{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,6,10]],"date-time":"2026-06-10T16:28:20Z","timestamp":1781108900152,"version":"3.54.1"},"reference-count":55,"publisher":"MDPI AG","issue":"14","license":[{"start":{"date-parts":[[2020,7,8]],"date-time":"2020-07-08T00:00:00Z","timestamp":1594166400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/100013276","name":"Interreg","doi-asserted-by":"publisher","award":["INTERREG V (France Wallonie Flandre) SmartBioControl project (BioScreen project)"],"award-info":[{"award-number":["INTERREG V (France Wallonie Flandre) SmartBioControl project (BioScreen project)"]}],"id":[{"id":"10.13039\/100013276","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Natural rhamnolipids are potential biocontrol agents for plant protection against bacterial and fungal diseases. In this work, we synthetized new synthetic mono-rhamnolipids (smRLs) consisting in a rhamnose connected to a simple acyl chain and differing by the nature of the link and the length of the lipid tail. We then investigated the effects of these ether, ester, carbamate or succinate smRL derivatives on Botrytis cinerea development, symptoms spreading on tomato leaves and immune responses in tomato plants. Our results demonstrate that synthetic smRLs are able to trigger early and late immunity-related plant defense responses in tomato and increase plant resistance against B. cinerea in controlled conditions. Structure-function analysis showed that chain length of the lipidic part and type of acyl chain were critical to smRLs immune activity and to the extent of symptoms caused by the fungus on tomato leaves.<\/jats:p>","DOI":"10.3390\/molecules25143108","type":"journal-article","created":{"date-parts":[[2020,7,10]],"date-time":"2020-07-10T09:45:31Z","timestamp":1594374331000},"page":"3108","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":35,"title":["Synthetic Mono-Rhamnolipids Display Direct Antifungal Effects and Trigger an Innate Immune Response in Tomato against Botrytis Cinerea"],"prefix":"10.3390","volume":"25","author":[{"given":"Mathilde","family":"Robineau","sequence":"first","affiliation":[{"name":"RIBP-EA 4707, SFR Condorcet FR CNRS 3417, University of Reims Champagne-Ardenne, 51100 Reims, France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Sarah","family":"Le Guenic","sequence":"additional","affiliation":[{"name":"UnilaSalle, Unit\u00e9 Transformations &amp; Agroressources, Universit\u00e9 d\u2019Artois, ULR7519, F-62408 B\u00e9thune, France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8531-9082","authenticated-orcid":false,"given":"Lisa","family":"Sanchez","sequence":"additional","affiliation":[{"name":"RIBP-EA 4707, SFR Condorcet FR CNRS 3417, University of Reims Champagne-Ardenne, 51100 Reims, France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ludovic","family":"Chaveriat","sequence":"additional","affiliation":[{"name":"UnilaSalle, Unit\u00e9 Transformations &amp; Agroressources, Universit\u00e9 d\u2019Artois, ULR7519, F-62408 B\u00e9thune, France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Vincent","family":"Lequart","sequence":"additional","affiliation":[{"name":"UnilaSalle, Unit\u00e9 Transformations &amp; Agroressources, Universit\u00e9 d\u2019Artois, ULR7519, F-62408 B\u00e9thune, France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0516-2466","authenticated-orcid":false,"given":"Nicolas","family":"Joly","sequence":"additional","affiliation":[{"name":"UnilaSalle, Unit\u00e9 Transformations &amp; Agroressources, Universit\u00e9 d\u2019Artois, ULR7519, F-62408 B\u00e9thune, France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Maryline","family":"Calonne","sequence":"additional","affiliation":[{"name":"Earth and Life Institute, Applied Microbiology, Mycology, Universit\u00e9 catholique de Louvain, Croix du Sud, 2 box L7.05.06, 1348 Louvain-la-Neuve, Belgium"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4284-6082","authenticated-orcid":false,"given":"C\u00e9dric","family":"Jacquard","sequence":"additional","affiliation":[{"name":"RIBP-EA 4707, SFR Condorcet FR CNRS 3417, University of Reims Champagne-Ardenne, 51100 Reims, France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"St\u00e9phane","family":"Declerck","sequence":"additional","affiliation":[{"name":"Earth and Life Institute, Applied Microbiology, Mycology, Universit\u00e9 