{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,2,3]],"date-time":"2026-02-03T15:00:34Z","timestamp":1770130834869,"version":"3.49.0"},"reference-count":20,"publisher":"Oxford University Press (OUP)","issue":"11","license":[{"start":{"date-parts":[[2006,11,1]],"date-time":"2006-11-01T00:00:00Z","timestamp":1162339200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/academic.oup.com\/journals\/pages\/open_access\/funder_policies\/chorus\/standard_publication_model"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2006,11,1]]},"abstract":"<jats:title>Abstract<\/jats:title>\n               <jats:p>The gastroprotective effect of the sesquiterpene cyperenoic acid and seven semi-synthetic derivatives was assessed in the HCl\/ethanol-induced gastric ulcer model in mice. At doses of 25, 50 and 100 mg kg\u22121, cyperenoic acid showed a dose-dependent gastroprotective effect reducing the lesions by 45 and 75% at 50 and 100 mg kg\u22121, respectively. Seven derivatives of the sesquiterpene were prepared and their gastroprotective activity compared at 50 mg kg\u22121. The cytotoxicity of the compounds was evaluated in fibroblasts and AGS cells. At 50 mg kg\u22121, patchoulan-15-oic acid (compound 8) presented the best gastroprotective effect, reducing the gastric lesions by 86%, with a similar effect to lansoprazole at 20 mg kg\u22121. The gastroprotective effect of cyperenol, cyperenoic acid methyl ester and the ethylamide and butylamide from cyperenoic acid were in the same range, reducing the gastric lesions by 72\u201377%. Cyperenol and cyperenoic acid methyl ester, however, were more cytotoxic with IC50 (concentration that produces a 50% inhibitory effect) values of 44 and 75, 48 and 75 \u03bcM against AGS cells and fibroblasts, respectively. The best gastroprotective effect with lower cytotoxicity was found for the compound 8, cyperenoic acid and the p-anisidyl derivative 7.<\/jats:p>","DOI":"10.1211\/jpp.58.11.0012","type":"journal-article","created":{"date-parts":[[2006,11,14]],"date-time":"2006-11-14T00:24:43Z","timestamp":1163463883000},"page":"1507-1513","source":"Crossref","is-referenced-by-count":17,"title":["Gastroprotective activity and cytotoxic effect of cyperenoic acid derivatives"],"prefix":"10.1093","volume":"58","author":[{"given":"Mariano","family":"Pertino","sequence":"first","affiliation":[{"name":"Laboratorio de Qu\u00edmica de Productos Naturales, Instituto de Qu\u00edmica de Recursos Naturales, Universidad de Talca , Casilla 747, Talca,","place":["Chile"]}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Jaime A","family":"Rodr\u00edguez","sequence":"additional","affiliation":[{"name":"Depto de Ciencias B\u00e1sicas Biom\u00e9dicas, Facultad de Ciencias de la Salud, Universidad de Talca , Casilla 747, Talca,","place":["Chile"]}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Cristina","family":"Theoduloz","sequence":"additional","affiliation":[{"name":"Depto de Ciencias B\u00e1sicas Biom\u00e9dicas, Facultad de Ciencias de la Salud, Universidad de Talca , Casilla 747, Talca,","place":["Chile"]}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Iv\u00e1n","family":"Razmilic","sequence":"additional","affiliation":[{"name":"Laboratorio de Qu\u00edmica de Productos Naturales, Instituto de Qu\u00edmica de Recursos Naturales, Universidad de Talca , Casilla 747, Talca,","place":["Chile"]}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Guillermo","family":"Schmeda-Hirschmann","sequence":"additional","affiliation":[{"name":"Laboratorio de Qu\u00edmica de Productos Naturales, Instituto de Qu\u00edmica de Recursos Naturales, Universidad de Talca , Casilla 747, Talca,","place":["Chile"]}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"286","published-online":{"date-parts":[[2006,11,1]]},"reference":[{"key":"2024103109344210700_cit1","doi-asserted-by":"crossref","first-page":"128","DOI":"10.1016\/0928-0987(94)90211-9","article-title":"Chemical and biological properties of cyperenal and structurally related sesquiterpenes","volume":"2","author":"Achenbach","year":"1994","journal-title":"Eur. J. Pharm. Sci."