{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,2,19]],"date-time":"2026-02-19T09:59:49Z","timestamp":1771495189098,"version":"3.50.1"},"reference-count":38,"publisher":"Wiley","issue":"9","license":[{"start":{"date-parts":[[2024,8,7]],"date-time":"2024-08-07T00:00:00Z","timestamp":1722988800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chemistry &amp; Biodiversity"],"published-print":{"date-parts":[[2024,9]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Three naturally occurring prenylated pyranocoumarins, nordentatin (<jats:bold>1<\/jats:bold>), dentatin (<jats:bold>2<\/jats:bold>), and clausarin (<jats:bold>3<\/jats:bold>), isolated from the roots of <jats:italic>Clausena excavata<\/jats:italic> (Family Rutaceae), and <jats:italic>O<\/jats:italic>\u2010methylclausarin (<jats:bold>4<\/jats:bold>) which was obtained by methylation of <jats:bold>3<\/jats:bold>, were investigated for their \u03b1\u2010glucosidase inhibitory activity. The mechanism of action and the <jats:italic>in silico<\/jats:italic> prediction of their physicochemical and ADMET properties as well as the molecular docking were also studied. Compounds <jats:bold>1<\/jats:bold>\u2013<jats:bold>4<\/jats:bold> exhibited stronger \u03b1\u2010glucosidase inhibitory activity than the positive control, acarbose, through a non\u2010competitive mechanism. Among them, <jats:bold>3<\/jats:bold> exhibited the highest activity, with an IC<jats:sub>50<\/jats:sub> of 8.36\u2005\u03bcM, which is significantly stronger than that of acarbose (IC<jats:sub>50<\/jats:sub>=430.35\u2005\u03bcM). The prenyl group on C\u20103 and the hydroxyl group on C\u20105 in <jats:bold>3<\/jats:bold> may play important roles in enhancing the activity. Calculated physicochemical and ADMET parameters of <jats:bold>1<\/jats:bold>\u2013<jats:bold>4<\/jats:bold> satisfied the Lipinski's and Veber's rules. Molecular simulation analysis indicated they are promising drug candidates with no hepatotoxicity. Compound <jats:bold>3<\/jats:bold> exhibited potent activity in the experiment and demonstrated good drug properties based on the calculations. A molecular docking study revealed that <jats:bold>3<\/jats:bold> showed H\u2010bonding and \u03c0\u2010\u03c0 stacking interactions with selective Phe321, as well as interactions with thirteen other amino acid residues of the \u03b1\u2010glucosidase.<\/jats:p>","DOI":"10.1002\/cbdv.202401141","type":"journal-article","created":{"date-parts":[[2024,6,26]],"date-time":"2024-06-26T07:34:17Z","timestamp":1719387257000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":2,"title":["<i>\u03b1<\/i>\u2010Glucosidase Inhibitory Activity of Prenylated Pyranocoumarins from <i>Clausena excavata<\/i>: Mechanism of Action, ADMET and Molecular Docking"],"prefix":"10.1002","volume":"21","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-3846-8894","authenticated-orcid":false,"given":"Worrawat","family":"Promden","sequence":"first","affiliation":[{"name":"Division of General Science Faculty of Education Buriram Rajabhat University  Buriram 31000 Thailand"}]},{"given":"Aphiwat","family":"Lophaet","sequence":"additional","affiliation":[{"name":"Division of General Science Faculty of Education Buriram Rajabhat University  Buriram 31000 Thailand"}]},{"ORCID":"https:\/\/orcid.org\/0009-0001-4322-7710","authenticated-orcid":false,"given":"Ployvadee","family":"Sripadung","sequence":"additional","affiliation":[{"name":"Integrative Pharmaceuticals and Innovative of Pharmaceutical Technology Research Unit Faculty of Pharmacy Mahasarakham University  Khamriang, Kantarawichai Maha Sarakham 44150 Thailand"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8697-0718","authenticated-orcid":false,"given":"Bunleu","family":"Sungthong","sequence":"additional","affiliation":[{"name":"Integrative Pharmaceuticals and Innovative of Pharmaceutical Technology Research Unit Faculty of Pharmacy Mahasarakham University  Khamriang, Kantarawichai Maha Sarakham 44150 Thailand"}]},{"given":"Thanatcha","family":"Samsee","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Center of Excellence for Innovation in Chemistry (PERCH-CIC) Faculty of Science Mahasarakham University  Khamriang, Kantarawichai Maha Sarakham 44150 Thailand"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8158-0312","authenticated-orcid":false,"given":"Chanuttha","family":"Ploylearmsang","sequence":"additional","affiliation":[{"name":"Social Pharmacy Research Unit Faculty of Pharmacy Mahasarakham University  Khamriang, Kantarawichai Maha Sarakham 44150 Thailand"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3321-1061","authenticated-orcid":false,"given":"Anake","family":"Kijjoa","sequence":"additional","affiliation":[{"name":"Instituto de Ci\u00eancias Biom\u00e9dicas Abel Salazar and CIIMAR Universidade do Porto  Rua de Jorge Viterbo Ferreira, 228 4050-313 Porto Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2451-9029","authenticated-orcid":false,"given":"Prapairat","family":"Seephonkai","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Center of Excellence for Innovation in Chemistry (PERCH-CIC) Faculty of Science Mahasarakham University  Khamriang, Kantarawichai Maha Sarakham 44150 Thailand"}]}],"member":"311","published-online":{"date-parts":[[2024,8,7]]},"reference":[{"key":"e_1_2_10_1_1","doi-asserted-by":"publisher","DOI":"10.2337\/diacare.23.3.390"},{"key":"e_1_2_10_2_1","unstructured":"GBD 2019 Diseases and injuries collaborators. \u2032Global burden of 369 diseases and injuries in 204 countries and territories 1990\u20132019: a systematic analysis for the global burden of disease study 2019\u2032 Lancet2020 396: 1204\u201322."},{"key":"e_1_2_10_3_1","unstructured":"Ministry of Public Health Thailand \u201cType-2 diabetes in Thailand 2019\u201d can be found underhttp:\/\/www.thaincd.com(accessed 27 November 2023)."},{"key":"e_1_2_10_4_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41598-022-07977-9"},{"key":"e_1_2_10_5_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tem.2007.10.004"},{"key":"e_1_2_10_6_1","doi-asserted-by":"publisher","DOI":"10.1007\/s11892-016-0794-7"},{"key":"e_1_2_10_7_1","doi-asserted-by":"publisher","DOI":"10.7555\/JBR.31.20160164"},{"key":"e_1_2_10_8_1","unstructured":"Institute for Quality and Efficiency in Health Care \u201cType 2 diabetes: Learn More \u2013 What medications help in type 2 diabetes?\u201dcan be found under."},{"key":"e_1_2_10_9_1","unstructured":"https:\/\/www.ncbi.nlm.nih.gov\/books\/NBK279506\/ (accessed 5 May 2024)."},{"key":"e_1_2_10_10_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.foodchem.2022.133561"},{"key":"e_1_2_10_11_1","doi-asserted-by":"publisher","DOI":"10.2174\/18756417MTExfMTQ1z"},{"key":"e_1_2_10_12_1","unstructured":"L.\u2005M. 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