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Information on EC 1.1.1.295 - momilactone-A synthase
for references in articles please use BRENDA:EC1.1.1.295
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EC Tree 1 Oxidoreductases
1.1 Acting on the CH-OH group of donors
1.1.1 With NAD+ or NADP+ as acceptor
1.1.1.295 momilactone-A synthase
IUBMB Comments
The rice phytoalexin momilactone A is a diterpenoid secondary metabolite that is involved in the defense mechanism of the plant. Momilactone A is produced in response to attack by a pathogen through the perception of elicitor signal molecules such as chitin oligosaccharide, or after exposure to UV irradiation. The enzyme, which catalyses the last step in the biosynthesis of momilactone A, can use both NAD+ and NADP+ but activity is higher with NAD+ .
The enzyme appears in viruses and cellular organisms
- 1.1.1.295
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solid-state
-
spin
-
magic
-
cross-polarization
-
magic-angle
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spin-lattice
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quadrupolar
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o-alkyl
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magic-angle-spinning
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redor
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hetcor
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variable-temperature
Reaction Schemes
showSynonyms
cpmas, momilactone a synthase, osmas, osmas2, ak103462 protein, more
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
momilactone A synthase
additional information
cf. EC 1.14.14.68 and EC 1.14.14.70
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
3beta-hydroxy-9beta-pimara-7,15-diene-19,6beta-olide + NAD(P)+ = momilactone A + NAD(P)H + H+
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-
-
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PATHWAY SOURCE
PATHWAYS
MetaCyc
momilactone A biosynthesis
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SYSTEMATIC NAME
IUBMB Comments
3beta-hydroxy-9beta-pimara-7,15-diene-19,6beta-olide:NAD(P)+ oxidoreductase
The rice phytoalexin momilactone A is a diterpenoid secondary metabolite that is involved in the defense mechanism of the plant. Momilactone A is produced in response to attack by a pathogen through the perception of elicitor signal molecules such as chitin oligosaccharide, or after exposure to UV irradiation. The enzyme, which catalyses the last step in the biosynthesis of momilactone A, can use both NAD+ and NADP+ but activity is higher with NAD+ [1].
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CAS REGISTRY NUMBER
COMMENTARY
458569-32-9
-
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
2alpha-hydroxy-ent-cassadiene + NAD+
? + NADH + H+
Substrates: -
Products: -
Products: -
?
3beta-hydroxy-9beta-pimara-7,15-diene-19,6beta-olide + NAD(P)+
momilactone A + NAD(P)H + H+
3beta-hydroxy-9beta-pimara-7,15-diene-19,6beta-olide + NAD+
momilactone A + NADH
-
Substrates: -
Products: -
Products: -
?
3beta-hydroxy-9beta-pimara-7,15-diene-19,6beta-olide + NADP+
momilactone A + NADPH
-
Substrates: reaction with NADP+ is 70% of the activity with NAD+
Products: -
Products: -
?
3beta-hydroxy-9beta-pimara-7,15-diene-19,6beta-olide + NADP+
momilactone A + NADPH + H+
Substrates: -
Products: -
Products: -
?
oryzalexin D + NAD+
oryzalexin A + NADH + H+
Substrates: -
Products: oxidation of the 7beta-hydroxyl group of oryzalexin D
Products: oxidation of the 7beta-hydroxyl group of oryzalexin D
?
3beta-hydroxy-9beta-pimara-7,15-diene-19,6beta-olide + NAD(P)+
momilactone A + NAD(P)H + H+
Substrates: -
Products: -
Products: -
?
3beta-hydroxy-9beta-pimara-7,15-diene-19,6beta-olide + NAD(P)+
momilactone A + NAD(P)H + H+
-
Substrates: -
Products: -
Products: -
?
3beta-hydroxy-9beta-pimara-7,15-diene-19,6beta-olide + NAD(P)+
momilactone A + NAD(P)H + H+
Substrates: -
Products: -
Products: -
?
3beta-hydroxy-9beta-pimara-7,15-diene-19,6beta-olide + NAD+
momilactone A + NADH + H+
Substrates: -
Products: -
Products: -
?
3beta-hydroxy-9beta-pimara-7,15-diene-19,6beta-olide + NAD+
momilactone A + NADH + H+
-
Substrates: -
Products: -
Products: -
?
3beta-hydroxy-9beta-pimara-7,15-diene-19,6beta-olide + NAD+
momilactone A + NADH + H+
Substrates: -
Products: -
Products: -
?
