Structures of new coumarins and antitumor-promoting activity of coumarins from Angelica edulis.
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.
Mizuno
A
A
Department of Pharmacognosy and Phytochemistry, Meiji College of Pharmacy, Tokyo, Japan.
Takata
M
M
Okada
Y
Y
Okuyama
T
T
Nishino
H
H
Nishino
A
A
Takayasu
J
J
Iwashima
A
A
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*
D000972:Antineoplastic Agents, Phytogenic; D003374:Coumarins; C089694:edulisin III; C089695:edulisin IV