Flueggenoids A – E, new dinorditerpenoids from Flueggea virosa
A phytochemical investigation on the twigs and leaves of Flueggea virosa (Euphorbiaceae) led to the isolation of flueggenoids A – E (1–5), five new 13-methyl-ent-podocarpanes, together with eleven known compounds (6–16). Their structures and absolute configurations were elucidated on the basis of ex...
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| Veröffentlicht in: | Fitoterapia 2019-03, Vol.133, p.96-101 |
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| creator | Wang, Xiao-Feng Liu, Fei-Fei Zhu, Zhengdan Fang, Qiang-Qiang Qu, Shi-Jin Zhu, Weiliang Yang, Li Zuo, Jian-Ping Tan, Chang-Heng |
| description | A phytochemical investigation on the twigs and leaves of Flueggea virosa (Euphorbiaceae) led to the isolation of flueggenoids A – E (1–5), five new 13-methyl-ent-podocarpanes, together with eleven known compounds (6–16). Their structures and absolute configurations were elucidated on the basis of extensive MS and NMR data analysis, and/or single-crystal X-ray diffraction, time-dependent density functional theory (TDDFT)-based electronic circular dichroism (ECD) calculations, and chemical transformation. All isolates were evaluated for anti-HCV activity, the results showed that terpenoids of F. virosa had nonnegligible contribution for the anti-HCV activity.
Graphic abstract [Display omitted]
•16 components, including 10 terpenoids and 4 Securinega alkaloids, were isolated from Flueggea virosa.•Flueggenoids A – E were identified to be new 13-methyl-ent-podocarpane type dinorditerpenoids.•The structure and configuration of 9 was revised.•Alkaloid 11 and terpenoid 3 showed more potent anti-HCV effect than honokiol. |
| doi_str_mv | 10.1016/j.fitote.2018.12.025 |
| format | Article |
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Graphic abstract [Display omitted]
•16 components, including 10 terpenoids and 4 Securinega alkaloids, were isolated from Flueggea virosa.•Flueggenoids A – E were identified to be new 13-methyl-ent-podocarpane type dinorditerpenoids.•The structure and configuration of 9 was revised.•Alkaloid 11 and terpenoid 3 showed more potent anti-HCV effect than honokiol.</description><identifier>ISSN: 0367-326X</identifier><identifier>EISSN: 1873-6971</identifier><identifier>DOI: 10.1016/j.fitote.2018.12.025</identifier><identifier>PMID: 30605781</identifier><language>eng</language><publisher>Netherlands: Elsevier B.V</publisher><subject>13-Methyl-ent-podocarpane ; Anti-HCV ; Circular dichroism ; Crystals ; Data analysis ; Data processing ; Density functional theory ; Dichroism ; Flueggea ; Flueggea virosa ; NMR ; Nuclear magnetic resonance ; Organic chemistry ; Securinega alkaloids ; Single crystals ; TDDFT ECD ; Terpenes ; Time dependence ; X-ray diffraction</subject><ispartof>Fitoterapia, 2019-03, Vol.133, p.96-101</ispartof><rights>2018</rights><rights>Copyright © 2018. Published by Elsevier B.V.</rights><rights>Copyright Elsevier Science Ltd. Mar 2019</rights><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c390t-8f94f6f918bf6cc1b88bf6acbf8a5070c767a86a8b578887c3fa27af844ddc8c3</citedby><cites>FETCH-LOGICAL-c390t-8f94f6f918bf6cc1b88bf6acbf8a5070c767a86a8b578887c3fa27af844ddc8c3</cites><orcidid>0000-0002-4269-1634 ; 0000-0001-7718-1653</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0367326X18321439$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3536,27903,27904,65309</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/30605781$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Wang, Xiao-Feng</creatorcontrib><creatorcontrib>Liu, Fei-Fei</creatorcontrib><creatorcontrib>Zhu, Zhengdan</creatorcontrib><creatorcontrib>Fang, Qiang-Qiang</creatorcontrib><creatorcontrib>Qu, Shi-Jin</creatorcontrib><creatorcontrib>Zhu, Weiliang</creatorcontrib><creatorcontrib>Yang, Li</creatorcontrib><creatorcontrib>Zuo, Jian-Ping</creatorcontrib><creatorcontrib>Tan, Chang-Heng</creatorcontrib><title>Flueggenoids A – E, new dinorditerpenoids from Flueggea virosa</title><title>Fitoterapia</title><addtitle>Fitoterapia</addtitle><description>A phytochemical investigation on the twigs and leaves of Flueggea virosa (Euphorbiaceae) led to the isolation of flueggenoids A – E (1–5), five new 13-methyl-ent-podocarpanes, together with eleven known compounds (6–16). Their structures and absolute configurations were elucidated on the basis of extensive MS and NMR data analysis, and/or single-crystal X-ray diffraction, time-dependent density functional theory (TDDFT)-based electronic circular dichroism (ECD) calculations, and chemical transformation. All isolates were evaluated for anti-HCV activity, the results showed that terpenoids of F. virosa had nonnegligible contribution for the anti-HCV activity.
