Neuroprotective Norsesquiterpenoids and Triterpenoids from Populus euphratica Resins.
Identifieur interne : 000824 ( Main/Exploration ); précédent : 000823; suivant : 000825Neuroprotective Norsesquiterpenoids and Triterpenoids from Populus euphratica Resins.
Auteurs : Yun-Yun Liu [République populaire de Chine] ; Dan-Ling Huang [République populaire de Chine] ; Yun Dong [République populaire de Chine] ; Da-Peng Qin [République populaire de Chine] ; Yong-Ming Yan [République populaire de Chine] ; Yong-Xian Cheng [République populaire de Chine]Source :
- Molecules (Basel, Switzerland) [ 1420-3049 ] ; 2019.
Descripteurs français
- KwdFr :
- Neuroprotecteurs (composition chimique), Neuroprotecteurs (pharmacologie), Populus (composition chimique), Relation structure-activité (MeSH), Résines végétales (composition chimique), Sesquiterpènes (composition chimique), Sesquiterpènes (pharmacologie), Spectroscopie par résonance magnétique (MeSH), Structure moléculaire (MeSH), Triterpènes (composition chimique), Triterpènes (pharmacologie).
- MESH :
- composition chimique : Neuroprotecteurs, Populus, Résines végétales, Sesquiterpènes, Triterpènes.
- pharmacologie : Neuroprotecteurs, Sesquiterpènes, Triterpènes.
- Relation structure-activité, Spectroscopie par résonance magnétique, Structure moléculaire.
English descriptors
- KwdEn :
- Magnetic Resonance Spectroscopy (MeSH), Molecular Structure (MeSH), Neuroprotective Agents (chemistry), Neuroprotective Agents (pharmacology), Populus (chemistry), Resins, Plant (chemistry), Sesquiterpenes (chemistry), Sesquiterpenes (pharmacology), Structure-Activity Relationship (MeSH), Triterpenes (chemistry), Triterpenes (pharmacology).
- MESH :
- chemical , chemistry : Neuroprotective Agents, Resins, Plant, Sesquiterpenes, Triterpenes.
- chemical , pharmacology : Neuroprotective Agents, Sesquiterpenes, Triterpenes.
- chemistry : Populus.
- Magnetic Resonance Spectroscopy, Molecular Structure, Structure-Activity Relationship.
Abstract
Two new octanorlanostane-type triterpenes, euphraticanoids A and B (1 and 2), two new trinorsesquiterpenoids, euphraticanoids C and D (3 and 4), and eight known triterpenoids (5, 6, 8-13) along with one steroid (7) were isolated from Populus euphratica resins. The structures of these new compounds, including their absolute configurations, were characterized by spectrocsopic, chemical, and computational methods. Biological evaluation revealed that compounds 4, 7-9, 12, and 13 display neuroprotective activities in H2O2-induced HT-22 cells with 4, 8, and 9 occurring in a concentration-dependent manner and 7, 12, and 13 reaching the maximum effects at 20 μM. Meanwhile, the neuroprotective properties of all isolates were accessed using glutamate-induced SH-SY5Y cells and disclosed that compounds 3, 4, 8, and 9 could dose-dependently protect neural cell injury in a concentration range of 10-40 μM. Finally, a brief structure-activity relationship was briefly discussed.
DOI: 10.3390/molecules24234379
PubMed: 31801194
PubMed Central: PMC6930471
Affiliations:
Links toward previous steps (curation, corpus...)
