{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T03:04:46Z","timestamp":1760151886488,"version":"build-2065373602"},"reference-count":39,"publisher":"MDPI AG","issue":"23","license":[{"start":{"date-parts":[[2022,11,30]],"date-time":"2022-11-30T00:00:00Z","timestamp":1669766400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Consejo Nacional de Ciencia y Tecnolog\u00eda (CONACYT)","award":["773862"],"award-info":[{"award-number":["773862"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["IJMS"],"abstract":"<jats:p>Inflammation is implicated in a wide variety of physiological and pathological processes. Plants are an important source of active anti-inflammatory compounds. The compound 3, 5-diprenyl-4-hydroxyacetophenone (DHAP) was isolated from the dichloromethane extract of the aerial parts of Ageratina pazcuarensis by chromatography and identified by spectroscopic (IR, NMR) and spectrometric (GC-MS) methods. Anti-inflammatory activity was evaluated on ear edema mouse induced with 12-O-tetradecanoylphorbol 13-acetate (TPA) at 2 mg\/ear. The antioxidant activity of DHAP was determined using DPPH assay. Cell viability was tested in J774A.1 macrophages, the levels of NO, TNF-\u03b1, IL-1\u03b2, IL-6, and IL-10 production in macrophages stimulated with lipopolysaccharide (LPS), and membrane lysis induced by hypotonic solution in erythrocytes were evaluated. DHAP diminished the ear edema mouse in 70.10%, and it had scavenger effect against the radical with IC50 of 26.00 \u00b1 0.37 \u00b5g\/mL. Likewise, 91.78 \u00b5M of this compound inhibited the production of NO (38.96%), IL-1\u03b2 (55.56%), IL-6 (51.62%), and TNF-\u03b1 (59.14%) in macrophages and increased the levels of IL-10 (61.20%). Finally, 25 and 50 \u00b5g\/mL DHAP provided the greatest protection against erythrocyte membrane lysis. These results demonstrate that DHAP has anti-inflammatory activity.<\/jats:p>","DOI":"10.3390\/ijms232315012","type":"journal-article","created":{"date-parts":[[2022,11,30]],"date-time":"2022-11-30T03:49:13Z","timestamp":1669780153000},"page":"15012","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":1,"title":["Anti-Inflammatory Activity of 3, 5-Diprenyl-4-hydroxyacetophenone Isolated from Ageratina pazcuarensis"],"prefix":"10.3390","volume":"23","author":[{"given":"Sarai","family":"Rojas-Jim\u00e9nez","sequence":"first","affiliation":[{"name":"Doctorado en Ciencias Biol\u00f3gicas y de la Salud, Universidad Aut\u00f3noma Metropolitana-Xochimilco, Calzada del Hueso 1100, Coyoac\u00e1n 04960, Ciudad de M\u00e9xico, Mexico"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Mar\u00eda Salud","family":"P\u00e9rez-Guti\u00e9rrez","sequence":"additional","affiliation":[{"name":"Departamento de Sistemas Biol\u00f3gicos, Universidad Aut\u00f3noma Metropolitana-Xochimilco, Calzada del Hueso 1100, Coyoac\u00e1n 04960, Ciudad de M\u00e9xico, Mexico"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Ernesto","family":"S\u00e1nchez-Mendoza","sequence":"additional","affiliation":[{"name":"Departamento de Sistemas Biol\u00f3gicos, Universidad Aut\u00f3noma Metropolitana-Xochimilco, Calzada del Hueso 1100, Coyoac\u00e1n 04960, Ciudad de M\u00e9xico, Mexico"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1172-8721","authenticated-orcid":false,"given":"Rubria Marlen","family":"Mart\u00ednez-Casares","sequence":"additional","affiliation":[{"name":"Departamento de Sistemas Biol\u00f3gicos, Universidad Aut\u00f3noma Metropolitana-Xochimilco, Calzada del Hueso 1100, Coyoac\u00e1n 04960, Ciudad de M\u00e9xico, Mexico"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Nimsi","family":"Campos-Xolalpa","sequence":"additional","affiliation":[{"name":"Departamento de Sistemas Biol\u00f3gicos, Universidad Aut\u00f3noma Metropolitana-Xochimilco, Calzada del Hueso 1100, Coyoac\u00e1n 04960, Ciudad de M\u00e9xico, Mexico"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7676-2325","authenticated-orcid":false,"given":"Mar\u00eda Guadalupe","family":"Valladares-Cisneros","sequence":"additional","affiliation":[{"name":"Facultad