Gastroprotective activity of sesquiterpene derivatives from Fabiana imbricata.
An infusion or decoction of the aerial parts of Fabiana imbricata (Solanaceae) is used in traditional medicine in Chile and Argentina as a digestive and diuretic agent. The main sesquiterpene of the plant was identified as 11-hydroxy-4-amorphen-15-oic acid. At doses of 25, 50 and 100 mg/kg, the compound showed a dose-dependent gastroprotective effect in HCl/EtOH-induced gastric lesions in mice reducing the lesions by 68% at 100 mg/kg. Seven derivatives of the terpene were prepared and their gastroprotective effect was assessed in HCl/EtOH-induced gastric lesions in mice. The cytotoxicity of the products was evaluated in fibroblasts and AGS cells. At 100 mg/kg, 11-hydroxy-4-amorphen-15-p-toluidinamide presented the best gastroprotective effect reducing the gastric lesions by 80%, showing a similar effect to lansoprazole at 20 mg/kg. The compound, however, presented higher cytotoxicity than other derivatives with the IC50 ranging between 110 and 145 microm in AGS cells and fibroblasts, respectively. Most compounds proved to be non-toxic showing cytotoxicity values higher than 1000 microm. The spectroscopic data of six 11-hydroxy-4-amorphen-15-oic acid derivatives are presented here for the first time.
Reyes
Maribel
M
Laboratorio de Productos Naturales, Instituto de Química de Recursos Naturales, Universidad de Talca, Casilla 747, Talca, Chile.
Schmeda-Hirschmann
Guillermo
G
Razmilic
Iván
I
Theoduloz
Cristina
C
Yáñez
Tania
T
Rodríguez
Jaime A
JA
D000818:Animals; D000897:Anti-Ulcer Agents / Q000737:chemistry / Q000627:therapeutic use* / Q000633:toxicity; D002478:Cells, Cultured; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D015394:Molecular Structure; D008517:Phytotherapy; D035261:Plant Components, Aerial; D010936:Plant Extracts / Q000737:chemistry / Q000627:therapeutic use / Q000633:toxicity; D012717:Sesquiterpenes / Q000737:chemistry / Q000494:pharmacology / Q000627:therapeutic use* / Q000633:toxicity; D019657:Solanaceae / Q000737:chemistry*; D013276:Stomach Ulcer / Q000188:drug therapy*
C508699:11-hydroxy-4-amorphen-15-oic acid; D000897:Anti-Ulcer Agents; D010936:Plant Extracts; D012717:Sesquiterpenes