{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,18]],"date-time":"2026-08-18T04:58:35Z","timestamp":1787029115280,"version":"build-2736575974"},"reference-count":46,"publisher":"MDPI AG","issue":"4","license":[{"start":{"date-parts":[[2024,2,13]],"date-time":"2024-02-13T00:00:00Z","timestamp":1707782400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/100000002","name":"The National Institutes of Health","doi-asserted-by":"publisher","award":["R01AT008099"],"award-info":[{"award-number":["R01AT008099"]}],"id":[{"id":"10.13039\/100000002","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100000002","name":"The National Institutes of Health","doi-asserted-by":"publisher","award":["S10RR022589"],"award-info":[{"award-number":["S10RR022589"]}],"id":[{"id":"10.13039\/100000002","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100000002","name":"The National Institutes of Health","doi-asserted-by":"publisher","award":["S10RR027878"],"award-info":[{"award-number":["S10RR027878"]}],"id":[{"id":"10.13039\/100000002","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100000002","name":"The National Institutes of Health","doi-asserted-by":"publisher","award":["U19AT010829"],"award-info":[{"award-number":["U19AT010829"]}],"id":[{"id":"10.13039\/100000002","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Rapid screening of botanical extracts for the discovery of bioactive natural products was performed using a fractionation approach in conjunction with flow-injection high-resolution mass spectrometry for obtaining chemical fingerprints of each fraction, enabling the correlation of the relative abundance of molecular features (representing individual phytochemicals) with the read-outs of bioassays. We applied this strategy for discovering and identifying constituents of Centella asiatica (C. asiatica) that protect against A\u03b2 cytotoxicity in vitro. C. asiatica has been associated with improving mental health and cognitive function, with potential use in Alzheimer\u2019s disease. Human neuroblastoma MC65 cells were exposed to subfractions of an aqueous extract of C. asiatica to evaluate the protective benefit derived from these subfractions against amyloid \u03b2-cytotoxicity. The % viability score of the cells exposed to each subfraction was used in conjunction with the intensity of the molecular features in two computational models, namely Elastic Net and selectivity ratio, to determine the relationship of the peak intensity of molecular features with % viability. Finally, the correlation of mass spectral features with MC65 protection and their abundance in different sub-fractions were visualized using GNPS molecular networking. Both computational methods unequivocally identified dicaffeoylquinic acids as providing strong protection against A\u03b2-toxicity in MC65 cells, in agreement with the protective effects observed for these compounds in previous preclinical model studies.<\/jats:p>","DOI":"10.3390\/molecules29040838","type":"journal-article","created":{"date-parts":[[2024,2,14]],"date-time":"2024-02-14T06:59:26Z","timestamp":1707893966000},"page":"838","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":5,"title":["Integrating High-Resolution Mass Spectral Data, Bioassays and Computational Models to Annotate Bioactives in Botanical Extracts: Case Study Analysis of C. asiatica Extract Associates Dicaffeoylquinic Acids with Protection against Amyloid-\u03b2 Toxicity"],"prefix":"10.3390","volume":"29","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-4731-0247","authenticated-orcid":false,"given":"Armando","family":"Alc\u00e1zar Maga\u00f1a","sequence":"first","affiliation":[{"name":"Department of Chemistry, Oregon State University, Corvallis, OR 97331, USA"},{"name":"BENFRA Botanical Dietary Supplements Research Center, Oregon Health & Science University, Portland, OR 97239, USA"},{"name":"Life Sciences Institute, University of British Columbia, Vancouver, BC V6T 1Z4, Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ashish","family":"Vaswani","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Oregon State University, Corvallis, OR 97331, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2959-2401","authenticated-orcid":false,"given":"Kevin S.","family":"Brown","sequence":"additional","affiliation":[{"name":"Department of Pharmaceutical Sciences, Oregon State University, Corvallis, OR 