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从土曲霉中提取的十环 B 型芳基麦角甾醇。

Ten ring-B aromatized ergosterols from Aspergillus spectabilis.

机构信息

Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, China.

Tongji Hospital Affiliated to Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, China.

出版信息

Chin J Nat Med. 2024 Jul;22(7):654-662. doi: 10.1016/S1875-5364(24)60594-7.

DOI:10.1016/S1875-5364(24)60594-7
PMID:39059834
Abstract

Spectasterols F-O (1-10), ten interesting ergosterols with an aromatized B ring, were obtained from Aspergillus spectabilis. Their structures and absolute configurations were determined using a combination of high-resolution electrospray ionization mass spectrometry (HR-ESI-MS), nuclear magnetic resonance (NMR) spectroscopy, single-crystal X-ray diffraction analyses, and electronic circular dichroism (ECD) calculations. Structurally, these aromatic ergosterols feature versatile side chains. Notably, compound aromatic ergosterols featured versatile side chains, and compound 4 is an unusual C23 ergosterol characterized by a shorter side chain due to oxidative cleavage between C-23 and C-24. All compounds were evaluated for their neuroprotective activities, with compound 8 showing a dose-dependent ability to reduce apoptosis and protect mitochondrial function in glutamate-induced SH-SY5Y cells.

摘要

从土曲霉中获得了 10 个具有芳香化 B 环的有趣麦角甾醇类化合物 Spectasterols F-O(1-10)。采用高分辨电喷雾电离质谱(HR-ESI-MS)、核磁共振(NMR)光谱、单晶 X 射线衍射分析和电子圆二色性(ECD)计算相结合的方法确定了它们的结构和绝对构型。从结构上看,这些芳香麦角甾醇具有多样的侧链。值得注意的是,化合物 4 是一种不寻常的 C23 麦角甾醇,由于 C-23 和 C-24 之间的氧化裂解,其侧链较短。所有化合物均进行了神经保护活性评估,化合物 8 显示出剂量依赖性降低谷氨酸诱导的 SH-SY5Y 细胞凋亡和保护线粒体功能的能力。

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