ENTRY       zma00950                    Pathway
NAME        Isoquinoline alkaloid biosynthesis - Zea mays (maize)
DESCRIPTION Isoquinoline alkaloids are tyrosine-derived plant alkaloids with an isoquinoline skeleton. Among them benzylisoquinoline alkaloids form an important group with potent pharmacological activity, including analgesic compounds of morphine and codeine, and anti-infective agents of berberine, palmatine, and magnoflorine. Biosynthesis of isoquinoline alkaloids proceeds via decarboxylation of tyrosine or DOPA to yield dopamine, which together with 4-hydroxyphenylacetaldehyde, an aldehyde derived from tyrosine, is converted to reticuline, an important precursor of various benzylisoquinoline alkaloids.
CLASS       Metabolism; Biosynthesis of other secondary metabolites
PATHWAY_MAP zma00950  Isoquinoline alkaloid biosynthesis
DBLINKS     GO: 0033075
ORGANISM    Zea mays (maize) [GN:zma]
GENE        100273311  uncharacterized protein LOC100273311 [KO:K14454] [EC:2.6.1.1]
            100274119  aspartate aminotransferase [KO:K14455] [EC:2.6.1.1]
            100282625  aspartate aminotransferase [KO:K00811] [EC:2.6.1.1]
            100276531  uncharacterized protein LOC100276531 [KO:K15849] [EC:2.6.1.1 2.6.1.78 2.6.1.79]
            100274472  uncharacterized protein LOC100274472 [KO:K15849] [EC:2.6.1.1 2.6.1.78 2.6.1.79]
            100279205  uncharacterized protein LOC100279205 [KO:K00815] [EC:2.6.1.5]
            100279999  uncharacterized LOC100279999 [KO:K00815] [EC:2.6.1.5]
            100191816  uncharacterized protein LOC100191816 [KO:K00815] [EC:2.6.1.5]
            103651121  polyphenol oxidase, chloroplastic [KO:K00422] [EC:1.10.3.1]
            103641967  polyphenol oxidase, chloroplastic [KO:K00422] [EC:1.10.3.1]
            100275424  uncharacterized protein LOC100275424 [KO:K00422] [EC:1.10.3.1]
            100281477  uncharacterized protein LOC100281477 precursor [KO:K00422] [EC:1.10.3.1]
            100283178  polyphenol oxidase II [KO:K00422] [EC:1.10.3.1]
            103641120  polyphenol oxidase I, chloroplastic [KO:K00422] [EC:1.10.3.1]
            100279950  uncharacterized protein LOC100279950 [KO:K01593] [EC:4.1.1.28 4.1.1.105]
            103655034  tryptophan decarboxylase 1 [KO:K01593] [EC:4.1.1.28 4.1.1.105]
            100383025  uncharacterized protein LOC100383025 [KO:K01593] [EC:4.1.1.28 4.1.1.105]
            103655219  tryptophan decarboxylase 1 [KO:K01593] [EC:4.1.1.28 4.1.1.105]
            100274380  uncharacterized protein LOC100274380 [KO:K01593] [EC:4.1.1.28 4.1.1.105]
            100383438  uncharacterized protein LOC100383438 [KO:K00276] [EC:1.4.3.21]
            103641531  primary amine oxidase [KO:K00276] [EC:1.4.3.21]
            100279491  primary amine oxidase precursor [KO:K00276] [EC:1.4.3.21]
COMPOUND    C00082  L-Tyrosine
            C00355  3,4-Dihydroxy-L-phenylalanine
            C00483  Tyramine
            C00757  Berberine
            C00811  4-Coumarate
            C01179  3-(4-Hydroxyphenyl)pyruvate
            C01516  Morphine
            C01735  Morphinone
            C01795  Columbamine
            C01852  Secologanin
            C02105  (S)-Reticuline
            C02106  (S)-Scoulerine
            C02134  Allocryptopine
            C02890  Tetrahydropalmatine
            C02915  (S)-N-Methylcanadine
            C02916  (S)-Norlaudanosoline
            C03329  (S)-Canadine
            C03758  Dopamine
            C03765  4-Hydroxyphenylacetaldehyde
            C04043  3,4-Dihydroxyphenylacetaldehyde
            C04118  Isocorypalmine
            C05174  (S)-Cheilanthifoline
            C05175  Stylopine
            C05176  (S)-N-Methylcoclaurine
            C05177  Berbamunine
            C05178  (R)-Reticuline
            C05179  Salutaridine
            C05189  Protopine
            C05190  6-Hydroxyprotopine
            C05191  Dihydrosanguinarine
            C05193  12-Hydroxydihydrochelirubine
            C05194  Dihydrochelirubine
