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

  title={Enzymatic formation of protopines by a microsomal cytochrome P-450 system of Corydalis vaginans},
  author={M. Rueffer and M. Zenk},
  journal={Tetrahedron Letters},
Abstract A microsomal cytochrome P-450-NADPH dependent enzyme which hydroxylates stereo- and regiospecifically carbon atom 14 of (S)- cis -N- methyltetrahydroprotoberberines has been discovered in a number of plant cell cultures originating from species containing protopine alkaloids; the monooxygenase was solubilized, partially purified (100-fold) and characterized. 
One step enzymatic synthesis of dihydrosanguinarine from protopine
Abstract A microsomal cytochrome P-450 NADPH dependent enzyme which hydroxylates carbon-6 of protopine has been discovered and characterized; the monooxygenase reaction leads to 6-hydroxyprotopineExpand
Enzymatic Biosynthesis of Vomilenine, a Key Intermediate of the Ajmaline Pathway, Catalyzed by a Novel Cytochrome P 450-Dependent Enzyme from Plant Cell Cultures of Rauwolfia serpentina
The investigation of the taxonomical distribution of the enzyme indicated that vinorine hydroxylase is exclusively present in ajmaline-producing plant cells, suggesting that vInorine Hydroxylases is a cytochrome P450-dependent monooxygenase. Expand
Plant cytochrome P450.
The present status of plant cytochrome P450 research is reviewed. A comparison of the properties of this group of cytochrome proteins with those of other microsomal b-type haem proteins is made. TheExpand
Glycyrrhetinic acid 24-hydroxylase activity in microsomes of cultured licorice cells
Abstract 18β-Glycyrrhetinic acid 24-hydroxylase activity was detected in the microsomal fraction prepared from Glycyrrhiza glabra cell suspension cultures. The enzymatic activity required both NADPHExpand
Two methylenedioxy bridge forming cytochrome P-450 dependent enzymes are involved in (S)-stylopine biosynthesis
Abstract The enzymatic synthesis of the alkaloids ( S )-[10-OC 3 H 3 ]scoulerine and ( S )-[3-OC 3 H 3 ]cheilanthifoline is described. A microsomal preparation from Eschscholtzia californica cellExpand
Enzymic 12-hydroxylation and 12-O-methylation of dihydrochelirubine in dihydromacarpine formation by Thalictrum bulgaricum
This discovery leads to the complete sequence of macarpine biosynthesis which has thus far been the longest secondary product pathway completely clarified at the enzymic level. Expand
Elicitor induction and characterization of microsomal protopine-6-hydroxylase, the central enzyme in benzophenanthridine alkaloid biosynthesis
The hydroxylase is specifically present in different plant species that produce benzo[c]phenanthridine alkaloids in culture and also respond to induction by the elicitor, suggesting that the enzyme is a cytochrome P-450 linked monooxygenase. Expand
Mammalian Cytochrome P450 Enzymes Catalyze the Phenol-coupling Step in Endogenous Morphine Biosynthesis*
(S)-Reticuline, a substrate of both P450 enzymes, yielded the phenol-coupled alkaloids (+)-isoboldine, (+)-corytuberine, (−)-pallidine, and sinoacutine; none of these serve as a morphine precursor. Expand
Enzymology and molecular biology of alkaloid biosynthesis
Abstract The biosynthetic pathways leading to the benzophenanthridine alkaloid, sanguinarine, and the indole alkaloids, ajmalicine and ajmaline, have been solved at the level of the individualExpand
Cloning and heterologous expression of NADPH-cytochrome P450 reductases from the Papaveraceae.
SDS-PAGE of the purified native P. somniferum enzyme as well as genomic DNA gel blot analysis indicate that two cytochrome P450 reductase isoforms are present in each species, supported by translation of nucleotide sequences obtained from the PCR-generated partial cDNAs and the full-length c DNAs isolated from lambda libraries. Expand


S-adenosyl-l-methionine: (S) -7,8,13, 14-tetrahydroberberine--n-methyltransferase, a branch point enzyme in the biosynthesis of benzophenanthridine and protopine alkaloids.
The enzyme which transfers the CH3-group of S-adenosylmethionine to the nitrogen atom of (S)-tetrahydroberberine and (S)-stylopine is found to occur in a number of plant cell cultures originatingExpand
Partial Purification and Properties of (S)-Norlaudanosoline Synthase from Eschscholtzia tenuifolia Cell Cultures.
By means of isoelectric focusing and disc-gel electrophoresis evidence was obtained for the existence of four norlaudanosoline synthase isoenzymes, none of which catalyses the reaction of dopamine with 3,4-dihydroxyphenylpyruvate, the key intermediate in the formation of isoquinoline alkaloids occurring in the plant kingdom. Expand
Biosynthesis of Benzo[c]phenanthridine Alkaloids Sanguinarine, Chelirubine and Macarpine
The biosynthesis of the benzo[c]phenanthridine alkaloids was investigated in a cell suspension culture of Macleaya cordata (papaveraceae). Feeding experiments define the biosynthetic pathwayExpand
Zur Biosynthese der Alkaloide vom Rhoeadin‐Typ
It was shown, using Papaver bracteatum plants, that [N-14CH3, 8-14C]dl-tetrahydropalmatine methiodide (Ia) is incorporated with high efficiency into alpinigenine (III), and apparently the incorporation of the N-quaternary salt is a specific one. Expand
Biosynthesis of alpinigenine by way of tetrahydroprotoberberine and protopine intermediates
Abstract In the biosynthesis of the benzazepine alkaloid alpinigenine a N -methylation step followed by hydroxylation α to nitrogen has now been shown more conclusively to be involved in theExpand
Rapid isolation of a plant microsomal fraction by Mg2+ — precipitation
A procedure for the rapid preparation of a plant microsomal fraction by Mg2+-precipitation was developed and will be described in this communication. Expand
Tetrahedron Letters
A new strategy for the synthesis of (+)-vernolepin (1), (+)-vernodalin (2), and (+)-8-deoxyvernolepin (3), from the accessible germacrolides (+)-salonitenolide (4) and (+)-costunolide (5), has beenExpand
and K
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