裂谷酮A和B：两个碳骨架重排的苯丙酰戊基萘醌

IF 3.6 2区化学 Q1 CHEMISTRY, ORGANIC

Journal of Organic Chemistry Pub Date : 2025-06-03 DOI:10.1021/acs.joc.5c0081510.1021/acs.joc.5c00815

Chu-Hua Lai, Jun-Cheng Su, Hai-Wang Yang, Yun-Qi Fan, Jian-Guo Song, Ni-Ping Li, Wen-Tao Wei, Yang Chen*, Lei Wang* and Ji-Hong Gu*,

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引用次数: 0

摘要

从黄裂藤叶中分离得到碳骨架重排的萘醌类化合物裂酮A和B（1和2）。结构上，化合物1和2具有前所未有的苯丙基苯并二环[3.3.1]壬烯核，可通过分子内键形成和环裂解级联生物合成追溯到平面萘醌前体。此外，化合物1和2对人角化细胞HaCaT细胞系IL-8的产生有显著的抑制作用。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Fissistonones A and B: Two Phenylpropanoyl Prenylated Naphthoquinones with Rearranged Carbon Skeletons from Fissistigma oldhamii

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Fissistonones A and B: Two Phenylpropanoyl Prenylated Naphthoquinones with Rearranged Carbon Skeletons from Fissistigma oldhamii

Fissistonones A and B (1 and 2), two naphthoquinone derivatives with rearranged carbon skeletons, were obtained from the leaves of Fissistigma oldhamii. Structurally, compounds 1 and 2 featured an unprecedented phenylpropanoyl benzobicyclo[3.3.1]nonene core, which could be biosynthetically traced back to a planar naphthoquinone precursor via a cascade of intramolecular bond formation and ring cleavage. In addition, compounds 1 and 2 exhibited significant inhibitory activities on IL-8 production in the human keratinocyte HaCaT cell line.

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来源期刊

Journal of Organic Chemistry 化学-有机化学

CiteScore

6.20

自引率

11.10%

发文量

1467

审稿时长

2 months

期刊介绍： Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.