97331, USA"},{"name":"School of Chemical, Biological, and Environmental Engineering, Oregon State University, 116 Johnson Hall, 105 SW 26th Street, Corvallis, OR 97331, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6409-9159","authenticated-orcid":false,"given":"Yuan","family":"Jiang","sequence":"additional","affiliation":[{"name":"Department of Statistics, Oregon State University, Corvallis, OR 97331, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Md Nure","family":"Alam","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Oregon State University, Corvallis, OR 97331, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Maya","family":"Caruso","sequence":"additional","affiliation":[{"name":"Department of Neurology, Oregon Health & Science University, Portland, OR 97239, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Parnian","family":"Lak","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Oregon State University, Corvallis, OR 97331, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Paul","family":"Cheong","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Oregon State University, Corvallis, OR 97331, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Nora E.","family":"Gray","sequence":"additional","affiliation":[{"name":"BENFRA Botanical Dietary Supplements Research Center, Oregon Health & Science University, Portland, OR 97239, USA"},{"name":"Department of Neurology, Oregon Health & Science University, Portland, OR 97239, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7305-2256","authenticated-orcid":false,"given":"Joseph F.","family":"Quinn","sequence":"additional","affiliation":[{"name":"Department of Neurology, Oregon Health & Science University, Portland, OR 97239, USA"},{"name":"Parkinson\u2019s Disease Research Education and Clinical Care Center, Veterans\u2019 Administration Portland Health Care System, Portland, OR 97239, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1569-6453","authenticated-orcid":false,"given":"Amala","family":"Soumyanath","sequence":"additional","affiliation":[{"name":"BENFRA Botanical Dietary Supplements Research Center, Oregon Health & Science University, Portland, OR 97239, USA"},{"name":"Department of Neurology, Oregon Health & Science University, Portland, OR 97239, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6348-9347","authenticated-orcid":false,"given":"Jan F.","family":"Stevens","sequence":"additional","affiliation":[{"name":"BENFRA Botanical Dietary Supplements Research Center, Oregon Health & Science University, Portland, OR 97239, USA"},{"name":"Department of Pharmaceutical Sciences, Oregon State University, Corvallis, OR 97331, USA"},{"name":"Linus Pauling Institute, Oregon State University, Corvallis, OR 97331, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Claudia S.","family":"Maier","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Oregon State University, Corvallis, OR 97331, USA"},{"name":"BENFRA Botanical Dietary Supplements Research Center, Oregon Health & Science University, Portland, OR 97239, USA"},{"name":"Linus Pauling Institute, Oregon State University, Corvallis, OR 97331, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2024,2,13]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"844","DOI":"10.1104\/pp.18.01291","article-title":"Engineering Plant Secondary Metabolism in Microbial Systems","volume":"179","author":"Pyne","year":"2019","journal-title":"Plant Physiol."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"1120s","DOI":"10.1093\/jn\/131.3.1120S","article-title":"Global harmonization of herbal health claims","volume":"131","author":"Mahady","year":"2001","journal-title":"J. Nutr."},{"key":"ref_3","doi-asserted-by":"crossref","unstructured":"Commisso, M., Strazzer, P., Toffali, K., Stocchero, M., and Guzzo, F. (2013). Untargeted metabolomics: An emerging approach to determine the composition of herbal products. Comput. Struct. Biotechnol. J., 4.","DOI":"10.5936\/csbj.201301007"},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"9181","DOI":"10.3390\/s120709181","article-title":"A Unifying Review of Bioassay-Guided Fractionation, Effect-Directed Analysis and Related Techniques","volume":"12","author":"Weller","year":"2012","journal-title":"Sensors"},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"758","DOI":"10.1021\/acs.jnatprod.7b00737","article-title":"Bioactivity-Based Molecular Networking for the Discovery of Drug Leads in Natural Product Bioassay-Guided Fractionation","volume":"81","author":"Nothias","year":"2018","journal-title":"J. Nat. Prod."