KEGG   PATHWAY: rn00901
Entry
rn00901                     Pathway                                
Name
Indole alkaloid biosynthesis
Class
Metabolism; Biosynthesis of other secondary metabolites
Pathway map
rn00901  Indole alkaloid biosynthesis
rn00901

Module
M00962  Psilocybin biosynthesis, tryptophan => psilocybin [PATH:rn00901]
M00963  Chanoclavine aldehyde biosynthesis, tryptophan => chanoclavine-I aldehyde [PATH:rn00901]
M00964  Fumigaclavine biosynthesis, chanoclavine-I aldehyde => fumigaclavine C [PATH:rn00901]
M00965  Vinblastine biosynthesis, geissoschizine => vinblastine [PATH:rn00901]
M00979  Ajmaline biosynthesis, geissoschizine => ajmaline [PATH:rn00901]
M00980  Strychnine biosynthesis, geissoschizine => strychnine [PATH:rn00901]
M00981  Geissoschizine biosynthesis, tryptophan => geissoschizine [PATH:rn00901]
Other DBs
GO: 0009709
Reaction
R00685  L-tryptophan decarboxy-lyase
R01657  dimethylallyl-diphosphate:L-tryptophan dimethylallyltransferase
R03230  acetyl-CoA:17-O-deacetylvindoline 17-O-acetyltransferase
R03703  raucaffricine beta-D-glucohydrolase
R03738  3-alpha(S)-strictosidine tryptamine-lyase
R03820  strictosidine beta-D-glucohydrolase
R03860  geissoschizine:NADP+ 4,21-oxidoreductase
R04013  S-adenosyl-L-methionine:16-methoxy-2,3-dihydro-3-hydroxytabersonine N-methyltransferase
R05824  
R05825  polyneuridine aldehyde hydrolase (decarboxylating)
R05826  
R05827  10-deoxysarpagine:NADP+ oxidoreductase
R05828  10-deoxysarpagine,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (10-hydroxylating)
R05829  (19E)-geissoschizine:[oxidized NADPH---hemoprotein reductase] oxidoreductase (polyneuridine aldehyde forming)
R05844  
R05845  
R05846  
R05847  
R05848  
R05849  
R05855  tabersonine,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (16-hydroxylating)
R05857  desacetoxyvindoline,2-oxoglutarate:oxygen oxidoreductase (4b-hydroxylating)
R05858  
R05859  
R05860  
R05866  
R05867  
R05868  
R05869  
R05870  
R05871  
R05872  
R05873  
R05874  
R05876  acyl-CoA:16-epivellosimine O-acetyltransferase (cyclizing)
R05877  vinorine,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (21alpha-hydroxylating)
R05878  (2R)-1,2-dihydrovomilenine:NADP+ oxidoreductase
R05879  17-O-acetylnorajmaline:NADP+ oxidoreductase
R05880  17-O-acetylnorajmaline O-acetylhydrolase
R05881  S-adenosyl-L-methionine:norajmaline N-methyltransferase
R05882  UDP-glucose:vomilenine 21-O-beta-D-glucosyltransferase
R05885  S-adenosyl-L-methionine:16-hydroxytabersonine 16-O-methyltransferase
R05886  
R07513  17-O-acetylajmaline O-acetylhydrolase
R08480  ATP:psilocin 4-phosphotransferase
R08481  
R08482  
R08483  
R08484  
R08485  
R08486  
R10128  chanoclavine-I:NAD+ oxidoreductase
R10163  festuclavine:NAD+ oxidoreductase
R10166  S-adenosyl-L-methionine:4-(3-methylbut-2-enyl)-L-tryptophan N-methyltransferase
R10200  acetyl-CoA:fumigaclavine B O-acetyltransferase
R10201  dimethylallyl-diphosphate:fumigaclavine A dimethylallyltransferase
R10229  agroclavine:NADP+ oxidoreductase
R11777  (3R)-3-hydroxy-16-methoxy-2,3-dihydrotabersonine:acceptor oxidoreductase
R11802  (3R)-3-hydroxy-2,3-dihydrotabersonine:acceptor oxidoreductase
R11810  16-methoxytabersonine,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (3-hydroxylating)
R11811  tabersonine,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (3-hydroxylating)
R11912  tryptamine,hydrogen-donor:oxygen oxidoreductase (4-hydroxylating)
R11932  4-hydroxy-L-tryptophan carboxy-lyase
R11933  ATP:4-hydroxytryptamine 4-phosphotransferase
R11935  S-adenosyl-L-methionine:norbaeocystin N-methyltransferase
R11936  S-adenosyl-L-methionine:baeocystin N-methyltransferase
R12090  chanoclavine-I aldehyde:NAD+ oxidoreductase
R12091  
R12093  
R12094  
R12104  
R12138  
R12142  
R12282  
R12827  
R12828  
R12829  
R12830  
R13329  
R13330  17-dehydropreakuammicine hydrolase (decarboxylating)
R13331  
R13332  (19E)-cura-2(16),19-dien-17-al,[NADPH---hemoprotein reductase]:oxygen oxidoreductase (18-hydroxylating)
