Isolation of Potential Cancer Chemopreventive Agents from Eriodictyon californicum

• Published in: Journal of natural products (Washington, D.C.) Vol. 55; no. 3; pp. 357 - 363
• Main Authors: Liu, Yong-Long, Ho, David K, Cassady, John M, Cook, Vanessa M, Baird, William M
• Format: Journal Article
• Language: English
• Published: Washington, DC American Chemical Society 01-03-1992; Glendale, AZ American Society of Pharmacognosy
• Subjects: AGENTES ANTINEOPLASTICOS; Animals; Anticarcinogenic Agents - isolation & purification; Anticarcinogenic Agents - pharmacology; ANTINEOPLASTIC AGENTS; Benzo(a)pyrene - metabolism; Biological and medical sciences; Cells, Cultured; Cricetinae; CULTIVO DE TEJIDOS; CULTURE DE TISSU; Depression, Chemical; DNA, Neoplasm - metabolism; EXTRACTOS VEGETALES; EXTRAIT D'ORIGINE VEGETALE; Female; FLAVONOIDE; FLAVONOIDES; FLAVONOIDS; Flavonoids - isolation & purification; Flavonoids - pharmacology; General pharmacology; HAMSTER; HAMSTERS; HYDROPHYLLACEAE; Medical sciences; MEDICAMENT CYTOSTATIQUE; Pharmacognosy. Homeopathy. Health food; Pharmacology. Drug treatments; PLANT EXTRACTS; Plants, Medicinal - chemistry; Pregnancy; TISSUE CULTURE; Prevention; Dicotyledones; Angiospermae; Plant origin; Isolation; Spermatophyta; Hydrophyllaceae; Malignant tumor; Anticarcinogen; Flavonoid
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np50081a012

Activity-based fractionation of Eriodictyon californicum resulted in the isolation of 12 flavonoids that inhibit the metabolism of the carcinogen benzo[a]pyrene by hamster embryo cells in tissue culture. One was identified as a new flavanone, 3'-methyl-4'-isobutyryleriodictoyol [1], on the basis of spectroscopic analysis and alkaline hydrolysis. The seven other active flavanones were identified as eriodictyol [2], homoeriodictyol [3], 5,4'-dihydroxy-6,7-dimethoxyflavanone [4], pinocembrin [5], sakuranetin [6], 5,7,4'-trihydroxy-6,3'-dimethoxyflavanone [7], and naringenin 4'-methyl ether [8]. Four active flavones were also isolated: cirsimaritin [9], chrysoeriol [10], hispidulin [11], and chrysin [12]. The high inhibition of benzo[a]pyrene metabolism and the activation of benzo[a]pyrene to ultimate carcinogenic DNA-binding metabolites by cirsimaritin and chrysoeriol at a concentration of only 10 micrograms/ml indicates that these flavones warrant further investigation in vivo as potential chemopreventive agents.