Structural Characterization and In Vitro and In Silico Studies on the Anti-<i>α</i>-Glucosidase Activity of Anacardic Acids from <i>Anacardium occidentale</i>
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...
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2024-12-01
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| author | Ana Priscila Monteiro da Silva Gisele Silvestre da Silva Francisco Oiram Filho Maria Francilene Souza Silva Guilherme Julião Zocolo Edy Sousa de Brito |
| author_facet | Ana Priscila Monteiro da Silva Gisele Silvestre da Silva Francisco Oiram Filho Maria Francilene Souza Silva Guilherme Julião Zocolo Edy Sousa de Brito |
| author_sort | Ana Priscila Monteiro da Silva |
| collection | DOAJ |
| description | 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 <i>α</i>-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<sub>50</sub> = 1.78 ± 0.08 μg mL<sup>−1</sup>), followed by AAn2 (1.99 ± 0.76 μg mL<sup>−1</sup>), AAn3 (3.31 ± 0.03 μg mL<sup>−1</sup>), and the mixture (3.72 ± 2.11 μg mL<sup>−1</sup>). All AAs significantly outperformed acarbose (IC<sub>50</sub> = 169.3 μg mL<sup>−1</sup>). 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. |
| format | Article |
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| issn | 2304-8158 |
| language | English |
| publishDate | 2024-12-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Foods |
| spelling | doaj-art-fa8db345be024eebac97200ddada3e682025-08-20T02:00:27ZengMDPI AGFoods2304-81582024-12-011324410710.3390/foods13244107Structural Characterization and In Vitro and In Silico Studies on the Anti-<i>α</i>-Glucosidase Activity of Anacardic Acids from <i>Anacardium occidentale</i>Ana Priscila Monteiro da Silva0Gisele Silvestre da Silva1Francisco Oiram Filho2Maria Francilene Souza Silva3Guilherme Julião Zocolo4Edy Sousa de Brito5Embrapa Agroindústria Tropical, Fortaleza 60511-110, CE, BrazilEmbrapa Agroindústria Tropical, Fortaleza 60511-110, CE, BrazilEmbrapa Agroindústria Tropical, Fortaleza 60511-110, CE, BrazilResearch and Development of Medicines, Federal University of Ceará, Rua Coronel Nunes de Melo 1000, Rodolfo Teófilo, Fortaleza 60420-275, CE, BrazilEmbrapa Agroindústria Tropical, Fortaleza 60511-110, CE, BrazilEmbrapa Alimentos e Territórios, Maceió 57020-050, AL, BrazilThe 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 <i>α</i>-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<sub>50</sub> = 1.78 ± 0.08 μg mL<sup>−1</sup>), followed by AAn2 (1.99 ± 0.76 μg mL<sup>−1</sup>), AAn3 (3.31 ± 0.03 μg mL<sup>−1</sup>), and the mixture (3.72 ± 2.11 μg mL<sup>−1</sup>). All AAs significantly outperformed acarbose (IC<sub>50</sub> = 169.3 μg mL<sup>−1</sup>). 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.https://www.mdpi.com/2304-8158/13/24/4107antidiabetic compoundsanacardic acidalkyl phenol<i>α</i>-glucosidase inhibitionmolecular dockingpharmacokinetic properties |
| spellingShingle | Ana Priscila Monteiro da Silva Gisele Silvestre da Silva Francisco Oiram Filho Maria Francilene Souza Silva Guilherme Julião Zocolo Edy Sousa de Brito Structural Characterization and In Vitro and In Silico Studies on the Anti-<i>α</i>-Glucosidase Activity of Anacardic Acids from <i>Anacardium occidentale</i> Foods antidiabetic compounds anacardic acid alkyl phenol <i>α</i>-glucosidase inhibition molecular docking pharmacokinetic properties |
| title | Structural Characterization and In Vitro and In Silico Studies on the Anti-<i>α</i>-Glucosidase Activity of Anacardic Acids from <i>Anacardium occidentale</i> |
| title_full | Structural Characterization and In Vitro and In Silico Studies on the Anti-<i>α</i>-Glucosidase Activity of Anacardic Acids from <i>Anacardium occidentale</i> |
| title_fullStr | Structural Characterization and In Vitro and In Silico Studies on the Anti-<i>α</i>-Glucosidase Activity of Anacardic Acids from <i>Anacardium occidentale</i> |
| title_full_unstemmed | Structural Characterization and In Vitro and In Silico Studies on the Anti-<i>α</i>-Glucosidase Activity of Anacardic Acids from <i>Anacardium occidentale</i> |
| title_short | Structural Characterization and In Vitro and In Silico Studies on the Anti-<i>α</i>-Glucosidase Activity of Anacardic Acids from <i>Anacardium occidentale</i> |
| title_sort | structural characterization and in vitro and in silico studies on the anti i α i glucosidase activity of anacardic acids from i anacardium occidentale i |
| topic | antidiabetic compounds anacardic acid alkyl phenol <i>α</i>-glucosidase inhibition molecular docking pharmacokinetic properties |
| url | https://www.mdpi.com/2304-8158/13/24/4107 |
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