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The antifungal activity of all compounds against the phytopathogens Botrytis cinerea and Phytophthora cinnamomi, two important plant pathogens associated with substantial agricultural and economic losses worldwide, was evaluated in vitro using a mycelial growth inhibition assay. Dose\u2013response treatment of the data indicates that (E)-2-((3,7-dimethylocta-2,6-dien-1-yl)oxy)-5-hydroxybenzaldehyde (19) is the most active compound exhibiting EC50 values of 83 \u00b5g\/mL and 7.34 \u00b5g\/mL against B. cinerea and P. cinnamomi, respectively. To gain insight into the molecular basis of the observed antifungal activity, molecular docking studies were performed targeting the active site of succinate dehydrogenase (SDH, PDB ID: 2FBW), a key enzyme in the mitochondrial respiratory chain and a validated fungicide target. The calculated docking scores ranged from \u22126.0 to \u22127.5 kcal\/mol, with compound 19 showing the highest binding affinity. Docking analysis reveals that compound 19 is stabilized within the SDH binding pocket through a network of hydrogen bonding and \u03c0\u2013cation interactions involving the heme prosthetic group and key amino acid residues, providing a plausible structural rationale for its high antifungal activity, particularly against P. cinnamomi.<\/jats:p>","DOI":"10.3390\/molecules31193481","type":"journal-article","created":{"date-parts":[[2026,9,29]],"date-time":"2026-09-29T12:09:25Z","timestamp":1790683765000},"page":"3481","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Design and Synthesis of Geranylated Benzaldehydes: Evaluation of Antifungal Activities Against Botrytis cinerea and Phytophthora cinnamomi"],"prefix":"10.3390","volume":"31","author":[{"given":"Ligia","family":"Llovera","sequence":"first","affiliation":[{"name":"Departamento de Qu\u00edmica, Universidad T\u00e9cnica Federico Santa Mar\u00eda, Av. 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(2016). Plant hosts of Botrytis spp. Botrytis\u2014The Fungus, the Pathogen and Its Management in Agricultural Systems, Springer.","DOI":"10.1007\/978-3-319-23371-0_20"},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"561","DOI":"10.1111\/j.1364-3703.2007.00417.x","article-title":"Botrytis Cinerea: The Cause of Grey Mould Disease","volume":"8","author":"Williamson","year":"2007","journal-title":"Mol. Plant Pathol."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"589","DOI":"10.1111\/j.1364-3703.2005.00308.x","article-title":"Phytophthora Cinnamomi","volume":"6","author":"Hardham","year":"2005","journal-title":"Mol. Plant Pathol."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"182","DOI":"10.3767\/persoonia.2018.40.08","article-title":"Canker and Decline Diseases Caused by Soil- and Airborne Phytophthora Species in Forests and Woodlands","volume":"40","author":"Jung","year":"2018","journal-title":"Persoonia"},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"1022","DOI":"10.1093\/jxb\/erac448","article-title":"Cellobiose Elicits Immunity in Lettuce Conferring Resistance to Botrytis Cinerea","volume":"74","author":"He","year":"2023","journal-title":"J. Exp. Bot."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"455","DOI":"10.1094\/PHYTO-07-20-0313-IA","article-title":"Advances in Understanding Fungicide Resistance in Botrytis Cinerea in China","volume":"111","author":"Shao","year":"2021","journal-title":"Phytopathology"},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"1711","DOI":"10.1021\/np50114a015","article-title":"Biological. Effects of Prenylated Hydroquinones: Structure-Activity Relationship Studies Salvatore in Antimicrobial, Brine Shrimp, and Fish Lethality Assays","volume":"57","author":"Iodice","year":"1994","journal-title":"J. Nat. Prod."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"1444","DOI":"10.1021\/np50123a017","article-title":"Bioactive Prenylhydroquinone Sulfates and a Novel C 31 Furanoterpene Alcohol Sulfate from the Marine Sponge, Ircinia sp","volume":"58","author":"Bifulco","year":"1995","journal-title":"J. Nat. Prod."