Yong Yang , Tingsi Guo , Feibing Huang , Hao Zheng , Wenchu Li , Hanwen Yuan , Qingling Xie , Nusrat Hussain , Wei Wang , Yuqing Jian
{"title":"α-Glucosidase inhibitory flavonol glycosides from Cyclocarya paliurus (Batalin) Iljinskaja and their kinetics characteristics","authors":"Yong Yang , Tingsi Guo , Feibing Huang , Hao Zheng , Wenchu Li , Hanwen Yuan , Qingling Xie , Nusrat Hussain , Wei Wang , Yuqing Jian","doi":"10.1016/j.phytochem.2024.114195","DOIUrl":null,"url":null,"abstract":"<div><p>Seven previously undescribed flavonol glycosides including four rare flavonol glycoside cyclodimers, dicyclopaliosides A-C (<strong>1</strong>-<strong>3</strong>) with truxinate type and dicyclopalioside D (<strong>4</strong>) with truxillate type, as well as three kaempferol glycoside derivatives cyclopaliosides A-C (<strong>5</strong>–<strong>7</strong>), were obtained from the leaves of <em>Cyclocarya paliurus</em>. Their structures were elucidated by extensive spectroscopic methods and chemical analyses. All compounds were evaluated for their inhibitory <em>α</em>-glucosidase activities. Among them, compounds <strong>1</strong>–<strong>4</strong> display strong inhibitory activities with IC<sub>50</sub> values of 82.76 ± 1.41, 62.70 ± 4.00, 443.35 ± 16.48, and 6.31 ± 0.88 nM, respectively, while compounds <strong>5</strong>–<strong>7</strong> showed moderate activities with IC<sub>50</sub> values of 4.91 ± 0.75, 3.64 ± 0.68, and 5.32 ± 0.53 μΜ, respectively. The structure-activity relationship analysis assumed that the cyclobutane cores likely contribute to the enhancement of <em>α</em>-glucosidase inhibitory activities of dimers. Also, the interaction mechanism between flavonol glycoside dimers and <em>α</em>-glucosidase were explored by the enzyme kinetic assay, indicating that compounds <strong>1</strong>–<strong>3</strong> exhibited mixed-type inhibition, while <strong>4</strong> showed uncompetitive inhibition. Additionally, the active compounds have also undergone molecular docking evaluation.</p></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":null,"pages":null},"PeriodicalIF":3.2000,"publicationDate":"2024-06-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Phytochemistry","FirstCategoryId":"99","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0031942224002322","RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"BIOCHEMISTRY & MOLECULAR BIOLOGY","Score":null,"Total":0}
引用次数: 0
Abstract
Seven previously undescribed flavonol glycosides including four rare flavonol glycoside cyclodimers, dicyclopaliosides A-C (1-3) with truxinate type and dicyclopalioside D (4) with truxillate type, as well as three kaempferol glycoside derivatives cyclopaliosides A-C (5–7), were obtained from the leaves of Cyclocarya paliurus. Their structures were elucidated by extensive spectroscopic methods and chemical analyses. All compounds were evaluated for their inhibitory α-glucosidase activities. Among them, compounds 1–4 display strong inhibitory activities with IC50 values of 82.76 ± 1.41, 62.70 ± 4.00, 443.35 ± 16.48, and 6.31 ± 0.88 nM, respectively, while compounds 5–7 showed moderate activities with IC50 values of 4.91 ± 0.75, 3.64 ± 0.68, and 5.32 ± 0.53 μΜ, respectively. The structure-activity relationship analysis assumed that the cyclobutane cores likely contribute to the enhancement of α-glucosidase inhibitory activities of dimers. Also, the interaction mechanism between flavonol glycoside dimers and α-glucosidase were explored by the enzyme kinetic assay, indicating that compounds 1–3 exhibited mixed-type inhibition, while 4 showed uncompetitive inhibition. Additionally, the active compounds have also undergone molecular docking evaluation.
期刊介绍:
Phytochemistry is a leading international journal publishing studies of plant chemistry, biochemistry, molecular biology and genetics, structure and bioactivities of phytochemicals, including ''-omics'' and bioinformatics/computational biology approaches. Phytochemistry is a primary source for papers dealing with phytochemicals, especially reports concerning their biosynthesis, regulation, and biological properties both in planta and as bioactive principles. Articles are published online as soon as possible as Articles-in-Press and in 12 volumes per year. Occasional topic-focussed special issues are published composed of papers from invited authors.