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IUBMB Comments A cytochrome P -450 (heme-thiolate) protein from the plant Madagascar periwinkle (Catharanthus roseus ).
The enzyme appears in viruses and cellular organisms
Synonyms tabersonine 16-hydroxylase, cyp71d351, cyp71d12, t16h2, more
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CYP71D351
C0KYN4
isoform T16H1
EC 1.14.13.73
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formerly
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oxygenase, tabersonine 16-mono-
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tabersonine 16-hydroxylase
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tabersonine 16-monooxygenase
CYP71D12
C0KYN4
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CYP71D12
C0KYN4
isoform T16H2
T16H
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tabersonine 16-monooxygenase
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tabersonine 16-monooxygenase
C0KYN4
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tabersonine + [reduced NADPH-hemoprotein reductase] + O2 = 16-hydroxytabersonine + [oxidized NADPH-hemoprotein reductase] + H2O
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MetaCyc
vindoline, vindorosine and vinblastine biosynthesis
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tabersonine,[reduced NADPH-hemoprotein reductase]:oxygen oxidoreductase (16-hydroxylating)
A cytochrome P-450 (heme-thiolate) protein from the plant Madagascar periwinkle (Catharanthus roseus).
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2,3-dihydro-3-hydroxytabersonine + [reduced NADPH-hemoprotein reductase] + O2
2,3-dihydro-3,16-dihydroxytabersonine + [oxidized NADPH-hemoprotein reductase] + H2O
C0KYN4
Substrates: low activity Products: -
?
2,3-dihydrotabersonine + [reduced NADPH-hemoprotein reductase] + O2
2,3-dihydro-16-hydroxytabersonine + [oxidized NADPH-hemoprotein reductase] + H2O
C0KYN4
Substrates: low activity Products: -
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tabersonine + NADPH + H+ + O2
16-hydroxytabersonine + NADP+ + H2O
additional information
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tabersonine + NADPH + H+ + O2
16-hydroxytabersonine + NADP+ + H2O
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Substrates: - Products: -
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tabersonine + NADPH + H+ + O2
16-hydroxytabersonine + NADP+ + H2O
C0KYN4
Substrates: - Products: -
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tabersonine + NADPH + H+ + O2
16-hydroxytabersonine + NADP+ + H2O
Substrates: - Products: -
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tabersonine + NADPH + H+ + O2
16-hydroxytabersonine + NADP+ + H2O
C0KYN4
Substrates: highest activity Products: -
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tabersonine + NADPH + H+ + O2
16-hydroxytabersonine + NADP+ + H2O
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Substrates: NADH is less active as substrate Products: -
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tabersonine + NADPH + H+ + O2
16-hydroxytabersonine + NADP+ + H2O
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Substrates: first step in vindoline boxynthesis Products: -
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tabersonine + NADPH + H+ + O2
16-hydroxytabersonine + NADP+ + H2O
Substrates: indole alkaloid synthesis Products: -
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tabersonine + NADPH + H+ + O2
16-hydroxytabersonine + NADP+ + H2O
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Substrates: step in monoterpenoid indole alkaloid biosynthesis, biosynthesis of anticancer dimeric alkaloids vinblastine and vincristine, overview Products: -
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additional information
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Substrates: alkaloid and enzymatic profiling of the vindoline biosynthetic pathway, overview Products: -
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additional information
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Substrates: the enzyme is involved in biosynthesis of precursors in the vindoline pathway in Catharanthus roseus leaf epidermal cells, biosynthesis of anticancer dimeric alkaloids vinblastine and vincristine, overview Products: -
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additional information
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C0KYN4
Substrates: no activity with naringenin, tryptamine, secologanin, strictosidine, ajmalicine, vindoline, and catharanthine Products: -
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additional information
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Substrates: no activity with naringenin, tryptamine, secologanin, strictosidine, ajmalicine, vindoline, and catharanthine Products: -
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2,3-dihydro-3-hydroxytabersonine + [reduced NADPH-hemoprotein reductase] + O2
2,3-dihydro-3,16-dihydroxytabersonine + [oxidized NADPH-hemoprotein reductase] + H2O
C0KYN4
Substrates: low activity Products: -
?
2,3-dihydrotabersonine + [reduced NADPH-hemoprotein reductase] + O2
2,3-dihydro-16-hydroxytabersonine + [oxidized NADPH-hemoprotein reductase] + H2O
C0KYN4
Substrates: low activity Products: -
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tabersonine + NADPH + H+ + O2
16-hydroxytabersonine + NADP+ + H2O
additional information
?
