{"title":"作为α-葡萄糖苷酶抑制剂的 2β-Acetoxyferruginol 衍生物：合成与生物学评价","authors":"","doi":"10.1016/j.bioorg.2024.107770","DOIUrl":null,"url":null,"abstract":"<div><p>To find potential α-glucosidase inhibitors, a series of 2β-acetoxyferuginol derivatives containing cinnamic acid (<strong>WXC-1 ∼ 25</strong>) were synthesized and investigated their biological activity. All derivatives (<strong>WXC-1 ∼ 25</strong>) displayed better inhibitory activity (IC<sub>50</sub> values: 7.56 ± 1.35 ∼ 25.63 ± 1.72 μM) compared to acarbose (IC<sub>50</sub> vaule: 564.28 ± 48.68 μM). In particularly, <strong>WXC-25</strong> with 4-hydroxycinnamic acid section showed the best inhibitory activity (IC<sub>50</sub> vaule: 2.02 ± 0.14 μM), ∼75-fold stronger than acarbose. Kinetics results suggested <strong>WXC-25</strong> being one reversible non-competition inhibitors. Fluorescence quenching results indicated that <strong>WXC-25</strong> quenched the fluorescence of α-glucosidase in a static manner. 3D fluorescence spectra results indicated that <strong>WXC-25</strong> treatment could cause the conformation changes of α-glucosidase. Moreover, molecular docking simulated the detailed interaction of <strong>WXC25</strong> with α-glucosidase.</p></div>","PeriodicalId":257,"journal":{"name":"Bioorganic Chemistry","volume":null,"pages":null},"PeriodicalIF":4.5000,"publicationDate":"2024-08-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"2β-Acetoxyferruginol derivatives as α-glucosidase inhibitors: Synthesis and biological evaluation\",\"authors\":\"\",\"doi\":\"10.1016/j.bioorg.2024.107770\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>To find potential α-glucosidase inhibitors, a series of 2β-acetoxyferuginol derivatives containing cinnamic acid (<strong>WXC-1 ∼ 25</strong>) were synthesized and investigated their biological activity. All derivatives (<strong>WXC-1 ∼ 25</strong>) displayed better inhibitory activity (IC<sub>50</sub> values: 7.56 ± 1.35 ∼ 25.63 ± 1.72 μM) compared to acarbose (IC<sub>50</sub> vaule: 564.28 ± 48.68 μM). In particularly, <strong>WXC-25</strong> with 4-hydroxycinnamic acid section showed the best inhibitory activity (IC<sub>50</sub> vaule: 2.02 ± 0.14 μM), ∼75-fold stronger than acarbose. Kinetics results suggested <strong>WXC-25</strong> being one reversible non-competition inhibitors. Fluorescence quenching results indicated that <strong>WXC-25</strong> quenched the fluorescence of α-glucosidase in a static manner. 3D fluorescence spectra results indicated that <strong>WXC-25</strong> treatment could cause the conformation changes of α-glucosidase. Moreover, molecular docking simulated the detailed interaction of <strong>WXC25</strong> with α-glucosidase.</p></div>\",\"PeriodicalId\":257,\"journal\":{\"name\":\"Bioorganic Chemistry\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":4.5000,\"publicationDate\":\"2024-08-29\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Bioorganic Chemistry\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S0045206824006758\",\"RegionNum\":2,\"RegionCategory\":\"医学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"BIOCHEMISTRY & MOLECULAR BIOLOGY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Bioorganic Chemistry","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0045206824006758","RegionNum":2,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"BIOCHEMISTRY & MOLECULAR BIOLOGY","Score":null,"Total":0}
2β-Acetoxyferruginol derivatives as α-glucosidase inhibitors: Synthesis and biological evaluation
To find potential α-glucosidase inhibitors, a series of 2β-acetoxyferuginol derivatives containing cinnamic acid (WXC-1 ∼ 25) were synthesized and investigated their biological activity. All derivatives (WXC-1 ∼ 25) displayed better inhibitory activity (IC50 values: 7.56 ± 1.35 ∼ 25.63 ± 1.72 μM) compared to acarbose (IC50 vaule: 564.28 ± 48.68 μM). In particularly, WXC-25 with 4-hydroxycinnamic acid section showed the best inhibitory activity (IC50 vaule: 2.02 ± 0.14 μM), ∼75-fold stronger than acarbose. Kinetics results suggested WXC-25 being one reversible non-competition inhibitors. Fluorescence quenching results indicated that WXC-25 quenched the fluorescence of α-glucosidase in a static manner. 3D fluorescence spectra results indicated that WXC-25 treatment could cause the conformation changes of α-glucosidase. Moreover, molecular docking simulated the detailed interaction of WXC25 with α-glucosidase.
期刊介绍：
Bioorganic Chemistry publishes research that addresses biological questions at the molecular level, using organic chemistry and principles of physical organic chemistry. The scope of the journal covers a range of topics at the organic chemistry-biology interface, including: enzyme catalysis, biotransformation and enzyme inhibition; nucleic acids chemistry; medicinal chemistry; natural product chemistry, natural product synthesis and natural product biosynthesis; antimicrobial agents; lipid and peptide chemistry; biophysical chemistry; biological probes; bio-orthogonal chemistry and biomimetic chemistry.
For manuscripts dealing with synthetic bioactive compounds, the Journal requires that the molecular target of the compounds described must be known, and must be demonstrated experimentally in the manuscript. For studies involving natural products, if the molecular target is unknown, some data beyond simple cell-based toxicity studies to provide insight into the mechanism of action is required. Studies supported by molecular docking are welcome, but must be supported by experimental data. The Journal does not consider manuscripts that are purely theoretical or computational in nature.
The Journal publishes regular articles, short communications and reviews. Reviews are normally invited by Editors or Editorial Board members. Authors of unsolicited reviews should first contact an Editor or Editorial Board member to determine whether the proposed article is within the scope of the Journal.
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