{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,1,30]],"date-time":"2026-01-30T04:31:56Z","timestamp":1769747516782,"version":"3.49.0"},"reference-count":44,"publisher":"MDPI AG","issue":"10","license":[{"start":{"date-parts":[[2017,9,22]],"date-time":"2017-09-22T00:00:00Z","timestamp":1506038400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>The composition of the essential oil (EO) of Thapsia villosa (Apiaceae), isolated by hydrodistillation from the plant\u2019s aerial parts, was analysed by GC and GC-MS. Antifungal activity of the EO and its main components, limonene (57.5%) and methyleugenol (35.9%), were evaluated against clinically relevant yeasts (Candida spp., Cryptococcus neoformans and Malassezia furfur) and moulds (Aspergillus spp. and dermatophytes). Minimum inhibitory concentrations (MICs) were measured according to the broth macrodilution protocols by Clinical and Laboratory Standards Institute (CLSI). The EO, limonene and methyleugenol displayed low MIC and MFC (minimum fungicidal concentration) values against Candida spp., Cryptococcus neoformans, dermatophytes, and Aspergillus spp. Regarding Candida species, an inhibition of yeast\u2013mycelium transition was demonstrated at sub-inhibitory concentrations of the EO (MIC\/128; 0.01 \u03bcL\/mL) and their major compounds in Candida albicans. Fluconazole does not show this activity, and the combination with low concentrations of EO could associate a supplementary target for the antifungal activity. The association of fluconazole with T. villosa oil does not show antagonism, but the combination limonene\/fluconazole displays synergism. The fungistatic and fungicidal activities revealed by T. villosa EO and its main compounds, associated with their low haemolytic activity, confirm their potential antimicrobial interest against fungal species often associated with human mycoses.<\/jats:p>","DOI":"10.3390\/molecules22101595","type":"journal-article","created":{"date-parts":[[2017,9,22]],"date-time":"2017-09-22T11:03:15Z","timestamp":1506078195000},"page":"1595","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":55,"title":["Antifungal Activity of Thapsia villosa Essential Oil against Candida, Cryptococcus, Malassezia, Aspergillus and Dermatophyte Species"],"prefix":"10.3390","volume":"22","author":[{"given":"Eug\u00e9nia","family":"Pinto","sequence":"first","affiliation":[{"name":"Laboratory of Microbiology, Biological Sciences Department, Faculty of Pharmacy of University of Porto, Rua Jorge Viterbo Ferreira n\u00b0 228, 4050-313 Porto, Portugal"},{"name":"Interdisciplinary Centre of Marine and Environmental Research (CIIMAR\/CIMAR), University of Porto, Terminal de Cruzeiros do Porto de Leix\u00f5es Av. General Norton de Matos s\/n, 4450-208 Matosinhos, Portugal"}]},{"given":"Maria-Jos\u00e9","family":"Gon\u00e7alves","sequence":"additional","affiliation":[{"name":"CNC.IBILI, Faculty of Pharmacy, University of Coimbra, Azinhaga de S. Comba, 3000-354 Coimbra, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5937-1127","authenticated-orcid":false,"given":"Carlos","family":"Cavaleiro","sequence":"additional","affiliation":[{"name":"CNC.IBILI, Faculty of Pharmacy, University of Coimbra, Azinhaga de S. Comba, 3000-354 Coimbra, Portugal"}]},{"given":"L\u00edgia","family":"Salgueiro","sequence":"additional","affiliation":[{"name":"CNC.IBILI, Faculty of Pharmacy, University of Coimbra, Azinhaga de S. Comba, 3000-354 Coimbra, Portugal"}]}],"member":"1968","published-online":{"date-parts":[[2017,9,22]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","unstructured":"Baser, C.K.H., and Buchbauer, G. (2010). Sources of essential oils. Handbook of Essential Oils: Science, Technology, and Applications, CRC Press, Taylor & Francis Group.","DOI":"10.1201\/9781420063165"},{"key":"ref_2","first-page":"64","article-title":"The detailed analysis of essential oil leads to the understanding of their properties","volume":"25","author":"Buchbauer","year":"2000","journal-title":"Perfum. Flavorist"},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"446","DOI":"10.1016\/j.fct.2007.09.106","article-title":"Biological effects of essential oils\u2014A review","volume":"46","author":"Bakkali","year":"2008","journal-title":"Food Chem. Toxicol."