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Information on EC 1.14.14.123 - oryzalexin D synthase
for references in articles please use BRENDA:EC1.14.14.123
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EC Tree 1 Oxidoreductases
1.14 Acting on paired donors, with incorporation or reduction of molecular oxygen
1.14.14 With reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen into the other donor
1.14.14.123 oryzalexin D synthase
IUBMB Comments
A cytochrome P-450 (heme-thiolate) protein. Isolated from Oryza sativa (rice). Oryzalexin D is a phytoalexin.
The expected taxonomic range for this enzyme is: Oryza sativa
Reaction Schemes
showSynonyms
cyp76m8, more
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
CYP76M8
EC 1.14.13.193
-
-
formerly
-
additional information
CYP76M8
-
-
-
-
additional information
see also EC 1.14.14.112, ent-cassa-12,15-diene 11-hydroxylase
additional information
see also EC 1.14.14.112, ent-cassa-12,15-diene 11-hydroxylase
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
ent-sandaracopimaradien-3beta-ol + [reduced NADPH-hemoprotein reductase] + O2 = oryzalexin D + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
-
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PATHWAY SOURCE
PATHWAYS
MetaCyc
oryzalexin D and E biosynthesis
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SYSTEMATIC NAME
IUBMB Comments
ent-sandaracopimaradien-3beta-ol,[reduced NADPH-hemoprotein reductase]:oxygen oxidoreductase (oryzalexin D forming)
A cytochrome P-450 (heme-thiolate) protein. Isolated from Oryza sativa (rice). Oryzalexin D is a phytoalexin.
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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
ent-cassadiene + [reduced NADPH-hemoprotein reductase] + O2
?
-
Substrates: -
Products: -
Products: -
?
ent-isokaurene + [reduced NADPH-hemoprotein reductase] + O2
?
-
Substrates: -
Products: -
Products: -
?
ent-kaurene + [reduced NADPH-hemoprotein reductase] + O2
?
-
Substrates: -
Products: -
Products: -
?
ent-pimaradiene + [reduced NADPH-hemoprotein reductase] + O2
?
-
Substrates: -
Products: -
Products: -
?
ent-sandaracopimaradien-3beta-ol + [reduced NADPH-hemoprotein reductase] + O2
oryzalexin D + [oxidized NADPH-hemoprotein reductase] + H2O
syn-pimaradiene + [reduced NADPH-hemoprotein reductase] + O2
momilactone A + [oxidized NADPH-hemoprotein reductase] + H2O
-
Substrates: -
Products: -
Products: -
?
ent-sandaracopimaradien-3beta-ol + [reduced NADPH-hemoprotein reductase] + O2
oryzalexin D + [oxidized NADPH-hemoprotein reductase] + H2O
-
Substrates: -
Products: -
Products: -
?
ent-sandaracopimaradien-3beta-ol + [reduced NADPH-hemoprotein reductase] + O2
oryzalexin D + [oxidized NADPH-hemoprotein reductase] + H2O
Substrates: -
Products: -
Products: -
?
additional information
?
-
-
Substrates: no reaction with syn-pimaradien-19-oic acid, syn-stemodene, syn-stemarene, or syn-labdatriene
Products: -
Products: -
?
additional information
?
-
Substrates: the enzyme is active with ent-sandaracopimaradiene, ent-pimaradiene, ent-isokaurene, ent-cassadiene, ent-kaurene, and syn-pimaradiene as substrates
Products: -
Products: -
?
additional information
?
-
Substrates: the enzyme is active with ent-sandaracopimaradiene, ent-pimaradiene, ent-isokaurene, ent-cassadiene, ent-kaurene, and syn-pimaradiene as substrates. CYP701A8 can convert syn-pimaradien-19,6 beta-olide to momilactone A, EC 1.1.1.295
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
ent-sandaracopimaradien-3beta-ol + [reduced NADPH-hemoprotein reductase] + O2
oryzalexin D + [oxidized NADPH-hemoprotein reductase] + H2O
ent-sandaracopimaradien-3beta-ol + [reduced NADPH-hemoprotein reductase] + O2
oryzalexin D + [oxidized NADPH-hemoprotein reductase] + H2O
-
Substrates: -
Products: -
Products: -
?
