Anti-babesial ellagic acid rhamnosides from the bark of Elaeocarpus parvifolius.
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.
Elkhateeb
A
A
Laboratory of Bioorganic Chemistry, Division of Applied Bioscience, Graduate School of Agriculture, Hokkaido University, Sapporo 060-8589, Japan.
Subeki
Takahashi
K
K
Matsuura
H
H
Yamasaki
M
M
Yamato
O
O
Maede
Y
Y
Katakura
K
K
Yoshihara
T
T
Nabeta
K
K
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*
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