Chem. Pharm. Bull., 48(7), 1039-1044, July 2000

Regular Articles

Medicinal Foodstuffs. XVIII.¹⁾ Phytoestrogens from the Aerial Part of Petroselinum crispum MILL. (PARSLEY) and Structures of 6"-Acetylapiin and a New Monoterpene Glycoside, Petroside

Masayuki YOSHIKAWA,^*,a Toshiaki UEMURA,^a Hiroshi SHIMODA,^a Akinobu KISHI,^a Yuzo KAWAHARA,^b and Hisashi MATSUDA^a

Kyoto Pharmaceutical University,^a Misasagi, Yamashina-ku, Kyoto 607-8414, Japan and Research and Development Division, Morishita Jintan Co., Ltd.,^b 1-1-30 Tamatsukuri, Chuo-ku, Osaka 540-8566, Japan.
Received January 31, 2000; accepted March 28, 2000

In the course of our screening for natural estrogenic compounds from Occidental medicinal herbs, the extracts of several herbs were found to show proliferative activity in MCF-7 (an estrogen-sensitive breast cancer cell line). Among these active herbs, the methanolic extract from the aerial parts of Petroselinum crispum (parsley) showed potent estrogenic activity, which was equal to that of isoflavone glycosides from soybean. Through bioassay-guided separation, we isolated several flavone glycosides and a new flavone glycoside, 6"-acetylapiin, with estrogenic activity together with a new monoterpene glucoside, petroside. The structures of 6"-acetylapiin and petroside were characterized by the chemical and physicochemical evidence. Estrogenic activities of these flavone glycosides were found to be enhanced by removal of their glycoside moieties. The EC₅₀ values (concentration needed to enhance the MCF-7 proliferation 50% compared to non-estrogen treated cell) of their aglycones are as follows, apigenin (1.0 mM), diosmetin (2.9 mM), and kaempferol (0.56 mM). The estrogenic activities of these flavones are nearly equal to those of the isoflavones, daidzein (0.61 mM) and genistein (0.60 mM). The methanolic extract of parsley, apiin, and apigenin restored the uterus weight in ovariectomized mice when orally administered for consecutive 7 days.

Key words phytoestrogen; Petroselinum crispum; 6"-acetylapiin; petroside; flavone glycoside; breast cancer cell line