6533b856fe1ef96bd12b1c18

RESEARCH PRODUCT

Enzymatic formation of the sarpagan-bridge: a key step in the biosynthesis of sarpagine- and ajmaline-type alkaloids.

Doris SchmidtJoachim Stöckigt

subject

Pharmacologychemistry.chemical_classificationbiologyApocynaceaeStereochemistryAlkaloidOrganic ChemistryPharmaceutical ScienceCytochrome P450biology.organism_classificationAnalytical ChemistryAjmalinechemistry.chemical_compoundEnzymeComplementary and alternative medicineBiochemistrychemistryBiosynthesisStrictosidineDrug DiscoverymedicineMicrosomebiology.proteinMolecular Medicinemedicine.drug

description

The glucoalkaloid strictosidine has been converted under cell-free conditions into 10-deoxysarpagine (= normacusine B) in the presence of a crude soluble enzyme extract and microsomal protein isolated from cell suspensions of Rauwolfia serpentina. The enzymatic formation of this alkaloid bearing the C-5/C-16 bond (sarpagan-bridge), which is characteristic for all sarpagine- and ajmaline-type alkaloids, is dependent on NADPH and oxygen. Inhibition studies indicate that for the synthesis of 10-deoxysarpagine a cytochrome P450 dependent monoxygenase is necessary.

10.1055/s-2006-958067https://pubmed.ncbi.nlm.nih.gov/17238077