{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,6,25]],"date-time":"2026-06-25T06:27:44Z","timestamp":1782368864006,"version":"3.54.5"},"reference-count":55,"publisher":"MDPI AG","issue":"13","license":[{"start":{"date-parts":[[2022,6,28]],"date-time":"2022-06-28T00:00:00Z","timestamp":1656374400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"University of Bologna, Italy"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Amino acids are ubiquitous components of mammalian milk and greatly contribute to its nutritional value. The compositional analysis of free amino acids is poorly reported in the literature even though their determination in the biological fluids of livestock animals is necessary to establish possible nutritional interventions. In the present study, the free amino acid profiles in mature swine milk, colostrum and plasma were assessed using a targeted metabolomics approach. In particular, 20 amino acids were identified and quantified via two alternative and complementary reversed-phase HPLC methods, involving two stationary phases based on core-shell technology, i.e., Kinetex C18 and Kinetex F5, and two detection systems, i.e., a diode array detector (DAD) and a fluorescence detector (FLD). The sample preparation involved a de-proteinization step, followed by pre-chromatographic derivatization with 9-fluorenylmethylchloroformate (FMOC-Cl). The two optimized methods were validated for specificity, linearity, sensitivity, matrix effect, accuracy and precision and the analytical performances were compared. The analytical methods proved to be suitable for free amino acid profiling in different matrices with high sensitivity and specificity. The correlations among amino acid levels in different biological fluids can be useful for the evaluation of physio-pathological status and to monitor the effects of therapeutic or nutritional interventions in humans and animals.<\/jats:p>","DOI":"10.3390\/molecules27134153","type":"journal-article","created":{"date-parts":[[2022,6,29]],"date-time":"2022-06-29T01:48:38Z","timestamp":1656467318000},"page":"4153","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":8,"title":["Determination of Free Amino Acids in Milk, Colostrum and Plasma of Swine via Liquid Chromatography with Fluorescence and UV Detection"],"prefix":"10.3390","volume":"27","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-0622-2248","authenticated-orcid":false,"given":"Roberto","family":"Gotti","sequence":"first","affiliation":[{"name":"Department of Pharmacy and Biotechnology FaBit, Alma Mater Studiorum, University of Bologna, Via Belmeloro 6, 40126 Bologna, Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Erika","family":"Esposito","sequence":"additional","affiliation":[{"name":"Department of Chemistry \u201cG. Ciamician\u201d, Alma Mater Studiorum, University of Bologna, Via F. Selmi 2, 40126 Bologna, Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7864-7822","authenticated-orcid":false,"given":"Diana","family":"Luise","sequence":"additional","affiliation":[{"name":"Department of Agricultural and Food Sciences, Alma Mater Studiorum, University of Bologna, Viale G. Fanin, 40127 Bologna, Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Stefano","family":"Tullio","sequence":"additional","affiliation":[{"name":"Department of Chemistry \u201cG. Ciamician\u201d, Alma Mater Studiorum, University of Bologna, Via F. Selmi 2, 40126 Bologna, Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Nicol\u00f2","family":"Interino","sequence":"additional","affiliation":[{"name":"Department of Chemistry \u201cG. Ciamician\u201d, Alma Mater Studiorum, University of Bologna, Via F. Selmi 2, 40126 Bologna, Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7019-6828","authenticated-orcid":false,"given":"Paolo","family":"Trevisi","sequence":"additional","affiliation":[{"name":"Department of Agricultural and Food Sciences, Alma Mater Studiorum, University of Bologna, Viale G. Fanin, 40127 Bologna, Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jessica","family":"Fiori","sequence":"additional","affiliation":[{"name":"Department of Chemistry \u201cG. Ciamician\u201d, Alma Mater Studiorum, University of Bologna, Via F. Selmi 2, 40126 Bologna, Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2022,6,28]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"2814","DOI":"10.1007\/s12161-016-0463-0","article-title":"Sensitive