{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,22]],"date-time":"2026-10-22T17:09:10Z","timestamp":1792688950082,"version":"4.5.0"},"reference-count":45,"publisher":"MDPI AG","issue":"7","license":[{"start":{"date-parts":[[2017,7,4]],"date-time":"2017-07-04T00:00:00Z","timestamp":1499126400000},"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>This work describes the isolation and structural elucidation of compounds from the leaves of Myrcia tomentosa (Aubl.) DC. (goiaba-brava) and evaluates the antimicrobial activity of the crude extract, fractions and isolated compounds against bacteria and fungi. Column chromatography was used to fractionate and purify the extract of the M. tomentosa leaves and the chemical structures of the compounds were determined using spectroscopic techniques. The antibacterial and antifungal activities were assessed using the broth microdilution method. The phytochemical investigation isolated 11 compounds: \u03b1-bisabolol, \u03b1-bisabolol oxide B, \u03b1-cadinol, \u03b2-sitosterol, n-pentacosane, n-tetracosane, quercetin, kaempferol, avicularin, juglanin and guaijaverin. The crude ethanolic extract and its fractions were tested against 15 bacteria and 9 yeasts. The crude extract inhibited the in vitro growth of yeasts at concentration of 4 to 32 \u03bcg\/mL. The hexane, dichloromethane, ethyl acetate and aqueous fractions inhibited Candida sp. at concentrations of 4 to 256 \u03bcg\/mL, whereas the Cryptococcus sp. isolates were inhibited only by the hexane and dichloromethane fractions in minimal inhibitory concentrations (MICs) at 16 to 64 \u03bcg\/mL. The flavonoid quercetin-3-O-\u03b1-arabinofuranose (avicularin) was the most active compound, inhibiting Candida species in concentrations of 2 to 32 \u03bcg\/mL. The MIC values suggest potential activity of this plant species against yeast.<\/jats:p>","DOI":"10.3390\/molecules22071100","type":"journal-article","created":{"date-parts":[[2017,7,4]],"date-time":"2017-07-04T10:31:57Z","timestamp":1499164317000},"page":"1100","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":42,"title":["Phytochemical Analysis and Antimicrobial Activity of Myrcia tomentosa (Aubl.) DC. Leaves"],"prefix":"10.3390","volume":"22","author":[{"given":"Fabyola","family":"Da Silva Sa","sequence":"first","affiliation":[{"name":"Institute of Tropical Pathology and Public Health, Federal University of Goias, Goi\u00e2nia 74605-050, Brazil"},{"name":"Faculty of Pharmacy, Federal University of Goias, Goi\u00e2nia 74605-170, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Joelma","family":"De Paula","sequence":"additional","affiliation":[{"name":"Unit of Exact and Technologic Sciences, Goias State University, An\u00e1polis 75132-400, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Pierre","family":"Dos Santos","sequence":"additional","affiliation":[{"name":"Faculty of Pharmacy, Federal University of Goias, Goi\u00e2nia 74605-170, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Leandra","family":"De Almeida Ribeiro Oliveira","sequence":"additional","affiliation":[{"name":"Faculty of Pharmacy, Federal University of Goias, Goi\u00e2nia 74605-170, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Gerlon","family":"De Almeida Ribeiro Oliveira","sequence":"additional","affiliation":[{"name":"Chemistry Institute, Federal University of Goi\u00e1s, Goi\u00e2nia 74690-900, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Luciano","family":"Liao","sequence":"additional","affiliation":[{"name":"Chemistry Institute, Federal University of Goi\u00e1s, Goi\u00e2nia 74690-900, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jose","family":"De Paula","sequence":"additional","affiliation":[{"name":"Faculty of Pharmacy, Federal University of Goias, Goi\u00e2nia 74605-170, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Maria","family":"Do Rosario Rodrigues Silva","sequence":"additional","affiliation":[{"name":"Institute of Tropical Pathology and Public Health, Federal University of Goias, Goi\u00e2nia 74605-050, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2017,7,4]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"311","DOI":"10.1021\/np200906s","article-title":"Natural products as sources of new drugs over the 30 Years from 1981 to 2010","volume":"75","author":"Newman","year":"2012","journal-title":"J. Nat. Prod."