title: Seco-taondiol, an unusual meroterpenoid from the Chilean seaweed Stypopodium flabelliforme and its gastroprotective effect in mouse model.
abstract: Ten known meroterpenoids and the new meroterpenoid 7 were isolated from the Chilean seaweed Stypopodium flabelliforme as their acetylated derivatives. Furthermore, the known metabolite taondiol has been isolated for the first time from this species. The molecular structure of the new metabolite was determined by spectroscopic methods based on 1D- and 2D-NMR. Isolation of 7 represents a key step toward a better understanding of the biogenesis of this class of meroterpenoids. Among the meroditerpenoids isolated, stypodiol, isoepitaondiol, epitaondiol and sargaol exhibited gastroprotective activity on the HCl/Ethanol-induced gastric lesions model in mice. Regarding the mode of gastroprotective action, the activity of epitaondiol was reversed significantly when animals were pretreated with indomethacin, N-ethylmaleimide and N-nitro-l-arginine methyl ester (L-NAME) suggesting that prostaglandins, sulfhydryl groups and nitric oxide are involved in their mode of gastroprotective action. In the case of sargaol the gastroprotective activity was attenuated with indomethacin and N-ethylmaleimide, which suggests that prostaglandins and sulfhydryl groups are also involved in the mode of action using this model.
authors.affiliation: Departamento de Química, Facultad de Ciencias, Universidad de Chile, Santiago 8320000, Chile. areche@uchile.cl.
authors.forename: Carlos
authors.initials: C
authors.lastname: Areche
authors.affiliation: Facultad de Ciencias de la Salud, Universidad Arturo Prat, Casilla 121, Iquique 1100000, Chile. juliob@unap.cl.
authors.forename: Julio
authors.initials: J
authors.lastname: Benites
authors.affiliation: Escuela de Tecnología Médica, Facultad de Medicina, Universidad Andrés Bello, Santiago 8370186, Chile. alberto.cornejo@unab.cl.
authors.forename: Alberto
authors.initials: A
authors.lastname: Cornejo
authors.affiliation: Facultad de Ciencias de la Salud, Universidad Autónoma de Chile, Santiago 8910132, Chile. limarui_hinca@yahoo.com.
authors.forename: Lina M
authors.initials: LM
authors.lastname: Ruiz
authors.affiliation: Facultad de Ciencias Naturales y Matemáticas, Universidad de Ibagué, Carrera 22 Calle 67, Ibagué 730001, Colombia. jose.garcia@unibague.edu.co.
authors.forename: Olimpo
authors.initials: O
authors.lastname: García-Beltrán
authors.affiliation: Laboratorio de Productos Naturales, Departamento de Química, Facultad de Ciencias Básicas, Universidad de Antofagasta, Antofagasta 1240000, Chile. mario.simirgiotis@uantof.cl.
authors.forename: Mario J
authors.initials: MJ
authors.lastname: Simirgiotis
authors.affiliation: Departmento de Ciencias Químicas, Facultad de Ciencias Exactas, Universidad Andrés Bello, Quillota 980, Viña del Mar 2520000, Chile. bsepulveda@uc.cl.
authors.forename: Beatriz
authors.initials: B
authors.lastname: Sepúlveda
mesh_terms: D000107:Acetylation; D000818:Animals; D000897:Anti-Ulcer Agents / Q000009:adverse effects / Q000737:chemistry / Q000302:isolation & purification* / Q000627:therapeutic use; D002460:Cell Line; D002677:Chile; D004195:Disease Models, Animal; D004224:Diterpenes / Q000009:adverse effects / Q000737:chemistry / Q000302:isolation & purification* / Q000627:therapeutic use; D055808:Drug Discovery; D005753:Gastric Mucosa / Q000187:drug effects; D006801:Humans; D051379:Mice; D015394:Molecular Structure; D010140:Pacific Ocean; D000459:Phaeophyceae / Q000737:chemistry* / Q000254:growth & development; D011114:Polynesia; D020011:Protective Agents / Q000009:adverse effects / Q000737:chemistry / Q000302:isolation & purification / Q000627:therapeutic use; D011897:Random Allocation; D012624:Seaweed / Q000737:chemistry* / Q000254:growth & development; D013237:Stereoisomerism; D013276:Stomach Ulcer / Q000517:prevention & control*; D013729:Terpenes / Q000009:adverse effects / Q000737:chemistry / Q000302:isolation & purification / Q000627:therapeutic use
chemical_list: D000897:Anti-Ulcer Agents; D004224:Diterpenes; D020011:Protective Agents; D013729:Terpenes; C561788:sargaol; C009378:taondiol; C094446:epitaondiol
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