{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,18]],"date-time":"2026-08-18T04:30:16Z","timestamp":1787027416987,"version":"build-2736575974"},"reference-count":85,"publisher":"MDPI AG","issue":"16","license":[{"start":{"date-parts":[[2026,8,15]],"date-time":"2026-08-15T00:00:00Z","timestamp":1786752000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100007288","name":"Mahasarakham University","doi-asserted-by":"crossref","id":[{"id":"10.13039\/501100007288","id-type":"DOI","asserted-by":"crossref"}]},{"id":[{"id":"https:\/\/ror.org\/0453j3c58","id-type":"ROR","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Plants"],"abstract":"<jats:p>Gyrinops vidalii (Thymelaeaceae), a critically endangered agarwood-producing species native to Thailand and Laos and remains phytochemically unexplored. In this study, the chemical constituents and biological activities of the ethyl acetate (EtOAc) fraction of methanol extract of G. vidalii leaves were investigated. Phytochemical analysis led the isolation of mangiferin (1), iriflophenone 3-C-\u03b2-D-glucoside (2), aquilarinenside E (3), iriflophenone 2-O-\u03b1-L-rhamnoside (4), 5,7,4\u2032-trimethoxyflavone (5), blumenol A (6), loliolide (7), 4-hydroxybenzoic acid methyl ester (8), and 4-hydroxybenzoic acid (9). Compound 1 exhibited potent DPPH radical scavenging activity with an SC50 value of 19.35 \u03bcM), whereas iriflophenone (3a), obtained by acid hydrolysis of 3, and 5 showed promising \u03b1-glucosidase inhibitory activity with IC50 values 100.06 and 174.57 \u03bcM, respectively. Molecular docking demonstrated favorable binding of both compounds within the \u03b1-glucosidase active site through hydrogen bonding, aromatic, and hydrophobic interactions, with binding energies of \u22127.4 and \u22128.0 kcal\/mol, respectively. Predicted ADMET properties further supported the drug-like potential of both compounds, indicating favorable aqueous solubility, high intestinal absorption, and no predicted hepatotoxicity, while differences were observed in their predicted blood\u2013brain barrier permeability. This study represents the first phytochemical investigation of G. vidalii, provides scientific support for its traditional use, and expands the chemotaxonomic knowledge of the closely related genera Gyrinops and Aquilaria.<\/jats:p>","DOI":"10.3390\/plants15162474","type":"journal-article","created":{"date-parts":[[2026,8,17]],"date-time":"2026-08-17T08:05:41Z","timestamp":1786953941000},"page":"2474","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Phytochemical Investigation of Gyrinops vidalii Leaves and Evaluation of the \u03b1-Glucosidase Inhibitory Activity of the Isolated Metabolites and Molecular Docking of the Active Compounds"],"prefix":"10.3390","volume":"15","author":[{"given":"Siriwan","family":"Srisit","sequence":"first","affiliation":[{"name":"Department of Chemistry and Center of Excellence for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Mahasarakham University, Maha Sarakham 44150, Thailand"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Thittaya","family":"Ketnad","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Center of Excellence for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Mahasarakham University, Maha Sarakham 44150, Thailand"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Khemika","family":"Singmahan","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Center of Excellence for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Mahasarakham University, Maha Sarakham 44150, Thailand"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Pasakorn","family":"Bunchalee","sequence":"additional","affiliation":[{"name":"Department of Biology, Faculty of Science, Mahasarakham University, Maha Sarakham 