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"5","DOI":"10.1111\/j.1469-0691.2008.01978.x","article-title":"Changing epidemiology of systemic fungal infections","volume":"14","author":"Richardson","year":"2008","journal-title":"Clin. Microbiol. Infect."},{"key":"ref_5","doi-asserted-by":"crossref","unstructured":"Richardson, M.D., and Warnock, D.W. (2012). Fungal Infection: Diagnosis and Management, Wiley-Blackwell. [4th ed.].","DOI":"10.1002\/9781118321492"},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"195","DOI":"10.1016\/j.tim.2010.02.004","article-title":"Therapy for fungal diseases: Opportunities and priorities","volume":"18","author":"Denning","year":"2010","journal-title":"Trends Microbiol."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1016\/j.amjmed.2011.11.001","article-title":"Antifungal drug resistance: Mechanism, epidemiology and consequences for treatment","volume":"125","author":"Pfaller","year":"2012","journal-title":"Am. J. Med."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"765","DOI":"10.1016\/j.foodchem.2009.11.008","article-title":"Phytochemical composition of the essential oils from three Apiaceae species and their antibacterial effects on food-borne pathogens","volume":"120","author":"Oroojalian","year":"2010","journal-title":"Food Chem."},{"key":"ref_9","first-page":"307","article-title":"Essential oil from the underground parts of Laserpitium zernyi: Potential source of alfa-bisabolol and its antimicrobial activity","volume":"5","author":"Couladis","year":"2010","journal-title":"Nat. Prod. Commun."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"593","DOI":"10.1016\/j.jep.2010.05.054","article-title":"Essential oils of Distichoselinum tenuifolium: Chemical composition, cytotoxicity, antifungal and anti-inflammatory properties","volume":"130","author":"Tavares","year":"2010","journal-title":"J. Etnopharmacol."},{"key":"ref_11","first-page":"263","article-title":"Composition and antimicrobial activity of Seseli montanum subsp. tommasinii essential oil","volume":"6","author":"Glamoclija","year":"2011","journal-title":"Nat. Prod. Commun."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"361","DOI":"10.1016\/j.indcrop.2014.11.014","article-title":"Daucus carota subsp. gummifer essential oil as a natural source of antifungal and anti-inflammatory drugs","volume":"65","author":"Valente","year":"2015","journal-title":"Ind. Crops Prod."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"2165","DOI":"10.5897\/JMPR11.1597","article-title":"Botanical identification and ethnomedicinal uses of some underground parts of medicinal plants collected and traded in Marrakech region","volume":"7","author":"Abderrahim","year":"2013","journal-title":"J. Med. Plants Res."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"1042","DOI":"10.1080\/14786419.2015.1104676","article-title":"Chemical composition of the essential oil from Thapsia garganica (Apiaceae) grown wild in Sicily and its antimicrobial activity","volume":"30","author":"Casiglia","year":"2016","journal-title":"Nat. Prod. Res."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"4696","DOI":"10.1021\/jm010985a","article-title":"Design, synthesis and pharmacological evaluation of thapsigargin analogues for targeting apoptosis to prostatic cancer cells","volume":"44","author":"Jakobsen","year":"2001","journal-title":"J. Med. Chem."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"166","DOI":"10.1016\/j.indcrop.2011.06.030","article-title":"Composition and biological activity of the essential oil from Thapsia minor, a new source of geranyl acetate","volume":"35","author":"Cruz","year":"2012","journal-title":"Ind. Crops Prod."