Synthesis and Stereochemical Revision of Violaceoid E, a Polyoxygenated Cyclohexanoid Natural Product Isolated from Aspergillus violaceofuscus Gasperini

IF 3.7 2区生物学 Q2 CHEMISTRY, MEDICINAL

Journal of Natural Products Pub Date : 2026-07-24 Epub Date: 2026-07-02 DOI:10.1021/acs.jnatprod.6c00630

Yuki Kubo, Yusuke Ogura, Hirosato Takikawa, Hironori Okamura

引用次数: 0

Abstract

The first concise synthesis of the proposed structure of violaceoid E, possessing a cis-diol moiety, has been achieved. However, the spectroscopic data of the synthetic compound were inconsistent with those of the natural product, suggesting that the genuine violaceoid E might be a trans-diol. An efficient synthesis of our proposed trans-diol-type violaceoid E has also been achieved, enabling the establishment of the absolute configuration of natural violaceoid E.

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紫曲霉天然多氧环己酸产物Violaceoid E的合成及立体化学修正。

第一次简明合成了具有顺式二醇部分的紫罗兰类E的结构。然而，合成化合物的光谱数据与天然产物的不一致，表明真正的类紫罗兰酮E可能是反式二醇。我们所提出的反式二醇型类紫薇E也得到了有效的合成，从而建立了天然类紫薇E的绝对构型。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Journal of Natural Products 生物-药学

CiteScore

9.10

自引率

5.90%

发文量

294

审稿时长

2.3 months

期刊介绍： The Journal of Natural Products invites and publishes papers that make substantial and scholarly contributions to the area of natural products research. Contributions may relate to the chemistry and/or biochemistry of naturally occurring compounds or the biology of living systems from which they are obtained. Specifically, there may be articles that describe secondary metabolites of microorganisms, including antibiotics and mycotoxins; physiologically active compounds from terrestrial and marine plants and animals; biochemical studies, including biosynthesis and microbiological transformations; fermentation and plant tissue culture; the isolation, structure elucidation, and chemical synthesis of novel compounds from nature; and the pharmacology of compounds of natural origin. When new compounds are reported, manuscripts describing their biological activity are much preferred. Specifically, there may be articles that describe secondary metabolites of microorganisms, including antibiotics and mycotoxins; physiologically active compounds from terrestrial and marine plants and animals; biochemical studies, including biosynthesis and microbiological transformations; fermentation and plant tissue culture; the isolation, structure elucidation, and chemical synthesis of novel compounds from nature; and the pharmacology of compounds of natural origin.