Bioconversions of ergot alkaloids

Biotransformation of Chanoclavine by Euphorbia calyptrata Cell Culture

“…Reactions of the ergoline system with peroxidases are well documented. , Various 8-hydroxy, 10-hydroxy, and epoxy compounds are known, and N-6 demethylation has been observed. ,− Another reactive site in this skeleton is position 2. Substitution at position 2 leads to 2,3-dihydro-2-oxo- or 2,3-dihydro-2-oxo-3-hydroxyderivatives. , Oxidative B-ring opening was reported in later fermentation stages of Claviceps purpurea .…”

“…Ergot alkaloids and their derivatives exhibit various physiological effects widely used in medicine. − The majority of newly developed drugs of this group are semisynthetic compounds . Some simple representatives of this class (e.g., agroclavine or chanoclavine) are available in large quantities from submerged cultivation of certain Claviceps strains. , One possible way that their functionalization may lead to new prospective drugs is through biotransformation . So far, biooxidation of agroclavine, targeted to its hydroxy derivatives, has been extensively studied .…”

Dimerization of Lysergene by Euphorbia calyptrata Cell Cultures

“…Attempts to derivatize or functionalize 1 often produce complex mixtures. Therefore, we turned to biotransformations that operate under mild conditions and are often regioselective or enantioselective …”

“…The biotransformation of lysergene ( 1 ) has not been investigated, except for the study of its incorporation into other ergot alkaloids (lysergol, isolysergol, penniclavine, and isopenniclavine) by Claviceps purpurea . , Plant cell cultures have proven to be very suitable for the transformation of ergot alkaloids. , Most of the reactions observed are oxidative in nature. Therefore, cultures of Euphorbia calyptrata Coss & Dur (Euphorbiaceae), exhibiting a high oxidative capacity, were tested to study the biotransformation of lysergene ( 1 ).…”