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Literature summary extracted from

  • Desgagne-Penix, I.; Facchini, P.
    Systematic silencing of benzylisoquinoline alkaloid biosynthetic genes reveals the major route to papaverine in opium poppy (2012), Plant J., 72, 331-344.
    View publication on PubMed

Cloned(Commentary)

EC Number Cloned (Comment) Organism
2.1.1.140 real-time quantitative PCR analysis of target gene transcript levels, comparison of target gene transcript levels and papaverine content in individual opium poppy plants infiltrated with Agrobacterium tumefaciens harboring control and gene-specific pTRV2 constructs Papaver somniferum

Protein Variants

EC Number Protein Variants Comment Organism
2.1.1.140 additional information virus-induced gene silencing in opium poppy to functionally characterize six genes potentially involved in papaverine biosynthesis, e.g. the gene encoding coclaurine N-methyltransferase, altered alkaloid content phenotypes, overview. Norlaudanine is only detected in CNMT-suppressed plants Papaver somniferum

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
1.14.14.102 (S)-N-methylcoclaurine + [reduced NADPH-hemoprotein reductase] + O2 Papaver somniferum
-
 (S)-3'-hydroxy-N-methylcoclaurine + [oxidized NADPH-hemoprotein reductase] + H2O
-
 ?
2.1.1.140 S-adenosyl-L-methionine + (S)-coclaurine Papaver somniferum
-
 S-adenosyl-L-homocysteine + (S)-N-methylcoclaurine
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
1.14.14.102 Papaver somniferum
-
-
-
2.1.1.116 Papaver somniferum
-
 opium poppy
-
2.1.1.128 Papaver somniferum
-
 opium poppy, cultivar Bea's Choice
-
2.1.1.140 Papaver somniferum
-
-
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.14.14.102 (S)-N-methylcoclaurine + [reduced NADPH-hemoprotein reductase] + O2
-
 Papaver somniferum (S)-3'-hydroxy-N-methylcoclaurine + [oxidized NADPH-hemoprotein reductase] + H2O
-
 ?
2.1.1.128 S-adenosyl-L-methionine + (S)-norcoclaurine preferred substrate Papaver somniferum S-adenosyl-L-homocysteine + (S)-coclaurine
-
 ?
2.1.1.128 S-adenosyl-L-methionine + (S)-norlaudanosoline
-
 Papaver somniferum S-adenosyl-L-homocysteine + 6-O-methylnorlaudanosoline
-
 ?
2.1.1.140 S-adenosyl-L-methionine + (S)-coclaurine
-
 Papaver somniferum S-adenosyl-L-homocysteine + (S)-N-methylcoclaurine
-
 ?

Synonyms

EC Number Synonyms Comment Organism
1.14.14.102 N-methylcoclaurine 3'-hydroxylase
-
 Papaver somniferum
1.14.14.102 NMCH
-
 Papaver somniferum
2.1.1.116 (S)-3'-hydroxy-N-methylcoclaurine 4-O-methyltransferase
-
 Papaver somniferum
2.1.1.128 (S)-norcoclaurine 6-O-methyltransferase
-
 Papaver somniferum
2.1.1.128 6OMT
-
 Papaver somniferum
2.1.1.128 Norcoclaurine 6-O-methyltransferase
-
 Papaver somniferum
2.1.1.140 6OMT
-
 Papaver somniferum
2.1.1.140 CNMT
-
 Papaver somniferum
2.1.1.140 coclaurine N-methyltransferase
-
 Papaver somniferum

Cofactor

EC Number Cofactor Comment Organism Structure
2.1.1.140 S-adenosyl-L-methionine
-
 Papaver somniferum

General Information

EC Number General Information Comment Organism
1.14.14.102 malfunction enzyme silencing is associated with a 22% reduction in total alkaloid accumulation, with a notable decrease in the levels of thebaine and codeine compared with controls. In contrast, absolute levels of morphine and papaverine are not affected Papaver somniferum
2.1.1.116 malfunction suppression of the gene encoding (S)-3'-hydroxy-N-methylcoclaurine 4-O-methyltransferase reduces papaverine content in opium poppy Papaver somniferum
2.1.1.128 malfunction suppression of norcoclaurine 6-O-methyltransferase transcript levels significantly suppresses total alkaloid accumulation in opium poppy (73% compared to the controls). However, the relative abundance of morphine increased to 55% of the total alkaloid content. Suppression of the enzyme does not significantly affect (S)-3'-hydroxy-N-methylcoclaurine 1 or (S)-3'-hydroxy-N-methylcoclaurine 2 transcript levels Papaver somniferum
2.1.1.140 malfunction plants exhibiting reduced CNMT transcript levels show a significant fourfold increase in the relative abundance of papaverine, and a reduction in the accumulation of thebaine and noscapine. Norlaudanine is only detected in CNMT-suppressed plants. The levels of several N-methylated compounds, including N-methylcoclaurine, N,N-dimethylcoclaurine, 4'-O-methyl-N-methylcoclaurine, reticuline, N,N-dimethylreticuline, codamine, laudanine, laudanosine and salutaridine, and four phathelideisoquinoline alkaloids (i.e. narcotoline, noscapine, N,N-dimethylnarcotine and another noscapine-like compound) are also reduced in CNMT-suppressed plants Papaver somniferum
2.1.1.140 metabolism the enzyme is involved in the biosynthesis pathways of alkaloids in Papaver somniferum, overview. Subsequent 6-O-methylation, N-methylation, 3'-hydroxylation and 4'-O-methylation convert (S)-norcoclaurine to (S)-reticuline, which is a branch-point intermediate in the formation of most BIA structural sub-groups, including morphinan (e.g. morphine), phthalideisoquinoline (e.g. noscapine) and benzophenanthridine (e.g. sanguinarine) alkaloids Papaver somniferum