Weakly Antimalarial Flavonol Arabinofuranosides from Calycolpus warszewiczianus

• Published in: Journal of natural products (Washington, D.C.) D.C.), 2006-05, Vol.69 (5), p.826-828
• Main Authors: Torres-Mendoza, D, González, J, Ortega-Barría, E, Heller, M.V, Capson, T.L, McPhail, K, Gerwick, W.H, Cubilla-Rios, L
• Format: Article
• Language: English
• Subjects: Animals; antimalarials; Antimalarials - chemistry; Antimalarials - isolation & purification; Antimalarials - pharmacology; Antiprotozoal Agents - chemistry; Antiprotozoal Agents - isolation & purification; Antiprotozoal Agents - pharmacology; arabinofuranosides; Arabinose - analogs & derivatives; Arabinose - chemistry; Arabinose - isolation & purification; Arabinose - pharmacology; Biological and medical sciences; Calycolpus warszewiczianus; chemical structure; Chloroquine - pharmacology; Dose-Response Relationship, Drug; Drug Resistance; flavonol arabinoside; flavonols; Flavonols - chemistry; Flavonols - isolation & purification; Flavonols - pharmacology; General pharmacology; human health; Leishmania mexicana; Leishmania mexicana - drug effects; Medical sciences; Molecular Structure; Myrtaceae; Myrtaceae - chemistry; Panama; Pharmacognosy. Homeopathy. Health food; Pharmacology. Drug treatments; Plants, Medicinal - chemistry; Plasmodium falciparum; Plasmodium falciparum - drug effects; spectral analysis; Trypanosoma cruzi; Trypanosoma cruzi - drug effects
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np050484i

Three new flavonol arabinosides (2-4) were isolated from the young leaves of Calycolpus warszewiczianus. The structures were determined as myricetin-3-O-alpha-L-3' '-acetylarabinofuranoside (2), myricetin-3-O-alpha-L-3' ',5' '-diacetylarabinofuranoside (3), and 5-galloylquercetin-3-O-alpha-L-arabinofuranoside (4). Molecular structures were elucidated using NMR spectroscopy in combination with IR and MS data. Two known compounds, myricetin-3-O-alpha-L-arabinofuranoside (1) and (-)-epi-catechin (5), were also isolated. The compounds were tested in vitro against a chloroquine-resistant strain of Plasmodium falciparum, Leishmania mexicana, and Trypanosoma cruzi parasites. Compound 4 demonstrated weak activity against a chloroquine-resistant strain of P. falciparum (14.5 microM), whereas none of the compounds demonstrated activity against L. mexicana and T. cruzi at the concentrations of 40 and 50 microg/mL, respectively, and no cytotoxicity was detected against mammalian cells below 100 microg/mL.