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. 2015 Feb 3;2015:252434. doi: 10.1155/2015/252434

Table 6.

A comparison of DDA and MDA metabolites in different metabolic procedures.

Alkaloids Stomach Intestine Liver (CYP450s, phase I metabolism)
DDAs Ester hydrolysis Ester hydrolysis commonly occurs at C-8 Ester hydrolysis commonly occurs at C-8
Hydroxylation at 2′/3′/4′ of the benzoyl group Hydroxylation at C-10 Hydroxylation at C-2
Deoxylation at C-3/15 Deoxylation at C-3/15 Deoxylation at C-3/15
Demethylation at the methoxy group Demethylation at the methoxy group,
often at C-1/6/16 or the N-methyl group
Demethylation at the methoxy group,
often at C-1/6/16 or the N-methyl group
Didemethylation at the methoxy group or deethylation at the N-ethyl group NAa Didemethylation at the methoxy group or deethylation at the N-ethyl group
NA Deacetoxylation (pyrolysis) Deacetoxylation (pyrolysis)
NA NA Dehydrogenation at C-3/15
NA NA Demethylation at C-1/6/16 or the N-methyl group with dehydrogenation at C-3/15;
demethylation with dehydrogenation at the same methoxyl group, O remained as a carbonyl group.
NA Demethylation and deoxylation NA
Lipoalkaloids via ester exchange at C-8 with long chain fatty acids. Lipoalkaloids via ester exchange at C-8 with short/long chain fatty acids. NA

MDAs NA NA Hydroxylation
Demethylation
Didemethylation or deethylation
Dehydrogenation
Demethylation and (di)dehydrogenation

aNot available.