{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,6,2]],"date-time":"2026-06-02T10:35:58Z","timestamp":1780396558331,"version":"3.54.1"},"reference-count":58,"publisher":"MDPI AG","issue":"3","license":[{"start":{"date-parts":[[2025,2,5]],"date-time":"2025-02-05T00:00:00Z","timestamp":1738713600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100004901","name":"FAPEMIG","doi-asserted-by":"publisher","award":["APQ-01487-22"],"award-info":[{"award-number":["APQ-01487-22"]}],"id":[{"id":"10.13039\/501100004901","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100004901","name":"FAPEMIG","doi-asserted-by":"publisher","award":["APQ-04686-22"],"award-info":[{"award-number":["APQ-04686-22"]}],"id":[{"id":"10.13039\/501100004901","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100004901","name":"FAPEMIG","doi-asserted-by":"publisher","award":["88887.506792\/2020-00"],"award-info":[{"award-number":["88887.506792\/2020-00"]}],"id":[{"id":"10.13039\/501100004901","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100004901","name":"FAPEMIG","doi-asserted-by":"publisher","award":["001"],"award-info":[{"award-number":["001"]}],"id":[{"id":"10.13039\/501100004901","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100004901","name":"FAPEMIG","doi-asserted-by":"publisher","award":["409187\/2023-2"],"award-info":[{"award-number":["409187\/2023-2"]}],"id":[{"id":"10.13039\/501100004901","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100004901","name":"FAPEMIG","doi-asserted-by":"publisher","award":["421935\/2023-5"],"award-info":[{"award-number":["421935\/2023-5"]}],"id":[{"id":"10.13039\/501100004901","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100004901","name":"FAPEMIG","doi-asserted-by":"publisher","award":["010\/2021"],"award-info":[{"award-number":["010\/2021"]}],"id":[{"id":"10.13039\/501100004901","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100002322","name":"CAPES Prevention and Combat of Outbreaks, Endemics, Epidemics and Pandemics","doi-asserted-by":"publisher","award":["APQ-01487-22"],"award-info":[{"award-number":["APQ-01487-22"]}],"id":[{"id":"10.13039\/501100002322","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100002322","name":"CAPES Prevention and Combat of Outbreaks, Endemics, Epidemics and Pandemics","doi-asserted-by":"publisher","award":["APQ-04686-22"],"award-info":[{"award-number":["APQ-04686-22"]}],"id":[{"id":"10.13039\/501100002322","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100002322","name":"CAPES Prevention and Combat of Outbreaks, Endemics, Epidemics and Pandemics","doi-asserted-by":"publisher","award":["88887.506792\/2020-00"],"award-info":[{"award-number":["88887.506792\/2020-00"]}],"id":[{"id":"10.13039\/501100002322","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100002322","name":"CAPES Prevention and Combat of Outbreaks, Endemics, Epidemics and Pandemics","doi-asserted-by":"publisher","award":["001"],"award-info":[{"award-number":["001"]}],"id":[{"id":"10.13039\/501100002322","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100002322","name":"CAPES Prevention and Combat of Outbreaks, Endemics, Epidemics and Pandemics","doi-asserted-by":"publisher","award":["409187\/2023-2"],"award-info":[{"award-number":["409187\/2023-2"]}],"id":[{"id":"10.13039\/501100002322","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100002322","name":"CAPES Prevention and Combat of Outbreaks, Endemics, Epidemics and Pandemics","doi-asserted-by":"publisher","award":["421935\/2023-5"],"award-info":[{"award-number":["421935\/2023-5"]}],"id":[{"id":"10.13039\/501100002322","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100002322","name":"CAPES Prevention and Combat of Outbreaks, Endemics, Epidemics and Pandemics","doi-asserted-by":"publisher","award":["010\/2021"],"award-info":[{"award-number":["010\/2021"]}],"id":[{"id":"10.13039\/501100002322","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100003593","name":"Conselho Nacional de Ci\u00eancia e