Isoquinoline alkaloid biosynthesis

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.

Metabolism; Biosynthesis of other secondary metabolites

PMID:10811648

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Eur J Biochem 269:5659-67 (2002)

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PMID:18230623

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J Biol Chem 283:8810-21 (2008)

PMID:18476877

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Plant J 54:763-84 (2008)

PMID:18492807

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Proc Natl Acad Sci U S A 105:7393-8 (2008)

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The formation of corydaline and related alkaloids in Corydalis cava in vivo and in vitro.

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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.

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Kammerer L, De-Eknamkul W, Zenk MH.

Enzymic 12-hydroxylation and 12-O-methylation of dihydrochelirubine in dihydromacarpine formation by Thalictrum bulgaricum.

Phytochemistry 36(6):1409-1416 (1994)

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Partial purification and characterization of dihydrobenzophenanthridine oxidase from Eschscholtzia californica cell suspension cultures.

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Enzymatic formation of protopines by a microsomal cytochrome P-450 system of Corydalis vaginans.

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