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1.14.11.61

Accepted name:

feruloyl-CoA 6-hydroxylase

Reaction:

trans-feruloyl-CoA + 2-oxoglutarate + O₂ = trans-6-hydroxyferuloyl-CoA + succinate + CO₂

Glossary:

trans-feruloyl-CoA = 4-hydroxy-3-methoxycinnamoyl-CoA = (E)-3-(4-hydroxy-3-methoxyphenyl)propenoyl-CoA

Systematic name:

feruloyl-CoA,2-oxoglutarate:oxygen oxidoreductase (6-hydroxylating)

Comments:

Requires iron(II) and ascorbate. The product spontaneously undergoes trans-cis isomerization and lactonization to form scopoletin, liberating CoA in the process. The enzymes from the plants Ruta graveolens and Ipomoea batatas also act on trans-4-coumaroyl-CoA. cf. EC 1.14.11.62, trans-4-coumaroyl-CoA 2-hydroxylase.

Links to other databases:

BRENDA, EXPASY, KEGG, MetaCyc, PDB

References:

1.	Kai, K., Mizutani, M., Kawamura, N., Yamamoto, R., Tamai, M., Yamaguchi, H., Sakata, K. and Shimizu, B. Scopoletin is biosynthesized via ortho-hydroxylation of feruloyl CoA by a 2-oxoglutarate-dependent dioxygenase in Arabidopsis thaliana. Plant J. 55 (2008) 989–999. [PMID: 18547395]
2.	Bayoumi, S.A., Rowan, M.G., Blagbrough, I.S. and Beeching, J.R. Biosynthesis of scopoletin and scopolin in cassava roots during post-harvest physiological deterioration: the E-Z-isomerisation stage. Phytochemistry 69 (2008) 2928–2936. [PMID: 19004461]
3.	Vialart, G., Hehn, A., Olry, A., Ito, K., Krieger, C., Larbat, R., Paris, C., Shimizu, B., Sugimoto, Y., Mizutani, M. and Bourgaud, F. A 2-oxoglutarate-dependent dioxygenase from Ruta graveolens L. exhibits p-coumaroyl CoA 2′-hydroxylase activity (C2′H): a missing step in the synthesis of umbelliferone in plants. Plant J. 70 (2012) 460–470. [DOI] [PMID: 22168819]
4.	Matsumoto, S., Mizutani, M., Sakata, K. and Shimizu, B. Molecular cloning and functional analysis of the ortho-hydroxylases of p-coumaroyl coenzyme A/feruloyl coenzyme A involved in formation of umbelliferone and scopoletin in sweet potato, Ipomoea batatas (L.) Lam. Phytochemistry 74 (2012) 49–57. [PMID: 22169019]

[EC 1.14.11.61 created 2019]

1.14.11.62

Accepted name:

trans-4-coumaroyl-CoA 2-hydroxylase

Reaction:

trans-4-coumaroyl-CoA + 2-oxoglutarate + O₂ = 2,4-dihydroxycinnamoyl-CoA + succinate + CO₂

Glossary:

trans-4-coumaroyl-CoA = (2E)-3-(4-hydroxyphenyl)prop-2-enoyl-CoA
2,4-dihydroxycinnamoyl-CoA = (2E)-3-(2,4-dihydroxyphenyl)prop-2-enoyl-CoA
umbelliferone = 7-hydroxycoumarin

Other name(s):

Diox4 (gene name); C2′H (gene name)

Systematic name:

(2E)-3-(4-hydroxyphenyl)prop-2-enoyl-CoA,2-oxoglutarate:oxygen oxidoreductase (2-hydroxylating)

Comments:

Requires iron(II) and ascorbate. The product spontaneously undergoes trans-cis isomerization followed by lactonization and cyclization, liberating CoA and forming umbelliferone. The enzymes from the plants Ruta graveolens and Ipomoea batatas also act on trans-feruloyl-CoA (cf. EC 1.14.11.61, feruloyl-CoA 6-hydroxylase).

