{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,3,25]],"date-time":"2026-03-25T22:51:18Z","timestamp":1774479078913,"version":"3.50.1"},"reference-count":24,"publisher":"MDPI AG","issue":"1","license":[{"start":{"date-parts":[[2017,3,16]],"date-time":"2017-03-16T00:00:00Z","timestamp":1489622400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100003593","name":"Conselho Nacional de Desenvolvimento Cient\u00edfico e Tecnol\u00f3gico","doi-asserted-by":"publisher","award":["232482\/2014-4"],"award-info":[{"award-number":["232482\/2014-4"]}],"id":[{"id":"10.13039\/501100003593","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Pharmaceuticals"],"abstract":"<jats:p>Anacardic acids are the main constituents of natural cashew nut shell liquid (CNSL), obtained via the extraction of cashew shells with hexane at room temperature. This raw material presents high technological potential due to its various biological properties. The main components of CNSL are the anacardic acids, salicylic acid derivatives presenting a side chain of fifteen carbon atoms with different degrees of unsaturation (monoene\u201315:1, diene\u201315:2, and triene\u201315:3). Each constituent was isolated by column chromatography using silica gel impregnated with silver nitrate. The structures of the compounds were characterized by nuclear magnetic resonance through complete and unequivocal proton and carbon assignments. The effect of the side chain unsaturation was also evaluated in relation to antioxidant, antifungal and anticholinesterase activities, and toxicity against Artemia salina. The triene anacardic acid provided better results in antioxidant activity assessed by the inhibition of the free radical 1,1-diphenyl-2-picrylhydrazyl (DPPH), higher cytotoxicity against A. salina, and acetylcholinesterase (AChE) inhibition. Thus, increasing the unsaturation of the side chain of anacardic acid increases its action against free radicals, AChE enzyme, and A. salina nauplii. In relation to antifungal activity, an inverse result was obtained, and the linearity of the molecule plays an important role, with monoene being the most active. In conclusion, the changes in structure of anacardic acids, which cause differences in polarity, contribute to the increase or decrease in the biological activity assessed.<\/jats:p>","DOI":"10.3390\/ph10010031","type":"journal-article","created":{"date-parts":[[2017,3,16]],"date-time":"2017-03-16T11:24:28Z","timestamp":1489663468000},"page":"31","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":78,"title":["Anacardic Acid Constituents from Cashew Nut Shell Liquid: NMR Characterization and the Effect of Unsaturation on Its Biological Activities"],"prefix":"10.3390","volume":"10","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-2766-3790","authenticated-orcid":false,"given":"Selene","family":"Morais","sequence":"first","affiliation":[{"name":"Chemistry Course, Master Course in Natural Resources, University of Cear\u00e1 State, Fortaleza, CE, Brazil"},{"name":"Post-Graduation Course in Biotechnology, University of Cear\u00e1 State, Fortaleza, CE, Brazil"},{"name":"Post-Graduation Course of Veterinary Sciences, University of Cear\u00e1 State, Fortaleza, CE, Brazil"}]},{"given":"Katherine","family":"Silva","sequence":"additional","affiliation":[{"name":"Chemistry Course, Master Course in Natural Resources, University of Cear\u00e1 State, Fortaleza, CE, Brazil"}]},{"given":"Halisson","family":"Araujo","sequence":"additional","affiliation":[{"name":"Chemistry Course, Master Course in Natural Resources, University of Cear\u00e1 State, Fortaleza, CE, Brazil"}]},{"given":"Icaro","family":"Vieira","sequence":"additional","affiliation":[{"name":"Post-Graduation Course in Biotechnology, University of Cear\u00e1 State, Fortaleza, CE, Brazil"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0746-2211","authenticated-orcid":false,"given":"Daniela","family":"Alves","sequence":"additional","affiliation":[{"name":"Post-Graduation Course of Veterinary Sciences, University of Cear\u00e1 State, Fortaleza, CE, Brazil"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8865-5954","authenticated-orcid":false,"given":"Raquel","family":"Fontenelle","sequence":"additional","affiliation":[{"name":"Curso de Ci\u00eancias Biol\u00f3gicas, Universidade Estadual Vale do Acara\u00fa, Sobral, CE, Brazil"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2861-8286","authenticated-orcid":false,"given":"Artur","family":"Silva","sequence":"additional","affiliation":[{"name":"Department of Chemistry &amp; QOPNA, University of Aveiro, 3810-193 Aveiro, Portugal"}]}],"member":"1968","published-online":{"date-parts":[[2017,3,16]]},"reference":[{"key":"ref_1","first-page":"1","article-title":"Cashew crop","volume":"30","author":"Oliveira","year":"2008","journal-title":"Rev. Bras. Frutic."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"1016","DOI":"10.1021\/jf00030a036","article-title":"Structure\u2013Antibacterial activity relationships of anacardic acids","volume":"41","author":"Kubo","year":"1993","journal-title":"J. Agric. Food Chem."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"165","DOI":"10.1016\/j.actatropica.2010.08.003","article-title":"Antioxidant, larvicidal and antiacetylcholinesterase activities of cashew nut shell liquid constituents","volume":"117","author":"Oliveira","year":"2010","journal-title":"Acta Trop."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"403","DOI":"10.1124\/jpet.111.181891","article-title":"Anacardic Acid (6-Pentadecylsalicylic Acid) Inhibits Tumor Angiogenesis by Targeting Src\/FAK\/Rho GTPases Signaling Pathway","volume":"339","author":"Wu","year":"2011","journal-title":"J. Pharmacol. Exp. Ther."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"2548","DOI":"10.1021\/jf001222j","article-title":"Novel method for isolation of major phenolic components from cashew (Anacardium occidentale L.)","volume":"49","author":"Paramashivappa","year":"2001","journal-title":"J. Agric. Food Chem."