catholique de Louvain, Croix du Sud, 2 box L7.05.06, 1348 Louvain-la-Neuve, Belgium"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7507-5910","authenticated-orcid":false,"given":"Patrick","family":"Martin","sequence":"additional","affiliation":[{"name":"UnilaSalle, Unit\u00e9 Transformations &amp; Agroressources, Universit\u00e9 d\u2019Artois, ULR7519, F-62408 B\u00e9thune, France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9583-2824","authenticated-orcid":false,"given":"Stephan","family":"Dorey","sequence":"additional","affiliation":[{"name":"RIBP-EA 4707, SFR Condorcet FR CNRS 3417, University of Reims Champagne-Ardenne, 51100 Reims, France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5138-306X","authenticated-orcid":false,"given":"Essaid","family":"Ait Barka","sequence":"additional","affiliation":[{"name":"RIBP-EA 4707, SFR Condorcet FR CNRS 3417, University of Reims Champagne-Ardenne, 51100 Reims, France"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2020,7,8]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"541","DOI":"10.1146\/annurev-phyto-080614-120114","article-title":"Understanding plant immunity as a surveillance system to detect invasion","volume":"53","author":"Cook","year":"2015","journal-title":"Annu. Rev. Phytopathol."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1016\/j.pbi.2019.02.005","article-title":"Cell surface immune receptors: The guardians of the plant\u2019s extracellular spaces","volume":"50","author":"Kanyuka","year":"2019","journal-title":"Curr. Opin. Plant. Biol."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"1602","DOI":"10.1111\/mpp.12857","article-title":"Apoplastic invasion patterns triggering plant immunity: Plasma membrane sensing at the frontline","volume":"20","author":"Schellenberger","year":"2019","journal-title":"Mol. Plant. Pathol."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"587","DOI":"10.1016\/j.tplants.2019.04.009","article-title":"Plant immunity: Thinking outside and inside the box","volume":"24","author":"Joosten","year":"2019","journal-title":"Trends Plant. Sci."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"521","DOI":"10.1016\/j.molp.2014.12.022","article-title":"Signaling mechanisms in pattern-triggered immunity (PTI)","volume":"8","author":"Bigeard","year":"2015","journal-title":"Mol. Plant."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"585","DOI":"10.1111\/nph.16088","article-title":"Properties and functions of calcium-dependent protein kinases and their relatives in Arabidopsis thaliana","volume":"224","author":"Boudsocq","year":"2019","journal-title":"New Phytol."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"711","DOI":"10.1094\/MPMI-19-0711","article-title":"Early signaling events induced by elicitors of plant defenses","volume":"19","author":"Lamotte","year":"2006","journal-title":"Mol. Plant. Microbe Interact."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"489","DOI":"10.1146\/annurev-cellbio-092910-154055","article-title":"Hormonal modulation of plant immunity","volume":"28","author":"Pieterse","year":"2012","journal-title":"Annu. Rev. Cell. Dev. Biol."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"379","DOI":"10.1146\/annurev.arplant.57.032905.105346","article-title":"A renaissance of elicitors: Perception of microbe-associated molecular patterns and danger signals by pattern-recognition receptors","volume":"60","author":"Boller","year":"2009","journal-title":"Annu. Rev. Plant. Biol."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"257","DOI":"10.1146\/annurev-phyto-080614-120106","article-title":"Function, discovery, and exploitation of plant pattern recognition receptors for broad-spectrum disease resistance","volume":"55","author":"Boutrot","year":"2017","journal-title":"Annu. Rev. Phytopathol."},{"key":"ref_11","first-page":"804","article-title":"Synthetic plant defense elicitors","volume":"5","author":"Bektas","year":"2014","journal-title":"Front. Plant. Sci."},{"key":"ref_12","first-page":"629","article-title":"Benzothiadiazole, a novel class of inducers of systemic acquired resistance, activates gene expression and disease resistance in wheat","volume":"8","author":"Gorlach","year":"1996","journal-title":"Plant. Cell"},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"71","DOI":"10.1046\/j.1365-313X.1996.10010071.x","article-title":"Benzothiadiazole induces disease resistance in Arabidopsis by activation of the systemic acquired resistance signal transduction pathway","volume":"10","author":"Lawton","year":"1996","journal-title":"Plant. J."