Tecnologia","doi-asserted-by":"publisher","award":["APQ-01487-22"],"award-info":[{"award-number":["APQ-01487-22"]}],"id":[{"id":"10.13039\/501100003593","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100003593","name":"Conselho Nacional de Ci\u00eancia e Tecnologia","doi-asserted-by":"publisher","award":["APQ-04686-22"],"award-info":[{"award-number":["APQ-04686-22"]}],"id":[{"id":"10.13039\/501100003593","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100003593","name":"Conselho Nacional de Ci\u00eancia e Tecnologia","doi-asserted-by":"publisher","award":["88887.506792\/2020-00"],"award-info":[{"award-number":["88887.506792\/2020-00"]}],"id":[{"id":"10.13039\/501100003593","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100003593","name":"Conselho Nacional de Ci\u00eancia e Tecnologia","doi-asserted-by":"publisher","award":["001"],"award-info":[{"award-number":["001"]}],"id":[{"id":"10.13039\/501100003593","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100003593","name":"Conselho Nacional de Ci\u00eancia e Tecnologia","doi-asserted-by":"publisher","award":["409187\/2023-2"],"award-info":[{"award-number":["409187\/2023-2"]}],"id":[{"id":"10.13039\/501100003593","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100003593","name":"Conselho Nacional de Ci\u00eancia e Tecnologia","doi-asserted-by":"publisher","award":["421935\/2023-5"],"award-info":[{"award-number":["421935\/2023-5"]}],"id":[{"id":"10.13039\/501100003593","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100003593","name":"Conselho Nacional de Ci\u00eancia e Tecnologia","doi-asserted-by":"publisher","award":["010\/2021"],"award-info":[{"award-number":["010\/2021"]}],"id":[{"id":"10.13039\/501100003593","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100004916","name":"Funda\u00e7\u00e3o de Amparo \u00e0 Pesquisa do Estado do Amazonas\u2014FAPEAM","doi-asserted-by":"publisher","award":["APQ-01487-22"],"award-info":[{"award-number":["APQ-01487-22"]}],"id":[{"id":"10.13039\/501100004916","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100004916","name":"Funda\u00e7\u00e3o de Amparo \u00e0 Pesquisa do Estado do Amazonas\u2014FAPEAM","doi-asserted-by":"publisher","award":["APQ-04686-22"],"award-info":[{"award-number":["APQ-04686-22"]}],"id":[{"id":"10.13039\/501100004916","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100004916","name":"Funda\u00e7\u00e3o de Amparo \u00e0 Pesquisa do Estado do Amazonas\u2014FAPEAM","doi-asserted-by":"publisher","award":["88887.506792\/2020-00"],"award-info":[{"award-number":["88887.506792\/2020-00"]}],"id":[{"id":"10.13039\/501100004916","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100004916","name":"Funda\u00e7\u00e3o de Amparo \u00e0 Pesquisa do Estado do Amazonas\u2014FAPEAM","doi-asserted-by":"publisher","award":["001"],"award-info":[{"award-number":["001"]}],"id":[{"id":"10.13039\/501100004916","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100004916","name":"Funda\u00e7\u00e3o de Amparo \u00e0 Pesquisa do Estado do Amazonas\u2014FAPEAM","doi-asserted-by":"publisher","award":["409187\/2023-2"],"award-info":[{"award-number":["409187\/2023-2"]}],"id":[{"id":"10.13039\/501100004916","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100004916","name":"Funda\u00e7\u00e3o de Amparo \u00e0 Pesquisa do Estado do Amazonas\u2014FAPEAM","doi-asserted-by":"publisher","award":["421935\/2023-5"],"award-info":[{"award-number":["421935\/2023-5"]}],"id":[{"id":"10.13039\/501100004916","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100004916","name":"Funda\u00e7\u00e3o de Amparo \u00e0 Pesquisa do Estado do Amazonas\u2014FAPEAM","doi-asserted-by":"publisher","award":["010\/2021"],"award-info":[{"award-number":["010\/2021"]}],"id":[{"id":"10.13039\/501100004916","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>The chemical complexity of natural products, such as Eugenia punicifolia (Kunth) DC. plant, presents a challenge when extracting and identifying bioactive compounds. This study investigates the impact of different extraction systems and seasonal