Glycitin

CAS# 40246-10-4

Glycitin

Catalog No. BCN5895----Order now to get a substantial discount!

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Quality Control of Glycitin

Number of papers citing our products

Chemical structure

Glycitin

3D structure

Chemical Properties of Glycitin

Cas No. 40246-10-4 SDF Download SDF
PubChem ID 187808 Appearance White powder
Formula C22H22O10 M.Wt 446.41
Type of Compound Flavonoids Storage Desiccate at -20°C
Synonyms Glycitein 7-O-β-glucoside
Solubility DMSO : ≥ 38 mg/mL (85.13 mM)
*"≥" means soluble, but saturation unknown.
Chemical Name 3-(4-hydroxyphenyl)-6-methoxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
SMILES COC1=C(C=C2C(=C1)C(=O)C(=CO2)C3=CC=C(C=C3)O)OC4C(C(C(C(O4)CO)O)O)O
Standard InChIKey OZBAVEKZGSOMOJ-MIUGBVLSSA-N
Standard InChI InChI=1S/C22H22O10/c1-29-15-6-12-14(30-9-13(18(12)25)10-2-4-11(24)5-3-10)7-16(15)31-22-21(28)20(27)19(26)17(8-23)32-22/h2-7,9,17,19-24,26-28H,8H2,1H3/t17-,19-,20+,21-,22-/m1/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Glycitin

The seed of Glycine max (L.) Merr.

Biological Activity of Glycitin

DescriptionGlycitin has antibacterial, antiviral, anti-obese,anti-diabetic and estrogenic activities and may exert preventative effects on alcoholism, osteonecrosis,cardiovascular and cerebrovascular diseases and some types of cancer. It has a protective effect on skin aging by inhibiting of MMP-1 and increasing of collagen through ERK/JNK/P38 down-regulation, shows good inhibitory effect on α-glucosidase with IC50 of 0.5646 mg/mL.
TargetsMMP(e.g.TIMP) | ERK | JNK | p38MAPK
In vitro

Effects of genistein, daidzein and glycitein on the osteogenic and adipogenic differentiation of bone marrow stromal cells and on the adipogenic trans-differentiation of osteoblasts[Reference: WebLink]

Acta Pharmacol. Sin., 2005, 26(9):1081-6.


METHODS AND RESULTS:
The 3-(4, 5-dimethylthiazol-2-yl)-2, 5-diphenyl tetrazolium bromide (MTT), alkaline phosphatase (ALP) activity and oil red O assays were used to examine the effects of genistein, diadzein and glycitein on the osteogenic and adipogenic differentiation of primary mouse bone marrow stromal cells (MSCs) and the adipogenic trans-differentiation of primary mouse osteoblasts. The results indicated that daidzein, genistein and glycitein at concentrations from 1 × 10−8mol/L to 1×10−5 mol/L promoted the proliferation of MSCs and osteoblasts; genistein, daidzein and glycitein promoted osteogenic differentiation and inhibited adipogenic differentiation of MSCs, and inhibited adipocytic transdifferentiation of osteoblasts at appropriate concentrations as 17β-estradiol.
CONCLUSIONS:
It suggests that genistein, daidzein and glycitein regulate a dual differentiational process of MSCs into the osteogenic and adipogenic lineages, and trans-differentiational process of primary osteoblasts into the adipocyte lineages, causing a lineage shift toward osteoblast. Protective effects of them on bone may be mediated by a reversal of adipogenesis which may promote the proliferation, differentiation and mineralization of osteoblasts, and make adipocytes secrete less cytokines which may promote osteoclast formation and activation. In addition, the results also indicated that genistein, daidzein and glycitein may be helpful in preventing the development of steroid induced osteonecrosis.

In vivo

Anti-obese and anti-diabetic effects of a mixture of daidzin and glycitin on C57BL/6J mice fed with a high-fat diet.[Pubmed: 25209298]

Biosci Biotechnol Biochem. 2015 Jan;79(1):117-23.


METHODS AND RESULTS:
We investigated the effects of a mixture of daidzin and Glycitin, which are the glycoside-form isoflavones of daidzein and glycitein, respectively, on body weight, lipid levels, diabetic markers, and metabolism in a high-fat diet (HF) fed C57BL/6J mice for 92 days. The mice were divided into basic diet group (CON), HF group, and HF companied with the isoflavone mixture group (HFISO). Results showed that mice in HFISO had a significantly lower body weight and adipose tissue compared to HF group. Blood glucose, serum HbA1c, and serum insulin also showed lower levels in HFISO group. In addition, higher hepatic GSH level and lower serum 8-hydroxy-2'-deoxyguanosine (8-OHdG) level were found in HFISO group mice.
CONCLUSIONS:
This suggests that the regulation of oxidative stress by daidzin and Glycitin was closely related to the suppression of adipose tissue and the progression of diabetes.