Analysis of 33 Free Amino Acids in Serum, Milk, and Muscle by Ultra-High Performance Liquid Chromatography-Quadrupole-Orbitrap High Resolution Mass Spectrometry","volume":"9","author":"Yin","year":"2016","journal-title":"Food Anal. Methods"},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"407","DOI":"10.1007\/s00726-013-1500-6","article-title":"Functional Amino Acids in Nutrition and Health","volume":"45","author":"Wu","year":"2013","journal-title":"Amino Acids"},{"key":"ref_3","doi-asserted-by":"crossref","unstructured":"Hong, J., Fang, L.H., Jeong, J.H., and Kim, Y.Y. (2020). Effects of L-Arginine Supplementation during Late Gestation on Reproductive Performance, Piglet Uniformity, Blood Profiles, and Milk Composition in High Prolific Sows. Animals, 10.","DOI":"10.3390\/ani10081313"},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"211","DOI":"10.1016\/j.anireprosci.2018.08.013","article-title":"Maternal Dietary Supplementation of Arginine Increases the Ratio of Total Cloned Piglets Born to Total Transferred Cloned Embryos by Improving the Pregnancy Rate of Recipient Sows","volume":"196","author":"Li","year":"2018","journal-title":"Anim. Reprod. Sci."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"881","DOI":"10.1016\/0958-6946(95)00072-0","article-title":"Protein, Fats, Vitamin and Mineral Concentrations in Porcine Colostrum and Milk from Parturition to 60 Days","volume":"6","author":"Martin","year":"1996","journal-title":"Int. Dairy J."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"18496","DOI":"10.1038\/s41598-019-55006-z","article-title":"Dose-Response of Different Dietary Leucine Levels on Growth Performance and Amino Acid Metabolism in Piglets Differing for Aminoadipate-Semialdehyde Synthase Genotypes","volume":"9","author":"Bertocchi","year":"2019","journal-title":"Sci. Rep."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"425","DOI":"10.1017\/S0029665112000560","article-title":"Towards Amino Acid Recommendations for Specific Physiological and Patho-Physiological States in Pigs","volume":"71","author":"Gondret","year":"2012","journal-title":"Proc. Nutr. Soc."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"77","DOI":"10.1186\/s40104-018-0291-8","article-title":"Recent Progress of Porcine Milk Components and Mammary Gland Function","volume":"9","author":"Zhang","year":"2018","journal-title":"J. Anim. Sci. Biotechnol."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"20","DOI":"10.1186\/s40104-016-0078-8","article-title":"Amino Acids and Mammary Gland Development: Nutritional Implications for Milk Production and Neonatal Growth","volume":"7","author":"Rezaei","year":"2016","journal-title":"J. Anim. Sci. Biotechnol."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"1837","DOI":"10.1080\/1828051X.2021.1960210","article-title":"Productive Effects of a Colostrum-Oriented Amino Acid Dietary Supply for Sows in Transition from Gestation to Lactation","volume":"20","author":"Luise","year":"2021","journal-title":"Ital. J. Anim. Sci."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"1421","DOI":"10.1093\/clinchem\/43.8.1421","article-title":"Amino Acid Determination in Biological Fluids by Automated Ion-Exchange Chromatography: Performance of Hitachi L-8500A","volume":"43","author":"Charret","year":"1997","journal-title":"Clin. Chem."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"2456","DOI":"10.1021\/jf2052338","article-title":"Gas Chromatography\u2013Mass Spectrometry Method for the Determination of Free Amino Acids as Their Dimethyl- Tert -Butylsilyl (TBDMS) Derivatives in Animal Source Food","volume":"60","author":"Ruiz","year":"2012","journal-title":"J. Agric. Food Chem."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"222","DOI":"10.1016\/j.jchromb.2008.06.018","article-title":"Automated GC\u2013MS Analysis of Free Amino Acids in Biological Fluids","volume":"870","author":"Kaspar","year":"2008","journal-title":"J. Chromatogr. B"},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"96","DOI":"10.1016\/j.chroma.2012.04.029","article-title":"Simultaneous Extraction and Derivatization of Amino Acids and Free Fatty Acids in Meat Products","volume":"1241","author":"Leggio","year":"2012","journal-title":"J. Chromatogr. A"},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"480","DOI":"10.1016\/j.jpba.2015.01.015","article-title":"Optimization and Validation of a Chiral GC\u2013MS Method for the Determination of Free d-Amino Acids Ratio in Human Urine: Application to a Gestational Diabetes Mellitus Study","volume":"107","author":"Lorenzo","year":"2015","journal-title":"J. Pharm. Biomed. Anal."