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

Rosilene Ferreira,Valdir Veiga Junior,Ádley Lima,Emerson Lima,Walter Silva Júnior

doi:10.3390/molecules22020298

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.

Highlights

The binary compound α,β-amyrenone is a triterpenic derivative of the ursane and oleanane series commonly described in isolation studies from Burseraceae family species such as Protium heptaphyllum, P. opacum var. opacum, and P. giganteum; Trattinnickia glaziovii and T. peruviana [1,2]
The α,β-amyrenone was obtained obtained by oxidation oxidation of α,β-amyrin α,β-amyrin isolated isolated from Protium reaction yield on based onα,β-amyrin
Amyrin extraction: Amyrin was isolated from the commercial oleoresin and its isolation was performed by normal phase column chromatography

Summary

Introduction

The binary compound α,β-amyrenone is a triterpenic derivative of the ursane and oleanane series commonly described in isolation studies from Burseraceae family species such as Protium heptaphyllum, P. opacum var. opacum, and P. giganteum; Trattinnickia glaziovii and T. peruviana [1,2]. The binary compound α,β-amyrenone is a triterpenic derivative of the ursane and oleanane series commonly described in isolation studies from Burseraceae family species such as Protium heptaphyllum, P. opacum var. There are other sources in which α,β-amyrenone was identified such as: Cissus quadrangulares, Tridax procumbens, Camellia sinensis var. Pistacia lentiscus (resin, found in archaeological remains); Beilschmiedia sp.; Anacolosa pervilleana; archaeological remains); Ficus microcarpa; Ficus pandurata and. Ficus pandurata and Cyclocarpa paliurus [3,4,5,6,7,8]. Cyclocarpa paliurus [3,4,5,6,7,8]. Previous studies studiesusing using α,β-amyrenone demonstrated its pharmacological potential.

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