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Entry
map00950                    Pathway                                

Name
Isoquinoline alkaloid biosynthesis
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
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Isoquinoline alkaloid biosynthesis
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Reference
  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)
Reference
  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)
Reference
  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)
Reference
  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)
Reference
  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)
Reference
  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)
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)
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
Helvetica Chimica Acta 73(2):426-432 (1990)
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(8):2713-2717 (1992)
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(6):1409-1416 (1994)
Reference
  Authors
Schumacher HM, Zenk MH.
  Title
Partial purification and characterization of dihydrobenzophenanthridine oxidase from Eschscholtzia californica cell suspension cultures.
  Journal
Plant Cell Reports 7:43-46 (1988)
Reference
  Authors
Rueffer M, Zenk MH.
  Title
Enzymatic formation of protopines by a microsomal cytochrome P-450 system of Corydalis vaginans.
  Journal
Tetrahedron Letters 28(44):5307-5310 (1987)
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