de Ciencias Qu\u00edmicas e Ingenier\u00eda, Universidad Aut\u00f3noma del Estado de Morelos, Avenida Universidad 1001, Cuernavaca 62209, Morelos, Mexico"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0183-4560","authenticated-orcid":false,"given":"David Osvaldo","family":"Salinas-S\u00e1nchez","sequence":"additional","affiliation":[{"name":"Centro de Investigaci\u00f3n de Biodiversidad y Conservaci\u00f3n, Universidad Aut\u00f3noma del Estado de Morelos, Avenida Universidad 1001, Cuernavaca 62209, Morelos, Mexico"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2022,11,30]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","unstructured":"Badria, F. (2012). State of the art of anti-inflammatory drugs. Pharmacotherapy, Intech.","DOI":"10.5772\/1983"},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"696","DOI":"10.3389\/fimmu.2018.00696","article-title":"Macrophage Lamin A\/C regulates inflammation and development of obesity-induced insulin resistance","volume":"9","author":"Kim","year":"2018","journal-title":"Front. Immunol."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"154","DOI":"10.3389\/fimmu.2018.00154","article-title":"Protein of TNF-\u03b1 and IL6 pathways are elevated in serum of type-1 diabetes patients with microalbuminuria","volume":"9","author":"Purohit","year":"2018","journal-title":"Front. Immunol."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1007\/978-3-030-01099-7_1","article-title":"Chemistry and biology of selected Mexican medicinal plants","volume":"Volume 108","author":"Kinghorn","year":"2019","journal-title":"Progress in the Chemistry of Organic Natural Products"},{"key":"ref_5","first-page":"77","article-title":"Etnobot\u00e1nica de compuestas Argentinas con especial referencia a su uso farmacol\u00f3gico (Primera parte)","volume":"3","author":"Zardini","year":"1984","journal-title":"Acta Farm. Bonaer."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"240","DOI":"10.1016\/j.fitote.2004.12.001","article-title":"Antibacterial activity of Eupatorium glandulosum leaves","volume":"70","author":"Sasikumar","year":"2005","journal-title":"Fitoterapia"},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"74","DOI":"10.1016\/j.jep.2009.08.007","article-title":"Clinical trial to compare the effectiveness of two concentrations of the Ageratina pichinchensis in the topical treatment of onychomycosis","volume":"126","author":"Romero","year":"2009","journal-title":"J. Ethopharmacol."},{"key":"ref_8","unstructured":"Monroy, O.C., and Castillo, E.P. (2007). Plantas medicinales utilizadas en el estado de Morelos. Ed. Universidad Aut\u00f3noma del Estado de Morelos, Comisi\u00f3n Nacional para el Conocimiento y Uso de la Biodiversidad Universidad 2\u00aa Ed., p. 69."},{"key":"ref_9","doi-asserted-by":"crossref","unstructured":"Rivero-Cruz, I., Guti\u00e9rrez-Gonz\u00e1lez, J.A., P\u00e9rez-V\u00e1squez, A., Villase\u00f1or, J.L., and Mata, R. (Comb. Chem. High Throughput Screen., 2022). The genus Ageratina (Asteraceae) in America: An insight into its chemistry, and pharmacological potential, Comb. Chem. High Throughput Screen., Advance online publication.","DOI":"10.2174\/1386207325666220908093541"},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"1113","DOI":"10.1016\/S0031-9422(00)82360-2","article-title":"Acetophenones and terpenoids from Senecio gallzcus","volume":"26","author":"Urones","year":"1987","journal-title":"Phytochemistry"},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"11","DOI":"10.1016\/j.fitote.2013.03.015","article-title":"Antinociceptive effect and gastroprotective mechanisms of 3,5-diprenyl-4-hydroxyacetophenone from Ageratina pichinchensis","volume":"87","author":"Silverio","year":"2013","journal-title":"Fitoterapia"},{"key":"ref_12","doi-asserted-by":"crossref","unstructured":"S\u00e1nchez-Ramos, M., Alvarez, L., Romero-Estrada, A., Bernab\u00e9-Antonio, A., Marquina-Bahena, S., and Cruz-Sosa, F. (2020). Establishment of a cell suspension culture of Ageratina pichinchensis (Kunth) for the improved production of anti-inflammatory compounds. Plants, 9.","DOI":"10.20944\/preprints202008.0443.v1"},{"key":"ref_13","first-page":"82","article-title":"Anti-inflammatory action of Lannea coromandelica by HRBC membrane stabilization","volume":"62","author":"Gandhisan","year":"1991","journal-title":"Fitoterapia"},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"415","DOI":"10.2174\/1385272801666220126162734","article-title":"Antioxidants and free radical scavergers of natual origin","volume":"1","author":"Potterat","year":"1997","journal-title":"Curr. Org. Chem."