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"3578","DOI":"10.1002\/rcm.4796","article-title":"Bioassay-directed fractionation for discovery of bioactive neutral lipids guided by relative mass defect filtering and multiplexed collision-induced dissociation","volume":"24","author":"Stagliano","year":"2010","journal-title":"Rapid Commun. Mass Spectrom."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"471","DOI":"10.1016\/j.jpba.2018.06.026","article-title":"Acetylcholinesterase-inhibitory activity of Iranian plants: Combined HPLC\/bioassay-guided fractionation, molecular networking and docking strategies for the dereplication of active compounds","volume":"158","author":"Farimani","year":"2018","journal-title":"J. Pharm. Biomed. Anal."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"281","DOI":"10.1016\/j.jaim.2018.05.009","article-title":"Bioassay guided fractionation of Cyclea peltata using in vitro RAW 264.7 cell culture, antioxidant assays and isolation of bioactive compound tetrandrine","volume":"11","author":"Shine","year":"2018","journal-title":"J. Ayurveda Integr. Med."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"1582","DOI":"10.1016\/j.biotechadv.2015.08.001","article-title":"Discovery and resupply of pharmacologically active plant-derived natural products: A review","volume":"33","author":"Atanasov","year":"2015","journal-title":"Biotechnol. Adv."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"2009","DOI":"10.1021\/cb4002798","article-title":"Integrated metabolomics approach facilitates discovery of an unpredicted natural product suite from Streptomyces coelicolor M145","volume":"8","author":"Sidebottom","year":"2013","journal-title":"ACS Chem. Biol."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"1686","DOI":"10.1021\/np400413s","article-title":"Molecular Networking as a Dereplication Strategy","volume":"76","author":"Yang","year":"2013","journal-title":"J. Nat. Prod."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"778","DOI":"10.1007\/s11306-013-0498-9","article-title":"Identification of bioactive metabolites against adenosine A1 receptor using NMR-based metabolomics","volume":"9","author":"Ali","year":"2013","journal-title":"Metabolomics"},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"35","DOI":"10.1016\/j.chemolab.2008.08.004","article-title":"Biomarker discovery in mass spectral profiles by means of selectivity ratio plot","volume":"95","author":"Rajalahti","year":"2009","journal-title":"Chemom. Intell. Lab. Syst."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"2581","DOI":"10.1021\/ac802514y","article-title":"Discriminating Variable Test and Selectivity Ratio Plot: Quantitative Tools for Interpretation and Variable (Biomarker) Selection in Complex Spectral or Chromatographic Profiles","volume":"81","author":"Rajalahti","year":"2009","journal-title":"Anal. Chem."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"376","DOI":"10.1021\/acs.jnatprod.5b01014","article-title":"Biochemometrics for Natural Products Research: Comparison of Data Analysis Approaches and Application to Identification of Bioactive Compounds","volume":"79","author":"Kellogg","year":"2016","journal-title":"J. Nat. Prod."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"768","DOI":"10.1111\/j.1467-9868.2005.00527.x","article-title":"Regularization and variable selection via the elastic net","volume":"67","author":"Zou","year":"2005","journal-title":"J. R. Stat. Soc. B"},{"key":"ref_17","doi-asserted-by":"crossref","unstructured":"Brown, K.S., Jamieson, P., Wu, W., Vaswani, A., Alcazar Magana, A., Choi, J., Mattio, L.M., Cheong, P.H., Nelson, D., and Reardon, P.N. (2022). Computation-Assisted Identification of Bioactive Compounds in Botanical Extracts: A Case Study of Anti-Inflammatory Natural Products from Hops. Antioxidants, 11.","DOI":"10.3390\/antiox11071400"},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"427","DOI":"10.1016\/S0944-7113(00)80065-3","article-title":"Chemical, pharmacological and clinical profile of the East Asian medical plant Centella asiatica","volume":"7","author":"Brinkhaus","year":"2000","journal-title":"Phytomedicine"},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"33","DOI":"10.2174\/187221411794351833","article-title":"Exploring the Role of \u201cBrahmi\u201d (Bacopa monnieri and Centella asiatica) in Brain Function and Therapy","volume":"5","author":"Shinomol","year":"2011","journal-title":"Recent Pat. Endocr. Metab. Immune Drug Discov."