Bipolarsterol A, a steroid with an unprecedented 6/5/6/5 carbon skeleton from the phytopathogenic fungus Bipolaris oryzae

IF 4.6 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Chemistry Frontiers Pub Date : 2024-12-19 DOI:10.1039/d4qo02057j

Meijia Zheng, Xiaotian Zhang, Xinran Zhang, Yingjie Liu, Qin Li, Lidan Mao, Weiguang Sun, Chunmei Chen, Yonghui Zhang, Hucheng Zhu

引用次数: 0

Abstract

Bipolarsterols A−H (1−8), eight undescribed steroids were isolated from Bipolaris oryzae, along with nine known congeners. Their structures and absolute configurations were elucidated by comprehensive spectroscopic techniques, NMR and ECD calculations. Compound 1 presents the first example of a 19(l0→5)-abeo-7(8→9)-abeo-ergostane, featuring an unusual spiro[4.5]decan-6-one system, and compound 2 is a new member of the rare steroid-phenylpropanoid hybrid. Compound 5 showed remarkable cytotoxicity against HT29 cells with an IC₅₀ value of 5.8 μM. Compound 8 showed significant inhibitory effect on NO production in RAW264.7 with an IC₅₀ value of 2.7 μM, through the inhibition of iNOS levels at the transcription and protein levels as well as the NF-κB pathway.

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来源期刊

Organic Chemistry Frontiers CHEMISTRY, ORGANIC-

CiteScore

7.90

自引率

11.10%

发文量

686

审稿时长

1 months

期刊介绍： Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.