Le document en format XML
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Norsesquiterpenoids and Triterpenoids from <i>Populus euphratica</i> Resins.</title><author><name sortKey="Liu, Yun Yun" sort="Liu, Yun Yun" uniqKey="Liu Y" first="Yun-Yun" last="Liu">Yun-Yun Liu</name><affiliation wicri:level="1"><nlm:affiliation>School of Pharmaceutical Sciences, Shenzhen University Health Science Center, Shenzhen 518060, China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>School of Pharmaceutical Sciences, Shenzhen University Health Science Center, Shenzhen 518060</wicri:regionArea><placeName><settlement type="city">Shenzhen</settlement><region type="province">Guangdong</region></placeName></affiliation><affiliation wicri:level="1"><nlm:affiliation>Department of Chinese Materia Medica, Shanxi University of Chinese Medicine, Jinzhong 030619, China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>Department of Chinese Materia Medica, Shanxi University of Chinese Medicine, Jinzhong 030619</wicri:regionArea><wicri:noRegion>Jinzhong 030619</wicri:noRegion></affiliation></author><author><name sortKey="Huang, Dan Ling" sort="Huang, Dan Ling" uniqKey="Huang D" first="Dan-Ling" last="Huang">Dan-Ling Huang</name><affiliation wicri:level="1"><nlm:affiliation>School of Pharmaceutical Sciences, Shenzhen University Health Science Center, Shenzhen 518060, China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>School of Pharmaceutical Sciences, Shenzhen University Health Science Center, Shenzhen 518060</wicri:regionArea><placeName><settlement type="city">Shenzhen</settlement><region type="province">Guangdong</region></placeName></affiliation></author><author><name sortKey="Dong, Yun" sort="Dong, Yun" uniqKey="Dong Y" first="Yun" last="Dong">Yun Dong</name><affiliation wicri:level="1"><nlm:affiliation>School of Pharmaceutical Sciences, Shenzhen University Health Science Center, Shenzhen 518060, China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>School of Pharmaceutical Sciences, Shenzhen University Health Science Center, Shenzhen 518060</wicri:regionArea><placeName><settlement type="city">Shenzhen</settlement><region type="province">Guangdong</region></placeName></affiliation></author><author><name sortKey="Qin, Da Peng" sort="Qin, Da Peng" uniqKey="Qin D" first="Da-Peng" last="Qin">Da-Peng Qin</name><affiliation wicri:level="1"><nlm:affiliation>School of Pharmaceutical Sciences, Shenzhen University Health Science Center, Shenzhen 518060, China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>School of Pharmaceutical Sciences, Shenzhen University Health Science Center, Shenzhen 518060</wicri:regionArea><placeName><settlement type="city">Shenzhen</settlement><region type="province">Guangdong</region></placeName></affiliation></author><author><name sortKey="Yan, Yong Ming" sort="Yan, Yong Ming" uniqKey="Yan Y" first="Yong-Ming" last="Yan">Yong-Ming Yan</name><affiliation wicri:level="1"><nlm:affiliation>School of Pharmaceutical Sciences, Shenzhen University Health Science Center, Shenzhen 518060, China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>School of Pharmaceutical Sciences, Shenzhen University Health Science Center, Shenzhen 518060</wicri:regionArea><placeName><settlement type="city">Shenzhen</settlement><region type="province">Guangdong</region></placeName></affiliation></author><author><name sortKey="Cheng, Yong Xian" sort="Cheng, Yong Xian" uniqKey="Cheng Y" first="Yong-Xian" last="Cheng">Yong-Xian Cheng</name><affiliation wicri:level="1"><nlm:affiliation>School of Pharmaceutical Sciences, Shenzhen University Health Science Center, Shenzhen 518060, China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>School of Pharmaceutical Sciences, Shenzhen University Health Science Center, Shenzhen 518060</wicri:regionArea><placeName><settlement type="city">Shenzhen</settlement><region type="province">Guangdong</region></placeName></affiliation></author></analytic><series><title level="j">Molecules (Basel, Switzerland)</title><idno type="eISSN">1420-3049</idno><imprint><date when="2019" type="published">2019</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Magnetic Resonance Spectroscopy (MeSH)</term><term>Molecular Structure (MeSH)</term><term>Neuroprotective Agents (chemistry)</term><term>Neuroprotective Agents (pharmacology)</term><term>Populus (chemistry)</term><term>Resins, Plant (chemistry)</term><term>Sesquiterpenes (chemistry)</term><term>Sesquiterpenes (pharmacology)</term><term>Structure-Activity Relationship (MeSH)</term><term>Triterpenes (chemistry)</term><term>Triterpenes (pharmacology)</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>Neuroprotecteurs (composition chimique)</term><term>Neuroprotecteurs (pharmacologie)</term><term>Populus (composition chimique)</term><term>Relation structure-activité (MeSH)</term><term>Résines végétales (composition chimique)</term><term>Sesquiterpènes (composition chimique)</term><term>Sesquiterpènes (pharmacologie)</term><term>Spectroscopie par résonance magnétique (MeSH)</term><term>Structure moléculaire (MeSH)</term><term>Triterpènes (composition chimique)</term><term>Triterpènes (pharmacologie)</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Neuroprotective Agents</term><term>Resins, Plant</term><term>Sesquiterpenes</term><term>Triterpenes</term></keywords><keywords scheme="MESH" type="chemical" qualifier="pharmacology" xml:lang="en"><term>Neuroprotective Agents</term><term>Sesquiterpenes</term><term>Triterpenes</term></keywords><keywords scheme="MESH" qualifier="chemistry" xml:lang="en"><term>Populus</term></keywords><keywords scheme="MESH" qualifier="composition chimique" xml:lang="fr"><term>Neuroprotecteurs</term><term>Populus</term><term>Résines végétales</term><term>Sesquiterpènes</term><term>Triterpènes</term></keywords><keywords scheme="MESH" qualifier="pharmacologie" xml:lang="fr"><term>Neuroprotecteurs</term><term>Sesquiterpènes</term><term>Triterpènes</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Magnetic Resonance Spectroscopy</term><term>Molecular Structure</term><term>Structure-Activity Relationship</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>Relation structure-activité</term><term>Spectroscopie par résonance magnétique</term><term>Structure moléculaire</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">Two new octanorlanostane-type triterpenes, euphraticanoids A and B (<b>1</b> and <b>2</b>), two new trinorsesquiterpenoids, euphraticanoids C and D (<b>3</b> and <b>4</b>), and eight known triterpenoids (<b>5</b>, <b>6</b>, <b>8</b>-<b>13</b>) along with one steroid (<b>7</b>) were isolated from <i>Populus euphratica</i> resins. The structures of these new compounds, including their absolute configurations, were characterized by spectrocsopic, chemical, and computational methods. Biological evaluation revealed that compounds <b>4</b>, <b>7</b>-<b>9</b>, <b>12</b>, and <b>13</b> display neuroprotective activities in H<sub>2</sub>O<sub>2</sub>-induced HT-22 cells with <b>4</b>, <b>8</b>, and <b>9</b> occurring in a concentration-dependent manner and <b>7</b>, <b>12</b>, and <b>13</b> reaching the maximum effects at 20 μM. Meanwhile, the neuroprotective properties of all isolates were accessed using glutamate-induced SH-SY5Y cells and disclosed that compounds <b>3</b>, <b>4</b>, <b>8</b>, and <b>9</b> could dose-dependently protect neural cell injury in a concentration range of 10-40 μM. Finally, a brief structure-activity relationship was briefly discussed.</div></front></TEI><pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">31801194</PMID><DateCompleted><Year>2020</Year><Month>04</Month><Day>23</Day></DateCompleted><DateRevised><Year>2020</Year><Month>04</Month><Day>23</Day></DateRevised><Article PubModel="Electronic"><Journal><ISSN IssnType="Electronic">1420-3049</ISSN><JournalIssue CitedMedium="Internet"><Volume>24</Volume><Issue>23</Issue><PubDate><Year>2019</Year><Month>Nov</Month><Day>30</Day></PubDate></JournalIssue><Title>Molecules (Basel, Switzerland)</Title><ISOAbbreviation>Molecules</ISOAbbreviation></Journal><ArticleTitle>Neuroprotective Norsesquiterpenoids and Triterpenoids from <i>Populus euphratica</i> Resins.</ArticleTitle><ELocationID EIdType="pii" ValidYN="Y">E4379</ELocationID><ELocationID EIdType="doi" ValidYN="Y">10.3390/molecules24234379</ELocationID><Abstract><AbstractText>Two new octanorlanostane-type triterpenes, euphraticanoids A and B (<b>1</b> and <b>2</b>), two new trinorsesquiterpenoids, euphraticanoids C and D (<b>3</b> and <b>4</b>), and eight known triterpenoids (<b>5</b>, <b>6</b>, <b>8</b>-<b>13</b>) along with one steroid (<b>7</b>) were isolated from <i>Populus euphratica</i> resins. The structures of these new compounds, including their absolute configurations, were characterized by spectrocsopic, chemical, and computational methods. Biological evaluation revealed that compounds <b>4</b>, <b>7</b>-<b>9</b>, <b>12</b>, and <b>13</b> display neuroprotective activities in H<sub>2</sub>O<sub>2</sub>-induced HT-22 cells with <b>4</b>, <b>8</b>, and <b>9</b> occurring in a concentration-dependent manner and <b>7</b>, <b>12</b>, and <b>13</b> reaching the maximum effects at 20 μM. Meanwhile, the neuroprotective properties of all isolates were accessed using glutamate-induced SH-SY5Y cells and disclosed that compounds <b>3</b>, <b>4</b>, <b>8</b>, and <b>9</b> could dose-dependently protect neural cell injury in a concentration range of 10-40 μM. Finally, a brief structure-activity relationship was briefly discussed.</AbstractText></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Liu</LastName><ForeName>Yun-Yun</ForeName><Initials>YY</Initials><AffiliationInfo><Affiliation>School of Pharmaceutical Sciences, Shenzhen University Health Science Center, Shenzhen 518060, China.</Affiliation></AffiliationInfo><AffiliationInfo><Affiliation>Department of Chinese Materia Medica, Shanxi University of Chinese Medicine, Jinzhong 030619, China.