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Tricin

Chemical compound From Wikipedia, the free encyclopedia

Tricin
Not to be confused with Tricine.

Tricin is a chemical compound. It is an O-methylated flavone, a type of flavonoid. It can be found in rice bran[1] and sugarcane.[2]

Quick Facts Names, Identifiers ...
Tricin
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Names
IUPAC name
4′,5,7-Trihydroxy-3′,5′-dimethoxyflavone
Systematic IUPAC name
5,7-Dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-4H-1-benzopyran-4-one
Other names
Tricetin 3′,5′-dimethyl ether
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
KEGG
UNII
  • InChI=1S/C17H14O7/c1-22-14-3-8(4-15(23-2)17(14)21)12-7-11(20)16-10(19)5-9(18)6-13(16)24-12/h3-7,18-19,21H,1-2H3 N
    Key: HRGUSFBJBOKSML-UHFFFAOYSA-N N
  • COC1=CC(=CC(=C1O)OC)C2=CC(=O)C3=C(C=C(C=C3O2)O)O
Properties
C17H14O7
Molar mass 330.29 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Glycosides

  • Tricin 4'-glucoside (Tricin-4'-O-beta-D-glucopyranaoside, CAS number 71855-50-0)
  • Tricin 5-glucoside (Tricin 5-O-beta-D-glucopyranoside, CAS number 32769-00-9)
  • Tricin 7-O-glucoside (Tricin 7-O-beta-D-glucopyranoside, CAS number 32769-01-0)

Biosynthesis

The biosynthesis of flavones has not yet been elucidated in full; however, most of the mechanistic and enzymatic steps have been discovered and studied. In biosynthesizing tricin, there is first stepwise addition of malonyl-CoA via the polyketide pathway and p-coumaroyl-CoA via the phenylpropanoid pathway.[3] These additions are mediated by the sequential action of chalcone synthase and chalcone isomerase to yield naringenin chalcone and the flavanone, naringenin, respectively. CYP93G1 of the CYP450 superfamily in rice then desaturates naringenin into apigenin. After this step, it is proposed that flavonoid 3',5'-hydroxylase (F3',5'H) changes apigenin into tricetin.[4] Upon formation of tricetin, 3'-O-methyltransferase and 5'-O-methyltransferase add methoxy groups to tricetin to form tricin.

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p-Coumaroyl-CoA and malonyl-Coa units are synthesized together to form naringenin. The biosynthetic pathway then follows to form tricin.

Other compounds formed from tricin

Three flavonolignans derived from tricin have been isolated from oats Avena sativa.[5]

References

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