R13333  17,18-epoxy-17-hydroxycur-19-ene:NADP+ oxidoreductase
R13334  malonyl-CoA:17,18-epoxy-17-hydroxycur-19-ene N-malonyltransferase
R13335  acetyl-CoA:(19E)-17,18-epoxy-17-hydroxycur-19-ene N-acetyltransferase
R13336  
R13337  
R13338  strychnine,[NADPH---hemoprotein reductase]:oxygen oxidoreductase (10-hydroxylating)
R13339  S-adenosyl-L-methionine:hydroxystrychnine O-methyltransferase
R13340  beta-colubrine,[NADPH---hemoprotein reductase]:oxygen oxidoreductase (11-hydroxylating)
R13341  
R13342  
R13343  acetyl-CoA:stemmadenine O-acetyltransferase
R13344  stemmadenine acetate:oxygen oxidoreductase
R13345  precondylocarpine acetate:NADP+ oxidoreductase
R13346  dehydrosecodine cyclase (tabersonine-forming)
R13347  dehydrosecodine cyclase (catharanthine-forming)
R13348  17-dehydrostemmadenine:NADP+ 3(4)-oxidoreductase
R13349  stemmadenine:NADP+ 17-oxidoreductase
R13356  S-adenosyl-L-methionine:ajmaline N-methyltransferase
R13362  acetyl-CoA:rhazimol O-acetyltransferase
R13376  
R13377  rhazimol:NADP+ oxidoreductase (rhazimol-forming)
R13378  geissoschizine,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (rhazimal forming)
R13382  
Compound
C00031  D-Glucose
C00078  L-Tryptophan
C00398  Tryptamine
C01091  Deacetylvindoline
C01626  Vindoline
C01761  Vomilenine
C01852  Secologanin
C02074  Raucaffricine
C02151  (19E)-Geissoschizine
C02673  Desacetoxyvindoline
C03309  Strictosidine aglycone
C03470  3-alpha(S)-Strictosidine
C03677  4,21-Dehydrogeissoschizine
C04290  4-(3-Methylbut-2-enyl)-L-tryptophan
C04578  16-Methoxy-2,3-dihydro-3-hydroxytabersonine
C06068  Elymoclavine
C06522  Strychnine
C06535  Physostigmine
C06536  Harmaline
C06538  Harmine
C06542  Ajmaline
C07201  Vinblastine
C07204  Vincristine
C07541  Lysergic acid
C07544  Ergotamine
C07576  Psilocybin
C08312  Psilocin
C09023  Agroclavine
C09024  Ajmalicine
C09025  Akuammicine
C09028  Alstonine
C09084  Brucine
C09089  Calligonine
C09107  Catharanthine
C09131  Chanoclavine-I
C09209  Harman
C09239  Sarpagine
C09241  Serpentine
C09243  Tetrahydroharmine
C09244  Tabersonine
C11632  Polyneuridine aldehyde
C11633  16-Epivellosimine
C11634  Vellosimine
C11635  10-Deoxysarpagine
C11641  3',4'-Anhydrovinblastine
C11642  19-Hydroxytabersonine
C11643  16-Hydroxytabersonine
C11675  16-Methoxytabersonine
C11676  Lochnericine
C11677  Horhammericine
C11678  Dialdehyde
C11679  4,21-Dehydrocorynantheine aldehyde
C11680  Cathenamine
C11681  19-epi-Cathenamine
C11682  Tetrahydroalstonine
C11683  19-epi-Ajmalicine
C11691  Stemmadenine
C11783  Minovincinine
C11784  Echitovenine
C11807  Vinorine
C11808  1,2-Dihydrovomilenine
C11809  17-O-Acetylnorajmaline
C11810  Norajmaline
C11812  Lochnerinine
C15985  17-O-Acetylajmaline
C20379  Chanoclavine-I aldehyde
C20408  Festuclavine
C20409  6,8-Dimethyl-6,7-didehydroergoline
C20410  4-Dimethylallyl-L-abrine
C20436  Fumigaclavine A
C20437  Fumigaclavine B
C20438  Fumigaclavine C
C20457  6,8-Dimethyl-6,7,8,9-tetradehydroergoline
C21678  (3R)-3-Hydroxy-16-methoxy-1,2-didehydro-2,3-dihydrotabersonine
C21682  (3R)-3-Hydroxy-2,3-dihydrotabersonine
C21683  (3R)-3-Hydroxy-1,2-didehydro-2,3-dihydrotabersonine
C21762  4-Hydroxytryptamine
C21777  4-Hydroxy-L-tryptophan
C21778  Norbaeocystin
C21779  Baeocystin
C21897  Dihydrochanoclavine-I aldehyde
C22432  Paspalic acid
C22893  Rhazimal
C22922  17-Dehydropreakuammicine
C22923  Norfluorocurarine
C22924  18-Hydroxynorfluorocurarine
C22925  Wieland-Gumlich aldehyde
C22926  Diaboline
C22927  Prestrychnine
C22928  Isostrychnine
C22929  10-Hydroxystrychnine
C22930  beta-Colubrine
C22931  11-Demethylbrucine
C22933  Stemmadenine acetate
C22934  Precondylocarpine acetate
C22935  Dihydroprecondylocarpine acetate
C22936  3,17-Didehydrostemmadenine
C22937  17-Dehydrostemmadenine
C22945  4-Methylajmaline
C22950  Rhazimol
C22951  Akuammiline
C22960  Dehydrosecodine
C22961  17-Dehydropreakuammicine hydrate
Reference
PMID:9622525
  Authors
Rijhwani SK, Shanks JV.
