masuo" sort="Goto, Masuo" uniqKey="Goto M" first="Masuo" last="Goto">Masuo Goto</name><affiliation><nlm:aff id="af2-molecules-24-04005">Natural Products Research Laboratories, UNC Eshelman School of Pharmacy, University of North Carolina at Chapel Hill, Chapel Hill, NC 27599-7568, USA;<email>goto@med.unc.edu</email> (M.G.);<email>khlee@unc.edu</email> (K.-H.L.)</nlm:aff></affiliation></author><author><name sortKey="Miyake, Katsunori" sort="Miyake, Katsunori" uniqKey="Miyake K" first="Katsunori" last="Miyake">Katsunori Miyake</name><affiliation><nlm:aff id="af3-molecules-24-04005">Tokyo University of Pharmacy and Life Sciences, Hachioji, Tokyo 192-0392, Japan;<email>miyake@toyaku.ac.jp</email></nlm:aff></affiliation></author><author><name sortKey="Newman, David J" sort="Newman, David J" uniqKey="Newman D" first="David J." last="Newman">David J. Newman</name><affiliation><nlm:aff id="af4-molecules-24-04005">NIH Special Volunteer, Wayne, PA 19087, USA;<email>newmand@mail.nih.gov</email></nlm:aff></affiliation></author><author><name sortKey="O Eefe, Barry R" sort="O Eefe, Barry R" uniqKey="O Eefe B" first="Barry R." last="O Eefe">Barry R. O Eefe</name><affiliation><nlm:aff id="af5-molecules-24-04005">Natural Products Branch, Developmental Therapeutics Program, Division of Cancer Treatment and Diagnosis, National Cancer Institute, NCI at Frederick, Frederick, MD 21702-1201, USA;<email>okeefeba@mail.nih.gov</email></nlm:aff></affiliation><affiliation wicri:level="1"><nlm:aff id="af6-molecules-24-04005">Molecular Targets Program, Center for Cancer Research, National Cancer Institute, NCI at Frederick, Frederick, MD 21702-1201, USA</nlm:aff><country xml:lang="fr">États-Unis</country><wicri:regionArea>Molecular Targets Program, Center for Cancer Research, National Cancer Institute, NCI at Frederick, Frederick, MD 21702-1201</wicri:regionArea><wicri:noRegion>MD 21702-1201</wicri:noRegion></affiliation></author><author><name sortKey="Lee, Kuo Hsiung" sort="Lee, Kuo Hsiung" uniqKey="Lee K" first="Kuo-Hsiung" last="Lee">Kuo-Hsiung Lee</name><affiliation><nlm:aff id="af2-molecules-24-04005">Natural Products Research Laboratories, UNC Eshelman School of Pharmacy, University of North Carolina at Chapel Hill, Chapel Hill, NC 27599-7568, USA;<email>goto@med.unc.edu</email> (M.G.);<email>khlee@unc.edu</email> (K.-H.L.)</nlm:aff></affiliation><affiliation wicri:level="1"><nlm:aff id="af7-molecules-24-04005">Chinese Medicine Research and Development Center, China Medical University and Hospital, Taichung 40447, Taiwan</nlm:aff><country xml:lang="fr">Taïwan</country><wicri:regionArea>Chinese Medicine Research and Development Center, China Medical University and Hospital, Taichung 40447</wicri:regionArea><wicri:noRegion>Taichung 40447</wicri:noRegion></affiliation></author><author><name sortKey="Nakagawa Goto, Kyoko" sort="Nakagawa Goto, Kyoko" uniqKey="Nakagawa Goto K" first="Kyoko" last="Nakagawa-Goto">Kyoko Nakagawa-Goto</name><affiliation><nlm:aff id="af1-molecules-24-04005">School of Pharmaceutical Sciences, College of Medical, Pharmaceutical and Health Sciences, Kanazawa University, Kanazawa 920-1192, Japan;<email>ismayil507@stu.kanazawa-u.ac.jp</email> (S.A.);<email>saito-y@staff.kanazawa-u.ac.jp</email> (Y.S.);<email>fukuyosi@p.kanazawa-u.ac.jp</email> (S.F.)</nlm:aff></affiliation><affiliation><nlm:aff id="af2-molecules-24-04005">Natural Products Research Laboratories, UNC Eshelman School of Pharmacy, University of North Carolina at Chapel Hill, Chapel Hill, NC 27599-7568, USA;<email>goto@med.unc.edu</email> (M.G.);<email>khlee@unc.edu</email> (K.-H.L.)