Glycitein | CAS#40957-83-3 | increases Nrf2-related antioxidative signaling

Glycitein
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 540183

CAS#: 40957-83-3

Description: Glycitein is found in soy and red clover. It exhibits a variety of biological activities, including increasing Nrf2-related antioxidative signaling, preventing invasion in glioma cells destabilizing amyloid-β aggregates and preventing fibril assembly, and inhibiting osteoclast generation.

Chemical Structure

Glycitein

CAS# 40957-83-3

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 540183
Name: Glycitein
CAS#: 40957-83-3
Chemical Formula: C16H12O5
Exact Mass: 284.07
Molecular Weight: 284.267
Elemental Analysis: C, 67.60; H, 4.26; O, 28.14

Price and Availability

Size	Price	Availability
10mg	USD 285	2 Weeks
25mg	USD 550	2 Weeks
50mg	USD 850	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: Glycitein; Q-100465; Q100465; Q 100465

IUPAC/Chemical Name: 7-hydroxy-3-(4-hydroxyphenyl)-6-methoxy-4H-chromen-4-one

InChi Key: DXYUAIFZCFRPTH-UHFFFAOYSA-N

InChi Code: InChI=1S/C16H12O5/c1-20-15-6-11-14(7-13(15)18)21-8-12(16(11)19)9-2-4-10(17)5-3-9/h2-8,17-18H,1H3

SMILES Code: O=C1C(C2=CC=C(O)C=C2)=COC3=CC(O)=C(OC)C=C13

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

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Product Data:

Product Data

Instruction:

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Biological target:	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.
In vitro activity:	The apoptotic SK-N-SH cell per-centage was 21% relative at 100 nM dosage of rotenone. Glycitein at 5 μM treatment reduced the rotenone-induced apoptosis to 13%. At 10 μM dosage of the glycitein, the apoptosis decreased to 5.7% (Fig. 6A). The western blot analysis showed that glycitein treatment caused a decrease in a rotenone triggered upregulation of Bax and caspase-3 expression (Fig. 6B). Reference: Acta Biochim Pol. 2022 Jun 12;69(2):447-452. https://pubmed.ncbi.nlm.nih.gov/35691030/
In vivo activity:	Figure 2A demonstrates that the levels of ROS in the C. elegans CL2006 fed with glycitein for 36 h were reduced (control 100 ± 23%, glycitein 68.9 ± 7 %, n = 3, p = 0.05). These results suggest the decreased Aβ toxicity by glycitein might be, in part, a consequence of its antioxidative action. Reference: BMC Neurosci. 2005 Aug 25;6:54. https://pubmed.ncbi.nlm.nih.gov/16122394/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	27.2	95.57
	DMF	0.5	1.76

Preparing Stock Solutions

The following data is based on the product molecular weight 284.27 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:	1. Dong N, Yang Z. Glycitein exerts neuroprotective effects in Rotenone-triggered oxidative stress and apoptotic cell death in the cellular model of Parkinson's disease. Acta Biochim Pol. 2022 Jun 12;69(2):447-452. doi: 10.18388/abp.2020_5963. PMID: 35691030. 2. Zhang B, Su JP, Bai Y, Li J, Liu YH. Inhibitory effects of O-methylated isoflavone glycitein on human breast cancer SKBR-3 cells. Int J Clin Exp Pathol. 2015 Jul 1;8(7):7809-17. PMID: 26339345; PMCID: PMC4555673. 3. Gutierrez-Zepeda A, Santell R, Wu Z, Brown M, Wu Y, Khan I, Link CD, Zhao B, Luo Y. Soy isoflavone glycitein protects against beta amyloid-induced toxicity and oxidative stress in transgenic Caenorhabditis elegans. BMC Neurosci. 2005 Aug 25;6:54. doi: 10.1186/1471-2202-6-54. PMID: 16122394; PMCID: PMC1215487. 4. Pan W, Ikeda K, Takebe M, Yamori Y. 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. doi: 10.1093/jn/131.4.1154. PMID: 11285318.
In vitro protocol:	1. Dong N, Yang Z. Glycitein exerts neuroprotective effects in Rotenone-triggered oxidative stress and apoptotic cell death in the cellular model of Parkinson's disease. Acta Biochim Pol. 2022 Jun 12;69(2):447-452. doi: 10.18388/abp.2020_5963. PMID: 35691030. 2. Zhang B, Su JP, Bai Y, Li J, Liu YH. Inhibitory effects of O-methylated isoflavone glycitein on human breast cancer SKBR-3 cells. Int J Clin Exp Pathol. 2015 Jul 1;8(7):7809-17. PMID: 26339345; PMCID: PMC4555673.
In vivo protocol:	1. Gutierrez-Zepeda A, Santell R, Wu Z, Brown M, Wu Y, Khan I, Link CD, Zhao B, Luo Y. Soy isoflavone glycitein protects against beta amyloid-induced toxicity and oxidative stress in transgenic Caenorhabditis elegans. BMC Neurosci. 2005 Aug 25;6:54. doi: 10.1186/1471-2202-6-54. PMID: 16122394; PMCID: PMC1215487. 2. Pan W, Ikeda K, Takebe M, Yamori Y. 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. doi: 10.1093/jn/131.4.1154. PMID: 11285318.

