Euphohelides A–C, ent-Abietane-Type Norditerpene Lactones from Euphorbia helioscopia and Their Anti-Inflammatory Activities
Three unreported ent-abietane-type norditerpene lactones, euphohelides A–C (1–3), and 11 known analogs (4–14) were isolated from the whole plants of Euphorbia helioscopia L. Euphohelide A (1) is an unprecedented 2-nor-ent-abietane lactone bearing a unique 5/6/6/5 tetracyclic system. Euphohelides B (...
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| Veröffentlicht in: | Journal of natural products (Washington, D.C.) D.C.), 2023-04, Vol.86 (4), p.1003-1009 |
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| container_title | Journal of natural products (Washington, D.C.) |
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| creator | Yang, Hong-Ying Yao, Weidong Huang, Pei-Zhi Xu, Hui Ma, Qian Chen, Xiaoming Chen, Jian-Jun Gao, Kun |
| description | Three unreported ent-abietane-type norditerpene lactones, euphohelides A–C (1–3), and 11 known analogs (4–14) were isolated from the whole plants of Euphorbia helioscopia L. Euphohelide A (1) is an unprecedented 2-nor-ent-abietane lactone bearing a unique 5/6/6/5 tetracyclic system. Euphohelides B (2) and C (3) possess 2-nor-6/6/6/5 and 2,3-dinor-5/6/6/5 dilactone tetracyclic moieties, respectively. Their structures were established by spectroscopic methods, computational ECD, and X-ray crystallographic analyses. A biomimetic synthesis of 1 was achieved from precursor 4 based on the speculative biogenetic pathway. Compounds 1 and 5 significantly alleviated the release of LPS-induced NO with IC50 values of 32.98 ± 1.13 and 33.82 ± 3.25 μM, which might be related to the regulation of the NF-κB signaling pathway. |
| doi_str_mv | 10.1021/acs.jnatprod.3c00041 |
| format | Article |
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Euphohelide A (1) is an unprecedented 2-nor-ent-abietane lactone bearing a unique 5/6/6/5 tetracyclic system. Euphohelides B (2) and C (3) possess 2-nor-6/6/6/5 and 2,3-dinor-5/6/6/5 dilactone tetracyclic moieties, respectively. Their structures were established by spectroscopic methods, computational ECD, and X-ray crystallographic analyses. A biomimetic synthesis of 1 was achieved from precursor 4 based on the speculative biogenetic pathway. Compounds 1 and 5 significantly alleviated the release of LPS-induced NO with IC50 values of 32.98 ± 1.13 and 33.82 ± 3.25 μM, which might be related to the regulation of the NF-κB signaling pathway.</description><identifier>ISSN: 0163-3864</identifier><identifier>EISSN: 1520-6025</identifier><identifier>DOI: 10.1021/acs.jnatprod.3c00041</identifier><identifier>PMID: 36858948</identifier><language>eng</language><publisher>United States: American Chemical Society and American Society of Pharmacognosy</publisher><subject>Abietanes - pharmacology ; Anti-Inflammatory Agents - pharmacology ; Diterpenes - chemistry ; Diterpenes - pharmacology ; Euphorbia - chemistry ; Lactones - chemistry ; Lactones - pharmacology ; Molecular Structure</subject><ispartof>Journal of natural products (Washington, D.C.), 2023-04, Vol.86 (4), p.1003-1009</ispartof><rights>2023 American Chemical Society and American Society of Pharmacognosy</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a348t-2df90ecd2b117035a2e480e83fa9c79290211d75778c23f7520d929e5b7796363</citedby><cites>FETCH-LOGICAL-a348t-2df90ecd2b117035a2e480e83fa9c79290211d75778c23f7520d929e5b7796363</cites><orcidid>0000-0001-5998-0072 ; 0000-0002-3856-3672 ; 0000-0001-5937-5569</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/acs.jnatprod.3c00041$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.jnatprod.3c00041$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/36858948$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Yang, Hong-Ying</creatorcontrib><creatorcontrib>Yao, Weidong</creatorcontrib><creatorcontrib>Huang, Pei-Zhi</creatorcontrib><creatorcontrib>Xu, Hui</creatorcontrib><creatorcontrib>Ma, Qian</creatorcontrib><creatorcontrib>Chen, Xiaoming</creatorcontrib><creatorcontrib>Chen, Jian-Jun</creatorcontrib><creatorcontrib>Gao, Kun</creatorcontrib><title>Euphohelides A–C, ent-Abietane-Type Norditerpene Lactones from Euphorbia helioscopia and Their Anti-Inflammatory Activities</title><title>Journal of natural products (Washington, D.C.)</title><addtitle>J. Nat. Prod</addtitle><description>Three unreported ent-abietane-type norditerpene lactones, euphohelides A–C (1–3), and 11 known analogs (4–14) were isolated from the whole plants of Euphorbia helioscopia L. Euphohelide A (1) is an unprecedented 2-nor-ent-abietane lactone bearing a unique 5/6/6/5 tetracyclic system. Euphohelides B (2) and C (3) possess 2-nor-6/6/6/5 and 2,3-dinor-5/6/6/5 dilactone tetracyclic moieties, respectively. Their structures were established by spectroscopic methods, computational ECD, and X-ray crystallographic analyses. A biomimetic synthesis of 1 was achieved from precursor 4 based on the speculative biogenetic pathway. 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Nat. Prod</addtitle><date>2023-04-28</date><risdate>2023</risdate><volume>86</volume><issue>4</issue><spage>1003</spage><epage>1009</epage><pages>1003-1009</pages><issn>0163-3864</issn><eissn>1520-6025</eissn><abstract>Three unreported ent-abietane-type norditerpene lactones, euphohelides A–C (1–3), and 11 known analogs (4–14) were isolated from the whole plants of Euphorbia helioscopia L. Euphohelide A (1) is an unprecedented 2-nor-ent-abietane lactone bearing a unique 5/6/6/5 tetracyclic system. Euphohelides B (2) and C (3) possess 2-nor-6/6/6/5 and 2,3-dinor-5/6/6/5 dilactone tetracyclic moieties, respectively. Their structures were established by spectroscopic methods, computational ECD, and X-ray crystallographic analyses. A biomimetic synthesis of 1 was achieved from precursor 4 based on the speculative biogenetic pathway. 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| subjects | Abietanes - pharmacology Anti-Inflammatory Agents - pharmacology Diterpenes - chemistry Diterpenes - pharmacology Euphorbia - chemistry Lactones - chemistry Lactones - pharmacology Molecular Structure |
| title | Euphohelides A–C, ent-Abietane-Type Norditerpene Lactones from Euphorbia helioscopia and Their Anti-Inflammatory Activities |
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