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tabersonine + NADPH + H+ + O2
16-hydroxytabersonine + NADP+ + H2O
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Substrates: - Products: -
?
tabersonine + NADPH + H+ + O2
16-hydroxytabersonine + NADP+ + H2O
C0KYN4
Substrates: - Products: -
?
tabersonine + NADPH + H+ + O2
16-hydroxytabersonine + NADP+ + H2O
C0KYN4
Substrates: highest activity Products: -
?
tabersonine + NADPH + H+ + O2
16-hydroxytabersonine + NADP+ + H2O
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Substrates: first step in vindoline boxynthesis Products: -
?
tabersonine + NADPH + H+ + O2
16-hydroxytabersonine + NADP+ + H2O
Substrates: indole alkaloid synthesis Products: -
?
tabersonine + NADPH + H+ + O2
16-hydroxytabersonine + NADP+ + H2O
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Substrates: step in monoterpenoid indole alkaloid biosynthesis, biosynthesis of anticancer dimeric alkaloids vinblastine and vincristine, overview Products: -
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additional information
?
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Substrates: alkaloid and enzymatic profiling of the vindoline biosynthetic pathway, overview Products: -
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additional information
?
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Substrates: the enzyme is involved in biosynthesis of precursors in the vindoline pathway in Catharanthus roseus leaf epidermal cells, biosynthesis of anticancer dimeric alkaloids vinblastine and vincristine, overview Products: -
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additional information
?
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C0KYN4
Substrates: no activity with naringenin, tryptamine, secologanin, strictosidine, ajmalicine, vindoline, and catharanthine Products: -
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additional information
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Substrates: no activity with naringenin, tryptamine, secologanin, strictosidine, ajmalicine, vindoline, and catharanthine Products: -
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cytochrome P450
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cytochrome P450
C0KYN4
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clotrimazole
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50% inhibition at 0.05 mM
CO
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concentration dependent competitive inhibition, 77% inhibition at 90%
cytochrome c
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50% inhibition at 0.001 mM
miconazole
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50% inhibition at 0.3 mM
tabersonine
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inhibition above 0.03 mM
tricliphane
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50% inhibition at 0.5 mM
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0.00007 - 0.011
tabersonine
0.00007
tabersonine
C0KYN4
isoform T16H2, at pH 8.0 and 30°C
0.00035
tabersonine
C0KYN4
isoform T16H1, at pH 8.0 and 30°C
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8
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assay at
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brenda
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C0KYN4
UniProt
brenda
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brenda
50 different flowering cultivars, one low vindoline accumulating cultivar Little Delicata
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brenda
CYP71D12; cultivar Pacifica Pink
C0KYN4
UniProt
brenda
line CP3a
Uniprot
brenda
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brenda
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from leaf
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predominantly
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C0KYN4
isoform T16H1, CYP71D351
brenda
C0KYN4
highest expression of isoform T16H2, CYP71D12 in young leaves
brenda
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brenda
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brenda
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brenda
C0KYN4
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brenda
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young
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quantitative expression analysis in leaves
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suspension-cultured cell from leaf
brenda
additional information
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localization study
brenda
additional information
C0KYN4
CYP71D12 transcripts are barely detectable or undetectable in roots, internodes, young and mature leaves, and flower buds
brenda
additional information
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CYP71D12 transcripts are barely detectable or undetectable in roots, internodes, young and mature leaves, and flower buds
brenda
additional information
C0KYN4
CYP71D351 transcripts are barely detectable or undetectable in roots, internodes, young and mature leaves, and flower buds
brenda
additional information