14450, Thailand"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Worrawat","family":"Promden","sequence":"additional","affiliation":[{"name":"Division of General Science, Faculty of Education, Buriram Rajabhat University, Buriram 31000, Thailand"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3565-1597","authenticated-orcid":false,"given":"Panawan","family":"Moosophon","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Center of Excellence for Innovation in Chemistry, Khon Kaen University, Khon Kaen 40002, Thailand"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0000-6337-1018","authenticated-orcid":false,"given":"Vanida","family":"Choomuenwai","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Faculty of Science and Technology, Nakhon Ratchasima Rajabhat University, Nakhon Ratchasima 30000, Thailand"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8697-0718","authenticated-orcid":false,"given":"Bunleu","family":"Sungthong","sequence":"additional","affiliation":[{"name":"Faculty of Pharmacy, Mahasarakham University, Maha Sarakham 44150, Thailand"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Nadtanet","family":"Nanthaboot","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Center of Excellence for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Mahasarakham University, Maha Sarakham 44150, Thailand"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3321-1061","authenticated-orcid":false,"given":"Anake","family":"Kijjoa","sequence":"additional","affiliation":[{"name":"School of Medicine and Biomedical Sciences Abel Salazar (ICBAS) and CIIMAR, Universidade do Porto, 4050-313 Porto, Portugal"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"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, Maha Sarakham 44150, Thailand"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2026,8,15]]},"reference":[{"key":"ref_1","first-page":"373","article-title":"Thymelaeaceae","volume":"Volume 5","author":"Kubitzki","year":"2003","journal-title":"The Families and Genera of Vascular Plants, Flowering Plants\u2014Dicotyledons"},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"344","DOI":"10.1093\/botlinnean\/boac014","article-title":"Phylogenetic relationships of Aquilaria and Gyrinops (Thymelaeaceae) revisited: Evidence from complete plastid genomes","volume":"3","author":"Lee","year":"2022","journal-title":"Biol. J. Linn. Soc."},{"key":"ref_3","first-page":"61","article-title":"Gyrinops ledermannii (Thymelaeaceae), being an agarwood producing species prompts call for further examination of taxonomic implications in the generic delimitation between Aquilaria and Gyrinops","volume":"13","author":"Compton","year":"2002","journal-title":"Flora Malesiana Bull."},{"key":"ref_4","doi-asserted-by":"crossref","unstructured":"Persoon, G.A., and Van Beek, H.H. (2008). \u201cGrowing the wood of the gods\u201d: Agarwood production in Southeast Asia. Smallholder Tree Growing for Rural Development and Environmental Services, Springer.","DOI":"10.1007\/978-1-4020-8261-0_12"},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"387","DOI":"10.1007\/s11418-008-0262-z","article-title":"Studies on Perilla, agarwood, and cinnamon through a combination of fieldwork and laboratory work","volume":"62","author":"Ito","year":"2008","journal-title":"J. Nat. Med."},{"key":"ref_6","unstructured":"China Pharmacopoeia Editorial Board (2010). Pharmacopoeia of the People\u2019s Republic of China, China Medical Science and Technology Press."},{"key":"ref_7","unstructured":"POWO (2024, September 01). Plants of the World Online. Available online: http:\/\/www.plantsoftheworldonline.org\/."