},{"key":"ref_14","first-page":"645","article-title":"Acquired resistance in Arabidopsis","volume":"4","author":"Uknes","year":"1992","journal-title":"Plant. Cell"},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"1085","DOI":"10.2307\/3869297","article-title":"Coordinate gene activity in response to agents that induce systemic acquired resistance","volume":"3","author":"Ward","year":"1991","journal-title":"Plant. Cell"},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"444","DOI":"10.1104\/pp.15.01058","article-title":"The synthetic eicitor 2-(5-bromo-2-hydroxy-phenyl)-thiazolidine-4-carboxylic acid links plant immunity to hormesis","volume":"170","author":"Bektas","year":"2016","journal-title":"Plant. Physiol."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"333","DOI":"10.1104\/pp.108.133678","article-title":"The synthetic elicitor 3,5-dichloroanthranilic acid induces NPR1-dependent and NPR1-independent mechanisms of disease resistance in Arabidopsis","volume":"150","author":"Knoth","year":"2009","journal-title":"Plant. Physiol."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"29554","DOI":"10.1038\/srep29554","article-title":"The synthetic elicitor DPMP (2,4-dichloro-6-{(E)-[(3-methoxyphenyl)imino]methyl}phenol) triggers strong immunity in Arabidopsis thaliana and tomato","volume":"6","author":"Bektas","year":"2016","journal-title":"Sci. Rep."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"5373","DOI":"10.1128\/AEM.00724-09","article-title":"Synthetic ultrashort cationic lipopeptides induce systemic plant defense responses against bacterial and fungal pathogens","volume":"75","author":"Brotman","year":"2009","journal-title":"Appl. Environ. Microbiol."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"963","DOI":"10.1111\/mpp.12252","article-title":"The synthetic cationic lipid diC14 activates a sector of the Arabidopsis defence network requiring endogenous signalling components","volume":"16","author":"Cambiagno","year":"2015","journal-title":"Mol. Plant. Pathol."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"8534","DOI":"10.1038\/s41598-018-26838-y","article-title":"Synthetic rhamnolipid bolaforms trigger an innate immune response in Arabidopsis thaliana","volume":"8","author":"Schellenberger","year":"2018","journal-title":"Sci. Rep."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"600","DOI":"10.1016\/j.jhazmat.2018.10.050","article-title":"Biodegradability and toxicity of monorhamnolipid biosurfactant diastereomers","volume":"364","author":"Hogan","year":"2019","journal-title":"J. Hazard. Mater."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"155","DOI":"10.1016\/j.scitotenv.2016.01.066","article-title":"Mechanism-specific and whole-organism ecotoxicity of mono-rhamnolipids","volume":"548\u2013549","author":"Johann","year":"2016","journal-title":"Sci. Total Environ."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"533","DOI":"10.1016\/j.watres.2005.11.030","article-title":"Biokinetics of biodegradation of surfactants under aerobic, anoxic and anaerobic conditions","volume":"40","author":"Mohan","year":"2006","journal-title":"Water Res."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"1505","DOI":"10.3389\/fmicb.2016.01505","article-title":"Rhamnolipid biosurfactant against Fusarium verticillioides to control stalk and ear rot disease of maize","volume":"7","author":"Borah","year":"2016","journal-title":"Front. Microbiol."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"548","DOI":"10.1002\/jobm.201200801","article-title":"Rhamnolipid biosurfactant against Fusarium sacchari the causal organism of pokkah boeng disease of sugarcane","volume":"54","author":"Goswami","year":"2014","journal-title":"J. Basic Microbiol."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"1029","DOI":"10.1002\/1526-4998(200012)56:12<1029::AID-PS238>3.0.CO;2-Q","article-title":"In vivo control and in vitro antifungal activity of rhamnolipid B, a glycolipid antibiotic, against Phytophthora capsici and Colletotrichum orbiculare","volume":"56","author":"Kim","year":"2000","journal-title":"Pest Manage. Sci."