title: Physicochemical Characterization and Biological Activities of the Triterpenic Mixture α,β-Amyrenone.
abstract: α-Amyrenone and β-amyrenone are triterpenoid isomers that occur naturally in very low concentrations in several oleoresins from Brazilian Amazon species ofProtium(Burseraceae). This mixture can also be synthesized by oxidation of α,β-amyrins, obtained as major compounds from the same oleoresins. Using a very simple, high yield procedure, and using a readily commercially available mixture of α,β-amyrins as substrate, the binary compound α,β-amyrenone was synthesized and submitted to physico-chemical characterization using different techniques such as high-performance liquid chromatography, nuclear magnetic resonance (¹H and13C), mass spectrometry, scanning electron microscopy, differential scanning calorimetry, thermogravimetry and derivative thermogravimetry, and Fourier transform infrared spectroscopy (FTIR). Biological effects were also evaluated by studying the inhibition of enzymes involved in the carbohydrate and lipid absorption process, such as α-amylase, α-glucosidase, lipase, and their inhibitory concentration values of 50% of activity (IC50) were also determined. α,β-Amyrenone significantly inhibited α-glucosidase (96.5% ± 0.52%) at a concentration of 1.6 g/mL. α,β-Amyrenone, at a concentration of 100 µg/mL, showed an inhibition rate on lipase with an IC50value of 82.99% ± 1.51%. The substances have thus shown in vitro inhibitory effects on the enzymes lipase, α-glucosidase, and α-amylase. These findings demonstrate the potential of α,β-amyrenone for the development of drugs in the treatment of chronic metabolic diseases.
authors.affiliation: Higher Normal School, University of the State of Amazonas, Av. Djalma Batista 69050-010, Brazil. rgsilva@uea.edu.br.|Laboratory of Biological Activity, Faculty of Pharmaceutical Sciences, Federal University of Amazonas, Av. General Rodrigo Otávio, 69077-000-Manaus-AM, Brazil. rgsilva@uea.edu.br.
authors.forename: Rosilene G S
authors.initials: RG
authors.lastname: Ferreira
authors.affiliation: Department of Pharmacy, Federal University of Rio Grande do Norte, Av. Coronel Gustavo Cordeiro de Farias s/n, 59012-570-Natal-RN, Brazil. walterjuniornt@hotmail.com.
authors.forename: Walter F
authors.initials: WF
authors.lastname: Silva Júnior
authors.affiliation: Laboratory of Chemistry of Amazonian Biomolecules, Department of Chemistry, Federal University of Amazonas, Av. General Rodrigo Otávio, Manaus, AM 69077-000, Brazil. valdir.veiga@gmail.com.
authors.forename: Valdir F
authors.initials: VF
authors.lastname: Veiga Junior
authors.affiliation: Department of Pharmacy, Federal University of Rio Grande do Norte, Av. Coronel Gustavo Cordeiro de Farias s/n, 59012-570-Natal-RN, Brazil. adleyantonini@yahoo.com.br.
authors.forename: Ádley A N
authors.initials: ÁA
authors.lastname: Lima
authors.affiliation: Laboratory of Biological Activity, Faculty of Pharmaceutical Sciences, Federal University of Amazonas, Av. General Rodrigo Otávio, 69077-000-Manaus-AM, Brazil. eslima@ufam.edu.br.
authors.forename: Emerson S
authors.initials: ES
authors.lastname: Lima
mesh_terms: D029403:Burseraceae / Q000737:chemistry; D002152:Calorimetry, Differential Scanning; D002851:Chromatography, High Pressure Liquid; D004791:Enzyme Inhibitors / Q000737:chemistry / Q000494:pharmacology; D010084:Oxidation-Reduction; D013818:Thermogravimetry; D014315:Triterpenes / Q000737:chemistry* / Q000494:pharmacology*; D014961:X-Ray Diffraction
chemical_list: D004791:Enzyme Inhibitors; D014315:Triterpenes; C073947:alpha-amyrenone
keywords: Protium; amyrenone; amyrin; enzymatic activity; triterpenes