Sesquiterpenoids from Pittocaulon filare.

Abstract

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.

• Authors: Amira Arciniegas, Karina González, Ana-L Pérez-Castorena, Antonio Nieto-Camacho, José-L Villaseñor, Alfonso Romo de Vivar
• Journal: Journal of natural products (J Nat Prod) Vol. 77 Issue 6 Pg. 1304-10 (Jun 27 2014) ISSN: 1520-6025 [Electronic] United States
• PMID: 24842703 (Publication Type: Journal Article)

Chemical References

• 11,12-epoxy-2,8-di(2'-methylbutanoyloxy)-9-(3''-methyl-2''-pentenoyloxy)-10(14)-oplopen-3-one
• 4-acetoxy-11,12-epoxy-2,8-di(2'-methylbutanoyloxy)-9-(3''-methyl-2''-pentenoyloxy)-10(14)-oplopen-3-one
• 4-acetoxy-8-(2'-methylbutanoyloxy)-9-(3''-methyl-2''-pentenoyloxy)-10(14)-oplopen-3-one
• Anti-Inflammatory Agents
• Glucosides
• Sesquiterpenes
• Peroxidase
• Tetradecanoylphorbol Acetate
• Indomethacin

Topics

• Animals
• Anti-Inflammatory Agents (chemistry, pharmacology)
• Asteraceae (chemistry)
• Disease Models, Animal
• Edema (chemically induced, drug therapy)
• Glucosides (adverse effects, therapeutic use)
• Indomethacin (adverse effects, therapeutic use)
• Mexico
• Neutrophil Infiltration (drug effects)
• Neutrophils (metabolism)
• Nuclear Magnetic Resonance, Biomolecular
• Peroxidase (metabolism)
• Sesquiterpenes (chemistry, isolation & purification, pharmacology)
• Stereoisomerism
• Tetradecanoylphorbol Acetate (pharmacology)