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 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.

Assessment of Residual Solvent and Drug in PLGA Microspheres by Derivative Thermogravimetry

“…DTG makes it possible to obtain parameters related to a thermal event, such as its onset and end temperatures (To and Te), as well as the temperature at which the rate of mass change is highest (Tp). DTG has been used for thermal decomposition studies of various materials such as carbon spheres, polyaniline-cellulose nanofiber, laterite, and amyrenone [16][17][18][19]. DTG was also used to analyze the composition ratio of a polymer composite.…”

In Silico Study, Physicochemical, and In Vitro Lipase Inhibitory Activity of α,β-Amyrenone Inclusion Complexes with Cyclodextrins

“…α , β -Amyrenones (ABAME) are triterpenoid isomers of the ursan and oleanan series that occur naturally in low concentrations in various oleoresins of Protium (Burseraceae) species widespread in the Brazilian Amazon or can be obtained by the oxidation of α , β -amyrin isolated from the oleoresin mainly of Protium heptaphyllum [ 1 ].…”

“…Although ABAME and compounds of the same class have a wide range of proven biological activities, they present in its crystalline state unfavorable physicochemical characteristics for pharmaceutical applications such as a poor solubility in water, which can reduce their bioavailability [ 1 ].…”

“…Oral administration of ABAME in mice resulted in a reduction in mechanical hypersensitivity and carrageenan-induced paw and ear edema; in addition, inhibition of nitric oxide and interleukin 6 (IL-6) production and increased synthesis of IL-10 in lipopolysaccharide-stimulated murine J774 macrophages were observed [ 1 ]. In addition, the triterpene extract of Cnidoscolus chayamansa containing β -amyrenone showed significant anti-inflammatory activity [ 2 ].…”

“…Hypoglycemic and hypolipemic actions of P. heptaphyllum oleoresin triterpenes have been previously reported [ 3 , 4 ]. ABAME has already been described as having potential in the treatment of chronic and metabolic diseases because it displayed inhibitory effects in vitro on lipase, α -glucosidase, and α -amylase [ 1 , 5 ]; therefore, it is necessary to evaluate its hypoglycemic activity and the mechanisms of action involved in this activity [ 6 ]. Thus, a methodology similar to that of current studies on antidiabetic and anti-obesity action was followed, focusing on the activity of the mixture against digestive enzymes involved in the metabolism of lipids and glycides.…”