KEGG   PATHWAY: ko00901
Entry
ko00901                     Pathway                                
Name
Indole alkaloid biosynthesis
Class
Metabolism; Biosynthesis of other secondary metabolites
Pathway map
ko00901  Indole alkaloid biosynthesis
ko00901

Module
M00962  Psilocybin biosynthesis, tryptophan => psilocybin [PATH:ko00901]
M00963  Chanoclavine aldehyde biosynthesis, tryptophan => chanoclavine-I aldehyde [PATH:ko00901]
M00964  Fumigaclavine biosynthesis, chanoclavine-I aldehyde => fumigaclavine C [PATH:ko00901]
M00965  Vinblastine biosynthesis, geissoschizine => vinblastine [PATH:ko00901]
M00979  Ajmaline biosynthesis, geissoschizine => ajmaline [PATH:ko00901]
M00980  Strychnine biosynthesis, geissoschizine => strychnine [PATH:ko00901]
M00981  Geissoschizine biosynthesis, tryptophan => geissoschizine [PATH:ko00901]
Other DBs
GO: 0009709
Orthology
K01593  DDC, TDC; aromatic-L-amino-acid/L-tryptophan decarboxylase [EC:4.1.1.28 4.1.1.105]
K01757  STR1; strictosidine synthase [EC:3.5.99.13]
K08233  PNAE; polyneuridine-aldehyde esterase [EC:3.1.1.78]
K12693  SGR1; strictosidine beta-D-glucosidase [EC:3.2.1.105]
K12694  E2.3.1.160; vinorine synthase [EC:2.3.1.160]
K12695  RG; raucaffricine beta-D-glucosidase / vomilenine glucosyltransferase [EC:3.2.1.125 2.4.1.219]
K12696  CYP71D12; tabersonine 16-hydroxylase [EC:1.14.14.103]
K12697  D4H; deacetoxyvindoline 4-hydroxylase [EC:1.14.11.20]
K12698  DAT; deacetylvindoline O-acetyltransferase [EC:2.3.1.107]
K12699  MAT; minovincinine 19-hydroxy-O-acetyltransferase
K14130  FGAPT2; tryptophan 4-dimethylallyltransferase [EC:2.5.1.34]
K14135  FGAPT1; fumigaclavine A dimethylallyltransferase [EC:2.5.1.100]
K17746  ChaDH; chanoclavine-I dehydrogenase [EC:1.1.1.332]
K18884  FGAMT; 4-dimethylallyltryptophan N-methyltransferase [EC:2.1.1.261]
K19182  FGAOX3; chanoclavine-I aldehyde reductase [EC:1.3.1.100]
K19183  FGAFS; festuclavine dehydrogenase [EC:1.5.1.44]
K19184  FGAAT; fumigaclavine B O-acetyltransferase [EC:2.3.1.205]
K21026  AAE; acetylajmaline esterase [EC:3.1.1.80]
K21819  EASG; agroclavine dehydrogenase [EC:1.5.1.46]
K21895  16OMT; tabersonine 16-O-methyltransferase [EC:2.1.1.94]
K21896  NMT; 3-hydroxy-16-methoxy-2,3-dihydrotabersonine N-methyltransferase [EC:2.1.1.99]
K22323  T3R; 3-hydroxy-1,2-didehydro-2,3-dihydrotabersonine reductase [EC:1.1.99.41]
K22326  CYP5437; vinorine hydroxylase [EC:1.14.14.104]
K22365  CYP71D1; tabersonine 3-oxygenase [EC:1.14.14.50]
K22433  PSID; L-tryptophan decarboxylase [EC:4.1.1.105]
K22434  PSIH; tryptamine 4-monooxygenase [EC:1.14.99.59]
K22435  PSIK; 4-hydroxytryptamine kinase [EC:2.7.1.222]
K22436  PSIM; psilocybin synthase [EC:2.1.1.345]
K23493  GS; geissoschizine synthase
K23494  CYP71AY1; alstonine synthase
K25463  CLOA; cytochrome P450 monooxygenase CloA
K27776  SBE2; polyneuridine aldehyde synthase
K27777  VR; vomilenine reductase
K27778  DHVR, RR4; 1,2-dihydrovomilenine 19,20-reductase
K27779  NNMT; norajmaline N-methyltransferase
K27780  GO; (19E)-geissoschizine oxidase
K27781  NS; dehydropreakuammicine esterase
K27782  NO; norfluorocurarine 18-hydroxylase
K27783  WS; 18-hydroxynorfluorocurarine reductase
K27784  AT; 17,18-epoxy-17-hydroxycur-19-ene N-malonyltransferase
K27785  AT; (19E)-17,18-epoxy-17-hydroxycur-19-ene N-acetyltransferase
K27786  10H; strychnine 10-hydroxylase
K27787  OMT; hydroxystrychnine O-methyltransferase
K27788  11H; beta-colubrine 11-hydroxylase
K27789  REDOX1; 3,17-didehydrostemmadenine reductase
K27790  REDOX2; 17-dehydrostemmadenine reductase
K27791  SAT; stemmadenine O-acetyltransferase
K27792  PAS; precondylocarpine acetate synthase
K27793  DPAS; dihydroprecondylocarpine acetate synthase
K27794  CS; catharanthine synthase
K27795  TS; tabersonine synthase
K27796  PRX1; peroxidase PRX1
K27839  AKS1; akuammiline synthase 1
K27840  AKS2; akuammiline synthase 2
K27844  ANMT; ajmaline N-methyltransferase
K27859  RHS; rhazimal synthase
K27860  RHR; rhazimal reductase
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
ko00400  Phenylalanine, tyrosine and tryptophan biosynthesis
ko00902  Monoterpenoid biosynthesis

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