{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,31]],"date-time":"2026-07-31T04:17:03Z","timestamp":1785471423572,"version":"3.56.0"},"reference-count":38,"publisher":"MDPI AG","issue":"22","license":[{"start":{"date-parts":[[2023,11,14]],"date-time":"2023-11-14T00:00:00Z","timestamp":1699920000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"PAPQ (Programa de Apoio \u00e0 Publica\u00e7\u00e3o Qualificada)"},{"name":"Propesp (PAPQ, Propesp, UFPa)"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Aniba canelilla (Kunth) Mez essential oil has many biological activities due to its main compound 1-nitro-2-phenylethane (1N2F), followed by methyleugenol, a carcinogenic agent. This study analyzed the influence of seasonality on yields, antioxidant capacity, and 1N2F content of A. canelilla leaf and twig essential oils. Essential oils (EOs) were extracted with hydrodistillation and analyzed with gas chromatography coupled to mass spectrometry and a flame ionization detector. Antioxidant capacity was measured using the free radical scavenging method (DPPH). Chemometric analyses were carried out to verify the influence of climatic factors on the production and composition of EOs. 1-Nitro-2-phenylethane was the major constituent in A. canelilla EOs throughout the seasonal period (68.0\u201389.9%); methyleugenol was not detected. Essential oil yields and the 1N2F average did not show a statistically significant difference between the dry and rainy seasons in leaves and twigs. Moderate and significant correlations between major compounds and climate factor were observed. The twig oils (36.0 \u00b1 5.9%) a showed greater antioxidant capacity than the leaf oils (20.4 \u00b1 5.0%). The PCA and HCA analyses showed no statistical differences between the oil samples from the dry and rainy seasons. The absence of methyleugenolin in all months of study, described for the first time, makes this specimen a reliable source of 1N2F.<\/jats:p>","DOI":"10.3390\/molecules28227573","type":"journal-article","created":{"date-parts":[[2023,11,14]],"date-time":"2023-11-14T09:46:13Z","timestamp":1699955173000},"page":"7573","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":7,"title":["Seasonal Variation in Essential Oil Composition and Antioxidant Capacity of Aniba canelilla (Lauraceae): A Reliable Source of 1-Nitro-2-phenylethane"],"prefix":"10.3390","volume":"28","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-2682-2964","authenticated-orcid":false,"given":"Ellen de Nazar\u00e9 S. da","family":"Cruz","sequence":"first","affiliation":[{"name":"Programa Institucional de Bolsas de Inicia\u00e7\u00e3o Cient\u00edfica, Universidade Federal do Par\u00e1, Belem 66075-900, Brazil"},{"name":"Laborat\u00f3rio de Qu\u00edmica dos Produtos Naturais, Centro de Ci\u00eancias Biol\u00f3gicas e da Sa\u00fade, Universidade do Estado do Par\u00e1, Belem 66087-662, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Luana de Sousa P.","family":"Barros","sequence":"additional","affiliation":[{"name":"Laborat\u00f3rio de Qu\u00edmica dos Produtos Naturais, Centro de Ci\u00eancias Biol\u00f3gicas e da Sa\u00fade, Universidade do Estado do Par\u00e1, Belem 66087-662, Brazil"},{"name":"Programa de P\u00f3s-Gradua\u00e7\u00e3o em Ci\u00eancias Farmac\u00eauticas, Instituto de Ci\u00eancias da Sa\u00fade, Universidade Federal do Par\u00e1, Belem 66075-900, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0741-273X","authenticated-orcid":false,"given":"Bruna de A.","family":"Guimar\u00e3es","sequence":"additional","affiliation":[{"name":"Laborat\u00f3rio de Qu\u00edmica dos Produtos Naturais, Centro de Ci\u00eancias Biol\u00f3gicas e da Sa\u00fade, Universidade