Studies on the constituents of Pueraria lobata. III. Isoflavonoids and related compounds in the roots and the voluble stems.

Kinjo, Junei; Furusawa, Jun-ichi; Baba, Junko; Terauchi, Takashi; Yamasaki, Masaki; Nohara, Toshihiro

doi:10.1248/cpb.35.4846

Cited by 143 publications

(91 citation statements)

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“…This study demonstrates that the referred fraction is composed mainly of three compounds: the major one that represents 90.69% (by high-performance liquid chromatography) of the total mass is the most active one with respect to termination of pregnancy and identified as puerarin, an isoflavone glycoside reported in the literature (Kinjo et al 1987).…”

Section: Discussionmentioning

confidence: 61%

“…1D and 2D NMR and mass spectral studies identified the active compound as puerarin ( Fig. 1), an isoflavone glycoside reported in the literature (Kinjo et al 1987).…”

Section: Purification and Characterisation Of The Test Compoundmentioning

confidence: 76%

“…Their ethanolic extract and the n-BuOH fraction thereof are reported to have significant antifertility activity in rats, mice and hamsters and possess significant oestrogenic activity (Shukla 1996). This communication reports that the major and active constituent of the referred fraction is puerarin, an isoflavone glycoside (Kinjo et al 1987) that acts as selective oestrogen receptor modulator (SERM; Boue et al 2003). Boue et al (2003) demonstrated that puerarin is oestrogenic and exerts preferential agonist activity towards ERb.…”

Section: Introductionmentioning

confidence: 96%

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Puerarin, a selective oestrogen receptor modulator, disrupts pregnancy in rats at pre-implantation stage

Saha¹,

Saraswat²,

Chakraborty³

et al. 2012

Reproduction

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The tubers of Pueraria tuberosa have folkloric repute as emmenagogue. The n-BuOH fraction of the ethanolic extract of tubers exhibits significant antifertility activity in laboratory animals. The present investigation explored the active principle(s) of the tuber extract with reference to contragestive effects in rats and probed the possible mechanism of action. Bioactivity-guided fractionation identified puerarin as the major constituent that exerted pregnancy-terminating effects. Oral administration of puerarin at R300 mg/kg per day for days (D) 1-2 post-coitus resulted in complete implantation failure. Serum oestradiol levels during D2-D5 and progesterone (P 4 ) level on D5 remained unaffected, but the endometrial expression of oestrogen receptor a (ERa) and ERb was adversely modulated that disrupted the implantation-specific characteristic endometrial oestrogenic milieu. The eventual consequence was loss of endometrial receptivity characterised by down-regulation of the uterine expression of P 4 receptor (PR) and attenuation of endometrial expression of leukaemia inhibitory factor, vascular endothelial growth factor and cyclo-oxygenase-2, the three important signalling molecules involved in the process of implantation. Light microscopic examination of the embryos demonstrated no untoward effect of puerarin on the development of embryos until D4, but D5 blastocysts underwent gross morphological distortion. The findings taken together are interpreted to suggest that puerarin adversely impacts the uterine expression of ER and PR that disrupts the implantation-conducive uterine milieu and prevents implantation. In conclusion, puerarin may be envisaged as a prospective molecule that merits further exploration for the development of non-steroidal post-coital contraceptive for women.

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Section: Discussionmentioning

confidence: 61%

“…1D and 2D NMR and mass spectral studies identified the active compound as puerarin ( Fig. 1), an isoflavone glycoside reported in the literature (Kinjo et al 1987).…”

Section: Purification and Characterisation Of The Test Compoundmentioning

confidence: 76%

Section: Introductionmentioning

confidence: 96%

See 1 more Smart Citation

Puerarin, a selective oestrogen receptor modulator, disrupts pregnancy in rats at pre-implantation stage

Saha¹,

Saraswat²,

Chakraborty³

et al. 2012

Reproduction

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“…Convenient Zemplens deacetylation of 2 with sodium methoxide in methanol gave pure coumestrol, m. p. 368°C (LASCHOBER & KAPPE [1990] found 360°C). Both compounds 1 and 2 were fully characterized by 1 H-NMR spectra; chemical shifts and vicinal coupling constants corresponded to the data already published for coumestrol (TAKEYA & ITOKAWA 1982;KINJO et al 1987) or its diacetate 2 (LE- VAN 1984). The carbon signals in 13 C-NMR spectrum of both coumestrol and di-O-acetylcoumestrol were assigned for the first time using two-dimensional HMQC technique (Table 1).…”

Section: Synthesis and Identification Of Coumestrolmentioning

confidence: 59%

The determination of isoflavones and coumestrol by capillary electrophoresis

Moravcová¹,

Kleinová²

2001

Czech J. Food Sci.

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MORAVCOVÁ J., KLEINOVÁ T. (2001):The determination of isoflavones and coumestrol by capillary electrophoresis. Czech J. Food Sci., 19: 132138.The separation of six isoflavones (biochanin A, isoformononetin, formononetin, prunetin, daidzein and genistein) and coumestrol on an uncoated fused-silica capillary electrophoresis column was optimised using alkaline borate buffer as electrolyte and DAD detection. A baseline separation of all analytes except a pair, formononetin-biochanin A was achieved at pH 10.5 in 25 min. Detection limits were low (0.1 µg/ml) and the linearity of the detector response was established in the concentration range 0.4-60 µg/ml (180 µg/ml for coumestrol). Coumestrol was synthesized and the carbon signals in 13 C-NMR spectrum of both coumestrol and di-O-acetylcoumestrol were assigned for the first time using two-dimensional HMQC technique.

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“…Only small amount of the subdued peaks were observed, which showed the irregular characteristics of lecithin. This indicated that genistein might be relevant to lecithin and the effect undermined the crystalline characteristics of genistein [11][12][13].…”

Section: Discussionmentioning

confidence: 99%

Extraction and Purification of Fructus Sophorae Genistein and Physicochemical Properties of its Complex with Lecithin

Brad

Zhang

2017

MOJDDT

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Studies on the constituents of Pueraria lobata. III. Isoflavonoids and related compounds in the roots and the voluble stems.

Abstract: Two new isoflavone glycosides, the 8-C-apiosyl(1•¨6) glucosides of daidzein and genistein,

Cited by 143 publications

References 0 publications

Puerarin, a selective oestrogen receptor modulator, disrupts pregnancy in rats at pre-implantation stage

Puerarin, a selective oestrogen receptor modulator, disrupts pregnancy in rats at pre-implantation stage

The determination of isoflavones and coumestrol by capillary electrophoresis

Extraction and Purification of Fructus Sophorae Genistein and Physicochemical Properties of its Complex with Lecithin

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