Tricin
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
Identifiers
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
C17 H14 O7
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).
Chemical compound
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]
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) 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.
p -Coumaroyl-CoA and malonyl-Coa units are synthesized together to form naringenin. The biosynthetic pathway then follows to form tricin.Three flavonolignans derived from tricin have been isolated from oats Avena sativa .[ 5]
^ The rice bran constituent tricin potently inhibits cyclooxygenase enzymes and interferes with intestinal carcinogenesis in ApcMin mice
^ Alves, VG; Souza, AG; Chiavelli, LU; Ruiz, AL; Carvalho, JE; Pomini, AM; Silva, CC (2016). "Phenolic compounds and anticancer activity of commercial sugarcane cultivated in Brazil" . An. Acad. Bras. Ciênc . 88 (3): 1201–9. doi :10.1590/0001-3765201620150349 . PMID 27598841 .
^ Zhou, Jian-Min; Ibrahim, Ragai K. (2009). "Tricin—a potential multifunctional nutraceutical". Phytochemistry Reviews . 9 (3): 413–424. doi :10.1007/s11101-009-9161-5 . S2CID 27161417 .
^ Lam, PY; Zhu, FY; Chan, WL; Liu, H; Lo, C (2014). "Cytochrome P450 93G1 Is a Flavone Synthase II That Channels Flavanones to the Biosynthesis of Tricin O-Linked Conjugates in Rice" . Plant Physiol . 165 (3): 1315–1327. doi :10.1104/pp.114.239723 . PMC 4081339 . PMID 24843076 .
^ Wenzig, Eva (2005). "Flavonolignans from Avena sativa". Journal of Natural Products . 68 (2): 289–292. doi :10.1021/np049636k . PMID 15730266 .
Aglycones
Monohydroxyflavone Dihydroxyflavones Trihydroxyflavones Tetrahydroxyflavones Pentahydroxyflavones O-methylated flavones
Glycosides
of apigenin of baicalein of hypolaetin
Hypolaetin 8-glucoside
Hypolaetin 8-glucuronide
of luteolin
Acetylated
Artocarpetin A
Artoindonesianin P
Sulfated glycosides Polymers Drugs