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克拉多辛 A 和 B,来源于黄烷酮的代谢产物,具有螺[环戊烷-1,2'-[3,9a]乙烷氧杂蒽]-2,4',9',11'-四酮骨架,来自 sp.

Cladoxanthones A and B, Xanthone-Derived Metabolites with a Spiro[cyclopentane-1,2'-[3,9a]ethanoxanthene]-2,4',9',11'-tetraone Skeleton from a sp.

机构信息

State Key Laboratory of Toxicology & Medical Countermeasures, Beijing Institute of Pharmacology & Toxicology, Beijing 100850, People's Republic of China.

NHC Key Laboratory of Biotechnology of Antibiotics, Institute of Medicinal Biotechnology, Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing 100050, People's Republic of China.

出版信息

J Nat Prod. 2022 Nov 25;85(11):2541-2546. doi: 10.1021/acs.jnatprod.2c00353. Epub 2022 Nov 11.

DOI:10.1021/acs.jnatprod.2c00353
PMID:36367222
Abstract

Cladoxanthones A () and B (), two xanthone-derived metabolites featuring a new spiro[cyclopentane-1,2'-[3,9a]ethanoxanthene]-2,4',9',11'(4a')-tetraone skeleton, were isolated from cultures of the ascomycete fungus sp., together with the known mangrovamide J (). Their structures were elucidated primarily by NMR experiments. The absolute configurations of and were assigned by X-ray crystallography using Cu Kα radiation. Compound could be generated from the hypothetical precursors related to α-methylene ketone and dihydro-xanthone via a Diels-Alder reaction, while could be an oxidative coupling product resulting from and . Compounds and showed weakly cytotoxic effects.

摘要

克拉多酮 A()和 B(),这两种黄烷酮衍生的代谢产物具有一个新的螺[环戊烷-1,2'-[3,9a]乙烷氧杂蒽]-2,4',9',11'(4a')-四酮骨架,是从曲霉属真菌的培养物中分离得到的,同时还分离得到了已知的 mangrovamide J()。它们的结构主要通过 NMR 实验阐明。通过使用 Cu Kα 辐射的 X 射线晶体学确定了和的绝对构型。化合物可以通过 Diels-Alder 反应从与α-亚甲基酮和二氢黄烷酮相关的假想前体生成,而可以是和之间的氧化偶联产物。化合物和表现出微弱的细胞毒性作用。

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