Structures of New Coumarins and Antitumor-Promoting Activity of Coumarins from Angelica edulis ¹

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′-dihydrooroselol 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-methylbutyryloxy)-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.

Key words

Angelica edulis - Umbelliferae - edulisin III - edulisin IV - edulisin V - antitumor-promoting activity