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Information on EC 1.14.19.62 - secologanin synthase and Organism(s) Catharanthus roseus and UniProt Accession U5NDT8

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IUBMB Comments
A cytochrome P-450 (heme-thiolate) protein. Secologanin is the precursor of the monoterpenoid indole alkaloids and ipecac alkaloids.
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This record set is specific for:
Catharanthus roseus
UNIPROT: U5NDT8
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Word Map
The taxonomic range for the selected organisms is: Catharanthus roseus
The enzyme appears in selected viruses and cellular organisms
Synonyms
cyp71a1, secologanin synthase, cyp72a1, cytochrome p450 secologanin synthase, more
SYNONYM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
secologanin synthase
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CYP72A1
member of the P450 family CYP72
cytochrome P450 secologanin synthase
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synthase, secologanin
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
loganin + [reduced NADPH-hemoprotein reductase] + O2 = secologanin + [oxidized NADPH-hemoprotein reductase] + 2 H2O
show the reaction diagram
epidermis-specific expression in immature leaves
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
redox reaction
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oxidation
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-
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reduction
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C-C bond cleavage
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SYSTEMATIC NAME
IUBMB Comments
loganin,[reduced NADPH-hemoprotein reductase]:oxygen oxidoreductase (ring-cleaving)
A cytochrome P-450 (heme-thiolate) protein. Secologanin is the precursor of the monoterpenoid indole alkaloids and ipecac alkaloids.
CAS REGISTRY NUMBER
COMMENTARY hide
258339-71-8
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SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
loganin + [reduced NADPH-hemoprotein reductase] + O2
secologanin + [oxidized NADPH-hemoprotein reductase] + 2 H2O
show the reaction diagram
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-
-
?
loganin + [reduced NADPH-hemoprotein reductase] + O2
secologanin + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
additional information
?
-
NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
loganin + [reduced NADPH-hemoprotein reductase] + O2
secologanin + [oxidized NADPH-hemoprotein reductase] + 2 H2O
show the reaction diagram
-
-
-
?
loganin + [reduced NADPH-hemoprotein reductase] + O2
secologanin + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
additional information
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
cytochrome P450
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NADPH-hemoprotein reductase
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cytochrome P450
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CYP71A1
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
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leaf epidermal cells are biosynthetically competent to produce secologanin precursors that are converted via many enzymatic transformations to make 16-methoxytabersonine, which is then transported to cells within Catharanthus leaves to complete the last three or four enzymatic transformations to make vindoline
Manually annotated by BRENDA team
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epidermis-specific expression of SLS
Manually annotated by BRENDA team
additional information
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
an endoplasmic reticulum-anchored enzyme
Manually annotated by BRENDA team
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the enzyme is anchored to the endoplasmic reticulum via a N-teminal helix, thus allowing the production of secologanin on the cytosolic side of the endoplasmic reticulum membrane
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
metabolism
the enzyme is important in the monoterpenoid indole alkaloid (MIA) biosynthesis in Catharanthus roseus, subcellular organization of the central steps of the pathway, overview. The ring-opening reaction of loganin in the biosynthesis of secologanin is catalyzed by the fourth P450 of this pathway, secologanin synthase (SLS, CYP72A1). Both isozymes SLS1 and SLS2 not only catalyze the oxidative ring cleavage of loganin to produce secologanin but also perform the oxidation of secologanin into secoxyloganin. SLS1 and SLS2 constitute the third type of P450 from the seco-iridoid pathway performing more than one catalytic reaction. Additional enzymes might convert secoxyloganin back to secologanin, the subcellular compartmentation of secologanin biosynthesis may also limit secoxyloganin formation in planta. Secoxyloganin is an acidic compound derived from secologanin that is no longer able to be condensed with tryptamine by STR in the vacuole, due to the absence of the aldehyde function. If secoxyloganin formation occurs in vivo, the resulting depletion of the secologanin pool is deleterious for the subsequent synthesis of MIAs
physiological function
secologanin synthases (SLS) are P450 enzymes that catalyze an unusual ring-opening reaction of loganin in the biosynthesis of the monoterpenoid indole alkaloids (MIA) precursor secologanin
malfunction
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mutant DELTAthSLS fusion protein forms punctuated aggregates in the cytosol in close vicinity with plastids
metabolism
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the enzyme catalyzes the last step of the monoterpene secoiridoid pathway
additional information
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION?
SLS_CATRO
527
1
61055
Swiss-Prot
Secretory Pathway (Reliability: 2)
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
gene CYP72C, DNA and amino acid sequence determination and analysis, sequence comparisons, transcriptome analysis, real-time PCR expression analysis
expression of SLS-GFP fusion protein in Catharanthus roseus cells show localization to the endoplasmic reticulum membranes
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
significant upregulation in salicylic acid treatment (foliar application of 0.01 and 0.1 mM salicylic acid). Upregulation can result in a higher production rate of vinblastine and vincristine alkaloids
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
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involved in vindoline biosynthesis
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Irmler, S.; Schroder, G.; St-Pierre, B.; Crouch, N.P.; Hotze, M.; Schmidt, J.; Strack, D.; Matern, U.; Schroder, J.
Indole alkaloid biosynthesis in Catharanthus roseus: new enzyme activities and identification of cytochrome P450 CYP72A1 as secologanin synthase
Plant J.
24
797-804
2000
Catharanthus roseus (Q05047), Catharanthus roseus
Manually annotated by BRENDA team
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
Manually annotated by BRENDA team
Guirimand, G.; Guihur, A.; Ginis, O.; Poutrain, P.; Hericourt, F.; Oudin, A.; Lanoue, A.; St-Pierre, B.; Burlat, V.; Courdavault, V.
The subcellular organization of strictosidine biosynthesis in Catharanthus roseus epidermis highlights several trans-tonoplast translocations of intermediate metabolites
FEBS J.
278
749-763
2011
Catharanthus roseus
Manually annotated by BRENDA team
Duge de Bernonville, T.; Foureau, E.; Parage, C.; Lanoue, A.; Clastre, M.; Londono, M.A.; Oudin, A.; Houille, B.; Papon, N.; Besseau, S.; Glevarec, G.; Atehortua, L.; Giglioli-Guivarch, N.; St-Pierre, B.; De Luca, V.; O'Connor, S.E.; Courdavault, V.
Characterization of a second secologanin synthase isoform producing both secologanin and secoxyloganin allows enhanced de novo assembly of a Catharanthus roseus transcriptome
BMC Genomics
16
619
2015
Catharanthus roseus (U5NDT8), Catharanthus roseus
Manually annotated by BRENDA team
Soltani, N.; Nazarian-Firouzabadi, F.; Shafeinia, A.; Sadr, A.S.; Shirali, M.
The expression of terpenoid indole alkaloid (TIAs) pathway genes in Catharanthus roseus in response to salicylic acid treatment
Mol. Biol. Rep.
47
7009-7016
2020
Catharanthus roseus (U5NDT8), Catharanthus roseus
Manually annotated by BRENDA team