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Antiparasitic Activity of Bromotyrosine Alkaloids and New Analogues Isolated from the Fijian Marine Sponge Aplysinella rhax
Author(s) -
Oluwabusola Emmanuel T.,
Tabudravu Jioji N.,
Al Maqbali Khalid S.,
Annang Frederick,
PérezMoreno Guiomar,
Reyes Fernando,
Jaspars Marcel
Publication year - 2020
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.202000335
Subject(s) - sponge , antiparasitic , chemistry , plasmodium falciparum , stereochemistry , dimer , depsipeptide , malaria , biology , organic chemistry , botany , medicine , pathology , immunology
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.