The native production of the sesquiterpene isopterocarpolone by Streptomyces sp. RM-14-6

Khaled A. Shaaban, Shanteri Singh, Sherif I. Elshahawi, Xiachang Wang, 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

18 Scopus citations

Abstract

We report the production, isolation and structure elucidation of the sesquiterpene isopterocarpolone from an Appalachian isolate Streptomyces species RM-14-6. While isopterocarpolone was previously put forth as a putative plant metabolite, this study highlights the first native bacterial production of isopterocarpolone and the first full characterisation of isopterocarpolone using 1D and 2D NMR spectroscopy and HR-ESI mass spectrometry. Considering the biosynthesis of closely related metabolites (geosmin or 5-epiaristolochene), the structure of isopterocarpolone also suggests the potential participation of one or more unique enzymatic transformations. In this context, this work also sets the stage for the elucidation of potentially novel bacterial biosynthetic machinery.

Original languageEnglish
Pages (from-to)337-339
Number of pages3
JournalNatural Product Research
Volume28
Issue number5
DOIs
StatePublished - Mar 4 2014

Bibliographical note

Funding Information:
This work was supported in part by the University of Kentucky College of Pharmacy, the University of Kentucky Markey Cancer Center and the National Center for Advancing Translational Sciences (No. UL1TR000117).

Keywords

  • bacteria
  • biosynthesis
  • cyclase
  • isoprenoid
  • natural products
  • terpene

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Plant Science
  • Organic Chemistry

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