},{"key":"ref_8","doi-asserted-by":"crossref","unstructured":"Lee, S.Y., and Mohamed, R. (2016). The origin and domestication of Aquilaria, an important agarwood-producing genus. Agarwood, Tropical Forestry, Springer.","DOI":"10.1007\/978-981-10-0833-7"},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"13","DOI":"10.21315\/tlsr2018.29.2.2","article-title":"Phylogenetic relatedness of several agarwood-producing taxa (Thymelaeaceae) from Indonesia","volume":"29","author":"Lee","year":"2018","journal-title":"Trop. Life Sci. Res."},{"key":"ref_10","first-page":"225","article-title":"Three more new records for the Thai flora","volume":"48","author":"Maxwell","year":"2000","journal-title":"Nat. Hist. Bull. Siam Soc."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"104435","DOI":"10.1016\/j.arabjc.2022.104435","article-title":"Biodiversity and application prospects of fungal endophytes in the agarwood-producing genera, Aquilaria and Gyrinops (Thymelaeaceae)","volume":"16","author":"Li","year":"2023","journal-title":"Arab. J. Chem."},{"key":"ref_12","unstructured":"Pha Khao Lao (2026, June 21). Gyrinops vidalii P.H.H\u00f4. Available online: https:\/\/species.phakhaolao.la\/search\/specie_details\/3060."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"753","DOI":"10.1016\/0031-9422(86)88042-6","article-title":"Wallenone, a C32 triterpenoid from the leaves of Gyrinops walla","volume":"25","author":"Schun","year":"1986","journal-title":"Phytochemistry"},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"120147","DOI":"10.1016\/j.indcrop.2024.120147","article-title":"2-(2-Phenylethyl)chromone dimers as melanin production inhibitors from agarwood of Gyrinops walla Gaertn","volume":"222","author":"Chen","year":"2024","journal-title":"Ind. Crops Prod."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"76","DOI":"10.1016\/j.indcrop.2015.01.060","article-title":"Characterisation of agarwood type resin of Gyrinops walla Gaertn growing in selected populations in Sri Lanka","volume":"69","author":"Subasunghe","year":"2015","journal-title":"Ind. Crops Prod."},{"key":"ref_16","doi-asserted-by":"crossref","unstructured":"Shao, H., Mei, W.-L., Dong, W.-H., Gai, C.-J., Li, W., Zhu, G.-P., and Dai, H.-F. (2016). 2-(2-Phenylethyl)chromone derivatives of agarwood originating from Gyrinops salicifolia. Molecules, 21.","DOI":"10.3390\/molecules21101313"},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"182","DOI":"10.1016\/j.fitote.2016.07.015","article-title":"Sesquiterpenes of agarwood from Gyrinops salicifolia","volume":"113","author":"Shao","year":"2016","journal-title":"Fitoterapia"},{"key":"ref_18","doi-asserted-by":"crossref","unstructured":"Dong, W.-H., Wang, H., Guo, F.-J., Mei, W.-L., Chen, H.-Q., Kong, F.-D., Li, W., Zhou, K.-B., and Dai, H.-F. (2019). Three new 2-(2-phenylethyl)chromone derivatives of agarwood originated from Gyrinops salicifolia. Molecules, 24.","DOI":"10.3390\/molecules24030576"},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"1068","DOI":"10.1055\/s-2003-45161","article-title":"Isolation of mangiferin from Bombax malabaricum and structure revision of shamimin","volume":"69","author":"Shahat","year":"2003","journal-title":"Planta Med."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"229","DOI":"10.4103\/0974-8490.69110","article-title":"C-Glucoside xanthone from the stem bark extract of Bersama engleriana","volume":"2","author":"Djemgou","year":"2010","journal-title":"Pharmacogn. Res."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"1373","DOI":"10.1016\/j.foodchem.2012.01.114","article-title":"Isolation and structure elucidation of phenolic compounds from Cyclopia subternata Vogel (Honeybush) intact plant and in vitro culture","volume":"133","author":"Kokotkiewicz","year":"2012","journal-title":"Food Chem."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"1573","DOI":"10.1016\/j.cclet.2014.07.013","article-title":"Five new benzophenone glycosides from the leaves of Aquilaria sinensis (Lour.) Gilg","volume":"25","author":"Sun","year":"2014","journal-title":"Chin. Chem. Lett."