A cytotoxic principle of Tamarindus indica, di-n-butyl malate and the structure-activity relationship of its analogues.
Bioassay-guided fractionation of the methanolic extract of Tamarindus indica fruits led to the isolation of L-(-)-di-n-butyl malate which exhibited a pronounced cytotoxic activity against sea urchin embryo cells. In order to study structure-activity relationships, close-structure relatives of di-n-butyl malate were synthesized using D-(+)- and L-(-)-malic acid as starting materials, and their cytotoxic activities were examined for the sea urchin embryo assay. L-(-)-Di-n-pentyl malate was the most effective inhibitor to the development of the fertilized eggs. Significant inhibitory activity was not seen in the esters of D-(-)-isomer.
Kobayashi
A
A
Department of Biotechnology, Osaka University, Japan.
Adenan
M I
MI
Kajiyama
S
S
Kanzaki
H
H
Kawazu
K
K
D000818:Animals; D000900:Anti-Bacterial Agents; D000890:Anti-Infective Agents / Q000138:chemical synthesis / Q000302:isolation & purification* / Q000633:toxicity; D001230:Aspergillus / Q000187:drug effects; D001412:Bacillus subtilis / Q000187:drug effects; D001755:Blastocyst / Q000187:drug effects; D002963:Cladosporium / Q000187:drug effects; D003603:Cytotoxins / Q000138:chemical synthesis / Q000302:isolation & purification* / Q000633:toxicity; D004625:Embryo, Nonmammalian / Q000187:drug effects; D004926:Escherichia coli / Q000187:drug effects; D007887:Fabaceae; D009682:Magnetic Resonance Spectroscopy; D008293:Malates / Q000138:chemical synthesis / Q000302:isolation & purification* / Q000633:toxicity; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D010946:Plants, Medicinal; D012617:Sea Urchins; D013329:Structure-Activity Relationship
D000900:Anti-Bacterial Agents; D000890:Anti-Infective Agents; D003603:Cytotoxins; D008293:Malates; C099586:di-n-butylmalate; C030298:malic acid