},{"key":"ref_17","unstructured":"Castroviejo, S., La\u00ednz, M., L\u00f3pez Gonz\u00e1lez, G., Montserrat, P., Mu\u00f1oz Garmendia, F., Paiva, J., and Villar, L. (2003). Araliaceae-Umbelliferae. Flora Ib\u00e9rica, Plantas Vasculares de la Pen\u00ednsula Ib\u00e9rica, e Islas Baleares, Real Jard\u00edn Bot\u00e1nico, CSIC."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"123","DOI":"10.1080\/10412905.1996.9700578","article-title":"Composition of the essential oils of fruits from polyploid types of Thapsia villosa: Chemotaxonomic evaluation","volume":"8","author":"Avato","year":"1996","journal-title":"J. Essent. Oil Res."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"609","DOI":"10.1016\/0031-9422(96)00300-7","article-title":"Essential oils from fruits of three types of Thapsia villosa","volume":"43","author":"Avato","year":"1996","journal-title":"Phytochemistry"},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"411","DOI":"10.1021\/np50093a014","article-title":"Localization of the acyl groups in proazulene guaianolides from Thapsia transtagana and Thapsia garganica","volume":"56","author":"Avato","year":"1993","journal-title":"J. Nat. Prod."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"35","DOI":"10.1016\/j.micpath.2009.10.001","article-title":"Evolution of ergosterol biosynthesis inhibitors as fungicidal against Candida","volume":"48","author":"Ahmad","year":"2010","journal-title":"Microb. Pathog."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"1178","DOI":"10.1099\/jmm.0.020693-0","article-title":"Synergy of eugenol and methyleugenol with fluconazole against clinical Candida isolates","volume":"59","author":"Ahmad","year":"2010","journal-title":"J. Med. Microbiol."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1673\/031.012.5601","article-title":"Methyl eugenol: Its occurrence, distribution, and role in nature, especially in relation to insect behavior and pollination","volume":"12","author":"Tan","year":"2012","journal-title":"J. Insect. Sci."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"17926","DOI":"10.3390\/molecules191117926","article-title":"Antifungal activity and computational study of constituents from Piper divaricatum essential oil against Fusarium infection in black pepper","volume":"19","author":"Silva","year":"2014","journal-title":"Molecules"},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"457","DOI":"10.4103\/0250-474X.119834","article-title":"Chemical composition, in vitro antimicrobial and antioxidant activities of the essential oils of Ocimum Gratissimum, O. Sanctum and their major constituents","volume":"8","author":"Joshi","year":"2013","journal-title":"Indian J. Pharm. Sci."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"1454","DOI":"10.1099\/jmm.0.010538-0","article-title":"Antifungal activity of the clove essential oil from Syzygium aromaticum on Candida, Aspergillus and dermatophyte species","volume":"58","author":"Pinto","year":"2009","journal-title":"J. Med. Microbiol."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"243","DOI":"10.4489\/MYCO.2009.37.3.243","article-title":"In vitro antifungal activity of limonene against Trichophyton rubrum","volume":"37","author":"Chee","year":"2009","journal-title":"Mycobiology"},{"key":"ref_28","first-page":"248","article-title":"Antibacterial activity of selected compounds of essential oils indigenous plants","volume":"5","author":"Vimal","year":"2013","journal-title":"J. Chem. Pharm. Res."},{"key":"ref_29","doi-asserted-by":"crossref","unstructured":"Espina, L., Gelaw, T.K., Lamo-Castellv\u00ed, S., Pag\u00e1n, R., and Garc\u00eda-Gonzalo, D. (2013). Mechanism of Bacterial inactivation by (+)-limonene and its potential use in food preservation combined processes. PLoS ONE, 8.","DOI":"10.1371\/journal.pone.0056769"},{"key":"ref_30","first-page":"259","article-title":"D-Limonene: Safety and clinical applications","volume":"12","author":"Sun","year":"2007","journal-title":"Altern. Med. Rev."