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"439","DOI":"10.1021\/np3006875","article-title":"Development of a natural products data base from the biodiversity of Brazil","volume":"76","author":"Valli","year":"2013","journal-title":"J. Nat. Prod."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"299","DOI":"10.1007\/s11101-014-9367-z","article-title":"The pharmaceutical industry and natural products: Historical status and new trends","volume":"14","author":"David","year":"2015","journal-title":"Phytochem. Rev."},{"key":"ref_4","first-page":"1","article-title":"Diversidade e import\u00e2ncia econ\u00f4mica das Myrtaceae do Cerrado, Parque Estadual do Mirador, Maranh\u00e3o","volume":"6","year":"2010","journal-title":"Sci. Plena"},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"509","DOI":"10.1590\/S0100-84042006000400002","article-title":"Poliniza\u00e7\u00e3o e dispers\u00e3o de sementes em Myrtaceae do Brasil","volume":"29","author":"Gressler","year":"2006","journal-title":"Braz. J. Bot."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"23881","DOI":"10.3390\/ijms161023881","article-title":"Constituents and pharmacological activities of Myrcia (Myrtaceae): A review of an aromatic and medicinal group of plants","volume":"16","author":"Cascaes","year":"2015","journal-title":"Int. J. Mol. Sci."},{"key":"ref_7","unstructured":"Judd, W.S., Campbell, C.S., Kellog, E.A., Stevens, P.F., and Donoghe, M.J. (2009). Sistem\u00e1tica Vegetal: Um Enfoque Filogen\u00e9tico, Artmed. [3rd ed.]."},{"key":"ref_8","first-page":"55","article-title":"Myrtaceae, in the botany of the Guayana Highland, VIII. Mem","volume":"18","author":"McVaugh","year":"1969","journal-title":"N. Y. Bot. Gard."},{"key":"ref_9","first-page":"35","article-title":"Levantamento de floresta de galeria no ribeir\u00e3o DoisIrm\u00e3os na APA de Cafuringa, DF, Brasil","volume":"22","author":"Paula","year":"2009","journal-title":"Biotemas"},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"181","DOI":"10.1007\/s11258-010-9813-y","article-title":"Defense syndromes against herbivory in a cerrado plant community","volume":"212","author":"Silva","year":"2011","journal-title":"Plant Ecol."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"351","DOI":"10.1021\/tx0501684","article-title":"Inhibition of thyroid peroxidase by Myrcia uniflora flavonoids","volume":"19","author":"Ferreira","year":"2006","journal-title":"Chem. Res. Toxicol."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"1569","DOI":"10.1055\/s-0030-1270956","article-title":"The 2\u2032,4\u2032,6\u2032-trihydroxyacetophenone isolated from Myrcia multiflora has antiobesity and mixed hypolipidemic effects with the reduction of lipid intestinal absorption","volume":"77","author":"Ferreira","year":"2011","journal-title":"Planta Med."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1155\/2014\/543606","article-title":"Myrcia bella leaf extract presents hypoglycemic activity via PI3k\/Akt insulin signaling pathway","volume":"2014","author":"Vareda","year":"2014","journal-title":"Evid. Based Complement. Altern. Med."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"1249","DOI":"10.1016\/j.phytochem.2006.04.025","article-title":"Biochemical activities of Iranian Mentha piperita L. and Myrtus communis L. essential oils","volume":"67","author":"Yadegarinia","year":"2006","journal-title":"Phytochemistry"},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"181","DOI":"10.1590\/S0102-695X2011005000205","article-title":"Phytochemical screening, antinociceptive and anti-inflammatory effects of the essential oil of Myrcia pubiflora in mice","volume":"22","author":"Andrade","year":"2012","journal-title":"Rev. Bras. Farmacogn."},{"key":"ref_16","doi-asserted-by":"crossref","unstructured":"Xu, L., Gao, J., Wang, Y., Yu, W., Zhao, X., Yang, X., Zhong, Z., and Qian, Z.