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"83","DOI":"10.1016\/j.cccn.2004.11.016","article-title":"Analysis of Plasma Amino Acids by HPLC with Photodiode Array and Fluorescence Detection","volume":"354","author":"Schwarz","year":"2005","journal-title":"Clin. Chim. Acta"},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"557","DOI":"10.1016\/S0021-9673(00)97000-6","article-title":"Appraisal of Four Pre-Column Derivatization Methods for the High-Performance Liquid Chromatographic Determination of Free Amino Acids in Biological Materials","volume":"499","author":"Pollack","year":"1990","journal-title":"J. Chromatogr."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"285","DOI":"10.1016\/0378-4347(91)80531-G","article-title":"Application of Amino Acid Analysis by High-Performance Liquid Chromatography with Phenyl Isothiocyanate Derivatization to the Rapid Determination of Free Amino Acids in Biological Samples","volume":"570","author":"Fierabracci","year":"1991","journal-title":"J. Chromatogr. B Biomed. Sci. Appl."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"116","DOI":"10.1016\/j.jchromb.2014.03.025","article-title":"Analysis of Amino Acid Composition in Proteins of Animal Tissues and Foods as Pre-Column o-Phthaldialdehyde Derivatives by HPLC with Fluorescence Detection","volume":"964","author":"Dai","year":"2014","journal-title":"J. Chromatogr. B"},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"769","DOI":"10.1038\/320769a0","article-title":"PITC Derivatives in Amino Acid Analysis","volume":"320","author":"Cohen","year":"1986","journal-title":"Nature"},{"key":"ref_21","first-page":"660","article-title":"Amino Acid Quantification in the Presence of Sugars Using HPLC and Pre-Column Derivatization with 3-MPA\/OPA and FMOC-Cl","volume":"55","author":"Kosmerl","year":"2008","journal-title":"Acta Chim. Slov."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"323","DOI":"10.1016\/0021-9673(94)80121-5","article-title":"Stability of O-Phthalaldehyde-Sulfite Derivatives of Amino Acids and Their Methyl Esters: Electrochemical and Chromatographic Properties","volume":"668","author":"Volicer","year":"1994","journal-title":"J. Chromatogr. A"},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"65","DOI":"10.1016\/0003-2697(84)90307-5","article-title":"Amino Acid Analysis by Reverse-Phase High-Performance Liquid Chromatography: Precolumn Derivatization with Phenylisothiocyanate","volume":"136","author":"Heinrikson","year":"1984","journal-title":"Anal. Biochem."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"609","DOI":"10.1016\/S0021-9673(00)91638-8","article-title":"Determination of Amino Acids with 9-Fluorenylmethyl Chloroformate and Reversed-Phase High-Performance Liquid Chromatography","volume":"282","author":"Einarsson","year":"1983","journal-title":"J. Chromatogr. A"},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"3064","DOI":"10.1016\/j.chroma.2009.01.068","article-title":"Amino Acid Analysis by High-Performance Liquid Chromatography after Derivatization with 9-Fluorenylmethyloxycarbonyl Chloride Literature Overview and Further Study","volume":"1216","year":"2009","journal-title":"J. Chromatogr. A"},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"107","DOI":"10.1046\/j.1439-0442.2000.00271.x","article-title":"Plasma Amino Acid Pattern during the First Month of Life in Calves Fed the First Colostrum at 0-2 h or at 24-25 h after Birth","volume":"47","author":"Zanker","year":"2000","journal-title":"J. Vet. Med. Ser. A"},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"127120","DOI":"10.1016\/j.foodchem.2020.127120","article-title":"Functional, Nutritional, Antioxidant, Sensory Properties and Comparative Peptidomic Profile of Faba Bean (Vicia faba, L.) Seed Protein Hydrolysates and Fortified Apple Juice","volume":"330","author":"Samaei","year":"2020","journal-title":"Food Chem."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"496","DOI":"10.1097\/01.MPG.0000150407.30058.47","article-title":"Free Amino Acids in Full-Term and Pre-Term Human Milk and Infant Formula","volume":"40","author":"Chuang","year":"2005","journal-title":"J. Pediatric Gastroenterol. Nutr."