Antiparasitic Activity of Bromotyrosine Alkaloids and New Analogues Isolated from the Fijian Marine Sponge Aplysinella rhax

Emmanuel Tope Oluwabusola* (Corresponding Author), Jioji N. Tabudravu* (Corresponding Author), Khalid S. Al Maqbali, Frederick Annang, Guiomar Pérez Moreno, Fernando Reyes, Marcel Jaspars

*Corresponding author for this work

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Abstract

Ten bromotyrosine alkaloids were isolated and characterised from the marine sponge Aplysinella rhax (de Laubenfels 1954) collected from the Fiji Islands, which included one new bromotyrosine analogue, psammaplin P and two other analogues, psammaplin O and 3-bromo-2-hydroxy-5-(methoxycarbonyl)benzoic acid, which have not been previously reported from natural sources. HR-ESI-MS, 1D and 2D NMR spectroscopic methods were used in the elucidation of the compounds. Bisaprasin, a biphenylic dimer of psammaplin A, showed moderate activity with IC 50 at 19±5 and 29±6 μM against Trypanzoma cruzi Tulahuen C4, and the lethal human malaria species Plasmodium falciparum clone 3D7, respectively, while psammaplins A and D exhibited low activity against both parasites. This is the first report of the antimalarial and antitrypanosomal activity of the psammaplin-type compounds. Additionally, the biosynthesis hypotheses of three natural products were proposed.

Original languageEnglish
Article number2000335
Number of pages9
JournalChemistry & Biodiversity
Volume17
Issue number10
Early online date29 Sep 2020
DOIs
Publication statusPublished - Oct 2020

Keywords

  • psammaplin
  • chagas disease
  • bromotyrosine
  • malaria
  • sponge
  • Chagas disease
  • METABOLITES
  • NATURAL-PRODUCTS
  • PSAMMAPLIN
  • PSEUDOCERATINA-PURPUREA
  • DRUGS
  • DERIVATIVES
  • ASSOCIATION

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