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Title

Unguiculin A and Ptilomycalins E-H, Antimalarial Guanidine Alkaloids from the Marine Sponge Monanchora unguiculata

Authors
Campos, Pierre-Eric
Queiroz, Emerson F
Al-Mourabit, Ali
Frederich, Michel
Bordignon, Annélise
De Voogd, Nicole
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Published in Journal of Natural Products. 2017, vol. 80, no. 5, p. 1404-1410
Abstract Chemical study of the CH2Cl2-MeOH (1:1) extract from the sponge Monanchora unguiculata collected in Madagascar highlighted five new compounds, one acyclic guanidine alkaloid, unguiculin A (1) and four pentacyclic alkaloids, ptilomycalins E-H (2-5), along with four known compounds: crambescidin 800 (6) and crambescidin 359 (7), crambescidic acid (8), and fromiamycalin (9). Their structures were elucidated by 1D and 2D NMR spectra and HRESIMS data. All compounds were evaluated for their cytotoxicity against KB cells and their antiplasmodial activity. The new ptilomycalin E (2) and the mixture of the new ptilomycalins G (4) and H (5) showed promising cytotoxicity against KB cells with IC50 values of 0.85 and 0.92 μM, respectively. Ptilomycalin F (3) and fromiamycalin (9) exhibited promising activity against Plasmodium falciparum with IC50 values of 0.23 and 0.24 μM, respectively.
Keywords Alkaloids/chemistry/pharmacology/toxicityAnimalsAntimalarials/pharmacologyGuanidine/analogs & derivatives/chemistry/pharmacology/toxicityGuanidines/chemistry/pharmacology/toxicityHumansInhibitory Concentration 50KB CellsMadagascarMarine BiologyMolecular StructureNuclear Magnetic ResonanceBiomolecularPlasmodium falciparum/chemistry/drug effectsSpiro Compounds/chemistry/pharmacology/toxicity
Identifiers
PMID: 28368118
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Structures
Research group Phytochimie et produits naturels bioactifs
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CAMPOS, Pierre-Eric et al. Unguiculin A and Ptilomycalins E-H, Antimalarial Guanidine Alkaloids from the Marine Sponge Monanchora unguiculata. In: Journal of Natural Products, 2017, vol. 80, n° 5, p. 1404-1410. https://archive-ouverte.unige.ch/unige:116650

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Deposited on : 2019-04-25

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