{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,6,18]],"date-time":"2026-06-18T22:02:51Z","timestamp":1781820171462,"version":"3.54.5"},"reference-count":68,"publisher":"MDPI AG","issue":"3","license":[{"start":{"date-parts":[[2021,1,27]],"date-time":"2021-01-27T00:00:00Z","timestamp":1611705600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"IDEASS: Approcci innovativi nella difesa delle colture agrarie: studi in silico, selezione e sintesi di composti a ridotta tossicit\u00e0 per il contenimento di funghi","award":["RASSR73282"],"award-info":[{"award-number":["RASSR73282"]}]},{"name":"SSPIT: Selection of sustainable phenolic inhibitors of trichothecene biosynthesis: in vitro studies and computational insight into the structure- activity relationship\u201d.","award":["CUP: J86C16000070009"],"award-info":[{"award-number":["CUP: J86C16000070009"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Onychomycosis is a common nail infection mainly caused by species belonging to the F. oxysporum, F. solani, and F. fujikuroi species complexes. The aim of this study was to evaluate the in vitro susceptibility of six representative strains of clinically relevant Fusarium spp. toward a set of natural-occurring hydroxycinnamic acids and their derivatives with the purpose to develop naturally occurring products in order to cope with emerging resistance phenomena. By introducing a prenylated chain at one of the hydroxy groups of trans-cinnamic acids 1\u20133, ten prenylated derivatives (coded 4\u201313) were preliminarily investigated in solid Fusarium minimal medium (FMM). Minimal inhibitory concentration (MIC) and lethal dose 50 (LD50) values were then determined in liquid FMM for the most active selected antifungal p-coumaric acid 3,3\u2032-dimethyl allyl ester 13, in comparison with the conventional fungicides terbinafine (TRB) and amphotericin B (AmB), through the quantification of the fungal growth. Significant growth inhibition was observed for prenylated derivatives 4\u201313, evidencing ester 13 as the most active. This compound presented MIC and LD50 values (62\u2013250 \u00b5M and 7.8\u2013125 \u00b5M, respectively) comparable to those determined for TRB and AmB in the majority of the tested pathogenic strains. The position and size of the prenylated chain and the presence of a free phenol OH group appear crucial for the antifungal activity. This work represents the first report on the activity of prenylated cinnamic esters and ethers against clinical Fusarium spp. and opens new avenues in the development of alternative antifungal compounds based on a drug repositioning strategy.<\/jats:p>","DOI":"10.3390\/molecules26030658","type":"journal-article","created":{"date-parts":[[2021,1,27]],"date-time":"2021-01-27T12:20:26Z","timestamp":1611750026000},"page":"658","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":15,"title":["Prenylated Trans-Cinnamic Esters and Ethers against Clinical Fusarium spp.: Repositioning of Natural Compounds in Antimicrobial Discovery"],"prefix":"10.3390","volume":"26","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-4766-7251","authenticated-orcid":false,"given":"Safa","family":"Oufensou","sequence":"first","affiliation":[{"name":"Dipartimento di Agraria, Universit\u00e0 degli Studi di Sassari, Via E. De Nicola 9, 07100 Sassari, Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Stefano","family":"Casalini","sequence":"additional","affiliation":[{"name":"Dipartimento di Agraria, Universit\u00e0 degli Studi di Sassari, Via E. De Nicola 9, 07100 Sassari, Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3213-3089","authenticated-orcid":false,"given":"Virgilio","family":"Balmas","sequence":"additional","affiliation":[{"name":"Dipartimento di Agraria, Universit\u00e0 degli Studi di Sassari, Via E. De Nicola 9, 07100 Sassari, Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8749-6093","authenticated-orcid":false,"given":"Paola","family":"Carta","sequence":"additional","affiliation":[{"name":"Istituto CNR di Chimica Biomolecolare, Traversa La Crucca 3, 07100 Sassari, Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Wiem","family":"Chtioui","sequence":"additional","affiliation":[{"name":"Dipartimento di