},{"key":"ref_23","first-page":"3299","article-title":"Further chemical investigation of leaves of Aquilaria sinensis","volume":"38","author":"Xia","year":"2013","journal-title":"Chin. J. Chin. Mater. Med."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"2030","DOI":"10.1080\/14786419.2019.1573233","article-title":"Benzophenone glycosides from the pericarps of Aquilaria yunnanensis S. C. Huang","volume":"34","author":"Sun","year":"2020","journal-title":"Nat. Prod. Res."},{"key":"ref_25","first-page":"120","article-title":"Antioxidant activity of Piper caninum and cyclooxygenase-2 inhibition by methoxylated flavones","volume":"12","author":"Nadri","year":"2015","journal-title":"Afr. J. Tradit. Complement. Altern. Med."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"205","DOI":"10.15625\/0866-708X\/53\/2\/5065","article-title":"Antimicrobial compounds from Rhizophora stylosa","volume":"53","author":"Huong","year":"2015","journal-title":"Vietnam J. Sci. Technol."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"30","DOI":"10.31276\/VJSTE.62(2).30-33","article-title":"Chemical constituents from ethyl acetate extract of the leaves of Rourea harmandiana Pierre","volume":"62","author":"Dinh","year":"2020","journal-title":"Vietnam J. Sci. Technol. Eng."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"1250","DOI":"10.4014\/jmb.2304.04044","article-title":"Identification of loliolide with anti-aging properties from Scenedesmus deserticola JD052","volume":"33","author":"Cho","year":"2023","journal-title":"J. Microbiol. Biotechnol."},{"key":"ref_29","doi-asserted-by":"crossref","unstructured":"Morais, M.M.B.A., Kumla, D., Martins, F.R.V., Alves, A., Gales, L., Silva, M.S.A., Costa, M.P., Mistry, S., Kijjoa, A., and Marais, M.S.C.R. (2024). Monoterpene hydroxy lactones isolated from Thalassiosira sp. microalga and their antibacterial and antioxidant activities. Molecules, 29.","DOI":"10.3390\/molecules29215175"},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"115","DOI":"10.1016\/j.actatropica.2011.07.001","article-title":"Mosquito larvicidat activity of methyl-p-hydroxybenzoate isolated from the leaves of Vitex trifolia Linn","volume":"120","author":"Kannathasan","year":"2011","journal-title":"Acta Trop."},{"key":"ref_31","first-page":"29","article-title":"Online DPPH assay couple with LC-QTOF-MS for rapid identification of antioxidant constituents from Zelkova serrata","volume":"32","author":"Vu","year":"2026","journal-title":"Nat. Prod. Commun."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"1672","DOI":"10.1248\/bpb.28.1672","article-title":"Isolation of a human intestinal bacterium that transforms mangiferin to norathyriol and inducibility of the enzyme that cleaves a C-glucosyl bond","volume":"28","author":"Sanugul","year":"2005","journal-title":"Biol. Pharm. Bull."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"84","DOI":"10.1186\/s12944-017-0449-y","article-title":"Mangiferin: A natural miracle bioactive compound against lifestyle related disorders","volume":"16","author":"Imran","year":"2017","journal-title":"Lipids Health Dis."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"762","DOI":"10.1021\/jf011064b","article-title":"Isolation and quantitative analysis of phenolic antioxidants, free sugars, and polyols from mango (Mangifera indica L.) stem bark aqueous decoction used in Cuba as a nutritional supplement","volume":"50","author":"Naddeo","year":"2002","journal-title":"J. Agric. Food Chem."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"103188","DOI":"10.1016\/j.cis.2024.103188","article-title":"Mangiferin: A comprehensive review on its extraction, purification and uses in food systems","volume":"329","author":"Cabezas","year":"2024","journal-title":"Adv. Colloid Interface Sci."