Bioactive Natural Products from the Marine-Derived Penicillium brevicompactum OUCMDZ-4920

doi:10.6023/cjoc201705002

Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (10): 2752-2762.DOI: 10.6023/cjoc201705002 Previous Articles Next Articles

ARTICLE

海洋来源真菌Penicillium brevicompactum OUCMDZ-4920的活性产物研究

陈玲玲^a, 朱统汉^a, 朱国良^a, 刘云龙^a, 王聪^a, Pawinee Piyachaturawat^b, Arthit Chairoungdua^b, 朱伟明^a

a 中国海洋大学医药学院海洋药物教育部重点实验室青岛 266003;
b 玛希隆大学理学院生理学系曼谷 10400

收稿日期:2017-05-02 修回日期:2017-05-30 发布日期:2017-06-02
通讯作者: 朱伟明 E-mail:weimingzhu@ouc.edu.cn
基金资助:
国家自然科学基金（Nos.81561148012&41376148）、国家自然科学基金-广东联合基金（No.U1501221）资助项目

Bioactive Natural Products from the Marine-Derived Penicillium brevicompactum OUCMDZ-4920

Chen Lingling^a, Zhu Tonghan^a, Zhu Guoliang^a, Liu Yunlong^a, Wang Cong^a, Piyachaturawat Pawinee^b, Chairoungdua Arthit^b, Zhu Weiming^a

a Key Laboratory of Marine Drugs of Ministry Education of China, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003;
b Department of Physiology, Faculty of Science, Mahidol University, Bangkok 10400

Received:2017-05-02 Revised:2017-05-30 Published:2017-06-02
Contact: 10.6023/cjoc201705002 E-mail:weimingzhu@ouc.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (Nos.81561148012,41376148) and the National Natural Science Foundation of Chi-na-Guangdong Fund Joint Project (No.U1501221).

1. Bioactive Natural Products from the Marine-Derived Penicillium brevicompactum OUCMDZ-4920.PDF(9119KB)

Abstract

A mycophenolic acid producing strain OUCMDZ-4920, identified as Penicillium brevicompactum, was isolated from a marine sediment (-68 m) collected in South China Sea by means of intergrated chemical and bioactive screening method. Eleven compounds including mycophenolic acid (3) and its seven analogues (1, 2 and 4~8) were isolated from a nutrient-poor fermentation broth of P. brevicompactum OUCMDZ-4920, among which (±)-brevicolides A (1) and B (2) were new compounds. On the bases of spectroscopic and electronic circular dichroism (ECD) analyses, chemical transformation, chiral separation and Mosher's method, new compounds (-)-brevicolide A (1a), (+)-brevicolide A (1b), (-)-brevicolide B (2a) and (+)-brevicolide B (2b) were identified as 7-hydroxy-6-((S)-2-hydroxy-2-((R)-2-methyl-5-oxotetrahydrofuran-2-yl)ethyl)-5-methoxy-4-methylisobenzofuran-1(3H)-one, 7-hydroxy-6-((R)-2-hydroxy-2-((S)-2-methyl-5-oxotetrahydrofuran-2-yl)ethyl)-5-methoxy-4-methylisobenzofuran-1(3H)-one, 7-hydroxy-6-((S)-2-hydroxy-2-((S)-2-methyl-5-oxotetrahydrofuran-2-yl)ethyl)-5-methoxy-4-methylisobenzo-furan-1(3H)-one and 7-hydroxy-6-((R)-2-hydroxy-2-((R)-2-methyl-5-oxotetrahydro-furan-2-yl)ethyl)-5-methoxy-4-methylisobenzo-furan-1(3H)-one, respectively. And the known compounds were identified as mycophenolic acid (3), 3-hydroxymycophenolic acid (4), (S)-4-(5-hydroxy-7-methoxy-4-methyl-1-oxo-1,3-dihydroisobenzo-furan-6-yl)-2-methylbutanoic acid (5), norpestaphthalides A (6) and B (7), 5,7-dihydroxy-4-methylisobenzofuran-1(3H)-one (8), 6,8-dihydroxy-3-(hydroxymethyl)-1H-isochromen-1-one (9), brevianamides A (10) and E (11), respectively. Compound 3 displayed good cytotoxicities against murine leukemia P388 cell, human oral epithelial carcinoma KB cell, human colorectal cancer HT29 cell, human breast cancer MCF-7 cell, and human lung cancer A549 cell as well as good antifungal activity against Candida albicans with the IC₅₀ values of 0.4~5.29 μmol·L^-1, and a half maximal inhibitory concentration (MIC) value of 4.7 μmol·L^-1, respectively. In addition, four new compounds, (-)-7-O-methylbrevicolide A (12a), (+)-7-O-methyl-brevicolide A (12b), (-)-7-O-methyl-brevicolide B (13a) and (+)-7-O-methylbrevicolide B (13b) were also synthesized.

Key words: marine fungi, Penicillium brevicompactum, mycophenolic acid analogues, cytotoxicity, antifungal activity

Cite this article

Chen Lingling, Zhu Tonghan, Zhu Guoliang, Liu Yunlong, Wang Cong, Piyachaturawat Pawinee, Chairoungdua Arthit, Zhu Weiming. Bioactive Natural Products from the Marine-Derived Penicillium brevicompactum OUCMDZ-4920[J]. Chin. J. Org. Chem., 2017, 37(10): 2752-2762.

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海洋来源真菌Penicillium brevicompactum OUCMDZ-4920的活性产物研究

Bioactive Natural Products from the Marine-Derived Penicillium brevicompactum OUCMDZ-4920

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