-M. (2011). Myrica rubra extracts protect the liver from CCl4-induced damage. Evidence-Based Complement. Altern. Med., 1\u20138.","DOI":"10.1093\/ecam\/nep196"},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"734","DOI":"10.1590\/S0102-695X2010005000021","article-title":"In vitro antifungal activity and cytotoxic effect of essential oils and extracts of medicinal and aromatic plants against Candida krusei and Aspergillus fumigatus","volume":"20","author":"Tangarife","year":"2010","journal-title":"Rev. Bras. Farmacogn."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"780","DOI":"10.1021\/np50058a023","article-title":"Sesquiterpenes from Vanillosmopsis arborea","volume":"51","author":"Matos","year":"1988","journal-title":"J. Nat. Prod."},{"key":"ref_19","unstructured":"(2008). NIST Standard Reference Database 1A NIST\/EPA\/NIH Mass Spectral Library (NIST 08) and NIST Mass Spectral Search Program, National Institute of Standards and Technology. Version 2.0f."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"239","DOI":"10.3329\/icpj.v1i9.11613","article-title":"Isolation of stigmasterol and \u03b2-sitosterol from the dichloromethane extract of Rubus suavissimus","volume":"1","author":"Chaturvedula","year":"2012","journal-title":"Int. Curr. Pharm. J."},{"key":"ref_21","first-page":"95","article-title":"Fitoconstituintes qu\u00edmicos isolados de Jatropha elliptica. Atribui\u00e7\u00e3o dos deslocamentos qu\u00edmicos dos \u00e1tomos de carbono e hidrog\u00eanio dos diterpenos Jatrofolonas A e B","volume":"16","author":"Goulart","year":"1993","journal-title":"Quim. Nova"},{"key":"ref_22","first-page":"234","article-title":"Phytochemical constituents of Bistorta manshuriensis","volume":"15","author":"Chang","year":"2009","journal-title":"Nat. Prod. Sci."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"1231","DOI":"10.1080\/14786410600905816","article-title":"A new kaempferol diglycoside from Datura suaveolens Humb. & Bonpl. ex. Willd","volume":"20","author":"Begum","year":"2006","journal-title":"Nat. Prod. Res."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"2241","DOI":"10.1590\/S0100-40422012001100028","article-title":"Estudo fitoqu\u00edmico e avalia\u00e7\u00e3o da atividade anti-inflamat\u00f3ria de Aeschynomene fluminensis vell. (Fabaceae)","volume":"35","author":"Ignoato","year":"2012","journal-title":"Quim. Nova"},{"key":"ref_25","first-page":"151","article-title":"Chemical constituents of Geranium eristemon","volume":"15","author":"Chang","year":"2009","journal-title":"Nat. Prod. Sci."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"487","DOI":"10.1111\/j.1365-2672.2006.02912.x","article-title":"Guaijaverin\u2014A plant flavonoid as potential antiplaque agent against Streptococcus mutans","volume":"101","author":"Prabu","year":"2006","journal-title":"J. Appl. Microbiol."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"1027","DOI":"10.1590\/S0074-02762002000700017","article-title":"Screening of some plants used in the Brazilian folk medicine for the treatment of infectious diseases","volume":"97","author":"Holetz","year":"2002","journal-title":"Mem. Inst. Oswaldo Cruz"},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"90","DOI":"10.1590\/S0102-695X2008000100017","article-title":"Atividade antibacteriana de plantas \u00fateis e constituintes qu\u00edmicos da raiz de Copernicia prunifera","volume":"18","author":"Ayres","year":"2008","journal-title":"Rev. Bras. Farmacogn."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"706","DOI":"10.1590\/S0102-695X2010005000017","article-title":"Antimicrobial activity of Pterogyne nitens Tul., Fabaceae, against opportunistic fungi","volume":"20","author":"Regasini","year":"2010","journal-title":"Rev. Bras. Farmacogn."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"695","DOI":"10.1007\/s11101-013-9331-3","article-title":"The evolution of foliar terpene diversity in Myrtaceae","volume":"13","author":"Padovan","year":"2014","journal-title":"Phytochem. Rev."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"1406","DOI":"10.1016\/j.phytochem.2011.04.013","article-title":"Composition and antifungal activity of the essential oil from the rhizome and roots of Ferula hermonis","volume":"72","author":"Vila","year":"2011","journal-title":"Phytochemistry"},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"38","DOI":"10.1021\/np960513c","article-title":"Bioactive compounds from Taiwania cryptomerioides","volume":"60","author":"He","year":"1997","journal-title":"J. Nat. Prod."