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从海洋来源的真菌柠檬青霉8413中鉴定出的呋喃衍生物和抗菌蒽醌-异色满杂化物。

Furan derivatives and antibacterial anthraquinone- isochroman hybrid identified from the marine- derived fungus Penicillium citrirum 8413.

作者信息

Li Jiayi, Ding Bo, Wang Jingru, Huang Xin, Zhou Haiming, Liu Lan, Tao Yiwen, Huang Hongbo

机构信息

Guangzhou Municipal and Guangdong Provincial Key Laboratory of Molecular Target & Clinical Pharmacology, the NMPA and State Key Laboratory of Respiratory Disease, School of Pharmaceutical Sciences, Guangzhou Medical University, Guangzhou 511436, China.

School of Marine Sciences, Sun Yat-Sen University, Zhuhai 519082, China.

出版信息

Fitoterapia. 2025 Sep;185:106775. doi: 10.1016/j.fitote.2025.106775. Epub 2025 Jul 30.

Abstract

Two new furan derivatives designated citrifuranin A (1) and citrifuranin B (2), a new anthraquinone-isochroman hybrid named penicillanthranin C (3) were isolated from the South China Sea-derived fungus Penicillium citrirum 8413, together with the known compounds emodin (4), 6,8-dihydroxy-3,4,5-trimethylisochroman (5), and penicitrinol A (6). The planar structures of these new compounds were elucidated by HR-MS and NMR spectroscopic data analyses. Citrifuranins A (1) and B (2) were determined to be a pair of E/Z isomers on the basis of the observed NOE correlations. Penicillanthranin C (3) was determined be a hybrid structure comprised of compounds 4 and 5. The absolute configurations of 3 were confirmed by comparing the experiment ECD spectrum with the calculated one. Penicillanthranin C (3) showed selective antibacterial activities against the Gram positive Staphylococcus aureus ATCC 29213 and methicillin-resistant S. aureus N315 with MIC values of 12.7 and 15.3 μg/mL, respectively.

摘要

从南海来源的真菌橘青霉8413中分离出两种新的呋喃衍生物,分别命名为柑橘呋喃素A(1)和柑橘呋喃素B(2),以及一种新的蒽醌 - 异色满杂合物青霉蒽素C(3),同时还分离出了已知化合物大黄素(4)、6,8 - 二羟基 - 3,4,5 - 三甲基异色满(5)和青霉曲菌素A(6)。通过高分辨质谱(HR - MS)和核磁共振(NMR)光谱数据分析阐明了这些新化合物的平面结构。基于观察到的核Overhauser效应(NOE)相关,确定柑橘呋喃素A(1)和B(2)为一对E/Z异构体。确定青霉蒽素C(3)为由化合物4和5组成的杂合结构。通过将实验电子圆二色光谱(ECD)与计算光谱进行比较,确认了3的绝对构型。青霉蒽素C(3)对革兰氏阳性金黄色葡萄球菌ATCC 29213和耐甲氧西林金黄色葡萄球菌N315表现出选择性抗菌活性,其最低抑菌浓度(MIC)值分别为12.7和15.3μg/mL。

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