Estrogenic and Anti-estrogenic Activities of Cassia tora Phenolic Constituents

Abstract

Estrogen is a key regulator of the cellular processes involved in the development and maintenance of the reproductive function.1) Phytoestrogens are polyphenolic non-steroidal plant compounds with estrogen-like biological activity. Recently, an increasing number of epidemiological and experimental studies has suggested that the consumption of phytoestrogens may have a protective effect on estrogen-related conditions like menopause and estrogen related diseases such as prostate and breast cancers, osteoporosis and cardiovascular diseases.2) In our search for new phytoestrogens, the ethanolic extract of Cassia tora exhibited a significant stimulation of estrogen dependent MCF-7 cells, suggesting its estrogenic activity. Cassia tora L. (Fabaceae) is widely distributed in tropical Asian countries and its seeds have been used as a traditional medicine for constipation, asthenia, eye disease, hepatitis, diuretic, hemoglobin disorders and as an antidysenteric.3) Hypotensive activity of the seed extract has also been reported. 4,5) In India the plant is used for the treatment of snakebites and scorpion stings.6) The seeds were found to contain a diversity of phenolic constituents, i.e. anthraquinones, naphthopyrones, naphthalenes, hydroanthracenes and their glucosides.7-11) These phenolic constituents were reported to have various biological and pharmacological effects such as antibacterial, 11) antifungal, 12) antimutagenic, 13) hypolipidemic 14) and anti-allergic activities. 11)In addition, the aqueous extract of the seed 15) and naphthopyrones 9) and anthraquinones 10) isolated from the seeds exhibited hepatoprotective activity.In this study, the isolation of two new phenolic triglucosides from a 70% ethanol extract of Cassia tora seeds is reported. Furthermore, a naringinase pretreatment, as a mimic of the metabolic activity of gastro-intestinal flora, was carried out for the ethanolic extract of Cassia tora, and the biologically active principles of this extract were also investigated. ResultsThe 70% ethanolic extract of Cassia tora seeds significantly stimulated the proliferation of estrogen dependent MCF-7 cells indicating its possible estrogenic activity, which is significantly increased after being treated with naringinase (Table 1). The 70% ethanolic extract was fractionated on DIAON HP-20 to obtain 3 fractions (25% methanol, 50% methanol, 100% methanol). Estrogenic activity of these fractions was evaluated using MCF-7 cells before and after naringinase treatment ( Medicine; 1-3-6 Minatojima, Chuo-ku, Kobe 650-0045, Japan. Received May 16, 2007; accepted July 17, 2007 Through an estrogenic activity bioassay-guided fractionation of the 70% ethanolic extract of Cassia tora seeds two new phenolic triglucosides, torachrysone 8-2), along with seven known compounds were isolated. The structures of the new compounds were elucidated on the basis of spectroscopic and chemical evidence. The estrogenic activity of the fractions and the isolated compounds were investigated using the estrogen-dependent proliferation o...

Structure elucidation of a sodium salified anthraquinone from the seeds of Cassia obtusifolia by NMR technique assisted with acid–alkali titration

“…In addition, on the basis of comparison of their spectral data with those reported in the literatures, compounds 2-10 were determined as rubrofusarin-6-O-β-D-gentiobioside, [9,10] [11] obtusifolin-2-O-β-D-glucopyranoside, [12] aurantio-obtusin-6-O-β-D-glucopyranoside, [13] physcion-8-O-β-Dglucopyranoside, [14] [15,16] toralactone-9-O-β-D-gentiobioside, [17] aurantio-obtusin, [18] [17] respectively.…”

Reversible Antifertility Effect of Cassia tora Linn in Male Rats

“…The fruits of the plant were collected in the moths of September and October of 2010 and study was carried out at Department of Zoology, University of Rajasthan Jaipur, India. Cassia tora possess various medicinal and pharmacological activities these includes antihepatotoxic [13] , antiallergic [14] , antimutagenic [15] ., antifungal [16] , radical scavenging and antimicrobial [16][17][18][19][20][21][22][23][24][25] .The chemical constituent of the plant Cassia tora are rubrofusarin triglucoside, non rubrofusarin gentobioside, demethyl-flavasperone, genitobioside, torachrysone gentibioside, torachrysone tetraglucoside, tora chrysone apioglucoside, torachrysone, toralactone aloemodin, rhein, emodin, naphthalene, anthraquinone, methicillin-resistant [23][24][25][26] .…”

Preparation of Adamantyl and t-butyl Oximes Derivatives of 1,3- and 1,4- Dihydroxynaphthalene Diketone Tautomers

“…В работах [7][8][9] упоминается лишь о перспективных свойствах 1,3-диги-дроксинафталина вследствие специфичного расположения гидроксильных групп.…”