},{"key":"ref_36","first-page":"4775","article-title":"Mangiferin: An effective therapeutic agent against several disorders (Review)","volume":"18","author":"Du","year":"2018","journal-title":"Mol. Med. Rep."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"104336","DOI":"10.1016\/j.phrs.2019.104336","article-title":"Mangiferin: A multipotent natural product preventing neurodegeneration in Alzheimer\u2019s and Parkinson\u2019s disease models","volume":"146","author":"Feng","year":"2019","journal-title":"Pharmacol. Res."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"100445","DOI":"10.1016\/j.phyplu.2023.100445","article-title":"In-depth analysis of the chemical composition, pharmacological effects, pharmacokinetics, and patent history of mangiferin","volume":"3","author":"Kaurav","year":"2023","journal-title":"Phytomed. Plus"},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"134","DOI":"10.1248\/cpb.57.134","article-title":"Flavonoid and a rare benzophenone glycoside from the leaves of Aquilaria sinensis","volume":"57","author":"Qi","year":"2009","journal-title":"Chem. Pharm. Bull."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"242","DOI":"10.1016\/j.phytochem.2010.11.025","article-title":"Bio-assay guided isolation and identification of \u03b1-glucosidase inhibitors from the leaves of Aquilaria sinensis","volume":"72","author":"Feng","year":"2011","journal-title":"Phytochemistry"},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"349","DOI":"10.1002\/pca.2416","article-title":"Qualitative and quantitative analysis of phenolic compounds in the leaves of Aquilaria sinensis using liquid chromatography-mass spectrometry","volume":"24","author":"Yu","year":"2013","journal-title":"Phytochem. Anal."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"259","DOI":"10.3136\/fstr.18.259","article-title":"Identification of phenolic compounds in Aquilaria crassna leaves via liquid chromatography-electrospray ionization mass spectroscopy","volume":"18","author":"Ito","year":"2012","journal-title":"Food Sci. Technol. Res."},{"key":"ref_43","first-page":"54","article-title":"Antioxidative compounds from Aquilaria crassna leaf","volume":"41","author":"Ray","year":"2014","journal-title":"Pharm. Sci. Asia"},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"684","DOI":"10.1021\/np50040a043","article-title":"Studies in the Thymelaeaceae III. Constituents of Gyrinops walla","volume":"48","author":"Schun","year":"1985","journal-title":"J. Nat. Prod."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"136","DOI":"10.3177\/jnsv.58.136","article-title":"Quantification of polyphenols and pharmacological analysis of water and ethanol-based extracts of cultivated agarwood leaves","volume":"58","author":"Ito","year":"2012","journal-title":"J. Nutr. Sci. Vitaminol."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"170","DOI":"10.1016\/j.fitote.2017.07.013","article-title":"Benzophenone glycosides from the flower buds of Aquilaria sinensis","volume":"121","author":"Yuan","year":"2017","journal-title":"Fitoterapia"},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"335","DOI":"10.1271\/bbb.70361","article-title":"Laxative effect of agarwood leaves and its mechanism","volume":"72","author":"Hara","year":"2008","journal-title":"Biosci. Biotechnol. Biochem."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"834","DOI":"10.1007\/s10600-016-1790-5","article-title":"Iriflophenone glycosides from Aquilaria sinensis","volume":"52","author":"Wu","year":"2016","journal-title":"Chem. Nat. Compd."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"21511","DOI":"10.1038\/s41598-025-08606-x","article-title":"Phylogenetic analysis of the critically endangered Aquilaria khasiana (Thymelaeaceae) using barcode markers and chloroplast genome, with updated conservation status","volume":"15","author":"Sengupta","year":"2025","journal-title":"Sci. Rep."