Molecular cloning and characterization of a cytochrome P450 in sanguinarine biosynthesis from Eschscholzia californica cells

Reconstitution of a 10-gene pathway for synthesis of the plant alkaloid dihydrosanguinarine in Saccharomyces cerevisiae

“…The next two biosynthetic steps are catalysed by the P450 hydroxylases (S)-cis-N-methylstylopine 14-hydroxylase (MSH) and protopine 6-hydroxylase (P6H). Both enzymes were recently identified and characterized from P. somniferum and Eschscholzia californica, respectively (CYP82N4 and CYP82N2v2) 25,27 . 6-Hydroxyprotopine spontaneously rearranges to dihydrosanguinarine.…”

“…The last steps in sanguinarine biosynthesis were recently elucidated, laying the groundwork for complete synthesis of this molecule in a heterologous host [25][26][27] .…”

The Roles of a Flavone-6-Hydroxylase and 7-O-Demethylation in the Flavone Biosynthetic Network of Sweet Basil

“…CYP82E4 and CYP82E5 from Nicotiana tabacum were identified as nicotine N-demethylases (27). CYP82N2v2 acts as protopine 6-hydroxylase in sanguinarine biosynthesis in Eschscholzia californica (34). CYP82G1 is the homoterpene synthase in Arabidopsis (35).…”

Benzylisoquinoline alkaloid biosynthesis in opium poppy

“…1) from protopine is catalyzed by protopine 6-hydroxylase (P6H), another member of the CYP82 N subfamily (Tanahashi and Zenk 1990;Takemura et al 2012). The resulting 6-hydroxylation results in a spontaneous rearrangement of 6-hydroxyprotopine to dihydrosanguinarine, which is oxidized to sanguinarine by the FAD-linked enzyme dihydrobenzophenanthridine oxidase (DBOX) .…”