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"188","DOI":"10.1016\/j.fct.2005.06.012","article-title":"Characterization of alkyl phenols in cashew (Anacardium occidentale) products and assay of their antioxidant capacity","volume":"44","author":"Trevisan","year":"2006","journal-title":"Food Chem. Toxicol."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"555","DOI":"10.1016\/j.foodchem.2005.08.023","article-title":"Antioxidant activity of anacardic acids","volume":"99","author":"Kubo","year":"2006","journal-title":"Food Chem."},{"key":"ref_8","unstructured":"Dewick, P.M. (2004). Medicinal Natural Products\u2014A Biosynthetic Approach, John Wiley & Sons, Ltd.. [2nd ed.]."},{"key":"ref_9","first-page":"369","article-title":"Development and validation of a normal phase HPLC method for separation of anacardic acid isomers in cashew nut shell liquid","volume":"5","author":"Mantelingu","year":"2013","journal-title":"J. Chem. Pharm. Res."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"109","DOI":"10.1016\/S0021-9673(01)01194-3","article-title":"Preparative isolation and dual column high-performance liquid chromatography of ginkgolic acids from Ginkgo biloba","volume":"930","author":"Wintermans","year":"2001","journal-title":"J. Chromatogr. A"},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"133","DOI":"10.1007\/s11418-011-0564-4","article-title":"Phenolic lipid ingredients from cashew nuts","volume":"66","author":"Suo","year":"2012","journal-title":"J. Nat. Med."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"1780","DOI":"10.1021\/jf00034a049","article-title":"Bactericidal activity of anacardic acids against Streptococcus mutans and their potentiation","volume":"41","author":"Muroi","year":"1993","journal-title":"J. Agric. Food Chem."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"217","DOI":"10.1590\/S0037-86821990000400007","article-title":"Molluscacide activity of a mixture of 6-n-alkyl salicylic acids (anacardic acid) and 2 of its complexes with copper (II) and lead (II)","volume":"23","author":"Mendes","year":"1990","journal-title":"Rev. Soc. Bras. Med. Trop."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"775","DOI":"10.1016\/S0006-291X(05)80252-9","article-title":"Inhibition of lipoxygenase and prostaglandin endoperoxide synthase by anacardic acids","volume":"176","author":"Grazzini","year":"1991","journal-title":"Biochem. Biophys. Res. Commun."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"614","DOI":"10.1124\/mol.112.079020","article-title":"Anacardic Acid Inhibits the Catalytic Activity of Matrix Metalloproteinase-2 and Matrix Metalloproteinase-9","volume":"82","author":"Omanakuttan","year":"2012","journal-title":"Mol. Pharmacol."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"264","DOI":"10.1016\/j.cbi.2009.10.008","article-title":"Protective effect of anacardic acids from cashew (Anacardium occidentale) on ethanol-induced gastric damage in mice","volume":"183","author":"Morais","year":"2010","journal-title":"Chem. Biol. Interact."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"245","DOI":"10.1016\/j.bbadis.2003.12.010","article-title":"Characterization of xanthine oxidase inhibition by anacardic acids","volume":"1688","author":"Masuoka","year":"2004","journal-title":"Biochim. Biophys. Acta"},{"key":"ref_18","first-page":"125","article-title":"Assessment of Bioactivity of Indian Medicinal Plants using Brine Shrimp (Artemia salina) Lethality Assay","volume":"3","author":"Krishnaraju","year":"2005","journal-title":"Int. J. Appl. Sci. Eng."},{"key":"ref_19","first-page":"177","article-title":"Correlation between the lipophilicity and antifungal activity of some benzoxazole derivatives","volume":"41","year":"2010","journal-title":"Acta Period. Technol."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"212","DOI":"10.1590\/S0100-40422010000100036","article-title":"Utiliza\u00e7\u00e3o e recupera\u00e7\u00e3o de s\u00edlica gel impregnada com nitrato de prata","volume":"33","author":"Giacomini","year":"2010","journal-title":"Qu\u00edm. Nova"},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"88","DOI":"10.1016\/0006-2952(61)90145-9","article-title":"Featherstone. A new and rapid colorimetric determination of acetylcholinesterase activity","volume":"7","author":"Ellman","year":"1961","journal-title":"Biochem. Pharmacol."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"217","DOI":"10.1016\/S0021-9673(01)00624-0","article-title":"Screening for acetylcholinesterase inhibitors from Amaryllidaceae using silica gel thin-layer chromatography in combination with bioactivity staining","volume":"915","author":"Rhee","year":"2001","journal-title":"J. Chromatogr. A"},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"1383","DOI":"10.1111\/j.1365-2672.2007.03707.x","article-title":"Antifungal activity of essential oils of Croton species from the Brazilian Caatinga biome","volume":"104","author":"Fontenelle","year":"2008","journal-title":"J. Appl. Microbiol."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"31","DOI":"10.1055\/s-2007-971236","article-title":"Brine shrimp: A convenient general bioassay for active plant constituents","volume":"45","author":"Meyer","year":"1982","journal-title":"Planta Med."}],"container-title":["Pharmaceuticals"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1424-8247\/10\/1\/31\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T18:30:38Z","timestamp":1760207438000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1424-8247\/10\/1\/31"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2017,3,16]]},"references-count":24,"journal-issue":{"issue":"1","published-online":{"date-parts":[[2017,3]]}},"alternative-id":["ph10010031"],"URL":"https:\/\/doi.org\/10.3390\/ph10010031","relation":{},"ISSN":["1424-8247"],"issn-type":[{"value":"1424-8247","type":"electronic"}],"subject":[],"published":{"date-parts":[[2017,3,16]]}}}