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"2330","DOI":"10.1021\/acs.orglett.9b00616","article-title":"Multidomain P450 Epoxidase and a Terpene Cyclase from the Ascochlorin Biosynthetic Pathway in Fusarium sp","volume":"21","author":"Quan","year":"2019","journal-title":"Org. Lett."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"7701","DOI":"10.1021\/jf051021l","article-title":"Bioactive Metabolites from the Fungus Nectria Galligena, the Main Apple Canker Agent in Chile","volume":"53","author":"Theoduloz","year":"2005","journal-title":"J. Agric. Food Chem."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"297","DOI":"10.1007\/s10126-004-3150-x","article-title":"Inhibitory Effects of Mediterranean Sponge Extracts and Metabolites on Larval Settlement of the Barnacle Balanus Amphitrite","volume":"7","author":"Aldred","year":"2005","journal-title":"Mar. Biotechnol."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"1079","DOI":"10.1071\/CH9931079","article-title":"Studies of Australian Ascidians. 3. A New Tetrahydrocannabinol Derivative from the Ascidian Synoicum Castellatum","volume":"46","author":"Carroll","year":"1993","journal-title":"Aust. J. Chem."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"105","DOI":"10.1071\/CH9820105","article-title":"Lipid and Terpenoid Metabolites of the Gorgonian Plexaura Flava","volume":"35","author":"Ravi","year":"1982","journal-title":"Aust. J. Chem."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"4449","DOI":"10.1016\/S0040-4039(01)86615-6","article-title":"Simple Prenylated Hydroquinone Derivatives from the Marine Urochordate Aplidium Californicum. Natural Anticancer and Antimutagenic Agents","volume":"20","author":"Howard","year":"1979","journal-title":"Tetrahedron Lett."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"556","DOI":"10.1021\/np50033a035","article-title":"A Terpenehydroquinone from the Marine Ascidian Aplidium Constellatum","volume":"47","author":"Targett","year":"1984","journal-title":"J. Nat. Prod."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"621","DOI":"10.1002\/hlca.19870700316","article-title":"Verapliquinones: Novel Diprenylquinones from an Aplidium sp. (Ascidiacea) of Ile-Verte Waters, Brittany","volume":"70","author":"Guella","year":"1987","journal-title":"Helv. Chim. Acta"},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"497","DOI":"10.1039\/np9931000497","article-title":"Marine Natural Products","volume":"10","author":"Faulkner","year":"1993","journal-title":"Nat. Prod. Rep."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"1328","DOI":"10.1021\/np020176+","article-title":"New Meroterpenoids from the Ascidian Aplidium Conicum","volume":"65","author":"Garrido","year":"2002","journal-title":"J. Nat. Prod."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"1567","DOI":"10.1016\/S0031-9422(00)98500-5","article-title":"Geranylhydroquinone: A Contact Allergen from Trichomes of Phacelia Crenulata","volume":"18","author":"Reynolds","year":"1979","journal-title":"Phytochemistry"},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"4057","DOI":"10.1002\/cber.19681011207","article-title":"\u00dcber Die Inhaltsstoffe von Pirolaceen, XV Zur Struktur Des Pirolatins","volume":"101","author":"Inouye","year":"1968","journal-title":"Chem. Ber."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"272","DOI":"10.1111\/j.1600-0536.1980.tb04929.x","article-title":"A Potent Contact Allergen of Phacelia (Hydrophyllaceae)","volume":"6","author":"Reynolds","year":"1980","journal-title":"Contact Dermat."},{"key":"ref_22","unstructured":"Fenical, W., Weber, H.H., and Ruggierri, C.D. (1974, January 17\u201321). Geranyl hydroquinone, a cancer-protective agent from the tunicate Aplidium sp. In Proceeding of the 4th Food Drugs from the Sea, Washington, DC, USA."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"1219","DOI":"10.4067\/S0717-97072012000300005","article-title":"Synthesis and Cytotoxic Activity of Geranylmethoxyhydroquinone Derivatives","volume":"3","author":"Baeza","year":"2012","journal-title":"J. Chil. Chem. Soc."