{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,6,18]],"date-time":"2026-06-18T17:45:54Z","timestamp":1781804754399,"version":"3.54.5"},"reference-count":27,"publisher":"MDPI AG","issue":"5","license":[{"start":{"date-parts":[[2021,5,13]],"date-time":"2021-05-13T00:00:00Z","timestamp":1620864000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Plants"],"abstract":"<jats:p>Excessive melanin production causes serious dermatological conditions as well as minor aesthetic problems (i.e., freckles and solar lentigo). The downregulation of tyrosinase is a widespread approach for the treatment of such disorders, and plant extracts have often proven to be valuable sources of tyrosinase inhibitors. Citral (a mixture of neral and geranial) is an important fragrance ingredient that has shown anti-tyrosinase potential. It is highly concentrated in the essential oils (EOs) of Cymbopogon schoenanthus (L.) Spreng., Litsea cubeba (Lour.) Pers., Melissa officinalis L., and Verbena officinalis L. However, only L. cubeba EO has been investigated for use as a potential skin-whitening agent. This work evaluates the in vitro tyrosinase inhibitory activity of these EOs and studies, using bio-assay oriented fractionation, whether their differing chemical compositions influence the overall EO inhibitory activities via possible synergistic, additive, and\/or competitive interactions between EOs components. The inhibitory activity of C. schoenanthus EO and that of M. officinalis EOs, with negligible (+)-citronellal amounts, were in-line with their citral content. On the other hand, L. cubeba and V. officinalis EOs inhibited tyrosinase to considerably greater extents as they contained \u03b2-myrcene, which contributed to the overall EO activities. Similar observations were made for M. officinalis EO, which bears high (+)-citronellal content which increased citral activity.<\/jats:p>","DOI":"10.3390\/plants10050969","type":"journal-article","created":{"date-parts":[[2021,5,14]],"date-time":"2021-05-14T03:28:36Z","timestamp":1620962916000},"page":"969","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":35,"title":["Citral-Containing Essential Oils as Potential Tyrosinase Inhibitors: A Bio-Guided Fractionation Approach"],"prefix":"10.3390","volume":"10","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-1024-7088","authenticated-orcid":false,"given":"Francesca","family":"Capetti","sequence":"first","affiliation":[{"name":"Dipartimento di Scienza e Tecnologia del Farmaco, Universit\u00e0 degli Studi di Torino, Via Pietro Giuria 9, I-10125 Turin, Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7958-355X","authenticated-orcid":false,"given":"Massimo","family":"Tacchini","sequence":"additional","affiliation":[{"name":"Dipartimento di Scienze della vita e Biotecnologie, Universit\u00e0 degli Studi di Ferrara, Via L. Borsari 46, I-44121 Ferrara, Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Arianna","family":"Marengo","sequence":"additional","affiliation":[{"name":"Dipartimento di Scienza e Tecnologia del Farmaco, Universit\u00e0 degli Studi di Torino, Via Pietro Giuria 9, I-10125 Turin, Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3512-6124","authenticated-orcid":false,"given":"Cecilia","family":"Cagliero","sequence":"additional","affiliation":[{"name":"Dipartimento di Scienza e Tecnologia del Farmaco, Universit\u00e0 degli Studi di Torino, Via Pietro Giuria 9, I-10125 Turin, Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1782-7357","authenticated-orcid":false,"given":"Carlo","family":"Bicchi","sequence":"additional","affiliation":[{"name":"Dipartimento di Scienza e Tecnologia del Farmaco, Universit\u00e0 degli Studi di Torino, Via Pietro Giuria 9, I-10125 Turin, Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6819-2614","authenticated-orcid":false,"given":"Patrizia","family":"Rubiolo","sequence":"additional","affiliation":[{"name":"Dipartimento di Scienza e Tecnologia del Farmaco, Universit\u00e0 degli Studi di Torino, Via Pietro Giuria 9, I-10125 Turin, Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6848-1304","authenticated-orcid":false,"given":"Barbara","family":"Sgorbini","sequence":"additional","affiliation":[{"name":"Dipartimento di Scienza e Tecnologia del Farmaco, Universit\u00e0 degli Studi di Torino, Via Pietro Giuria 9, I-10125 Turin, Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2021,5,13]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"403","DOI":"10.1080\/14756366.2016.1256882","article-title":"Skin whitening agents: Medicinal chemistry perspective of tyrosinase inhibitors","volume":"32","author":"Pillaiyar","year":"2017","journal-title":"J. Enzym. Inhib. Med. Chem."