Graphic abstract [Display omitted]
•16 components, including 10 terpenoids and 4 Securinega alkaloids, were isolated from Flueggea virosa.•Flueggenoids A – E were identified to be new 13-methyl-ent-podocarpane type dinorditerpenoids.•The structure and configuration of 9 was revised.•Alkaloid 11 and terpenoid 3 showed more potent anti-HCV effect than honokiol.</description><subject>13-Methyl-ent-podocarpane</subject><subject>Anti-HCV</subject><subject>Circular dichroism</subject><subject>Crystals</subject><subject>Data analysis</subject><subject>Data processing</subject><subject>Density functional theory</subject><subject>Dichroism</subject><subject>Flueggea</subject><subject>Flueggea virosa</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Organic chemistry</subject><subject>Securinega alkaloids</subject><subject>Single crystals</subject><subject>TDDFT ECD</subject><subject>Terpenes</subject><subject>Time dependence</subject><subject>X-ray diffraction</subject><issn>0367-326X</issn><issn>1873-6971</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNp9kMtKw0AUhgdRbL28gUjArYlzSWYmG7GUVoWCGwV3w2QuZUKb1Jmk4s538A19EqekunR1Dpz_P-c_HwAXCGYIInpTZ9Z1bWcyDBHPEM4gLg7AGHFGUloydAjGkFCWEkxfR-AkhBpCVJAcHYMRgRQWjKMxuJuverNcmqZ1OiST5PvzK5ldJ415T7RrWq9dZ_xmP7a-XSd7g0y2zrdBnoEjK1fBnO_rKXiZz56nD-ni6f5xOlmkipSwS7ktc0ttiXhlqVKo4rtGqspyWUAGFaNMcip5FXNxzhSxEjNpeZ5rrbgip-Bq2Lvx7VtvQifqtvdNPCkwhjljtCjzqMoHlYrZgjdWbLxbS_8hEBQ7bKIWAzaxwyYQFhFbtF3ul_fV2ug_0y-nKLgdBCa-uHXGi6CcaZTRzhvVCd26_y_8AD6_gLU</recordid><startdate>201903</startdate><enddate>201903</enddate><creator>Wang, Xiao-Feng</creator><creator>Liu, Fei-Fei</creator><creator>Zhu, Zhengdan</creator><creator>Fang, Qiang-Qiang</creator><creator>Qu, Shi-Jin</creator><creator>Zhu, Weiliang</creator><creator>Yang, Li</creator><creator>Zuo, Jian-Ping</creator><creator>Tan, Chang-Heng</creator><general>Elsevier B.V</general><general>Elsevier Science Ltd</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7QO</scope><scope>7T7</scope><scope>7U7</scope><scope>7U9</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>H94</scope><scope>M7N</scope><scope>P64</scope><orcidid>https://orcid.org/0000-0002-4269-1634</orcidid><orcidid>https://orcid.org/0000-0001-7718-1653</orcidid></search><sort><creationdate>201903</creationdate><title>Flueggenoids A – E, new dinorditerpenoids from Flueggea virosa</title><author>Wang, Xiao-Feng ; Liu, Fei-Fei ; Zhu, Zhengdan ; Fang, Qiang-Qiang ; Qu, Shi-Jin ; Zhu, Weiliang ; Yang, Li ; Zuo, Jian-Ping ; Tan, Chang-Heng</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c390t-8f94f6f918bf6cc1b88bf6acbf8a5070c767a86a8b578887c3fa27af844ddc8c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>13-Methyl-ent-podocarpane</topic><topic>Anti-HCV</topic><topic>Circular dichroism</topic><topic>Crystals</topic><topic>Data analysis</topic><topic>Data processing</topic><topic>Density functional theory</topic><topic>Dichroism</topic><topic>Flueggea</topic><topic>Flueggea virosa</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Organic chemistry</topic><topic>Securinega alkaloids</topic><topic>Single crystals</topic><topic>TDDFT ECD</topic><topic>Terpenes</topic><topic>Time dependence</topic><topic>X-ray