  Title
Effect of elicitor dosage and exposure time on biosynthesis of indole alkaloids by Catharanthus roseus hairy root cultures.
  Journal
Biotechnol Prog 14:442-9 (1998)
DOI:10.1021/bp980029v
Reference
PMID:4698228
  Authors
Madyastha KM, Guarnaccia R, Baxter C, Coscia CJ.
  Title
S-Adenosyl-L-methionine: loganic acid methyltransferase. A carboxyl-alkylating enzyme from Vinca rosea.
  Journal
J Biol Chem 248:2497-501 (1973)
Reference
PMID:510306
  Authors
Treimer JF, Zenk MH.
  Title
Purification and properties of strictosidine synthase, the key enzyme in indole alkaloid formation.
  Journal
Eur J Biochem 101:225-33 (1979)
DOI:10.1111/j.1432-1033.1979.tb04235.x
Reference
PMID:10652285
  Authors
Geerlings A, Ibanez MM, Memelink J, van Der Heijden R, Verpoorte R.
  Title
Molecular cloning and analysis of strictosidine beta-D-glucosidase, an enzyme in terpenoid indole alkaloid biosynthesis in Catharanthus roseus.
  Journal
J Biol Chem 275:3051-6 (2000)
DOI:10.1074/jbc.275.5.3051
Reference
PMID:11128
  Authors
Stockigt J, Treimer J, Zenk MH.
  Title
Synthesis of ajmalicine and related indole alkaloids by cell free extracts of Catharanthus roseus cell suspension cultures.
  Journal
FEBS Lett 70:267-70 (1976)
DOI:10.1016/0014-5793(76)80772-7
Reference
PMID:12228585
  Authors
St-Pierre B, De Luca V.
  Title
A Cytochrome P-450 Monooxygenase Catalyzes the First Step in the Conversion of Tabersonine to Vindoline in Catharanthus roseus.
  Journal
Plant Physiol 109:131-139 (1995)
DOI:10.1104/pp.109.1.131
Reference
PMID:10481044
  Authors
Schroder G, Unterbusch E, Kaltenbach M, Schmidt J, Strack D, De Luca V, Schroder J.
  Title
Light-induced cytochrome P450-dependent enzyme in indole alkaloid biosynthesis: tabersonine 16-hydroxylase.
  Journal
FEBS Lett 458:97-102 (1999)
DOI:10.1016/S0014-5793(99)01138-2
Reference
PMID:9654153
  Authors
Sottomayor M, Lopez-Serrano M, DiCosmo F, Ros Barcelo A.
  Title
Purification and characterization of alpha-3',4'-anhydrovinblastine synthase (peroxidase-like) from Catharanthus roseus (L.) G. Don.
  Journal
FEBS Lett 428:299-303 (1998)
DOI:10.1016/S0014-5793(98)00551-1
Reference
PMID:1368411
  Authors
Furuya T, Sakamoto K, Iida K, Asada Y, Yoshikawa T, Sakai S, Aimi N.
  Title
Biotransformation of tabersonine in cell suspension cultures of Catharanthus roseus.
  Journal
Phytochemistry 31:3065-8 (1992)
DOI:10.1016/0031-9422(92)83447-7
Reference
PMID:11154328
  Authors
Laflamme P, St-Pierre B, De Luca V.
  Title
Molecular and biochemical analysis of a madagascar periwinkle root-specific minovincinine-19-hydroxy-o-acetyltransferase.
  Journal
Plant Physiol 125:189-98 (2001)
DOI:10.1104/pp.125.1.189
Reference
PMID:12150812
  Authors
Jain S, Sinha A, Bhakuni DS.
  Title
The biosynthesis of beta-carboline and quinolizidine alkaloids of Alangium lamarckii.
  Journal
Phytochemistry 60:853-9 (2002)
DOI:10.1016/S0031-9422(02)00057-2
Reference
PMID:28763571
  Authors
Fricke J, Blei F, Hoffmeister D
  Title
Enzymatic Synthesis of Psilocybin.
  Journal
Angew Chem Int Ed Engl 56:12352-12355 (2017)
DOI:10.1002/anie.201705489
Related
pathway
rn00400  Phenylalanine, tyrosine and tryptophan biosynthesis
rn00902  Monoterpenoid biosynthesis
KO pathway
ko00901   

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