Ferreira Rosilene G S, Silva Júnior Walter F, Veiga Junior Valdir F, Lima Ádley A N, Lima Emerson S
Higher Normal School, University of the State of Amazonas, Av. Djalma Batista 69050-010, Brazil.
Laboratory of Biological Activity, Faculty of Pharmaceutical Sciences, Federal University of Amazonas, Av. General Rodrigo Otávio, 69077-000-Manaus-AM, Brazil.
Molecules. 2017 Feb 16;22(2):298. doi: 10.3390/molecules22020298.
α-Amyrenone and β-amyrenone are triterpenoid isomers that occur naturally in very low concentrations in several oleoresins from Brazilian Amazon species of (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 C), 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 (IC) 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 IC 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.
α-香树脂酮和β-香树脂酮是三萜类异构体，在巴西亚马逊地区几种橄榄科植物的油树脂中天然存在，浓度极低。这种混合物也可以通过氧化α,β-香树素合成，α,β-香树素是从相同油树脂中获得的主要化合物。采用非常简单、高产率的方法，以市售的α,β-香树素混合物为底物，合成了二元化合物α,β-香树脂酮，并使用高效液相色谱、核磁共振（¹H和¹³C）、质谱、扫描电子显微镜、差示扫描量热法、热重分析法和微商热重分析法以及傅里叶变换红外光谱（FTIR）等不同技术对其进行了物理化学表征。还通过研究参与碳水化合物和脂质吸收过程的酶的抑制作用来评估其生物学效应，例如α-淀粉酶、α-葡萄糖苷酶、脂肪酶，并测定了它们50%活性的抑制浓度值（IC）。α,β-香树脂酮在浓度为1.6 g/mL时显著抑制α-葡萄糖苷酶（96.5% ± 0.52%）。α,β-香树脂酮在浓度为100 µg/mL时对脂肪酶的抑制率为82.99% ± 1.51%，IC值为该浓度。因此，这些物质在体外对脂肪酶、α-葡萄糖苷酶和α-淀粉酶显示出抑制作用。这些发现证明了α,β-香树脂酮在开发治疗慢性代谢疾病药物方面的潜力。