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"553","DOI":"10.1016\/S0031-9422(01)00120-0","article-title":"Natural and synthetic benzophenones: Interaction with the cytosolic binding domain of P-glycoprotein","volume":"57","author":"Rancon","year":"2001","journal-title":"Phytochemistry"},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"1367","DOI":"10.1248\/cpb.50.1367","article-title":"New isoflavones and flavanol from Iris potaninii","volume":"50","author":"Purev","year":"2002","journal-title":"Chem. Pharm. Bull."},{"key":"ref_52","first-page":"955","article-title":"Chemical constituents of the underground parts of Iris florentina and their cytotoxic activity","volume":"10","author":"Yokosuka","year":"2015","journal-title":"Nat. Prod. Commun."},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"1084","DOI":"10.1007\/s12272-013-0088-4","article-title":"Two new tirucallane triterpenoids from the leaves of Aquilaria sinensis","volume":"36","author":"Cheng","year":"2013","journal-title":"Arch. Pharm. Res."},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"116185","DOI":"10.1016\/j.indcrop.2022.116185","article-title":"The key odor-active components differed in cultured agarwood from two germplasms of Aquilaria sinensis trees","volume":"194","author":"Yan","year":"2023","journal-title":"Ind. Crops Prod."},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"3709","DOI":"10.1039\/D3CC06164G","article-title":"Uncovering the secrets of agarwood aroma according to regions and grades using a comprehensive analytical strategy","volume":"60","author":"Xie","year":"2024","journal-title":"Chem. Commun."},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"122628","DOI":"10.1016\/j.indcrop.2026.122628","article-title":"Sesquiterpenoids in agarwood: Composition, biosynthesis, and metabolic regulation","volume":"240","author":"Yang","year":"2026","journal-title":"Ind. Crops Prod."},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"4113","DOI":"10.1039\/C8RA09409H","article-title":"Overview of sesquiterpenes and chromones of agarwood originating from four main species of the genus Aquilaria","volume":"9","author":"Gao","year":"2019","journal-title":"RSC Adv."},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"951","DOI":"10.1080\/10286020.2011.598860","article-title":"A novel degraded sesquiterpene from the fresh stem of Aquilaria sinensis","volume":"13","author":"Peng","year":"2011","journal-title":"J. Asian Nat. Prod. Res."},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"012036","DOI":"10.1088\/1755-1315\/457\/1\/012036","article-title":"Identification of anticancer compounds in leaves extracts of agarwood (Aquilaria malaccensis (Lamk.))","volume":"457","author":"Millaty","year":"2020","journal-title":"IOP Conf. Ser. Earth Environ. Sci."},{"key":"ref_60","doi-asserted-by":"crossref","unstructured":"Gangadhar, K.N., Rodrigues, M.J., Pereira, H., Gaspar, H., Malcata, F.X., Barreira, L., and Varela, J. (2020). Anti-Hepatocellular carcinoma (HepG2) activities of monoterpene hydroxy lactones isolated from the marine microalga Tisochrysis lutea. Mar. Drugs, 18.","DOI":"10.3390\/md18110567"},{"key":"ref_61","doi-asserted-by":"crossref","first-page":"397","DOI":"10.1016\/j.bse.2011.05.015","article-title":"Secondary metabolites from the seaweed Gracilaria lemaneiformis and their allelopathic effects on Skeletonema costatum","volume":"39","author":"Lu","year":"2011","journal-title":"Biochem. Syst. Ecol."},{"key":"ref_62","doi-asserted-by":"crossref","first-page":"57","DOI":"10.1021\/np0103057","article-title":"New loliolide derivatives from the brown alga Undaria pinnatifida","volume":"65","author":"Kimura","year":"2002","journal-title":"J. Nat. Prod."