Terfestatins B and C, New p‑Terphenyl Glycosides Produced by Streptomyces sp. RM-5–8
Terfestatins B (1) and C (2), new p-terphenyls bearing a novel unsaturated hexuronic acid (4-deoxy-α-l-threo-hex-4-enopyranuronate), a unique β-d-glycosyl ester of 5-isoprenylindole-3-carboxylate (3) and the same rare sugar, and two new hygromycin precursors, were characterized as metabolites of the...
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| Veröffentlicht in: | Organic letters 2015-06, Vol.17 (11), p.2796-2799 |
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| creator | Wang, Xiachang Reynolds, Anna R Elshahawi, Sherif I Shaaban, Khaled A Ponomareva, Larissa V Saunders, Meredith A Elgumati, Ibrahim S Zhang, Yinan Copley, Gregory C Hower, James C Sunkara, Manjula Morris, Andrew J Kharel, Madan K Van Lanen, Steven G Prendergast, Mark A Thorson, Jon S |
| description | Terfestatins B (1) and C (2), new p-terphenyls bearing a novel unsaturated hexuronic acid (4-deoxy-α-l-threo-hex-4-enopyranuronate), a unique β-d-glycosyl ester of 5-isoprenylindole-3-carboxylate (3) and the same rare sugar, and two new hygromycin precursors, were characterized as metabolites of the coal mine fire isolate Streptomyces sp. RM-5–8. EtOH damage neuroprotection assays using rat hippocampal-derived primary cell cultures with 1, 2, 3 and echoside B (a terfestatin C-3′-β-d-glucuronide from Streptomyces sp. RM-5–8) revealed 1 as potently neuroprotective, highlighting a new potential application of the terfestatin scaffold. |
| doi_str_mv | 10.1021/acs.orglett.5b01203 |
| format | Article |
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RM-5–8</title><source>ACS Publications</source><source>MEDLINE</source><creator>Wang, Xiachang ; Reynolds, Anna R ; Elshahawi, Sherif I ; Shaaban, Khaled A ; Ponomareva, Larissa V ; Saunders, Meredith A ; Elgumati, Ibrahim S ; Zhang, Yinan ; Copley, Gregory C ; Hower, James C ; Sunkara, Manjula ; Morris, Andrew J ; Kharel, Madan K ; Van Lanen, Steven G ; Prendergast, Mark A ; Thorson, Jon S</creator><creatorcontrib>Wang, Xiachang ; Reynolds, Anna R ; Elshahawi, Sherif I ; Shaaban, Khaled A ; Ponomareva, Larissa V ; Saunders, Meredith A ; Elgumati, Ibrahim S ; Zhang, Yinan ; Copley, Gregory C ; Hower, James C ; Sunkara, Manjula ; Morris, Andrew J ; Kharel, Madan K ; Van Lanen, Steven G ; Prendergast, Mark A ; Thorson, Jon S</creatorcontrib><description>Terfestatins B (1) and C (2), new p-terphenyls bearing a novel unsaturated hexuronic acid (4-deoxy-α-l-threo-hex-4-enopyranuronate), a unique β-d-glycosyl ester of 5-isoprenylindole-3-carboxylate (3) and the same rare sugar, and two new hygromycin precursors, were characterized as metabolites of the coal mine fire isolate Streptomyces sp. RM-5–8. EtOH damage neuroprotection assays using rat hippocampal-derived primary cell cultures with 1, 2, 3 and echoside B (a terfestatin C-3′-β-d-glucuronide from Streptomyces sp. 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RM-5–8</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>Terfestatins B (1) and C (2), new p-terphenyls bearing a novel unsaturated hexuronic acid (4-deoxy-α-l-threo-hex-4-enopyranuronate), a unique β-d-glycosyl ester of 5-isoprenylindole-3-carboxylate (3) and the same rare sugar, and two new hygromycin precursors, were characterized as metabolites of the coal mine fire isolate Streptomyces sp. RM-5–8. EtOH damage neuroprotection assays using rat hippocampal-derived primary cell cultures with 1, 2, 3 and echoside B (a terfestatin C-3′-β-d-glucuronide from Streptomyces sp. RM-5–8) revealed 1 as potently neuroprotective, highlighting a new potential application of the terfestatin scaffold.