Chemoenzymatic Generation of Thio-analogues of δ-Cadinene, δ-Cadinol, and a Thio-diquinane Using 8-Thio-farnesylpyrophosphate.

IF 3.3 2区生物学 Q2 CHEMISTRY, MEDICINAL

Journal of Natural Products Pub Date : 2025-07-17 DOI:10.1021/acs.jnatprod.5c00409

Birk Jäger, Jan Luca Budde, Norman Birke, Maximilian Hauke, Andreas Kirschning

引用次数: 0

Abstract

The synthesis of 8-thio-farnesylpyrophosphate is reported, which was subjected to biotransformations with different sesquiterpene synthases. The 9-thio-analogues of δ-cadinene and δ-cadinol were formed by the sesquiterpene synthases Cop4 and Omp7. In contrast, the fungal sesquiterpene synthase BcBOT2 yielded a diquinane terpenoid that contains a keto and thiol group. The formation of the two former "sulfo"-terpenoids can be rationalized by following the route proposed for δ-cadinene and δ-cadinol. The latter can be regarded by the result of a late-stage hydrolysis product during the analogous pathway to presilphiperfolan-8β-ol, the natural product of BcBOT2. The olfactoric analysis of the three "sulfo"-sesuiterpenoids revealed a stale odor for the cadinene derivatives, whereas the ketothiol diquinane exhibits a spicy aroma with a subtle chili note.

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用8-硫代法尼基焦磷酸盐化学酶促生成δ- cad二烯、δ- cad二醇和硫代二醌的硫代类似物。

本文报道了8-硫代法尼基焦磷酸的合成，并对其进行了不同倍半萜合成酶的生物转化。通过倍半萜合成酶Cop4和Omp7合成δ- cad二烯和δ- cad二醇的9-硫代类似物。相比之下，真菌倍半萜合成酶BcBOT2产生含有酮和硫醇基团的二醌类萜。前两种“磺化”萜类化合物的形成可以按照δ-二苯二烯和δ-二苯二醇的生成路线进行合理化。后者可以被认为是bbcbot2天然产物pre - ilphiperfolan-8β-ol类似途径的后期水解产物的结果。对三种“磺胺”-次亚萜类化合物的嗅觉分析显示，丁二烯衍生物有一种难闻的气味，而酮硫醇二醌则表现出一种带有轻微辣椒味的辛辣香气。

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.