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Glycitein

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Not to be confused with glycitin.
Glycitein
Glycitein molecule
Names
IUPAC name
4′,7-Dihydroxy-6-methoxyisoflavone
Systematic IUPAC name
7-Hydroxy-3-(4-hydroxyphenyl)-6-methoxy-4H-1-benzopyran-4-one
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
KEGG
UNII
  • 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 ☒N
    Key: DXYUAIFZCFRPTH-UHFFFAOYSA-N ☒N
  • InChI=1/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
    Key: DXYUAIFZCFRPTH-UHFFFAOYAM
  • COC1=C(C=C2C(=C1)C(=O)C(=CO2)C3=CC=C(C=C3)O)O
Properties
C16H12O5
Molar mass 284.267 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Glycitein is an O-methylated isoflavone which accounts for 5-10% of the total isoflavones in soy food products. Glycitein is a phytoestrogen with weak estrogenic activity, comparable to that of the other soy isoflavones.[1] Like other isoflavonoids, glycitein is synthesized as a glycoside conjugate to a monosaccharide (typically glucose). The glycoside is hydrolyzed during digestion to the biologically-active free isoflavonoid.[2]

Glycitein is synthesized from phenylalanine, similarly to other isoflavonoids. The biosynthesis involves 8 steps, resulting in free glycitein; a subsequent glucosyltransferase-catalyzed reaction results in the corresponding glucoside, glycitin. This product may be further malonylated to malonylglycitin.[3]

Glycitein has been investigated for its benefits to human health. It binds to the human estrogen receptor (as do other isoflavonoids), and while it does so with lower affinity than other isoflavonoids, it is thought to be overall more potent as an estrogen receptor agonist due to its high bioavailability and its breakdown into further estrogenic products. The estrogenic activity of glycitein is thought to underlie its suppression of oxidative stress and its promotion of decreased blood pressure, though other mechanisms are likely also involved.[4]

References

[edit]
  1. ^ Song TT, Hendrich S, Murphy PA (1999). "Estrogenic activity of glycitein, a soy isoflavone". J. Agric. Food Chem. 47 (4): 1607–1610. Bibcode:1999JAFC...47.1607S. doi:10.1021/jf981054j. PMID 10564025. S2CID 22293253.
  2. ^ Heinonen SM, Hoikkala A, Wähälä A, Aldercreutz H (2003). "Metabolism of the soy isoflavones daidzein, genistein and glycitein in human subjects: Identification of new metabolites having an intact isoflavonoid skeleton". J. Steroid Biochem. Mol. Biol. 87 (4–5): 285–299. doi:10.1016/j.jsbmb.2003.09.003.
  3. ^ Dhaubhadel S, McGarvey BD, Williams R, Gijzen M (2003). "Isoflavonoid biosynthesis and accumulation in developing soybean seeds". Plant Mol. Biol. 53: 733–743. doi:10.1023/B:PLAN.0000023666.30358.ae.
  4. ^ Stephens, Brian R.; Bomser, Joshua A. (2013). "Chapter 28: Glycitein in Health". In Preedy, Victor R. (ed.). Isoflavones: Chemistry, Analysis, Function, and Effects. The Royal Society of Chemistry. pp. 465–474. ISBN 978-1-84973-419-6.


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