Biotransformation of oleanolic and maslinic methyl esters by Rhizomucor miehei CECT 2749

Identification of gut‐derived metabolites of maslinic acid, a bioactive compound from Olea europaea L

“…The contribution of CYP450 enzymes in the metabolism of maslinic acid had been studied previously with the use of the fungi Cunninghamella and Rhizomucor that are models of mammalian drug metabolism. Incubation of maslinic acid with Cunninghamella and Rhizomucor yielded to metabolites in agreement with the ones detected in our results. In these studies, the chemical structure of the derivatives was elucidated based on the use of nuclear magnetic resonance and high‐resolution mass spectral analyses.…”

“…Moreover, a simple dehydrogenation took place in this biotransformation level and so, the diene system between 9/11 and 11/12 was obtained (metabolite M5) in agreement with the results obtained with incubation by Rhizomucor . In the second biotransformation level there were five metabolites as consequence of two biotransformation processes, and thus, the hydroxylation/ dehydrogenation drove to the metabolites M2‐a (11‐keto) and M2‐b (11/12 epoxy) . In addition in this biotransformation level a double dihydroxylation process was present and three metabolites were formed M3‐a (30, 7β‐diOH), M3‐b (30, 15α‐diOH), and M3‐c (7β, 15α‐diOH) by combination of the monohydroxylated compounds of first level.…”

“…4). In the first one, a mono hydroxylation occurred in different position of the triterpene skeleton (position 30, 7␤, and 15␣) and the metabolites M1-a, M1-b, and M1-c were formed as previously described in the fungi [21][22][23]. Moreover, a simple dehydrogenation took place in this biotransformation level and so, the diene system between 9/11 and 11/12 was obtained (metabolite M5) in agreement with the results obtained with incubation by Rhizomucor [22].…”

“…In the second biotransformation level there were five metabolites as consequence of two biotransformation processes, and thus, the hydroxylation/ dehydrogenation drove to the metabolites M2-a (11-keto) and M2-b (11/12 epoxy) [22,23]. In addition in this biotransformation level a double dihydroxylation process was present and three metabolites were formed M3-a (30, 7␤-diOH), M3-b (30, 15␣-diOH), and M3-c (7␤, 15␣-diOH) [21][22][23] by combination of the monohydroxylated compounds of first level. Finally, the third biotransformation level included only two metabolites formed by three microbiological actions from maslinic acid, starting from the metabolites of first and second levels.…”

Regio- and enantioselective microbial hydroxylation and evaluation of cytotoxic activity of β-cyclocitral-derived halolactones

“…The biotransformations catalyzed by whole cells are convenient and useful biotechnological tools, especially taking into consideration that majority of hydroxylation processes are mediated by membrane enzymes hence they cannot be easily purified. Different microorganisms can be applied to the enantioselective hydroxylation processes [5, 6]. In our present work we tested thirty strains of filamentous fungi and yeast from seventeen different genus.…”