do Estado do Par\u00e1, Belem 66087-662, Brazil"},{"name":"Programa de P\u00f3s-Gradua\u00e7\u00e3o em Qu\u00edmica, Universidade Federal do Par\u00e1, Belem 66075-900, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0100-644X","authenticated-orcid":false,"given":"Rosa Helena V.","family":"Mour\u00e3o","sequence":"additional","affiliation":[{"name":"Laborat\u00f3rio de Bioprospec\u00e7\u00e3o e Biologia Experimental, Universidade Federal do Oeste do Par\u00e1, Santarem 68035-110, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2201-8570","authenticated-orcid":false,"given":"Jos\u00e9 Guilherme S.","family":"Maia","sequence":"additional","affiliation":[{"name":"Programa de P\u00f3s-Gradua\u00e7\u00e3o em Ci\u00eancias Farmac\u00eauticas, Instituto de Ci\u00eancias da Sa\u00fade, Universidade Federal do Par\u00e1, Belem 66075-900, Brazil"},{"name":"Programa de P\u00f3s-Gradua\u00e7\u00e3o em Qu\u00edmica, Universidade Federal do Par\u00e1, Belem 66075-900, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3639-0528","authenticated-orcid":false,"given":"William N.","family":"Setzer","sequence":"additional","affiliation":[{"name":"Aromatic Plant Research Center, 230 N 1200 E, Suite 100, Lehi, UT 84043, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9351-876X","authenticated-orcid":false,"given":"Joyce Kelly do R.","family":"da Silva","sequence":"additional","affiliation":[{"name":"Programa de P\u00f3s-Gradua\u00e7\u00e3o em Qu\u00edmica, Universidade Federal do Par\u00e1, Belem 66075-900, Brazil"},{"name":"Programa de P\u00f3s-Gradua\u00e7\u00e3o em Biotecnologia, Universidade Federal do Par\u00e1, Belem 66075-900, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1365-3513","authenticated-orcid":false,"given":"Pablo Luis B.","family":"Figueiredo","sequence":"additional","affiliation":[{"name":"Laborat\u00f3rio de Qu\u00edmica dos Produtos Naturais, Centro de Ci\u00eancias Biol\u00f3gicas e da Sa\u00fade, Universidade do Estado do Par\u00e1, Belem 66087-662, Brazil"},{"name":"Programa de P\u00f3s-Gradua\u00e7\u00e3o em Ci\u00eancias Farmac\u00eauticas, Instituto de Ci\u00eancias da Sa\u00fade, Universidade Federal do Par\u00e1, Belem 66075-900, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2023,11,14]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","unstructured":"da Trindade, R.C.S., Xavier, J.K.A.M., Setzer, W.N., Maia, J.G.S., and da Silva, J.K.R. (2021). Chemical Diversity and Therapeutic Effects of Essential Oils of Aniba Species from the Amazon: A Review. Plants, 10.","DOI":"10.3390\/plants10091854"},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"104","DOI":"10.2307\/2666133","article-title":"Phylogeny and Historical Biogeography of Lauraceae: Evidence from the Chloroplast and Nuclear Genomes","volume":"88","author":"Chanderbali","year":"2001","journal-title":"Ann. Mo. Bot. Gard."},{"key":"ref_3","unstructured":"(2023, November 07). Lauraceae in Flora e Funga do Brasil. Jardim Bot\u00e2nico do Rio de Janeiro, Available online: https:\/\/floradobrasil.jbrj.gov.br\/FB143."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"2139","DOI":"10.4314\/tjpr.v14i11.28","article-title":"A Review on Chemical Constituents and Biological Activities of the Genus Beilschmiedia (Lauraceae)","volume":"14","author":"Salleh","year":"2015","journal-title":"Trop. J. Pharm. Res."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"1054","DOI":"10.1055\/a-0943-1908","article-title":"Chemical Composition and Biological Activities of Essential Oils in the Family Lauraceae: A Systematic Review of the Literature","volume":"85","author":"Damasceno","year":"2019","journal-title":"Planta Med."