The Enzyme Database

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EC 1.1.1.237     
Accepted name: hydroxyphenylpyruvate reductase
Reaction: (1) (R)-3-(4-hydroxyphenyl)lactate + NAD(P)+ = 3-(4-hydroxyphenyl)pyruvate + NAD(P)H + H+
(2) (R)-3-(3,4-dihydroxyphenyl)lactate + NAD(P)+ = 3-(3,4-dihydroxyphenyl)pyruvate + NAD(P)H + H+
For diagram of 4-hydroxyphenylpyruvate metabolites, click here and for diagram of rosmarinate biosynthesis, click here
Other name(s): HPPR
Systematic name: (R)-3-(4-hydroxyphenyl)lactate:NAD(P)+ oxidoreductase
Comments: The enzyme participates in the biosynthesis of rosmarinic acid. It belongs to the family of D-isomer-specific 2-hydroxyacid dehydrogenases, and prefers NADPH to NADH.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc, PDB, CAS registry number: 117590-77-9
References:
1.  Petersen, M. and Alfermann, A.W. Two new enzymes of rosmarinic acid biosynthesis from cell cultures of Coleus blumei: hydroxyphenylpyruvate reductase and rosmarinic acid synthase. Z. Naturforsch. C: Biosci. 43 (1988) 501–504.
2.  Kim, K.H., Janiak, V. and Petersen, M. Purification, cloning and functional expression of hydroxyphenylpyruvate reductase involved in rosmarinic acid biosynthesis in cell cultures of Coleus blumei. Plant Mol. Biol. 54 (2004) 311–323. [PMID: 15284489]
3.  Kim, Y.B., Uddina, M.R., Kim, Y., Park, C.G. and Park, S.U. Molecular cloning and characterization of tyrosine aminotransferase and hydroxyphenylpyruvate reductase, and rosmarinic acid accumulation in Scutellaria baicalensis. Nat. Prod. Commun. 9 (2014) 1311–1314. [PMID: 25918800]
4.  Wang, G.Q., Chen, J.F., Yi, B., Tan, H.X., Zhang, L. and Chen, W.S. HPPR encodes the hydroxyphenylpyruvate reductase required for the biosynthesis of hydrophilic phenolic acids in Salvia miltiorrhiza. Chin J Nat Med 15 (2017) 917–927. [PMID: 29329649]
[EC 1.1.1.237 created 1992, modified 2018]
 
 
EC 2.3.1.140     
Accepted name: rosmarinate synthase
Reaction: caffeoyl-CoA + (R)-3-(3,4-dihydroxyphenyl)lactate = CoA + rosmarinate
For diagram of rosmarinate biosynthesis, click here
Glossary: (R)-3-(3,4-dihydroxyphenyl)lactate = (2R)-3-(3,4-dihydroxyphenyl)-2-hydroxypropanoate
rosmarinate = (2R)-3-(3,4-dihydroxyphenyl)-2-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}propanoate
Other name(s): rosmarinic acid synthase; caffeoyl-coenzyme A:3,4-dihydroxyphenyllactic acid caffeoyltransferase; 4-coumaroyl-CoA:4-hydroxyphenyllactic acid 4-coumaroyl transferase; RAS (gene name)
Systematic name: caffeoyl-CoA:(R)-3-(3,4-dihydroxyphenyl)lactate 2′-O-caffeoyl-transferase
Comments: Involved, with EC 1.1.1.237 (hydroxyphenylpyruvate reductase) in the biosynthesis of rosmarinic acid. Characterized from the plant Melissa officinalis L. (lemon balm).
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc, CAS registry number: 117590-80-4
References:
1.  Petersen, M. and Alfermann, A.W. Two new enzymes of rosmarinic acid biosynthesis from cell cultures of Coleus blumei: hydroxyphenylpyruvate reductase and rosmarinic acid synthase. Z. Naturforsch. C: Biosci. 43 (1988) 501–504.
2.  Petersen, M. S. Characterization of rosmarinic acid synthase from cell cultures of Coleus blumei. Phytochemistry 30 (1991) 2877–2881.
3.  Weitzel, C. and Petersen, M. Cloning and characterisation of rosmarinic acid synthase from Melissa officinalis L. Phytochemistry 72 (2011) 572–578. [DOI] [PMID: 21354582]
[EC 2.3.1.140 created 1992, modified 2013]
 
 


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