Chalcones, coumarins, and flavanones from the exudate of Angelica keiskei and their chemopreventive effects

• Published in: Cancer letters 2003-11, Vol.201 (2), p.133-137
• Main Authors: Akihisa, Toshihiro, Tokuda, Harukuni, Ukiya, Motohiko, Iizuka, Masao, Schneider, Stefan, Ogasawara, Kazuya, Mukainaka, Teruo, Iwatsuki, Kenji, Suzuki, Takashi, Nishino, Hoyoku
• Format: Article
• Language: English
• Subjects: Angelica; Angelica - chemistry; Angelica keiskei; Anticarcinogenic Agents - pharmacology; Antigens, Viral - biosynthesis; Antineoplastic agents; Antitumor-initiator; Antitumor-promoter; Biological and medical sciences; Burkitt Lymphoma - drug therapy; Burkitt Lymphoma - metabolism; Cancer; Carcinogens - pharmacology; Cell culture; Chalcone - chemistry; Chalcone - isolation & purification; Chalcone - pharmacology; Chalcones; Chemoprevention; Chemopreventive effects; Coumarins; Coumarins - chemistry; Coumarins - isolation & purification; Coumarins - pharmacology; Epstein-Barr virus; Ether; Flavanones; Flavanones - chemistry; Flavanones - isolation & purification; Flavanones - pharmacology; Humans; Hydroxylamines - metabolism; Medical research; Medical sciences; Molecular Structure; Nitric oxide; Nitric Oxide Donors - metabolism; Pharmacology. Drug treatments; Plant Extracts - chemistry; Plant Extracts - pharmacology; Plant Stems - chemistry; Rodents; Tetradecanoylphorbol Acetate - pharmacology; Tumor Cells, Cultured - drug effects; Tumors; Umbelliferae
• ISSN: 0304-3835; 1872-7980
• DOI: 10.1016/S0304-3835(03)00466-X

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 1×10 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.