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"5276130","DOI":"10.1155\/2016\/5276130","article-title":"Role of Antioxidants and Natural Products in Inflammation","volume":"2016","author":"Arulselvan","year":"2016","journal-title":"Oxid. Med. Cell. Longev."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"48","DOI":"10.3390\/oxygen2020006","article-title":"Free Radical Properties, Source and Targets, Antioxidant Consumption and Health","volume":"2","author":"Martemucci","year":"2022","journal-title":"Oxygen"},{"key":"ref_17","first-page":"9252","article-title":"Antioxidant and anti-inflammatory activities of essential oil","volume":"15","author":"Graca","year":"2010","journal-title":"A Short Rev. Mol."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"119655","DOI":"10.1016\/j.lfs.2021.119655","article-title":"Effect of baricitinib on TPA-induced psoriasis like skin inflammation","volume":"279","author":"Hiraganahalli","year":"2021","journal-title":"Life Sci."},{"key":"ref_19","first-page":"354","article-title":"Suppression of 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced skin inflammation in mice by transduced Tat-Annexin protein BMB","volume":"45","author":"Lee","year":"2012","journal-title":"Rep. Korean Soc. Biochem. Mol. Sci."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"1407","DOI":"10.1158\/0008-5472.CAN-06-2149","article-title":"An emerging role for endothelial nitric oxide synthase in chronic inflammation and cancer","volume":"67","author":"Ying","year":"2007","journal-title":"Cancer Res."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"935","DOI":"10.1016\/j.cell.2010.02.043","article-title":"Anti-inflammatory agents: Present and future","volume":"140","author":"Dinarello","year":"2010","journal-title":"Cell"},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"2095","DOI":"10.1182\/blood.V87.6.2095.bloodjournal8762095","article-title":"Biologic basis for interleukin-1 in disease","volume":"87","author":"Dinarello","year":"1996","journal-title":"Blood."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"92","DOI":"10.1016\/j.it.2014.12.008","article-title":"Versatile functions for IL-6 in metabolism and cancer","volume":"36","author":"Mauer","year":"2015","journal-title":"Trends Immunol."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"S3","DOI":"10.1186\/ar1917","article-title":"Interleukin-6 and chronic inflammation","volume":"8","author":"Gabay","year":"2006","journal-title":"Arthritis Res Ther."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"1215","DOI":"10.1093\/rheumatology\/keq031","article-title":"Transmembrane TNF-alpha: Structure, function and interaction with anti-TNF agents","volume":"49","author":"Horiuchi","year":"2010","journal-title":"Rheumatology"},{"key":"ref_26","doi-asserted-by":"crossref","unstructured":"Jang, D.I., Lee, A.H., Shin, H.Y., Song, H.R., Park, J.H., Kang, T.B., Lee, S.R., and Yang, S.H. (2021). The role of tumor necrosis factor alpha (TNF-\u03b1) in autoimmune disease and current TNF-\u03b1 inhibitors in therapeutics. Int. J. Mol. Sci., 22.","DOI":"10.3390\/ijms22052719"},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"1028","DOI":"10.1038\/nm.2807","article-title":"Mechanisms of fibrosis: Therapeutic translation for fibrotic disease","volume":"18","author":"Wynn","year":"2012","journal-title":"Nat. Med."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"170","DOI":"10.1038\/nri2711","article-title":"The regulation of IL-10 production by immune cells","volume":"10","author":"Saraiva","year":"2010","journal-title":"Nat. Rev. Immunol."