},{"key":"ref_63","doi-asserted-by":"crossref","first-page":"201","DOI":"10.4490\/algae.2011.26.2.201","article-title":"Antioxidant activity and cell protective effect of loliolide isolated from Sargassum ringgoldianum subsp. coreanum","volume":"26","author":"Yang","year":"2011","journal-title":"Algae"},{"key":"ref_64","doi-asserted-by":"crossref","first-page":"593","DOI":"10.1016\/j.sajb.2010.02.091","article-title":"Serotonin transporter affinity of (\u2212)-loliolide, a monoterpene lactone from Mondia Whitei","volume":"76","author":"Neergaard","year":"2010","journal-title":"S. Afr. J. Bot."},{"key":"ref_65","doi-asserted-by":"crossref","first-page":"171","DOI":"10.1021\/np50043a031","article-title":"Loliolide from Salvia divinorum","volume":"49","year":"1986","journal-title":"J. Nat. Prod."},{"key":"ref_66","doi-asserted-by":"crossref","first-page":"281","DOI":"10.1016\/0031-9422(94)85042-9","article-title":"Immuno-suppressive activity of a monoterpene from Eucommia ulmoides","volume":"37","author":"Okada","year":"1994","journal-title":"Phytochemistry"},{"key":"ref_67","doi-asserted-by":"crossref","first-page":"164","DOI":"10.1016\/j.jchromb.2014.01.038","article-title":"Iriflophenone-3-C-glucoside from Cyclopia genistoides: Isolation and quantitative comparison of antioxidant capacity with mangiferin and isomangiferin using on-line HPLC antioxidant assays","volume":"951\u2013952","author":"Malherbe","year":"2014","journal-title":"J. Chromatogr. B Anal. Technol. Biomed. Life Sci."},{"key":"ref_68","doi-asserted-by":"crossref","first-page":"2694","DOI":"10.1021\/np5007247","article-title":"Benzophenone C- and O-glucosides from Cyclopia genistoides (Honeybush) inhibit mammalian \u03b1-glucosidase","volume":"77","author":"Beelders","year":"2014","journal-title":"J. Nat. Prod."},{"key":"ref_69","doi-asserted-by":"crossref","unstructured":"Marinov, T., Kokanova-Nedialkova, Z., and Nedialkov, P.T. (2023). Naturally occurring simple oxygenated benzophenones: Structural diversity, distribution, and biological properties. Diversity, 15.","DOI":"10.3390\/d15101030"},{"key":"ref_70","doi-asserted-by":"crossref","first-page":"15637","DOI":"10.1021\/acsomega.2c00439","article-title":"Phytochemical constituents of Aquilaria malaccensis leaf extract and their anti-inflammatory activity against LPS\/IFN-\u03b3-stimulated RAW 264.7 cell line","volume":"7","author":"Eissa","year":"2022","journal-title":"ACS Omega"},{"key":"ref_71","doi-asserted-by":"crossref","unstructured":"Ishaque, M., Bibi, Y., Ayoubi, S.A., Masood, S., Nisa, S., and Qayyum, A. (2021). Iriflophenone-3-C-\u03b2-d-glucopyranoside from Dryopteris ramosa (Hope) C.Chr. with promising future as natural antibiotic for gastrointestinal tract infections. Antibiotics, 10.","DOI":"10.3390\/antibiotics10091128"},{"key":"ref_72","doi-asserted-by":"crossref","first-page":"101335","DOI":"10.1016\/j.rineng.2023.101335","article-title":"An accurate and universal protein-small molecule batch docking solution using Autodock Vina","volume":"19","author":"Che","year":"2023","journal-title":"Results Eng."},{"key":"ref_73","doi-asserted-by":"crossref","first-page":"4205","DOI":"10.1111\/j.1742-4658.2010.07810.x","article-title":"Crystal structures of isomaltase from Saccharomyces cerevisiae and in complex with its competitive inhibitor maltose","volume":"277","author":"Yamamoto","year":"2010","journal-title":"FEBS J."},{"key":"ref_74","unstructured":"BIOVIA Dassault Syst\u00e8mes (BIOVIA Discovery Studio Visualizer, 2020). BIOVIA Discovery Studio Visualizer, version 211020298."},{"key":"ref_75","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1016\/S0169-409X(96)00423-1","article-title":"Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings","volume":"23","author":"Lipinski","year":"1997","journal-title":"Adv. Drug Deliv. Rev."