The Protective Effect of Glycitin on UV-induced Skin Photoaging in Human Primary Dermal Fibroblast[Reference: WebLink]

J. Korean Soc. App. Bi., 2014, 57(4):463-8.

Exposure of strong and repeated UV on the skin leads to skin aging, characterized with wrinkling, sagging, dyspigmentation, and laxity. Numerous studies revealed that Matrix metalloproteinases are related to skin aging and functions as degrading enzyme of various types of collagen.
METHODS AND RESULTS:
Here, we attempted to evaluate the effectiveness of Glycitin (4'-hydroxy-6-methoxy-isoflavone-7-D-glucoside) on skin aging and mechanisms of action in UV-irradiated human dermal fibroblasts. Especially we focused on the expression of Matrix metalloproteinase-1 (MMP-1), which degrades procollagen type-I in dermis, by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay, Western blot, and reverse transcription polymerase chain reaction in cell lysates or media. Our results showed that Glycitin increased the viability of human dermal fibroblast and alleviated MMP-1 expression caused by UV irradiation. In addition, synthesis of type-I collagen was increased and UV-induced phosphorylation of ERK/JNK/p38 was decreased in dose-dependent manners. Taken together, we demonstrated that treatment with glycitein have a protective effect on skin aging by inhibiting of MMP-1 and increasing of collagen through ERK/JNK/P38 down-regulation, which may be mediated by the inhibition of ERK, JNK, and p38 mitogen-activated protein kinases.
CONCLUSIONS:
We suggest that Glycitin is a potential agent for the treatment of skin ageing.

Protocol of Glycitin

Kinase Assay

Research on Structure Identification of Glycitin from Glycyrrhiza and Its Inhibitory Activity Against α-Glucosidase[Reference: WebLink]

Characterization of a β-glucosidase from Sulfolobus solfataricus for isoflavone glycosides.[Pubmed: 21898127]

Biotechnol Lett. 2012 Jan;34(1):125-9.

The specific activity of a recombinant β-glucosidase from Sulfolobus solfataricus for isoflavones was: daidzin > Glycitin > genistin > malonyl genistin > malonyl daidzin > malonyl Glycitin. The hydrolytic activity of this enzyme for daidzin was highest at pH 5.5 and 90°C with a half-life of 18 h, a K (m) of 0.5 mM, and a k (cat) of 2532 s(-1). The enzyme converted 1 mM daidzin to 1 mM daidzein after 1 h with a molar yield of 100% and a productivity of 1 mM h(-1). Among β-glucosidases, that from S. solfataricus β had the highest thermostability, k (cat), k (cat)/K (m), conversion yield, and productivity in the hydrolysis of daidzin.

Sci. Technol. Rev., 2014, 32(16):29-33.

An isoflavone Glycitin is isolated from the licorice, which has some inhibitory effect on α-glucosidase. The compound has been isolated from Glycyrrhiza for the first time. The inhibition activity against α-glucosidase is tested in vitro, and this compound shows good inhibition effect on α-glucosidase with IC50of 0.5646 mg·mL- 1, better than the position control acarbose. The results of kinetic experiments show that the depressant effect of Glycitin is non competitive inhibition and the constant of Kmis 8.1571 mol·L-1. The value of Kiis 1.318 mg·mL-1 calculated by the Dixon equation.

Cell Research

Glycitin regulates osteoblasts through TGF-β or AKT signaling pathways in bone marrow stem cells.[Pubmed: 27882117 ]

Exp Ther Med. 2016 Nov;12(5):3063-3067.

Cell lines:Bone marrow stem cells (BMSCs)
Concentrations: 0.01, 0.5, 1, 5 and 10 μM
Incubation Time:  7 days
Method:
BMSCs (1-2×106 cells or 1-2×104 per well) are cultured in 6- or 96-well culture plates overnight at 37°C in an atmosphere containing 5% CO2. Glycitin is added to the wells at final concentrations of 0.01, 0.5, 1, 5 and 10 μM and cultured for 7 days. In cells cultured in 6-well culture plates, BMSCs are determined using Oil Red O staining and observed via light microscopy at 510 nm. BMSCs are fixed using 5% precooled paraformaldehyde for 30 min at 4°C and stained with 0.6% (w/v) Oil Red O solution for 15 min at room temperature. Cells stained with Oil Red O are washed with water (3×5 min) to remove unbound dye, and culture dishes are stained with 1 ml isopropyl alcohol for 10 min. In cells cultured in 96-well culture plates, BMSCs are determined via MTT assay. A total of 20 μl MTT (5 g/l) are added to each well and cultured for 4 h. The supernatant is removed and 200 μl dimethylsulfoxide are added to each well for 15 min. Optical density (OD) is measured using a microplate spectrophotometer at 570 nm. Proliferation rate is calculated using: OD treated / OD control × 100%.

Animal Research

Comparative study on reduction of bone loss and lipid metabolism abnormality in ovariectomized rats by soy isoflavones, daidzin, genistin, and glycitin.[Pubmed: 11305597]

Biol Pharm Bull. 2001 Apr;24(4):368-72.

Animal Models: Female Sprague-Dawley rats
Formulation: suspended in water containing 1% hydroxypropyl cellulose
Dosages:25, 50 or 100 mg/kg/d
Administration: p.o.

