cinnamate 4-hydroxylase

桂皮酸-4-水酸化酵素、桂皮酸-4-ヒドロキシラーゼ

関

trans-cinnamate 4-monooxygenase

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/05/08 11:03:39」(JST)

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trans-cinnamate 4-monooxygenase
Identifiers
EC number	1.14.13.11
CAS number	9077-75-2
Databases
IntEnz	IntEnz view
BRENDA	BRENDA entry
ExPASy	NiceZyme view
KEGG	KEGG entry
MetaCyc	metabolic pathway
PRIAM	profile
PDB structures	RCSB PDB PDBe PDBsum
Gene Ontology	AmiGO / EGO
Search PMC articles PubMed articles NCBI proteins

In enzymology, a trans-cinnamate 4-monooxygenase (EC 1.14.13.11) is an enzyme that catalyzes the chemical reaction

trans-cinnamate + NADPH + H⁺ + O₂ 4-hydroxycinnamate + NADP⁺ + H₂O

The 4 substrates of this enzyme are trans-cinnamate, NADPH, H⁺, and O₂, whereas its 3 products are 4-hydroxycinnamate, NADP⁺, and H₂O. This enzyme participates in phenylalanine metabolism and phenylpropanoid biosynthesis. It employs one cofactor, heme.

This enzyme belongs to the family of oxidoreductases, specifically those acting on paired donors, with O₂ as oxidant and incorporation or reduction of oxygen. The oxygen incorporated need not be derived from O2 with NADH or NADPH as one donor, and incorporation of one atom o oxygen into the other donor.

Nomenclature

The systematic name of this enzyme class is trans-cinnamate,NADPH:oxygen oxidoreductase (4-hydroxylating). Other names in common use include:

• cinnamic acid 4-hydroxylase,
• oxygenase, cinnamate 4-mono-,
• CA4H,
• cytochrome P450 cinnamate 4-hydroxylase,
• cinnamate 4-hydroxylase,
• cinnamate 4-monooxygenase,
• cinnamate hydroxylase,
• cinnamic 4-hydroxylase,
• cinnamic acid 4-monooxygenase,
• cinnamic acid p-hydroxylase,
• hydroxylase, cinnamate 4-,
• t-cinnamic acid hydroxylase,
• trans-cinnamate 4-hydroxylase, and
• trans-cinnamic acid 4-hydroxylase.

References

Further reading

• Potts JR, Weklych R, Conn EE, Rowell J (1974). "The 4-hydroxylation of cinnamic acid by sorghum microsomes and the requirement for cytochrome P-450". J. Biol. Chem. 249 (16): 5019–26. PMID 4153152. 
• Russell DW, Conn EE (1967). "The cinnamic acid 4-hydroxylase of pea seedlings". Arch. Biochem. Biophys. 122 (1): 256–8. doi:10.1016/0003-9861(67)90150-6. PMID 4383827. 
• Petersen M (May 2003). "Cinnamic acid 4-hydroxylase from cell cultures of the hornwort Anthoceros agrestis". Planta 217 (1): 96–101. doi:10.1007/s00425-002-0960-9. PMID 12721853. 

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English Journal

• Isolation and characterization of isochorismate synthase and cinnamate 4-hydroxylase during salinity stress, wounding, and salicylic acid treatment in Carthamus tinctorius.