Links to other databases:

BRENDA, EXPASY, KEGG, MetaCyc

References:

1.	Vialart, G., Hehn, A., Olry, A., Ito, K., Krieger, C., Larbat, R., Paris, C., Shimizu, B., Sugimoto, Y., Mizutani, M. and Bourgaud, F. A 2-oxoglutarate-dependent dioxygenase from Ruta graveolens L. exhibits p-coumaroyl CoA 2′-hydroxylase activity (C2′H): a missing step in the synthesis of umbelliferone in plants. Plant J. 70 (2012) 460–470. [DOI] [PMID: 22168819]
2.	Matsumoto, S., Mizutani, M., Sakata, K. and Shimizu, B. Molecular cloning and functional analysis of the ortho-hydroxylases of p-coumaroyl coenzyme A/feruloyl coenzyme A involved in formation of umbelliferone and scopoletin in sweet potato, Ipomoea batatas (L.) Lam. Phytochemistry 74 (2012) 49–57. [PMID: 22169019]

[EC 1.14.11.62 created 2019]

2.4.1.17

Accepted name:

glucuronosyltransferase

Reaction:

UDP-α-D-glucuronate + acceptor = UDP + acceptor β-D-glucuronoside

Other name(s):

1-naphthol glucuronyltransferase; 1-naphthol-UDP-glucuronosyltransferase; 17β-hydroxysteroid UDP-glucuronosyltransferase; 3α-hydroxysteroid UDP-glucuronosyltransferase; 4-hydroxybiphenyl UDP-glucuronosyltransferase; 4-methylumbelliferone UDP-glucuronosyltransferase; 4-nitrophenol UDP-glucuronyltransferase; 4-nitrophenol UDPGT; 17-OH steroid UDPGT; 3-OH androgenic UDPGT; bilirubin uridine diphosphoglucuronyltransferase; bilirubin UDP-glucuronosyltransferase; bilirubin monoglucuronide glucuronyltransferase; bilirubin UDPGT; bilirubin glucuronyltransferase; ciramadol UDP-glucuronyltransferase; estriol UDP-glucuronosyltransferase; estrone UDP-glucuronosyltransferase; uridine diphosphoglucuronosyltransferase; uridine diphosphoglucuronate-bilirubin glucuronoside glucuronosyltransferase; uridine diphosphoglucuronate-bilirubin glucuronosyltransferase; uridine diphosphoglucuronate-estriol glucuronosyltransferase; uridine diphosphoglucuronate-estradiol glucuronosyltransferase; uridine diphosphoglucuronate-4-hydroxybiphenyl glucuronosyltransferase; uridine diphosphoglucuronate-1,2-diacylglycerol glucuronosyltransferase; uridine diphosphoglucuronate-estriol 16α-glucuronosyltransferase; GT; morphine glucuronyltransferase; p-hydroxybiphenyl UDP glucuronyltransferase; p-nitrophenol UDP-glucuronosyltransferase; p-nitrophenol UDP-glucuronyltransferase; p-nitrophenylglucuronosyltransferase; p-phenylphenol glucuronyltransferase; phenyl-UDP-glucuronosyltransferase; PNP-UDPGT; UDP glucuronate-estradiol-glucuronosyltransferase; UDP glucuronosyltransferase; UDP glucuronate-estriol glucuronosyltransferase; UDP glucuronic acid transferase; UDP glucuronyltransferase; UDP-glucuronate-4-hydroxybiphenyl glucuronosyltransferase; UDP-glucuronate-bilirubin glucuronyltransferase; UDP-glucuronosyltransferase; UDP-glucuronyltransferase; UDPGA transferase; UDPGA-glucuronyltransferase; UDPGT; uridine diphosphoglucuronyltransferase; uridine diphosphate glucuronyltransferase; uridine 5′-diphosphoglucuronyltransferase; UDP-glucuronate β-D-glucuronosyltransferase (acceptor-unspecific)