Glycitin Dilution Calculator

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Glycitin Molarity Calculator

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Preparing Stock Solutions of Glycitin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.2401 mL 11.2005 mL 22.4009 mL 44.8019 mL 56.0023 mL
5 mM 0.448 mL 2.2401 mL 4.4802 mL 8.9604 mL 11.2005 mL
10 mM 0.224 mL 1.12 mL 2.2401 mL 4.4802 mL 5.6002 mL
50 mM 0.0448 mL 0.224 mL 0.448 mL 0.896 mL 1.12 mL
100 mM 0.0224 mL 0.112 mL 0.224 mL 0.448 mL 0.56 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Glycitin

Glycitin is a natural isoflavone isolated from legumes; promotes the proliferation of bone marrow stromal cells and osteoblasts and suppresses bone turnover.

References:
[1]. Uesugi T, et al. Comparative study on reduction of bone loss and lipid metabolism abnormality in ovariectomized rats by soy isoflavones, daidzin, genistin, and glycitin. Biol Pharm Bull. 2001 Apr;24(4):368-72. [2]. Li XH, et al. Effect of daidzin, genistin, and glycitin on osteogenic and adipogenic differentiation of bone marrow stromal cells and adipocytic transdifferentiation of osteoblasts. Acta Pharmacol Sin. 2005 Sep;26(9):1081-6.

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References on Glycitin

Characterization of a beta-glucosidase from Sulfolobus solfataricus for isoflavone glycosides.[Pubmed:21898127]

Biotechnol Lett. 2012 Jan;34(1):125-9.

The specific activity of a recombinant beta-glucosidase from Sulfolobus solfataricus for isoflavones was: daidzin > Glycitin > genistin > malonyl genistin > malonyl daidzin > malonyl Glycitin. The hydrolytic activity of this enzyme for daidzin was highest at pH 5.5 and 90 degrees C with a half-life of 18 h, a K (m) of 0.5 mM, and a k (cat) of 2532 s(-1). The enzyme converted 1 mM daidzin to 1 mM daidzein after 1 h with a molar yield of 100% and a productivity of 1 mM h(-1). Among beta-glucosidases, that from S. solfataricus beta had the highest thermostability, k (cat), k (cat)/K (m), conversion yield, and productivity in the hydrolysis of daidzin.

Anti-obese and anti-diabetic effects of a mixture of daidzin and glycitin on C57BL/6J mice fed with a high-fat diet.[Pubmed:25209298]

Biosci Biotechnol Biochem. 2015;79(1):117-23.

We investigated the effects of a mixture of daidzin and Glycitin, which are the glycoside-form isoflavones of daidzein and glycitein, respectively, on body weight, lipid levels, diabetic markers, and metabolism in a high-fat diet (HF) fed C57BL/6J mice for 92 days. The mice were divided into basic diet group (CON), HF group, and HF companied with the isoflavone mixture group (HFISO). Results showed that mice in HFISO had a significantly lower body weight and adipose tissue compared to HF group. Blood glucose, serum HbA1c, and serum insulin also showed lower levels in HFISO group. In addition, higher hepatic GSH level and lower serum 8-hydroxy-2'-deoxyguanosine (8-OHdG) level were found in HFISO group mice. This suggests that the regulation of oxidative stress by daidzin and Glycitin was closely related to the suppression of adipose tissue and the progression of diabetes.

Soy isoflavones and other isoflavonoids activate the human bitter taste receptors hTAS2R14 and hTAS2R39.[Pubmed:21942422]

J Agric Food Chem. 2011 Nov 9;59(21):11764-71.

The aim of this study was to identify the bitter receptor(s) that recognize the bitter taste of the soy isoflavone genistein. Screening of all 25 human bitter receptors revealed genistein as agonist of hTAS2R14 and hTAS2R39. Genistein displayed threshold values of 4 and 8 muM on hTAS2R14 and hTAS2R39 and EC(50) values of 29 and 49 muM, respectively. In addition, the behavior of structurally similar isoflavonoids was investigated. Although the two receptors are not closely related, the results for hTAS2R14 and hTAS2R39 were similar toward most isoflavonoid aglycones. By trend, threshold values were slightly lower on hTAS2R14. Glucosylation of isoflavones seemed to inhibit activation of hTAS2R14, whereas four of five glucosylated isoflavones were agonists of hTAS2R39, namely, Glycitin, genistin, acetylgenistin, and malonylgenistin. A total of three hydroxyl substitutions of the A- and B-rings of the isoflavonoids seemed to be more favorable for receptor activation than fewer hydroxyl groups. The concentration of the trihydroxylated genistein in several soy foods exceeds the determined bitter receptor threshold values, whereas those of other soy isoflavones are around or below their respective threshold value. Despite its low concentration, genistein might be one of the main contributors to the bitterness of soy products. Furthermore, the bioactive isoflavonoids equol and coumestrol activated both receptors, indicating that their sensory impact should be considered when used as food ingredients.

Description

Glycitin is a natural isoflavone isolated from legumes; promotes the proliferation of bone marrow stromal cells and osteoblasts and suppresses bone turnover.Glycitin is antibacterial, antiviral and estrogenic.

Keywords:

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