{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,18]],"date-time":"2025-10-18T10:34:41Z","timestamp":1760783681272,"version":"3.37.3"},"reference-count":32,"publisher":"Oxford University Press (OUP)","issue":"8","license":[{"start":{"date-parts":[[2013,8,1]],"date-time":"2013-08-01T00:00:00Z","timestamp":1375315200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/academic.oup.com\/journals\/pages\/open_access\/funder_policies\/chorus\/standard_publication_model"}],"funder":[{"name":"FONDECYT INICIACION","award":["11110241"],"award-info":[{"award-number":["11110241"]}]},{"DOI":"10.13039\/501100002850","name":"FONDECYT","doi-asserted-by":"publisher","award":["11090120"],"award-info":[{"award-number":["11090120"]}],"id":[{"id":"10.13039\/501100002850","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100013327","name":"ICM","doi-asserted-by":"publisher","award":["P10-035-F"],"award-info":[{"award-number":["P10-035-F"]}],"id":[{"id":"10.13039\/100013327","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2013,8,1]]},"abstract":"<jats:title>Abstract<\/jats:title>\n               <jats:sec>\n                  <jats:title>Objectives<\/jats:title>\n                  <jats:p>The chemical study of a dichloromethane extract from Azorella compacta was directed to the isolation of characteristic mulinane and azorellane diterpenoids in order to determine their gastroprotective activity.<\/jats:p>\n               <\/jats:sec>\n               <jats:sec>\n                  <jats:title>Methods<\/jats:title>\n                  <jats:p>Usual chromatographic techniques on the extract led to the isolation of 12 compounds, which were identified by their spectroscopic properties. The HCl\/ethanol-induced gastric lesions model in mice was used to determine the gastroprotective activity.<\/jats:p>\n               <\/jats:sec>\n               <jats:sec>\n                  <jats:title>Key findings<\/jats:title>\n                  <jats:p>The new diterpenoids, 13\u03b2-hydroxymulinane (1), mulin-11,13-dien-20-ol (2), 13\u03b1-methoxyazorellanol (3) and mulin-11,13-dien-18-acetoxy-16,20-dioic acid (12) were isolated from A. compacta. The known diterpenoids mulin-11,13-dien-20-oic acid (4), 13\u03b1-hydroxyazorellane (5), 13\u03b2-hydroxyazorellane (6), mulinic acid (7), mulinolic acid (8) and azorellanol (9), and the aromatic compounds 5,7-dihydroxychromone (10) and isoflavonoid biochanin A (11), were also obtained from the extract. Compounds 6, 9 and 12 at 20 mg\/kg reduced gastric lesions by 69%, 71% and 73%, respectively, being statistically similar to lansoprazole at the same dose.<\/jats:p>\n               <\/jats:sec>\n               <jats:sec>\n                  <jats:title>Conclusions<\/jats:title>\n                  <jats:p>The results corroborate the intraspecific chemical variations detected previously in specimens of A. compacta collected at different Chilean latitudes. A high concentration of azorellanol (9) could account in part for some of the therapeutic properties attributed to this species, in particular in ulcer treatment. Most of the mulinane and azorellane diterpenoids isolated in this study showed relevant gastroprotective activity at a low dose in the bioassay.<\/jats:p>\n               <\/jats:sec>","DOI":"10.1111\/jphp.12083","type":"journal-article","created":{"date-parts":[[2013,5,22]],"date-time":"2013-05-22T02:23:41Z","timestamp":1369189421000},"page":"1231-1238","source":"Crossref","is-referenced-by-count":21,"title":["Further mulinane diterpenoids from <i>Azorella compacta<\/i>"],"prefix":"10.1093","volume":"65","author":[{"given":"Carlos","family":"Areche","sequence":"first","affiliation":[{"name":"Departamento de Qu\u00edmica, Facultad de Ciencias, Universidad de Chile ,","place":["Chile"]}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Francisca","family":"Rojas-Alvarez","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica, Facultad de Ciencias, Universidad de Chile ,","place":["Chile"]}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Carolina","family":"Campos-Briones","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica, Facultad de Ciencias, Universidad de Chile ,","place":["Chile"]}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Carlos","family":"Lima","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica, Facultad de Ciencias, Universidad de Chile ,","place":["Chile"]}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Edwin G","family":"P\u00e9rez","sequence":"additional","affiliation":[{"name":"Facultad de Qu\u00edmica, Pontificia Universidad Cat\u00f3lica de Chile , Santiago,","place":["Chile"]}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Beatriz","family":"Sep\u00falveda","sequence":"additional","affiliation":[{"name":"Departmento de Qu\u00edmica, Universidad Andr\u00e9s Bello , Vi\u00f1a del Mar,","place":["Chile"]}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"286","published-online":{"date-parts":[[2013,8,1]]},"reference":[{"key":"2024103109171391300_jphp12083-cit-0001","doi-asserted-by":"crossref","first-page":"649","DOI":"10.1016\/S0031-9422(96)00603-6","article-title":"Diterpenoids from Azorella compacta","volume":"44","author":"Loyola","year":"1997","journal-title":"Phytochemistry"},{"key":"2024103109171391300_jphp12083-cit-0002","doi-asserted-by":"crossref","first-page":"1465","DOI":"10.1016\/S0031-9422(97)00178-7","article-title":"Mulinol, a diterpenoids from Azorella compacta","volume":"45","author":"Loyola","year":"1997","journal-title":"Phytochemistry"},{"key":"2024103109171391300_jphp12083-cit-0003","doi-asserted-by":"crossref","first-page":"1091","DOI":"10.1016\/S0031-9422(97)01062-5","article-title":"11,12Epoxy-mulin-13-en-20-oic acid, a diterpenoid from Azorella compacta","volume":"49","author":"Loyola","year":"1998","journal-title":"Phytochemistry"},{"key":"2024103109171391300_jphp12083-cit-0004","doi-asserted-by":"crossref","first-page":"15533","DOI":"10.1016\/S0040-4020(98)01016-3","article-title":"Azorellanol: a diterpenoids with a new carbon skeleton from Azorella compacta","volume":"54","author":"Loyola","year":"1998","journal-title":"Tetrahedron"},{"key":"2024103109171391300_jphp12083-cit-0005","doi-asserted-by":"crossref","first-page":"413","DOI":"10.1590\/S0074-02762003000300022","article-title":"Diterpenoids from Azorella compacta (Umbelliferae) active on Trypanosoma cruzi","volume":"98","author":"Araya","year":"2003","journal-title":"Mem Inst Oswaldo Cruz"},{"key":"2024103109171391300_jphp12083-cit-0006","doi-asserted-by":"crossref","first-page":"713","DOI":"10.1002\/ptr.1740","article-title":"Experimental antihyperglycemic affect of diterpenoids of llareta Azorella compacta (Umbelliferae) Phil in rat","volume":"19","author":"Fuentes","year":"2005","journal-title":"Phytother Res"},{"key":"2024103109171391300_jphp12083-cit-0007","doi-asserted-by":"crossref","first-page":"1931","DOI":"10.1016\/j.phytochem.2004.06.011","article-title":"Mulinane-type diterpenoids from Azorella compacta display antiplasmodial activity","volume":"65","author":"Loyola","year":"2004","journal-title":"Phytochemistry"},{"key":"2024103109171391300_jphp12083-cit-0008","doi-asserted-by":"crossref","first-page":"1319","DOI":"10.1021\/np990134u","article-title":"Antibacterial diterpenoid acids from Azorella compacta","volume":"62","author":"W\u00e4chter","year":"1999","journal-title":"J Nat Prod"},{"key":"2024103109171391300_jphp12083-cit-0009","doi-asserted-by":"crossref","first-page":"177","DOI":"10.1016\/S0031-9422(00)00380-0","article-title":"Diterpenoids from Azorella yareta and their trichomonicidal activities","volume":"56","author":"Loyola","year":"2001","journal-title":"Phytochemistry"},{"key":"2024103109171391300_jphp12083-cit-0010","doi-asserted-by":"crossref","first-page":"5413","DOI":"10.1016\/S0040-4020(01)87848-0","article-title":"Mulinic and isomulinic acids. 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