Agraria, Universit\u00e0 degli Studi di Sassari, Via E. De Nicola 9, 07100 Sassari, Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8776-9271","authenticated-orcid":false,"given":"Maria A.","family":"Dettori","sequence":"additional","affiliation":[{"name":"Istituto CNR di Chimica Biomolecolare, Traversa La Crucca 3, 07100 Sassari, Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Davide","family":"Fabbri","sequence":"additional","affiliation":[{"name":"Istituto CNR di Chimica Biomolecolare, Traversa La Crucca 3, 07100 Sassari, Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2459-5833","authenticated-orcid":false,"given":"Quirico","family":"Migheli","sequence":"additional","affiliation":[{"name":"Dipartimento di Agraria, Universit\u00e0 degli Studi di Sassari, Via E. De Nicola 9, 07100 Sassari, Italy"},{"name":"Nucleo di Ricerca sulla Desertificazione, Universit\u00e0 degli Studi di Sassari, Via E. De Nicola 9, 07100 Sassari, Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Giovanna","family":"Delogu","sequence":"additional","affiliation":[{"name":"Istituto CNR di Chimica Biomolecolare, Traversa La Crucca 3, 07100 Sassari, Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2021,1,27]]},"reference":[{"key":"ref_1","first-page":"7228","article-title":"Polyphenolic phytochemicals in cancer prevention and therapy: Bioavailability versus bioefficacy","volume":"65","author":"Estrela","year":"2017","journal-title":"J. Agric. Food Chem."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"89","DOI":"10.1016\/j.mib.2018.08.004","article-title":"Opportunities for plant natural products in infection control","volume":"45","author":"Salam","year":"2018","journal-title":"Curr. Opin. Microbiol."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"3205","DOI":"10.1002\/jsfa.6156","article-title":"In situ antioxidant and antimicrobial activities of naturally occurring caffeic acid, p-coumaric acid and rutin, using food systems","volume":"93","year":"2013","journal-title":"J. Sci. Food Agric."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"865","DOI":"10.1007\/s11101-020-09689-2","article-title":"Biosynthesis and metabolic actions of simple phenolic acids in plants","volume":"19","author":"Marchiosi","year":"2020","journal-title":"Phytochem. Rev."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"377","DOI":"10.1093\/jxb\/ern277","article-title":"Class III peroxidases in plant defence reactions","volume":"60","author":"Almagro","year":"2009","journal-title":"J. Exp. Bot."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"5816","DOI":"10.1016\/j.bmc.2010.06.090","article-title":"Lipophilic phenolic antioxidants: Correlation between antioxidant profile, partition coefficients and redox properties","volume":"18","author":"Roleira","year":"2010","journal-title":"Bioorg. Med. Chem."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"10877","DOI":"10.1021\/jf301807g","article-title":"Biosynthesis, natural sources, dietary intake, pharmacokinetic properties, and biological activities of hydroxycinnamic acids","volume":"60","author":"Khalifa","year":"2012","journal-title":"J. Agric. Food Chem."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"86","DOI":"10.1016\/j.btre.2014.09.002","article-title":"Potential applications of ferulic acid from natural sources","volume":"4","author":"Kumar","year":"2014","journal-title":"Biotechnol. Rep."},{"key":"ref_9","unstructured":"Preedy, V.R. (2015). Chapter 74\u2014Caffeic and ferulic acid derivatives: Use in Breast Cancer. Coffee in Health and Disease Prevention, Academic Press."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"275","DOI":"10.1080\/10408398.2020.1726868","article-title":"Use of natural resources from Southern Brazil as a strategy to mitigate fungal contamination","volume":"61","author":"Furlong","year":"2020","journal-title":"Crit. Rev. Food Sci. Nutr."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"1542","DOI":"10.1016\/j.foodchem.2009.01.059","article-title":"Extraction and purification of ferulic acid from flax shives, wheat and corn bran by alkaline hydrolysis and pressurised solvents","volume":"115","author":"Buranov","year":"2009","journal-title":"Food Chem."