Antiinflammatory activity of cinnamic acid esters

Article abstract of DOI:10.3390/50300547

The cinnamate esters of 3-p-menthanol (trivial name, menthol) (1) and 4(8)-p-menthen-3-ol (trivial name, pulegol) (2) were prepared and their anti-inflammatory activity was measured. Some of the monoterpenoid esters displayed interesting anti-inflammatory

Full text of DOI:10.3390/50300547

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Molecules 2000, 5
Antiinflammatory Activity of Cinnamic Acid Esters
M. E. Godoy, A. Rotelli, L. Pelzer and C. E.Tonn
Química Orgánica. INTEQUI-CONICET. UNSL. Chacabuco y Pedernera (5700). San Luis, Argentina
E-mail: egodoy@unsl.edu.ar
Abstract: The cinnamate esters of 3-p-menthanol (trivial name, menthol) (1) and 4(8)-p-
menthen-3-ol (trivial name, pulegol) (2) were prepared and their anti-inflammatory activity
was measured. Some of the monoterpenoid esters displayed interesting anti-inflammatory
activity.
O
Introduction
O
Natural phenylpropanes, represented by the bornyl esters of
1
coumaric, caffeic y ferulic acid have shown effectiveness as
antiinflammatory drugs [1,2]. Bearing in mind these precedents, in this
O
work we report the results of our tests, by the carregeenan induced-
O
edema test method, of the antiinflammatory activity of some cinnamic
acid esters prepared in the laboratory.
2
Experimental Part
Ester Preparation
Pulegyl and menthyl cinnamates were obtained following the previously describde nmethodology
[
3]. The corresponding acid chloride was prepared under an inert atmosphere using thionyl chloride in
refluxing anhydrous benzene. The acid chloride was added to the monoterpene alcohol dissolved in dry
benzene containing a few Mg shavings and then refluxed for 8 hrs [4]. The esters were identified by
1
13
their physical constants, H and C NMR and MS. Pulegol was prepared from pulegone by NaBH
reduction in the presence of CeCl3.
4
Carrageenan Test
Acute mouse paw edema was induced by administration of 3.5% carrageenan. Previously the ani-
mals had received an interperitoneal dose of 75 mg/kg of the compounds under study, while the refer-
ence animal received 80 mg/kg of phenylbutazone. The volumes of the mice paws were compared 1, 3,

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Molecules 2000, 5
, and 7 hrs after administratoion of carregeenan to measure the anti-inflammatory effect [5,6].
Results and Discussion
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All the compounds tested displayed interesting activity although the effects of pulegyl cinnamate
were particularly noteworthy (Table 1).
Table 1. Carrageenan Test.
Percentages of Inhibition of Acute Inflam-
Products
mation
3 hrs
1
hr
5 hrs
73(i)
52(d)
45(e)
56(h)
32
7 hrs
69(i)
27
Phenylbutazone
Cinnamic acid
Pulegol
69(i)
58(b)
54(g)
49(a)
48(f)
73(i)
45(c)
54(d)
62(j)
49(j)
47(g)
50(b)
47(a)
Pulegyl cinnamate
Menthyl cinnamate
(
(
a) p<0.002; (b) p<0.0002; (c) P<0.0007; (d) p<0.0001; (e) p<0.003;
f) p< 0.008; (g) p<0.001; (h) p<0.0003; (i) p<0.000001; (j) p<0.00001.
Acknowledgements: This work was done with funding from CONICET and UNSL. We thanks Dr. P.C.
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Rossomando and Lic. E. García for the H and C NMR spectra.
References and Notes
1.
2.
3.
Zschocke, S.; Lehner, M.; Bauer, R. Planta Medica 1997, 63, 203.
Maldonado, E; Ramírez Apan, M. T.; Pérez-Castorena, A. L. Planta Medica 1998, 64, 660.
Faraoni, M.B. en Tesis de Magister (Univ.Nac.del Sur). «Nuevo método para la síntesis de com-
puestos organoestánnicos en átomo de estaño quiral» (1997).
4.
5.
6.
Gastaminza, A. E.; Ferracutti, N. N. An. Asoc. Quím. Argent. 1983, 71, 587.
Sugishita, E.; Amagaya, S.; Ogihara, Y. J. Pharmacobio-Dyn. 1981, 4, 565.
Favier, L.S.; Tonn, C.E.; Guerreiro, E.; Rotelli, E.; Pelzer, L. Planta Medica 1998, 64, 657.