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Information on EC 1.14.14.103 - tabersonine 16-hydroxylase
for references in articles please use BRENDA:EC1.14.14.103
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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
1.14.14.103 tabersonine 16-hydroxylase
IUBMB Comments
A cytochrome P-450 (heme-thiolate) protein from the plant Madagascar periwinkle (Catharanthus roseus).
The enzyme appears in viruses and cellular organisms
- 1.14.14.103
- catharanthus
- roseus
- vindoline
- indole
- vinblastine
-
terpenoid
-
catharanthine
- vincristine
-
madagascar
- periwinkle
-
breakpoints
-
aerial
-
monoterpene
- geraniol
-
suspension-cultured
-
lochnericine
-
unbalanced
-
searle
-
seven-step
-
abrasion
- secologanin
-
artemisinic
-
six-step
-
carborundum
- strictosidine
- elicitor
-
10-hydroxylase
-
nonrandom
-
scalable
- synthesis
Reaction Schemes
showSynonyms
tabersonine 16-hydroxylase, cyp71d351, cyp71d12, t16h2, more
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
CYP71D12
EC 1.14.13.73
-
-
formerly
-
oxygenase, tabersonine 16-mono-
-
-
-
-
T16H
tabersonine 16-monooxygenase
T16H
-
-
-
-
tabersonine 16-monooxygenase
-
-
-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
tabersonine + [reduced NADPH-hemoprotein reductase] + O2 = 16-hydroxytabersonine + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
oxidation
-
-
-
-
redox reaction
-
-
-
-
reduction
-
-
-
-
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PATHWAY SOURCE
PATHWAYS
MetaCyc
vindoline, vindorosine and vinblastine biosynthesis
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SYSTEMATIC NAME
IUBMB Comments
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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CAS REGISTRY NUMBER
COMMENTARY
250378-34-8
-
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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
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: -
Products: -
?
2,3-dihydrotabersonine + [reduced NADPH-hemoprotein reductase] + O2
2,3-dihydro-16-hydroxytabersonine + [oxidized NADPH-hemoprotein reductase] + H2O
C0KYN4
Substrates: low activity
Products: -
Products: -
?
tabersonine + NADPH + H+ + O2
16-hydroxytabersonine + NADP+ + H2O
-
Substrates: -
Products: -
Products: -
?
tabersonine + NADPH + H+ + O2
16-hydroxytabersonine + NADP+ + H2O
C0KYN4
Substrates: -
Products: -
Products: -
?
tabersonine + NADPH + H+ + O2
16-hydroxytabersonine + NADP+ + H2O
Substrates: -
Products: -
Products: -
?
tabersonine + NADPH + H+ + O2
16-hydroxytabersonine + NADP+ + H2O
C0KYN4
Substrates: highest activity
Products: -
Products: -
?
tabersonine + NADPH + H+ + O2
16-hydroxytabersonine + NADP+ + H2O
-
Substrates: NADH is less active as substrate
Products: -
Products: -
?
tabersonine + NADPH + H+ + O2
16-hydroxytabersonine + NADP+ + H2O
-
Substrates: first step in vindoline boxynthesis
Products: -
Products: -
?
tabersonine + NADPH + H+ + O2
16-hydroxytabersonine + NADP+ + H2O
Substrates: indole alkaloid synthesis
Products: -
Products: -
?
tabersonine + NADPH + H+ + O2
16-hydroxytabersonine + NADP+ + H2O
-
Substrates: step in monoterpenoid indole alkaloid biosynthesis, biosynthesis of anticancer dimeric alkaloids vinblastine and vincristine, overview
Products: -
Products: -
?
additional information
?
-
-
Substrates: alkaloid and enzymatic profiling of the vindoline biosynthetic pathway, overview
Products: -
Products: -
?
additional information
?
-
-
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: -
Products: -
?
additional information
?
-
C0KYN4
Substrates: no activity with naringenin, tryptamine, secologanin, strictosidine, ajmalicine, vindoline, and catharanthine
Products: -
Products: -
?
additional information
?
-
-
Substrates: no activity with naringenin, tryptamine, secologanin, strictosidine, ajmalicine, vindoline, and catharanthine
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
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: -
Products: -
?
2,3-dihydrotabersonine + [reduced NADPH-hemoprotein reductase] + O2
2,3-dihydro-16-hydroxytabersonine + [oxidized NADPH-hemoprotein reductase] + H2O
C0KYN4
Substrates: low activity
Products: -
Products: -
?
tabersonine + NADPH + H+ + O2
16-hydroxytabersonine + NADP+ + H2O
-
Substrates: -
Products: -
Products: -
?
tabersonine + NADPH + H+ + O2
16-hydroxytabersonine + NADP+ + H2O
C0KYN4
Substrates: -
Products: -
Products: -
?
tabersonine + NADPH + H+ + O2
16-hydroxytabersonine + NADP+ + H2O
C0KYN4
Substrates: highest activity
Products: -
Products: -
?
tabersonine + NADPH + H+ + O2
16-hydroxytabersonine + NADP+ + H2O
-
Substrates: first step in vindoline boxynthesis
Products: -
Products: -
?
tabersonine + NADPH + H+ + O2
16-hydroxytabersonine + NADP+ + H2O
Substrates: indole alkaloid synthesis
Products: -
Products: -
?
tabersonine + NADPH + H+ + O2
16-hydroxytabersonine + NADP+ + H2O
-
Substrates: step in monoterpenoid indole alkaloid biosynthesis, biosynthesis of anticancer dimeric alkaloids vinblastine and vincristine, overview
Products: -
Products: -
?
additional information
?
-
-
Substrates: alkaloid and enzymatic profiling of the vindoline biosynthetic pathway, overview
Products: -
Products: -
?
additional information
?
-
-
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: -
Products: -
?
additional information
?
-
C0KYN4
Substrates: no activity with naringenin, tryptamine, secologanin, strictosidine, ajmalicine, vindoline, and catharanthine
Products: -
Products: -
?
additional information
?
-
-
Substrates: no activity with naringenin, tryptamine, secologanin, strictosidine, ajmalicine, vindoline, and catharanthine
Products: -
Products: -
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
CO
-
concentration dependent competitive inhibition, 77% inhibition at 90%
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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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
50 different flowering cultivars, one low vindoline accumulating cultivar Little Delicata
-
-
brenda
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
C0KYN4
highest expression of isoform T16H2, CYP71D12 in young leaves
brenda
additional information
additional information
C0KYN4
CYP71D12 transcripts are barely detectable or undetectable in roots, internodes, young and mature leaves, and flower buds
brenda
additional information
-
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
-
CYP71D351 transcripts are barely detectable or undetectable in roots, internodes, young and mature leaves, and flower buds
brenda
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
C0KYN4
T16H is anchored to the endoplasmic reticulum as a monomer via a putative 18-residue N-terminal helix
brenda
additional information
additional information
C0KYN4
vindoline biosynthesis pathway enzyme subcellular localization study, overview
-
brenda
additional information
-
vindoline biosynthesis pathway enzyme subcellular localization study, overview
-
brenda
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
metabolism
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
-
the enzyme is involved in biosynthesis of terpenoid indole alkaloids
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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). 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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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
T16H expression analysis in leaves, overview, recombinant expression in Escherichia coli
-
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
artemisinic acid is able to upregulate the transcriptions of tabersonine 16-hydroxylase
-
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
synthesis
-
artemisinic acid can be used as a promising elicitor, especially for the production of therapeutically important indole alkaloids
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
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
EXTERNAL LINKS (specific for EC-Number 1.14.14.103)
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Release 2023.1 (January 2023)
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