Dudawalamides A-D, antiparasitic cyclic depsipeptides from the marine cyanobacterium Moorea producens

TitleDudawalamides A-D, antiparasitic cyclic depsipeptides from the marine cyanobacterium Moorea producens
Publication TypeJournal Article
Year of Publication2017
AuthorsAlmaliti J., Malloy K.L, Glukhov E., Spadafora C., Gutierrez M., Gerwick WH
JournalJournal of Natural Products
Volume80
Pagination1827-1836
Date Published2017/06
Type of ArticleArticle
ISBN Number0163-3864
Accession NumberWOS:000404322100015
Keywordsbiosynthesis; collection; cyclodepsipeptides; drug discovery; in-vitro; lyngbya-majuscula; natural-products; philinopsis-speciosa; plasmodium-falciparum; potent
Abstract

A family of 2,2-dimethyl-3-hydroxy-7-octynoic acid (Dhoya)-containing cyclic depsipeptides, named dudawalamides A-D (1-4), was isolated from a Papua New Guinean field collection of the cyanobacterium Moorea producens using bioassay-guided and spectroscopic approaches. The planar structures of dudawalamides A-D were determined by a combination of 1D and 2D NMR experiments and MS analysis, whereas the absolute configurations were determined by X-ray crystallography, modified Marfey's analysis, chiral-phase GCMS, and chiral-phase HPLC. Dudawalamides A-D possess a broad spectrum of antiparasitic activity with minimal mammalian cell cytotoxicity. Comparative analysis of the Dhoya-containing class of lipopeptides reveals intriguing structure-activity relationship features of these NRPS-PKS-derived metabolites and their derivatives.

DOI10.1021/acs.jnatprod.7b00034
Short TitleJ. Nat. Prod.
Student Publication: 
Yes
Research Topics: 
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