ent-sandaracopimaradien-3beta-ol + [reduced NADPH-hemoprotein reductase] + O2
oryzalexin D + [oxidized NADPH-hemoprotein reductase] + H2O
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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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.007
ent-sandaracopimaradien-3beta-ol
-
pH and temperature not specified in the publication
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.011
ent-sandaracopimaradien-3beta-ol
-
pH and temperature not specified in the publication
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kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
1.6
ent-sandaracopimaradien-3beta-ol
-
pH and temperature not specified in the publication
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
cultivars Thaibonnet and Volano, and cultivars Arborio, Carnaroli, Baldo, S. Andrea, Loto, Vialone Nano, Augusto, Balilla, Nipponbare, Eurosis, and Gange
UniProt
brenda
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
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
malfunction
deletion of the BGC from chromosome 2 (c2BGC), which is associated with phytocassane biosynthesis, but not that from chromosome 4 (c4BGC), which is associated with momilactone biosynthesis, leads to a lesion mimic phenotype. This phenotype is dependent on two closely related genes encoding cytochrome P450 (CYP) monooxygenases, CYP76M7 and CYP76M8, from the c2BGC. Rather than being redundant, CYP76M7 has been associated with the production of phytocassanes, whereas CYP76M8 is associated with momilactone biosynthesis. Intriguingly, the lesion mimic phenotype is not present in a line with both BGCs deleted. Phytocassanes, momilactones and oryzalexin S are no longer detectable in DELTAc2/c4bgc plants, and production of oryzalexins A-F is significantly reduced. Mutants DELTAc2bgc and DELTAc2/c4bgc mutant plants are significantly more susceptible to both strains of Magnaporthe oryzae applied than the wild-type strain Kitaake, although this effect is much more pronounced with Magnaporthe oryzae strain O254 than with strain CA89. By contrast, DELTAc4bgc mutant plants do not exhibit significantly increased susceptibility to either strain of Magnaporte oryzae. DELTAc2bgc and DELTAc2/c4bgc plants are significantly more susceptible to pathogen Xanthomonas oryzae pv. oryzae (Xoo) strain PXO99, with almost a 10fold increase in colony forming units (CFU) relative to the wild-type, while DELTAc4bgc plants instead exhibit a slight but significant decrease in CFU
metabolism
physiological function
additional information
chilling and cold effects on 13 different plant cultivar phenotypes are compared, overview
evolution
directional cross-cluster phytotoxicity, presumably arising from the accumulation of LRD intermediates dependent on the c4BGC in the absence of enzymes CYP76M7 and CYP76M8, highlights their interdependent evolution and the selective pressures driving BGC assembly
evolution
CYP76M8 falls within a phylogenetic clade of the CYP76M subfamily that, in addition to CYP76M5, CYP76M6, and CYP76M7, which also are found in the c2BGC, has members located elsewhere in the rice genome. 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. The presence of CYP76M8 in the other phytocassane BGC indicates interdependent evolution of these two BGCs, highlighting the distinct nature of BGC assembly in plants
metabolism
Oryza sativa is a staple food crop and serves as a model cereal plant. It contains two biosynthetic gene clusters (BGCs) for the production of labdane-related diterpenoids (LRDs), which serve important roles in combating biotic and abiotic stress. Two closely related genes encoding cytochrome P450 (CYP) mono-oxygenases, CYP76M7 and CYP76M8, belong to the BGC from chromosome 2, c2BGC. Enzyme CYP76M8 is associated with momilactone biosynthesis, it plays a less important role in phytocassane biosynthesis. The results reveal directional cross-cluster phytotoxicity, presumably arising from the accumulation of LRD intermediates dependent on the BGC from chromosome 4, c4BGC, in the absence of CYP76M7 and CYP76M8, highlighting their interdependent evolution and the selective pressures driving BGC assembly
metabolism
