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1.1.1.144

Accepted name:

perillyl-alcohol dehydrogenase

Reaction:

perillyl alcohol + NAD⁺ = perillyl aldehyde + NADH + H⁺

For diagram of (-)-carvone, perillyl aldehyde and pulegone biosynthesis, click here

Other name(s):

perillyl alcohol dehydrogenase

Systematic name:

perillyl-alcohol:NAD⁺ oxidoreductase

Comments:

Oxidizes a number of primary alcohols with the alcohol group allylic to an endocyclic double bond and a 6-membered ring, either aromatic or hydroaromatic.

Links to other databases:

BRENDA, EAWAG-BBD, EXPASY, KEGG, MetaCyc, CAS registry number: 37250-73-0

References:

1.	Ballal, N.R., Bhattacharyya, P.K. and Rangachari, P.N. Perillyl alcohol dehydrogenase from a soil pseudomonad. Biochem. Biophys. Res. Commun. 23 (1966) 473–478. [DOI] [PMID: 4289759]

[EC 1.1.1.144 created 1972]

1.1.1.347

Accepted name:

geraniol dehydrogenase (NAD⁺)

Reaction:

geraniol + NAD⁺ = geranial + NADH + H⁺

Other name(s):

GeDH; geoA (gene name)

Systematic name:

geraniol:NAD⁺ oxidoreductase

Comments:

The enzyme from the bacterium Castellaniella defragrans is most active in vitro with perillyl alcohol [2]. The enzyme from the prune mite Carpoglyphus lactis also acts (more slowly) on farnesol but not on nerol [1].

Links to other databases:

BRENDA, EAWAG-BBD, EXPASY, KEGG, MetaCyc

References:

1.	Noge, K., Kato, M., Mori, N., Kataoka, M., Tanaka, C., Yamasue, Y., Nishida, R. and Kuwahara, Y. Geraniol dehydrogenase, the key enzyme in biosynthesis of the alarm pheromone, from the astigmatid mite Carpoglyphus lactis (Acari: Carpoglyphidae). FEBS J. 275 (2008) 2807–2817. [DOI] [PMID: 18422649]
2.	Lüddeke, F., Wülfing, A., Timke, M., Germer, F., Weber, J., Dikfidan, A., Rahnfeld, T., Linder, D., Meyerdierks, A. and Harder, J. Geraniol and geranial dehydrogenases induced in anaerobic monoterpene degradation by Castellaniella defragrans. Appl. Environ. Microbiol. 78 (2012) 2128–2136. [DOI] [PMID: 22286981]

[EC 1.1.1.347 created 2013]

1.14.13.47

Transferred entry:

(S)-limonene 3-monooxygenase. Now EC 1.14.14.99, (S)-limonene 3-monooxygenase

[EC 1.14.13.47 created 1992, modified 2003, deleted 2018]

1.14.13.48

Transferred entry:

(S)-limonene 6-monooxygenase. Now classified as EC 1.14.14.51, (S)-limonene 6-monooxygenase

[EC 1.14.13.48 created 1992, modified 2003, deleted 2017]

1.14.13.49

Transferred entry:

(S)-limonene 7-monooxygenase. Now classified as EC 1.14.14.52, (S)-limonene 7-monooxygenase

[EC 1.14.13.49 created 1992, modified 2003, deleted 2017]

1.14.14.51

Accepted name:

(S)-limonene 6-monooxygenase

Reaction:

(S)-limonene + [reduced NADPH—hemoprotein reductase] + O₂ = (–)-trans-carveol + [oxidized NADPH—hemoprotein reductase] + H₂O

For diagram of perillyl alcohol, isopiperitol and carveol biosynthesis, click here

Glossary:

limonene = a monoterpenoid
(S)-limonene = (–)-limonene

Other name(s):

(–)-limonene 6-hydroxylase; (–)-limonene 6-monooxygenase; (–)-limonene,NADPH:oxygen oxidoreductase (6-hydroxylating)

Systematic name:

(S)-limonene,[reduced NADPH—hemoprotein reductase]:oxygen oxidoreductase (6-hydroxylating)

Comments:

A cytochrome P-450 (heme thiolate) enzyme. The enzyme participates in the biosynthesis of (–)-carvone, which is responsible for the aroma of spearmint.

