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Study of Antimalarial Activity of Chemical Constituents from Diospyros quaesita
Author(s) -
Ma CuiYing,
Musoke Sebisubi Fred,
Tan Ghee Teng,
Sydara Kongmany,
Bouamanivong Somsanith,
Southavong Bounhoong,
Soejarto D. Doel,
Fong Harry H. S.,
Zhang HongJie
Publication year - 2008
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.200890209
Subject(s) - chemistry , traditional medicine , diospyros , chemical constituents , pharmacology , botany , chromatography , biology , medicine
Bioassay‐directed fractionation led to the isolation of seven compounds from a sample of the dried leaves, twigs, and branches of Diospyros quaesita Thw . (Ebenaceae). One of the isolates, betulinic acid 3‐caffeate ( 1 ), showed in vitro antimalarial activity against Plasmodium falciparum clones D 6 (chloroquine‐sensitive) and W 2 (chloroquine‐resistant) with IC 50 values of 1.40 and 0.98 μ M , respectively. Evaluation of compound 1 in the human oral epidermoid (KB) cancer cell line revealed cytotoxicity at ED 50 of 4.0 μ M . In an attempt to reduce the cytotoxicity of 1 , the acetylated derivative 1a and betulinic acid ( 1b ) were prepared. Of the seven isolates, diospyrosin ( 2 ) was determined to be a new neolignan. In addition to 1 , other known compounds isolated in this study were pinoresinol, lariciresinol, N ‐benzoyl‐ L ‐phenylalaninol, scopoletin, and poriferast‐5‐en‐3 β ,7 α ‐diol. The structure of 2 was elucidated based on spectroscopic data analysis including 1D‐ and 2D‐NMR, and HR‐ESI‐MS.