ENTRY       gmx00950                    Pathway
NAME        Isoquinoline alkaloid biosynthesis - Glycine max (soybean)
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 gmx00950  Isoquinoline alkaloid biosynthesis
DBLINKS     GO: 0033075
ORGANISM    Glycine max (soybean) [GN:gmx]
GENE        547509  AAT; aspartate aminotransferase glyoxysomal isozyme AAT1 precursor [KO:K14454] [EC:2.6.1.1]
            100804162  aspartate aminotransferase [KO:K14454] [EC:2.6.1.1]
            547813  aspartate aminotransferase, mitochondrial [KO:K14455] [EC:2.6.1.1]
            100814593  aspartate aminotransferase, mitochondrial [KO:K14455] [EC:2.6.1.1]
            100811514  aspartate aminotransferase P2, mitochondrial [KO:K00811] [EC:2.6.1.1]
            547792  aspartate aminotransferase [KO:K00811] [EC:2.6.1.1]
            100776446  bifunctional aspartate aminotransferase and glutamate/aspartate-prephenate aminotransferase [KO:K15849] [EC:2.6.1.1 2.6.1.78 2.6.1.79]
            100801361  bifunctional aspartate aminotransferase and glutamate/aspartate-prephenate aminotransferase [KO:K15849] [EC:2.6.1.1 2.6.1.78 2.6.1.79]
            100780254  aminotransferase superfamily protein [KO:K15849] [EC:2.6.1.1 2.6.1.78 2.6.1.79]
            732650  tyrosine aminotransferase [KO:K00815] [EC:2.6.1.5]
            100785132  probable aminotransferase TAT2 [KO:K00815] [EC:2.6.1.5]
            100800830  nicotianamine aminotransferase 1 [KO:K00815] [EC:2.6.1.5]
            100784392  probable aminotransferase TAT2 [KO:K00815] [EC:2.6.1.5]
            100792012  polyphenol oxidase, chloroplastic [KO:K00422] [EC:1.10.3.1]
            100803171  polyphenol oxidase A1, chloroplastic [KO:K00422] [EC:1.10.3.1]
            100789730  polyphenol oxidase A1, chloroplastic [KO:K00422] [EC:1.10.3.1]
            100802289  polyphenol oxidase A1, chloroplastic [KO:K00422] [EC:1.10.3.1]
            100037473  LOW QUALITY PROTEIN: polyphenol oxidase A1, chloroplastic [KO:K00422] [EC:1.10.3.1]
            100802763  polyphenol oxidase, chloroplastic [KO:K00422] [EC:1.10.3.1]
            100801369  polyphenol oxidase A1, chloroplastic [KO:K00422] [EC:1.10.3.1]
            100785410  polyphenol oxidase I, chloroplastic [KO:K00422] [EC:1.10.3.1]
            100037474  aureusidin synthase [KO:K00422] [EC:1.10.3.1]
            100798709  polyphenol oxidase A1, chloroplastic [KO:K00422] [EC:1.10.3.1]
            100801754  polyphenol oxidase I, chloroplastic [KO:K00422] [EC:1.10.3.1]
            100803874  polyphenol oxidase II, chloroplastic [KO:K00422] [EC:1.10.3.1]
            100798184  polyphenol oxidase A1, chloroplastic [KO:K00422] [EC:1.10.3.1]
            100787822  tyrosine decarboxylase [KO:K01593] [EC:4.1.1.28 4.1.1.105]
            100795274  tyrosine decarboxylase [KO:K01593] [EC:4.1.1.28 4.1.1.105]
            100791074  tyrosine decarboxylase 2 [KO:K01593] [EC:4.1.1.28 4.1.1.105]
            100802993  tyrosine decarboxylase [KO:K01593] [EC:4.1.1.28 4.1.1.105]
            547524  PAO1; peroxisomal copper-containing amine oxidase [KO:K00276] [EC:1.4.3.21]
            100819571  putative copper amine oxidase precursor [KO:K00276] [EC:1.4.3.21]
            100778802  copper methylamine oxidase [KO:K00276] [EC:1.4.3.21]
            100798722  copper methylamine oxidase isoform X1 [KO:K00276] [EC:1.4.3.21]
            100804651  primary amine oxidase [KO:K00276] [EC:1.4.3.21]
            100781472  primary amine oxidase 1 [KO:K00276] [EC:1.4.3.21]
            548000  DAO; copper amino oxidase precursor [KO:K00276] [EC:1.4.3.21]
            100802062  primary amine oxidase isoform X1 [KO:K00276] [EC:1.4.3.21]
            100800090  primary amine oxidase [KO:K00276] [EC:1.4.3.21]
            100802589  primary amine oxidase 1 [KO:K00276] [EC:1.4.3.21]
            100798399  primary amine oxidase [KO:K00276] [EC:1.4.3.21]
            100799555  primary amine oxidase [KO:K00276] [EC:1.4.3.21]
            100817454  copper methylamine oxidase isoform X1 [KO:K00276] [EC:1.4.3.21]
            100817473  primary amine oxidase [KO:K00276] [EC:1.4.3.21]
            100783091  copper methylamine oxidase [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 gmx00350  Tyrosine metabolism
            gmx00360  Phenylalanine metabolism
            gmx00400  Phenylalanine, tyrosine and tryptophan biosynthesis
KO_PATHWAY  ko00950
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