Antiplasmodial phenolic compounds from Piptadenia pervillei

• Published in: Planta medica Vol. 74; no. 4; pp. 417 - 421
• Main Authors: Ramanandraibe, V, Greillier, P, Martin, M.T, Deville, A, Joyeau, R, Ramanitrahasimbola, D, Mouray, E, Rasoanaivo, P, Mambu, L
• Format: Journal Article
• Language: English
• Published: Germany 01.03.2008
• Subjects: Animals; anticarcinogenic activity; Antimalarials - chemistry; Antimalarials - pharmacology; Antineoplastic Agents, Phytogenic - chemistry; Antineoplastic Agents, Phytogenic - pharmacology; antiprotozoal properties; catechin; Cell Line; chemical structure; cultured cells; cytotoxicity; Fabaceae - chemistry; Humans; Molecular Structure; phenolic compounds; Phenols - chemistry; phytochemicals; Piptadenia; Piptadenia pervillei; Plasmodium falciparum; Plasmodium falciparum - drug effects; spectral analysis; Madagascar
• ISSN: 0032-0943; 1439-0221
• DOI: 10.1055/s-2008-1034328

Piptadenia pervillei Vatke (Fabaceae) was selected from a screening programme devoted to the search of naturally-occuring antimalarial compounds from plants of Madagascar. Bioassay-guided fractionation of the ethyl acetate extract of the leaves led to the isolation of four phenolic compounds, (+)-catechin ( 1), (+)-catechin 5-gallate ( 2), (+)-catechin 3-gallate ( 3) and ethyl gallate ( 4). Structures were determined by NMR and mass spectroscopy. Compounds 2 and 3 displayed the highest in vitro activity against the chloroquine-resistant strain FcB1 of Plasmodium falciparum with IC (50) values of 1.2 microM and 1.0 microM, respectively, and no significant cytotoxicity against the human embryonic lung cells MRC-5 was measured (IC (50) values > 75 microM). Five analogues ( 5 - 9) of (+)-catechin 5-gallate ( 2) were synthesized and evaluated for their antiplasmodial activity.