Novel Antioxidants and <i>α</i>-Glycosidase and Protein Tyrosine Phosphatase 1B Inhibitors from an Endophytic Fungus <i>Penicillium brefeldianum</i> F4a
Oxidative stress plays a very important role in the progression of diabetes and its complications. A therapeutic agent that is both antidiabetic and antioxidant would be the preferred choice for the treatment of diabetes. The crude extract of the endophytic fungus <i>Penicillium brefeldianum&l...
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| Autores principales: | , , , , |
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| Formato: | article |
| Lenguaje: | EN |
| Publicado: |
MDPI AG
2021
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| Materias: | |
| Acceso en línea: | https://doaj.org/article/d959537686c9450b9d52110b8ba4f2a5 |
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| Sumario: | Oxidative stress plays a very important role in the progression of diabetes and its complications. A therapeutic agent that is both antidiabetic and antioxidant would be the preferred choice for the treatment of diabetes. The crude extract of the endophytic fungus <i>Penicillium brefeldianum</i> F4a has significant antioxidant and <i>α</i>-glycosidase and protein tyrosine phosphatase 1B (PTP1B) inhibition activities. Chemical investigation of <i>P. brefeldianum</i> F4a using an activity-guided isolation led to the discovery of three new compounds called peniorcinols A–C (<b>1</b>–<b>3</b>) along with six known compounds: penialidins A (<b>4</b>), penialidin F (<b>5</b>), myxotrichin C (<b>6</b>), riboflavin (<b>7</b>), indole-3-acetic acid (<b>8</b>), and 2-(4-hydroxy-2-methoxy-6-methylphenyl) acetic acid (<b>9</b>). Their chemical structures were established by their NMR and HRESIMS. The absolute configurations of <b>1</b> and <b>3</b> were determined by experimental and calculated electronic circular dichroism (ECD). Their antioxidant activities were evaluated by DPPH<sup>•</sup> and ABTS<sup>•+</sup> scavenging assays. Compounds <b>1</b>–<b>6</b> and <b>8</b>–<b>9</b> showed moderate to strong free radical scavenging activities. Significantly, <b>4</b>–<b>6</b> exhibited more potent ABTS<sup>•+</sup> scavenging activity than that of the positive control. Their <i>α</i>-glycosidase and PTP1B inhibition activities were tested. Among them, compound <b>3</b> showed α-glucosidase inhibition activity, and compounds <b>7</b> and <b>8</b> showed PTP1B inhibitory activity for the first time. It is worth noting that <b>3</b> and <b>8</b> displayed both antioxidant and <i>α</i>-glycosidase or PTP1B inhibition activities. These finding suggest that compounds <b>3</b> and <b>8</b> could be used as lead compounds to generate new potent drugs for the treatment of oxidative stress-related diabetes. |
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