},{"key":"ref_31","doi-asserted-by":"crossref","unstructured":"Berger, R.G. (2007). Bioactivity of essential oils and their components. Flavour and Fragrances\u2014Chemistry, Bioprocessing and Sustainability, Springer.","DOI":"10.1007\/978-3-540-49339-6"},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"3312","DOI":"10.1128\/AAC.00628-06","article-title":"Inhibition of filamentation can be used to treat disseminated candidiasis","volume":"50","author":"Saville","year":"2006","journal-title":"Antimicrob. Agents Chemother."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"1359","DOI":"10.1007\/s10096-011-1450-4","article-title":"Antifungal activity of phenolic-rich Lavandula multifida L. essential oil","volume":"31","author":"Zuzarte","year":"2012","journal-title":"Eur. J. Clin. Microbiol. Infect. Dis."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"241","DOI":"10.1007\/s11418-014-0884-2","article-title":"Antifungal activity of the essential oil of Angelica major against Candida, Cryptococcus, Aspergillus and dermatophyte species","volume":"69","author":"Cavaleiro","year":"2015","journal-title":"J. Nat. Med."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"143","DOI":"10.1007\/s11046-016-0081-9","article-title":"Natural products: An alternative to conventional therapy for dermatophytosis?","volume":"182","author":"Lopes","year":"2017","journal-title":"Mycopathologia"},{"key":"ref_36","first-page":"315","article-title":"Chemical composition and antifungal activity of plant essential oils against Malassezia furfur","volume":"38","author":"Lee","year":"2010","journal-title":"Korean J. Microbiol. Biotechnol."},{"key":"ref_37","unstructured":"Council of Europe (1997). European Pharmacopoeia, Council of Europe. [3rd ed.]."},{"key":"ref_38","unstructured":"Adams, R.P. (2004). Identification of Essential Oil Components by Gas Chromatogra-phy\/Mass Spectroscopy, Allured Publishing Corporation."},{"key":"ref_39","unstructured":"Wiley (2006). Wiley Registry of Mass Spectral Data Information, Wiley."},{"key":"ref_40","unstructured":"Joulain, D., and Konig, W.A. (1998). The Atlas of Spectral Data of Sesquiterpene Hydrocarbons, E.B. Verlag."},{"key":"ref_41","unstructured":"Clinical and Laboratory Standards Institute (2008). Reference Method for Broth Dilution Antifungal Susceptibility Testing of Yeasts, CLSI. Approved Standard-Third Edition M27-A3 and Third Informational Supplement M27-S3."},{"key":"ref_42","unstructured":"Clinical and Laboratory Standards Institute (2008). Reference Method for Broth Dilution Antifungal Susceptibility Testing of Conidium-Forming Filamentous Fungi, CLSI. Approved Standard-Second edition M38-A2."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"163","DOI":"10.1128\/CMR.18.1.163-194.2005","article-title":"Combination treatment of invasive fungal infections","volume":"18","author":"Mukherjee","year":"2005","journal-title":"Clin. Microbiol. Rev."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"76","DOI":"10.1111\/j.1439-0507.1986.tb03753.x","article-title":"Culture Media for the study of the effects of azole derivatives on germ tube formation and hyphal growth of Candida albicans","volume":"29","author":"Marichal","year":"1986","journal-title":"Mykosen"}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/22\/10\/1595\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T18:45:39Z","timestamp":1760208339000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/22\/10\/1595"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2017,9,22]]},"references-count":44,"journal-issue":{"issue":"10","published-online":{"date-parts":[[2017,10]]}},"alternative-id":["molecules22101595"],"URL":"https:\/\/doi.org\/10.3390\/molecules22101595","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2017,9,22]]}}}