Systematic name:

UDP-α-D-glucuronate β-D-glucuronosyltransferase (acceptor-unspecific; configuration-inverting)

Comments:

This entry denotes a family of enzymes accepting a wide range of substrates, including phenols, alcohols, amines and fatty acids. Some of the activities catalysed were previously listed separately as EC 2.4.1.42, EC 2.4.1.59, EC 2.4.1.61, EC 2.4.1.76, EC 2.4.1.77, EC 2.4.1.84, EC 2.4.1.107 and EC 2.4.1.108. A temporary nomenclature for the various forms, whose delineation is in a state of flux, is suggested in Ref. 1.

Links to other databases:

BRENDA, EXPASY, KEGG, MetaCyc, PDB, CAS registry number: 9030-08-4

References:

1.	Bock, K.W., Burchell, B., Dutton, G.J., Hanninen, O., Mulder, G.J., Owens, I.S., Siest, G. and Jephly, T.R. UDP-glucuronosyltransferase activities. Guidelines for consistent interim terminology and assay conditions. Biochem. Pharmacol. 32 (1983) 953–955. [DOI] [PMID: 6404284]
2.	Bock, K.W., Josting, D., Lilienblum, W. and Pfeil, H. Purification of rat-liver microsomal UDP-glucuronyltransferase. Separation of two enzyme forms inducible by 3-methylcholanthrene or phenobarbital. Eur. J. Biochem. 98 (1979) 19–26. [DOI] [PMID: 111930]
3.	Burchell, B. Identification and purification of multiple forms of UDP-glucuronosyltransferase. Rev. Biochem. Toxicol. 3 (1981) 1–32.
4.	Dutton, G.J. Glucuronidation of Drugs and Other Compounds, C.R.C. Press, Boca Raton, Florida, 1980.
5.	Green, M.D., Falany, C.N., Kirkpatrick, R.B. and Tephly, T.R. Strain differences in purified rat hepatic 3α-hydroxysteroid UDP-glucuronosyltransferase. Biochem. J. 230 (1985) 403–409. [PMID: 3931633]
6.	Jansen, P.L.M. The enzyme-catalyzed formation of bilirubin diglucuronide by a solublized preparation from cat liver microsomes. Biochim. Biophys. Acta 338 (1974) 170–182.

[EC 2.4.1.17 created 1961 (EC 2.4.1.42, EC 2.4.1.59 and EC 2.4.1.61 all created 1972, EC 2.4.1.76, EC 2.4.1.77 and EC 2.4.1.84 all created 1976, EC 2.4.1.107 and EC 2.4.1.108 both created 1983, all incorporated 1984)]

2.4.1.104

Accepted name:

o-dihydroxycoumarin 7-O-glucosyltransferase

Reaction:

UDP-glucose + 7,8-dihydroxycoumarin = UDP + daphnin

Other name(s):

uridine diphosphoglucose-o-dihydroxycoumarin 7-O-glucosyltransferase; UDP-glucose:o-dihydroxycoumarin glucosyltransferase

Systematic name:

UDP-glucose:7,8-dihydroxycoumarin 7-O-β-D-glucosyltransferase

Comments:

Converts the aglycone daphetin into daphnin and, more slowly, esculetin into cichoriin, umbelliferone into skimmin, hydrangetin into hydrangin and scopoletin into scopolin.

Links to other databases:

BRENDA, EXPASY, KEGG, MetaCyc, CAS registry number: 74114-37-7

References:

1.	Ibrahim, R.K. and Boulay, B. Purification and some properties of UDP-glucose:o-hydroxycoumarin 7-O-glucosyltransferase from tobacco cell cultures. Plant Sci. Lett. 18 (1980) 177–184.

