Chalcones and other compounds from the exudates of Angelica keiskei and their cancer chemopreventive effects.
Three new chalcones, xanthoangelol I (1), xanthoangelol J (2), and deoxydihydroxanthoangelol H (3), were isolated from an ethyl acetate-soluble fraction of exudates of the stems of Angelica keiskei, and their structures were established on the basis of spectroscopic methods. Nine aromatic compounds of known structure, 4-12, and a diacetylene, 13, were also isolated and identified from this same fraction. On evaluation of these compounds for their inhibitory effects on the induction of Epstein-Barr virus early antigen (EBV-EA) by 12-O-tetradecanoylphorbol-13-acetate (TPA) in Raji cells, 1, 2, 4, and 9-12 showed potent inhibitory effects on EBV-EA induction. In addition, upon evaluation of the inhibitory effects against activation of (+/-)-(E)-methyl-2[(E)-hydroxyimino]-5-nitro-6-methoxy-3-hexemide (NOR 1), a nitrogen oxide (NO) donor, six compounds, namely, 1, 2, 4, 9, 11, and 12, exhibited potent inhibitory effects. Further, isobavachalcone (4) exhibited inhibitory effects on skin tumor promotion in an in vivo two-stage mouse skin carcinogenesis test using 7,12-dimethylbenz[a]anthracene (DMBA) as an initiator and TPA as a promoter.
Akihisa
Toshihiro
T
College of Science and Technology, Nihon University, 1-8 Kanda Surugadai, Tokyo 101-8308, Japan. akihisa@chem.cst.nihon-u.ac.jp
Tokuda
Harukuni
H
Hasegawa
Daisuke
D
Ukiya
Motohiko
M
Kimura
Yumiko
Y
Enjo
Fumio
F
Suzuki
Takashi
T
Nishino
Hoyoku
H
D029969:Angelica / Q000737:chemistry*; D016588:Anticarcinogenic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000956:Antigens, Viral / Q000096:biosynthesis / Q000187:drug effects; D047188:Chalcones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D006801:Humans; D007214:Indonesia; D015394:Molecular Structure; D010946:Plants, Medicinal / Q000737:chemistry*
D016588:Anticarcinogenic Agents; D000956:Antigens, Viral; D047188:Chalcones; C033305:Epstein-Barr virus early antigen; C508537:deoxydihydroxanthoangelol H; C508535:xanthoangelol I; C508536:xanthoangelol J