3beta-hydroxy-9beta-pimara-7,15-diene-19,6beta-olide + NAD+
momilactone A + NADH + H+
Substrates: -
Products: -
Products: -
?
additional information
?
-
Substrates: identity of the momilactone A reaction product is validated by GC-MS analysis
Products: -
Products: -
?
additional information
?
-
Substrates: besides the 3-hydroxylation of ent-sandaracopimara-814,15-diene and 9beta-pimara-7,15-diene (EC 1.14.14.70 and EC 1.14.14.68, respectively), enzyme CYP701A8 can further react beyond initial production of the C3beta-hydroxy derivative to produce the characteristic C3-oxo group of momilactone A. CYP701A8 can synthesize 3beta,6beta-dihydroxy-syn-pimaradiene and convert syn-pimaradien-19,6beta-olide to momilactone A
Products: -
Products: -
?
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
3beta-hydroxy-9beta-pimara-7,15-diene-19,6beta-olide + NAD(P)+
momilactone A + NAD(P)H + H+
3beta-hydroxy-9beta-pimara-7,15-diene-19,6beta-olide + NADP+
momilactone A + NADPH + H+
Substrates: -
Products: -
Products: -
?
3beta-hydroxy-9beta-pimara-7,15-diene-19,6beta-olide + NAD(P)+
momilactone A + NAD(P)H + H+
Substrates: -
Products: -
Products: -
?
3beta-hydroxy-9beta-pimara-7,15-diene-19,6beta-olide + NAD(P)+
momilactone A + NAD(P)H + H+
-
Substrates: -
Products: -
Products: -
?
3beta-hydroxy-9beta-pimara-7,15-diene-19,6beta-olide + NAD(P)+
momilactone A + NAD(P)H + H+
Substrates: -
Products: -
Products: -
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
cytochrome P450
the enzyme is a cytochrome P450 monooxygenase
-
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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DISEASE
TITLE OF PUBLICATION
LINK TO PUBMED
Muscle Cramp
Determination of the conformation and stability of simple homopolypeptides using solid-state NMR.
Muscle Cramp
Probing hydrogen bond networks in half-sandwich Ru(II) building blocks by a combined 1H DQ CRAMPS solid-state NMR, XRPD, and DFT approach.
Muscle Cramp
Solid-state NMR spectroscopy and first-principles calculations: a powerful combination of tools for the investigation of polymorphism of indomethacin.
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.2
3beta-hydroxy-9beta-pimara-7,15-diene-19,6beta-olide
pH 8.0, 30°C
0.9
3beta-hydroxy-9beta-pimara-7,15-diene-19,6beta-olide
pH 8.0, 30°C
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.08
3beta-hydroxy-9beta-pimara-7,15-diene-19,6beta-olide
pH 8.0, 30°C
0.4
3beta-hydroxy-9beta-pimara-7,15-diene-19,6beta-olide
pH 8.0, 30°C
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kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.09
3beta-hydroxy-9beta-pimara-7,15-diene-19,6beta-olide
pH 8.0, 30°C
2
3beta-hydroxy-9beta-pimara-7,15-diene-19,6beta-olide
pH 8.0, 30°C
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
6 - 10
-
pH 6.0: about 50% of maximal activity, pH 10.0: about 60% of maximal activity
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
36 - 72
-
36°C: about 60% of maximal activity, 72°C: about 60% of maximal activity
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
Highest Expressing Human Cell Lines
Cell Line LinksPlease wait a moment until the data is sorted. This message will disappear when the data is sorted.