diffraction</topic><toplevel>online_resources</toplevel><creatorcontrib>Wang, Xiao-Feng</creatorcontrib><creatorcontrib>Liu, Fei-Fei</creatorcontrib><creatorcontrib>Zhu, Zhengdan</creatorcontrib><creatorcontrib>Fang, Qiang-Qiang</creatorcontrib><creatorcontrib>Qu, Shi-Jin</creatorcontrib><creatorcontrib>Zhu, Weiliang</creatorcontrib><creatorcontrib>Yang, Li</creatorcontrib><creatorcontrib>Zuo, Jian-Ping</creatorcontrib><creatorcontrib>Tan, Chang-Heng</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Industrial and Applied Microbiology Abstracts (Microbiology A)</collection><collection>Toxicology Abstracts</collection><collection>Virology and AIDS Abstracts</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>AIDS and Cancer Research Abstracts</collection><collection>Algology Mycology and Protozoology Abstracts (Microbiology C)</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Fitoterapia</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Wang, Xiao-Feng</au><au>Liu, Fei-Fei</au><au>Zhu, Zhengdan</au><au>Fang, Qiang-Qiang</au><au>Qu, Shi-Jin</au><au>Zhu, Weiliang</au><au>Yang, Li</au><au>Zuo, Jian-Ping</au><au>Tan, Chang-Heng</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Flueggenoids A – E, new dinorditerpenoids from Flueggea virosa</atitle><jtitle>Fitoterapia</jtitle><addtitle>Fitoterapia</addtitle><date>2019-03</date><risdate>2019</risdate><volume>133</volume><spage>96</spage><epage>101</epage><pages>96-101</pages><issn>0367-326X</issn><eissn>1873-6971</eissn><abstract>A phytochemical investigation on the twigs and leaves of Flueggea virosa (Euphorbiaceae) led to the isolation of flueggenoids A – E (1–5), five new 13-methyl-ent-podocarpanes, together with eleven known compounds (6–16). Their structures and absolute configurations were elucidated on the basis of extensive MS and NMR data analysis, and/or single-crystal X-ray diffraction, time-dependent density functional theory (TDDFT)-based electronic circular dichroism (ECD) calculations, and chemical transformation. All isolates were evaluated for anti-HCV activity, the results showed that terpenoids of F. virosa had nonnegligible contribution for the anti-HCV activity.
Graphic abstract [Display omitted]
•16 components, including 10 terpenoids and 4 Securinega alkaloids, were isolated from Flueggea virosa.•Flueggenoids A – E were identified to be new 13-methyl-ent-podocarpane type dinorditerpenoids.•The structure and configuration of 9 was revised.•Alkaloid 11 and terpenoid 3 showed more potent anti-HCV effect than honokiol.</abstract><cop>Netherlands</cop><pub>Elsevier B.V</pub><pmid>30605781</pmid><doi>10.1016/j.fitote.2018.12.025</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0002-4269-1634</orcidid><orcidid>https://orcid.org/0000-0001-7718-1653</orcidid></addata></record> |
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| subjects | 13-Methyl-ent-podocarpane Anti-HCV Circular dichroism Crystals Data analysis Data processing Density functional theory Dichroism Flueggea Flueggea virosa NMR Nuclear magnetic resonance Organic chemistry Securinega alkaloids Single crystals TDDFT ECD Terpenes Time dependence X-ray diffraction |
| title | Flueggenoids A – E, new dinorditerpenoids from Flueggea virosa |
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