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Mar. Drugs 2012, 10(3), 639-654; doi:10.3390/md10030639

Article

Identification and Characterization of an Anti-Fibrotic Benzopyran Compound Isolated from Mangrove-Derived Streptomyces xiamenensis

Min-Juan Xu ^1,† , Xiao-Jin Liu ^2,3,† , Yi-Lei Zhao ⁴ , Dong Liu ⁵ , Zhen-Hao Xu ⁴ , Xiao-Meng Lang ⁵ , Ping Ao ¹ , Wen-Han Lin ⁵ , Song-Lin Yang ² , Zhi-Gang Zhang ^3,*  and Jun Xu ^4,*

¹ Shanghai Center for Systems Biomedicine, Shanghai Jiao Tong University, Key Laboratory of Systems Biomedicine, Shanghai 200240, China ² Department of Plastic Surgery, Shanghai Jiaotong University Affiliated Sixth People’s Hospital, Shanghai 200233, China ³ State Key Laboratory of Oncogenes and Related Genes, Shanghai Cancer Institute, Ren Ji Hospital, Shanghai Jiao Tong University School of Medicine, Shanghai 200240, China ⁴ State Key Laboratory of Microbial Metabolism and School of Life Science & Biotechnology, Shanghai JiaoTong University, Shanghai 200240, China ⁵ State Key Laboratory of Natural and Biomimetic Drugs, Peking University, Beijing 100191, China ^† These authors contributed equally to this work.

* Authors to whom correspondence should be addressed.

Received: 21 January 2012; in revised form: 27 February 2012 / Accepted: 6 March 2012 / Published: 15 March 2012

Download PDF Full-Text [345 KB, uploaded 15 March 2012 12:10 CET]

Abstract: An anti-fibrotic compound produced by Streptomyces xiamenensis, found in mangrove sediments, was investigated for possible therapeutic effects against fibrosis. The compound, N-[[3,4-dihydro-3S-hydroxy-2S-methyl-2-(4¢R-methyl-3¢S-pentenyl)-2H-1-benzopyran-6-yl]carbonyl]-threonine (1), was isolated from crude extracts and its structure, including the absolute configuration was determined by extensive spectroscopic data analyses, Mosher’s method, Marfey’s reagent and quantum mechanical calculations. In terms of biological effects, this compound inhibits the proliferation of human lung fibroblasts (WI26), blocks adhesion of human acute monocytic leukemia cells (THP-1) to a monolayer of WI26 cells, and reduces the contractile capacity of WI26 cells in three-dimensional free-floating collagen gels. Altogether, these data indicate that we have identified a bioactive alkaloid (1) with multiple inhibitory biological effects on lung excessive fibrotic characteristics, that are likely involved in fibrosis, suggesting that this molecule might indeed have therapeutic potential against fibrosis.

Keywords: Streptomyces xiamenensis; mangrove; benzopyran; fibroblast; anti-fibrosis; anti-contractile capacity

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