Planta Med 2009; 75(1): 18-23
DOI: 10.1055/s-0028-1088343
Pharmacology
Original Paper
© Georg Thieme Verlag KG Stuttgart · New York

Anti-Inflammatory Activity of Berenjenol and Related Compounds

Silvia Aquila1 , 2 , Benjamin Rojano3 , María C. Recio1 , Rosa M. Giner1 , Guillermo R. Schinella4 , Silvia L. Debenedetti2 , Jairo Saez5 , José Luis Ríos1
  • 1Departament de Farmacología, Facultat de Farmàcia, Universitat de València, Spain
  • 2Departamento de Ciencias Biológicas, Facultad de Ciencias Exactas, Universidad Nacional de La Plata, La Plata, Argentina
  • 3Laboratorio Ciencia de los Alimentos, Escuela de Química, Universidad Nacional de Colombia, Sede Medellín, Medellín, Colombia
  • 4Cátedra de Farmacología Básica, Facultad de Ciencias Médicas, Universidad Nacional de La Plata, CIC Provincia de Buenos Aires, La Plata, Argentina
  • 5Instituto de Química, Química de Plantas Colombianas, Universidad deAntioquia, Medellín, Colombia
Further Information

Publication History

Received: June 2, 2008 Revised: September 8, 2008

Accepted: September 17, 2008

Publication Date:
18 November 2008 (online)

Abstract

Berenjenol (1), isolated from Oxandra cf. xylopioides (Annonaceae), was tested on two different experimental models of inflammation. The compound showed anti-inflammatory activity in the test of acute mouse ear edema induced by TPA (54 % inhibition, 1 μmol/ear) as well as in the test of subchronic inflammation induced by repeated application of TPA (57 % inhibition, 7 × 1 μmol/ear). Moreover, while it reduced the expression of both COX-2 (65 % inhibition at 50 μM) and iNOS (80 % inhibition at 50 μM), it was not active against TNF-α and IL-1β in murine macrophages (RAW 264.7) stimulated with LPS. Structural modification of 1 gave two derivatives, berenjenol acetate (2) and 3-oxo-berenjenol (3). Of these, the latter had a high degree of activity in the acute test (66 % inhibition, 1.1 μmol/ear), whereas the former showed no enhanced pharmacological properties. Interestingly, the original compound exhibited higher activity than either of its derivatives in the subchronic model. We thus concluded that whereas 3-oxidation of 1 (compound 3), but not 3-acetylation (2), increases the activity in the acute model of inflammation, structural modification of 1 does not enhance the compound’s effects in the subchronic model.

Abbreviations

COX:cyclooxygenase

DMSO:dimethyl sulfoxide

FBS:fetal bovine serum

IL-1β:interleukin-1β

LPS:lipopolysaccharide

MTT:3-(4,5-dimethylthiazolyl)-2,5-diphenyl-tetrazolium bromide

NOS:nitric oxide synthase

PBS:phosphate-buffered saline

PKC:protein kinase C

TNF-α:tumor necrosis factor-α

TPA:12-O-tetradecanoylphorbol 13-acetate

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Prof. José-Luis Ríos

Departament de Farmacología

Facultat de Farmàcia

Universitat de València

Av. Vicent Andrés Estellés s/n

46100 Burjassot

Valencia

Spain

Phone: +34-963-544-973

Fax: +34-963-544-498

Email: riosjl@uv.es