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
evolution
metabolism
physiological function
isoform MS2 more efficiently catalyzes the final oxidation to produce momilactone A than isoform MS1
evolution
molecular architecture of the momilactone biosynthetic genes and evolutionary relationships with other momilactone-producing plants. Both cultivated and wild grass species of Oryza and Echinochloa crus-galli (barnyard grass) produce momilactones using a biosynthetic gene cluster (BGC) in their genomes. The bryophyte Calohypnum plumiforme (formerly Hypnum plumaeforme) also produces momilactones, and the bifunctional diterpene cyclase gene CpDTC1/HpDTC1, which is responsible for the production of the diterpene framework. While the gene cluster in Calohypnum plumiforme is functionally similar to that in rice and barnyard grass, it is likely a product of convergent evolution. Echinochloa crus-galli (barnyard grass) has been shown to possess one copy of the momilactone gene cluster in its genome. Thus, all of the momilactone-producing higher plants reported thus far appear to have a family-conserved BGC in their genomes. Evolution of momilactone gene clusters in plants, overview
evolution
-
molecular architecture of the momilactone biosynthetic genes and evolutionary relationships with other momilactone-producing plants. Both cultivated and wild grass species of Oryza and Echinochloa crus-galli (barnyard grass) produce momilactones using a biosynthetic gene cluster (BGC) in their genomes. The bryophyte Calohypnum plumiforme (formerly Hypnum plumaeforme) also produces momilactones, and the bifunctional diterpene cyclase gene CpDTC1/HpDTC1, which is responsible for the production of the diterpene framework. While the gene cluster in Calohypnum plumiforme is functionally similar to that in rice and barnyard grass, it is likely a product of convergent evolution. Echinochloa crus-galli (barnyard grass) has been shown to possess one copy of the momilactone gene cluster in its genome. Thus, all of the momilactone-producing higher plants reported thus far appear to have a family-conserved BGC in their genomes. Evolution of momilactone gene clusters in plants, overview
evolution
molecular architecture of the momilactone biosynthetic genes in the moss genome and their evolutionary relationships with other momilactone-producing plants. Both cultivated and wild grass species of Oryza and Echinochloa crus-galli (barnyard grass) produce momilactones using a biosynthetic gene cluster (BGC) in their genomes. The bryophyte Calohypnum plumiforme (formerly Hypnum plumaeforme) also produces momilactones, and the bifunctional diterpene cyclase gene CpDTC1/HpDTC1, which is responsible for the production of the diterpene framework. While the gene cluster in Calohypnum plumiforme is functionally similar to that in rice and barnyard grass, it is likely a product of convergent evolution. Echinochloa crus-galli (barnyard grass) has been shown to possess one copy of the momilactone gene cluster in its genome. Thus, all of the momilactone-producing higher plants reported thus far appear to have a family-conserved BGC in their genomes. Evolution of momilactone gene clusters in plants, overview
evolution
interdependent evolution of biosynthetic gene clusters for momilactone production in rice. Plants are limited to vertical gene transmission, implying that their biosynthetic gene clusters (BGCs) may exhibit distinct inheritance patterns. Rice (Oryza sativa) contains two unlinked BGCs involved in diterpenoid phytoalexin metabolism, with one clearly required for momilactone biosynthesis, while the other is associated with production of phytocassanes, interdependent evolution of these two BGCs, highlighting the distinct nature of BGC assembly in plants. CYP701A8 belongs to the c4BGC gene cluster. Expression of all the genes from the momilactone c4BGC and several from the c2BGC, including all those from the CYP76M subfamily, as well as CYP701A8 and the closely related CYP701A9, are examined
metabolism
early regulation of genes putatively related to nematode damage-associated molecular pattern recognition (e.g. wall-associated receptor kinases), signalling (nucleotide-binding, leucine-rich repeat (NLRs)), pathogenesis-related (PR) genes (PR1, PR10a), defence-related genes (NB-ARC domain-containing genes), as well as a large number of genes involved in secondary metabolites including diterpenoid biosynthesis (CPS2, OsKSL4, OsKSL10, Oscyp71Z2, oryzalexin synthase, and momilactone A synthase) is observed in rice Meloidogyne graminicola-resistant mutant line-9. After the nematode juveniles penetrate the roots of line-9, early recognition of invading nematodes triggers plant immune responses mediated by phytoalexins, and other defence proteins such as PR proteins inhibit nematode growth and reproduction. Mechanisms underlying plant-nematode resistance in rice, overview. Momilactone A is one of several phytoalexins also such as oryzalexin D, oryzalexin E, and phytocassane being part of the secondary metabolite biosynthesis pathways activated in defense. The enzyme is involved in diterpenoid biosynthesis
