Sesquiterpenoids from Pittocaulon filare.
The phytochemical study of Pittocaulon filare afforded three oplopanes (1-3), a eudesmane (6), and three oplopane glucosides (7-9), one of them reported as its acetyl derivative (7a), together with several known compounds. The structures of the compounds were elucidated by spectroscopic analysis and chemical reactions. The anti-inflammatory activity of compounds 1-5 was determined using the 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced ear edema model, and the effect of compounds 1-4 on the recruitment of neutrophils was evaluated using the myeloperoxidase test. Compounds 1 and 2 were the more active anti-inflammatory agents, with lower ID50 values (0.17 and 0.18 μmol/ear, respectively) than indomethacin (0.24 μmol/ear), but they had a lesser effect on the inhibition of neutrophil infiltration than both indomethacin and compound 3, indicating that the tested compounds do not have the same ability to inhibit edema and to prevent cell infiltration.
Instituto de Química, Universidad Nacional Autónoma de México , Circuito Exterior, Ciudad Universitaria, Coyoacán 04510, D.F., México.
Amira
A
Arciniegas
Karina
K
González
Ana-L
AL
Pérez-Castorena
Antonio
A
Nieto-Camacho
José-L
JL
Villaseñor
Alfonso
A
Romo de Vivar
D000818:Animals; D000893:Anti-Inflammatory Agents / Q000737:chemistry / Q000494:pharmacology; D019659:Asteraceae / Q000737:chemistry*; D004195:Disease Models, Animal; D004487:Edema / Q000139:chemically induced / Q000188:drug therapy; D005960:Glucosides / Q000009:adverse effects / Q000627:therapeutic use; D007213:Indomethacin / Q000009:adverse effects / Q000627:therapeutic use; D008800:Mexico; D020556:Neutrophil Infiltration / Q000187:drug effects; D009504:Neutrophils / Q000378:metabolism; D019906:Nuclear Magnetic Resonance, Biomolecular; D009195:Peroxidase / Q000378:metabolism; D012717:Sesquiterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D013237:Stereoisomerism; D013755:Tetradecanoylphorbol Acetate / Q000494:pharmacology
C000591074:11,12-epoxy-2,8-di(2'-methylbutanoyloxy)-9-(3''-methyl-2''-pentenoyloxy)-10(14)-oplopen-3-one; C000591073:4-acetoxy-11,12-epoxy-2,8-di(2'-methylbutanoyloxy)-9-(3''-methyl-2''-pentenoyloxy)-10(14)-oplopen-3-one; C000591072:4-acetoxy-8-(2'-methylbutanoyloxy)-9-(3''-methyl-2''-pentenoyloxy)-10(14)-oplopen-3-one; D000893:Anti-Inflammatory Agents; D005960:Glucosides; D012717:Sesquiterpenes; D009195:Peroxidase; D013755:Tetradecanoylphorbol Acetate; D007213:Indomethacin