Novel Antioxidants and α-Glycosidase and Protein Tyrosine Phosphatase 1B Inhibitors from an Endophytic Fungus Penicillium brefeldianum 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 Penicillium brefeldianum&l...

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Auteurs principaux:	Yan Bai, Ping Yi, Songya Zhang, Jiangchun Hu, Huaqi Pan
Format:	article
Langue:	EN
Publié:	MDPI AG 2021
Sujets:	endophyte peniorcinol DPPH<sup>•</sup> scavenging activity ABTS<sup>•+</sup> scavenging activity <i>α</i>-glycosidase inhibitory activity protein tyrosine phosphatase 1B (PTP1B) inhibitory activity Biology (General) QH301-705.5
Accès en ligne:	https://doaj.org/article/d959537686c9450b9d52110b8ba4f2a5
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spelling	oai:doaj.org-article:d959537686c9450b9d52110b8ba4f2a52021-11-25T18:05:40ZNovel Antioxidants and <i>α</i>-Glycosidase and Protein Tyrosine Phosphatase 1B Inhibitors from an Endophytic Fungus <i>Penicillium brefeldianum</i> F4a10.3390/jof71109132309-608Xhttps://doaj.org/article/d959537686c9450b9d52110b8ba4f2a52021-10-01T00:00:00Zhttps://www.mdpi.com/2309-608X/7/11/913https://doaj.org/toc/2309-608XOxidative 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.Yan BaiPing YiSongya ZhangJiangchun HuHuaqi PanMDPI AGarticleendophytepeniorcinolDPPH<sup>•</sup> scavenging activityABTS<sup>•+</sup> scavenging activity<i>α</i>-glycosidase inhibitory activityprotein tyrosine phosphatase 1B (PTP1B) inhibitory activityBiology (General)QH301-705.5ENJournal of Fungi, Vol 7, Iss 913, p 913 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	endophyte peniorcinol DPPH<sup>•</sup> scavenging activity ABTS<sup>•+</sup> scavenging activity <i>α</i>-glycosidase inhibitory activity protein tyrosine phosphatase 1B (PTP1B) inhibitory activity Biology (General) QH301-705.5
spellingShingle	endophyte peniorcinol DPPH<sup>•</sup> scavenging activity ABTS<sup>•+</sup> scavenging activity <i>α</i>-glycosidase inhibitory activity protein tyrosine phosphatase 1B (PTP1B) inhibitory activity Biology (General) QH301-705.5 Yan Bai Ping Yi Songya Zhang Jiangchun Hu Huaqi Pan Novel Antioxidants and <i>α</i>-Glycosidase and Protein Tyrosine Phosphatase 1B Inhibitors from an Endophytic Fungus <i>Penicillium brefeldianum</i> F4a
description	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.
format	article
author	Yan Bai Ping Yi Songya Zhang Jiangchun Hu Huaqi Pan
author_facet	Yan Bai Ping Yi Songya Zhang Jiangchun Hu Huaqi Pan
author_sort	Yan Bai
title	Novel Antioxidants and <i>α</i>-Glycosidase and Protein Tyrosine Phosphatase 1B Inhibitors from an Endophytic Fungus <i>Penicillium brefeldianum</i> F4a
title_short	Novel Antioxidants and <i>α</i>-Glycosidase and Protein Tyrosine Phosphatase 1B Inhibitors from an Endophytic Fungus <i>Penicillium brefeldianum</i> F4a
title_full	Novel Antioxidants and <i>α</i>-Glycosidase and Protein Tyrosine Phosphatase 1B Inhibitors from an Endophytic Fungus <i>Penicillium brefeldianum</i> F4a
title_fullStr	Novel Antioxidants and <i>α</i>-Glycosidase and Protein Tyrosine Phosphatase 1B Inhibitors from an Endophytic Fungus <i>Penicillium brefeldianum</i> F4a
title_full_unstemmed	Novel Antioxidants and <i>α</i>-Glycosidase and Protein Tyrosine Phosphatase 1B Inhibitors from an Endophytic Fungus <i>Penicillium brefeldianum</i> F4a
title_sort	novel antioxidants and <i>α</i>-glycosidase and protein tyrosine phosphatase 1b inhibitors from an endophytic fungus <i>penicillium brefeldianum</i> f4a
publisher	MDPI AG
publishDate	2021
url	https://doaj.org/article/d959537686c9450b9d52110b8ba4f2a5
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Novel Antioxidants and <i>α</i>-Glycosidase and Protein Tyrosine Phosphatase 1B Inhibitors from an Endophytic Fungus <i>Penicillium brefeldianum</i> F4a

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