},{"key":"ref_28","doi-asserted-by":"crossref","unstructured":"Monnier, N., Furlan, A.L., Buchoux, S., Deleu, M., Dauchez, M., Rippa, S., and Sarazin, C. (2019). Exploring the dual interaction of natural rhamnolipids with plant and fungal biomimetic plasma membranes through biophysical studies. Int. J. Mol. Sci., 20.","DOI":"10.3390\/ijms20051009"},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"4","DOI":"10.1094\/PDIS.1997.81.1.4","article-title":"Biosurfactants: Their identity and potential efficacy in the biological control of zoosporic plant pathogen","volume":"81","author":"Stanghellini","year":"1997","journal-title":"Plant. Dis."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"1500","DOI":"10.1002\/ps.4177","article-title":"Rhamnolipids induce oxidative stress responses in cherry tomato fruit to Alternaria alternata","volume":"72","author":"Yan","year":"2016","journal-title":"Pest. Manage. Sci."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"834","DOI":"10.1094\/PHYTO-07-19-0275-R","article-title":"Semipurified rhamnolipid mixes protect Brassica napus against Leptosphaeria maculans early infections","volume":"110","author":"Monnier","year":"2020","journal-title":"Phytopathology"},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"1170","DOI":"10.3389\/fpls.2018.01170","article-title":"Rhamnolipids from Pseudomonas aeruginosa are elicitors triggering Brassica napus protection against Botrytis cinerea without physiological disorders","volume":"9","author":"Monnier","year":"2018","journal-title":"Front. Plant. Sci."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"1630","DOI":"10.1104\/pp.112.201913","article-title":"Rhamnolipids elicit defense responses and induce disease resistance against biotrophic, hemibiotrophic, and necrotrophic pathogens that require different signaling pathways in Arabidopsis and highlight a central role for salicylic acid","volume":"160","author":"Sanchez","year":"2012","journal-title":"Plant. Physiol."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"178","DOI":"10.1111\/j.1365-3040.2008.01911.x","article-title":"Bacterial rhamnolipids are novel MAMPs conferring resistance to Botrytis cinerea in grapevine","volume":"32","author":"Varnier","year":"2009","journal-title":"Plant. Cell Environ."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"401","DOI":"10.1002\/open.201600043","article-title":"Chemical O-Glycosylations: An overview","volume":"5","author":"Das","year":"2016","journal-title":"ChemistryOpen"},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"1008","DOI":"10.1016\/j.tetasy.2014.05.012","article-title":"An efficient synthesis of novel l-rhamnose based non-ionic surfactants under controlled microwave irradiation","volume":"25","year":"2014","journal-title":"Tetrahedron: Asymmetry"},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"1830","DOI":"10.1016\/j.bmc.2017.01.042","article-title":"Synthetic analogs of rhamnolipids modulate structured biofilms formed by rhamnolipid-nonproducing mutant of Pseudomonas aeruginosa","volume":"25","author":"Zheng","year":"2017","journal-title":"Bioorg. Med. Chem."},{"key":"ref_38","unstructured":"Houlmont, J.-P., Rico-Lattes, I., Perez, E., and Bordat, P. (2005). Medicament Comprising a Reducing Alkyl-Sugar Monomer for the Treatment of Inflammatory Disorders. (WO2005041983A1), France Patent."},{"key":"ref_39","first-page":"125","article-title":"Protective effects of butylated hydroxyanisole and its analogs on the lung toxicity of butylated hydroxytoluene in mice","volume":"50","author":"Mizutani","year":"1985","journal-title":"Res. Commun. Chem. Pathol. Pharmacol."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"22","DOI":"10.2174\/1573406410666150807111029","article-title":"Synthesis, characterization, antimicrobial and antitumor activities of sucrose Octa(N-ethyl)carbamate","volume":"12","author":"Raposo","year":"2016","journal-title":"Med. Chem."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"583","DOI":"10.1016\/j.tetlet.2003.10.194","article-title":"Preparation of amphiphilic sucrose carbamates by reaction with alkyl isocyanates in water\u2013alcohol mixtures","volume":"45","author":"Christian","year":"2004","journal-title":"Tetrahedron Lett."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"5","DOI":"10.1002\/jsde.12216","article-title":"Renewable surfactants for biochemical applications and nanotechnology","volume":"22","author":"Chaveriat","year":"2019","journal-title":"J. Surfactants Deterg."