| 词条 | Tricin |
| 释义 |
| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 401019352 | ImageFile = Tricin.svg | ImageSize = 250px | ImageAlt = Skeletal formula | ImageFile1 = Tricin molecule ball.png | ImageSize1 = 220 | ImageAlt1 = Ball-and-stick model | IUPACName = 5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-4H-chromen-4-one | OtherNames = Tricetin 3',5'-dimethyl ether 5,7-Dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)chromen-4-one |Section1={{Chembox Identifiers | CASNo_Ref = {{cascite|correct|??}} | CASNo = 520-32-1 | PubChem = 5281702 | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID = 4445019 | ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL = 454320 | ChEBI_Ref = {{ebicite|changed|EBI}} | ChEBI = 59979 | KEGG_Ref = {{keggcite|changed|kegg}} | KEGG = C10193 | StdInChI_Ref = {{stdinchicite|changed|chemspider}} | StdInChI = 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 | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | StdInChIKey = HRGUSFBJBOKSML-UHFFFAOYSA-N | SMILES = COC1=CC(=CC(=C1O)OC)C2=CC(=O)C3=C(C=C(C=C3O2)O)O |Section2={{Chembox Properties | Formula = C17H14O7 | MolarMass= 330.29 g/mol | Appearance = | Density = | MeltingPt = | BoilingPt = | Solubility = |Section3={{Chembox Hazards | MainHazards= | FlashPt= | AutoignitionPt = }}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] Glycosides
BiosynthesisThe 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 adds methoxy groups to tricetin to form tricin. Other compounds formed from tricinThree flavonolignans derived from tricin have been isolated from oats Avena sativa.[5] References1. ^The rice bran constituent tricin potently inhibits cyclooxygenase enzymes and interferes with intestinal carcinogenesis in ApcMin mice {{flavone}}2. ^{{cite journal | pmid = 27598841 | doi=10.1590/0001-3765201620150349 | volume=88 | title=Phenolic compounds and anticancer activity of commercial sugarcane cultivated in Brazil | journal=An. Acad. Bras. Ciênc. | pages=1201–9 | last1 = Alves | first1 = VG | last2 = Souza | first2 = AG | last3 = Chiavelli | first3 = LU | last4 = Ruiz | first4 = AL | last5 = Carvalho | first5 = JE | last6 = Pomini | first6 = AM | last7 = Silva | first7 = CC | year=2016}} 3. ^{{cite journal | doi = 10.1007/s11101-009-9161-5 | volume=9 | title=Tricin—a potential multifunctional nutraceutical | year=2009 | journal=Phytochemistry Reviews | pages=413–424 | last1 = Zhou | first1 = Jian-Min | last2 = Ibrahim | first2 = Ragai K.}} 4. ^{{cite journal | pmid = 24843076 | doi=10.1104/pp.114.239723 | volume=165 | title=Cytochrome P450 93G1 Is a Flavone Synthase II That Channels Flavanones to the Biosynthesis of Tricin O-Linked Conjugates in Rice | pmc=4081339 | journal=Plant Physiol | pages=1315–1327 | last1 = Lam | first1 = PY | last2 = Zhu | first2 = FY | last3 = Chan | first3 = WL | last4 = Liu | first4 = H | last5 = Lo | first5 = C | year=2014}} 5. ^{{cite journal|doi=10.1021/np049636k | volume=68 | title=Flavonolignans from Avena sativa | year=2005 | journal=Journal of Natural Products | pages=289–292 | last1 = Wenzig | first1 = Eva}} 2 : O-Methylated flavones|Resorcinols |
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