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"1648","DOI":"10.1021\/acs.jnatprod.7b00250","article-title":"Chemoenzymatic synthesis and \u03b1-Glucosidase inhibitory activity of dimeric neolignans inspired by magnolol","volume":"80","author":"Pulvirenti","year":"2017","journal-title":"J. Nat. Prod."},{"key":"ref_13","first-page":"1055","article-title":"The Multiple faces of eugenol. A versatile starting material and building block for organic and bio-organic synthesis and a convenient precursor toward bio-based fine chemicals","volume":"26","author":"Kaufman","year":"2015","journal-title":"J. Braz. Chem. Soc."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"204","DOI":"10.2174\/092986732102131206115810","article-title":"Curcumin and curcumin-like molecules: From Spice to Drugs","volume":"21","author":"Marchiani","year":"2014","journal-title":"Curr. Med. Chem."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"4436","DOI":"10.2174\/09298673113209990141","article-title":"Antioxidant properties of hydroxycinnamic acids: A review of structure activity relationships","volume":"20","author":"Garrido","year":"2013","journal-title":"Curr. Med. Chem."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"1449","DOI":"10.1021\/jm101510d","article-title":"Design, synthesis, and biological evaluation of new cinnamic derivatives as antituberculosis agents","volume":"54","author":"De","year":"2011","journal-title":"J. Med. Chem."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"106066","DOI":"10.1016\/j.ultras.2020.106066","article-title":"Confocal lens focused piezoelectric lithotripter","volume":"103","author":"Thomas","year":"2020","journal-title":"Ultrasonics."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"48","DOI":"10.1111\/myc.12273","article-title":"Spectrum of Fusarium infections in tropical dermatology evidenced by multilocus sequencing typing diagnostics","volume":"58","author":"Feng","year":"2015","journal-title":"Mycoses"},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"1491","DOI":"10.1007\/s10096-013-1924-7","article-title":"Fusariosis, a complex infection caused by a high diversity of fungal species refractory to treatment","volume":"32","author":"Guarro","year":"2013","journal-title":"Eur. J. Clin. Microbiol. Infect. Dis."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"1076","DOI":"10.1128\/JCM.01765-09","article-title":"Molecular phylogenetic diversity of dermatologic and other human pathogenic Fusaria from hospitals in Northern and Central Italy","volume":"48","author":"Migheli","year":"2010","journal-title":"J. Clin. Microbiol."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"936","DOI":"10.1016\/j.fgb.2009.08.006","article-title":"A two-locus DNA sequence database for typing plant and human pathogens within the Fusarium oxysporum species complex","volume":"46","author":"Gueidan","year":"2009","journal-title":"Fungal Genet. Biol."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"1275","DOI":"10.1111\/ijd.12906","article-title":"Fusarium onychomycosis: Prevalence, clinical presentations, response to itraconazole and terbinafine pulse therapy, and 1-year follow-up in nine cases","volume":"54","author":"Ranawaka","year":"2015","journal-title":"Int. J. Dermatol."},{"key":"ref_23","first-page":"70","article-title":"Onychomycosis by molds. Report of 78 cases","volume":"17","author":"Bonifaz","year":"2007","journal-title":"Eur. J. Dermatol."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"695","DOI":"10.1128\/CMR.00014-07","article-title":"Fusarium infections in immunocompromised patients","volume":"20","author":"Nucci","year":"2007","journal-title":"Clin. Microbiol. Rev."},{"key":"ref_25","first-page":"762","article-title":"Onychomycosis: Current trends in diagnosis and treatment","volume":"88","author":"Westerberg","year":"2013","journal-title":"Am. Fam. Physician"},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"294","DOI":"10.1053\/j.jfas.2008.12.012","article-title":"Efficacy of debridement alone versus debridement combined with topical antifungal nail lacquer for the treatment of pedal onychomycosis: A randomized, controlled trial","volume":"48","author":"Malay","year":"2009","journal-title":"J. Foot Ankle Surg."