Glycitin

Glycitin

Names
IUPAC name 7-(β-D-Glucopyranosyloxy)-4′-hydroxy-6-methoxyisoflavone
Systematic IUPAC name 3-(4-Hydroxyphenyl)-6-methoxy-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-1-benzopyran-4-one
Other names Glycitein 7-O-glucoside
Identifiers
CAS Number	40246-10-4
3D model (JSmol)	Interactive image
ChEBI	CHEBI:80373
KEGG	C16195
PubChem CID	187808
UNII	G2S44P62XC
CompTox Dashboard (EPA)	DTXSID80193227
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 Key: OZBAVEKZGSOMOJ-MIUGBVLSSA-N
SMILES COC1=C(C=C2C(=C1)C(=O)C(=CO2)C3=CC=C(C=C3)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O
Properties
Chemical formula	C22H22O10
Molar mass	446.408 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Glycitin (glycitein 7-O-glucoside) is an isoflavone found in soy, and remains to various degrees in soy products like tofu, soymilk^[1] and soy sauce.^[2] Although glycitin has its own health associated properties (below), it can be transformed to glycitein by human intestinal flora by the action of beta-glucosidases.^[3]

Properties

Some interesting effects of glycitin include human dermal fibroblast cell proliferation and migration via TGF‐β signaling, glycitin treatment produces anti-photoaging effects such as collagen type I and collagen type III increase at both the mRNA and protein levels. Other noted effects decreased elastase, and decreased β‐galactosidase activation.^[4] In conjunction with 4′,6,7-trimethoxyisoflavone (TMF), an isoflavone that promotes fibroblast migration but not proliferation, wound healing and anti-scarring activity (reorganization and wound fibrosis inhibition) were significantly and synergistically boosted in both in vivo mice and in vitro.^[5]

References

This page was last edited on 3 July 2023, at 07:20