variations on the chemical profile and pharmacological potential of E. punicifolia leaves using NMR spectroscopy for chemical analysis and canonical correlation analysis (CCA) for bioactivity correlation. Extracts obtained with methanol (M), ethanol (E), methanol\/ethanol (1:1, ME), and methanol\/ethanol\/water (3:1:1, MEW) were analyzed for antioxidant, antiglycation, and antiviral activities. Quantitative \u00b9H NMR, combined with the PULCON method, was used to quantify phenolic compounds such as quercetin, myricetin, catechin, and gallic acid. The results showed that the MEW extract obtained in the rainy season exhibited the highest antioxidant and antiglycation activities, with a greater than 93% of advanced-glycation end-products (AGEs) inhibition capacity. Furthermore, our results showed that all the extracts were able to inhibit over 94% of the Zika virus (ZIKV) infection in Vero E6 cells. The CCA established strong correlations between the phenolic compounds and bioactivities, identifying gallic acid, catechin, quercetin, and myricetin as key chemical markers. This study demonstrates the importance of selecting appropriate extraction systems and considering seasonality to optimize the pharmacological potential of E. punicifolia leaves and highlights the efficacy of NMR in linking chemical composition with bioactivities.<\/jats:p>","DOI":"10.3390\/molecules30030713","type":"journal-article","created":{"date-parts":[[2025,2,5]],"date-time":"2025-02-05T07:44:59Z","timestamp":1738741499000},"page":"713","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":3,"title":["Investigation of the Influence of the Extraction System and Seasonality on the Pharmacological Potential of Eugenia punicifolia Leaves"],"prefix":"10.3390","volume":"30","author":[{"ORCID":"https:\/\/orcid.org\/0009-0004-8149-5400","authenticated-orcid":false,"given":"Kidney O. G.","family":"Neves","sequence":"first","affiliation":[{"name":"N\u00facleo de Estudos Qu\u00edmicos de Micromol\u00e9culas da Amaz\u00f4nia\u2014NEQUIMA, Universidade Federal do Amazonas, Manaus 69067-005, AM, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0005-7784-7810","authenticated-orcid":false,"given":"Samuel O.","family":"Silva","sequence":"additional","affiliation":[{"name":"N\u00facleo de Estudos Qu\u00edmicos de Micromol\u00e9culas da Amaz\u00f4nia\u2014NEQUIMA, Universidade Federal do Amazonas, Manaus 69067-005, AM, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0003-8511-8648","authenticated-orcid":false,"given":"Marinildo S.","family":"Cruz","sequence":"additional","affiliation":[{"name":"N\u00facleo de Estudos Qu\u00edmicos de Micromol\u00e9culas da Amaz\u00f4nia\u2014NEQUIMA, Universidade Federal do Amazonas, Manaus 69067-005, AM, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Josiana Moreira","family":"Mar","sequence":"additional","affiliation":[{"name":"Laborat\u00f3rio de Pol\u00edmeros Nanoestruturados (NANOPOL), Departamento de F\u00edsica de Materiais, Universidade Federal do Amazonas, Manaus 69067-005, AM, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9168-9864","authenticated-orcid":false,"given":"Jaqueline A.","family":"Bezerra","sequence":"additional","affiliation":[{"name":"Laborat\u00f3rio de Pol\u00edmeros Nanoestruturados (NANOPOL), Departamento de F\u00edsica de Materiais, Universidade Federal do Amazonas, Manaus 69067-005, AM, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1446-723X","authenticated-orcid":false,"given":"Edgar A.","family":"Sanches","sequence":"additional","affiliation":[{"name":"Laborat\u00f3rio de Pol\u00edmeros Nanoestruturados (NANOPOL), Departamento de F\u00edsica de Materiais, Universidade Federal do Amazonas, Manaus 69067-005, AM, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9654-0957","authenticated-orcid":false,"given":"Natasha Marques","family":"Cassani","sequence":"additional","affiliation":[{"name":"Laboratory of Antiviral Research, Federal University of Uberl\u00e2ndia, Uberl\u00e2ndia 38405-302, MG, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Giovanna