Catenulisporolides, Glycosylated Triene Macrolides from the Chemically Underexploited Actinomycete Catenulispora Species

Sangkeun Son, Young Soo Hong, Yushi Futamura, Mina Jang, Jae Kyoung Lee, Kyung Taek Heo, Sung Kyun Ko, Jung Sook Lee, Shunji Takahashi, Hiroyuki Osada, Jae Hyuk Jang*, Jong Seog Ahn

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

9 Citations (Scopus)

Abstract

New glycosylated 26-membered triene macrolides catenulisporolides, the first polyketide metabolites from Catenulispora species, were obtained by targeting slow-forming colonies on selection agar plates and applying long-term cultivation. Their structures, including the full stereochemistry, were defined by comprehensive spectroscopic and chemical methods and confirmed by bioinformatics analysis. Analysis of the genome sequence revealed the responsible biosynthetic gene cluster spanning ∼160 kbp, and feeding experiments with isotope-labeled precursors showed that isovaleric acid acts as a rare starter unit. Catenulisporolides exhibited antimalarial activities against resistant strains of Plasmodium falciparum, and enhanced activity was observed in semisynthetic derivatives.

Original languageEnglish
Pages (from-to)7234-7238
Number of pages5
JournalOrganic Letters
Volume20
Issue number22
DOIs
Publication statusPublished - 2018 Nov 16
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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