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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
Structure of GLYCITIN

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

HIDE SMILES / InChI
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

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

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Bioavailability of pure isoflavones in healthy humans and analysis of commercial soy isoflavone supplements.
2001 Apr
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.
2006 Nov
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
Soya isoflavone supplementation enhances spatial working memory in men.
2009 Nov
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

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
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.
Name Type Language
GLYCITIN
USP-RS  
Common Name English
3-(4-HYDROXYPHENYL)-6-METHOXY-4-OXO-4H-CHROMEN-7-YL .BETA.-D-GLUCOPYRANOSIDE
Systematic Name English
4H-1-BENZOPYRAN-4-ONE, 7-(.BETA.-D-GLUCOPYRANOSYLOXY)-3-(4-HYDROXYPHENYL)-6-METHOXY-
Common Name English
GLYCITEIN-7-.BETA.-O-GLUCOSIDE
Common Name English
GLYCITEIN 7-O-GLUCOSIDE
Common Name English
GLYCITIN [USP-RS]
Common Name English
GLYCITEIN 7-O-.BETA.-GLUCOSIDE
Common Name English
GLYCITIN (CONSTITUENT OF SOY ISOFLAVONES) [DSC]
Common Name English
Classification Tree Code System Code
DSLD 1428 (Number of products:4)
Created by admin on Sat Dec 16 09:54:35 GMT 2023 , Edited by admin on Sat Dec 16 09:54:35 GMT 2023
Code System Code Type Description
EPA CompTox
DTXSID80193227
Created by admin on Sat Dec 16 09:54:35 GMT 2023 , Edited by admin on Sat Dec 16 09:54:35 GMT 2023
PRIMARY
PUBCHEM
187808
Created by admin on Sat Dec 16 09:54:35 GMT 2023 , Edited by admin on Sat Dec 16 09:54:35 GMT 2023
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FDA UNII
G2S44P62XC
Created by admin on Sat Dec 16 09:54:35 GMT 2023 , Edited by admin on Sat Dec 16 09:54:35 GMT 2023
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WIKIPEDIA
Glycitin
Created by admin on Sat Dec 16 09:54:35 GMT 2023 , Edited by admin on Sat Dec 16 09:54:35 GMT 2023
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CAS
40246-10-4
Created by admin on Sat Dec 16 09:54:35 GMT 2023 , Edited by admin on Sat Dec 16 09:54:35 GMT 2023
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RS_ITEM_NUM
1295855
Created by admin on Sat Dec 16 09:54:35 GMT 2023 , Edited by admin on Sat Dec 16 09:54:35 GMT 2023
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CHEBI
80373
Created by admin on Sat Dec 16 09:54:35 GMT 2023 , Edited by admin on Sat Dec 16 09:54:35 GMT 2023
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