Chemical Studies on the Oriental Plant Drugs. XX. The Constituents of Cassia tora L. (1). The Structure of Torachrysone

Shibata, Shoji; Morishita, Eisaku; Kaneda, Miyuki; Kimura, Yushiro; Takido, Michio; Takahashi, S.

doi:10.1248/cpb.17.454

Cited by 36 publications

(23 citation statements)

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“…(11) In addition, torachrysone (16) 19,20) and 6-hydroxymusizin (17) 16) were obtained through acid hydrolysis of their corresponding isolated glycosides 6 and 7. Finally, nor-rubrofusarin (18) and nor-toralactone (19) were obtained by the demethylation of compounds 14 and 15. The known compounds were identified by comparison with reported data, and the structures of the new compounds were determined as follows.…”

Section: Resultsmentioning

confidence: 99%

“…The electron spray ionization mass (ESI-MS) spectrum showed an [MϩH] ϩ ion peak at m/z 733. On the basis of its ESI-MS and elemental analysis data, compound 1 was assigned the molecular formula C 32 H 44 11,19,20) Moreover, the presence of three anomeric protons at d In the 13 C-NMR spectrum, the downfield shifted C-6Ј and C-3Љ at d C 68.8 and at d C 88.1, respectively, revealed the presence of 1→6 and 1→3 linkages among the three glucose molecules. 3,11) In the HMBC spectrum, 1 H-…”

Section: Estrogenic and Anti-estrogenic Activities Of Cassia Tora Phementioning

confidence: 99%

“…Yeast Two-Hybrid Assay In the yeast expressing ERa (Table 3), 6-hydroxymusizin 8-O-b-D-glucoside (6) showed estrogenic activity at 10 Ϫ4 M. In addition, 6-hydroxymusizin (17), nor-rubrofusarin (18) and nor-toralactone (19) showed a significant estrogenic activity at 10 Ϫ4 M. On the other hand, in the yeast expressing ERb, 6-hydroxymusizin 8-O-b-D-glucoside (6) showed estrogenic activity at 10 Ϫ4 M. An appreciable induction of b-galactosidase activity was observed for aurantio-obtusin (12), 6-hydroxymusizin (17) (Table 4). Anti-estrogenic Activity Using the estrogen-dependent MCF-7 cell proliferation and yeast two-hybrid assays, all the isolated compounds were tested for their anti-estrogenic activities at various concentrations.…”

Section: Estrogen-dependent Mcf-7 Cellsmentioning

confidence: 99%

“…In addition, a group of synthetic compounds (20)(21)(22)(23)(24), torachrysone (16), 6-hydroxymusizin (17), nor-rubrofusarin (18) and nortoralactone (19) (Fig. 2) were also investigated in order to study the structure activity requirements of these compounds.…”

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Estrogenic and Anti-estrogenic Activities of Cassia tora Phenolic Constituents

El-Halawany

Chung

Nakamura

et al. 2007

CHEMICAL & PHARMACEUTICAL BULLETIN

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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...

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Section: Resultsmentioning

confidence: 99%

Section: Estrogenic and Anti-estrogenic Activities Of Cassia Tora Phementioning

confidence: 99%

Section: Estrogen-dependent Mcf-7 Cellsmentioning

confidence: 99%

mentioning

confidence: 99%

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Estrogenic and Anti-estrogenic Activities of Cassia tora Phenolic Constituents

El-Halawany

Chung

Nakamura

et al. 2007

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…[3,4] Its seed contains emodin, chrysophanol, physion, rubrofusarine, two glycosides namely 8-Hydroxy-3-methyl anthraquinone -1-β -gentiobioside & rubrofusarin -6-β -gentiobioside and sitosterol. [5] It also contains three naphthopyrone glucosides like cassiaside, rubrofusarin -6-O-β-Dgentiobioside and toralactone -9-O-β-D--gentiobioside.…”

Section: Chemical Constituentsmentioning

confidence: 99%