Isolation of potential cancer chemopreventive agents from Eriodictyon californicum.
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.
Liu
Y L
YL
Division of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, Ohio State University, Columbus 43210.
Ho
D K
DK
Cassady
J M
JM
Cook
V M
VM
Baird
W M
WM
D000818:Animals; D016588:Anticarcinogenic Agents / Q000302:isolation & purification* / Q000494:pharmacology; D001564:Benzo(a)pyrene / Q000378:metabolism; D002478:Cells, Cultured; D006224:Cricetinae; D004273:DNA, Neoplasm / Q000378:metabolism; D003864:Depression, Chemical; D005260:Female; D005419:Flavonoids / Q000302:isolation & purification* / Q000494:pharmacology; D010946:Plants, Medicinal / Q000737:chemistry*; D011247:Pregnancy
D016588:Anticarcinogenic Agents; D004273:DNA, Neoplasm; D005419:Flavonoids; D001564:Benzo(a)pyrene