A.","family":"Antoniucci","sequence":"additional","affiliation":[{"name":"Laboratory of Antiviral Research, Federal University of Uberl\u00e2ndia, Uberl\u00e2ndia 38405-302, MG, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6348-7923","authenticated-orcid":false,"given":"Ana Carolina Gomes","family":"Jardim","sequence":"additional","affiliation":[{"name":"Laboratory of Antiviral Research, Federal University of Uberl\u00e2ndia, Uberl\u00e2ndia 38405-302, MG, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4164-8511","authenticated-orcid":false,"given":"Francisco C. M.","family":"Chaves","sequence":"additional","affiliation":[{"name":"Empresa Brasileira de Pesquisa Agropecu\u00e1ria\u2014Embrapa Amaz\u00f4nia Ocidental, Manaus 69010-970, AM, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1241-6578","authenticated-orcid":false,"given":"Leonard D. R.","family":"Acho","sequence":"additional","affiliation":[{"name":"Laborat\u00f3rio de Atividade Biol\u00f3gica, Faculdade de Ci\u00eancias Farmac\u00eauticas, Universidade Federal do Amazonas, Manaus 69067-005, AM, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9367-2812","authenticated-orcid":false,"given":"Emersom S.","family":"Lima","sequence":"additional","affiliation":[{"name":"Laborat\u00f3rio de Atividade Biol\u00f3gica, Faculdade de Ci\u00eancias Farmac\u00eauticas, Universidade Federal do Amazonas, Manaus 69067-005, AM, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8791-4803","authenticated-orcid":false,"given":"Marcos B.","family":"Machado","sequence":"additional","affiliation":[{"name":"N\u00facleo de Estudos Qu\u00edmicos de Micromol\u00e9culas da Amaz\u00f4nia\u2014NEQUIMA, Universidade Federal do Amazonas, Manaus 69067-005, AM, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Alan D. C.","family":"Santos","sequence":"additional","affiliation":[{"name":"N\u00facleo de Estudos Qu\u00edmicos de Micromol\u00e9culas da Amaz\u00f4nia\u2014NEQUIMA, Universidade Federal do Amazonas, Manaus 69067-005, AM, Brazil"},{"name":"N\u00facleo de Pesquisa de Produtos Naturais, Universidade Federal de Santa Maria, Santa Maria 97105-900, RS, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2025,2,5]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"49","DOI":"10.1590\/1809-43922000301057","article-title":"Anatomia foliar de pedra-hume-ca\u00e1 (Myrcia sphaerocarpa, Myrcia guianensis, Eugenia punicifolia\u2014Myrtaceae)","volume":"30","author":"Jorge","year":"2000","journal-title":"Acta Amaz."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"552","DOI":"10.1002\/pca.3312","article-title":"NMR and multivariate methods: Identification of chemical markers in extracts of pedra-ume-ca\u00e1 and their antiglycation, antioxidant, and enzymatic inhibition activities","volume":"35","author":"Oliveira","year":"2024","journal-title":"Phytochem. Anal."},{"key":"ref_3","unstructured":"Amorim, M., Verdan, M., Oliveira, C., and Santos, A.D.C. (2024). Essential Oils of Neotropical Myrtaceae Species from 2011 until 2023: An Update. Chem. Biodivers."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"4870","DOI":"10.1080\/14786419.2020.1739675","article-title":"In vitro and in silico studies for barbinervic acid, a triterpene isolated from Eugenia punicifolia that inhibits vasopressor tone","volume":"35","author":"Teixeira","year":"2021","journal-title":"Nat. Prod. Res."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"257","DOI":"10.1016\/j.jep.2014.09.041","article-title":"Antinociceptive, anti-inflammatory and gastroprotective effects of a hydroalcoholic extract from the leaves of Eugenia punicifolia (Kunth) DC. in rodents","volume":"157","author":"Basting","year":"2014","journal-title":"J. Ethnopharmacol."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"1816","DOI":"10.1002\/ptr.5206","article-title":"Eugenia punicifolia (Kunth) DC. as an Adjuvant Treatment for Type-2 Diabetes Mellitus: A non-Controlled, Pilot Study","volume":"28","author":"Sales","year":"2014","journal-title":"Phytother. Res."