title: Structures of new coumarins and antitumor-promoting activity of coumarins from Angelica edulis.
abstract: From the fruits of Angelica edulis Miyabe (Umbelliferae), three new angular furanocoumarins, edulisin III (1), edulisin IV (2), and edulisin V (3), were isolated along with three known coumarins, 2'(S), 3'(R)-3'-isobutyryloxy-4'-acetoxy-2',3'-dihydrooroselol (4), edultin (5), and 2'(S),3'(R)-3'-senecioyloxy-4'-acetoxy-2',3'-dihydrooroselol (6), respectively. The structures of 1 and 2 were established to be 2'(S),3'(R)-3'-(2-methylbutyryloxy)-4'-acetoxy-2',3'-dihydrooro selol and 2'-(S),3'(R)-3'-propyryloxy-4'-acetoxy-2',3'-dihydrooroselol by chemical studies and spectral analyses. Coumarin 3 was proved to be 3'-(2-methylbutyryl-oxy)-4'-angeloyloxy-2',3'-dihydrooroselol++ + by chemical and spectral analyses and H-C COLOC. Coumarins 1-6 were examined for the effects on tumor-promotor induced phenomena in vitro. Among these coumarins, 3 showed the most potent inhibitory activity on 12-O-tetradecanoylphorbol 13-acetate (TPA)-stimulated 32Pi incorporation into phospholipids of cultured cells.
authors.affiliation: Department of Pharmacognosy and Phytochemistry, Meiji College of Pharmacy, Tokyo, Japan.
authors.forename: A
authors.initials: A
authors.lastname: Mizuno
authors.forename: M
authors.initials: M
authors.lastname: Takata
authors.forename: Y
authors.initials: Y
authors.lastname: Okada
authors.forename: T
authors.initials: T
authors.lastname: Okuyama
authors.forename: H
authors.initials: H
authors.lastname: Nishino
authors.forename: A
authors.initials: A
authors.lastname: Nishino
authors.forename: J
authors.initials: J
authors.lastname: Takayasu
authors.forename: A
authors.initials: A
authors.lastname: Iwashima
mesh_terms: D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry* / Q000494:pharmacology; D002849:Chromatography, Gas; D003374:Coumarins / Q000737:chemistry* / Q000494:pharmacology; D006367:HeLa Cells; D006801:Humans; D007564:Japan; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010946:Plants, Medicinal / Q000737:chemistry*
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D003374:Coumarins; C089694:edulisin III; C089695:edulisin IV