Chalcones, coumarins, and flavanones from the exudate of Angelica keiskei and their chemopreventive effects.
From an ethyl acetate-soluble fraction of the exudate obtained from the stems of Angelica keiskei (Umbelliferae), 17 compounds, viz. five chalcones (1-5), seven coumarins (6-12), three flavanones (13-15), one diacetylene (16), and one 5-alkylresorcinol (17), were isolated. These compounds were evaluated with respect to their inhibitory effects on the induction of Epstein-Barr virus early antigen (EBV-EA) by 12-O-tetradecanoylphorbol-13-acetate (TPA) in Raji cells, which is known to be a primary screening test for antitumor-promoters. With the exception of three compounds (10, 16, and 17), all other compounds tested showed potent inhibitory effects on EBV-EA induction (92-100% inhibition at 1x10(3)mol ratio/TPA). In addition, upon evaluation of these compounds for the inhibitory effects against activation of (+/-)-(E)-methyl-2-[(E)-hydroxy-imino]-5-nitro-6-methoxy-3-hexemide (NOR 1), a nitric oxide (NO) donor, as a primary screening test for antitumor-initiators, two chalcones (2 and 3) and six coumarins (6-11) exhibited potent inhibitory effects.
Akihisa
Toshihiro
T
College of Science and Technology, Nihon University, 1-8 Kanda Surugadai, Chiyoda-ku, Tokyo 101-8308, Japan. akihisa@chem.cst.nihon-u.ac.jp
Tokuda
Harukuni
H
Ukiya
Motohiko
M
Iizuka
Masao
M
Schneider
Stefan
S
Ogasawara
Kazuya
K
Mukainaka
Teruo
T
Iwatsuki
Kenji
K
Suzuki
Takashi
T
Nishino
Hoyoku
H
D029969:Angelica / Q000737:chemistry*; D016588:Anticarcinogenic Agents / Q000494:pharmacology; D000956:Antigens, Viral / Q000096:biosynthesis; D002051:Burkitt Lymphoma / Q000188:drug therapy / Q000378:metabolism; D002273:Carcinogens / Q000494:pharmacology; D002599:Chalcone / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D018890:Chemoprevention; D003374:Coumarins / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D004986:Ether; D044950:Flavanones / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D006801:Humans; D006898:Hydroxylamines / Q000378:metabolism; D015394:Molecular Structure; D020030:Nitric Oxide Donors / Q000378:metabolism; D010936:Plant Extracts / Q000737:chemistry / Q000494:pharmacology*; D018547:Plant Stems / Q000737:chemistry; D013755:Tetradecanoylphorbol Acetate / Q000494:pharmacology; D014407:Tumor Cells, Cultured / Q000187:drug effects
C477506:(+-)-E-4-methyl-2-((E)-hydroxylamino)-5-nitro-6-methoxy-3-hexanamide; D016588:Anticarcinogenic Agents; D000956:Antigens, Viral; D002273:Carcinogens; D003374:Coumarins; C033305:Epstein-Barr virus early antigen; D044950:Flavanones; D006898:Hydroxylamines; D020030:Nitric Oxide Donors; D010936:Plant Extracts; D004986:Ether; D002599:Chalcone; D013755:Tetradecanoylphorbol Acetate; C028610:flavanone