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Chlorahupetenes A–D, Four Eudesmane-Type Sesquiterpenoid Dimer Enantiomers with Two Unusual Carbon Skeletons from Chloranthus henryi Var. hupehensis
The Journal of Organic Chemistry ( IF 3.6 ) Pub Date : 2022-06-15 , DOI: 10.1021/acs.joc.2c00819
Dan-Yang Zhang 1 , Jing-Jing Zhou 1 , Hui Yang 2 , Min Wang 2 , Ya-Nan Wang 3 , Shuai Liu 1 , Zi-Mo Zhang 1 , Peng-Yu Zhuang 1 , Xiao-Xia Wang 1 , Hang Liu 2
Affiliation  

(+)- and (−)-Chlorahupetenes A (1a and 1b), B (2a and 2b), C (3a and 3b), and D (4a and 4b), four unique enantiomeric pairs of eudesmane-type sesquiterpenoid dimers with two new carbon skeletons, were isolated from the aerial parts of Chloranthus henryi var. hupehensis. Compounds 1 and 2 possess an unprecedented 6/6/5/6/6 pentacyclic carbon skeleton with a new dimerization pattern of two eudesmane-type sesquiterpenoids. Compounds 3 and 4, which are fused with two eudesmane-type sesquiterpenoids via an unprecedented five-membered O-heterocyclic ring, represent a new 6/6/5/5/6/6/5 heptacyclic ring system. The structures of the compounds were determined through spectroscopic data and X-ray crystallography. Compounds 1a3b significantly inhibited NO production with IC50 values ranging from 9.62 to 12.91 μM. Moreover, compounds 1b and 3a suppressed the production of a proinflammatory mediator (TNF-α) and enzyme expression (iNOS) at the mRNA level.

中文翻译:

Chlorahupetenes A-D,四种 Eudesmane 型倍半萜二聚体对映体,具有来自 Chloranthus henryi Var 的两个不寻常的碳骨架。湖北人

(+)- 和 (-)-Chlorahupetenes A ( 1a1b )、B ( 2a2b )、C ( 3a3b ) 和 D ( 4a4b ),四个独特的对映异构体对 eudesmane 型倍半萜二聚体从Chloranthus henryi var的地上部分分离出两个新的碳骨架。湖北_ 化合物12具有前所未有的 6/6/5/6/6 五环碳骨架,具有两种 eudesmane 型倍半萜的新二聚模式。化合物34,它们通过前所未有的五元O-杂环与两个eudesmane型倍半萜类稠合,代表了一种新的6/6/5/5/6/6/5七环系统。通过光谱数据和 X 射线晶体学确定化合物的结构。化合物1a3b显着抑制 NO 的产生,IC 50值范围为 9.62 至 12.91 μM。此外,化合物1b3a在 mRNA 水平上抑制促炎介质 (TNF-α) 和酶表达 (iNOS) 的产生。
更新日期:2022-06-15
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