title: Anti-babesial ellagic acid rhamnosides from the bark of Elaeocarpus parvifolius.
abstract: Bioassay-guided investigation of the bark of Elaeocarpus parvifolius led to the isolation of three new ellagic acid derivatives, 4-O-methylellagic acid 3'-alpha-rhamnoside (2), 4-O-methylellagic acid 3'-(3''-O-acetyl)-alpha-rhamnoside (3), and 4-O-methylellagic acid 3'-(4''-O-acetyl)-alpha-rhamnoside (4) in addition to the known ellagic acid derivative, 4-O-methylellagic acid 3'-(2'',3''-di-O-acetyl)-alpha-rhamnoside (1). Their structures were elucidated on the basis of analysis of 1H NMR, 13C NMR, HMQC, HMBC and MS spectroscopic data. Compounds 1-4 were evaluated for their growth-inhibitory effect on Babesia gibsoni in vitro. Compounds 2 and 4 showed very weak activity, while compounds 1 and 3 showed moderate activity, with IC50 values of 28.5 and 52.1 microg/ml, respectively.
authors.affiliation: Laboratory of Bioorganic Chemistry, Division of Applied Bioscience, Graduate School of Agriculture, Hokkaido University, Sapporo 060-8589, Japan.
authors.forename: A
authors.initials: A
authors.lastname: Elkhateeb
authors.lastname: Subeki
authors.forename: K
authors.initials: K
authors.lastname: Takahashi
authors.forename: H
authors.initials: H
authors.lastname: Matsuura
authors.forename: M
authors.initials: M
authors.lastname: Yamasaki
authors.forename: O
authors.initials: O
authors.lastname: Yamato
authors.forename: Y
authors.initials: Y
authors.lastname: Maede
authors.forename: K
authors.initials: K
authors.lastname: Katakura
authors.forename: T
authors.initials: T
authors.lastname: Yoshihara
authors.forename: K
authors.initials: K
authors.lastname: Nabeta
mesh_terms: D000818:Animals; D000981:Antiprotozoal Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D001403:Babesia / Q000187:drug effects*; D045467:Elaeocarpaceae / Q000737:chemistry*; D004610:Ellagic Acid / Q000031:analogs & derivatives / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D015394:Molecular Structure; D024301:Plant Bark / Q000737:chemistry*
chemical_list: C511750:4-O-methylellagic acid 3'-(3''-O-acetyl)-alpha-rhamnoside; C511748:4-O-methylellagic acid 3'-(4''-O-acetyl)-alpha-rhamnoside; C511749:4-O-methylellagic acid 3'-alpha-rhamnoside; D000981:Antiprotozoal Agents; D004610:Ellagic Acid