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"161","DOI":"10.1007\/s11101-017-9528-y","article-title":"Centella asiatica\u2014Phytochemistry and mechanisms of neuroprotection and cognitive enhancement","volume":"17","author":"Gray","year":"2018","journal-title":"Phytochem. Rev."},{"key":"ref_21","unstructured":"Kapoor, L.D. (1990). CRC Handbook of Ayurvedic Medicinal Plants, CRC Press. [1st ed.]."},{"key":"ref_22","first-page":"972178","article-title":"Neuroprotective Effects of Centella asiatica against Intracerebroventricular Colchicine-Induced Cognitive Impairment and Oxidative Stress","volume":"2009","author":"Kumar","year":"2009","journal-title":"Int. J. Alzheimers Dis."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"88","DOI":"10.1016\/j.tifs.2018.07.024","article-title":"Centella asiatica (Gotu kola) as a neuroprotectant and its potential role in healthy ageing","volume":"79","author":"Sabaragamuwa","year":"2018","journal-title":"Trends Food Sci. Technol."},{"key":"ref_24","first-page":"4","article-title":"Recent Updates in Neuroprotective and Neuroregenerative Potential of Centella asiatica","volume":"23","author":"Lokanathan","year":"2016","journal-title":"Malays. J. Med. Sci."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"1194","DOI":"10.1021\/acs.analchem.6b03625","article-title":"The \u201cPepSAVI-MS\u201d Pipeline for Natural Product Bioactive Peptide Discovery","volume":"89","author":"Kirkpatrick","year":"2017","journal-title":"Anal. Chem."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"824","DOI":"10.1021\/acs.jnatprod.0c01376","article-title":"Interlaboratory Comparison of Untargeted Mass Spectrometry Data Uncovers Underlying Causes for Variability","volume":"84","author":"Clark","year":"2021","journal-title":"J. Nat. Prod."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"359","DOI":"10.3233\/JAD-131913","article-title":"Caffeoylquinic acids in Centella asiatica protect against amyloid-\u03b2 toxicity","volume":"40","author":"Gray","year":"2014","journal-title":"J. Alzheimers Dis."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"1299","DOI":"10.1111\/tpj.15390","article-title":"Caffeoylquinic acids: Chemistry, biosynthesis, occurrence, analytical challenges, and bioactivity","volume":"107","author":"Kamimura","year":"2021","journal-title":"Plant J."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"722","DOI":"10.1002\/pca.2936","article-title":"Integration of mass spectral fingerprinting analysis with precursor ion (MS1) quantification for the characterisation of botanical extracts: Application to extracts of Centella asiatica (L.) Urban","volume":"31","author":"Magana","year":"2020","journal-title":"Phytochem. Anal."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"3479s","DOI":"10.1093\/jn\/134.12.3479S","article-title":"Potential synergy of phytochemicals in cancer prevention: Mechanism of action","volume":"134","author":"Liu","year":"2004","journal-title":"J. Nutr."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"869","DOI":"10.1039\/C9NP00011A","article-title":"Synergy and antagonism in natural product extracts: When 1 + 1 does not equal 2","volume":"36","author":"Caesar","year":"2019","journal-title":"Nat. Prod. Rep."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"105","DOI":"10.1007\/s11010-019-03516-9","article-title":"Chlorogenic acid isomers directly interact with Keap 1-Nrf2 signaling in Caco-2 cells","volume":"457","author":"Liang","year":"2019","journal-title":"Mol. Cell. Biochem."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"1039","DOI":"10.1016\/j.neuroscience.2010.05.049","article-title":"Neuroprotective effect of 3,5-di-O-caffeoylquinic acid on SH-SY5Y cells and senescence-accelerated-prone mice 8 through the up-regulation of phosphoglycerate kinase-1","volume":"169","author":"Han","year":"2010","journal-title":"Neuroscience"},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"112432","DOI":"10.1016\/j.phytochem.2020.112432","article-title":"Isolation, structure elucidation and neuroprotective effects of caffeoylquinic acid derivatives from the roots of Arctium lappa L","volume":"177","author":"Gao","year":"2020","journal-title":"Phytochemistry"},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"C250","DOI":"10.1111\/j.1750-3841.2010.02010.x","article-title":"Neuroprotective effect of caffeoylquinic acids from Artemisia princeps Pampanini against oxidative stress-induced toxicity in PC-12 cells","volume":"76","author":"Lee","year":"2011","journal-title":"J. Food Sci."