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"22","DOI":"10.1016\/j.cbi.2016.01.016","article-title":"Antiproliferative Effect and Apoptotic Activity of Linear Geranylphenol Derivatives from Phloroglucinol and Orcinol","volume":"247","author":"Taborga","year":"2016","journal-title":"Chem. Biol. Interact."},{"key":"ref_25","doi-asserted-by":"crossref","unstructured":"Edrich, E., Young, L., Spencer, J., Mcgown, A., and Moore, A. (2025). Novel Mitochondrial-Targeted Alkyl Chains Act as Fungal Specific Inhibitors of C. Neoformans. Front. Microbiol., 15.","DOI":"10.3389\/fmicb.2024.1505308"},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"702","DOI":"10.1021\/acs.jnatprod.8b00435","article-title":"Prenylated Phenolic Compounds from the Leaves of Sabia Limoniacea and Their Antiviral Activities against Porcine Epidemic Diarrhea Virus","volume":"82","author":"Cho","year":"2019","journal-title":"J. Nat. Prod."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"19130","DOI":"10.3390\/ijms160819130","article-title":"Synthesis and in Vitro Antifungal Activity against Botrytis Cinerea of Geranylated Phenols and Their Phenyl Acetate Derivatives","volume":"16","author":"Soto","year":"2015","journal-title":"Int. J. Mol. Sci."},{"key":"ref_28","doi-asserted-by":"crossref","unstructured":"Soto, M., Estevez-Braun, A., Amesty, \u00c1., Kluepfel, J., Restrepo, S., Diaz, K., Espinoza, L., Olea, A.F., and Taborga, L. (2021). Synthesis and Fungicidal Activity of Hydrated Geranylated Phenols against Botrytis Cinerea. Molecules, 26.","DOI":"10.3390\/molecules26226815"},{"key":"ref_29","doi-asserted-by":"crossref","unstructured":"Soto, M., Taborga, L., Ch\u00e1vez, M., D\u00edaz, K., Olea, A., and Espinoza, L. (2016). Synthesis of New Hydrated Geranylphenols and In Vitro Antifungal Activity against Botrytis Cinerea. Int. J. Mol. Sci., 17.","DOI":"10.3390\/ijms17060840"},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"1512","DOI":"10.3390\/molecules19021512","article-title":"Synthesis of Linear Geranylphenols and Their Effect on Mycelial Growth of Plant Pathogen Botrytis Cinerea","volume":"19","author":"Espinoza","year":"2014","journal-title":"Molecules"},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"6890","DOI":"10.1021\/acs.jafc.5b01920","article-title":"Effect of Polymer Micelles on Antifungal Activity of Geranylorcinol Compounds against Botrytis Cinerea","volume":"63","author":"Taborga","year":"2015","journal-title":"J. Agric. Food Chem."},{"key":"ref_32","doi-asserted-by":"crossref","unstructured":"Ch\u00e1vez, M., Soto, M., Cimino, F., Olea, A., Espinoza, L., Diaz, K., and Taborga, L. (2018). In Vitro Antifungal Activity of New and Known Geranylated Phenols against Phytophthora Cinnamomi Rands. Int. J. Mol. Sci., 19.","DOI":"10.3390\/ijms19061601"},{"key":"ref_33","doi-asserted-by":"crossref","unstructured":"Bouillaud, F. (2023). Inhibition of Succinate Dehydrogenase by Pesticides (SDHIs) and Energy Metabolism. Int. J. Mol. Sci., 24.","DOI":"10.3390\/ijms24044045"},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"3496","DOI":"10.1021\/acsinfecdis.3c00655","article-title":"Identification of Chemical Scaffolds That Inhibit the Mycobacterium Tuberculosis Respiratory Complex Succinate Dehydrogenase","volume":"10","author":"Adolph","year":"2024","journal-title":"ACS Infect. Dis."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"341","DOI":"10.1007\/s10646-024-02849-6","article-title":"Ecotoxicological Impact of Succinate Dehydrogenase Inhibitor (SDHI) Fungicides on Non-Targeted Organisms: A Review","volume":"34","author":"Dwivedi","year":"2025","journal-title":"Ecotoxicology"},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"160","DOI":"10.1016\/j.pestbp.2019.02.017","article-title":"Design, Synthesis, and Antifungal Activity of Carboxamide Derivatives Possessing 1, 2, 3-Triazole as Potential Succinate Dehydrogenase Inhibitors","volume":"156","author":"Yan","year":"2019","journal-title":"Pestic. Biochem. Physiol. J."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"643","DOI":"10.1016\/j.cropro.2010.02.019","article-title":"Progress in Understanding Molecular Mechanisms and Evolution of Resistance to Succinate Dehydrogenase Inhibiting (SDHI) Fungicides in Phytopathogenic Fungi","volume":"29","author":"Avenot","year":"2010","journal-title":"Crop Prot."