the momilactone biosynthetic gene cluster (BGC) is not only incomplete, but also fractured by the need for CYP76M8 to act in between steps catalyzed by enzymes from this BGC. The presence of CYP76M8 in the other phytocassane BGC indicates interdependent evolution of these two BGCs, highlighting the distinct nature of BGC assembly in plants. CYP76M7 is primarily responsible for phytocassane production. CYP76M8 acts after CYP99A2 and/or CYP99A3 from the momilactone BGC, with the resulting hemiacetal further oxidized to the eponymous lactone by the OsMS1 and/or OsMS2 also from this BGC
physiological function
genotyping-phenotyping of the enzyme involved in response to low temperatures from the two cultivars Thaibonnet and Volano, analysis of the short-term molecular responses of the two genotypes to low temperatures at two different time-points (referred to as early and late) between those two cultivars, overview. Cultivars Thaibonnet and Volano are cold-sensitive and cold-resistant, respectively
physiological function
enzyme CYP76M8 is associated with momilactone biosynthesis, it plays a less important role in phytocassane biosynthesis. Biosynthetic gene cluster of chromosome 2 (c2BGC)-dependent LRDs act as phytoalexins and phytoanticipins against Xanthomonas oryzae pv. oryzae (Xoo) infection
physiological function
role for cytochrome P450 (CYP) monooxygenase CYP76M8 from the phytocassane BGC. This CYP76M8 acts after the CYP99A2/3 from the momilactone BGC, producing a hemiacetal intermediate that is oxidized to the eponymous lactone by a short-chain alcohol dehydrogenase also from this BGC
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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). Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
construction of CYP76M8 knockout mutants. CRISPR/Cas9 can be applied to simultaneously target multiple genes/loci, i.e. CYP76M8 and related gene CYP76M7. The lesion mimic phenotype depends on both CYP76M7 and CYP76M8, as exhibited by cyp76m7/8 double, but not cyp76m7 or cyp76m8 single, mutant lines. The lesions arise from directional phytotoxicity, presumably from the BGC from chromosome 4 (c4BGC)-dependent labdane-related diterpenoid (LRD) intermediates that accumulate in the absence of the BGC from chromosome 2 (c2BGC), specifically loss of CYP76M7 and CYP76M8. Phytocassanes, momilactones and oryzalexin S are no longer detectable in DELTAc2/c4bgc plants, and production of oryzalexins A-F is significantly reduced. Mutants DELTAc2bgc and DELTAc2/c4bgc mutant plants are significantly more susceptible to both strains of Magnaporthe oryzae applied than the wild-type strain Kitaake, although this effect is much more pronounced with Magnaporthe oryzae strain O254 than with strain CA89. By contrast, DELTAc4bgc mutant plants do not exhibit significantly increased susceptibility to either strain of Magnaporte oryzae. DELTAc2bgc and DELTAc2/c4bgc plants are significantly more susceptible to pathogen Xanthomonas oryzae pv. oryzae (Xoo) strain PXO99, with almost a 10fold increase in colony forming units (CFU) relative to the wild-type, while DELTAc4bgc plants instead exhibit a slight but significant decrease in CFU
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
gene C76M8, genotyping, quantitative real-time PCR enzyme expression analysis
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
gene CYP76M8 (Os02g0569400) is strongly upregulated only in the cold-tolerant genotype Volano at both early and late stage
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Wang, Q.; Hillwig, M.; Okada, K.; Yamazaki, K.; Wu, Y.; Swaminathan, S.; Yamane, H.; Peters, R.
Characterization of CYP76M5-8 indicates metabolic plasticity within a plant biosynthetic gene cluster
J. Biol. Chem.
287
6159-6168
2012
Oryza sativa
brenda
Wu, Y.; Wang, Q.; Hillwig, M.; Peters, R.
Picking sides: Distinct roles for CYP76M6 and CYP76M8 in rice oryzalexin biosynthesis
Biochem. J.
454
209-216
2013
Oryza sativa
brenda
Buti, M.; Pasquariello, M.; Ronga, D.; Milc, J.A.; Pecchioni, N.; Ho, V.T.; Pucciariello, C.; Perata, P.; Francia, E.
Transcriptome profiling of short-term response to chilling stress in tolerant and sensitive Oryza sativa ssp. japonica seedlings
Funct. Integr. Genomics
18
627-644
2018
Oryza sativa Japonica Group (Q6YTF1)
brenda
Li, R.; Zhang, J.; Li, Z.; Peters, R.J.; Yang, B.
Dissecting the labdane-related diterpenoid biosynthetic gene clusters in rice reveals directional cross-cluster phytotoxicity
New Phytol.
233
878-889
2022
Oryza sativa Japonica Group (Q6YTF1)
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 (Q6YTF1)
brenda
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