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"231","DOI":"10.1038\/sj.bjp.0705776","article-title":"Measuring reactive species and oxidative damage in vivo and in cell culture: How should you do it and what do the results mean?","volume":"142","author":"Halliwell","year":"2004","journal-title":"Br. J. Pharmacol."},{"key":"ref_30","first-page":"44","article-title":"Membrane stabilization as a mechanism of anti-inflammatory and thrombolytic activities of ethanolic extract of aereal parts of Spondiasis pinanata (Family: Anacardiaceae)","volume":"2","author":"Labu","year":"2015","journal-title":"Archives"},{"key":"ref_31","first-page":"81","article-title":"In vitro studies suggest probable mechanism of eucalyptus oil for anti-inflammatory and anti-arthritic activity","volume":"2","author":"Rahman","year":"2012","journal-title":"Int. J. Phyto. Pharm."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"460","DOI":"10.1016\/j.sjbs.2018.09.005","article-title":"In vitro anti-inflammatory and antimicrobial potential of leaf extract from Artemisia nilagirica (Clarke) Pamp","volume":"26","author":"Parameswari","year":"2019","journal-title":"Saudi J. Biol. Sci."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"422","DOI":"10.1007\/s11418-017-1074-9","article-title":"p-Hydroxyacetophenone suppresses nuclear factor-\u03baB-related inflammation in nociceptive and inflammatory animal models","volume":"71","year":"2017","journal-title":"J. Nat. Med."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"1594","DOI":"10.3389\/fphar.2019.01594","article-title":"P-hydroxyacetophenone ameliorates alcohol-induced steatosis and oxidative stress via the NF-\u03baB signaling pathway in zebrafish and hepatocytes","volume":"10","author":"Huang","year":"2020","journal-title":"Front. Pharmacol."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"e18000080","DOI":"10.1002\/cbdv.201800080","article-title":"New Acetophenone Derivatives from Acronychia oligophlebia and Their Anti-inflammatory and Antioxidant Activities","volume":"15","author":"Chen","year":"2018","journal-title":"Chem. Biodivers."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"335","DOI":"10.1007\/BF01967298","article-title":"Edema and cell infiltration in the phorbol ester-treated mouse ear are temporally separate and can be differentially modulated by pharmacological agents","volume":"26","author":"Young","year":"1989","journal-title":"Agents Actions"},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"169","DOI":"10.3923\/rjmp.2011.169.179","article-title":"In vitro antioxidant property of some Indian medicinal plants","volume":"5","author":"Chanda","year":"2011","journal-title":"Res. J. Med. Plants."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"55","DOI":"10.1016\/0022-1759(83)90303-4","article-title":"Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxicity assays","volume":"65","author":"Mosmann","year":"1983","journal-title":"J. Immunol. Methods"},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"276","DOI":"10.3390\/s30800276","article-title":"Measurement of nitric oxide production in biological systems by using Griess reaction assay","volume":"3","author":"Sun","year":"2003","journal-title":"Sensors"}],"container-title":["International Journal of Molecular Sciences"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1422-0067\/23\/23\/15012\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T01:30:09Z","timestamp":1760146209000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1422-0067\/23\/23\/15012"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2022,11,30]]},"references-count":39,"journal-issue":{"issue":"23","published-online":{"date-parts":[[2022,12]]}},"alternative-id":["ijms232315012"],"URL":"https:\/\/doi.org\/10.3390\/ijms232315012","relation":{},"ISSN":["1422-0067"],"issn-type":[{"type":"electronic","value":"1422-0067"}],"subject":[],"published":{"date-parts":[[2022,11,30]]}}}