            C05202  3'-Hydroxy-N-methyl-(S)-coclaurine
            C05220  Salutaridinol
            C05243  (R)-N-Methylcoclaurine
            C05247  10-Hydroxydihydrosanguinarine
            C05315  Palmatine
            C05316  Dihydromacarpine
            C05322  7-O-Acetylsalutaridinol
            C06160  (S)-Norcoclaurine
            C06161  (S)-Coclaurine
            C06162  Sanguinarine
            C06163  (S)-cis-N-Methylstylopine
            C06165  Macarpine
            C06167  1,2-Dehydroreticuline
            C06171  Codeinone
            C06172  Neopinone
            C06173  Thebaine
            C06174  Codeine
            C06175  Oripavine
            C06327  Chelirubine
            C06511  Guattegaumerine
            C06512  2'-Norberbamunine
            C06516  (R)-Norreticuline
            C06517  (S)-6-O-Methylnorlaudanosoline
            C06518  (S)-Nororientaline
            C06520  (S)-Norreticuline
            C06533  Papaverine
            C06546  Mescaline
            C07304  Deacetylisoipecoside
            C07307  Deacetylipecoside
            C07547  Tubocurarine
            C07592  Colchicine
            C08521  Caranine
            C08526  Galanthamine
            C08527  Haemanthamine
            C08532  Lycorine
            C09248  Tubulosine
            C09328  Alangimarckine
            C09330  Alangiside
            C09337  Ankorine
            C09390  Cephaeline
            C09421  Emetine
            C09541  (S)-Isoboldine
            C09581  Magnoflorine
            C09592  alpha-Narcotine
            C09593  Narcotoline
            C09654  (+)-Tetrandrine
            C11250  Demecolcine
            C11813  Demethylalangiside
            C11814  Demethylisoalangiside
            C11815  Isoalangiside
            C11816  Protoemetine
            C11817  Deoxytubulosine
            C11818  (R)-Canadine
            C12162  Crinine
            C12173  Norgalanthamine
            C12180  (-)-8-Demethylmaritidine
            C12193  Vittatine
            C12231  Anhalamine
            C15530  Corydaline
            C16700  3,4-Dihydroxybenzaldehyde
            C16701  Norbelladine
            C16702  4'-O-Methylnorbelladine
            C16703  N-Demethylnarwedine
            C16704  Anhalonidine
            C16705  Anhalonine
            C16706  4-Hydroxydihydrocinnamaldehyde
            C16707  (S)-Autumnaline
            C16708  Isoandrocymbine
            C16709  O-Methylandrocymbine
            C16710  N-Formyldemecolcine
            C16712  Deacetylcolchicine
            C16713  Floramultine
            C16714  Kreysigine
            C17591  (S)-Corytuberine
            C17592  Laudanine
            C20297  Narcotine hemiacetal
            C20299  Papaveroxine
            C21405  (4aS,10bR)-Noroxomaritidine
            C21406  (4aR,10bS)-Noroxomaritidine
            C21566  6-O-Methyldeacetylisoipecoside
            C21583  6-O-Methyl-N-deacetylisoipecoside aglycon
            C21584  7'-O-Dmethylcephaeline
            C21586  (S)-1-Hydroxy-N-methylcanadine
            C21587  (13S,14R)-1,13-Dihydroxy-N-methylcanadine
            C21588  (13S,14R)-1-Hydroxy-13-O-acetyl-N-methylcanadine
            C21589  (13S,14R)-1,8-Dihydroxy-13-O-acetyl-N-methylcanadine
            C21590  4'-O-Desmethyl-3-O-acetylpapaveroxine
            C21591  3-O-Acetylpapaveroxine
            C21599  4'-O-Desmethylpapaveroxine
            C21600  Narcotoline hemiacetal
            C21630  (S)-Norlaudanine
            C21631  (S)-Tetrahydropapaverine
            C21633  Noroxopluviine
            C21634  Norcraugsodine
            C21635  (4aR,10bS)-Normaritidine
            C21637  Elwesine
            C21639  Maritinamine
REFERENCE   PMID:10811648
  AUTHORS   Morishige T, Tsujita T, Yamada Y, Sato F
  TITLE     Molecular characterization of the S-adenosyl-L-methionine:3'-hydroxy-N-methylcoclaurine 4'-O-methyltransferase involved in isoquinoline alkaloid biosynthesis in Coptis japonica.