},{"key":"ref_27","unstructured":"(2009). Antifungal drugs. Treat Guidel Med Lett., 7, 95\u2013102. Available online: https:\/\/secure.medicalletter.org\/TG-article-88a."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"272","DOI":"10.1016\/S0966-842X(03)00117-3","article-title":"Antifungal agents: Mechanisms of action","volume":"11","author":"Odds","year":"2003","journal-title":"Trends Microbiol."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"459","DOI":"10.2174\/138920009788898019","article-title":"Amphotericin B and its new derivatives\u2014Mode of action","volume":"10","author":"Baginski","year":"2009","journal-title":"Curr. Drug Metab."},{"key":"ref_30","first-page":"1068","article-title":"Specific antifungal susceptibility profiles of opportunists in the Fusarium fujikuroi complex","volume":"70","author":"Hoog","year":"2015","journal-title":"J. Antimicrob. Chemother."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"1890","DOI":"10.1128\/JCM.02415-10","article-title":"Accurate and practical identification of 20 Fusarium species by seven-locus sequence analysis and reverse line blot hybridization, and an in vitro antifungal susceptibility study","volume":"49","author":"Wang","year":"2011","journal-title":"J. Clin. Microbiol."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"1463","DOI":"10.1128\/JCM.02467-08","article-title":"Less-frequent Fusarium species of clinical interest: Correlation between morphological and molecular identification and antifungal susceptibility","volume":"47","author":"Azor","year":"2009","journal-title":"J. Clin. Microbiol."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"e1005464","DOI":"10.1371\/journal.ppat.1005464","article-title":"Fusarium: Molecular diversity and intrinsic drug resistance","volume":"12","author":"Meis","year":"2016","journal-title":"PLoS Pathog."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"S484","DOI":"10.1093\/infdis\/jix103","article-title":"Future research priorities in fungal resistance","volume":"216","author":"McCarthy","year":"2017","journal-title":"J. Infect. Dis."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"19292","DOI":"10.3390\/molecules191219292","article-title":"Natural cinnamic acids, synthetic derivatives and hybrids with antimicrobial activity","volume":"19","author":"Guzman","year":"2014","journal-title":"Molecules"},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"307","DOI":"10.4314\/tjpr.v13i2.22","article-title":"Prenylation of aromatic secondary metabolites: A new frontier for development of novel drugs","volume":"13","author":"Alhassan","year":"2014","journal-title":"Trop. J. Pharm. Res."},{"key":"ref_37","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_38","doi-asserted-by":"crossref","first-page":"74","DOI":"10.1016\/j.phymed.2017.06.005","article-title":"The interaction of auraptene and other oxyprenylated phenylpropanoids with glucose transporter type 4","volume":"32","author":"Genovese","year":"2017","journal-title":"Phytomedicine"},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"3426","DOI":"10.2174\/0929867322666150716114758","article-title":"A novel class of emerging anticancer compounds: Oxyprenylated secondary metabolites from plants and fungi","volume":"22","author":"Genovese","year":"2015","journal-title":"Curr. Med. Chem."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"198","DOI":"10.1016\/j.foodchem.2017.05.086","article-title":"Effective synthesis of magnetic porous molecularly imprinted polymers for efficient and selective extraction of cinnamic acid from apple juices","volume":"237","author":"Shi","year":"2017","journal-title":"Food Chem."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"17427","DOI":"10.1021\/acssuschemeng.0c05651","article-title":"Production of p-Coumaric Acid from Corn GVL-Lignin","volume":"8","author":"Timokhin","year":"2020","journal-title":"ACS Sustain. Chem. Eng."},{"key":"ref_42","first-page":"116","article-title":"Production of cinnamic and p-hydroxycinnamic acids in engineered microbes","volume":"3","author":"Gosset","year":"2015","journal-title":"Front. Bioeng. Biotechnol."