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"108219","DOI":"10.1016\/j.envint.2023.108219","article-title":"SDHi Fungicides: An Example of Mitotoxic Pesticides Targeting the Succinate Dehydrogenase Complex","volume":"180","author":"Duarte","year":"2023","journal-title":"Environ. Int."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"140679","DOI":"10.1016\/j.bbapap.2021.140679","article-title":"Crystallographic Investigation of the Ubiquinone Binding Site of Respiratory Complex II and Its Inhibitors","volume":"1869","author":"Huang","year":"2022","journal-title":"Biochim Biophys Acta Proteins Proteom"},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"973","DOI":"10.1021\/np034051w","article-title":"Hyperjovinols A and B: Two New Phloroglucinol Derivatives from Hypericum Jovis with Antioxidant Activity in Cell Cultures","volume":"67","author":"Athanasas","year":"2004","journal-title":"J. Nat. Prod."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"9151","DOI":"10.1021\/jo201654h","article-title":"Anti-Inflammatory and Antimalarial Meroterpenoids from the New Zealand Ascidian Aplidium Scabellum","volume":"76","author":"Chan","year":"2011","journal-title":"J. Org. Chem."},{"key":"ref_42","first-page":"70","article-title":"Evaluation of Cancer Preventive Activity and Structure-Activity Relationships of 3-Demethylubiquinone Q2, Isolated from the Ascidian Aplidium Glabrum, and Its Synthetic Analogues","volume":"23","author":"Fedorov","year":"2006","journal-title":"Pharmaceutical"},{"key":"ref_43","doi-asserted-by":"crossref","unstructured":"Ng, C.H., Rullah, K., Abas, F., Lam, K.W., Ismail, I.S., Jamaludin, F., and Shaari, K. (2018). Hits-to-Lead Optimization of the Natural Compound 2,4,6-Trihydroxy-3-Geranyl-Acetophenone (Thga) as a Potent Lox Inhibitor: Synthesis, Structure-Activity Relationship (Sar) Study, and Computational Assignment. Molecules, 23.","DOI":"10.3390\/molecules23102509"},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"178","DOI":"10.1016\/j.ejmech.2017.09.062","article-title":"Synthesis and Antibacterial Activity of New Symmetric Polyoxygenated Dibenzofurans","volume":"141","author":"Pantoja","year":"2017","journal-title":"Eur. J. Med. Chem."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"112649","DOI":"10.1016\/j.ejmech.2020.112649","article-title":"Synthesis of Natural 3\u2032-Prenylchalconaringenin and Biological Evaluation of Ameliorating Non-Alcoholic Fatty Liver Disease and Metabolic Syndrome","volume":"205","author":"Zhang","year":"2020","journal-title":"Eur. J. Med. Chem."},{"key":"ref_46","doi-asserted-by":"crossref","unstructured":"N\u00fa\u00f1ez, G., Llovera, L., Arrieche, D., Berrios, R., Soto, M., Osorio-Olivares, M., Olea, A.F., Sarmiento, E., Gonz\u00e1lez, A., and Carrasco, H. (2025). Evaluation of Phytotoxic and Cytotoxic Effects of Prenylated Phenol Derivatives on Tomato Plants (Solanum lycopersicum L.) and Botrytis Cinerea B-05 Spores. Plants, 14.","DOI":"10.3390\/plants14213277"},{"key":"ref_47","doi-asserted-by":"crossref","unstructured":"Laiche, M.H., and Barlow, J.W. (2025). Recent Advances in the Synthesis and Biological Applications of Prenylated Chalcones. Int. J. Mol. Sci., 26.","DOI":"10.3390\/ijms26209845"},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"421","DOI":"10.1007\/s00253-024-13254-8","article-title":"Prenylation of Aromatic Amino Acids and Plant Phenolics by an Aromatic Prenyltransferase from Rasamsonia Emersonii","volume":"108","author":"Chunkrua","year":"2024","journal-title":"Appl. Microbiol. Biotechnol."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"791","DOI":"10.1038\/s41557-023-01430-8","article-title":"Chelation Enables Selectivity Control in Enantioconvergent Suzuki\u2013Miyaura Cross-Couplings on Acyclic Allylic Systems","volume":"16","author":"Stojalnikova","year":"2024","journal-title":"Nat. Chem."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"412","DOI":"10.1039\/C3CS60197H","article-title":"Selection of Boron Reagents for Suzuki\u2013Miyaura Coupling","volume":"43","author":"Lennox","year":"2014","journal-title":"Chem. Soc. Rev."