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"2216","DOI":"10.3945\/jn.116.238832","article-title":"Perinatal Dietary Choline Deficiency in Sows Influences Concentrations of Choline Metabolites, Fatty Acids, and Amino Acids in Milk throughout Lactation","volume":"146","author":"Mudd","year":"2016","journal-title":"J. Nutr."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"104064","DOI":"10.1016\/j.livsci.2020.104064","article-title":"Soybean Bioactive Peptides Supplementation during Late Gestation and Lactation Affect the Reproductive Performance, Free Amino Acid Composition in Plasma and Milk of Sows","volume":"237","author":"Zhuo","year":"2020","journal-title":"Livest. Sci."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"1007","DOI":"10.3389\/fimmu.2020.01007","article-title":"Free Amino Acids in Human Milk: A Potential Role for Glutamine and Glutamate in the Protection Against Neonatal Allergies and Infections","volume":"11","author":"Wiertsema","year":"2020","journal-title":"Front. Immunol."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"111","DOI":"10.1089\/bfm.2011.0155","article-title":"Concentration of Free Amino Acids in Human Milk of Women with Gestational Diabetes Mellitus and Healthy Women","volume":"8","author":"Klein","year":"2013","journal-title":"Breastfeed. Med."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"838","DOI":"10.1292\/jvms.19-0064","article-title":"Differences in Free Amino Acid Concentrations in Milk between Wistar and Wistar Kyoto Rats","volume":"81","author":"Hamada","year":"2019","journal-title":"J. Vet. Med. Sci."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"415","DOI":"10.1093\/jn\/124.3.415","article-title":"Free and Protein-Bound Amino Acids in Sow\u2019s Colostrum and Milk","volume":"124","author":"Wu","year":"1994","journal-title":"J. Nutr."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"135","DOI":"10.1016\/j.chroma.2014.10.040","article-title":"Analysis of Free Amino Acids in Natural Waters by Liquid Chromatography-Tandem Mass Spectrometry","volume":"1370","author":"How","year":"2014","journal-title":"J. Chromatogr. A"},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"166","DOI":"10.1016\/j.jchromb.2013.11.017","article-title":"A Rapid, Sensitive Method for Quantitative Analysis of Underivatized Amino Acids by Liquid Chromatography-Tandem Mass Spectrometry (LC-MS\/MS)","volume":"944","author":"Le","year":"2014","journal-title":"J. Chromatogr. B Anal. Technol. Biomed. Life Sci."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"2208","DOI":"10.1002\/jssc.201500162","article-title":"Free Amino Acids Analysis by Liquid Chromatography with Tandem Mass Spectrometry in Several Botanicals with Antioxidant Character","volume":"38","author":"Moldoveanu","year":"2015","journal-title":"J. Sep. Sci."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"213","DOI":"10.1007\/s00217-019-03385-y","article-title":"Metabolomics Methods to Analyze Full Spectrum of Amino Acids in Different Domains of Bovine Colostrum and Mature Milk","volume":"246","author":"Li","year":"2020","journal-title":"Eur. Food Res. Technol."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"993","DOI":"10.1007\/s00726-021-03002-x","article-title":"Determination of Amino Acids in Human Biological Fluids by High-Performance Liquid Chromatography: Critical Review","volume":"53","author":"Ratajczyk","year":"2021","journal-title":"Amino Acids"},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"133204","DOI":"10.1016\/j.foodchem.2022.133204","article-title":"Development, Validation, and Uncertainty Measurement of HPLC-DAD Method for Determination of Some Free Amino Acids in Infant Formula and Medical Food Products for Inborn Errors of Metabolism","volume":"390","author":"Vakili","year":"2022","journal-title":"Food Chem."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"2001253","DOI":"10.1155\/2022\/2001253","article-title":"Identification of Geographical Origin of Milk by Amino Acid Profile Coupled with Chemometric Analysis","volume":"2022","author":"Kang","year":"2022","journal-title":"J. Food Qual."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"696703","DOI":"10.3389\/fvets.2021.696703","article-title":"Effects of a High-Grain Diet With a Buffering Agent on Milk Protein Synthesis in Lactating Goats","volume":"8","author":"He","year":"2021","journal-title":"Front. Vet. Sci."