130-86-9Relevant articles and documents
ENZYMATIC FORMATION OF PROTOPINES BY A MICROSOMAL CYTOCHROME P-450 SYSTEM OF CORYDALIS VAGINANS
Rueffer, M.,Zenk, M. H.
, p. 5307 - 5310 (1987)
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.
Isolation and characterization of a cDNA encoding (S)-cis-N-methylstylopine 14-hydroxylase from opium poppy, a key enzyme in sanguinarine biosynthesis
Beaudoin, Guillaume A.W.,Facchini, Peter J.
, p. 597 - 603 (2013)
Sanguinarine is a benzo[. c]phenenthridine alkaloid with potent antimicrobial properties found commonly in plants of the Papaveraceae, including the roots of opium poppy (. Papaver somniferum). Sanguinarine is formed from the central 1-benzylisoquinoline intermediate (. S)-reticuline via the protoberberine alkaloid (. S)-scoulerine, which undergoes five enzymatic oxidations and an N-methylation. The first four oxidations from (. S)-scoulerine are catalyzed by cytochromes P450, whereas the final conversion involves a flavoprotein oxidase. All but one gene in the biosynthetic pathway from (. S)-reticuline to sanguinarine has been identified. In this communication, we report the isolation and characterization of (. S)-. cis-. N-methylstylopine 14-hydroxylase (MSH) from opium poppy based on the transcriptional induction in elicitor-treated cell suspension cultures and root-specific expression of the corresponding gene. Along with protopine 6-hydroxylase, which catalyzes the subsequent and penultimate step in sanguinarine biosynthesis, MSH is a member of the CYP82N subfamily of cytochromes P450. The full-length MSH cDNA was expressed in Saccharomyces cerevisiae and the recombinant microsomal protein was tested for enzymatic activity using 25 benzylisoquinoline alkaloids representing a wide range of structural subgroups. The only enzymatic substrates were the N-methylated protoberberine alkaloids N-methylstylopine and N-methylcanadine, which were converted to protopine and allocryptopine, respectively.
On the synthesis of protopine alkaloids
Wada, Yasuhiro,Kaga, Harumi,Uchiito, Shiho,Kumazawa, Eri,Tomiki, Miho,Onozaki, Yu,Kurono, Nobuhito,Tokuda, Masao,Ohkuma, Takeshi,Orito, Kazuhiko
, p. 7301 - 7306 (2008/02/11)
(Chemical Equation Presented) For the synthesis of protopine alkaloids, we studied a reaction sequence based on a ring enlargement of indeno[2,1-a][3] benzazepines by a singlet oxygen oxygenation, followed by conversion of an amide carbonyl group of the resultant 10-membered keto-lactam to a methylene group, which is the last step for completion of the synthesis. The key substances, indeno[2,1-a][3]benzazepines, were prepared by Bischler-Napieralski cyclization of alkoxy-substituted 1-(2-bromobenzyl)-3-benzazepin-2-ones. Steric effects of the substituents in this synthesis were examined.
