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Identification of two novel anti-fibrotic benzopyran compounds produced by engineered strains derived from Streptomyces xiamenensis M1-94P that originated from deep-sea sediments
The benzopyran compound obtained by cultivating a mangrove-derived strain, Streptomyces xiamenensis strain 318, shows multiple biological effects, including anti-fibrotic and anti-hypertrophic scar properties. To increase the diversity in the structures of the available benzopyrans, by means of bios...
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Published in: | Marine drugs 2013-10, Vol.11 (10), p.4035-4049 |
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description | The benzopyran compound obtained by cultivating a mangrove-derived strain, Streptomyces xiamenensis strain 318, shows multiple biological effects, including anti-fibrotic and anti-hypertrophic scar properties. To increase the diversity in the structures of the available benzopyrans, by means of biosynthesis, the strain was screened for spontaneous rifampicin resistance (Rif), and a mutated rpsL gene to confer streptomycin resistance (Str), was introduced into the S. xiamenensis strain M1-94P that originated from deep-sea sediments. Two new benzopyran derivatives, named xiamenmycin C (1) and D (2), were isolated from the crude extracts of a selected Str-Rif double mutant (M6) of M1-94P. The structures of 1 and 2 were identified by analyzing extensive spectroscopic data. Compounds 1 and 2 both inhibit the proliferation of human lung fibroblasts (WI26), and 1 exhibits better anti-fibrotic activity than xiamenmycin. Our study presents the novel bioactive compounds isolated from S. xiamenensis mutant strain M6 constructed by ribosome engineering, which could be a useful approach in the discovery of new anti-fibrotic compounds. |
doi_str_mv | 10.3390/md11104035 |
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To increase the diversity in the structures of the available benzopyrans, by means of biosynthesis, the strain was screened for spontaneous rifampicin resistance (Rif), and a mutated rpsL gene to confer streptomycin resistance (Str), was introduced into the S. xiamenensis strain M1-94P that originated from deep-sea sediments. Two new benzopyran derivatives, named xiamenmycin C (1) and D (2), were isolated from the crude extracts of a selected Str-Rif double mutant (M6) of M1-94P. The structures of 1 and 2 were identified by analyzing extensive spectroscopic data. Compounds 1 and 2 both inhibit the proliferation of human lung fibroblasts (WI26), and 1 exhibits better anti-fibrotic activity than xiamenmycin. Our study presents the novel bioactive compounds isolated from S. xiamenensis mutant strain M6 constructed by ribosome engineering, which could be a useful approach in the discovery of new anti-fibrotic compounds.</description><identifier>ISSN: 1660-3397</identifier><identifier>EISSN: 1660-3397</identifier><identifier>DOI: 10.3390/md11104035</identifier><identifier>PMID: 24152563</identifier><language>eng</language><publisher>Switzerland: MDPI AG</publisher><subject>anti-fibrosis ; benzopyran ; Benzopyrans - chemistry ; Benzopyrans - pharmacology ; Fibroblasts - drug effects ; Fibrosis - drug therapy ; Geologic Sediments - chemistry ; Geologic Sediments - microbiology ; Humans ; Lung - drug effects ; Mutation - genetics ; ribosome engineering ; Ribosomes - genetics ; Streptomyces - chemistry ; Streptomyces - genetics ; Streptomyces xiamenensis ; Threonine - analogs & derivatives ; Threonine - chemistry ; Threonine - pharmacology</subject><ispartof>Marine drugs, 2013-10, Vol.11 (10), p.4035-4049</ispartof><rights>Copyright MDPI AG 2013</rights><rights>2013 by the authors; licensee MDPI, Basel, Switzerland. 