Tricin

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Tricin
Tricin.svg
Tricin molecule ball.png
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
PubChem CID
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 X mark.svgN
    Key: HRGUSFBJBOKSML-UHFFFAOYSA-N X mark.svgN
  • 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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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]

Contents

Glycosides

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.

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

Related Research Articles

Isoflavones are substituted derivatives of isoflavone, a type of naturally occurring isoflavonoids, many of which act as phytoestrogens in mammals. Isoflavones occur in many plant species, but are especially high in soybeans.

<span class="mw-page-title-main">Naringenin</span> Chemical compound

Naringenin is a flavanone from the flavonoid group of polyphenols. It is commonly found in citrus fruits, especially as the predominant flavonone in grapefruit.

<span class="mw-page-title-main">Rutin</span> Chemical compound

Rutin is the glycoside combining the flavonol quercetin and the disaccharide rutinose. It is a flavonoid glycoside found in a wide variety of plants, including citrus.

<span class="mw-page-title-main">Cyanidin</span> Anthocyanidin pigment in flowering plant petals and fruits

Cyanidin is a natural organic compound. It is a particular type of anthocyanidin. It is a pigment found in many red berries including grapes, bilberry, blackberry, blueberry, cherry, chokeberry, cranberry, elderberry, hawthorn, loganberry, açai berry and raspberry. It can also be found in other fruits such as apples and plums, and in red cabbage and red onion. It has a characteristic reddish-purple color, though this can change with pH; solutions of the compound are red at pH < 3, violet at pH 7-8, and blue at pH > 11. In certain fruits, the highest concentrations of cyanidin are found in the seeds and skin. Cyanidin has been found to be a potent sirtuin 6 (SIRT6) activator.

<span class="mw-page-title-main">Hesperidin</span> Chemical compound

Hesperidin is a flavanone glycoside found in citrus fruits. Its aglycone is hesperetin. Its name is derived from the word "hesperidium", for fruit produced by citrus trees.

<span class="mw-page-title-main">Apigenin</span> Chemical compound

Apigenin (4′,5,7-trihydroxyflavone), found in many plants, is a natural product belonging to the flavone class that is the aglycone of several naturally occurring glycosides. It is a yellow crystalline solid that has been used to dye wool.

<span class="mw-page-title-main">Kaempferol</span> Chemical compound

Kaempferol (3,4′,5,7-tetrahydroxyflavone) is a natural flavonol, a type of flavonoid, found in a variety of plants and plant-derived foods including kale, beans, tea, spinach, and broccoli. Kaempferol is a yellow crystalline solid with a melting point of 276–278 °C (529–532 °F). It is slightly soluble in water and highly soluble in hot ethanol, ethers, and DMSO. Kaempferol is named for 17th-century German naturalist Engelbert Kaempfer.

<span class="mw-page-title-main">Flavones</span> Class of flavonoid chemical compounds

Flavones are a class of flavonoids based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one).

<span class="mw-page-title-main">Chalcone synthase</span>

Chalcone synthase or naringenin-chalcone synthase (CHS) is an enzyme ubiquitous to higher plants and belongs to a family of polyketide synthase enzymes (PKS) known as type III PKS. Type III PKSs are associated with the production of chalcones, a class of organic compounds found mainly in plants as natural defense mechanisms and as synthetic intermediates. CHS was the first type III PKS to be discovered. It is the first committed enzyme in flavonoid biosynthesis. The enzyme catalyzes the conversion of 4-coumaroyl-CoA and malonyl-CoA to naringenin chalcone.

<span class="mw-page-title-main">Flavonoid biosynthesis</span>

Flavonoids are synthesized by the phenylpropanoid metabolic pathway in which the amino acid phenylalanine is used to produce 4-coumaroyl-CoA. This can be combined with malonyl-CoA to yield the true backbone of flavonoids, a group of compounds called chalcones, which contain two phenyl rings. Conjugate ring-closure of chalcones results in the familiar form of flavonoids, the three-ringed structure of a flavone. The metabolic pathway continues through a series of enzymatic modifications to yield flavanones → dihydroflavonols → anthocyanins. Along this pathway, many products can be formed, including the flavonols, flavan-3-ols, proanthocyanidins (tannins) and a host of other various polyphenolics.

<span class="mw-page-title-main">Sakuranetin</span> Chemical compound

Sakuranetin is a flavan-on, the 7-methoxy derivative of naringenin, found in Polymnia fruticosa and rice, where it acts as a phytoalexin against spore germination of Pyricularia oryzae.

Coumaroyl-coenzyme A is the thioester of coenzyme-A and coumaric acid. Coumaroyl-coenzyme A is a central intermediate in the biosynthesis of myriad natural products found in plants. These products include lignols, flavonoids, isoflavonoids, coumarins, aurones, stilbenes, catechin, and other phenylpropanoids.

The molecular formula C23H24O12 (exact mass: 492.12677623) may refer to:

Flavonolignans are natural phenols composed of a part flavonoid and a part phenylpropane.

<span class="mw-page-title-main">Chalconoid</span> Natural phenols related to chalcone

Chalconoids, also known as chalcones, are natural phenols derived from chalcone. They form the central core for a variety of important biological compounds.

The biosynthesis of isoflavonoids involves several enzymes; These are:

The biosynthesis of phenylpropanoids involves a number of enzymes.

Aureusidin synthase is an enzyme with systematic name 2',4,4',6'-tetrahydroxychalcone 4'-O-beta-D-glucoside:oxygen oxidoreductase.

Naringenin 7-O-methyltransferase is a methyltransferase isolated from rice, which catalyzes the biosynthesis of sakuranetin.

<i>Teucrium gnaphalodes</i> Species of flowering plant

Teucrium gnaphalodes is a plant species in the genus Teucrium. It is endemic to the Iberian Peninsula and grows at altitudes between 200 and 1500 m. It flowers from March to July.

References

  1. The rice bran constituent tricin potently inhibits cyclooxygenase enzymes and interferes with intestinal carcinogenesis in ApcMin mice
  2. 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.
  3. 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.
  4. 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.
  5. Wenzig, Eva (2005). "Flavonolignans from Avena sativa". Journal of Natural Products. 68 (2): 289–292. doi:10.1021/np049636k. PMID   15730266.