Links to other databases:

BRENDA, EAWAG-BBD, EXPASY, KEGG, MetaCyc, PDB, CAS registry number: 138066-93-0

References:

Karp, F., Mihaliak, C.A., Harris, J.L. and Croteau, R. Monoterpene biosynthesis: specificity of the hydroxylations of (-)-limonene by enzyme preparations from peppermint (Mentha piperita), spearmint (Mentha spicata), and perilla (Perilla frutescens) leaves. Arch. Biochem. Biophys. 276 (1990) 219–226. [DOI] [PMID: 2297225]

[EC 1.14.14.51 created 1992 as EC 1.14.13.48, modified 2003, transferred 2017 to EC 1.14.14.51]

1.14.14.52

Accepted name:

(S)-limonene 7-monooxygenase

Reaction:

(S)-limonene + [reduced NADPH—hemoprotein reductase] + O₂ = (–)-perillyl alcohol + [oxidized NADPH—hemoprotein reductase] + H₂O

For diagram of perillyl alcohol, isopiperitol and carveol biosynthesis, click here

Glossary:

limonene = a monoterpenoid
(S)-limonene = (–)-limonene

Other name(s):

(–)-limonene 7-monooxygenase; (–)-limonene hydroxylase; (–)-limonene monooxygenase; (–)-limonene,NADPH:oxygen oxidoreductase (7-hydroxylating)

Systematic name:

(S)-limonene,[reduced NADPH—hemoprotein reductase]:oxygen oxidoreductase (7-hydroxylating)

Comments:

A cytochrome P-450 (heme thiolate) enzyme. The enzyme, characterized from the plant Perilla frutescens, participates in the biosynthesis of perillyl aldehyde, the major constituent of the essential oil that accumulates in the glandular trichomes of this plant. Some forms of the enzyme also catalyse the oxidation of (–)-perillyl alcohol to (–)-perillyl aldehyde.

Links to other databases:

BRENDA, EAWAG-BBD, EXPASY, KEGG, MetaCyc, PDB, CAS registry number: 122653-75-2

References:

1.	Karp, F., Mihaliak, C.A., Harris, J.L. and Croteau, R. Monoterpene biosynthesis: specificity of the hydroxylations of (-)-limonene by enzyme preparations from peppermint (Mentha piperita), spearmint (Mentha spicata), and perilla (Perilla frutescens) leaves. Arch. Biochem. Biophys. 276 (1990) 219–226. [DOI] [PMID: 2297225]
2.	Mau, C.J., Karp, F., Ito, M., Honda, G. and Croteau, R.B. A candidate cDNA clone for (–)-limonene-7-hydroxylase from Perilla frutescens. Phytochemistry 71 (2010) 373–379. [DOI] [PMID: 20079506]
3.	Fujiwara, Y. and Ito, M. Molecular cloning and characterization of a Perilla frutescens cytochrome P450 enzyme that catalyzes the later steps of perillaldehyde biosynthesis. Phytochemistry 134 (2017) 26–37. [DOI] [PMID: 27890582]

[EC 1.14.14.52 created 1992 as EC 1.14.13.49, modified 2003, transferred 2017 to EC 1.14.14.52]

1.14.14.99

Accepted name:

(S)-limonene 3-monooxygenase

Reaction:

(S)-limonene + [reduced NADPH—hemoprotein reductase] + O₂ = (–)-trans-isopiperitenol + [oxidized NADPH—hemoprotein reductase] + H₂O

For diagram of perillyl alcohol, isopiperitol and carveol biosynthesis, click here

Glossary:

limonene = a monoterpenoid
(S)-limonene = (–)-limonene

Other name(s):

(–)-limonene 3-hydroxylase; (–)-limonene 3-monooxygenase; CYP71D15 (gene name)

Systematic name:

(S)-limonene,[reduced NADPH—hemoprotein reductase]:oxygen oxidoreductase (3-hydroxylating)

Comments:

A cytochrome P-450 (heme-thiolate) protein from peppermint (Mentha piperita).

Links to other databases:

BRENDA, EAWAG-BBD, EXPASY, KEGG, MetaCyc, CAS registry number: 138066-92-9

References:

1.	Karp, F., Mihaliak, C.A., Harris, J.L. and Croteau, R. Monoterpene biosynthesis: specificity of the hydroxylations of (-)-limonene by enzyme preparations from peppermint (Mentha piperita), spearmint (Mentha spicata), and perilla (Perilla frutescens) leaves. Arch. Biochem. Biophys. 276 (1990) 219–226. [DOI] [PMID: 2297225]
2.	Lupien, S., Karp, F., Wildung, M. and Croteau, R. Regiospecific cytochrome P450 limonene hydroxylases from mint (Mentha) species: cDNA isolation, characterization, and functional expression of (–)-4S-limonene-3-hydroxylase and (–)-4S-limonene-6-hydroxylase. Arch. Biochem. Biophys. 368 (1999) 181–192. [PMID: 10415126]
3.	Wust, M., Little, D.B., Schalk, M. and Croteau, R. Hydroxylation of limonene enantiomers and analogs by recombinant (–)-limonene 3- and 6-hydroxylases from mint (Mentha) species: evidence for catalysis within sterically constrained active sites. Arch. Biochem. Biophys. 387 (2001) 125–136. [PMID: 11368174]