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1: Zhang B, Su JP, Bai Y, Li J, Liu YH. Inhibitory effects of O-methylated isoflavone glycitein on human breast cancer SKBR-3 cells. Int J Clin Exp Pathol. 2015 Jul 1;8(7):7809-17. eCollection 2015. PubMed PMID: 26339345; PubMed Central PMCID: PMC4555673.

2: Hu YJ, Gao KG, Zheng CT, Wu ZJ, Yang XF, Wang L, Ma XY, Zhou AG, Jiang ZJ. Effect of dietary supplementation with glycitein during late pregnancy and lactation on antioxidative indices and performance of primiparous sows. J Anim Sci. 2015 May;93(5):2246-54. doi: 10.2527/jas.2014-7767. Erratum in: J Anim Sci. 2015 Jun;93(6):3226. PubMed PMID: 26020321.

3: Artigot MP, Baes M, Daydé J, Berger M. Expression of flavonoid 6-hydroxylase candidate genes in normal and mutant soybean genotypes for glycitein content. Mol Biol Rep. 2013 Jul;40(7):4361-9. doi: 10.1007/s11033-013-2526-2. Epub 2013 May 22. PubMed PMID: 23695494.

4: Shinkaruk S, Durand M, Lamothe V, Carpaye A, Martinet A, Chantre P, Vergne S, Nogues X, Moore N, Bennetau-Pelissero C. Bioavailability of glycitein relatively to other soy isoflavones in healthy young Caucasian men. Food Chem. 2012 Dec 1;135(3):1104-11. doi: 10.1016/j.foodchem.2012.03.135. Epub 2012 May 22. PubMed PMID: 22953831.

5: Roh C. Microbial transformation of bioactive compounds and production of ortho-dihydroxyisoflavones and glycitein from natural fermented soybean paste. Biomolecules. 2014 Dec 12;4(4):1093-101. doi: 10.3390/biom4041093. PubMed PMID: 25513748; PubMed Central PMCID: PMC4279171.

6: Winzer M, Rauner M, Pietschmann P. Glycitein decreases the generation of murine osteoclasts and increases apoptosis. Wien Med Wochenschr. 2010 Sep;160(17-18):446-51. doi: 10.1007/s10354-010-0811-4. Epub 2010 Aug 16. PubMed PMID: 20714813.

7: Shimoda K, Hamada H. Synthesis of beta-maltooligosaccharides of glycitein and daidzein and their anti-oxidant and anti-allergic activities. Molecules. 2010 Jul 29;15(8):5153-61. doi: 10.3390/molecules15085153. PubMed PMID: 20714292.

8: Lee EJ, Kim SY, Hyun JW, Min SW, Kim DH, Kim HS. Glycitein inhibits glioma cell invasion through down-regulation of MMP-3 and MMP-9 gene expression. Chem Biol Interact. 2010 Apr 15;185(1):18-24. doi: 10.1016/j.cbi.2010.02.037. Epub 2010 Feb 25. PubMed PMID: 20188714.