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"9145","DOI":"10.1021\/jacs.6b03283","article-title":"Protodeboronation of Heteroaromatic, Vinyl and Cyclopropyl Boronic Acids: PH\u2013Rate Profiles, Autocatalysis and Disproportionation","volume":"138","author":"Cox","year":"2016","journal-title":"J. Am. Chem. Soc."},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"4401","DOI":"10.1021\/jacs.8b00400","article-title":"Elucidating the Role of the Boronic Esters in the Suzuki\u2013Miyaura Reaction: Structural, Kinetic, and Computational Investigations","volume":"140","author":"Thomas","year":"2018","journal-title":"J. Am. Chem. Soc."},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"425","DOI":"10.1016\/S0040-4020(00)00927-3","article-title":"Chromatography with Silver Nitrate","volume":"57","author":"Williams","year":"2001","journal-title":"Tetrahedron"},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"1133","DOI":"10.1016\/j.tet.2016.01.004","article-title":"Chromatography with Silver Nitrate: Part 2","volume":"72","author":"Mander","year":"2016","journal-title":"Tetrahedron"},{"key":"ref_55","doi-asserted-by":"crossref","unstructured":"Vrkoslav, V., Hork\u00e1, P., Jindrich, J., Bude\u0161\u00ednsk\u00fd, M., and Cvacka, J. (2023). Silver Ion High-Performance Liquid Chromatography\u2014Atmospheric Pressure Chemical Ionization Mass Spectrometry: A Tool for Analyzing Cuticular Hydrocarbons. Molecules, 28.","DOI":"10.3390\/molecules28093794"},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"570","DOI":"10.5423\/PPJ.NT.05.2016.0114","article-title":"Effectiveness of Different Classes of Fungicides on Botrytis Cinerea Causing Gray Mold on Fruit and Vegetables","volume":"32","author":"Kim","year":"2016","journal-title":"Plant Pathol. J."},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"1337","DOI":"10.1002\/ps.1820","article-title":"Inhibitory Effect of Bionic Fungicide 2-Allylphenol on Botrytis Cinerea (Pers. Ex Fr.) in Vitro","volume":"65","author":"Gong","year":"2009","journal-title":"Pest. Manag. Sci."},{"key":"ref_58","doi-asserted-by":"crossref","unstructured":"Olea, A.F., Espinoza, L., Sedan, C., Thomas, M., Mart\u00ednez, R., Mellado, M., Carrasco, H., and Diaz, K. (2019). Synthesis and In Vitro Growth Inhibition of 2-Allylphenol Derivatives Against Phythopthora Cinnamomi Rands Andr\u00e9s. Molecules, 24.","DOI":"10.3390\/molecules24224196"},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"2024","DOI":"10.1094\/PDIS-09-18-1698-RE","article-title":"New Oomycota Fungicides With Activity Against Phytophthora Cinnamomi and Their Potential Use for Managing Avocado Root Rot in California","volume":"103","author":"Belisle","year":"2024","journal-title":"Plant Dis."},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"137","DOI":"10.1590\/S1982-56762010000300001","article-title":"Antifungal Activity of Eugenol against Botrytis Cinerea","volume":"35","author":"Wang","year":"2010","journal-title":"Trop. Plant pathol."},{"key":"ref_61","doi-asserted-by":"crossref","unstructured":"Olea, F., Bravo, A., Mart, R., Thomas, M., Sedan, C., Espinoza, L., Zambrano, E., Carvajal, D., Silva-moreno, E., and Carrasco, H. (2019). Antifungal Activity of Eugenol Derivatives against Botrytis Cinerea. Molecules, 24.","DOI":"10.3390\/molecules24071239"},{"key":"ref_62","unstructured":"Dassault Syst\u00e8mes (2021). BIOVIA, Dassault Syst\u00e8mes. Discovery Studio Modeling Environment, Release 2021."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/31\/19\/3481\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,9,29]],"date-time":"2026-09-29T12:12:18Z","timestamp":1790683938000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/31\/19\/3481"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,9,29]]},"references-count":62,"journal-issue":{"issue":"19","published-online":{"date-parts":[[2026,10]]}},"alternative-id":["molecules31193481"],"URL":"https:\/\/doi.org\/10.3390\/molecules31193481","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,9,29]]}}}