Glycitein

The fruits of Glycine max (L.) merr.

Glycitein is a soybean (yellow cultivar) isoflavonoid; used in combination with other isoflavonoids such as genistein and daidzein to study apoptosis and anti-oxidation processes.

References:
[1]. Song TT, et al. Estrogenic activity of glycitein, a soy isoflavone. J Agric Food Chem. 1999 Apr;47(4):1607-10. [2]. Yoshida H, et al. Glycitein effect on suppressing the proliferation and stimulating the differentiation of osteoblastic MC3T3-E1 cells. Biosci Biotechnol Biochem. 2001 May;65(5):1211-3. [3]. Pan W, et al. Genistein, daidzein and glycitein inhibit growth and DNA synthesis of aortic smooth muscle cells from stroke-prone spontaneously hypertensive rats. J Nutr. 2001 Apr;131(4):1154-8.

Inhibitory effects of glycitein on hydrogen peroxide induced cell damage by scavenging reactive oxygen species and inhibiting c-Jun N-terminal kinase.[Pubmed:17516245]

Free Radic Res. 2007 Jun;41(6):720-9.

The present study investigated the cytoprotective properties of Glycitein, a metabolite formed by the transformation of glycitin by intestinal microflora, against oxidative stress. Glycitein was found to scavenge intracellular reactive oxygen species (ROS), and 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical, and thereby preventing lipid peroxidation and DNA damage. Glycitein inhibited apoptosis of Chinese hamster lung fibroblast (V79-4) cells exposed to hydrogen peroxide (H(2)O(2)) via radical scavenging activity. Glycitein abrogated the activation of c-Jun N-terminal kinase (JNK) induced by H(2)O(2) treatment and inhibited DNA binding activity of activator protein-1 (AP-1), a downstream transcription factor of JNK. Taken together, these findings suggest that Glycitein protected H(2)O(2) induced cell death in V79-4 cells by inhibiting ROS generation and JNK activation.

Synthesis of beta-maltooligosaccharides of glycitein and daidzein and their anti-oxidant and anti-allergic activities.[Pubmed:20714292]

Molecules. 2010 Jul 29;15(8):5153-61.

The production of beta-maltooligosaccharides of Glycitein and daidzein using Lactobacillus delbrueckii and cyclodextrin glucanotransferase (CGTase) as biocatalysts was investigated. The cells of L. delbrueckii glucosylated Glycitein and daidzein to give their corresponding 4'- and 7-O-beta-glucosides. The beta-glucosides of Glycitein and daidzein were converted into the corresponding beta-maltooligosides by CGTase. The 7-O-beta-glucosides of Glycitein and daidzein and 7-O-beta-maltoside of Glycitein showed inhibitory effects on IgE antibody production. On the other hand, beta-glucosides of Glycitein and daidzein exerted 2,2-diphenyl-1-picrylhydrazyl (DPPH) free-radical scavenging activity and supeoxide-radical scavenging activity.

Glycitein inhibits glioma cell invasion through down-regulation of MMP-3 and MMP-9 gene expression.[Pubmed:20188714]

Chem Biol Interact. 2010 Apr 15;185(1):18-24.

Matrix metalloproteinases (MMPs) are zinc-dependent endopeptidases that play a pivotal role in invasion and angiogenesis of malignant glioma cells. Therefore, the inhibition of MMPs has been suggested to be a promising therapeutic strategy for brain tumors. In the present study, we found that Glycitein, a bacterial metabolite of the isoflavone glycitin, inhibits the expression of MMP-3 and MMP-9 at promoter, mRNA, and protein levels in PMA-stimulated U87MG human astroglioma cells. In addition, gelatin zymography showed that Glycitein inhibited the PMA-induced MMP-9 secretion in U87MG cells. A subsequent Matrigel invasion assay revealed that Glycitein suppresses the in vitro invasiveness of glioma cells, which may be at least partly due to the Glycitein-mediated inhibition of MMP-3 and MMP-9. In support of this, treatment of MMP-3- or MMP-9-specific inhibitor significantly suppressed PMA-induced invasion of glioma cells. Further mechanistic studies revealed that Glycitein inhibits the DNA binding and transcriptional activities of NF-kappaB and AP-1, which are important transcription factors for MMP-3 or MMP-9 gene expression. Furthermore, Glycitein suppresses PMA-induced phosphorylation of three types of MAP kinases, which are upstream signaling molecules in MMP gene expressions and NF-kappaB and AP-1 activities in glioma cells. Therefore, the inhibition of MMP-3 and MMP-9 expression by Glycitein may have therapeutic potential for controlling invasiveness of malignant gliomas.

