Related Experiment Video
Updated: Apr 6, 2026

Isolation and Screening from Soil Biodiversity for Fungi Involved in the Degradation of Recalcitrant Materials
Published on: May 16, 2022
Biotransformation of oleanolic and maslinic methyl esters by Rhizomucor miehei CECT 2749
Antonio Martinez1, Alberto Perojil1, Francisco Rivas1
1Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Granada, E-18071 Granada, Spain.
Abstract:
The pentacyclic triterpenoids methyl oleanolate, methyl maslinate, methyl 3β-hydroxyolean-9(11),12-dien-28-oate, and methyl 2α,3β-dihydroxy-12β,13β-epoxyolean-28-oate were biotransformed by Rhizomucor miehei CECT 2749. Microbial transformation of methyl oleanolate produced only a 7β,30-dihydroxylated metabolite with a conjugated 9(11),12-diene system in the C ring. Biotransformation of the substrate with this 9(11),12-diene system gave the same 7β,30-dihydroxylated compound together with a 7β,15α,30-trihydroxyl derivative. The action of this fungus (R. miehei) on methyl maslinate was more varied, isolating metabolites with a 30-hydroxyl group, a 9(11),12-diene system, an 11-oxo group, or an 12-oxo group. Microbial transformation of the substrate with a 12β,13β-epoxy function resulted in the isolation of two metabolites with 12-oxo and 28,13β-olide groups, hydroxylated or not at C-7β, together with a 30-hydroxy-12-oxo derivative. The structures of these derivatives were deduced by extensive and rigorous spectroscopic studies.
Related Concept Videos
Production of Organic Acids
Hydroboration-Oxidation of Alkenes
Alkylation of β-Diester Enolates: Malonic Ester Synthesis
Fungal Group Zygomycota
Drug Biotransformation: Overview
Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis