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"5095","DOI":"10.3390\/ijms11125095","article-title":"Rhamnolipid biosurfactants as new players in animal and plant defense against microbes","volume":"11","author":"Vatsa","year":"2010","journal-title":"Int. J. Mol. Sci."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"143","DOI":"10.1016\/j.foodhyd.2013.10.033","article-title":"Synthesis, characterization and emulsification properties of dodecenyl succinic anhydride derivatives of gum Arabic","volume":"37","author":"Wang","year":"2014","journal-title":"Food Hydrocoll."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"888","DOI":"10.1016\/j.carbpol.2009.07.017","article-title":"Surface esterification of corn starch films: Reaction with dodecenyl succinic anhydride","volume":"78","author":"Zhou","year":"2009","journal-title":"Carbohydr. Polym."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"1397","DOI":"10.3389\/fpls.2018.01397","article-title":"Impacts of Paraburkholderia phytofirmans strain PsJN on tomato (Lycopersicon esculentum L.) under high temperature","volume":"9","author":"Issa","year":"2018","journal-title":"Front. Plant. Sci."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"1159","DOI":"10.1016\/j.tetlet.2015.01.091","article-title":"A stereocontrolled synthesis of the hydrophobic moiety of rhamnolipids","volume":"56","author":"Menhour","year":"2015","journal-title":"Tetrahedron Lett."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"265","DOI":"10.1046\/j.1365-313X.1999.00265.x","article-title":"Plants have a sensitive perception system for the most conserved domain of bacterial flagellin","volume":"18","author":"Felix","year":"1999","journal-title":"Plant. J."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"23","DOI":"10.1016\/j.biochi.2016.04.001","article-title":"Interactions of sugar-based bolaamphiphiles with biomimetic systems of plasma membranes","volume":"130","author":"Nasir","year":"2016","journal-title":"Biochimie"},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"1824","DOI":"10.1111\/j.1462-5822.2011.01664.x","article-title":"The bacterial lipopeptide surfactin targets the lipid fraction of the plant plasma membrane to trigger immune-related defence responses","volume":"13","author":"Henry","year":"2011","journal-title":"Cell. Microbiol."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"456","DOI":"10.1094\/MPMI-22-4-0456","article-title":"Insights into the defense-related events occurring in plant cells following perception of surfactin-type lipopeptide from Bacillus subtilis","volume":"22","author":"Jourdan","year":"2009","journal-title":"Mol. Plant.-Microbe Interact."},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"1608","DOI":"10.1038\/s41467-020-14949-y","article-title":"A lipophilic cation protects crops against fungal pathogens by multiple modes of action","volume":"11","author":"Steinberg","year":"2020","journal-title":"Nature Commun."},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"1265","DOI":"10.1002\/jobm.201500220","article-title":"Antifungal properties of rhamnolipid produced by Pseudomonas aeruginosa DS9 against Colletotrichum falcatum","volume":"55","author":"Goswami","year":"2015","journal-title":"J. Basic Microbiol."},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"12907","DOI":"10.1038\/s41598-017-13424-x","article-title":"Sodium chloride effect on the aggregation behaviour of rhamnolipids and their antifungal activity","volume":"7","author":"Rodrigues","year":"2017","journal-title":"Sci. Rep."},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"233","DOI":"10.2323\/jgam.2016.04.004","article-title":"Antifungal activity of rhamnolipids against dimorphic fungi","volume":"62","author":"Sha","year":"2016","journal-title":"J. Gen. Appl. Microbiol."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/25\/14\/3108\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T09:48:47Z","timestamp":1760176127000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/25\/14\/3108"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2020,7,8]]},"references-count":55,"journal-issue":{"issue":"14","published-online":{"date-parts":[[2020,7]]}},"alternative-id":["molecules25143108"],"URL":"https:\/\/doi.org\/10.3390\/molecules25143108","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2020,7,8]]}}}