</nlm:aff></affiliation></author></analytic><series><title level="j">Molecules</title><idno type="eISSN">1420-3049</idno><imprint><date when="2019">2019</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en"><p>Seven new butanolides, peltanolides A–G (<bold>1</bold>–<bold>7</bold>), and two lignan glucosides, peltasides A (<bold>8</bold>) and B (<bold>9</bold>), along with eleven known compounds, <bold>10</bold>–<bold>20</bold>, were isolated from a crude CH<sub>3</sub>OH/CH<sub>2</sub>Cl<sub>2</sub> (1:1) extract of the fruit of <italic>Hernandia nymphaeifolia</italic> (Hernandiaceae). The structures of <bold>1</bold>–<bold>9</bold> were characterized by extensive 1D and 2D NMR spectroscopic and HRMS analysis. The absolute configurations of newly isolated compounds <bold>1</bold>–<bold>9</bold> were determined from data obtained by optical rotation and electronic circular dichroism (ECD) exciton chirality methods. Butanolides and lignan glucosides have not been isolated previously from this genus. Several isolated compounds were evaluated for antiproliferative activity against human tumor cell lines. Lignans <bold>15</bold> and <bold>16</bold> were slightly active against chemosensitive tumor cell lines A549 and MCF-7, respectively. Furthermore, both compounds displayed significant activity (IC<sub>50</sub> = 5 µM) against a P-glycoprotein overexpressing multidrug-resistant tumor cell line (KB-VIN) but were less active against its parent chemosensitive cell line (KB).</p></div></front><back><div1 type="bibliography"><listBibl><biblStruct><analytic><author><name sortKey="Lakshmi, V" uniqKey="Lakshmi V">V. Lakshmi</name></author><author><name sortKey="Pandey, K" uniqKey="Pandey K">K. Pandey</name></author><author><name sortKey="Mishra, S K" uniqKey="Mishra S">S.K. Mishra</name></author><author><name sortKey="Srivastava, S" uniqKey="Srivastava S">S. Srivastava</name></author><author><name sortKey="Mishra, M" uniqKey="Mishra M">M. Mishra</name></author><author><name sortKey="Agarwa, S K" uniqKey="Agarwa S">S.K. Agarwa</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Pettit, G R" uniqKey="Pettit G">G.R. Pettit</name></author><author><name sortKey="Meng, Y H" uniqKey="Meng Y">Y.H. 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Goto</name></author></analytic></biblStruct></listBibl></div1></back></TEI><affiliations><list><country><li>Taïwan</li><li>États-Unis</li></country></list><tree><noCountry><name sortKey="Aimaiti, Simayijiang" sort="Aimaiti, Simayijiang" uniqKey="Aimaiti S" first="Simayijiang" last="Aimaiti">Simayijiang Aimaiti</name><name sortKey="Fukuyoshi, Shuichi" sort="Fukuyoshi, Shuichi" uniqKey="Fukuyoshi S" first="Shuichi" last="Fukuyoshi">Shuichi Fukuyoshi</name><name sortKey="Goto, Masuo" sort="Goto, Masuo" uniqKey="Goto M" first="Masuo" last="Goto">Masuo Goto</name><name sortKey="Miyake, Katsunori" sort="Miyake, Katsunori" uniqKey="Miyake K" first="Katsunori" last="Miyake">Katsunori Miyake</name><name sortKey="Nakagawa Goto, Kyoko" sort="Nakagawa Goto, Kyoko" uniqKey="Nakagawa Goto K" first="Kyoko" last="Nakagawa-Goto">Kyoko Nakagawa-Goto</name><name sortKey="Newman, David J" sort="Newman, David J" uniqKey="Newman D" first="David J." last="Newman">David J. Newman</name><name sortKey="Saito, Yohei" sort="Saito, Yohei" uniqKey="Saito Y" first="Yohei" last="Saito">Yohei Saito</name></noCountry><country name="États-Unis"><noRegion><name sortKey="O Eefe, Barry R" sort="O Eefe, Barry R" uniqKey="O Eefe B" first="Barry R." last="O Eefe">Barry R. O Eefe</name></noRegion></country><country name="Taïwan"><noRegion><name sortKey="Lee, Kuo Hsiung" sort="Lee, Kuo Hsiung" uniqKey="Lee K" first="Kuo-Hsiung" last="Lee">Kuo-Hsiung Lee</name></noRegion></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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