metabolism
the enzyme is involved in momilactone A biosynthesis, proposed momilactone A biosynthetic pathway, overview
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UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). A0A6F8PFR7_9BRYO
277
0
28758
TrEMBL
Mitochondrion (Reliability: 1)
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PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
successful momilactone biosynthetic pathway reconstitution in Nicotiana benthamiana expressing the biosynthetic gene cluster (BGC), transient coexpression of CpMAS with CpDTC1/HpDTC1, CpCYP970A14, and CpCYP964A1 genes encoding diterpene cyclase 1, pimaradiene oxidase 1, and pimaradiene oxidase 2, respectively. The potential enzymatic activity of momilactone A synthesis from 3OH-syn-pimaradienolide exists endogenously in Nicotiana benthamiana leaves, based on in vitro assays with crude protein and in planta feeding assays. Eventually, coexpression of CpMAS with other clustered genes increases the production of momilactone A, and in planta conversion of 3OH-syn-pimaradienolide to momilactone A is apparently enhanced by CpMAS expression in Nicotiana benthamiana as compared to that in the vector control plant
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PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
recombinant His-tagged CpMAS enzyme from Escherichia coli by nickel affinity chromatography
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
gene CpMAS, DNA and amino acid sequence determination and analysis, sequence comparisons and phylogenetic analysis, the CpDTC1/HpDTC1 gene and the dehydrogenase momilactone A synthase gene is tandemly arranged and inductively transcribed following stress exposure, recombinant expression of His-tagged CpMAS enzyme in Escherichia coli. Transient coexpression of CpMAS with CpDTC1/HpDTC1, CpCYP970A14, and CpCYP964A1 genes encoding diterpene cyclase 1, pimaradiene oxidase 1, and pimaradiene oxidase 2, respectively in Nicotiana benthamiana
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
early regulation of genes putatively related to rice root-knot nematode (RRKN) Meloidogyne graminicola damage-associated molecular pattern recognition (e.g. wall-associated receptor kinases), signalling (nucleotide-binding, leucine-rich repeat (NLRs)), pathogenesis-related (PR) genes (PR1, PR10a), defence-related genes (NB-ARC domain-containing genes), as well as a large number of genes involved in secondary metabolites including diterpenoid biosynthesis (CPS2, OsKSL4, OsKSL10, Oscyp71Z2, oryzalexin synthase, and momilactone A synthase) is observed in rice Meloidogyne graminicola-resistant mutant line-9. After the nematode juveniles penetrate the roots of line-9, early recognition of invading nematodes triggers plant immune responses mediated by phytoalexins, and other defence proteins such as PR proteins inhibit nematode growth and reproduction. Mechanisms underlying plant-nematode resistance in rice, overview
the CpDTC1/HpDTC1 gene and the dehydrogenase momilactone A synthase gene is tandemly arranged and inductively transcribed following stress exposure
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Atawong, A.; Hasegawa, M.; Kodama, O.
Biosynthesis of rice phytoalexin: enzymatic conversion of 3beta-hydroxy-9beta-pimara-7,15-dien-19,6beta-olide to momilactone A
Biosci. Biotechnol. Biochem.
66
566-570
2002
Oryza sativa
brenda
Shimura, K.; Okada, A.; Okada, K.; Jikumaru, Y.; Ko, K.W.; Toyomasu, T.; Sassa, T.; Hasegawa, M.; Kodama, O.; Shibuya, N.; Koga, J.; Nojiri, H.; Yamane, H.
Identification of a biosynthetic gene cluster in rice for momilactones
J. Biol. Chem.
282
34013-34018
2007
Oryza sativa (Q7FAE1), Oryza sativa
brenda
Kitaoka, N.; Wu, Y.; Zi, J.; Peters, R.J.
Investigating inducible short-chain alcohol dehydrogenases/reductases clarifies rice oryzalexin biosynthesis
Plant J.
88
271-279
2016
Oryza sativa (Q7FAE1), Oryza sativa (Q7FAE2), Oryza sativa
brenda
Dash, M.; Somvanshi, V.S.; Budhwar, R.; Godwin, J.; Shukla, R.N.; Rao, U.
A rice root-knot nematode Meloidogyne graminicola-resistant mutant rice line shows early expression of plant-defence genes
Planta
253
108
2021
Oryza sativa Japonica Group (Q7FAE2)
brenda
Mao, L.; Kawaide, H.; Higuchi, T.; Chen, M.; Miyamoto, K.; Hirata, Y.; Kimura, H.; Miyazaki, S.; Teruya, M.; Fujiwara, K.; Tomita, K.; Yamane, H.; Hayashi, K.I.; Nojiri, H.; Jia, L.; Qiu, J.; Ye, C.; Timko, M.P.; Fan, L.; Okada, K.
Genomic evidence for convergent evolution of gene clusters for momilactone biosynthesis in land plants
Proc. Natl. Acad. Sci. USA
117
12472-12480
2020
Calohypnum plumiforme (A0A6F8PFR7), Echinochloa crus-galli, Oryza sativa Japonica Group (Q7FAE2)
brenda
Kitaoka, N.; Zhang, J.; Oyagbenro, R.K.; Brown, B.; Wu, Y.; Yang, B.; Li, Z.; Peters, R.J.
Interdependent evolution of biosynthetic gene clusters for momilactone production in rice
Plant Cell
33
290-305
2021
Oryza sativa Japonica Group (Q7FAE1)
brenda
EXTERNAL LINKS (specific for EC-Number 1.1.1.295)
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