Synthesis of entadamide A and entadamide B isolated from Entada phaseoloides and their inhibitory effects on 5-lipoxygenase.
Two new sulfur-containing amides, entadamide A (1) and entadamide B (2), isolated from the seeds of Entada phaseoloides, were synthesized by the addition reaction of methanethiol to propiolic acid (5) followed by condensation with ethanolamine by the use of dicyclohexylcarbadiimide. These compounds inhibited the 5-lipoxygenase activity of RBL-1 cells at 10(-4) g/ml. This finding suggests that entadamides A and B may be examples of a new type of antiinflammatory drug.
Ikegami
F
F
Sekine
T
T
Aburada
M
M
Fujii
Y
Y
Komatsu
Y
Y
Murakoshi
I
I
D000178:Acrylamides / Q000138:chemical synthesis* / Q000494:pharmacology; D000577:Amides / Q000138:chemical synthesis* / Q000494:pharmacology; D000818:Animals; D001091:Arachidonate Lipoxygenases / Q000037:antagonists & inhibitors*; D007887:Fabaceae / Q000032:analysis*; D007942:Leukemia, Experimental / Q000201:enzymology; D016859:Lipoxygenase Inhibitors; D010946:Plants, Medicinal; D051381:Rats
D000178:Acrylamides; D000577:Amides; D016859:Lipoxygenase Inhibitors; C061600:entadamide A; C061599:entadamide B; D001091:Arachidonate Lipoxygenases