},{"key":"ref_76","doi-asserted-by":"crossref","unstructured":"Han, Y., Zhang, J., Hu, C.Q., Zhang, X., Ma, B., and Zhang, P. (2019). In silico ADME and toxicity prediction of ceftazidime and its impurities. Front. Pharmacol., 10.","DOI":"10.3389\/fphar.2019.00434"},{"key":"ref_77","doi-asserted-by":"crossref","first-page":"e07463","DOI":"10.1016\/j.heliyon.2021.e07463","article-title":"QSAR, molecular docking and ADMET properties in silico studies of novel 4,5,6,7-tetrahydrobenzo[D]-thiazol-2-Yl derivatives derived from dimedone as potent anti-tumor agents through inhibition of C-Met receptor tyrosine kinase","volume":"7","author":"Daoui","year":"2021","journal-title":"Heliyon"},{"key":"ref_78","doi-asserted-by":"crossref","unstructured":"Promden, W., Chanvorachote, P., Viriyabancha, W., Sintupachee, S., and De-Eknamkul, W. (2024). Maclura cochinchinensis (Lour.) Corner heartwood extracts containing resveratrol and oxyresveratrol inhibit melanogenesis in B16F10 melanoma cells. Molecules, 29.","DOI":"10.3390\/molecules29112473"},{"key":"ref_79","doi-asserted-by":"crossref","first-page":"7793","DOI":"10.48048\/tis.2024.7793","article-title":"Anti-inflammatory and antioxidant properties of crude methanol extracts from the flowers and peels of Khlong Seng local durian (Durio zibethinus Murr.)","volume":"21","author":"Promden","year":"2024","journal-title":"Trends Sci."},{"key":"ref_80","doi-asserted-by":"crossref","first-page":"e202401141","DOI":"10.1002\/cbdv.202401141","article-title":"\u03b1-Glucosidase inhibitory activity of prenylated pyranocoumarins from Clausena excavata: Mechanism of action, ADMET and molecular docking","volume":"21","author":"Promden","year":"2024","journal-title":"Chem. Biodivers."},{"key":"ref_81","doi-asserted-by":"crossref","first-page":"1989","DOI":"10.1007\/s00044-025-03461-x","article-title":"Potent \u03b1-glucosidase inhibitory activity of inoscavin A from fruiting bodies of Fulvifomes fastuosus: Mechanism of action, molecular docking and ADMET","volume":"34","author":"Singmahan","year":"2025","journal-title":"Med. Chem. Res."},{"key":"ref_82","doi-asserted-by":"crossref","first-page":"W296","DOI":"10.1093\/nar\/gky427","article-title":"SWISS-MODEL: Homology modelling of protein structures and complexes","volume":"46","author":"Waterhouse","year":"2018","journal-title":"Nucleic Acids Res."},{"key":"ref_83","unstructured":"Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Scalmani, G., Barone, V., Mennucci, B., and Petersson, G.A. (GAUSSIAN 09, 2009). GAUSSIAN 09, Revision A.02."},{"key":"ref_84","doi-asserted-by":"crossref","first-page":"3891","DOI":"10.1021\/acs.jcim.1c00203","article-title":"AutoDock Vina 1.2.0: New Docking Methods, Expanded Force Field, and Python Bindings","volume":"61","author":"Eberhardt","year":"2021","journal-title":"J. Chem. Inf. Model."},{"key":"ref_85","doi-asserted-by":"crossref","unstructured":"Han, X., Wang, P., Zhang, J., Lv, Y., Zhao, Z., Zhang, F., Shang, M., Liu, G., Wang, X., and Cai, S. (2025). \u03b1-Glucosidase Inhibition Mechanism and Anti-Hyperglycemic Effects of Flavonoids from Astragali Radix and Their Mixture Effects. Pharmaceuticals, 18.","DOI":"10.3390\/ph18050744"}],"container-title":["Plants"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/2223-7747\/15\/16\/2474\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,8,18]],"date-time":"2026-08-18T04:12:03Z","timestamp":1787026323000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/2223-7747\/15\/16\/2474"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,8,15]]},"references-count":85,"journal-issue":{"issue":"16","published-online":{"date-parts":[[2026,8]]}},"alternative-id":["plants15162474"],"URL":"https:\/\/doi.org\/10.3390\/plants15162474","relation":{},"ISSN":["2223-7747"],"issn-type":[{"value":"2223-7747","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,8,15]]}}}