New Dibenzo-<i>α</i>-pyrone Derivatives with <i>α</i>-Glucosidase Inhibitory Activities from the Marine-Derived Fungus <i>Alternaria alternata</i>
Three new dibenzo-<i>α</i>-pyrone derivatives, alternolides A–C (<b>1</b>–<b>3</b>), and seven known congeners (<b>4</b>–<b>10</b>) were isolated from the marine-derived fungus of <i>Alternaria alternata</i> LW37 assisted by the...
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| Format: | Article |
| Language: | English |
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MDPI AG
2022-12-01
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| Series: | Marine Drugs |
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| Online Access: | https://www.mdpi.com/1660-3397/20/12/778 |
| _version_ | 1797456570362101760 |
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| author | Jinxin Zhang Baodan Zhang Lei Cai Ling Liu |
| author_facet | Jinxin Zhang Baodan Zhang Lei Cai Ling Liu |
| author_sort | Jinxin Zhang |
| collection | DOAJ |
| description | Three new dibenzo-<i>α</i>-pyrone derivatives, alternolides A–C (<b>1</b>–<b>3</b>), and seven known congeners (<b>4</b>–<b>10</b>) were isolated from the marine-derived fungus of <i>Alternaria alternata</i> LW37 assisted by the one strain-many compounds (OSMAC) strategy. The structures of <b>1</b>–<b>3</b> were established by extensive spectroscopic analyses, and their absolute configurations were determined by modified Snatzke′s method and electronic circular dichroism (ECD) calculations. Compounds <b>6</b> and <b>7</b> showed good 1,1-diphenyl-2-picrylhydrazyl (DPPH) antioxidant scavenging activities with IC<sub>50</sub> values of 83.94 ± 4.14 and 23.60 ± 1.23 µM, respectively. Additionally, <b>2</b>, <b>3</b> and <b>7</b> exhibited inhibitory effects against <i>α</i>-glucosidase with IC<sub>50</sub> values of 725.85 ± 4.75, 451.25 ± 6.95 and 6.27 ± 0.68 µM, respectively. The enzyme kinetics study indicated <b>2</b> and <b>3</b> were mixed-type inhibitors of <i>α</i>-glucosidase with <i>K</i><sub>i</sub> values of 347.0 and 108.5 µM, respectively. Furthermore, the interactions of <b>2</b>, <b>3</b> and <b>7</b> with <i>α</i>-glucosidase were investigated by molecular docking. |
| first_indexed | 2024-03-09T16:09:43Z |
| format | Article |
| id | doaj.art-12f5fa88e1264acb9c7dfc59fd65be15 |
| institution | Directory Open Access Journal |
| issn | 1660-3397 |
| language | English |
| last_indexed | 2024-03-09T16:09:43Z |
| publishDate | 2022-12-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Marine Drugs |
| spelling | doaj.art-12f5fa88e1264acb9c7dfc59fd65be152023-11-24T16:20:02ZengMDPI AGMarine Drugs1660-33972022-12-01201277810.3390/md20120778New Dibenzo-<i>α</i>-pyrone Derivatives with <i>α</i>-Glucosidase Inhibitory Activities from the Marine-Derived Fungus <i>Alternaria alternata</i>Jinxin Zhang0Baodan Zhang1Lei Cai2Ling Liu3State Key Laboratory of Mycology, Institute of Microbiology, Chinese Academy of Sciences, Beijing 100101, ChinaState Key Laboratory of Mycology, Institute of Microbiology, Chinese Academy of Sciences, Beijing 100101, ChinaState Key Laboratory of Mycology, Institute of Microbiology, Chinese Academy of Sciences, Beijing 100101, ChinaState Key Laboratory of Mycology, Institute of Microbiology, Chinese Academy of Sciences, Beijing 100101, ChinaThree new dibenzo-<i>α</i>-pyrone derivatives, alternolides A–C (<b>1</b>–<b>3</b>), and seven known congeners (<b>4</b>–<b>10</b>) were isolated from the marine-derived fungus of <i>Alternaria alternata</i> LW37 assisted by the one strain-many compounds (OSMAC) strategy. The structures of <b>1</b>–<b>3</b> were established by extensive spectroscopic analyses, and their absolute configurations were determined by modified Snatzke′s method and electronic circular dichroism (ECD) calculations. Compounds <b>6</b> and <b>7</b> showed good 1,1-diphenyl-2-picrylhydrazyl (DPPH) antioxidant scavenging activities with IC<sub>50</sub> values of 83.94 ± 4.14 and 23.60 ± 1.23 µM, respectively. Additionally, <b>2</b>, <b>3</b> and <b>7</b> exhibited inhibitory effects against <i>α</i>-glucosidase with IC<sub>50</sub> values of 725.85 ± 4.75, 451.25 ± 6.95 and 6.27 ± 0.68 µM, respectively. The enzyme kinetics study indicated <b>2</b> and <b>3</b> were mixed-type inhibitors of <i>α</i>-glucosidase with <i>K</i><sub>i</sub> values of 347.0 and 108.5 µM, respectively. Furthermore, the interactions of <b>2</b>, <b>3</b> and <b>7</b> with <i>α</i>-glucosidase were investigated by molecular docking.https://www.mdpi.com/1660-3397/20/12/778marine-derived fungus<i>Alternaria alternata</i>OSMACdibenzo-<i>α</i>-pyronebiological activitiesantioxidant |
| spellingShingle | Jinxin Zhang Baodan Zhang Lei Cai Ling Liu New Dibenzo-<i>α</i>-pyrone Derivatives with <i>α</i>-Glucosidase Inhibitory Activities from the Marine-Derived Fungus <i>Alternaria alternata</i> Marine Drugs marine-derived fungus <i>Alternaria alternata</i> OSMAC dibenzo-<i>α</i>-pyrone biological activities antioxidant |
| title | New Dibenzo-<i>α</i>-pyrone Derivatives with <i>α</i>-Glucosidase Inhibitory Activities from the Marine-Derived Fungus <i>Alternaria alternata</i> |
| title_full | New Dibenzo-<i>α</i>-pyrone Derivatives with <i>α</i>-Glucosidase Inhibitory Activities from the Marine-Derived Fungus <i>Alternaria alternata</i> |
| title_fullStr | New Dibenzo-<i>α</i>-pyrone Derivatives with <i>α</i>-Glucosidase Inhibitory Activities from the Marine-Derived Fungus <i>Alternaria alternata</i> |
| title_full_unstemmed | New Dibenzo-<i>α</i>-pyrone Derivatives with <i>α</i>-Glucosidase Inhibitory Activities from the Marine-Derived Fungus <i>Alternaria alternata</i> |
| title_short | New Dibenzo-<i>α</i>-pyrone Derivatives with <i>α</i>-Glucosidase Inhibitory Activities from the Marine-Derived Fungus <i>Alternaria alternata</i> |
| title_sort | new dibenzo i α i pyrone derivatives with i α i glucosidase inhibitory activities from the marine derived fungus i alternaria alternata i |
| topic | marine-derived fungus <i>Alternaria alternata</i> OSMAC dibenzo-<i>α</i>-pyrone biological activities antioxidant |
| url | https://www.mdpi.com/1660-3397/20/12/778 |
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