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

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 f...

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Published inMarine drugs Vol. 10; no. 3; pp. 639 - 654
Main Authors 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
Format Journal Article
LanguageEnglish
Published Switzerland MDPI AG 01.03.2012
MDPI
Subjects
anti-contractile capacity
anti-fibrosis
benzopyran
Benzopyrans - isolation & purification
Benzopyrans - pharmacology
Biological effects
Carbonyl compounds
Cell Adhesion - drug effects
Cell Line
Cell Line, Tumor
Cell Proliferation - drug effects
Chromatography, High Pressure Liquid
Collagen - chemistry
fibroblast
Fibroblasts - drug effects
Fibrosis - drug therapy
Geologic Sediments - microbiology
Humans
Hydrolysis
Indicators and Reagents
Leukemia
Magnetic Resonance Spectroscopy
mangrove
Marine
Molecular Conformation
Streptomyces
Streptomyces - growth & development
Streptomyces - metabolism
Streptomyces xiamenensis
Trees - microbiology
Xiamenensis
anti-contractile capacity
anti-fibrosis
fibroblast
mangrove
benzopyran
Streptomyces xiamenensis
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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.
AbstractList An anti-fibrotic compound produced by Streptomycesn 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.
An anti-fibrotic compound produced by Streptomycesn xiamenensis , found in mangrove sediments, was investigated for possible therapeutic effects against fibrosis . The compound, N -[[3,4-dihydro-3 S -hydroxy-2 S -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.
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.
An anti-fibrotic compound produced by Streptomycesn 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.An anti-fibrotic compound produced by Streptomycesn 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.
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.
Author Xu, Zhen-Hao
Xu, Jun
Zhang, Zhi-Gang
Zhao, Yi-Lei
Ao, Ping
Xu, Min-Juan
Lang, Xiao-Meng
Yang, Song-Lin
Liu, Xiao-Jin
Liu, Dong
Lin, Wen-Han
AuthorAffiliation 4 State Key Laboratory of Microbial Metabolism and School of Life Science & Biotechnology, Shanghai JiaoTong University, Shanghai 200240, China; Email: yileizhao@sjtu.edu.cn (Y.-L.Z.); bao2lu@gmail.com (Z.-H.X.)
5 State Key Laboratory of Natural and Biomimetic Drugs, Peking University, Beijing 100191, China; Email: ldddddd@yahoo.cn (D.L.); lxmdyt112@sina.com (X.-M.L.); whlin@bjmu.edu.cn (W.-H.L.)
2 Department of Plastic Surgery, Shanghai Jiaotong University Affiliated Sixth People’s Hospital, Shanghai 200233, China; Email: xjliu00058065@gmail.com (X.-J.L.); yangsonglin1961@gmail.com (S.-L.Y.)
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
1 Shanghai Center for Systems Biomedicine, Shanghai Jiao Tong University, Key Laboratory of Systems Biomedicine, Shanghai 200240, China; Email: minjuanxu@sjtu.edu.cn (M.-J.X.); aoping@sjtu.edu.cn (P.A.)
AuthorAffiliation_xml – name: 2 Department of Plastic Surgery, Shanghai Jiaotong University Affiliated Sixth People’s Hospital, Shanghai 200233, China; Email: xjliu00058065@gmail.com (X.-J.L.); yangsonglin1961@gmail.com (S.-L.Y.)
– name: 1 Shanghai Center for Systems Biomedicine, Shanghai Jiao Tong University, Key Laboratory of Systems Biomedicine, Shanghai 200240, China; Email: minjuanxu@sjtu.edu.cn (M.-J.X.); aoping@sjtu.edu.cn (P.A.)
– name: 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
– name: 5 State Key Laboratory of Natural and Biomimetic Drugs, Peking University, Beijing 100191, China; Email: ldddddd@yahoo.cn (D.L.); lxmdyt112@sina.com (X.-M.L.); whlin@bjmu.edu.cn (W.-H.L.)
– name: 4 State Key Laboratory of Microbial Metabolism and School of Life Science & Biotechnology, Shanghai JiaoTong University, Shanghai 200240, China; Email: yileizhao@sjtu.edu.cn (Y.-L.Z.); bao2lu@gmail.com (Z.-H.X.)
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Keywords anti-contractile capacity
anti-fibrosis
fibroblast
mangrove
benzopyran
Streptomyces xiamenensis
Language English
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This article is an open-access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
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These authors contributed equally to this work.
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SSID ssj0035894
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Snippet An anti-fibrotic compound produced by Streptomyces xiamenensis, found in mangrove sediments, was investigated for possible therapeutic effects against...
An anti-fibrotic compound produced by Streptomycesn xiamenensis, found in mangrove sediments, was investigated for possible therapeutic effects against...
An anti-fibrotic compound produced by Streptomycesn xiamenensis , found in mangrove sediments, was investigated for possible therapeutic effects against...
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SourceType Open Website
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Index Database
Enrichment Source
StartPage 639
SubjectTerms anti-contractile capacity
anti-fibrosis
benzopyran
Benzopyrans - isolation & purification
Benzopyrans - pharmacology
Biological effects
Carbonyl compounds
Cell Adhesion - drug effects
Cell Line
Cell Line, Tumor
Cell Proliferation - drug effects
Chromatography, High Pressure Liquid
Collagen - chemistry
fibroblast
Fibroblasts - drug effects
Fibrosis - drug therapy
Geologic Sediments - microbiology
Humans
Hydrolysis
Indicators and Reagents
Leukemia
Magnetic Resonance Spectroscopy
mangrove
Marine
Molecular Conformation
Streptomyces
Streptomyces - growth & development
Streptomyces - metabolism
Streptomyces xiamenensis
Trees - microbiology
Xiamenensis
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Title Identification and Characterization of an Anti-Fibrotic Benzopyran Compound Isolated from Mangrove-Derived Streptomyces xiamenensis
URI https://www.ncbi.nlm.nih.gov/pubmed/22611360
https://www.proquest.com/docview/1536000886
https://www.proquest.com/docview/1011213643
https://www.proquest.com/docview/1015247057
https://pubmed.ncbi.nlm.nih.gov/PMC3347021
https://doaj.org/article/6b043d4e30b14039987db0329eb8cb26
Volume 10
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