Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C22H22O10 |
Molecular Weight | 446.4041 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 5 / 5 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=CC2=C(OC=C(C2=O)C3=CC=C(O)C=C3)C=C1O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O
InChI
InChIKey=OZBAVEKZGSOMOJ-MIUGBVLSSA-N
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
Glycitin (4'-Hydroxy-6-Methoxyisoflavone-7-D-Glucoside) is a soy isoflavone. Isoflavone mixtures from soybean containing glycitin exert anti-obese and antidiabetic, antineoplastic, antioxidant effects. Isoflavone supplementation in healthy males may enhance cognitive processes which appear dependent on oestrogen activation. Glycitin underwent hydrolysis of the beta-glycoside moiety and little further biotransformation, leading to high plasma glycitein concentrations.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19480732
Curator's Comment: Soya isoflavone supplementation containing Glycitin enhances spatial working memory in men.
Volunteers were randomised to take four capsules/d containing soya isoflavones (116 mg isoflavone equivalents/d: 68 mg daidzein, 12 mg genistein, 36 mg glycitin) or placebo for 6 weeks, and the alternate treatment during the following 6 weeks. Assessments of memory (verbal episodic, auditory and working), executive function (planning, attention, mental flexibility) and visual-spatial processing were performed at baseline and after each treatment period. Isoflavone supplementation significantly improved spatial working memory (P = 0.01), a test in which females consistently perform better than males. Compared with placebo supplementation, there were 18 % fewer attempts (P = 0.01), 23 % fewer errors (P = 0.02) and 17 % less time (P = 0.03) required to correctly identify the requisite information.
Originator
Sources: Kudou, S., Fleury, Y., Welti, D.. Magnoiato, D., Uchida, T., Kitamura, K., Okubo, K. Malonyl isoflavones glycosides in soybean seeds (Glycine max Merrill). Agric. Biol. Chem. 1991,55,2227-2233.
Curator's Comment: Kudou et al. (1991) isolated and characterized nine beta-glucoside forms of isoflavones from soybean hypocotyl. They are daidzin, glycitin, genistin, 6'-0-acetyl daidzin, 6'-0-acetyl glycitin, 6'-0-acetyl genistin, 6'-0-malonyl daidzin, 6'-0-malonyl glycitin and 6'-0-malonyl genistin. reference retrieved from http://lib.dr.iastate.edu/cgi/viewcontent.cgi?article=13527&context=rtd
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: GO:0008283 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25758427 |
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Target ID: GO:0006915 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20404023 |
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Target ID: WP408 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Bioavailability of pure isoflavones in healthy humans and analysis of commercial soy isoflavone supplements. | 2001 Apr |
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Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods. | 2006 Nov |
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Flavonoids possess neuroprotective effects on cultured pheochromocytoma PC12 cells: a comparison of different flavonoids in activating estrogenic effect and in preventing beta-amyloid-induced cell death. | 2007 Mar 21 |
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Soya isoflavone supplementation enhances spatial working memory in men. | 2009 Nov |
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Soy Isoflavone Glycitin (4'-Hydroxy-6-Methoxyisoflavone-7-D-Glucoside) Promotes Human Dermal Fibroblast Cell Proliferation and Migration via TGF-β Signaling. | 2015 May |
Patents
Sample Use Guides
Volunteers were randomised to take four capsules/d containing soya isoflavones (116 mg isoflavone equivalents/d: 68 mg daidzein, 12 mg genistein, 36 mg glycitin) or placebo for 6 weeks, and the alternate treatment during the following 6 weeks. Assessments of memory (verbal episodic, auditory and working), executive function (planning, attention, mental flexibility) and visual-spatial processing were performed at baseline and after each treatment period.
Glycitin (25 mg), the β-glycoside of glycitein, was administered orally as a single-bolus dose, and blood samples were collected.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25758427
Treatment of primary dermal fibroblasts with glycitin increased cell proliferation and migration. In addition, treatment with 20 μM glycitin for 24 h induced the synthesis of collagen type I and type III at both the mRNA and protein levels. Fibronectin was also increased by 20% after treatment. Matrix metalloproteinase-1 collagenase was decreased in the media after 24-h incubation with glycitin, and the synthesis of transforming growth factor-beta (TGF-β) mRNA increased approximately twofold in cells following glycitin treatment. Phosphorylation of Smad2 and Smad3 increased after 1 h of glycitin treatment, and phosphorylation continued for 24 h. Furthermore, the phosphorylated form of AKT was increased in glycitin-treated cells after 3 h and remained higher for 24 h.
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DSLD |
1428 (Number of products:4)
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DTXSID80193227
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187808
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G2S44P62XC
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Glycitin
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40246-10-4
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1295855
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80373
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SUBSTANCE RECORD