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"674","DOI":"10.1016\/j.foodres.2019.05.042","article-title":"Pedra-ume ca\u00e1 fruit: An Amazon cherry rich in phenolic compounds with antiglycant and antioxidant properties","volume":"123","author":"Ramos","year":"2019","journal-title":"Food Res. Int."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"1232","DOI":"10.1055\/a-0656-7262","article-title":"Traditional Uses, Phytochemistry, and Antimicrobial Activities of Eugenia Species\u2014A Review","volume":"84","author":"Souza","year":"2018","journal-title":"Planta Med."},{"key":"ref_9","doi-asserted-by":"crossref","unstructured":"Santos, C., Mizobucchi, A.L., Escaramboni, B., Lopes, B.P., Angolini, C.F.F., Eberlin, M.N., de Toledo, K.A., and N\u00fa\u00f1ez, E.G.F. (2020). Optimization of Eugenia punicifolia (Kunth) DC. leaf extraction using a simplex centroid design focused on extracting phenolics with antioxidant and antiproliferative activities. BMC Chem., 14.","DOI":"10.1186\/s13065-020-00686-2"},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"20","DOI":"10.1186\/s13020-018-0177-x","article-title":"Techniques for extraction and isolation of natural products: A comprehensive review","volume":"13","author":"Zhang","year":"2018","journal-title":"Chin. Med."},{"key":"ref_11","first-page":"e20240010","article-title":"1H NMR Chemical Profile and Antioxidant Activity of Eugenia punicifolia Extracts Over Seasons: A Metabolomic Pilot Study","volume":"35","author":"Neves","year":"2024","journal-title":"J. Braz. Chem. Soc."},{"key":"ref_12","doi-asserted-by":"crossref","unstructured":"Brunetti, I.L., Vendramini, R.C., Janu\u00e1rio, A.H., Fran\u00e7a, S.C., and Pepato, M.T. (2006). Effects and Toxicity of Eugenia punicifolia. Extracts in Streptozotocin-Diabetic Rats. Pharm. Biol., 44.","DOI":"10.1080\/13880200500530575"},{"key":"ref_13","doi-asserted-by":"crossref","unstructured":"Dogara, A.M., Ibrahim, M.T., Mahmud, A.A., Danladi, M.D., Lema, A.A., Usman, M., Tahir, A.S., and Tabti, K. (2024). Biological activity, chemical composition, and molecular docking of Eugenia punicifolia (Kunth) DC. J. Umm Al-Qura Univ. Appll. Sci.","DOI":"10.1007\/s43994-024-00160-y"},{"key":"ref_14","doi-asserted-by":"crossref","unstructured":"Sehlakgwe, P.F., Lall, N., and Prinsloo, G. (2020). 1H-NMR Metabolomics and LC-MS Analysis to Determine Seasonal Variation in a Cosmeceutical Plant Leucosidea sericea. Front. Pharmacol., 11.","DOI":"10.3389\/fphar.2020.00219"},{"key":"ref_15","doi-asserted-by":"crossref","unstructured":"Ravaglia, L.M., Oliveira, P.D., Holzgrabe, U., and Alcantara, G.B. (2024). qNMR in natural products: Practical approaches. What nobody tells you before starting your qNMR study!. Front. Nat. Prod., 3.","DOI":"10.3389\/fntpr.2024.1416195"},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"135016","DOI":"10.1016\/j.foodchem.2022.135016","article-title":"1H HR-MAS NMR chemical profile and chemometric analysis as a tool for quality control of different cultivars of green tea (Camellia sinensis)","volume":"408","author":"Rech","year":"2023","journal-title":"Food Chem."},{"key":"ref_17","doi-asserted-by":"crossref","unstructured":"Delgado-Altamirano, R., Garc\u00eda-Aguilera, M.E., Delgado-Dom\u00ednguez, J., Becker, I., Rodr\u00edguez de San Miguel, E., Rojas-Molina, A., and Esturau-Escofet, N. (2021). 1H NMR profiling and chemometric analysis as an approach to predict the leishmanicidal activity of dichloromethane extracts from Lantana camara (L.). J. Pharm. Biomed. Anal., 199.","DOI":"10.1016\/j.jpba.2021.114060"},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"117","DOI":"10.1016\/j.jpba.2003.12.024","article-title":"Prediction of anti-plasmodial activity of Artemisia annua extracts: Application of 1H NMR spectroscopy and chemometrics","volume":"35","author":"Bailey","year":"2004","journal-title":"J. Pharm. Biomed. Anal."