JBIR-56 and JBIR-57, 2(1 H)-pyrazinones from a marine sponge-derived streptomyces sp. SpD081030SC-03

Keiichiro Motohashi, Kennichi Inaba, Shinichiro Fuse, Takayuki Doi, Miho Izumikawa, Shams Tabrez Khan, Motoki Takagi, Takashi Takahashi, Kazuo Shin-Ya

Research output: Contribution to journalArticlepeer-review

30 Citations (Scopus)

Abstract

Strain SpD081030SC-03, representing a novel species of Streptomyces, was isolated from a marine sponge. Two 3,5,6-trisubstituted 2(1H)-pyrazinones, JBIR-56 (1) and JBIR-57 (2), were isolated from a culture of SpD081030SC-03. The planar structures of 1 and 2 were assigned on the basis of extensive NMR and MS analyses. In addition, analyses of the methylated derivative of 1 confirmed a 3,5,6-trisubstituted 2(1H)-pyrazinone moiety. The absolute configurations of the amino acid residues were determined by application of Marfey's method. Because 1 did not appear to comprise the normal connection of amino acid units, we confirmed its structure by the total synthesis of 1. Biosynthetically, 1 consists of a unique skeleton connected to the peptide chain at C-5 of the pyrazinone ring.

Original languageEnglish
Pages (from-to)1630-1635
Number of pages6
JournalJournal of Natural Products
Volume74
Issue number7
DOIs
Publication statusPublished - 2011 Jul 22

ASJC Scopus subject areas

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

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