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

Emmanuel Tope Oluwabusola; Jioji N. Tabudravu; Khalid S. Al Maqbali; Frederick Annang; Guiomar  Pérez Moreno; Fernando Reyes; Marcel Jaspars

doi:10.1002/cbdv.202000335

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 language	English
Article number	2000335
Number of pages	9
Journal	Chemistry & Biodiversity
Volume	17
Issue number	10
Early online date	29 Sep 2020
DOIs	https://doi.org/10.1002/cbdv.202000335
Publication status	Published - Oct 2020

Keywords

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

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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Olobuwosa_etal_CB_Antiparasitic_VOR
© 2020 The Authors. Chemistry & Biodiversity Published by Wiley‐VHCA AG, Zurich, Switzerland This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited. https://creativecommons.org/licenses/by/4.0/
Final published version, 1.45 MBLicence: CC BY

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Antiparasitic Activity of Bromotyrosine Alkaloids and New Analogues Isolated from the Fijian Marine Sponge Aplysinella rhax. / Oluwabusola, Emmanuel Tope (Corresponding Author); Tabudravu, Jioji N. (Corresponding Author); Al Maqbali, Khalid S. et al.

In: Chemistry & Biodiversity, Vol. 17, No. 10, 2000335, 10.2020.

Research output: Contribution to journal › Article › peer-review

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

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. ",

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author = "Oluwabusola, {Emmanuel Tope} and Tabudravu, {Jioji N.} and {Al Maqbali}, {Khalid S.} and Frederick Annang and {P{\'e}rez Moreno}, Guiomar and Fernando Reyes and Marcel Jaspars",

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AU - Tabudravu, Jioji N.

AU - Al Maqbali, Khalid S.

AU - Annang, Frederick

AU - Pérez Moreno, Guiomar

AU - Reyes, Fernando

AU - Jaspars, Marcel

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AB - 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.

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KW - Chagas disease

KW - METABOLITES

KW - NATURAL-PRODUCTS

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KW - DRUGS

KW - DERIVATIVES

KW - ASSOCIATION

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SN - 1612-1880

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ER -

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

Abstract

Keywords

UN SDGs

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