Tropane alkaloid, biotransformation

Table 7 Tropane alkaloid analysis by LC-MS and LC-MS/MS for biotransformation studies in vivo and in vitro...

Fig. 7 Selected biotransformation products of diverse tropane alkaloids identified by LC-MS/MS approaches. Depicted metabolites are only an exert of those presented by Chen et al. for anisodamine (Ada) [6], atropine (Atr) [51], and scopolamine (Sep) [7] as well as by He et al. for benztropine (Benz) [59]. Structures were identified from in vivo and in vitro samples following diverse modes of MS/MS analysis as discussed in the section Biotransformation studies...

Fig. 8 Product ion spectra of diverse tropane alkaloids after collision-induced dissociation. Spectra were obtained after positive electrospray ionization and collision-induced dissociation (CID) with nitrogen in a QTrap 4000 instrument. Common structural elements cause generation of corresponding diagnostic fragments, e.g. m/z 124 and 93. For structural assignment of biotransformation products similar fragmentation pattern were produced and interpreted as shown by Chen et al. [6, 7, 51] and He et al. [59]...

Production can be increased by addition of precursors to the culture media, in which cases the precursors are not metabolized in the medium and, after uptake, appear in the right compartment of the plant cell. For C. roseus cultures, for example, it was found that increased indole alkaloid production was obtained after feeding with L-tryptophan, tryptamine, secologanin, loganin, loganic acid, or shikimic acid (20). Cell cultures have also been used for biotransformations, for example, the conversion of (-)-codeinone to (-)-codeine in Papaver somniferum cultures (100). For the tropane alkaloids a large number of precursor feeding and biotransformation studies with cultures of various solanaceous plants have been performed (see below). 

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