},{"key":"ref_6","doi-asserted-by":"crossref","unstructured":"Xavier, J.K.A.M., Maia, L., Figueiredo, P.L.B., Folador, A., Ramos, A.R., Andrade, E.H., Maia, J.G.S., Setzer, W.N., and da Silva, J.K.R. (2021). Essential Oil Composition and DNA Barcode and Identification of Aniba Species (Lauraceae) Growing in the Amazon Region. Molecules, 26.","DOI":"10.3390\/molecules26071914"},{"key":"ref_7","doi-asserted-by":"crossref","unstructured":"de Oliveira, F.P., Ana Carolina, A.C.B., de Lima, E.J.S.P., Silva, V.R., de S. Santos, L., da Anuncia\u00e7\u00e3o, T.A., Nogueira, M.L., Soares, M.B.P., Dias, R.B., and Gurgel Rocha, C.A. (2021). Essential Oil from Bark of Aniba parviflora (Meisn.) Mez (Lauraceae) Reduces HepG2 Cell Proliferation and Inhibits Tumor Development in a Xenograft Model. Chem. Biodivers., 18.","DOI":"10.1002\/cbdv.202000938"},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"699","DOI":"10.3389\/fphar.2020.00699","article-title":"Aniba canelilla (Kunth) Mez (Lauraceae): A Review of Ethnobotany, Phytochemical, Antioxidant, Anti-Inflammatory, Cardiovascular, and Neurological Properties","volume":"11","author":"Pereira","year":"2020","journal-title":"Front. Pharmacol."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"e15446","DOI":"10.1016\/j.heliyon.2023.e15446","article-title":"Use of Lavandula Angustifolia Essential Oil as a Complementary Therapy in Adult Health Care: A Scoping Review","volume":"9","author":"Dantas","year":"2023","journal-title":"Heliyon"},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"101","DOI":"10.1016\/j.ibiod.2014.12.007","article-title":"Evaluation of Five Essential Oils as Botanical Acaricides against the Strawberry Spider Mite Tetranychus Turkestani Ugarov and Nikolskii","volume":"98","author":"Ramezani","year":"2015","journal-title":"Int. Biodeterior. Biodegrad."},{"key":"ref_11","doi-asserted-by":"crossref","unstructured":"de Oliveira Carvalho, I., Purgato, G.A., P\u00edccolo, M.S., Pizziolo, V.R., Coelho, R.R., Diaz-Mu\u00f1oz, G., and Alves Nogueira Diaz, M. (2020). In Vitro Anticariogenic and Antibiofilm Activities of Toothpastes Formulated with Essential Oils. Arch. Oral Biol., 117.","DOI":"10.1016\/j.archoralbio.2020.104834"},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"780","DOI":"10.1016\/j.bcp.2012.12.012","article-title":"The Vasorelaxant Effects of 1-Nitro-2-Phenylethane Involve Stimulation of the Soluble Guanylate Cyclase-CGMP Pathway","volume":"85","author":"Brito","year":"2013","journal-title":"Biochem. Pharmacol."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"709","DOI":"10.1016\/j.ejps.2012.12.033","article-title":"Vasorelaxant Effects of 1-Nitro-2-Phenylethane, the Main Constituent of the Essential Oil of Aniba canelilla, in Superior Mesenteric Arteries from Spontaneously Hypertensive Rats","volume":"48","author":"Interaminense","year":"2013","journal-title":"Eur. J. Pharm. Sci."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"555","DOI":"10.1016\/j.phymed.2008.10.007","article-title":"Antinociceptive Activity of 1-Nitro-2-Phenylethane, the Main Component of Aniba canelilla Essential Oil","volume":"16","author":"Santana","year":"2009","journal-title":"Phytomedicine"},{"key":"ref_15","doi-asserted-by":"crossref","unstructured":"Olender, D., \u017bwawiak, J., and Zaprutko, L. (2018). Multidirectional Efficacy of Biologically Active Nitro Compounds Included in Medicines. Pharmaceuticals, 11.","DOI":"10.3390\/ph11020054"},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"2233","DOI":"10.3390\/molecules16032233","article-title":"Analgesic-like Activity of Essential Oils Constituents","volume":"16","year":"2011","journal-title":"Molecules"},{"key":"ref_17","doi-asserted-by":"crossref","unstructured":"da