The reaction occurs in the opposite direction to that shown above. The enzyme participates in the menthol-biosynthesis pathway of Mentha plants. (+)-Pulegone, (+)-cis-isopulegone and (-)-menthone are not substrates. The enzyme has a preference for NADPH as the reductant, with NADH being a poor substitute . The enzyme is highly regioselective for the reduction of the endocyclic 1,2-double bond, and is stereoselective, producing only the 1R-configured product. It is a member of the short-chain dehydrogenase/reductase superfamily.
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SYSTEMATIC NAME
IUBMB Comments
(+)-cis-isopulegone:NADP+ oxidoreductase
The reaction occurs in the opposite direction to that shown above. The enzyme participates in the menthol-biosynthesis pathway of Mentha plants. (+)-Pulegone, (+)-cis-isopulegone and (-)-menthone are not substrates. The enzyme has a preference for NADPH as the reductant, with NADH being a poor substitute [2]. The enzyme is highly regioselective for the reduction of the endocyclic 1,2-double bond, and is stereoselective, producing only the 1R-configured product. It is a member of the short-chain dehydrogenase/reductase superfamily.
the soluble NADPH-dependent, endocyclic double-bond reductase reduces (-)-isopiperitenone to (+)-cis-isopulegone, pathways of monoterpene biosynthesis, overview
the soluble NADPH-dependent, endocyclic double-bond reductase reduces (-)-isopiperitenone to (+)-cis-isopulegone, pathways of monoterpene biosynthesis, overview
compound analysis by GS-MS. 3-methyl-6-(prop-1-en-2-yl)cyclohex-2-en-1-one is a poor substrate for enzyme mutant E238Y. Substrate specificity of wild-type and mutant enzymes and ligand binding structure analysis, overview
the soluble NADPH-dependent, endocyclic double-bond reductase reduces (-)-isopiperitenone to (+)-cis-isopulegone, pathways of monoterpene biosynthesis, overview
the soluble NADPH-dependent, endocyclic double-bond reductase reduces (-)-isopiperitenone to (+)-cis-isopulegone, pathways of monoterpene biosynthesis, overview
compound analysis by GS-MS. 3-methyl-6-(prop-1-en-2-yl)cyclohex-2-en-1-one is a poor substrate for enzyme mutant E238Y. Substrate specificity of wild-type and mutant enzymes and ligand binding structure analysis, overview
endophyte isolated from rhizomes of Picrorhiza kurroa, the ITS1-5.8S-ITS2 ribosomal gene sequence shows highest similarity of 99% with Diaporthe phaseolorum followed by 98% with Phomopsis liquidambari, strain PR4 is taxonomically placed under the species, Diaporthe phaseolorum
endophyte isolated from rhizomes of Picrorhiza kurroa, the ITS1-5.8S-ITS2 ribosomal gene sequence shows highest similarity of 99% with Diaporthe phaseolorum followed by 98% with Phomopsis liquidambari, strain PR4 is taxonomically placed under the species, Diaporthe phaseolorum
the enzyme belongs to the short-chain dehydrogenases/reductases SDR superfamily. A sequence alignment of the three ketoreductases MMR, MNMR, and salutaridine reductase (45-49% homology to Mentha enzymes) from Papaver somniferum with Mentha pipertita enzyme IPR shows each enzyme contains typical SDR-like motifs, such as those involved in central beta-sheet stabilization, and a TGxxxGhG motif
the enzyme products are important for intra- and extracellular pathogen defense, the cell extract is biologicaly active against several pathogenic organisms, overview
the enzyme products are important for intra- and extracellular pathogen defense, the cell extract is biologicaly active against several pathogenic organisms, overview
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CRYSTALLIZATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
enzyme IPR in apoform and in complex with NADP+, alkene 3-methyl-6-(prop-1-en-2-yl)cyclohex-2-en-1-one, and beta-cyclocitral, X-ray diffraction structure determination and analysis using using SalR crystal structure, PDB ID 3O26, at 1.2 and 1.7 A resolution, respectively, via molecular replacement, PDB ID 5LCX
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
DNA and amino acid sequence determination and analysis, functional expression of wild-type enzyme in Escherichia coli strain BL21(DE3), expression of a mutant cloning artifact that has a seven residue deletion at the C-terminus and bores an additional 33 vector-derived residues
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
penconazole and drought stresses alter the essential oil composition of the plant, the amount of (+)-cis-isopulegone is about 2fold increased. Penconazole and drought stress upregulates the iPR enzyme expression
Ringer, K.L.; McConkey, M.E.; Davis, E.M.; Rushing, G.W.; Croteau, R.
Monoterpene double-bond reductases of the (-)-menthol biosynthetic pathway: isolation and characterization of cDNAs encoding (-)-isopiperitenone reductase and (+)-pulegone reductase of peppermint
Qadri, M.; Deshidi, R.; Shah, B.A.; Bindu, K.; Vishwakarma, R.A.; Riyaz-Ul-Hassan, S.
An endophyte of Picrorhiza kurroa Royle ex. Benth, producing menthol, phenylethyl alcohol and 3-hydroxypropionic acid, and other volatile organic compounds