2013</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c472t-64fdc2b807cd76f71379673c7a5e81d5fa1152aab03949fa4ce57cd70896b90e3</citedby><cites>FETCH-LOGICAL-c472t-64fdc2b807cd76f71379673c7a5e81d5fa1152aab03949fa4ce57cd70896b90e3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.proquest.com/docview/1535664457/fulltextPDF?pq-origsite=primo$$EPDF$$P50$$Gproquest$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.proquest.com/docview/1535664457?pq-origsite=primo$$EHTML$$P50$$Gproquest$$Hfree_for_read</linktohtml><link.rule.ids>230,314,727,780,784,885,25753,27924,27925,37012,37013,44590,53791,53793,75126</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/24152563$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>You, Zhong-Yuan</creatorcontrib><creatorcontrib>Wang, Ya-Hui</creatorcontrib><creatorcontrib>Zhang, Zhi-Gang</creatorcontrib><creatorcontrib>Xu, Min-Juan</creatorcontrib><creatorcontrib>Xie, Shu-Jie</creatorcontrib><creatorcontrib>Han, Tie-Sheng</creatorcontrib><creatorcontrib>Feng, Lei</creatorcontrib><creatorcontrib>Li, Xue-Gong</creatorcontrib><creatorcontrib>Xu, Jun</creatorcontrib><title>Identification of two novel anti-fibrotic benzopyran compounds produced by engineered strains derived from Streptomyces xiamenensis M1-94P that originated from deep-sea sediments</title><title>Marine drugs</title><addtitle>Mar Drugs</addtitle><description>The benzopyran compound obtained by cultivating a mangrove-derived strain, Streptomyces xiamenensis strain 318, shows multiple biological effects, including anti-fibrotic and anti-hypertrophic scar properties. To increase the diversity in the structures of the available benzopyrans, by means of biosynthesis, the strain was screened for spontaneous rifampicin resistance (Rif), and a mutated rpsL gene to confer streptomycin resistance (Str), was introduced into the S. xiamenensis strain M1-94P that originated from deep-sea sediments. Two new benzopyran derivatives, named xiamenmycin C (1) and D (2), were isolated from the crude extracts of a selected Str-Rif double mutant (M6) of M1-94P. The structures of 1 and 2 were identified by analyzing extensive spectroscopic data. Compounds 1 and 2 both inhibit the proliferation of human lung fibroblasts (WI26), and 1 exhibits better anti-fibrotic activity than xiamenmycin. Our study presents the novel bioactive compounds isolated from S. xiamenensis mutant strain M6 constructed by ribosome engineering, which could be a useful approach in the discovery of new anti-fibrotic compounds.</description><subject>anti-fibrosis</subject><subject>benzopyran</subject><subject>Benzopyrans - chemistry</subject><subject>Benzopyrans - pharmacology</subject><subject>Fibroblasts - drug effects</subject><subject>Fibrosis - drug therapy</subject><subject>Geologic Sediments - chemistry</subject><subject>Geologic Sediments - microbiology</subject><subject>Humans</subject><subject>Lung - drug effects</subject><subject>Mutation - genetics</subject><subject>ribosome engineering</subject><subject>Ribosomes - genetics</subject><subject>Streptomyces - chemistry</subject><subject>Streptomyces - genetics</subject><subject>Streptomyces xiamenensis</subject><subject>Threonine - analogs & derivatives</subject><subject>Threonine - chemistry</subject><subject>Threonine - pharmacology</subject><issn>1660-3397</issn><issn>1660-3397</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><sourceid>PIMPY</sourceid><sourceid>DOA</sourceid><recordid>eNpdks9u1DAQxiMEoqVw4QGQJS4IKWCvHTu5IFUVf1YqAgk4WxN7svUqsYPtFJbH4gnxsm1pOdkz85tPM5-mqp4y-orzjr6eLGOMCsqbe9Uxk5LWJa3u3_ofVY9S2tJCtJ14WB2tBGtWjeTH1e-1RZ_d4AxkFzwJA8k_AvHhEkcCpVIPro8hO0N69L_CvIvgiQnTHBZvE5ljsItBS_odQb9xHjGWKOUIzidiMbrLEg8xTORLjjjnMO0MJvLTwYQefXKJfGR1Jz6TfAGZhOiKCuTrJos41wmBJLSudOT0uHowwJjwydV7Un179_br2Yf6_NP79dnpeW2EWuVaisGaVd9SZaySg2JcdVJxo6DBltlmAFZMAOgp70Q3gDDY7FHadrLvKPKTan3QtQG2eo5ugrjTAZz-mwhxoyEWY0bUkkplWooCaC-ogZ5BM3BeDO-pkE1btN4ctOaln9CaskeE8Y7o3Yp3F3oTLjVvV5KJvcCLK4EYvi-Ysp5cMjiO4DEsSTMhmo4pRmVBn_-HbsMSfbFKs4Y3UhZUFerlgTIxpBRxuBmGUb0_K_3vrAr87Pb4N-j1HfE_BGXMFQ</recordid><startdate>20131022</startdate><enddate>20131022</enddate><creator>You, Zhong-Yuan</creator><creator>Wang, Ya-Hui</creator><creator>Zhang, Zhi-Gang</creator><creator>Xu, Min-Juan</creator><creator>Xie, Shu-Jie</creator><creator>Han, Tie-Sheng</creator><creator>Feng, Lei</creator><creator>Li, Xue-Gong</creator><creator>Xu, Jun</creator><general>MDPI AG</general><general>MDPI</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>3V.