ABSTRACT
Nine compounds were isolated from the leaves of Eugenia catharinae, namely monomethyl olivetol (1), ß-sitosterol (2), stigmasterol (3), uvaol (4), erythrodiol (5), rotundic acid (6), quercetin (7), catechin (8) and myricitrin (9). The structures of 1-9 were established through analysis of their spectroscopic (1H and 13C NMR) and spectrometric (MS) data. Compounds 1 and 6 are reported the first time in the Eugenia genus. In addition, these data were compared with those reported in the literature. The antioxidant activity of plant samples and compounds was measured using the DPPH radical scavenging assay. Flavonoids 7, 8, 9 and the ethanolic extract showed the best results, with IC50 values of 20.94 µM, 44.20 µM, 30.01 µM and 58.82 µg/mL, respectively.
ABSTRACT
Type 2 diabetes (T2D) is an endocrine metabolic disease with a worldwide prevalence of more than 8%, and an expected increase close to 50% in the next 15-20years. T2D is associated with severe and life-threatening complications like retinopathy, neuropathy, nephropathy, and cardiovascular diseases, and therefore improved drug leads or functional foods containing α-glucosidase inhibitors are needed for management of blood glucose. In this study, leaves of Myrcia palustris were investigated by high-resolution α-glucosidase inhibition profiling combined with HPLC-HRMS-SPE-NMR. This led to identification of casuarinin, myricetin 3-O-ß-d-(6â³-galloyl)galactopyranoside, kaempferol 3-O-ß-d-galactopyranoside, myricetin, and quercetin as α-glucosidase inhibitors. In addition, four acetylated ellagic acid rhamnosides, i.e., 4-O-(2â³,4â³-O-diacetyl-α-l-rhamnopyranosyl)ellagic acid, 4-O-(2â³,3â³-O-diacetyl-α-l-rhamnopyranosyl)ellagic acid, 4-O-(3â³,4â³-O-diacetyl-α-l-rhamnopyranosyl)ellagic acid, and 4-O-(2â³,3â³,4â³-O-triacetyl-α-l-rhamnopyranosyl)ellagic acid were identified.
Subject(s)
Ellagic Acid/isolation & purification , Ellagic Acid/pharmacology , Glycoside Hydrolase Inhibitors/isolation & purification , Glycoside Hydrolase Inhibitors/pharmacology , Glycosides/isolation & purification , Glycosides/pharmacology , Hypoglycemic Agents/isolation & purification , Hypoglycemic Agents/pharmacology , Myrtaceae/chemistry , Chromatography, High Pressure Liquid , Diabetes Mellitus, Type 2/drug therapy , Ellagic Acid/chemistry , Flavonoids/chemistry , Flavonoids/isolation & purification , Flavonoids/pharmacology , Glycoside Hydrolase Inhibitors/chemistry , Glycosides/chemistry , Humans , Hypoglycemic Agents/chemistry , Kaempferols/chemistry , Kaempferols/isolation & purification , Kaempferols/pharmacology , Molecular Structure , Nuclear Magnetic Resonance, Biomolecular , Plant Leaves/chemistry , Quercetin/analysis , alpha-Glucosidases/drug effectsABSTRACT
The liquid-liquid partitioning of a crude hydroalcoholic extract of Averrhoa carambola L., Oxalidaceae, leaves led to the isolation of a sterol and three flavone C-glycosides. From the n-hexane fraction β-sitosterol was isolated and from the ethyl acetate fraction apigenin-6-C-β-L-fucopyranoside (1) and apigenin6-C-(2"-O-α-L-rhamnopyranosyl)-β-L-fucopyranoside (2) were obtained. Apigenin6-C-(2"-O-α-L-rhamnopyranosyl)-β-D-glucopyranoside (3) was isolated from the n-butanol fraction. Compound 3 is new, while 1 and 2 have been previously isolated from A. carambola. The antioxidant activity was measured using the DPPH radical scavenging assay and reducing power of iron (III) to iron (II) ions. The ethyl acetate and n-butanol fractions showed the most antioxidant activity. As evaluated by ability of the sample to scavenge DPPH the IC50 values were 90.92 and 124.48 µg/ mL, respectively. In the assay of reducing power these fractions presented 135.64 and 125.12 of ascorbic acid equivalents, respectively. The antioxidant activity exhibited a significant relationship with the phenolic content (r² = 0.997), but a poor relationship with the flavonoids content (r² = 0.424). The n-hexane fraction was the only fraction to present good toxicity using A. salina with LC50 800.2 µg/mL.
