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
Hauptverfasser: 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
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Sprache:eng
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Zusammenfassung: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.
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.5b01203