[EC 2.4.1.104 created 1983]

2.5.1.138

Accepted name:

coumarin 8-geranyltransferase

Reaction:

(1) geranyl diphosphate + umbelliferone = diphosphate + 8-geranylumbelliferone
(2) geranyl diphosphate + esculetin = diphosphate + 8-geranylesculetin

Glossary:

geranyl diphosphate = (2E)-3,7-dimethylocta-2,6-dien-1-yl diphosphate
esculetin = 6,7-dihydroxy-1-benzopyran-2-one = 6,7-dihydroxycoumarin
umbelliferone = 7-hydroxy-1-benzopyran-2-one = 7-hydroxycoumarin

Other name(s):

ClPT1

Systematic name:

geranyl-diphosphate:umbelliferone 8-geranyltransferase

Comments:

The enzyme, characterized from the plant Citrus limon, is specific for geranyl diphosphate as a prenyl donor. It also has low activity with the coumarins 5,7-dihydroxycoumarin and 5-methoxy-7-hydroxycoumarin.

Links to other databases:

BRENDA, EXPASY, KEGG, MetaCyc

References:

Munakata, R., Inoue, T., Koeduka, T., Karamat, F., Olry, A., Sugiyama, A., Takanashi, K., Dugrand, A., Froelicher, Y., Tanaka, R., Uto, Y., Hori, H., Azuma, J., Hehn, A., Bourgaud, F. and Yazaki, K. Molecular cloning and characterization of a geranyl diphosphate-specific aromatic prenyltransferase from lemon. Plant Physiol. 166 (2014) 80–90. [DOI] [PMID: 25077796]

[EC 2.5.1.138 created 2017]

2.5.1.139

Accepted name:

umbelliferone 6-dimethylallyltransferase

Reaction:

prenyl diphosphate + umbelliferone = diphosphate + demethylsuberosin

For diagram of psoralen biosynthesis, click here

Glossary:

demethylsuberosin = 7-hydroxy-6-prenyl-1-benzopyran-2-one
osthenol = 7-hydroxy-8-prenyl-1-benzopyran-2-one

Other name(s):

PcPT; dimethylallyl-diphosphate:umbelliferone 6-dimethylallyltransferase

Systematic name:

prenyl-diphosphate:umbelliferone 6-prenyltransferase

Comments:

The enzyme from parsley (Petroselinum crispum) is specific for umbelliferone and prenyl diphosphate. A minor product is osthenol, which is produced by transfer of the prenyl group to C-8 of umbelliferone.

Links to other databases:

BRENDA, EXPASY, KEGG, MetaCyc

References:

1.	Hamerski, D., Schmitt, D. and Matern, U. Induction of two prenyltransferases for the accumulation of coumarin phytoalexins in elicitor-treated Ammi majus cell suspension cultures. Phytochemistry 29 (1990) 1131–1135. [DOI] [PMID: 1366425]
2.	Karamat, F., Olry, A., Munakata, R., Koeduka, T., Sugiyama, A., Paris, C., Hehn, A., Bourgaud, F. and Yazaki, K. A coumarin-specific prenyltransferase catalyzes the crucial biosynthetic reaction for furanocoumarin formation in parsley. Plant J. 77 (2014) 627–638. [DOI] [PMID: 24354545]

[EC 2.5.1.139 created 2017]

3.1.1.56

Accepted name:

methylumbelliferyl-acetate deacetylase

Reaction:

4-methylumbelliferyl acetate + H₂O = 4-methylumbelliferone + acetate

Other name(s):

esterase D

Systematic name:

4-methylumbelliferyl-acetate acylhydrolase

Comments:

Acts on short-chain acyl esters of 4-methylumbelliferone, but not on naphthyl, indoxyl or thiocholine esters.

Links to other databases:

BRENDA, EXPASY, KEGG, MetaCyc, PDB, CAS registry number: 83380-83-0

References:

1.	Hopkinson, D.A., Mestriner, M.A., Cortner, J. and Harris, H. Esterase D: a new human polymorphism. Ann. Hum. Genet. 37 (1973) 119–137. [DOI] [PMID: 4768551]

[EC 3.1.1.56 created 1986]