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"578","DOI":"10.1016\/j.foodchem.2017.10.135","article-title":"A green deep eutectic solvent dispersive liquid-liquid micro-extraction (DES-DLLME) for the UHPLC-PDA determination of oxyprenylated phenylpropanoids in olive, soy, peanuts, corn, and sunflower oil","volume":"245","author":"Ferrone","year":"2018","journal-title":"Food Chem."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"e1900094","DOI":"10.1002\/cbdv.201900094","article-title":"Insight on propolis from mediterranean countries: Chemical composition, biological activities and application fields","volume":"16","author":"Lyoussi","year":"2019","journal-title":"Chem. Biodivers."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"1612","DOI":"10.1016\/j.ejmech.2007.11.001","article-title":"Effects of 3-(40-geranyloxy-30-methoxyphenyl)-2-trans propenoic acid and its ester derivatives on biofilm formation by two oral pathogens, Porphyromonas gingivalis and Streptococcus mutans","volume":"43","author":"Bodet","year":"2008","journal-title":"Eur. J. Med. Chem."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"1695","DOI":"10.1016\/j.sjbs.2018.08.013","article-title":"Composition and functional properties of propolis (bee glue): A review","volume":"26","author":"Anjum","year":"2019","journal-title":"Saudi J. Biol. Sci."},{"key":"ref_47","first-page":"206439","article-title":"Propolis: A complex natural product with a plethora of biological activities that can be explored for drug development","volume":"2015","author":"Baltazar","year":"2015","journal-title":"Evid. Based Complement Alternat. Med."},{"key":"ref_48","first-page":"515","article-title":"Propolis for the treatment of onychomycosis","volume":"63","author":"Veiga","year":"2018","journal-title":"Indian J. Dermatol."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"1311","DOI":"10.2217\/fmb-2017-0052","article-title":"Antibiofilm activity of propolis extract on Fusarium species from onychomycosis","volume":"12","author":"Galletti","year":"2017","journal-title":"Future Microbiol."},{"key":"ref_50","doi-asserted-by":"crossref","unstructured":"Oufensou, S., Scherm, B., Pani, G., Balmas, V., Fabbri, D., Dettori, M.A., Carta, P., Malbr\u00e1n, I., Migheli, Q., and Delogu, G. (2019). Honokiol, magnolol and its monoacetyl derivative show strong anti-fungal effect on Fusarium isolates of clinical relevance. PLoS ONE, 14.","DOI":"10.1371\/journal.pone.0221249"},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"917","DOI":"10.1128\/AAC.50.3.917-921.2006","article-title":"Head-to-head comparison of the activities of currently available antifungal agents against 3378 Spanish clinical isolates of yeasts and filamentous fungi","volume":"50","author":"Mellado","year":"2006","journal-title":"Antimicrob. Agents Chemother."},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"377","DOI":"10.1007\/s00253-019-10233-2","article-title":"The ability of farnesol to prevent adhesion and disrupt Fusarium keratoplasticum biofilm","volume":"104","author":"Kischkel","year":"2020","journal-title":"Appl. Microbiol. Biotechnol."},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"1937","DOI":"10.1093\/jac\/dks137","article-title":"In vitro antifungal susceptibility of filamentous fungi causing rare infections: Synergy testing of amphotericin B, posaconazole and anidulafungin in pairs","volume":"67","author":"Skiada","year":"2012","journal-title":"J. Antimicrob. Chemother."},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"453","DOI":"10.1007\/s00249-014-0983-8","article-title":"Recent progress in the study of the interactions of amphotericin B with cholesterol and ergosterol in lipid environments","volume":"43","year":"2014","journal-title":"Eur. Biophys. J."},{"key":"ref_55","doi-asserted-by":"crossref","unstructured":"Taj-Aldeen, S.J. (2017). Reduced multidrug susceptibility profile is a common feature of opportunistic Fusarium species: Fusarium multi-drug resistant pattern. J. Fungi, 3.","DOI":"10.3390\/jof3020018"},{"key":"ref_56","doi-asserted-by":"crossref","unstructured":"Zhou, K., Chen, D., Li, B., Zhang, B., Fang, M., and Zhou, L. (2017). Bioactivity and structure-activity relationship of cinnamic acid esters and their derivatives as potential antifungal agents for plant protection. PLoS ONE, 12.","DOI":"10.1371\/journal.pone.0176189"},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"68","DOI":"10.1002\/cmdc.201900544","article-title":"Structure-activity relationships of cinnamate ester analogues as potent antiprotozoal agents","volume":"15","author":"Bernal","year":"2020","journal-title":"Chem. Med. Chem."