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1.14.14.161

Accepted name:

nepetalactol monooxygenase

Reaction:

(+)-cis,trans-nepetalactol + 3 [reduced NADPH—hemoprotein reductase] + 3 O₂ = 7-deoxyloganetate + 3 [oxidized NADPH—hemoprotein reductase] + 4 H₂O (overall reaction)
(1a) (+)-cis,trans-nepetalactol + [reduced NADPH—hemoprotein reductase] + O₂ = 7-deoxyloganetic alcohol + [oxidized NADPH—hemoprotein reductase] + H₂O
(1b) 7-deoxyloganetic alcohol + [reduced NADPH—hemoprotein reductase] + O₂ = iridotrial + [oxidized NADPH—hemoprotein reductase] + 2 H₂O
(1c) iridotrial + [reduced NADPH—hemoprotein reductase] + O₂ = 7-deoxyloganetate + [oxidized NADPH—hemoprotein reductase] + H₂O

For diagram of gibberellin A₁₂ biosynthesis, click here

Glossary:

(+)-cis,trans-nepetalactol = (4aS,7S,7aR)-4,7-dimethyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-1-ol
7-deoxyloganetate = (1S,4aS,7S,7aR)-1-hydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate

Other name(s):

CYP76A26 (gene name); iridoid oxidase (misleading)

Systematic name:

(+)-cis,trans-nepetalactol,[reduced NADPH—hemoprotein reductase]:oxygen oxidoreductase (hydroxylating)

Comments:

The enzyme, characterized from the plant Catharanthus roseus, is a cytochrome P-450 (heme thiolate) protein. It catalyses three successive reactions in the pathway leading to biosynthesis of monoterpenoid indole alkaloids.

Links to other databases:

BRENDA, EXPASY, KEGG, MetaCyc

References:

Miettinen, K., Dong, L., Navrot, N., Schneider, T., Burlat, V., Pollier, J., Woittiez, L., van der Krol, S., Lugan, R., Ilc, T., Verpoorte, R., Oksman-Caldentey, K.M., Martinoia, E., Bouwmeester, H., Goossens, A., Memelink, J. and Werck-Reichhart, D. The seco-iridoid pathway from Catharanthus roseus. Nat. Commun. 5:3606 (2014). [PMID: 24710322]

[EC 1.14.14.161 created 2018]

2.4.1.323

Accepted name:

7-deoxyloganetic acid glucosyltransferase

Reaction:

UDP-α-D-glucose + 7-deoxyloganetate = UDP + 7-deoxyloganate

For diagram of secologanin biosynthesis, click here

Other name(s):

UGT8

Systematic name:

UDP-α-D-glucose:7-deoxyloganetate O-D-glucosyltransferase

Comments:

Isolated from the plant Catharanthus roseus (Madagascar periwinkle). Involved in loganin and secologanin biosynthesis. Does not react with 7-deoxyloganetin. cf. EC 2.4.1.324 7-deoxyloganetin glucosyltransferase.

Links to other databases:

BRENDA, EXPASY, KEGG, MetaCyc

References:

1.	Asada, K., Salim, V., Masada-Atsumi, S., Edmunds, E., Nagatoshi, M., Terasaka, K., Mizukami, H. and De Luca, V. A 7-deoxyloganetic acid glucosyltransferase contributes a key step in secologanin biosynthesis in madagascar periwinkle. Plant Cell 25 (2013) 4123–4134. [DOI] [PMID: 24104568]

[EC 2.4.1.323 created 2014]

2.4.1.324

Accepted name:

7-deoxyloganetin glucosyltransferase

Reaction:

UDP-α-D-glucose + 7-deoxyloganetin = UDP + 7-deoxyloganin

For diagram of secologanin biosynthesis, click here

Other name(s):

UDPglucose:iridoid glucosyltransferase; UGT6; UGT85A24

Systematic name:

UDP-α-D-glucose:7-deoxyloganetin O-D-glucosyltransferase

Comments:

Isolated from the plants Catharanthus roseus (Madagascar periwinkle) and Gardenia jasminoides (cape jasmine). With Gardenia it also acts on genipin. Involved in loganin and secologanin biosynthesis. Does not react with 7-deoxyloganetate. cf. EC 2.4.1.323 7-deoxyloganetic acid glucosyltransferase.

Links to other databases:

BRENDA, EXPASY, KEGG, MetaCyc

References:

1.	Nagatoshi, M., Terasaka, K., Nagatsu, A. and Mizukami, H. Iridoid-specific glucosyltransferase from Gardenia jasminoides. J. Biol. Chem. 286 (2011) 32866–32874. [DOI] [PMID: 21799001]
2.	Asada, K., Salim, V., Masada-Atsumi, S., Edmunds, E., Nagatoshi, M., Terasaka, K., Mizukami, H. and De Luca, V. A 7-deoxyloganetic acid glucosyltransferase contributes a key step in secologanin biosynthesis in madagascar periwinkle. Plant Cell 25 (2013) 4123–4134. [DOI] [PMID: 24104568]

[EC 2.4.1.324 created 2014]