The in vitro metabolism of a widespread natural product, trachyloban-19-oic acid (1), by the fungal species Mucor plumbeus was studied in a sucrose-yeast liquid medium. Two products were isolated, and their structures were determined by spectroscopic means as 7β-hydroxytrachyloban-19-oic acid (5) and trachyloban-19-O-β-D-glucopyranosyl ester (6). To the best of our knowledge, compound 6 is herein reported by the first time in the literature. These compounds were assayed for acetylcholinesterase inhibition along with some related compounds. Compound 6 showed the highest acetylcholinesterase inhibitory activity at 10000 µg/mL among the tested compounds, a result (92.89%) comparable to the activity of the positive control, galanthamine (94.21%). Therefore, biotransformation of the natural product 1 by M. plumbeus produced a novel compound with potential as a new lead to develop anti-Alzheimer medicines.
NCBI PubMed ID: 29069140Publication DOI: 10.1590/0001-3765201720170240Journal NLM ID: 7503280Publisher: Academia Brasileira De Ciencias
Correspondence: jat@qui.ufmg.br
Institutions: Departamento de Química, Instituto de Ciências Exatas, Universidade Federal de Minas Gerais, Pampulha, Brazil
Methods: 13C NMR, 1H NMR, IR, HMBC, COSY, NOESY, HSQC, HRMS
Found