{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,5,15]],"date-time":"2026-05-15T09:12:32Z","timestamp":1778836352045,"version":"3.51.4"},"reference-count":35,"publisher":"MDPI AG","issue":"10","license":[{"start":{"date-parts":[[2026,5,15]],"date-time":"2026-05-15T00:00:00Z","timestamp":1778803200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"DGAPA-PAPIIT-UNAM","award":["IG201024"],"award-info":[{"award-number":["IG201024"]}]},{"name":"DGAPA-PAPIIT-UNAM","award":["IN202725"],"award-info":[{"award-number":["IN202725"]}]},{"name":"Secihti","award":["ANR-Conacyt 188565"],"award-info":[{"award-number":["ANR-Conacyt 188565"]}]},{"name":"Secihti","award":["CF-2019-51488"],"award-info":[{"award-number":["CF-2019-51488"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Jacareubin (2), nujiangexanthone A, and \u03b1-mangostin display the highest anti-allergic effects among the active xantones through still not well-known mechanisms. This study investigates the SAR of jacareubin, its precursor xanthone V (1) and their peracetylated (1a and 2a), permethylated (1b and 2b) derivatives and their anti-allergic and anti-inflammatory effects. To characterize the inhibitory effect of jacareubin, 2a and 2b on the anaphylactic reaction, we first utilized in vitro models of bone marrow derived mast cells (BMMCs), determining their capacity of inhibiting the IgE\/Antigen-induced degranulation, myeloperoxidase (MPO), and xanthine oxidase (XO) activation. Also, we utilized in vivo models of passive cutaneous anaphylaxis (PCA) and TPA-induced ear edema. In vitro tests showed that the compound 2b was more effective than jacareubin in the inhibition of BMMCs degranulation. Besides, in vivo models of PCA revealed that the fourth cyclized ring of jacareubin is the critical structural element for anti-allergic efficacy, as compound 1 was less effective. Additionally, hydroxyl groups were found to be essential for inhibiting MPO. Jacareubin was the only tested xanthone that directly inhibited XO, a result supported by molecular docking. Overall, jacareubin represents a promising multi-target scaffold that could be used for developing new treatments for inflammatory and allergic diseases.<\/jats:p>","DOI":"10.3390\/molecules31101666","type":"journal-article","created":{"date-parts":[[2026,5,15]],"date-time":"2026-05-15T08:50:12Z","timestamp":1778835012000},"page":"1666","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Jacareubin Derivatives Increase Their Anti-Allergic Activity"],"prefix":"10.3390","volume":"31","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-5501-2496","authenticated-orcid":false,"given":"Rosario","family":"Tavera-Hern\u00e1ndez","sequence":"first","affiliation":[{"name":"Instituto de Qu\u00edmica, Universidad Nacional Aut\u00f3noma de M\u00e9xico, Ciudad Universitaria, Mexico City 04510, Mexico"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0383-0320","authenticated-orcid":false,"given":"Jesabel","family":"P\u00e9rez-Rodr\u00edguez","sequence":"additional","affiliation":[{"name":"Posgrado en Producci\u00f3n Animal, Departamento de Zootecnia, Universidad Aut\u00f3noma Chapingo, Chapingo, Texcoco 56230, Mexico"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0900-6017","authenticated-orcid":false,"given":"Antonio","family":"Nieto-Camacho","sequence":"additional","affiliation":[{"name":"Instituto de Qu\u00edmica, Universidad Nacional Aut\u00f3noma de M\u00e9xico, Ciudad Universitaria, Mexico City 04510, Mexico"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Omar Noel","family":"Medina-Campos","sequence":"additional","affiliation":[{"name":"Facultad de Qu\u00edmica, Departamento de Biolog\u00eda, Universidad Nacional Aut\u00f3noma de M\u00e9xico, Mexico City 04510, Mexico"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6628-4411","authenticated-orcid":false,"given":"Jos\u00e9","family":"Pedraza-Chaverri","sequence":"additional","affiliation":[{"name":"Facultad de Qu\u00edmica, Departamento de Biolog\u00eda, Universidad Nacional Aut\u00f3noma de M\u00e9xico, Mexico City 04510, Mexico"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5064-2381","authenticated-orcid":false,"given":"Francisco","family":"Le\u00f3n","sequence":"additional","affiliation":[{"name":"Department of Drug Discovery and Biomedical Sciences, College of Pharmacy, University of South Carolina, Columbia, SC 29208, USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7332-3829","authenticated-orcid":false,"given":"Claudia","family":"Gonz\u00e1lez-Espinosa","sequence":"additional","affiliation":[{"name":"Departamento de Farmacobiolog\u00eda y Centro de Investigaci\u00f3n Sobre el Envejecimiento, Centro de Investigaci\u00f3n y de Estudios Avanzados del Instituto Polit\u00e9cnico Nacional, Sede Sur, Tlalpan, Mexico City 14330, Mexico"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6187-4877","authenticated-orcid":false,"given":"Manuel","family":"Jim\u00e9nez-Estrada","sequence":"additional","affiliation":[{"name":"Instituto de Qu\u00edmica, Universidad Nacional Aut\u00f3noma de M\u00e9xico, Ciudad Universitaria, Mexico City 04510, Mexico"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Ricardo","family":"Reyes-Chilpa","sequence":"additional","affiliation":[{"name":"Instituto de Qu\u00edmica, Universidad Nacional Aut\u00f3noma de M\u00e9xico, Ciudad Universitaria, Mexico City 04510, Mexico"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3278-2348","authenticated-orcid":false,"given":"Jorge Ivan","family":"Castillo-Arellano","sequence":"additional","affiliation":[{"name":"Instituto de Qu\u00edmica, Universidad Nacional Aut\u00f3noma de M\u00e9xico, Ciudad Universitaria, Mexico City 04510, Mexico"},{"name":"Laboratorio de Reprogramaci\u00f3n Celular, Instituto Nacional de Neurolog\u00eda y Neurocirug\u00eda Manuel Velasco Su\u00e1rez, Mexico City 14269, Mexico"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2026,5,15]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","unstructured":"Oriola, A.O., and Kar, P. 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