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"943","DOI":"10.1111\/jdv.13595","article-title":"Overview of skin whitening agents with an insight into the illegal cosmetic market in Europe","volume":"30","author":"Desmedt","year":"2016","journal-title":"J. Eur. Acad. Dermatol. Venereol."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"85","DOI":"10.1016\/j.jpba.2013.11.024","article-title":"Characterization of suspected illegal skin whitening cosmetics","volume":"90","author":"Desmedt","year":"2014","journal-title":"J. Pharm. Biomed. Anal."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"4121","DOI":"10.1021\/jf990201q","article-title":"Flavonols from saffron flower: Tyrosinase inhibitory activity and inhibition mechanism","volume":"47","author":"Kubo","year":"1999","journal-title":"J. Agric. Food Chem."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"2","DOI":"10.1186\/1999-3110-54-10","article-title":"Chemical composition and tyrosinase inhibitory activity of Cinnamomum cassia essential oil","volume":"54","author":"Chang","year":"2013","journal-title":"Bot. Stud."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"6447","DOI":"10.1021\/jf301238q","article-title":"Action of tyrosinase on ortho-substituted phenols: Possible influence on browning and melanogenesis","volume":"60","year":"2012","journal-title":"J. Agric. Food Chem."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"5338","DOI":"10.1021\/jf980226+","article-title":"Tyrosinase Inhibitors from Cumin","volume":"46","author":"Kubo","year":"1998","journal-title":"J. Agric. Food Chem."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"2309","DOI":"10.1021\/jf051682i","article-title":"Tyrosinase inhibitory activity of citrus essential oils","volume":"54","author":"Matsuura","year":"2006","journal-title":"J. Agric. Food Chem."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"43","DOI":"10.1016\/j.ijat.2006.01.006","article-title":"In vitro bioactivities of essential oils used for acne control","volume":"16","author":"Lertsatitthanakorn","year":"2006","journal-title":"Int. J. Aromather."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"653","DOI":"10.1016\/j.biopha.2016.12.104","article-title":"Biological properties of citral and its potential protective effects against cytotoxicity caused by aspirin in the IEC-6 cells","volume":"87","author":"Bouzenna","year":"2017","journal-title":"Biomed. Pharmacother."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"342","DOI":"10.1007\/s12272-001-1162-0","article-title":"Inhibitory effect of citral on NO production by suppression of iNOS expression and NF-\u03baB activation in RAW264.7 cells","volume":"31","author":"Lee","year":"2008","journal-title":"Arch. Pharm. Res."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"31","DOI":"10.1016\/j.btre.2017.12.002","article-title":"Effect of the Lippia alba (Mill.) N.E. Brown essential oil and its main constituents, citral and limonene, on the tracheal smooth muscle of rats","volume":"17","author":"Carvalho","year":"2018","journal-title":"Biotechnol. Rep."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"155","DOI":"10.1016\/j.cbi.2018.11.006","article-title":"Tocolytic activity of the Lippia alba essential oil and its major constituents, citral and limonene, on the isolated uterus of rats","volume":"297","author":"Silva","year":"2019","journal-title":"Chem. Biol. Interact."