CAS and Shandong Province Key Laboratory of Experimental Marine Biology, Center for Ocean Mega-Science, Institute of Oceanology, Chinese Academy of Sciences, Nanhai Road 7, Qingdao, 266071, China.
University of Chinese Academy of Sciences, Yuquan Road 19A, Beijing, 100049, China.
J Antibiot (Tokyo). 2023 Sep;76(9):563-566. doi: 10.1038/s41429-023-00634-x. Epub 2023 May 31.
A new steroid with strong antibacterial activity, rubensteroid A (1), along with its decarboxylic analogue, solitumergosterol A (2), were isolated and identified from the Magellan Seamount-derived fungus Penicillium rubens AS-130. The structure and absolute configuration of compound 1 were established by detailed interpretation of NMR spectroscopic analysis, mass spectrometry data, and TDDFT-ECD calculations. Compound 1 had a rare 6/6/6/6/5 pentacyclic system, which might be the [4 + 2] Diels-Alder adduct of 14,15-didehydroergosterol (14-DHE) cycloaddition with maleic acid or maleimide, followed by decarboxylation. Rubensteroid A (1) exhibited potent antibacterial activity against Escherichia coli and Vibrio parahaemolyticus, both with MIC value of 0.5 μg/mL.
从麦哲伦海山来源的真菌青霉（Penicillium rubens）AS-130 中分离并鉴定出一种具有强抗菌活性的新型甾体化合物，rubensteroid A（1）及其脱羧类似物 solitumergosterol A（2）。通过详细解析 NMR 波谱分析、质谱数据和 TDDFT-ECD 计算，确定了化合物 1 的结构和绝对构型。化合物 1 具有罕见的 6/6/6/6/5 五环体系，可能是 14,15-二脱氢麦角甾醇（14-DHE）与马来酸或马来酰亚胺的[4+2]Diels-Alder 加成物，随后脱羧。Rubensteroid A（1）对大肠杆菌和副溶血弧菌表现出强烈的抗菌活性，MIC 值均为 0.5μg/mL。
