Biosynthesis of Atypical Angucyclines Unveils New Ring Rearrangement Reactions Catalyzed by Flavoprotein Monooxygenases

作者：Xiao Xu, Yimin Chang, Yinghan Chen, Luning Zhou, Falei Zhang, Chuanteng Ma, Qian Che, Tianjiao Zhu, Blaine A. Pfeifer, Guojian Zhang, Dehai Li · 发表于：Organic Letters · 年份：2024 · DOI：10.1021/acs.orglett.4c02074 · 被引用次数：11 · 研究领域：Microbial Natural Products and Biosynthesis、Bioactive Compounds and Antitumor Agents、Plant biochemistry and biosynthesis

Six new angucycline structures, including spirocyclione A ( 1 ), which contains an unusual oxaspiro[5.5]undecane architecture, and its ring-A-cleaved product spirocyclione B ( 2 ), were discovered by heterologous expression of a type II polyketide biosynthetic gene cluster captured from a marine actinomycete strain Streptomyces sp. HDN155000. Three flavoprotein monooxygenases are confirmed to be responsible for the oxidative carbon skeleton rearrangements in the biosynthesis of compounds 1 and 2 . The obtained compounds showed promising cytotoxicity against different types of cancer cells.