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"792","DOI":"10.1016\/j.biopha.2018.09.073","article-title":"Vasorelaxant effect of the Lippia alba essential oil and its major constituent, citral, on the contractility of isolated rat aorta","volume":"108","author":"Silva","year":"2018","journal-title":"Biomed. Pharmacother."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"697","DOI":"10.1590\/1414-431x20154710","article-title":"Essential oil of Lippia alba and its main constituent citral block the excitability of rat sciatic nerves","volume":"48","author":"Sousa","year":"2015","journal-title":"Braz. J. Med. Biol. Res."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"112","DOI":"10.1080\/10412905.2012.755479","article-title":"Potential cosmetic application of essential oil extracted from Litsea cubeba fruits from China","volume":"25","author":"Huang","year":"2013","journal-title":"J. Essent. Oil Res."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"279","DOI":"10.1080\/14756366.2018.1545767","article-title":"A comprehensive review on tyrosinase inhibitors","volume":"34","author":"Zolghadri","year":"2019","journal-title":"J. Enzym. Inhib. Med. Chem."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"382","DOI":"10.1002\/ffj.1905","article-title":"Quantitative analysis of essential oils: A complex task","volume":"23","author":"Bicchi","year":"2008","journal-title":"Flavour Fragr. J."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"282","DOI":"10.1002\/ffj.1984","article-title":"Essential oils and volatiles: Sample preparation and analysis. A review","volume":"25","author":"Rubiolo","year":"2010","journal-title":"Flavour Fragr. J."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"515","DOI":"10.1016\/j.indcrop.2013.05.027","article-title":"The evaluation of the variability of morphological and chemical traits of the selected lemon balm (Melissa officinalis L.) genotypes","volume":"49","author":"Bocianowski","year":"2013","journal-title":"Ind. Crops Prod."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"4574","DOI":"10.1021\/jf990165v","article-title":"Tyrosinase inhibitory activity of the olive oil flavor compounds","volume":"47","author":"Kubo","year":"1999","journal-title":"J. Agric. Food Chem."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"255","DOI":"10.1002\/ffj.3315","article-title":"Chemical composition and the anti-melanogenic potential of different essential oils","volume":"31","author":"Fiocco","year":"2016","journal-title":"Flavour Fragr. J."},{"key":"ref_23","first-page":"97","article-title":"Inhibitory effect of lemon essential oil on mushroom tyrosinase activity in vitro","volume":"31","author":"Hu","year":"2015","journal-title":"Mod. Food Sci. Technol."},{"key":"ref_24","unstructured":"Council of Europe (2020). European Pharmacopoeia, Council of Europe. [10th ed.]."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"242","DOI":"10.1016\/j.fitote.2012.12.006","article-title":"Characterization of tyrosinase inhibitors in the twigs of Cudrania tricuspidata and their structure-activity relationship study","volume":"84","author":"Zheng","year":"2013","journal-title":"Fitoterapia"},{"key":"ref_26","first-page":"107","article-title":"Enzyme Assay Design for High-Throughput Screening","volume":"Volume 565","author":"Janzen","year":"2009","journal-title":"High Throughput Screening. Methods in Molecular Biology (Methods and Protocols)"},{"key":"ref_27","unstructured":"Markossian, S., Sittampalam, S., and Grossman, A. (2004). Basics of Enzymatic Assays for HTS, Assay Guidance Manual."}],"container-title":["Plants"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/2223-7747\/10\/5\/969\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T06:00:10Z","timestamp":1760162410000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/2223-7747\/10\/5\/969"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2021,5,13]]},"references-count":27,"journal-issue":{"issue":"5","published-online":{"date-parts":[[2021,5]]}},"alternative-id":["plants10050969"],"URL":"https:\/\/doi.org\/10.3390\/plants10050969","relation":{},"ISSN":["2223-7747"],"issn-type":[{"value":"2223-7747","type":"electronic"}],"subject":[],"published":{"date-parts":[[2021,5,13]]}}}