Fons\u00eaca, D.V., da Silva Maia Bezerra Filho, C., Lima, T.C., de Almeida, R.N., and de Sousa, D.P. (2019). Anticonvulsant Essential Oils and Their Relationship with Oxidative Stress in Epilepsy. Biomolecules, 9.","DOI":"10.3390\/biom9120835"},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"216","DOI":"10.1016\/S0367-326X(99)00150-1","article-title":"Constituents of Aromatic Plants: I. Methyleugenol","volume":"71","author":"Silano","year":"2000","journal-title":"Fitoterapia"},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"69","DOI":"10.1016\/S0305-1978(02)00088-1","article-title":"Seasonal Essential Oil Variation of Aniba canelilla","volume":"31","author":"Taveira","year":"2003","journal-title":"Biochem. Syst. Ecol."},{"key":"ref_20","doi-asserted-by":"crossref","unstructured":"Barros, L.d.S.P., Santos da Cruz, E.d.N., de Ara\u00fajo Guimar\u00e3es, B., Setzer, W.N., Veras Mour\u00e3o, R.H., do Ros\u00e1rio da Silva, J.K., Silva da Costa, J., and Baia Figueiredo, P.L. (2022). Chemometric Analysis of the Seasonal Variation in the Essential Oil Composition and Antioxidant Activity of a New Geraniol Chemotype of Lippia alba (Mill.) N.E.Br. Ex Britton & P. Wilson from the Brazilian Amazon. Biochem. Syst. Ecol., 105.","DOI":"10.1016\/j.bse.2022.104503"},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"83","DOI":"10.1590\/0102-778620130054","article-title":"Estudo Dos Eventos Extremos de Precipita\u00e7\u00e3o Ocorridos Em 2009 No Estado Do Par\u00e1","volume":"29","author":"Saraiva","year":"2014","journal-title":"Rev. Bras. Meteorol."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"9422","DOI":"10.1021\/jf071928e","article-title":"Antioxidant Capacity and Cytotoxicity of Essential Oil and Methanol Extract of Aniba canelilla (H.B.K.) Mez","volume":"55","author":"Sousa","year":"2007","journal-title":"J. Agric. Food Chem."},{"key":"ref_23","doi-asserted-by":"crossref","unstructured":"Santos, P.V.L., da Cruz, E.d.N.S., Barroso, A.d.S., Mour\u00e3o, R.H.V., Setzer, W.N., da Silva, J.K., do Nascimento, W.M.O., da Costa, J.S., and Figueiredo, P.L.B. (2022). Chemometric Analysis of the Seasonal Variation in the Essential Oil Composition of Psidium Acutangulum Growing in the Brazilian Amazon. Biochem. Syst. Ecol., 105.","DOI":"10.1016\/j.bse.2022.104528"},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"213","DOI":"10.1002\/ffj.1875","article-title":"Factors Affecting Secondary Metabolite Production in Plants: Volatile Components and Essential Oils","volume":"23","author":"Figueiredo","year":"2008","journal-title":"Flavour Fragr. J."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"674","DOI":"10.1002\/ffj.1648","article-title":"Essential Oil of Wild Ocotea quixos (Lam.) Kosterm. (Lauraceae) Leaves from Amazonian Ecuador","volume":"21","author":"Sacchetti","year":"2006","journal-title":"Flavour Fragr. J."},{"key":"ref_26","unstructured":"Adams, R.P. (2017). Identification of Essential Oil Components by Gas Chromatography\/Mass Spectrometry, Allured Publishing Corporation."},{"key":"ref_27","unstructured":"Mondello, L. (2011). FFNSC 2: Flavors and Fragrances of Natural and Synthetic Compounds,Mass Spectral Database, John Wiley & Sons Inc."