Genistein, daidzein and glycitein inhibit growth and DNA synthesis of aortic smooth muscle cells from stroke-prone spontaneously hypertensive rats.[Pubmed:11285318]

J Nutr. 2001 Apr;131(4):1154-8.

Recent studies have reported that estrogen replacement therapy (ERT) reduces the risk of cardiovascular diseases in postmenopausal women. However, mechanisms responsible for this effect are not yet completely understood, and ERT is associated with carcinogenic side effects in women and feminizing effects in men. Because soybean isoflavones, a group of natural phytoestrogens, have only weak estrogenic activity and are not known to have side effects such as carcinogenesis and feminization, we evaluated the effects of genistein, daidzein and Glycitein on the growth and DNA synthesis of aortic smooth muscle cells (SMC) from stroke-prone spontaneously hypertensive rats (SHRSP). SMC were cultured in dishes and proliferated on 10% dextran-coated charcoal/fetal bovine serum, and then treated with 0.1-30 micromol/L of genistein, daidzein or Glycitein to investigate cell proliferation (cell number) and DNA synthesis (cell proliferation ELISA system), respectively. We also studied their effects on platelet-derived growth factor (PDGF)-BB (20 microg/L)-induced SMC proliferation. Soybean isoflavones inhibited proliferation and DNA synthesis of SMC from SHRSP in a concentration-dependent manner. Inhibition was significant at 3 micromol/L of genistein and 10 micromol/L of both daidzein and Glycitein. For significant inhibition of PDGF-BB-induced SMC proliferation, concentrations as low as 0.1 micromol/L of each isoflavone were effective. These isoflavones, with their inhibitory effects on natural and PDGF-BB-induced SMC proliferation, may be useful in attenuatating such proliferation, a basic mechanism involved in atherosclerotic vascular change, thereby preventing atherosclerotic cardiovascular diseases.

Glycitein activates extracellular signal-regulated kinase via vascular endothelial growth factor receptor signaling in nontumorigenic (RWPE-1) prostate epithelial cells.[Pubmed:17156992]

J Nutr Biochem. 2007 Aug;18(8):525-32.

Increased consumption of soy is associated with a decreased risk for prostate cancer; however, the specific cellular mechanisms responsible for this anticancer activity are unknown. Dietary modulation of signaling cascades controlling cellular growth, proliferation and differentiation has emerged as a potential chemopreventive mechanism. The present study examined the effects of four soy isoflavones (genistein, daidzein, Glycitein and equol) on extracellularsignal-regulated kinase (ERK1/2) activity in a nontumorigenic prostate epithelial cell line (RWPE-1). All four isoflavones (10 micromol/L) significantly increased ERK1/2 activity in RWPE-1 cells, as determined by immunoblotting. Isoflavone-induced ERK1/2 activation was rapid and sustained for approximately 2 h posttreatment. Glycitein, the most potent activator of ERK1/2, decreased RWPE-1 cell proliferation by 40% (P<.01). Glycitein-induced ERK1/2 activation was dependent, in part, on tyrosine kinase activity associated with vascular endothelial growth factor receptor (VEGFR). The presence of both VEGFR1 and VEGFR2 in the RWPE-1 cell line was confirmed by immunocytochemistry. Treatment of RWPE-1 cells with VEGF(165) resulted in transient ERK1/2 activation and increased cellular proliferation. The ability of isoflavones to modulate ERK1/2 signaling cascade via VEGFR signaling in the prostate may be responsible, in part, for the anticancer activity of soy.

Bioavailability of glycitein relatively to other soy isoflavones in healthy young Caucasian men.[Pubmed:22953831]

Food Chem. 2012 Dec 1;135(3):1104-11.

Glycitein is a Selective Estradiol Receptor Modulator (SERM) from soy. The study reports plasma bioavailability and urine excretion of Glycitein compared to other soy isoflavones after a unique intake of food supplement based on soy germ containing 55.24mg isoflavones. Eighteen plasma and urinary sampling profiles collected over 48h from healthy young Caucasian men were analysed using specific ELISAs. Eight profiles contained equol. Glycitein T(max), C(max), AUC(0-->24h) and T((1/2)) in plasma were calculated. Urine T(max), % of excretion at 24h and clearance were assessed. Glycitein is one of the best absorbed flavonoids. Plasma steady-state level can be achieved by several intakes a day. Glycitein bioavailability is similar to that of daidzein and its urinary excretion is significantly higher than that of genistein. Equol does not affect Glycitein bioavailability. Knowing Glycitein bioavailability in man is essential for the development of soy-germ-based food supplements for health applications.

Glycitein is a soybean (yellow cultivar) isoflavonoid; used in combination with other isoflavonoids such as genistein and daidzein to study apoptosis and anti-oxidation processes.

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