• Sadeghi M, Dehghan S, Fischer R, Wenzel U, Vilcinskas A, Reza Kavousi H, Rahnamaeian M.AbstractSalicylic acid (SA) is a prominent signaling molecule during biotic and abiotic stresses in plants, which is biosynthesized via cinnamate and isochorismate pathways. Cinnamate 4-hydroxylase (C4H) and isochorismate synthase (ICS) are the main enzymes in phenylpropanoid and isochorismate pathways, respectively. To investigate the actual roles of these genes in resistance mechanism to environmental stresses, here, the coding sequences of these 2 enzymes in safflower (Carthamus tinctorius), as an oilseed industrial medicinal plant, were partially isolated and their expression profiles during salinity stress, wounding, and salicylic acid treatment were monitored. As a result, safflower ICS (CtICS) and C4H (CtC4H) were induced in early time points after wounding (3?6 h). Upon salinity stress, CtICS and CtC4H were highly expressed for the periods of 6?24 h and 3?6 h after treatment, respectively. It seems evident that ICS expression level is SA concentration dependent as if plant treatment with 1 mM SA could induce ICS much stronger than that of 0.1 mM, while C4H is less likely to be so. Based on phylogenetic analysis, safflower ICS has maximum similarity to its ortholog in Vitis vinifera up to 69%, while C4H shows the highest similarity to its ortholog in Echinacea angustifolia up to 96%. Overall, the isolated genes of CtICS and CtC4H in safflower could be recruited in plant breeding programs for salinity tolerance as well as for pathogen resistance.
• Plant signaling & behavior.Plant Signal Behav.2013 Dec 5;8(11). pii: e27335. [Epub ahead of print]
• Salicylic acid (SA) is a prominent signaling molecule during biotic and abiotic stresses in plants, which is biosynthesized via cinnamate and isochorismate pathways. Cinnamate 4-hydroxylase (C4H) and isochorismate synthase (ICS) are the main enzymes in phenylpropanoid and isochorismate pathways, res
• PMID 24309561

• Enhanced lignin monomer production caused by cinnamic Acid and its hydroxylated derivatives inhibits soybean root growth.

• Lima RB, Salvador VH, Dos Santos WD, Bubna GA, Finger-Teixeira A, Soares AR, Marchiosi R, Ferrarese Mde L, Ferrarese-Filho O.SourceLaboratory of Plant Biochemistry, University of Maringá, Maringá, Paraná, Brazil.
• PloS one.PLoS One.2013 Dec 3;8(12):e80542. doi: 10.1371/journal.pone.0080542.
• Cinnamic acid and its hydroxylated derivatives (p-coumaric, caffeic, ferulic and sinapic acids) are known allelochemicals that affect the seed germination and root growth of many plant species. Recent studies have indicated that the reduction of root growth by these allelochemicals is associated wit
• PMID 24312480

• Substrates and enzyme activities related to biotransformation of resveratrol from phenylalanine by Alternaria sp. MG1.

• Zhang J, Shi J, Liu Y.SourceCollege of Food Science and Engineering, Northwest A&F University, 28 Xinong Road, Yangling, Shaanxi Province, 712100, China.
• Applied microbiology and biotechnology.Appl Microbiol Biotechnol.2013 Dec;97(23):9941-54. doi: 10.1007/s00253-013-5212-3. Epub 2013 Sep 26.
• To identify the substrates and enzymes related to resveratrol biosynthesis in Alternaria sp. MG1, different substrates were used to produce resveratrol, and their influence on resveratrol production was analyzed using high performance liquid chromatography (HPLC). Formation of resveratrol and relate
• PMID 24068334

Japanese Journal

• Molecular Cloning and Characterization of Genes Involved in Rosmarinic Acid Biosynthesis from <i>Prunella vulgaris</i>

• Biological and Pharmaceutical Bulletin 37(7), 1221-1227, 2014
• NAID 130003390995

• Distinct Roles of Cinnamate 4-hydroxylase Genes in Populus

• Plant and cell physiology 47(7), 905-914, 2006-07-01
• NAID 10018185506

• 4-アミノ-5-アリール-2,3-ジヒドロ-3H-1,2,4-トリアゾール-3-チオン類のトランス-ケイ皮酸4-水酸化酵素阻害活性

• Journal of pesticide science 30(4), 406-408, 2005-11-20
• NAID 110002323364

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★リンクテーブル★

リンク元	「桂皮酸-4-水酸化酵素」「trans-cinnamate 4-monooxygenase」「桂皮酸-4-ヒドロキシラーゼ」
関連記事	「cinnamate」

「桂皮酸-4-水酸化酵素」

　　[★]

英

cinnamate 4-hydroxylase

関

トランス桂皮酸-4-モノオキシゲナーゼ、桂皮酸-4-ヒドロキシラーゼ

「trans-cinnamate 4-monooxygenase」

　　[★]

トランス桂皮酸-4-モノオキシゲナーゼ

関

cinnamate 4-hydroxylase

「桂皮酸-4-ヒドロキシラーゼ」

　　[★]

英

cinnamate 4-hydroxylase

関

桂皮酸-4-水酸化酵素

「cinnamate」

　　[★]

桂皮酸エステル、桂皮酸塩、桂皮酸

関

cinnamic acid