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Palstimolide A: A Complex Polyhydroxy Macrolide with Antiparasitic Activity

Authors :
Lena Keller
Jair L. Siqueira-Neto
Julia M. Souza
Korina Eribez
Gregory M. LaMonte
Jennifer E. Smith
William H. Gerwick
Source :
Molecules, Vol 25, Iss 7, p 1604 (2020)
Publication Year :
2020
Publisher :
MDPI AG, 2020.

Abstract

Marine Cyanobacteria (blue-green algae) have been shown to possess an enormous potential to produce structurally diverse natural products that exhibit a broad spectrum of potent biological activities, including cytotoxic, antifungal, antiparasitic, antiviral, and antibacterial activities. Here, we report the isolation and structure determination of palstimolide A, a complex polyhydroxy macrolide with a 40-membered ring that was isolated from a tropical marine cyanobacterium collected at Palmyra Atoll. NMR-guided fractionation in combination with MS2-based molecular networking and isolation via HPLC yielded 0.7 mg of the pure compound. The small quantity isolated along with the presence of significant signal degeneracy in both the 1H and 13C-NMR spectra complicated the structure elucidation of palstimolide A. Various NMR experiments and solvent systems were employed, including the LR-HSQMBC experiment that allows the detection of long-range 1H–13C correlation data across 4-, 5-, and even 6-bonds. This expanded NMR data set enabled the elucidation of the palstimolide’s planar structure, which is characterized by several 1,5-disposed hydroxy groups as well as a tert-butyl group. The compound showed potent antimalarial activity with an IC50 of 223 nM as well as interesting anti-leishmanial activity with an IC50 of 4.67 µM.

Details

Language :
English
ISSN :
14203049
Volume :
25
Issue :
7
Database :
Directory of Open Access Journals
Journal :
Molecules
Publication Type :
Academic Journal
Accession number :
edsdoj.311fa457b813483b99c7cdb8fe3e30c0
Document Type :
article
Full Text :
https://doi.org/10.3390/molecules25071604