  JOURNAL   J Biol Chem 275:23398-405 (2000)
            DOI:10.1074/jbc.M002439200
REFERENCE   PMID:12423366
  AUTHORS   Morishige T, Dubouzet E, Choi KB, Yazaki K, Sato F
  TITLE     Molecular cloning of columbamine O-methyltransferase from cultured Coptis japonica cells.
  JOURNAL   Eur J Biochem 269:5659-67 (2002)
            DOI:10.1046/j.1432-1033.2002.03275.x
REFERENCE   PMID:14675446
  AUTHORS   Ounaroon A, Decker G, Schmidt J, Lottspeich F, Kutchan TM
  TITLE     (R,S)-Reticuline 7-O-methyltransferase and (R,S)-norcoclaurine 6-O-methyltransferase of Papaver somniferum - cDNA cloning and characterization of methyl transfer enzymes of alkaloid biosynthesis in opium poppy.
  JOURNAL   Plant J 36:808-19 (2003)
            DOI:10.1046/j.1365-313X.2003.01928.x
REFERENCE   PMID:18230623
  AUTHORS   Ikezawa N, Iwasa K, Sato F
  TITLE     Molecular cloning and characterization of CYP80G2, a cytochrome P450 that catalyzes an intramolecular C-C phenol coupling of (S)-reticuline in magnoflorine biosynthesis, from cultured Coptis japonica cells.
  JOURNAL   J Biol Chem 283:8810-21 (2008)
            DOI:10.1074/jbc.M705082200
REFERENCE   PMID:18476877
  AUTHORS   Facchini PJ, De Luca V
  TITLE     Opium poppy and Madagascar periwinkle: model non-model systems to investigate alkaloid biosynthesis in plants.
  JOURNAL   Plant J 54:763-84 (2008)
            DOI:10.1111/j.1365-313X.2008.03438.x
REFERENCE   PMID:18492807
  AUTHORS   Minami H, Kim JS, Ikezawa N, Takemura T, Katayama T, Kumagai H, Sato F
  TITLE     Microbial production of plant benzylisoquinoline alkaloids.
  JOURNAL   Proc Natl Acad Sci U S A 105:7393-8 (2008)
            DOI:10.1073/pnas.0802981105
REFERENCE   
  AUTHORS   Rueffer M, Bauer W, Zenk MH.
  TITLE     The formation of corydaline and related alkaloids in Corydalis cava in vivo and in vitro.
  JOURNAL   Can J Chem 72:170-175 (1994)
            DOI:10.1139/v94-026
REFERENCE   
  AUTHORS   Sekine Y, Crevelling C, Bell M, Brossi A.
  TITLE     Mammalian alkaloids: O-methylation of (+-)-norcoclaurine-1-carboxylic acid and related isoquinolines including (S)- and (R)-norcoclaurine with 14C-labeled S-adenosyl-L-methionine in presence of mammalian catechol O-methyltransferase.
  JOURNAL   Helv Chim Acta 73:426-432 (1990)
            DOI:10.1002/hlca.19900730222
REFERENCE   
  AUTHORS   De-Eknamkul W, Tanahashi T, Zenk MH.
  TITLE     Enzymic 10-hydroxylation and 10-O-methylation of dihydrosanguinarine in dihydrochelirubine formation by Eschscholtzia.
  JOURNAL   Phytochemistry 31:2713-2717 (1992)
            DOI:10.1016/0031-9422(92)83617-8
REFERENCE   
  AUTHORS   Kammerer L, De-Eknamkul W, Zenk MH.
  TITLE     Enzymic 12-hydroxylation and 12-O-methylation of dihydrochelirubine in dihydromacarpine formation by Thalictrum bulgaricum.
  JOURNAL   Phytochemistry 36:1409-1416 (1994)
            DOI:10.1016/S0031-9422(00)89732-0
REFERENCE   PMID:24241413
  AUTHORS   Schumacher HM, Zenk MH
  TITLE     Partial purification and characterization of dihydrobenzophenanthridine oxidase from Eschscholtzia californica cell suspension cultures.
  JOURNAL   Plant Cell Rep 7:43-6 (1988)
            DOI:10.1007/BF00272975
REFERENCE   
  AUTHORS   Rueffer M, Zenk MH.
  TITLE     Enzymatic formation of protopines by a microsomal cytochrome P-450 system of Corydalis vaginans.
  JOURNAL   Tetrahedron Lett 28:5307-5310 (1987)
            DOI:10.1016/S0040-4039(00)96715-7
REL_PATHWAY zma00350  Tyrosine metabolism
            zma00360  Phenylalanine metabolism
            zma00400  Phenylalanine, tyrosine and tryptophan biosynthesis
            zma00902  Monoterpenoid biosynthesis
KO_PATHWAY  ko00950
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