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

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 def...

Full description

Saved in:
Bibliographic Details
Published in:Organic letters 2018-11, Vol.20 (22), p.7234-7238
Main Authors: Son, Sangkeun, Hong, Young-Soo, Futamura, Yushi, Jang, Mina, Lee, Jae Kyoung, Heo, Kyung Taek, Ko, Sung-Kyun, Lee, Jung Sook, Takahashi, Shunji, Osada, Hiroyuki, Jang, Jae-Hyuk, Ahn, Jong Seog
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.8b03160