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"83","DOI":"10.1002\/pca.2792","article-title":"Total content of kaurene diterpenes in Annona vepretorum stems via 1H qNMR: A method for speeding the identification of bioactive extracts","volume":"30","author":"Souza","year":"2019","journal-title":"Phytochem. Anal."},{"key":"ref_20","doi-asserted-by":"crossref","unstructured":"Khalef, L., Lydia, R., Filicia, K., and Moussa, B. (2024). Cell viability and cytotoxicity assays: Biochemical elements and cellular compartments. Cell Biochem. Funct., 42.","DOI":"10.1002\/cbf.4007"},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"1841","DOI":"10.1021\/jf030723c","article-title":"The chemistry behind antioxidant capacity assays","volume":"53","author":"Huang","year":"2005","journal-title":"J. Agric. Food Chem."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"1768","DOI":"10.1021\/jf803011r","article-title":"Comparative Study of Antioxidant Properties and Total Phenolic Content of 30 Plant Extracts of Industrial Interest Using DPPH, ABTS, FRAP, SOD, and ORAC Assays","volume":"57","author":"Dudonne","year":"2009","journal-title":"J. Agric. Food Chem."},{"key":"ref_23","doi-asserted-by":"crossref","unstructured":"Zargoosh, Z., Ghavam, M., Bacchetta, G., and Tavili, A. (2019). Effects of ecological factors on the antioxidant potential and total phenol content of Scrophularia striata Boiss. Sci. Rep., 9.","DOI":"10.1038\/s41598-019-52605-8"},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"1101","DOI":"10.4141\/cjps2011-239","article-title":"Factors affecting the antioxidant potential and health benefits of plant foods","volume":"92","author":"Li","year":"2012","journal-title":"Can. J. Plant. Sci."},{"key":"ref_25","doi-asserted-by":"crossref","unstructured":"Khalid, M., Petroianu, G., and Adem, A. (2022). Advanced Glycation End Products and Diabetes Mellitus: Mechanisms and Perspectives. Biomolecules, 12.","DOI":"10.3390\/biom12040542"},{"key":"ref_26","doi-asserted-by":"crossref","unstructured":"L\u00f3pez-Mart\u00ednez, L.M., Santacruz-Ortega, H., Navarro, R.E., Sotelo-Mundo, R.R., and Gonz\u00e1lez-Aguilar, G.A. (2015). A 1H NMR Investigation of the Interaction between Phenolic Acids Found in Mango (Manguifera indica cv Ataulfo) and Papaya (Carica papaya cv Maradol) and 1,1-diphenyl-2-picrylhydrazyl (DPPH) Free Radicals. PLoS ONE, 10.","DOI":"10.1371\/journal.pone.0140242"},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"59","DOI":"10.1016\/j.jpba.2013.06.017","article-title":"Orthogonal analytical methods for botanical standardization: Determination of green tea catechins by qNMR and LC\u2013MS\/MS","volume":"93","author":"Napolitano","year":"2013","journal-title":"J. Pharm. Biomed. Anal."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"115276","DOI":"10.1016\/j.jep.2022.115276","article-title":"Hypoglycemic effect and toxicity of the dry extract of Eugenia biflora (L.) DC. leaves","volume":"293","author":"Oliveira","year":"2022","journal-title":"J. Ethnopharmacol."},{"key":"ref_29","doi-asserted-by":"crossref","unstructured":"Oliveira, E.S.C., Pontes, F.L.D., Acho, L.D.R., Ros\u00e1rio, A.S., Silva, B.J.P., Ara\u00fajo, B.J., Campos, F.R., Lima, E.S., and Machado, M.B. (2021). qNMR quantification of phenolic compounds in dry extract of Myrcia multiflora leaves and its antioxidant, anti-AGE, and enzymatic inhibition activities. J. Pharm. Biomed. Anal., 201.","DOI":"10.1016\/j.jpba.2021.114109"},{"key":"ref_30","doi-asserted-by":"crossref","unstructured":"Truzzi, E., Marchetti, L., Benvenuti, S., Righi, V., Rossi, M.C., Gallo, V., and Bertelli, D. (2021). A Novel qNMR Application for the Quantification of Vegetable Oils Used as Adulterants in Essential Oils. Molecules, 26.","DOI":"10.3390\/molecules26185439"},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"160","DOI":"10.1071\/CH21149","article-title":"Determination of Sample Concentrations by PULCON NMR Spectroscopy","volume":"75","author":"Mak","year":"2022","journal-title":"Aust. J. Chem."