Phenylpropanoids metabolism

The biosynthesis of phenylpropanoids involves a number of enzymes.

## Contents

* 1 From amino acids to cinnamates
* 1.1 Enzymes associated with biosynthesis of hydroxycinnamic acids
* 1.1.1 Conjugation enzymes
* 1.1.2 Deconjugation enzymes
* 1.2 Stilbenoids biosynthesis
* 1.3 Coumarins biosynthesis
* 1.4 Chalcones biosynthesis
* 1.5 Flavonoids biosynthesis
* 2 Biodegradation
* 2.1 Hydroxycinnamic acids degradation
* 3 References

## From amino acids to cinnamates

In plants, all phenylpropanoids are derived from the amino acids phenylalanine and tyrosine.

Phenylalanine ammonia-lyase (PAL, a.k.a. phenylalanine/tyrosine ammonia-lyase) is an enzyme that transforms L-phenylalanine and tyrosine into trans-cinnamic acid and p-coumaric acid, respectively.

Trans-cinnamate 4-monooxygenase (cinnamate 4-hydroxylase) is the enzyme that transforms trans-cinnamate into 4-hydroxycinnamate (p-coumaric acid). 4-Coumarate-CoA ligase is the enzyme that transforms 4-coumarate (p-coumaric acid) into 4-coumaroyl-CoA.[1]

### Enzymes associated with biosynthesis of hydroxycinnamic acids

* Cinnamyl-alcohol dehydrogenase (CAD), an enzyme that transforms cinnamyl alcohol into cinnamaldehyde
* Sinapine esterase, an enzyme that transforms sinapoylcholine into sinapate (sinapic acid) and choline
* Trans-cinnamate 2-monooxygenase, an enzyme that transforms trans-cinnamate (cinnamic acid) into 2-hydroxycinnamate
* Caffeate O-methyltransferase, an enzyme that transforms caffeic acid into ferulic acid
* Caffeoyl-CoA O-methyltransferase, an enzyme that transforms caffeoyl-CoA into feruloyl-CoA
* 5-O-(4-coumaroyl)-D-quinate 3'-monooxygenase, an enzyme that transforms trans-5-O-(4-coumaroyl)-D-quinate into trans-5-O-caffeoyl-D-quinate
* Sinapoylglucose—choline O-sinapoyltransferase, an enzyme that transforms 1-O-sinapoyl-beta-D-glucose into sinapoylcholine (sinapine)
* Sinapoylglucose—malate O-sinapoyltransferase, an enzyme that transforms 1-O-sinapoyl-beta-D-glucose into sinapoyl-(S)-malate
* Cinnamoyl-CoA reductase, an enzyme that transforms cinnamoyl-CoA from cinnamaldehyde

#### Conjugation enzymes

These enzymes conjugate phenylpropanoids to other molecules.

* 2-coumarate O-beta-glucosyltransferase, the enzyme that transforms trans-2-hydroxycinnamate into trans-beta-D-glucosyl-2-hydroxycinnamate
* Hydroxycinnamate 4-beta-glucosyltransferase, the enzyme that transforms p-coumaric acid into 4-O-beta-D-glucosyl-4-hydroxycinnamate
* Shikimate O-hydroxycinnamoyltransferase, the enzyme that transforms 4-coumaroyl-CoA into 4-coumaroylshikimate
* Quinate O-hydroxycinnamoyltransferase, the enzyme that transforms feruloyl-CoA into O-feruloylquinate
* Sinapate 1-glucosyltransferase, the enzyme that transforms sinapate (sinapic acid) into 1-sinapoyl-D-glucose
* Coniferyl-alcohol glucosyltransferase, the enzyme that transforms coniferyl alcohol into coniferin

#### Deconjugation enzymes

* Coniferin beta-glucosidase, in the glucosidase that transforms coniferin into coniferol

### Stilbenoids biosynthesis

* Pinosylvin synthase, an enzyme that transforms pinosylvin from cinnamoyl-CoA
* Trihydroxystilbene synthase, an enzyme that transforms 4-coumaroyl-CoA to resveratrol.

An alternative bacterial ketosynthase-directed stilbenoids biosynthesis pathway exists in Photorhabdus bacterial symbionts of Heterorhabditis nematodes, producing 3,5-dihydroxy-4-isopropyl-trans-stilbene for antibiotic purposes.[2]

### Coumarins biosynthesis

* Scopoletin glucosyltransferase, the enzyme that transforms scopoletin into scopolin

### Chalcones biosynthesis

4-Coumaroyl-CoA can be combined with malonyl-CoA to yield the true backbone of flavonoids, a group of compounds called chalconoids, which contain two phenyl rings. Naringenin-chalcone synthase is an enzyme that catalyzes the following conversion:

3-malonyl-CoA + 4-coumaroyl-CoA → 4 CoA + naringenin chalcone + 3 CO2

### Flavonoids biosynthesis

Main article: Biology:Flavonoid biosynthesis

Conjugate ring-closure of chalcones results in the familiar form of flavonoids, the three-ringed structure of a flavone.

## Biodegradation

### Hydroxycinnamic acids degradation

* Caffeate 3,4-dioxygenase is an enzyme that uses 3,4-dihydroxy-trans-cinnamate (caffeic acid) and oxygen to produce 3-(2-carboxyethenyl)-cis,cis-muconate.

## References

1. ↑ Ververidis Filippos, F.; Trantas Emmanouil; Douglas Carl; Vollmer Guenter; Kretzschmar Georg; Panopoulos Nickolas (October 2007). "Biotechnology of flavonoids and other phenylpropanoid-derived natural products. Part I: Chemical diversity, impacts on plant biology and human health". Biotechnology Journal 2 (10): 1214–34. doi:10.1002/biot.200700084. PMID 17935117.
2. ↑ "Bacterial biosynthesis of a multipotent stilbene". Angew Chem Int Ed Engl 47 (10): 1942–5. 2008. doi:10.1002/anie.200705148. PMID 18236486.

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