},{"key":"2024103109344210700_cit2","doi-asserted-by":"crossref","first-page":"149","DOI":"10.1016\/S0031-9422(96)00777-7","article-title":"Joannesialactone and other compounds from Joannesia princeps","volume":"45","author":"Achenbach","year":"1997","journal-title":"Phytochemistry"},{"key":"2024103109344210700_cit3","volume-title":"Dictionary of Natural Products on CD-ROM","year":"2006"},{"key":"2024103109344210700_cit4","doi-asserted-by":"crossref","first-page":"515","DOI":"10.1055\/s-2002-32570","article-title":"Antiulcerogenic activity of some sesquiterpene lactones isolated from Artemisia annua","volume":"68","author":"Foglio","year":"2002","journal-title":"Planta Med."},{"key":"2024103109344210700_cit5","doi-asserted-by":"crossref","first-page":"803","DOI":"10.1021\/np50070a004","article-title":"The gastric cytoprotective effect of several sesquiterpene lactones","volume":"53","author":"Giordano","year":"1990","journal-title":"J. Nat. Prod."},{"key":"2024103109344210700_cit6","first-page":"201","article-title":"Anti-ulcer drugs of plant origin","volume-title":"Progress in medicinal chemistry.","author":"Lewis","year":"1991"},{"key":"2024103109344210700_cit7","doi-asserted-by":"crossref","first-page":"477","DOI":"10.1016\/S0960-894X(01)00781-8","article-title":"Protective effects of polygodial and related compounds on ethanol-induced gastric mucosal lesions in rat: Structural requirements and mode of action","volume":"12","author":"Matsuda","year":"2002","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"2024103109344210700_cit8","doi-asserted-by":"crossref","first-page":"2447","DOI":"10.1016\/S0040-4039(00)90829-3","article-title":"Terpenoids CXVII: structure of cyperenol and patchoulenol. Two new sesquiterpene alcohol from the oil of Cyperus scariosus","volume":"26","author":"Nerali","year":"1967","journal-title":"Tetrahedron Lett."},{"key":"2024103109344210700_cit9","first-page":"1","volume-title":"Guide to the care and use of experimental animals.","author":"Olfert","year":"1993"},{"key":"2024103109344210700_cit10","doi-asserted-by":"crossref","first-page":"651","DOI":"10.1248\/bpb.26.651","article-title":"Protective effects of polygodial on gastric mucosal lesions induced by necrotizing agents in rats and the possible mechanisms of action","volume":"26","author":"Pongpiriyadacha","year":"2003","journal-title":"Biol. Pharm. Bull."},{"key":"2024103109344210700_cit11","doi-asserted-by":"crossref","first-page":"1038","DOI":"10.1002\/ptr.1784","article-title":"Gastroprotective activity of sesquiterpene derivatives from Fabiana imbricata","volume":"19","author":"Reyes","year":"2005","journal-title":"Phytother. Res."},{"key":"2024103109344210700_cit12","doi-asserted-by":"crossref","first-page":"522","DOI":"10.1055\/s-1999-14008","article-title":"Cytotoxicity of trans-dehydrocrotonin from Croton cajucara (Euphorbiaceae) on V79 cells and rat hepatocytes","volume":"65","author":"Rodr\u00edguez","year":"1999","journal-title":"Planta Med."