2. Academic Validation
  3. Tropolone Ring Construction in the Biosynthesis of Rubrolone B, a Cationic Tropolone Alkaloid from Endophytic Streptomyces

Tropolone Ring Construction in the Biosynthesis of Rubrolone B, a Cationic Tropolone Alkaloid from Endophytic Streptomyces

  • Org Lett. 2016 Mar 18;18(6):1254-7. doi: 10.1021/acs.orglett.6b00074.
Yijun Yan 1,  Ya-Tuan Ma 1,  Jing Yang 1,  Geoff P Horsman 2,  Dan Luo 1,  Xu Ji 1,  Sheng-Xiong Huang 1
Affiliations

Affiliations

  • 1 State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences , Kunming 650201, China.
  • 2 Department of Chemistry & Biochemistry, Wilfrid Laurier University , Waterloo, ON N2L 3C5, Canada.
PMID: 26926531 DOI: 10.1021/acs.orglett.6b00074
Abstract

Rubrolones are tropolonoid Natural Products with a unique carbon skeleton. Extensive secondary metabolite analysis of the endophytic Streptomyces sp. KIB-H033 revealed a new class of rubrolone analogue possessing a rare benzoic acid-pyridine inner salt moiety. Precursor feeding with [(13)C]-acetate revealed a labeling pattern consistent with tropolone moiety construction via type-II PKS chemistry followed by complex oxidative rearrangements. This Bacterial biosynthetic route represents a surprising departure from Fungal tropolone assembly during stipitatic acid biosynthesis.

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