9: Kang KA, Zhang R, Piao MJ, Lee KH, Kim BJ, Kim SY, Kim HS, Kim DH, You HJ, Hyun JW. Inhibitory effects of glycitein on hydrogen peroxide induced cell damage by scavenging reactive oxygen species and inhibiting c-Jun N-terminal kinase. Free Radic Res. 2007 Jun;41(6):720-9. PubMed PMID: 17516245.

10: Gutierrez-Zepeda A, Santell R, Wu Z, Brown M, Wu Y, Khan I, Link CD, Zhao B, Luo Y. Soy isoflavone glycitein protects against beta amyloid-induced toxicity and oxidative stress in transgenic Caenorhabditis elegans. BMC Neurosci. 2005 Aug 25;6:54. PubMed PMID: 16122394; PubMed Central PMCID: PMC1215487.

11: Kim JH, Park DK, Lee CH, Yoon DY. A new isoflavone glycitein 7-O-beta-D-glucoside 4''-O-methylate, isolated from Cordyceps militaris grown on germinated soybeans extract, inhibits EGF-induced mucus hypersecretion in the human lung mucoepidermoid cells. Phytother Res. 2012 Dec;26(12):1807-12. doi: 10.1002/ptr.4655. Epub 2012 Mar 9. PubMed PMID: 22407817.

12: Simons AL, Renouf M, Hendrich S, Murphy PA. Metabolism of glycitein (7,4'-dihydroxy-6-methoxy-isoflavone) by human gut microflora. J Agric Food Chem. 2005 Nov 2;53(22):8519-25. PubMed PMID: 16248547.

13: Shinkaruk S, Lamothe V, Schmitter JM, Fructus A, Sauvant P, Vergne S, Degueil M, Babin P, Bennetau B, Bennetau-Pelissero C. Synthesis of haptens and conjugates for ELISA of glycitein: development and validation of an immunological test. J Agric Food Chem. 2008 Aug 27;56(16):6809-17. doi: 10.1021/jf800663s. Epub 2008 Jul 23. PubMed PMID: 18646854.

14: Clubbs EA, Bomser JA. Basal cell induced differentiation of noncancerous prostate epithelial cells (RWPE-1) by glycitein. Nutr Cancer. 2009;61(3):390-6. doi: 10.1080/01635580802582728. PubMed PMID: 19373613.

15: Song TT, Hendrich S, Murphy PA. Estrogenic activity of glycitein, a soy isoflavone. J Agric Food Chem. 1999 Apr;47(4):1607-10. Erratum in: J Agric Food Chem 2002 Apr 10;50(8):2470. PubMed PMID: 10564025.

16: Lee SO, Renouf M, Ye Z, Murphy PA, Hendrich S. Isoflavone glycitein diminished plasma cholesterol in female golden Syrian hamsters. J Agric Food Chem. 2007 Dec 26;55(26):11063-7. Epub 2007 Nov 27. PubMed PMID: 18038972.

17: Boltovets P, Shinkaruk S, Bennetau-Pelissero C, Bennetau B, Snopok B. The effect of low pH on the glycitein-BSA conjugate interaction with specific antiserum: competitive inhibition study using surface plasmon resonance technique. Talanta. 2011 May 15;84(3):867-73. doi: 10.1016/j.talanta.2011.02.008. Epub 2011 Feb 19. PubMed PMID: 21482295.

18: Hur H, Rafii F. Biotransformation of the isoflavonoids biochanin A, formononetin, and glycitein by Eubacterium limosum. FEMS Microbiol Lett. 2000 Nov 1;192(1):21-5. PubMed PMID: 11040423.

19: Zhang Y, Wang GJ, Song TT, Murphy PA, Hendrich S. Urinary disposition of the soybean isoflavones daidzein, genistein and glycitein differs among humans with moderate fecal isoflavone degradation activity. J Nutr. 1999 May;129(5):957-62. Erratum in: J Nutr 2001 Jan;131(1):147-8. PubMed PMID: 10222386.

20: Klus K, Barz W. Formation of polyhydroxylated isoflavones from the soybean seed isoflavones daidzein and glycitein by bacteria isolated from tempe. Arch Microbiol. 1995 Dec;164(6):428-34. PubMed PMID: 8588745.

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