},{"key":"ref_28","doi-asserted-by":"crossref","unstructured":"Cardoso, E.K.S., Kubota, K., Luz, D.A., Mendes, P.F.S., Figueiredo, P.L.B., Lima, R.R., Maia, C.S.F., and Fontes-J\u00fanior, E.A. (2022). Aniba canelilla (Kunth) Mez (Lauraceae) Essential Oil: Effects on Oxidative Stress and Vascular Permeability. Antioxidants, 11.","DOI":"10.3390\/antiox11101903"},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"1065","DOI":"10.1590\/0100-67622015000600009","article-title":"An\u00e1lise Do Efeito Da Sazonalidade Sobre O Rendimento Do \u00d3leo Essencial Das Folhas De Nectandra grandiflora Nees1","volume":"39","author":"Bianchini","year":"2015","journal-title":"Rev. \u00c1rvore"},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"41334","DOI":"10.34117\/bjdv6n6-610","article-title":"Avalia\u00e7\u00e3o Sazonal Do Rendimento e Composi\u00e7\u00e3o Qu\u00edmica Do \u00d3leo Essencial Das Folhas de Aniba parviflora (Meisn) Mez. (Lauraceae)","volume":"6","author":"Silva","year":"2020","journal-title":"Braz. J. Dev."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"34","DOI":"10.1016\/j.jphotobiol.2016.05.012","article-title":"Antioxidant Activity and Potential Photoprotective from Amazon Native Flora Extracts","volume":"161","author":"Martins","year":"2016","journal-title":"J. Photochem. Photobiol. B Biol."},{"key":"ref_32","doi-asserted-by":"crossref","unstructured":"Santos, P.V.L., da Cruz, E.d.N.S., Nunes, J.d.A., Mour\u00e3o, R.H.V., do Nascimento, W.M.O., Maia, J.G.S., and Figueiredo, P.L.B. (2023). Seasonal Influence on Volatile Composition of Psidium friedrichsthalianum Leaves, Sampled in the Brazilian Amazon. Horticulturae, 9.","DOI":"10.3390\/horticulturae9070768"},{"key":"ref_33","doi-asserted-by":"crossref","unstructured":"da Cruz, E.d.N.S., Peixoto, L.d.S., da Costa, J.S., Mour\u00e3o, R.H.V., do Nascimento, W.M.O., Maia, J.G.S., Setzer, W.N., da Silva, J.K., and Figueiredo, P.L.B. (2022). Seasonal Variability of a Caryophyllane Chemotype Essential Oil of Eugenia Patrisii Vahl Occurring in the Brazilian Amazon. Molecules, 27.","DOI":"10.3390\/molecules27082417"},{"key":"ref_34","unstructured":"(2023, September 23). Instituto Nacional de Metereologia (INMET), Brazilian Government, Available online: http:\/\/www.inmet.gov.br\/portal."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"30","DOI":"10.1016\/j.jep.2018.12.011","article-title":"Composition, Antioxidant Capacity and Cytotoxic Activity of Eugenia Uniflora L. Chemotype-Oils from the Amazon","volume":"232","author":"Figueiredo","year":"2019","journal-title":"J. Ethnopharmacol."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"463","DOI":"10.1016\/S0021-9673(01)80947-X","article-title":"A Generalization of the Retention Index System Including Linear Temperature Programmed Gas\u2014Liquid Partition Chromatography","volume":"11","author":"Kratz","year":"1963","journal-title":"J. Chromatogr. A"},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"4156","DOI":"10.1021\/jf000227d","article-title":"Radical-Scavenging Activities of Citrus Essential Oils and Their Components: Detection Using 1,1-Diphenyl-2-Icrylhydrazyl","volume":"48","author":"Choi","year":"2000","journal-title":"J. Agric. Food Chem."},{"key":"ref_38","doi-asserted-by":"crossref","unstructured":"da Silva, J.K.R., Andrade, E.H.A., Barreto, L., da Silva, N., Ribeiro, A., Montenegro, R., and Maia, J. (2017). Chemical Composition of Four Essential Oils of Eugenia from the Brazilian Amazon and Their Cytotoxic and Antioxidant Activity. Medicines, 4.","DOI":"10.3390\/medicines4030051"}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/28\/22\/7573\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T21:22:32Z","timestamp":1760131352000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/28\/22\/7573"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2023,11,14]]},"references-count":38,"journal-issue":{"issue":"22","published-online":{"date-parts":[[2023,11]]}},"alternative-id":["molecules28227573"],"URL":"https:\/\/doi.org\/10.3390\/molecules28227573","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2023,11,14]]}}}