Coumaroyl-coenzyme A is the

thioester In organic chemistry, thioesters are organosulfur compounds with the molecular structure . They are analogous to carboxylate esters () with the sulfur in the thioester replacing oxygen in the carboxylate ester, as implied by the thio- prefix ...

of coenzyme-A and

coumaric acid Coumaric acid is a phenolic derivative of cinnamic acid having a hydroxy group as substituent at one of the aromatic In organic chemistry, aromaticity is a chemical property describing the way in which a conjugated system, conjugated ring of un ...

. Coumaroyl-coenzyme A is a central intermediate in the biosynthesis of myriad natural products found in plants. These products include lignols (precursors to

lignin Lignin is a class of complex organic polymers that form key structural materials in the support tissues of most plants. Lignins are particularly important in the formation of cell walls, especially in wood and bark, because they lend rigidit ...

and

lignocellulose Lignocellulose refers to plant dry matter (biomass), so called lignocellulosic biomass. It is the most abundantly available raw material on the Earth for the production of Biofuel, biofuels. It is composed of two kinds of carbohydrate polymers, c ...

flavonoids Flavonoids (or bioflavonoids; from the Latin word ''flavus'', meaning yellow, their color in nature) are a class of polyphenolic secondary metabolites found in plants, and thus commonly consumed in the diets of humans. Chemically, flavonoids ...

isoflavonoids Isoflavonoids are a class of flavonoid phenolic compounds, many of which are biologically active. Isoflavonoids and their derivatives are sometimes referred to as phytoestrogens, as many isoflavonoid compounds have biological effects via the estr ...

coumarin Coumarin () or 2''H''-chromen-2-one is an aromatic organic chemical compound with formula . Its molecule can be described as a benzene molecule with two adjacent hydrogen atoms replaced by an unsaturated lactone ring , forming a second six-me ...

aurones An aurone is a heterocyclic chemical compound, which is a type of flavonoid. There are two isomers of the molecule, with (''E'')- and (''Z'')-configurations. The molecule contains a benzofuran element associated with a benzylidene linked in posi ...

stilbenes Stilbenoids are hydroxylated derivatives of stilbene. They have a C6–C2–C6 structure. In biochemical terms, they belong to the family of phenylpropanoids and share most of their biosynthesis pathway with chalcones. Most stilbenoids are produ ...

catechin Catechin is a flavan-3-ol, a type of secondary metabolite providing antioxidant roles in plants. It belongs to the subgroup of polyphenols called flavonoids. The name of the catechin chemical family derives from ''catechu'', which is the tannic ...

, and other

phenylpropanoid The phenylpropanoids are a diverse family of organic compounds that are biosynthesized by plants from the amino acids phenylalanine and tyrosine in the shikimic acid pathway. Their name is derived from the six-carbon, aromatic phenyl group and ...

Biosynthesis and significance

It is generated in nature from

phenylalanine Phenylalanine (symbol Phe or F) is an essential α-amino acid with the chemical formula, formula . It can be viewed as a benzyl group substituent, substituted for the methyl group of alanine, or a phenyl group in place of a terminal hydrogen of ...

, which is converted by

PAL Phase Alternating Line (PAL) is a color encoding system for analog television. It was one of three major analogue colour television standards, the others being NTSC and SECAM. In most countries it was broadcast at 625 lines, 50 fields (25 ...

to trans-

cinnamate Cinnamic acid is an organic compound with the formula C6H5-CH=CH- COOH. It is a white crystalline compound that is slightly soluble in water, and freely soluble in many organic solvents. Classified as an unsaturated carboxylic acid, it occurs nat ...

. Trans-cinnamate is hydroxylated by trans-cinnamate 4-monooxygenase to give 4-hydroxycinnamate (i.e, coumarate). Coumarate is condensed with coenzyme-A in the presence of

4-coumarate-CoA ligase In enzymology, a 4-coumarate—CoA ligase () is an enzyme that catalyzes the chemical reaction :ATP + 4-coumarate + CoA \rightleftharpoons AMP + diphosphate + 4-coumaroyl-CoA The 3 substrates of this enzyme are ATP, 4-coumarate, and CoA, whe ...

: :ATP + 4-coumarate + CoA

\rightleftharpoons

AMP + diphosphate + 4-coumaroyl-CoA.

Enzymes using Coumaroyl-Coenzyme A

Anthocyanin 3-O-glucoside 6''-O-hydroxycinnamoyltransferase Anthocyanin 3-O-glucoside 6″-O-hydroxycinnamoyltransferase is an enzyme forming delphinidin 3-(6-''p''-coumaroyl)glucoside from delphinidin 3-''O''-glucoside (myrtillin) and ''p''-coumaroyl-CoA. It is an enzyme in the anthocyanin biosynthes ...

Anthocyanin 5-aromatic acyltransferase In enzymology, an anthocyanin 5-aromatic acyltransferase () is an enzyme that catalyzes the chemical reaction :hydroxycinnamoyl-CoA + anthocyanidin-3,5-diglucoside \rightleftharpoons CoA + anthocyanidin 3-glucoside-5-hydroxycinnamoylglucoside Thu ...

Chalcone synthase 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 ...

4-Coumarate-CoA ligase In enzymology, a 4-coumarate—CoA ligase () is an enzyme that catalyzes the chemical reaction :ATP + 4-coumarate + CoA \rightleftharpoons AMP + diphosphate + 4-coumaroyl-CoA The 3 substrates of this enzyme are ATP, 4-coumarate, and CoA, whe ...

6'-Deoxychalcone synthase In enzymology, a 6'-deoxychalcone synthase () is an enzyme that catalyzes the chemical reaction :3 malonyl-CoA + 4-coumaroyl-CoA + NADPH + H+ \rightleftharpoons 4 CoA + isoliquiritigenin + 3 CO2 + NADP+ + H2O The 4 substrates of this enzyme are ...

Agmatine N4-coumaroyltransferase In enzymology, an agmatine N4-coumaroyltransferase () is an enzyme that catalysis, catalyzes the chemical reaction :4-coumaroyl-CoA + agmatine \rightleftharpoons CoA + N-(4-guanidinobutyl)-4-hydroxycinnamamide Thus, the two substrate (biochemistr ...

Flavonol-3-O-triglucoside O-coumaroyltransferase In enzymology, a flavonol-3-O-triglucoside O-coumaroyltransferase () is an enzyme that catalyzes the chemical reaction :4-coumaroyl-CoA + a flavonol 3-O- 2)-beta-D-glucosyl-(1->2)-beta-D-glucoside">eta-D-glucosyl-(1->2)-beta-D-glucosyl-(1->2)-beta ...

Naringenin-chalcone synthase 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 ...

Shikimate O-hydroxycinnamoyltransferase In enzymology, a shikimate O-hydroxycinnamoyltransferase () is an enzyme that catalyzes the chemical reaction :4-coumaroyl-CoA + shikimate \rightleftharpoons CoA + 4-coumaroylshikimate Thus, the two substrates of this enzyme are 4-coumaroyl-CoA ...

Trihydroxystilbene synthase In enzymology, a trihydroxystilbene synthase () is an enzyme that catalyzes the chemical reaction :3 malonyl-CoA + 4-coumaroyl-CoA \rightleftharpoons 4 CoA + 3,4',5-trihydroxy-stilbene + 4 CO2 Thus, the two substrates of this enzyme are malonyl- ...

References

Thioesters of coenzyme A Hydroxycinnamic acid esters {{Aromatic-stub