},{"key":"ref_58","doi-asserted-by":"crossref","unstructured":"Sidoryk, K., Jaromin, A., Filipczak, N., Cmoch, P., and Cybulsk, M. (2018). Synthesis and antioxidant activity of caffeic acid derivatives. Molecules, 23.","DOI":"10.3390\/molecules23092199"},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"3522","DOI":"10.1016\/j.tetlet.2017.07.089","article-title":"Ethyl acetate as a co-solvent and sacrificial ester in the aluminum triiodide promoted chemoselective demethylation of methyl vanillate","volume":"58","author":"Cuicui","year":"2017","journal-title":"Tetrahedron Lett."},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"2375","DOI":"10.1039\/c2gc35848d","article-title":"Laccase-catalyzed oxidative phenolic coupling of vanillidene derivatives","volume":"14","author":"Costantin","year":"2012","journal-title":"Green Chem."},{"key":"ref_61","doi-asserted-by":"crossref","first-page":"102991","DOI":"10.1016\/j.bioorg.2019.102991","article-title":"Structure-based design and synthesis of new 4-methylcoumarin-based lignans as pro-inflammatory cytokines (TNF-\u03b1, IL-6 and IL-1\u03b2) inhibitors","volume":"89","author":"Kumar","year":"2019","journal-title":"Bioorg. Chem."},{"key":"ref_62","doi-asserted-by":"crossref","first-page":"755","DOI":"10.1055\/s-1996-4289","article-title":"Bryophyte Constituents; 7: New synthesis of (+)-rosmarinic acid and related compounds","volume":"6","author":"Eicher","year":"1996","journal-title":"Synthesis"},{"key":"ref_63","doi-asserted-by":"crossref","first-page":"5266","DOI":"10.1039\/c2ob25124h","article-title":"First diastereoselective synthesis of methyl caffeoyl-and feruloyl-muco-quinates","volume":"10","author":"Jaiswal","year":"2012","journal-title":"Org. Biomol. Chem."},{"key":"ref_64","doi-asserted-by":"crossref","first-page":"5049","DOI":"10.1016\/j.bmcl.2005.07.088","article-title":"Synthesis of a novel prodrug of 3-(40-geranyloxy-30-methoxyphenyl)-2-trans-propenoic acid for colon delivery","volume":"15","author":"Curini","year":"2005","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_65","doi-asserted-by":"crossref","first-page":"88","DOI":"10.1021\/jo4023167","article-title":"Explorations of caffeic acid derivatives: Total syntheses of rufescenolide, yunnaneic acids C and D, and studies toward yunnaneic acids A and B","volume":"79","author":"Griffith","year":"2014","journal-title":"J. Org. Chem."},{"key":"ref_66","doi-asserted-by":"crossref","first-page":"1119","DOI":"10.1094\/MPMI.2002.15.11.1119","article-title":"A mitogen-activated protein kinase gene (MGV1) in Fusarium graminearum is required for female fertility, heterokaryon formation, and plant infection","volume":"15","author":"Hou","year":"2012","journal-title":"Mol. Plant Microbe Interact."},{"key":"ref_67","doi-asserted-by":"crossref","first-page":"39","DOI":"10.1016\/j.fgb.2011.11.002","article-title":"Heterochromatin influences the 866 secondary metabolite profile in the plant pathogen Fusarium graminearum","volume":"49","author":"Boedi","year":"2012","journal-title":"Fungal Genet. Biol."},{"key":"ref_68","doi-asserted-by":"crossref","first-page":"658","DOI":"10.1111\/j.1365-2230.2009.03698.x","article-title":"In vitro activity of fluconazole, itraconazole, voriconazole and terbinafine against fungi causing onychomycosis","volume":"35","author":"Bueno","year":"2010","journal-title":"Clin. Exp. Dermatol."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/26\/3\/658\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T05:16:08Z","timestamp":1760159768000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/26\/3\/658"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2021,1,27]]},"references-count":68,"journal-issue":{"issue":"3","published-online":{"date-parts":[[2021,2]]}},"alternative-id":["molecules26030658"],"URL":"https:\/\/doi.org\/10.3390\/molecules26030658","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2021,1,27]]}}}