[EC 1.14.14.99 created 1992 as EC 1.14.13.47, modified 2003, transferred 2018 1.14.14.99]

1.17.99.8

Accepted name:

limonene dehydrogenase

Reaction:

(1) (S)-limonene + H₂O + acceptor = (–)-perillyl alcohol + reduced acceptor
(2) (R)-limonene + H₂O + acceptor = (+)-perillyl alcohol + reduced acceptor

Glossary:

limonene = 1-methyl-4-(prop-1-en-2-yl)cyclohex-1-ene
perillyl alcohol = [4-(prop-1-en-2-yl)cyclohex-1-en-1-yl]methanol
(–)-perillyl alcohol = (S)-perillyl alcohol = [(4S)-4-(prop-1-en-2-yl)cyclohex-1-en-1-yl]methanol
(+)-perillyl alcohol = (R)-perillyl alcohol = [(4R)-4-(prop-1-en-2-yl)cyclohex-1-en-1-yl]methanol
(–)-limonene = (S)-limonene = (4S)-1-methyl-4-(prop-1-en-2-yl)cyclohexene
(+)-limonene = (R)-limonene = (4R)-1-methyl-4-(prop-1-en-2-yl)cyclohexene

Other name(s):

ctmAB (gene names)

Systematic name:

limonene:acceptor oxidoreductase (7-hydroxylating)

Comments:

Contains FAD. The enzyme, characterized from the bacterium Castellaniella defragrans 65Phen, hydroxylates the R- and S-enantiomers at a similar rate. The in vivo electron acceptor may be a heterodimeric electron transfer flavoprotein (ETF).

Links to other databases:

BRENDA, EXPASY, KEGG, MetaCyc

References:

1.	Petasch, J., Disch, E.M., Markert, S., Becher, D., Schweder, T., Huttel, B., Reinhardt, R. and Harder, J. The oxygen-independent metabolism of cyclic monoterpenes in Castellaniella defragrans 65Phen. BMC Microbiol. 14:164 (2014). [PMID: 24952578]
2.	Puentes-Cala, E., Liebeke, M., Markert, S. and Harder, J. Limonene dehydrogenase hydroxylates the allylic methyl group of cyclic monoterpenes in the anaerobic terpene degradation by Castellaniella defragrans. J. Biol. Chem. 293 (2018) 9520–9529. [PMID: 29716998]

[EC 1.17.99.8 created 2020]

4.2.3.16

Accepted name:

(4S)-limonene synthase

Reaction:

geranyl diphosphate = (S)-limonene + diphosphate

For diagram of perillyl alcohol, isopiperitol and carveol biosynthesis, click here

Glossary:

limonene = a monoterpenoid
(S)-limonene = (-)-limonene

Other name(s):

(-)-(4S)-limonene synthase; 4S-(-)-limonene synthase; geranyldiphosphate diphosphate lyase (limonene forming); geranyldiphosphate diphosphate lyase [cyclizing, (4S)-limonene-forming]; geranyl-diphosphate diphosphate-lyase [cyclizing; (-)-(4S)-limonene-forming]

Systematic name:

geranyl-diphosphate diphosphate-lyase [cyclizing; (S)-limonene-forming]

Comments:

A recombinant enzyme (also known as a monoterpene synthase or cyclase) from the grand fir (Abies grandis) requires Mn²⁺ and K⁺ for activity. Mg²⁺ is essentially ineffective as the divalent metal ion cofactor.

Links to other databases:

BRENDA, EXPASY, KEGG, MetaCyc, CAS registry number: 110639-20-8

References:

1.	Bohlmann, J., Steele, C.L. and Croteau, R. Monoterpene synthases from grand fir (Abies grandis). cDNA isolation, characterization, and functional expression of myrcene synthase, (-)-(4S)-limonene synthase, and (-)-(1S,5S)-pinene synthase. J. Biol. Chem. 272 (1997) 21784–21792. [DOI] [PMID: 9268308]
2.	Collby, S.M., Alonso, W.R., Katahira, E.J., McGarvey, D.J. and Croteau, R. 4S-Limonene synthase from the oil glands of spearmint (Mentha spicata). cDNA isolation, characterization, and bacterial expression of the catalytically active monoterpene cyclase. J. Biol. Chem. 268 (1993) 23016–23024. [PMID: 8226816]
3.	Yuba, A., Yazaki, K., Tabata, M., Honda, G. and Croteau, R. cDNA cloning, characterization, and functional expression of 4S-(-)-limonene synthase from Perilla frutescens. Arch. Biochem. Biophys. 332 (1996) 280–287. [DOI] [PMID: 8806736]

[EC 4.2.3.16 created 2000 as EC 4.1.99.10, transferred 2000 to EC 4.2.3.16, modified 2003]