Structural Characterization and In Vitro and In Silico Studies on the Anti- α -Glucosidase Activity of Anacardic Acids from Anacardium occidentale

• Published in: Foods 2024-12, Vol.13 (24), p.4107
• Main Authors: Silva, Ana Priscila Monteiro da, Silva, Gisele Silvestre da, Oiram Filho, Francisco, Silva, Maria Francilene Souza, Zocolo, Guilherme Julião, Brito, Edy Sousa de
• Format: Article
• Language: English
• Subjects: Acarbose; Acids; alkyl phenol; Amino acids; anacardic acid; antidiabetic compounds; Aromatic compounds; Chemical properties; Chromatography; Diabetes; Diabetes mellitus; Diabetes therapy; Enzymes; Gas flow; Glucosidase; Hydrolases; Hypoglycemic agents; Magnetic resonance spectroscopy; Medical research; Metabolic syndrome; Metabolites; Mixtures; molecular docking; Natural resources; NMR; NMR spectroscopy; Nuclear magnetic resonance; Nuclear magnetic resonance spectroscopy; pharmacokinetic properties; Pharmacokinetics; Structural analysis; Sustainable use; Toxicity; Type 2 diabetes; United States; α-Glucosidase; α-glucosidase inhibition
• ISSN: 2304-8158; 2304-8158
• DOI: 10.3390/foods13244107

The growing focus on sustainable use of natural resources has brought attention to cashew nut shell liquid (CNSL), a by-product rich in anacardic acids (AAs) with potential applications in diabetes treatment. In this study, three different AAs from CNSL, monoene (15:1, AAn1), diene (15:2, AAn2), and triene (15:3, AAn3), and a mixture of the three (mix) were evaluated as -glucosidase inhibitors. The samples were characterized by combining 1D and 2D NMR spectroscopy, along with ESI-MS. In vitro assays revealed that AAn1 had the strongest inhibitory effect (IC = 1.78 ± 0.08 μg mL ), followed by AAn2 (1.99 ± 0.76 μg mL ), AAn3 (3.31 ± 0.03 μg mL ), and the mixture (3.72 ± 2.11 μg mL ). All AAs significantly outperformed acarbose (IC = 169.3 μg mL ). In silico docking suggested that polar groups on the aromatic ring are key for enzyme-ligand binding. The double bond at C15, while not essential, enhanced the inhibitory effects. Toxicity predictions classified AAs as category IV, and pharmacokinetic analysis suggested moderately favorable drug-like properties. These findings highlight AAs as a promising option in the search for new hypoglycemic compounds.