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Molecules 2017, 22(2), 298; doi:10.3390/molecules22020298

Physicochemical Characterization and Biological Activities of the Triterpenic Mixture α,β-Amyrenone

1
Higher Normal School, University of the State of Amazonas, Av. Djalma Batista 69050-010, Brazil
2
Laboratory of Biological Activity, Faculty of Pharmaceutical Sciences, Federal University of Amazonas, Av. General Rodrigo Otávio, 69077-000-Manaus-AM, Brazil
3
Department of Pharmacy, Federal University of Rio Grande do Norte, Av. Coronel Gustavo Cordeiro de Farias s/n, 59012-570-Natal-RN, Brazil
4
Laboratory of Chemistry of Amazonian Biomolecules, Department of Chemistry, Federal University of Amazonas, Av. General Rodrigo Otávio, Manaus, AM 69077-000, Brazil
*
Author to whom correspondence should be addressed.
Academic Editor: Fernando Albericio
Received: 18 January 2017 / Revised: 3 February 2017 / Accepted: 8 February 2017 / Published: 16 February 2017
(This article belongs to the Section Natural Products)
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Abstract

α-Amyrenone and β-amyrenone are triterpenoid isomers that occur naturally in very low concentrations in several oleoresins from Brazilian Amazon species of Protium (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 and 13C), 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 IC50 value 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. View Full-Text
Keywords: enzymatic activity; triterpenes; Protium; amyrin; amyrenone enzymatic activity; triterpenes; Protium; amyrin; amyrenone
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MDPI and ACS Style

Ferreira, R.G.S.; Silva Júnior, W.F.; Veiga Junior, V.F.; Lima, Á.A.N.; Lima, E.S. Physicochemical Characterization and Biological Activities of the Triterpenic Mixture α,β-Amyrenone. Molecules 2017, 22, 298.

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