Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: aerial part
NCBI PubMed ID: 10923837Publication DOI: 10.1248/cpb.48.1039Journal NLM ID: 0377775Publisher: Pharmaceutical Society Of Japan
Correspondence: Yoshikawa M <shoyaku
mb.kyoto-phu.ac.jp>
Institutions: Kyoto Pharmaceutical University, Kyoto, Japan, Research and Development Division, Morishita Jintan Co., Ltd., Osaka, Japan
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 μM), diosmetin (2.9 μM), and kaempferol (0.56 μM). The estrogenic activities of these flavones are nearly equal to those of the isoflavones, daidzein (0.61 μM) and genistein (0.60 μM). The methanolic extract of parsley, apiin, and apigenin restored the uterus weight in ovariectomized mice when orally administered for consecutive 7 days.
flavone glycoside, phytoestrogen, Petroselinum crispum, 6"-acetylapiin, petroside, breast cancer cell line
Structure type: monomer
Location inside paper: p. 1040, Chart 1, structure 10
Trivial name: astragalin, kaempferol 3-O-glucoside
Compound class: glycoside, flavonoid glycoside, flavonol glycoside, flavone glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, NMR-2D, FAB-MS, TLC, ESI-MS, biological assays, HPLC, extraction, CC
Related record ID(s): 68827, 68828, 68829, 68830, 68831, 68833
NCBI Taxonomy refs (TaxIDs): 4043Reference(s) to other database(s): CCSD:
49928, CBank-STR:4070
Show glycosyltransferases
There is only one chemically distinct structure:
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