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CYP71D351 transcripts are barely detectable or undetectable in roots, internodes, young and mature leaves, and flower buds
brenda
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C0KYN4
T16H is anchored to the endoplasmic reticulum as a monomer via a putative 18-residue N-terminal helix
brenda
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brenda
C0KYN4
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brenda
C0KYN4
CYP71D351 (isoform T16H2)
brenda
additional information
C0KYN4
vindoline biosynthesis pathway enzyme subcellular localization study, overview
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brenda
additional information
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vindoline biosynthesis pathway enzyme subcellular localization study, overview
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brenda
Highest Expressing Human Cell Lines
Filter by:
Cell Line Links
Gene Links
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metabolism
C0KYN4
the enzyme catalyzes the first step in the biosynthesis of vindoline, which constitutes the main terpenoid indole alkaloid accumulated in leaves of Catharanthus roseus, spatial organization of the vindoline biosynthetic pathway, overview. Absence of metabolic channeling in the vindoline biosynthetic pathway. Importance of inter- and intracellular translocations of intermediates during the vindoline biosynthesis and potential regulatory role, overview
metabolism
C0KYN4
CYP71D12 (isoform T16H2) plays a role in the biosynthesis of vindoline in flowers
metabolism
C0KYN4
CYP71D351 (isoform T16H2) has a major role in the biosynthesis of vindoline in leaves
metabolism
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the enzyme is involved in biosynthesis of terpenoid indole alkaloids
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C71DC_CATRO
506
0
58079
Swiss-Prot
Secretory Pathway (Reliability: 2 )
C71DZ_CATRO
512
0
58483
Swiss-Prot
Secretory Pathway (Reliability: 1 )
A0A2P6QG65_ROSCH
171
0
19053
TrEMBL
other Location (Reliability: 3 )
A0A2P6QG69_ROSCH
161
0
18377
TrEMBL
other Location (Reliability: 3 )
G7IUY6_MEDTR
509
1
57615
TrEMBL
Secretory Pathway (Reliability: 2 )
A0A2P6QD93_ROSCH
81
0
9535
TrEMBL
Mitochondrion (Reliability: 4 )
A0A396HZK9_MEDTR
59
0
6709
TrEMBL
Secretory Pathway (Reliability: 3 )
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DNA and amino acid sequence determination and analysis
C0KYN4
expressed in Saccharomyces cerevisiae WAT11 cells
C0KYN4
T16H expression analysis in leaves, overview, recombinant expression in Escherichia coli
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artemisinic acid is able to upregulate the transcriptions of tabersonine 16-hydroxylase
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synthesis
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artemisinic acid can be used as a promising elicitor, especially for the production of therapeutically important indole alkaloids
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Schroder, G.; Unterbusch, E.; Kaltenbach, M.; Schmidt, J.; Strack, D.; De Luca, V.; Schroder, J.
Light-induced cytochrome P450-dependent enzyme in indole alkaloid biosynthesis: tabersonine 16-hydroxylase
FEBS Lett.
458
97-102
1999
Catharanthus roseus (P98183), Catharanthus roseus
brenda
St-Pierre, B.; De Luca, V.
A cytochrome P-450 monooxygenase catalyzes the first step in the conversion of tabersonine to vindoline in Catharanthus roseus
Plant Physiol.
109
131-139
1995
Catharanthus roseus
brenda
Murata, J.; De Luca, V.
localization of tabersonine 16-hydroxylase and 16-OH tabersonine-16-O-methyltransferase to leaf epidermal cells defines them as a major site of precursor biosynthesis in the vindoline pathway in Catharanthus roseus
Plant J.
44
581-594
2005
Catharanthus roseus
brenda
Magnotta, M.; Murata, J.; Chen, J.; De Luca, V.
Identification of a low vindoline accumulating cultivar of Catharanthus roseus (L.) G. Don by alkaloid and enzymatic profiling
Phytochemistry
67
1758-1764
2006
Catharanthus roseus
brenda
Guirimand, G.; Guihur, A.; Poutrain, P.; Hericourt, F.; Mahroug, S.; St-Pierre, B.; Burlat, V.; Courdavault, V.
Spatial organization of the vindoline biosynthetic pathway in Catharanthus roseus
J. Plant Physiol.
168
549-557
2010
Catharanthus roseus (C0KYN4), Catharanthus roseus
brenda
Besseau, S.; Kellner, F.; Lanoue, A.; Thamm, A.M.; Salim, V.; Schneider, B.; Geu-Flores, F.; Hoefer, R.; Guirimand, G.; Guihur, A.; Oudin, A.; Glevarec, G.; Foureau, E.; Papon, N.; Clastre, M.; Giglioli-Guivarch, N.; St-Pierre, B.; Werck-Reichhart, D.; Burlat, V.; De Luca, V.; OConnor, S.E.; Cou, C.o.u.r.
A pair of tabersonine 16-hydroxylases initiates the synthesis of vindoline in an organ-dependent manner in Catharanthus roseus
Plant Physiol.
163
1792-1803
2013
Catharanthus roseus (C0KYN4), Catharanthus roseus
brenda
Liu, J.; Zhu, J.; Tang, L.; Wen, W.; Lv, S.; Yu, R.
Enhancement of vindoline and vinblastine production in suspension-cultured cells of Catharanthus roseus by artemisinic acid elicitation
World J. Microbiol. Biotechnol.
30
175-180
2014
Catharanthus roseus
brenda
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