},{"key":"ref_32","doi-asserted-by":"crossref","unstructured":"Watanabe, R., Sugai, C., Yamazaki, T., Matsushima, R., Uchida, H., Matsumiya, M., Takatsu, A., and Suzuki, T. (2016). Quantitative Nuclear Magnetic Resonance Spectroscopy Based on PULCON Methodology: Application to Quantification of Invaluable Marine Toxin, Okadaic Acid. Toxins, 8.","DOI":"10.3390\/toxins8100294"},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"2349","DOI":"10.1109\/TKDE.2019.2958342","article-title":"A Survey on Canonical Correlation Analysis","volume":"33","author":"Yang","year":"2021","journal-title":"IEEE Trans. Knowl. Data Eng."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"339","DOI":"10.1002\/pca.2980","article-title":"Spectrum-effect relationship between UPLC fingerprints and anti-lung cancer effect of Panax ginseng","volume":"32","author":"Zhou","year":"2021","journal-title":"Phytochem. Anal."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"121970","DOI":"10.1016\/j.jchromb.2020.121970","article-title":"Spectrum-effect relationship study between HPLC fingerprints and antioxidant activity of Sabia parviflora","volume":"1140","author":"Chen","year":"2020","journal-title":"J. Chromatogr. B"},{"key":"ref_36","first-page":"1134","article-title":"Antioxidant Activity of Quercetin: A Mechanistic Review","volume":"4","author":"Ugur","year":"2016","journal-title":"Turk. J. Agric. For."},{"key":"ref_37","first-page":"354","article-title":"Review of the antioxidant potential of flavonoids as a subgroup of polyphenols and partial substitute for synthetic antioxidants","volume":"13","author":"Hassanpour","year":"2023","journal-title":"Avicenna J. Phytomed."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1155\/2013\/125027","article-title":"Evaluation of Antioxidant, Immunomodulatory, and Cytotoxic Action of Fractions from Eugenia uniflora L. and Eugenia malaccensis L.: Correlation with Polyphenol and Flavanoid Content","volume":"2013","author":"Figueiroa","year":"2013","journal-title":"Sci. World J."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"84","DOI":"10.1016\/j.jfda.2016.10.017","article-title":"Polyphenols with antiglycation activity and mechanisms of action: A review of recent findings","volume":"25","author":"Yeh","year":"2017","journal-title":"J. Food Drug Anal."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"139880","DOI":"10.1016\/j.foodchem.2024.139880","article-title":"Effects of myricetin and its derivatives on nonenzymatic glycation: A mechanism study based on proteomic modification and fluorescence spectroscopy analysis","volume":"455","author":"Wang","year":"2024","journal-title":"Food Chem."},{"key":"ref_41","doi-asserted-by":"crossref","unstructured":"Cataneo, A.H.D., \u00c1vila, E.P., Mendes, L.A.d.O., de Oliveira, V.G., Ferraz, C.R., Almeida, M.V., Frabasile, S., Santos, C.N.D., Verri, W.A., and Bordignon, J. (2021). Flavonoids as Molecules With Anti-Zika virus Activity. Front. Microbiol., 12.","DOI":"10.3389\/fmicb.2021.710359"},{"key":"ref_42","doi-asserted-by":"crossref","unstructured":"Pereira, R.S., Santos, F.C., Campana, P.R., Costa, V.V., de P\u00e1dua, R.M., Souza, D.G., Teixeira, M.M., and Braga, F.C. (2023). Natural Products and Derivatives as Potential Zika virus Inhibitors: A Comprehensive Review. Viruses, 15.","DOI":"10.3390\/v15051211"},{"key":"ref_43","doi-asserted-by":"crossref","unstructured":"Liga, S., Paul, C., and P\u00e9ter, F. (2023). Flavonoids: Overview of Biosynthesis, Biological Activity, and Current Extraction Techniques. Plants, 12.","DOI":"10.3390\/plants12142732"},{"key":"ref_44","doi-asserted-by":"crossref","unstructured":"Rahmani, A.H., Almatroudi, A., Allemailem, K.S., Alwanian, W.M., Alharbi, B.F., Alrumaihi, F., Khan, A.A., and Almatroodi, S.A. (2023). Myricetin: A Significant Emphasis on Its Anticancer Potential via the Modulation of Inflammation and Signal Transduction Pathways. Int. J. Mol. Sci., 24.","DOI":"10.3390\/ijms24119665"},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"532","DOI":"10.1016\/j.biotechadv.2015.12.014","article-title":"Quercetin and the mitochondria: A mechanistic view","volume":"34","author":"Oliveira","year":"2016","journal-title":"Biotechnol. Adv."