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Terfestatins B and C, New p-Terphenyl Glycosides Produced by Streptomyces sp. RM-5-8.

ABSTRACT: Terfestatins B (1) and C (2), new p-terphenyls bearing a novel unsaturated hexuronic acid (4-deoxy-?-L-threo-hex-4-enopyranuronate), a unique ?-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'-?-D-glucuronide from Streptomyces sp. RM-5-8) revealed 1 as potently neuroprotective, highlighting a new potential application of the terfestatin scaffold.

SUBMITTER: Wang X

PROVIDER: S-EPMC4472964 | biostudies-literature | 2015 Jun

REPOSITORIES: biostudies-literature

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Terfestatins B and C, New p-Terphenyl Glycosides Produced by Streptomyces sp. RM-5-8.

Wang Xiachang X Reynolds Anna R AR Elshahawi Sherif I SI Shaaban Khaled A KA Ponomareva Larissa V LV Saunders Meredith A MA Elgumati Ibrahim S IS Zhang Yinan Y Copley Gregory C GC Hower James C JC Sunkara Manjula M Morris Andrew J AJ Kharel Madan K MK Van Lanen Steven G SG Prendergast Mark A MA Thorson Jon S JS

Organic letters 20150511 11

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 ...[more]

PMID: 25961722

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