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- Title
Palstimolide A: A Complex Polyhydroxy Macrolide with Antiparasitic Activity.
- Authors
Keller, Lena; Siqueira-Neto, Jair L.; Souza, Julia M.; Eribez, Korina; LaMonte, Gregory M.; Smith, Jennifer E.; Gerwick, William H.
- 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.
- Subjects
PALMYRA Atoll (Line Islands); ANTIPARASITIC agents; CYANOBACTERIA; NATURAL products; CORAL reefs &; islands; ANTIMALARIALS
- Publication
Molecules, 2020, Vol 25, Issue 7, p1604
- ISSN
1420-3049
- Publication type
Article
- DOI
10.3390/molecules25071604