},{"key":"ref_33","first-page":"273","article-title":"Composition, in-vitro anticancer, and antimicrobial activities of the leaf essential oil of Machilus mushaensis from Taiwan","volume":"8","author":"Su","year":"2013","journal-title":"Nat. Prod. Commun."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1007\/s11746-009-1483-3","article-title":"A review of the application and pharmacological properties of \u03b1-bisabolol and \u03b1-bisabolol-rich oils","volume":"87","author":"Kamatou","year":"2010","journal-title":"J. Am. Oil Chem. Soc."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"212","DOI":"10.4103\/0973-1296.66939","article-title":"Phytochemical investigation and antimicrobial activity of Psidium guajava L. leaves","volume":"6","author":"Metwally","year":"2010","journal-title":"Pharmacogn. Mag."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"1479","DOI":"10.1055\/s-0030-1250027","article-title":"Potential of Cameroonian plants and derived products against microbial infections: A review","volume":"76","author":"Kuete","year":"2010","journal-title":"Planta Med."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"648","DOI":"10.1016\/j.indcrop.2015.05.067","article-title":"Activity of phenolic compounds from plant origin against Candida species","volume":"74","author":"Martins","year":"2015","journal-title":"Ind. Crops Prod."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"695","DOI":"10.1016\/j.bbamem.2014.11.019","article-title":"Fungicidal effect of isoquercitrin via inducing membrane disturbance","volume":"1848","author":"Yun","year":"2015","journal-title":"Biochim. Biophys. Acta"},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"17903","DOI":"10.3390\/molecules201017903","article-title":"Activity of polyphenolic compounds against Candida glabrata","volume":"20","author":"Torres","year":"2015","journal-title":"Molecules"},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"23","DOI":"10.1590\/S0102-695X2010000100006","article-title":"Estudo fitoqu\u00edmico e avalia\u00e7\u00e3o da toxicidade frente a Artemia salina e da atividade antimicrobiana de Calycorectes psidiiflorus (O. Berg) Sobral, Myrtaceae","volume":"20","author":"Domingues","year":"2010","journal-title":"Rev. Bras. Farmacogn."},{"key":"ref_41","first-page":"1","article-title":"Phytochemical analysis and antimicrobial, antinociceptive, and anti-inflammatory activities of two chemotypes of Pimenta pseudocaryophyllus (Myrtaceae). Evidence-Based Complement","volume":"2012","author":"Paula","year":"2012","journal-title":"Altern. Med."},{"key":"ref_42","first-page":"203","article-title":"Activity of crude extracts from Brazilian Cerrado plants against clinically relevant Candida species. BMC Complement","volume":"16","author":"Correia","year":"2016","journal-title":"Altern. Med."},{"key":"ref_43","unstructured":"Clinical and Laboratory Standards Institute (CLSI) (2008). Reference Method for Broth Dilution Antifungal Susceptibility Testing of Yeasts, CLSI. [3rd ed.]."},{"key":"ref_44","unstructured":"Clinical and Laboratory Standards Institute (CLSI) (2009). Methods for Dilution Antimicrobial Susceptibility Test for Bacteria that Grow Aerobically, CLSI. [8th ed.]."},{"key":"ref_45","unstructured":"Clinical and Laboratory Standards Institute (CLSI) (2012). Reference Method for Broth Dilution Antifungal Susceptibility Testing of Yeasts, CLSI. Fourth Information Supplement."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/22\/7\/1100\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T18:41:28Z","timestamp":1760208088000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/22\/7\/1100"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2017,7,4]]},"references-count":45,"journal-issue":{"issue":"7","published-online":{"date-parts":[[2017,7]]}},"alternative-id":["molecules22071100"],"URL":"https:\/\/doi.org\/10.3390\/molecules22071100","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2017,7,4]]}}}