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Huang</LastName><ForeName>Dan-Ling</ForeName><Initials>DL</Initials><AffiliationInfo><Affiliation>School of Pharmaceutical Sciences, Shenzhen University Health Science Center, Shenzhen 518060, China.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Dong</LastName><ForeName>Yun</ForeName><Initials>Y</Initials><AffiliationInfo><Affiliation>School of Pharmaceutical Sciences, Shenzhen University Health Science Center, Shenzhen 518060, China.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Qin</LastName><ForeName>Da-Peng</ForeName><Initials>DP</Initials><Identifier Source="ORCID">0000-0002-5067-9694</Identifier><AffiliationInfo><Affiliation>School of Pharmaceutical Sciences, Shenzhen University Health Science Center, Shenzhen 518060, China.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Yan</LastName><ForeName>Yong-Ming</ForeName><Initials>YM</Initials><AffiliationInfo><Affiliation>School of Pharmaceutical Sciences, Shenzhen University Health Science Center, Shenzhen 518060, China.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Cheng</LastName><ForeName>Yong-Xian</ForeName><Initials>YX</Initials><AffiliationInfo><Affiliation>School of Pharmaceutical Sciences, Shenzhen University Health Science Center, Shenzhen 518060, China.</Affiliation></AffiliationInfo></Author></AuthorList><Language>eng</Language><GrantList CompleteYN="Y"><Grant><GrantID>2017YFA0503900</GrantID><Agency>National Key Research and Development Program of China</Agency><Country></Country></Grant><Grant><GrantID>81525026</GrantID><Agency>National Science Fund for Distinguished Young Scholars</Agency><Country></Country></Grant></GrantList><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType></PublicationTypeList><ArticleDate DateType="Electronic"><Year>2019</Year><Month>11</Month><Day>30</Day></ArticleDate></Article><MedlineJournalInfo><Country>Switzerland</Country><MedlineTA>Molecules</MedlineTA><NlmUniqueID>100964009</NlmUniqueID><ISSNLinking>1420-3049</ISSNLinking></MedlineJournalInfo><ChemicalList><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D018696">Neuroprotective Agents</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D012116">Resins, Plant</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D012717">Sesquiterpenes</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D014315">Triterpenes</NameOfSubstance></Chemical></ChemicalList><CitationSubset>IM</CitationSubset><MeshHeadingList><MeshHeading><DescriptorName UI="D009682" MajorTopicYN="N">Magnetic Resonance Spectroscopy</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D015394" MajorTopicYN="N">Molecular Structure</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D018696" MajorTopicYN="N">Neuroprotective Agents</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName><QualifierName UI="Q000494" MajorTopicYN="Y">pharmacology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D032107" MajorTopicYN="N">Populus</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D012116" MajorTopicYN="N">Resins, Plant</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D012717" MajorTopicYN="N">Sesquiterpenes</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName><QualifierName UI="Q000494" MajorTopicYN="Y">pharmacology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D013329" MajorTopicYN="N">Structure-Activity Relationship</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D014315" MajorTopicYN="N">Triterpenes</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName><QualifierName UI="Q000494" MajorTopicYN="Y">pharmacology</QualifierName></MeshHeading></MeshHeadingList><KeywordList Owner="NOTNLM"><Keyword MajorTopicYN="N">Populus euphratica</Keyword><Keyword MajorTopicYN="N">neuroprotection</Keyword><Keyword MajorTopicYN="N">plant resins</Keyword><Keyword MajorTopicYN="N">sesquiterpenoids</Keyword><Keyword 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de Chine</li></country><region><li>Guangdong</li></region><settlement><li>Shenzhen</li></settlement></list><tree><country name="République populaire de Chine"><region name="Guangdong"><name sortKey="Liu, Yun Yun" sort="Liu, Yun Yun" uniqKey="Liu Y" first="Yun-Yun" last="Liu">Yun-Yun Liu</name></region><name sortKey="Cheng, Yong Xian" sort="Cheng, Yong Xian" uniqKey="Cheng Y" first="Yong-Xian" last="Cheng">Yong-Xian Cheng</name><name sortKey="Dong, Yun" sort="Dong, Yun" uniqKey="Dong Y" first="Yun" last="Dong">Yun Dong</name><name sortKey="Huang, Dan Ling" sort="Huang, Dan Ling" uniqKey="Huang D" first="Dan-Ling" last="Huang">Dan-Ling Huang</name><name sortKey="Liu, Yun Yun" sort="Liu, Yun Yun" uniqKey="Liu Y" first="Yun-Yun" last="Liu">Yun-Yun Liu</name><name sortKey="Qin, Da Peng" sort="Qin, Da Peng" uniqKey="Qin D" first="Da-Peng" last="Qin">Da-Peng Qin</name><name sortKey="Yan, Yong Ming" sort="Yan, Yong Ming" uniqKey="Yan Y" first="Yong-Ming" last="Yan">Yong-Ming 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