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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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.