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"3046","DOI":"10.1111\/1750-3841.15794","article-title":"Characterization and Biological Properties of Peptides Isolated from Dried Fermented Cow Milk Products by RP-HPLC: Amino Acid Composition, Antioxidant, Antihypertensive, and Antidiabetic Properties","volume":"86","author":"Alhamad","year":"2021","journal-title":"J. Food Sci."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"553674","DOI":"10.3389\/fnut.2020.553674","article-title":"Circulating Branched Chain Amino Acid Concentrations Are Higher in Dairy-Avoiding Females Following an Equal Volume of Sheep Milk Relative to Cow Milk: A Randomized Controlled Trial","volume":"7","author":"Milan","year":"2020","journal-title":"Front. Nutr."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"845","DOI":"10.1079\/BJN19940089","article-title":"Amino Acid Composition of the Milk of Some Mammalian Species Changes with Stage of Lactation","volume":"72","author":"Davis","year":"1994","journal-title":"Br. J. Nutr."},{"key":"ref_46","doi-asserted-by":"crossref","unstructured":"Hurley, W.L. (2014). 9. Composition of Sow Colostrum and Milk. The Gestating and Lactating Sow, Wageningen Academic Publishers.","DOI":"10.3920\/978-90-8686-803-2_9"},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"13","DOI":"10.1016\/j.anifeedsci.2019.04.015","article-title":"Effect of Optimizing Dietary Valine-to-Lysine Ratio in Late Gestation or Lactation on Biochemical Indices and Performance of Lactating Primiparous Sows","volume":"253","author":"Gao","year":"2019","journal-title":"Anim. Feed Sci. Technol."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"1853","DOI":"10.2527\/1997.7571853x","article-title":"The Effect of Dietary Lysine and Valine Fed during Lactation on Sow and Litter Performance","volume":"75","author":"Richert","year":"1997","journal-title":"J. Anim. Sci."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"467","DOI":"10.2527\/2002.802467x","article-title":"Arginine Catabolism in Lactating Porcine Mammary Tissue","volume":"80","author":"Knabe","year":"2002","journal-title":"J. Anim. Sci."},{"key":"ref_50","first-page":"7","article-title":"Sow Colostral Free Amino Acids and Their Importance for the Newborn Piglet","volume":"13","author":"Bengtsson","year":"1972","journal-title":"Acta Vet. Scand."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"1587","DOI":"10.1007\/s00726-017-2451-0","article-title":"Increases in Circulating Amino Acids with In-Feed Antibiotics Correlated with Gene Expression of Intestinal Amino Acid Transporters in Piglets","volume":"49","author":"Yu","year":"2017","journal-title":"Amino Acids"},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"329","DOI":"10.1093\/tas\/txy109","article-title":"Effects of Dietary Supplementation of L-Methionine vs. Dl-Methionine on Performance, Plasma Concentrations of Free Amino Acids and Other Metabolites, and Myogenesis Gene Expression in Young Growing Pigs","volume":"3","author":"Yang","year":"2019","journal-title":"Transl. Anim. Sci."},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"12911","DOI":"10.1021\/acs.jafc.8b03097","article-title":"Evaluation of Breed and Parity Order Effects on the Lipid Composition of Porcine Colostrum","volume":"66","author":"Luise","year":"2018","journal-title":"J. Agric. Food Chem."},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"144","DOI":"10.1016\/j.jpba.2019.05.031","article-title":"Quantitative Amino Acids Profile of Monofloral Bee Pollens by Microwave Hydrolysis and Fluorimetric High Performance Liquid Chromatography","volume":"173","author":"Themelis","year":"2019","journal-title":"J. Pharm. Biomed. Anal."},{"key":"ref_55","first-page":"28","article-title":"A Statistical Perspective on the ICH Q2A and Q2B Guidelines for Validation of Analytical Methods","volume":"19","author":"Walfish","year":"2006","journal-title":"BioPharm Int."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/27\/13\/4153\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T23:39:51Z","timestamp":1760139591000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/27\/13\/4153"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2022,6,28]]},"references-count":55,"journal-issue":{"issue":"13","published-online":{"date-parts":[[2022,7]]}},"alternative-id":["molecules27134153"],"URL":"https:\/\/doi.org\/10.3390\/molecules27134153","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2022,6,28]]}}}