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"183","DOI":"10.1055\/a-1903-2387","article-title":"Neuroprotective Properties of Chlorogenic Acid and 4,5-Caffeoylquinic Acid from Brazilian arnica (Lychnophora ericoides) after Acute Retinal Ischemia","volume":"89","author":"Liberato","year":"2023","journal-title":"Planta Med."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"10488","DOI":"10.1038\/s41598-021-89964-0","article-title":"Neuromodulation and neuroprotective effects of chlorogenic acids in excitatory synapses of mouse hippocampal slices","volume":"11","author":"Fernandes","year":"2021","journal-title":"Sci. Rep."},{"key":"ref_38","doi-asserted-by":"crossref","unstructured":"Matthews, D.G., Caruso, M., Alcazar Magana, A., Wright, K.M., Maier, C.S., Stevens, J.F., Gray, N.E., Quinn, J.F., and Soumyanath, A. (2020). Caffeoylquinic Acids in Centella asiatica Reverse Cognitive Deficits in Male 5XFAD Alzheimer\u2019s Disease Model Mice. Nutrients, 12.","DOI":"10.3390\/nu12113488"},{"key":"ref_39","doi-asserted-by":"crossref","unstructured":"Chiang, M.-C., Tsai, T.-Y., and Wang, C.-J. (2023). The Potential Benefits of Quercetin for Brain Health: A Review of Anti-Inflammatory and Neuroprotective Mechanisms. Int. J. Mol. Sci., 24.","DOI":"10.3390\/ijms24076328"},{"key":"ref_40","doi-asserted-by":"crossref","unstructured":"Khan, H., Ullah, H., Aschner, M., Cheang, W.S., and Akkol, E.K. (2019). Neuroprotective Effects of Quercetin in Alzheimer\u2019s Disease. Biomolecules, 10.","DOI":"10.3390\/biom10010059"},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"113245","DOI":"10.1016\/j.bbr.2021.113245","article-title":"Quercetin alleviates chronic unpredictable mild stress-induced depressive-like behaviors by promoting adult hippocampal neurogenesis via FoxG1\/CREB\/ BDNF signaling pathway","volume":"406","author":"Ma","year":"2021","journal-title":"Behav. Brain Res."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"828","DOI":"10.1038\/nbt.3597","article-title":"Sharing and community curation of mass spectrometry data with Global Natural Products Social Molecular Networking","volume":"34","author":"Wang","year":"2016","journal-title":"Nat. Biotechnol."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"153","DOI":"10.1007\/BF02814999","article-title":"Neurodegenerative mechanisms in Alzheimer disease\u2014A role for oxidative damage in amyloid beta protein precursor-mediated cell death","volume":"29","author":"Sopher","year":"1996","journal-title":"Mol. Chem. Neuropathol."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"427","DOI":"10.1016\/j.nbd.2006.10.003","article-title":"Effects of chemical chaperones on oxidative stress and detergent-insoluble species formation following conditional expression of amyloid precursor protein carboxy-terminal fragment","volume":"25","author":"Woltjer","year":"2007","journal-title":"Neurobiol. Dis."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"467","DOI":"10.3233\/JAD-2003-5607","article-title":"Advanced glycation endproduct precursor alters intracellular amyloid- beta\/A beta PP carboxy-terminal fragment aggregation and cytotoxicity","volume":"5","author":"Woltjer","year":"2003","journal-title":"J. Alzheimers Dis."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"103937","DOI":"10.1016\/j.chemolab.2020.103937","article-title":"mdatools\u2014R package for chemometrics","volume":"198","author":"Kucheryayskiy","year":"2020","journal-title":"Chemom. Intell. Lab. Syst."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/29\/4\/838\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T13:59:27Z","timestamp":1760104767000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/29\/4\/838"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2024,2,13]]},"references-count":46,"journal-issue":{"issue":"4","published-online":{"date-parts":[[2024,2]]}},"alternative-id":["molecules29040838"],"URL":"https:\/\/doi.org\/10.3390\/molecules29040838","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2024,2,13]]}}}