Glycitin

Last updated
Glycitin
Glycitin.svg
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
3D model (JSmol)
ChEBI
ChemSpider
KEGG
PubChem CID
UNII
  • 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
  • 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
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).

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

  1. ↑ Hsiao, Yu-Hsuan; Yu, Chia-Jung; Li, Wen-Tai; Hsieh, Jung-Feng (2015). "Coagulation of β-conglycinin, glycinin and isoflavones induced by calcium chloride in soymilk". Scientific Reports. 5 13018. Bibcode:2015NatSR...513018H. doi:10.1038/srep13018. PMC   4542527 . PMID   26260443.
  2. ↑ "Health Benefits of Naturally Brewed Soy Sauce". 2018-04-04.
  3. ↑ "Human Metabolome Database: Showing metabocard for Glycitin (HMDB0002219)".
  4. ↑ Kim, Young Mee; Huh, Jung Sik; Lim, Yoongho; Cho, Moonjae (2015). "Soy Isoflavone Glycitin (4'-Hydroxy-6-Methoxyisoflavone-7-D-Glucoside) Promotes Human Dermal Fibroblast Cell Proliferation and Migration via TGF-β Signaling". Phytotherapy Research. 29 (5): 757–769. doi:10.1002/ptr.5313. PMID   25758427. S2CID   206430410.
  5. ↑ Kim, Joungmok; Yang, Goowon; Kim, Yeji; Kim, Jin; Ha, Joohun (2016). "AMPK activators: Mechanisms of action and physiological activities". Experimental & Molecular Medicine. 48 (4): e224. doi:10.1038/emm.2016.16. PMC   4855276 . PMID   27034026.
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