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

doi:10.3390/md10030639

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

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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 Zhao⁴, Dong Liu⁵, Zhen-Hao Xu⁴, Xiao-Meng Lang⁵, Ping Ao¹, Wen-Han Lin⁵, Song-Lin Yang², Zhi-Gang Zhang^3,* and Jun Xu^4,*

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

This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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MDPI and ACS Style

Xu, M.-J.; Liu, X.-J.; Zhao, Y.-L.; Liu, D.; Xu, Z.-H.; Lang, X.-M.; Ao, P.; Lin, W.-H.; Yang, S.-L.; Zhang, Z.-G.; Xu, J. Identification and Characterization of an Anti-Fibrotic Benzopyran Compound Isolated from Mangrove-Derived Streptomyces xiamenensis. Mar. Drugs 2012, 10, 639-654.

AMA Style

Xu M-J, Liu X-J, Zhao Y-L, Liu D, Xu Z-H, Lang X-M, Ao P, Lin W-H, Yang S-L, Zhang Z-G, Xu J. Identification and Characterization of an Anti-Fibrotic Benzopyran Compound Isolated from Mangrove-Derived Streptomyces xiamenensis. Marine Drugs. 2012; 10(3):639-654.

Chicago/Turabian Style

Xu, Min-Juan; Liu, Xiao-Jin; Zhao, Yi-Lei; Liu, Dong; Xu, Zhen-Hao; Lang, Xiao-Meng; Ao, Ping; Lin, Wen-Han; Yang, Song-Lin; Zhang, Zhi-Gang; Xu, Jun. 2012. "Identification and Characterization of an Anti-Fibrotic Benzopyran Compound Isolated from Mangrove-Derived Streptomyces xiamenensis." Mar. Drugs 10, no. 3: 639-654.

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