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Bastimolide B, an antimalarial 24-membered marine macrolide possessing a tert-butyl group

TitleBastimolide B, an antimalarial 24-membered marine macrolide possessing a tert-butyl group
Publication TypeJournal Article
Year of Publication2018
AuthorsShao C.L, Mou X.F, Cao F., Spadafora C., Glukhov E., Gerwick L, Wang C.Y, Gerwick WH
JournalJournal of Natural Products
Volume81
Pagination211-215
Date Published2018/01
Type of ArticleArticle
ISBN Number0163-3864
Accession NumberWOS:000423778900027
Keywordscyanobacterium; macrolactone; natural-products; Pharmacology & Pharmacy; Plant Sciences
Abstract

We reported previously the discovery of the potent antimalarial 40-membered macrolide bastimolide A (1) from the tropical marine cyanobacterium Okeania hirsute. Continued investigation has led to the discovery of a new analogue, bastimolide B (2), a 24-membered polyhydroxy macrolide with a long aliphatic chain and unique terminal tertbutyl group. Its complete structure was determined by a combination of extensive spectroscopic methods and comparative analysis of its methanolysis products with those of bastimolide A. A methanolysis mechanism for bastimolide A is proposed, and one unexpected isomerization product of the C2-C3 double bond, 2-(E)-bastimolide A (3), was obtained. Bastimolide B (2) showed strong antimalarial activity against chloroquine-sensitive Plasmodium falciparum strain HB3. A preliminary investigation of the structure activity relationship based on six analogues revealed the importance of the double bond as well as the 1,3-diol and 1,3,5-triol functionalities.

DOI10.1021/acs.jnatprod.7b00917
Short TitleJ. Nat. Prod.
Student Publication: 
No
Research Topics: 
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