Palstimolide A: A Complex Polyhydroxy Macrolide with Antiparasitic Activity.
Cast your vote
You can rate an item by clicking the amount of stars they wish to award to this item.
When enough users have cast their vote on this item, the average rating will also be shown.
Your vote was cast
Thank you for your feedback
Thank you for your feedback
Siqueira-Neto, Jair L
Souza, Julia M
LaMonte, Gregory M
Smith, Jennifer E
Gerwick, William H
MetadataShow full item record
AbstractMarine 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 LRHSQMBC 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.
CitationMolecules. 2020 Mar 31;25(7). pii: molecules25071604. doi: 10.3390/molecules25071604.
AffiliationHIPS, Helmholtz-Institut für Pharmazeutische Forschung Saarland, Universitätscampus E8.1 66123 Saarbrücken, Germany.
JournalMolecules (Basel, Switzerland)
The following license files are associated with this item:
- Creative Commons
Except where otherwise noted, this item's license is described as Attribution-NonCommercial-ShareAlike 4.0 International
- Bastimolide A, a Potent Antimalarial Polyhydroxy Macrolide from the Marine Cyanobacterium Okeania hirsuta.
- Authors: Shao CL, Linington RG, Balunas MJ, Centeno A, Boudreau P, Zhang C, Engene N, Spadafora C, Mutka TS, Kyle DE, Gerwick L, Wang CY, Gerwick WH
- Issue date: 2015 Aug 21
- Bastimolide B, an Antimalarial 24-Membered Marine Macrolide Possessing a tert-Butyl Group.
- Authors: Shao CL, Mou XF, Cao F, Spadafora C, Glukhov E, Gerwick L, Wang CY, Gerwick WH
- Issue date: 2018 Jan 26
- Tutuilamides A-C: Vinyl-Chloride-Containing Cyclodepsipeptides from Marine Cyanobacteria with Potent Elastase Inhibitory Properties.
- Authors: Keller L, Canuto KM, Liu C, Suzuki BM, Almaliti J, Sikandar A, Naman CB, Glukhov E, Luo D, Duggan BM, Luesch H, Koehnke J, O'Donoghue AJ, Gerwick WH
- Issue date: 2020 Mar 20
- Design, synthesis and anti-malarial activities of synthetic analogs of biselyngbyolide B, a Ca<sup>2+</sup> pump inhibitor from marine cyanobacteria.
- Authors: Sato E, Morita M, Ogawa H, Iwatsuki M, Hokari R, Ishiyama A, Ōmura S, Iwasaki A, Suenaga K
- Issue date: 2018 Feb 1
- A Review Study on Macrolides Isolated from Cyanobacteria.
- Authors: Wang M, Zhang J, He S, Yan X
- Issue date: 2017 Apr 26