Vernonolide A, a Sesquiterpene Lactone with a Unique Carbon Skeleton from Vernonia cinerea

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-01-11 DOI:10.1021/acs.orglett.4c04760

Mengke Zhang, Tamara P. Kondratyuk, Shugeng Cao, Mu Li, Thanapat Songsak, Supakit Wongwiwatthananukit, You-Sheng Cai, Leng Chee Chang

引用次数: 0

Abstract

A novel sesquiterpene lactone derivative, vernonolide A (1), featuring an unprecedented carbon skeleton, along with its plausible biosynthetic precursor, vercinolide I (2), and eight known sesquiterpene lactones (3–10) were isolated and characterized from the whole plants of Vernonia cinerea (L.). The structures of 1 and 2 were elucidated using nuclear magnetic resonance spectroscopic analysis and calculated and experimental electronic circular dichroism spectra. A plausible biosynthetic pathway for 1 was proposed. Notably, compounds 8 and 10 exhibited significant inhibitory effects on tumor necrosis factor-α-induced nuclear factor-κB activity, with IC₅₀ values of 0.95 and 5.57 μM, respectively.

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Vernonolide A，一种具有独特碳骨架的倍半萜内酯，来自Vernonia cinerea

从Vernonia cinerea （L.）的全株植物中分离出一种新的倍半萜内酯衍生物vernonolide A(1)，具有前所未有的碳骨架，以及其似是而非的生物合成前体vercinolide I(2)和8种已知的倍半萜内酯（3-10）。利用核磁共振波谱分析、计算和实验电子圆二色光谱对1和2的结构进行了分析。提出了1的生物合成途径。值得注意的是，化合物8和10对肿瘤坏死因子-α-诱导的核因子-κB活性有明显的抑制作用，IC50值分别为0.95和5.57 μM。

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.