},{"key":"2024103109344210700_cit13","doi-asserted-by":"crossref","first-page":"2193","DOI":"10.1016\/j.lfs.2005.04.007","article-title":"Gastroprotective and ulcer-healing effect of new solidagenone derivatives in human cell cultures","volume":"77","author":"Rodr\u00edguez","year":"2005","journal-title":"Life Sci."},{"key":"2024103109344210700_cit14","doi-asserted-by":"crossref","first-page":"2503","DOI":"10.1016\/j.lfs.2005.10.018","article-title":"Gastroprotective and ulcer healing effect of ferruginol in mice and rats: assessment of its mechanism of action using in vitro models","volume":"78","author":"Rodr\u00edguez","year":"2006","journal-title":"Life Sci."},{"key":"2024103109344210700_cit15","doi-asserted-by":"crossref","first-page":"61","DOI":"10.1016\/j.jep.2005.06.002","article-title":"Traditional medicine and gastroprotective crude drugs","volume":"100","author":"Schmeda-Hirschmann","year":"2005","journal-title":"J. Ethnopharmacol."},{"key":"2024103109344210700_cit16","doi-asserted-by":"crossref","first-page":"375","DOI":"10.1002\/(SICI)1099-1573(199608)10:5<375::AID-PTR847>3.0.CO;2-#","article-title":"Antiprotozoal activity of Jatrogrossidione from Jatropha grossidentata and Jatrophone from Jatropha isabellii","volume":"10","author":"Schmeda-Hirschmann","year":"1996","journal-title":"Phytother. Res."},{"key":"2024103109344210700_cit17","doi-asserted-by":"crossref","first-page":"271","DOI":"10.1016\/j.jep.2005.04.027","article-title":"Gastroprotective effect of the Mapuche crude drug Araucaria araucana resin and its main constituents","volume":"101","author":"Schmeda-Hirschmann","year":"2005","journal-title":"J. Ethnopharmacol."},{"key":"2024103109344210700_cit18","doi-asserted-by":"crossref","first-page":"511","DOI":"10.1515\/znc-2005-7-801","article-title":"Gastroprotective effect and cytotoxicity of natural and semisynthetic lab-dane diterpenes from Araucaria araucana","volume":"60","author":"Schmeda-Hirschmann","year":"2005","journal-title":"Z. Naturforsch. C"},{"key":"2024103109344210700_cit19","doi-asserted-by":"crossref","first-page":"429","DOI":"10.1016\/j.phrs.2005.06.004","article-title":"Gastroprotective and cytotoxic effect of dehydroabietic acid derivatives","volume":"52","author":"Sep\u00falveda","year":"2005","journal-title":"Pharmacol. Res."},{"key":"2024103109344210700_cit20","doi-asserted-by":"crossref","first-page":"1197","DOI":"10.1016\/0031-9422(88)80302-9","article-title":"Cyperenyl acetate and cyperenal from Cirsium dipsacolepis","volume":"27","author":"Takano","year":"1988","journal-title":"Phytochemistry"}],"container-title":["Journal of Pharmacy and Pharmacology"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1211%2Fjpp.58.11.0012","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/academic.oup.com\/jpp\/article-pdf\/58\/11\/1507\/60254987\/jpp.58.11.0012.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/academic.oup.com\/jpp\/article-pdf\/58\/11\/1507\/60254987\/jpp.58.11.0012.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2024,10,31]],"date-time":"2024-10-31T09:36:59Z","timestamp":1730367419000},"score":1,"resource":{"primary":{"URL":"https:\/\/academic.oup.com\/jpp\/article\/58\/11\/1507\/6147893"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2006,11,1]]},"references-count":20,"journal-issue":{"issue":"11","published-online":{"date-parts":[[2006,11,1]]},"published-print":{"date-parts":[[2006,11,1]]}},"URL":"https:\/\/doi.org\/10.1211\/jpp.58.11.0012","relation":{},"ISSN":["0022-3573","2042-7158"],"issn-type":[{"value":"0022-3573","type":"print"},{"value":"2042-7158","type":"electronic"}],"subject":[],"published-other":{"date-parts":[[2006,11]]},"published":{"date-parts":[[2006,11,1]]}}}