Herbimycins D-F, ansamycin analogues from streptomyce s sp. RM-7-15

Khaled A. Shaaban, Xiachang Wang, Sherif I. Elshahawi, Larissa V. Ponomareva, Manjula Sunkara, Gregory C. Copley, James C. Hower, Andrew J. Morris, Madan K. Kharel, Jon S. Thorson

Research output: Contribution to journalArticlepeer-review

35 Scopus citations

Abstract

Bacterial strains belonging to the class actinomycetes were isolated from the soil near a thermal vent of the Ruth Mullins coal fire (Appalachian Mountains of eastern Kentucky). High-resolution electrospray ionization mass spectrometry and ultraviolet absorption profiles of metabolites from one of the isolates (Streptomyces sp. RM-7-15) revealed the presence of a unique set of metabolites ultimately determined to be herbimycins D-F (1-3). In addition, herbimycin A (4), dihydroherbimycin A (TAN 420E) (7), and the structurally distinct antibiotic bicycylomycin were isolated from the crude extract of Streptomyces sp. RM-7-15. Herbimycins A and D-F (1-3) displayed comparable binding affinities to the Hsp90α. While the new analogues were found to be inactive in cancer cell cytotoxicity and antimicrobial assays, they may offer new insights in the context of nontoxic ansamycin-based Hsp90 inhibitors for the treatment of neurodegenerative disease.

Original languageEnglish
Pages (from-to)1619-1626
Number of pages8
JournalJournal of Natural Products
Volume76
Issue number9
DOIs
StatePublished - Sep 27 2013

ASJC Scopus subject areas

  • Analytical Chemistry
  • Molecular Medicine
  • Pharmacology
  • Pharmaceutical Science
  • Drug Discovery
  • Complementary and alternative medicine
  • Organic Chemistry

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