Terfestatins B and C, new p -terphenyl glycosides produced by streptomyces sp. RM-5-8

Xiachang Wang, Anna R. Reynolds, Sherif I. Elshahawi, Khaled A. Shaaban, Larissa V. Ponomareva, Meredith A. Saunders, Ibrahim S. Elgumati, Yinan Zhang, Gregory C. Copley, James C. Hower, Manjula Sunkara, Andrew J. Morris, Madan K. Kharel, Steven G. Van Lanen, Mark A. Prendergast, Jon S. Thorson

Research output: Contribution to journalArticlepeer-review

35 Scopus citations

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.

Original languageEnglish
Pages (from-to)2796-2799
Number of pages4
JournalOrganic Letters
Volume17
Issue number11
DOIs
StatePublished - Jun 5 2015

Bibliographical note

Publisher Copyright:
© 2015 American Chemical Society.

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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