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"415","DOI":"10.1007\/s10529-016-2261-6","article-title":"Inhibitory effect of flavonoids against NS2B-NS3 protease of ZIKA virus and their structure activity relationship","volume":"39","author":"Lim","year":"2017","journal-title":"Biotechnol. Lett."},{"key":"ref_47","doi-asserted-by":"crossref","unstructured":"Ramos, P.R., Mottin, M., Lima, C.S., Assis, L.R., de Oliveira, K.Z., Mesquita, N.C., Cassani, N.M., Santos, I.A., Borba, J.V., and Fiaia Costa, V.A. (2022). Natural Compounds as Non-Nucleoside Inhibitors of Zika Virus Polymerase through Integration of In Silico and In Vitro Approaches. Pharmaceuticals, 15.","DOI":"10.3390\/ph15121493"},{"key":"ref_48","doi-asserted-by":"crossref","unstructured":"Zou, M., Liu, H., Li, J., Yao, X., Chen, Y., Ke, C., and Liu, S. (2020). Structure-activity relationship of flavonoid bifunctional inhibitors against Zika virus infection. Biochem. Pharmacol., 177.","DOI":"10.1016\/j.bcp.2020.113962"},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"182","DOI":"10.1093\/infdis\/jix276","article-title":"A Sensitive Method for Detecting Zika Virus Antigen in Patients\u2019 Whole-Blood Specimens as an Alternative Diagnostic Approach","volume":"216","author":"Lum","year":"2017","journal-title":"J. Infect. Dis."},{"key":"ref_50","unstructured":"Minitab Inc. (2017). Minitab\u00ae 18.1, Minitab Inc."},{"key":"ref_51","unstructured":"Bruker BioSpin LGmbH & Co. KG (2021). TopSpin 3.6.3, Academia License."},{"key":"ref_52","first-page":"98","article-title":"Survey of ERETIC2 NMR for quantification","volume":"17","author":"Hong","year":"2013","journal-title":"J. Korean Soc. Magn. Reson. Med."},{"key":"ref_53","doi-asserted-by":"crossref","unstructured":"Donald, C.L., Brennan, B., Cumberworth, S.L., Rezelj, V.V., Clark, J.J., Cordeiro, M.T., Fran\u00e7a, R.F.O., Pena, L.J., Wilkie, G.S., and Silva, F.A. (2016). Full Genome Sequence and sfRNA Interferon Antagonist Activity of Zika Virus from Recife, Brazil. PLoS Negl. Trop. Dis., 10.","DOI":"10.1371\/journal.pntd.0005048"},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"630","DOI":"10.1016\/j.ijbiomac.2022.12.102","article-title":"Roles of Bothrops jararacussu toxins I and II: Antiviral findings against Zika virus","volume":"227","author":"Cassani","year":"2023","journal-title":"Int. J. Biol. Macromol."},{"key":"ref_55","unstructured":"GraphPad Software, LLC (2024). One-Way ANOVA Followed by Dunnett\u2019s Multiple Comparisons Test Was Performed Using GraphPad Prism Version 10.3.0 for Windows, GraphPad Software."},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"79","DOI":"10.1016\/j.jfca.2010.06.003","article-title":"The influence of domestic culinary processes on the Trolox Equivalent Antioxidant Capacity of green tea infusions","volume":"24","year":"2011","journal-title":"J. Food Compos. Anal."},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"129723","DOI":"10.1016\/j.foodchem.2021.129723","article-title":"Edible flowers from Theobroma speciosum: Aqueous extract rich in antioxidant compounds","volume":"356","author":"Mar","year":"2021","journal-title":"Food Chem."},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"200","DOI":"10.1271\/bbb.68.200","article-title":"Tomato paste fraction inhibiting the formation of advanced glycation end-products","volume":"68","author":"Kiho","year":"2004","journal-title":"Biosci. Biotechnol. Biochem."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/30\/3\/713\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,9]],"date-time":"2025-10-09T16:27:18Z","timestamp":1760027238000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/30\/3\/713"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2025,2,5]]},"references-count":58,"journal-issue":{"issue":"3","published-online":{"date-parts":[[2025,2]]}},"alternative-id":["molecules30030713"],"URL":"https:\/\/doi.org\/10.3390\/molecules30030713","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2025,2,5]]}}}