</scope><scope>7T7</scope><scope>7TN</scope><scope>7X7</scope><scope>7XB</scope><scope>88E</scope><scope>8FD</scope><scope>8FE</scope><scope>8FH</scope><scope>8FI</scope><scope>8FJ</scope><scope>8FK</scope><scope>ABUWG</scope><scope>AFKRA</scope><scope>AZQEC</scope><scope>BBNVY</scope><scope>BENPR</scope><scope>BHPHI</scope><scope>BKSAR</scope><scope>C1K</scope><scope>CCPQU</scope><scope>DWQXO</scope><scope>F1W</scope><scope>FR3</scope><scope>FYUFA</scope><scope>GHDGH</scope><scope>GNUQQ</scope><scope>H95</scope><scope>H99</scope><scope>HCIFZ</scope><scope>K9.</scope><scope>L.F</scope><scope>L.G</scope><scope>LK8</scope><scope>M0S</scope><scope>M1P</scope><scope>M7P</scope><scope>P64</scope><scope>PCBAR</scope><scope>PIMPY</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>PRINS</scope><scope>7X8</scope><scope>5PM</scope><scope>DOA</scope></search><sort><creationdate>20131022</creationdate><title>Identification of two novel anti-fibrotic benzopyran compounds produced by engineered strains derived from Streptomyces xiamenensis M1-94P that originated from deep-sea sediments</title><author>You, Zhong-Yuan ; Wang, Ya-Hui ; Zhang, Zhi-Gang ; Xu, Min-Juan ; Xie, Shu-Jie ; Han, Tie-Sheng ; Feng, Lei ; Li, Xue-Gong ; Xu, Jun</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c472t-64fdc2b807cd76f71379673c7a5e81d5fa1152aab03949fa4ce57cd70896b90e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>anti-fibrosis</topic><topic>benzopyran</topic><topic>Benzopyrans - 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Academic</collection><collection>PubMed Central (Full Participant titles)</collection><collection>Directory of Open Access Journals</collection><jtitle>Marine drugs</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>You, Zhong-Yuan</au><au>Wang, Ya-Hui</au><au>Zhang, Zhi-Gang</au><au>Xu, Min-Juan</au><au>Xie, Shu-Jie</au><au>Han, Tie-Sheng</au><au>Feng, Lei</au><au>Li, Xue-Gong</au><au>Xu, Jun</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Identification of two novel anti-fibrotic benzopyran compounds produced by engineered strains derived from Streptomyces xiamenensis M1-94P that originated from deep-sea sediments</atitle><jtitle>Marine drugs</jtitle><addtitle>Mar Drugs</addtitle><date>2013-10-22</date><risdate>2013</risdate><volume>11</volume><issue>10</issue><spage>4035</spage><epage>4049</epage><pages>4035-4049</pages><issn>1660-3397</issn><eissn>1660-3397</eissn><abstract>The benzopyran compound obtained by cultivating a mangrove-derived strain, Streptomyces xiamenensis strain 318, shows multiple biological effects, including anti-fibrotic and anti-hypertrophic scar properties. To increase the diversity in the structures of the available benzopyrans, by means of biosynthesis, the strain was screened for spontaneous rifampicin resistance (Rif), and a mutated rpsL gene to confer streptomycin resistance (Str), was introduced into the S. xiamenensis strain M1-94P that originated from deep-sea sediments. Two new benzopyran derivatives, named xiamenmycin C (1) and D (2), were isolated from the crude extracts of a selected Str-Rif double mutant (M6) of M1-94P. The structures of 1 and 2 were identified by analyzing extensive spectroscopic data. Compounds 1 and 2 both inhibit the proliferation of human lung fibroblasts (WI26), and 1 exhibits better anti-fibrotic activity than xiamenmycin. Our study presents the novel bioactive compounds isolated from S. xiamenensis mutant strain M6 constructed by ribosome engineering, which could be a useful approach in the discovery of new anti-fibrotic compounds.</abstract><cop>Switzerland</cop><pub>MDPI AG</pub><pmid>24152563</pmid><doi>10.3390/md11104035</doi><tpages>15</tpages><oa>free_for_read</oa></addata></record> |
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subjects | anti-fibrosis benzopyran Benzopyrans - chemistry Benzopyrans - pharmacology Fibroblasts - drug effects Fibrosis - drug therapy Geologic Sediments - chemistry Geologic Sediments - microbiology Humans Lung - drug effects Mutation - genetics ribosome engineering Ribosomes - genetics Streptomyces - chemistry Streptomyces - genetics Streptomyces xiamenensis Threonine - analogs & derivatives Threonine - chemistry Threonine - pharmacology |
title | Identification of two novel anti-fibrotic benzopyran compounds produced by engineered strains derived from Streptomyces xiamenensis M1-94P that originated from deep-sea sediments |
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