</description><subject>Animals</subject><subject>cell culture</subject><subject>chemical reactions</subject><subject>chemical structure</subject><subject>coal</subject><subject>ethanol</subject><subject>Glucosides - chemistry</subject><subject>Glucuronides - chemistry</subject><subject>glycosides</subject><subject>Glycosides - chemistry</subject><subject>Hexuronic Acids - chemistry</subject><subject>metabolites</subject><subject>Molecular Structure</subject><subject>neuroprotective effect</subject><subject>Rats</subject><subject>Streptomyces</subject><subject>Streptomyces - chemistry</subject><subject>sugars</subject><subject>Terphenyl Compounds - chemistry</subject><issn>1523-7060</issn><issn>1523-7052</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFUctO3DAUtVARz34BUuVlF2TGdh5ONpXKqFAkoAimEjvrxr6BoEwc7KQoO34B9Q_5EoxmGLWbduUrn4fuuYeQA84mnAk-Be0n1t022PeTtGRcsHiD7PBUxJFkqfiwnjO2TXa9v2eMh59ii2yLtMi4FGKH3MzRVeh76OvW0yMKraGzQ3qBj7R7eXoOaHeH7djQk2bU1tcGPb101gwaDS1Het077Hq7GHUAfDehV-dR-vL0O98nmxU0Hj-u3j3y8_jbfPY9Ovtxcjr7ehZBIvM-4ohplYEQla54bEKMGCQwU0KheQ46yUsDWECaJ5IVnGeFNBKEMSZkydI43iNflr7dUC7QaGx7B43qXL0ANyoLtfobaes7dWt_qSSRosiSYPB5ZeDswxBOoRa119g00KIdvBJMsFwmnLH_UnmWZ0nYSxaBGi-p2lnvHVbrjThTb_WpUJ9a1adW9QXVpz_DrDXvfQXCdEl4U9_bwbXhtv-0fAVJU6ti</recordid><startdate>20150605</startdate><enddate>20150605</enddate><creator>Wang, Xiachang</creator><creator>Reynolds, Anna R</creator><creator>Elshahawi, Sherif I</creator><creator>Shaaban, Khaled A</creator><creator>Ponomareva, Larissa V</creator><creator>Saunders, Meredith A</creator><creator>Elgumati, Ibrahim S</creator><creator>Zhang, Yinan</creator><creator>Copley, Gregory C</creator><creator>Hower, James C</creator><creator>Sunkara, Manjula</creator><creator>Morris, Andrew J</creator><creator>Kharel, Madan K</creator><creator>Van Lanen, Steven G</creator><creator>Prendergast, Mark A</creator><creator>Thorson, Jon S</creator><general>American Chemical Society</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>7X8</scope><scope>7S9</scope><scope>L.6</scope><scope>5PM</scope></search><sort><creationdate>20150605</creationdate><title>Terfestatins B and C, New p‑Terphenyl Glycosides Produced by Streptomyces sp. RM-5–8</title><author>Wang, Xiachang ; Reynolds, Anna R ; Elshahawi, Sherif I ; Shaaban, Khaled A ; Ponomareva, Larissa V ; Saunders, Meredith A ; Elgumati, Ibrahim S ; Zhang, Yinan ; Copley, Gregory C ; Hower, James C ; Sunkara, Manjula ; Morris, Andrew J ; Kharel, Madan K ; Van Lanen, Steven G ; Prendergast, Mark A ; Thorson, Jon S</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a478t-1ee5f6a22fcf13db013a7a0dba9c18ac48bdae9a58470911697d7a2ddd1156533</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Animals</topic><topic>cell culture</topic><topic>chemical reactions</topic><topic>chemical structure</topic><topic>coal</topic><topic>ethanol</topic><topic>Glucosides - chemistry</topic><topic>Glucuronides - chemistry</topic><topic>glycosides</topic><topic>Glycosides - chemistry</topic><topic>Hexuronic Acids - chemistry</topic><topic>metabolites</topic><topic>Molecular Structure</topic><topic>neuroprotective effect</topic><topic>Rats</topic><topic>Streptomyces</topic><topic>Streptomyces - chemistry</topic><topic>sugars</topic><topic>Terphenyl Compounds - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Wang, Xiachang</creatorcontrib><creatorcontrib>Reynolds, Anna R</creatorcontrib><creatorcontrib>Elshahawi, Sherif I</creatorcontrib><creatorcontrib>Shaaban, Khaled A</creatorcontrib><creatorcontrib>Ponomareva, Larissa V</creatorcontrib><creatorcontrib>Saunders, Meredith A</creatorcontrib><creatorcontrib>Elgumati, Ibrahim S</creatorcontrib><creatorcontrib>Zhang, Yinan</creatorcontrib><creatorcontrib>Copley, Gregory C</creatorcontrib><creatorcontrib>Hower, James C</creatorcontrib><creatorcontrib>Sunkara, Manjula</creatorcontrib><creatorcontrib>Morris, Andrew J</creatorcontrib><creatorcontrib>Kharel, Madan K</creatorcontrib><creatorcontrib>Van Lanen, Steven G</creatorcontrib><creatorcontrib>Prendergast, Mark A</creatorcontrib><creatorcontrib>Thorson, Jon S</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>AGRICOLA</collection><collection>AGRICOLA - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Wang, Xiachang</au><au>Reynolds, Anna R</au><au>Elshahawi, Sherif I</au><au>Shaaban, Khaled A</au><au>Ponomareva, Larissa V</au><au>Saunders, Meredith A</au><au>Elgumati, Ibrahim S</au><au>Zhang, Yinan</au><au>Copley, Gregory C</au><au>Hower, James C</au><au>Sunkara, Manjula</au><au>Morris, Andrew J</au><au>Kharel, Madan K</au><au>Van Lanen, Steven G</au><au>Prendergast, Mark A</au><au>Thorson, Jon S</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Terfestatins B and C, New p‑Terphenyl Glycosides Produced by Streptomyces sp. RM-5–8</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2015-06-05</date><risdate>2015</risdate><volume>17</volume><issue>11</issue><spage>2796</spage><epage>2799</epage><pages>2796-2799</pages><issn>1523-7060</issn><issn>1523-7052</issn><eissn>1523-7052</eissn><abstract>Terfestatins B (1) and C (2), new p-terphenyls bearing a novel unsaturated hexuronic acid (4-deoxy-α-l-threo-hex-4-enopyranuronate), a unique β-d-glycosyl ester of 5-isoprenylindole-3-carboxylate (3) and the same rare sugar, and two new hygromycin precursors, were characterized as metabolites of the coal mine fire isolate Streptomyces sp. RM-5–8. EtOH damage neuroprotection assays using rat hippocampal-derived primary cell cultures with 1, 2, 3 and echoside B (a terfestatin C-3′-β-d-glucuronide from Streptomyces sp. RM-5–8) revealed 1 as potently neuroprotective, highlighting a new potential application of the terfestatin scaffold.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>25961722</pmid><doi>10.1021/acs.orglett.5b01203</doi><tpages>4</tpages><oa>free_for_read</oa></addata></record> |
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| identifier | ISSN: 1523-7060 |
| ispartof | Organic letters, 2015-06, Vol.17 (11), p.2796-2799 |
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| language | eng |
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| source | ACS Publications; MEDLINE |
| subjects | Animals cell culture chemical reactions chemical structure coal ethanol Glucosides - chemistry Glucuronides - chemistry glycosides Glycosides - chemistry Hexuronic Acids - chemistry metabolites Molecular Structure neuroprotective effect Rats Streptomyces Streptomyces - chemistry sugars Terphenyl Compounds - chemistry |
| title | Terfestatins B and C, New p‑Terphenyl Glycosides Produced by Streptomyces sp. RM-5–8 |
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