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DOI: 10.1055/s-2002-20263
© Georg Thieme Verlag Stuttgart · New York
Effects of Naturally Occurring Isoflavones on Prostaglandin E2 Production
Publikationsverlauf
March 1, 2001
July 22, 2001
Publikationsdatum:
22. Februar 2002 (online)
Abstract
Previously, we reported that the isoflavones tectorigenin and tectoridin, a glycosylated tectorigenin, isolated from the rhizomes of Belamcanda chinensis have an activity to inhibit prostaglandin (PG) E2 production in 12-O-tetradecanoylphorbol 13-acetate (TPA)-stimulated rat peritoneal macrophages. The inhibitory effect of tectorigenin is more potent than that of tectoridin. In this study, we investigated the structure-activity relationship of various isoflavones in the inhibition of PGE2 production in TPA-stimulated rat peritoneal macrophages. The isoflavones examined were isolated from the rhizomes of B. chinensis, and the flowers and the rhizomes of Pueraria thunbergiana. The order of potency to inhibit PGE2 production was as follows; irisolidone, tectorigenin > genistein > tectoridin (tectorigenin 7-glucoside), glycitein > daidzein. Kakkalide (irisolidone 7-xylosylglucoside), glycitin (glycitein 7-glucoside), daidzin (daidzein 7-glucoside), puerarin (daizein 8-glucoside), and genistin (genistein 7-glucoside) showed no significant inhibition. These findings indicated that 6-methoxylation and 5-hydroxylation increase the potency to inhibit PGE2 production and 7-O-glycosylation decreases the inhibitory activity.
Abbreviations
COX:cyclooxygenase
PG:prostaglandin
PTK:protein tyrosine kinase
TPA:12-O-tetradecanoylphorbol 13-acetate
Abstract
Previously, we reported that the isoflavones tectorigenin and tectoridin, a glycosylated tectorigenin, isolated from the rhizomes of Belamcanda chinensis have an activity to inhibit prostaglandin (PG) E2 production in 12-O-tetradecanoylphorbol 13-acetate (TPA)-stimulated rat peritoneal macrophages. The inhibitory effect of tectorigenin is more potent than that of tectoridin. In this study, we investigated the structure-activity relationship of various isoflavones in the inhibition of PGE2 production in TPA-stimulated rat peritoneal macrophages. The isoflavones examined were isolated from the rhizomes of B. chinensis, and the flowers and the rhizomes of Pueraria thunbergiana. The order of potency to inhibit PGE2 production was as follows; irisolidone, tectorigenin > genistein > tectoridin (tectorigenin 7-glucoside), glycitein > daidzein. Kakkalide (irisolidone 7-xylosylglucoside), glycitin (glycitein 7-glucoside), daidzin (daidzein 7-glucoside), puerarin (daizein 8-glucoside), and genistin (genistein 7-glucoside) showed no significant inhibition. These findings indicated that 6-methoxylation and 5-hydroxylation increase the potency to inhibit PGE2 production and 7-O-glycosylation decreases the inhibitory activity.
Abbreviations
COX:cyclooxygenase
PG:prostaglandin
PTK:protein tyrosine kinase
TPA:12-O-tetradecanoylphorbol 13-acetate
Key words
Belamcanda chinensis - Iridaceae - isoflavones - macrophage - prostaglandin E2 - Pueraria thunbergiana - Leguminosae - 12-O-tetradecanoylphorbol 13-acetate
Key words
Belamcanda chinensis - Iridaceae - isoflavones - macrophage - prostaglandin E2 - Pueraria thunbergiana - Leguminosae - 12-O-tetradecanoylphorbol 13-acetate
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Prof. Dr. Kazuo Ohuchi
Laboratory of Pathophysiological Biochemistry
Graduate School of Pharmaceutical Sciences
Tohoku University
Aoba Aramaki
Aoba-ku
Sendai
Miyagi 980-8578
Japan
eMail: ohuchi-k@mail.pharm.tohoku.ac.jp
Fax: +81-22-217-6859