La actividad antibacteriana in vitro del auraptene y de cuatro ácidos preniloxycinámicos y benzoicos ha sido evaluada sobre un grupo de tres distintas cepas bacterianas. Todos los compuestos mostraron ser activos como agentes inhibitorios del crecimiento del Staphylococcus Aureus

CURINI, Massimo

EPIFANO, Francesco

GENOVESE, Salvatore

MESSINA, Federica

English

Boletín Latinoamericano y del Caribe de Plantas Medicinales y Aromáticas

  
 
© 2012 Boletín Latinoamericano y del Caribe de Plantas Medicinales y Aromáticas 11 (1): 74 - 76 
 ISSN 0717 7917 
www.blacpma.usach.cl 
 
Artículo Original | Original Article 
74 
 
 
Antibacterial properties of auraptene and oxyprenylated naturally 
occurring benzoic and cinnamic acids 
 
 [Propiedades antibacterianas del auraptene y acidos benzoicos y cinámicos oxi-prenilados naturales] 
 
 
Massimo CURINI1, Francesco EPIFANO2, Federica MESSINA1 & Salvatore GENOVESE2 
 
 
1Dipartimento di Chimica e Tecnologia del Farmaco, Sezione di Chimica Organica, Università degli Studi di Perugia, Perugia, Italy.  
2Dipartimento di Scienze del Farmaco, Università “G. D’Annunzio” Chieti-Pescara, Chieti Scalo, Italy 
*Contactos | Contacts: Massimo CURINI - E-mail address: curmax@unipg.it 
 
 
 
 
 
 
Abstract  
The in vitro anti-bacterial activity of auraptene and four prenyloxycinnamic and benzoic acids was evaluated against a panel of three bacterial strain. All 
compounds were shown to be active as inhibitory agents of the growth of Staphylococcus aureus. 
 
 
Keywords: anti-bacterial activity, auraptene, prenyloxycinnamic acids, prenyloxyphenylpropanoids, Staphylococcus aureus. 
 
 
 
Resumen 
La actividad antibacteriana in vitro del auraptene y de cuatro ácidos preniloxycinámicos y benzoicos ha sido evaluada sobre un grupo de tres distintas cepas 
bacterianas. Todos los compuestos mostraron ser activos como agentes inhibitorios del crecimiento del Staphylococcus Aureus. 
 
 
Palabras Claves: actividad antibacteriana, auraptene, ácidos preniloxycinámicos, Staphylococcus aureus 
 
 
 
 
 
 
  
Recibido | Received: October 20, 2011. 
Aceptado en versión corregida | Accepted in revised form: December 19, 2011 
Publicado en línea | Published online: January 30, 2012. 
Este artículo puede ser citado como / This article must be cited as: Massimo Curini, Francesco Epifano, Federica Messina, Salvatore Genovese.  2012. Antibacterial properties 
of auraptene and oxyprenylated naturally occurring benzoic and cinnamic acids  Bol Latinoam Caribe Plant Med Aromat 11(1): 74 - 76.  
Curini et al. Anti-bacterial activity of prenyloxyphenylpropanoids  
 
Boletin Latinoamericano y del Caribe de Plantas Medicinales y Aromáticas/75 
 
INTRODUCTION 
Oxyprenylated natural products, such as 
isopentenyloxy- (C5), geranyloxy- (C10), and 
farnesyloxy- (C15) related compounds, represent a 
family of secondary metabolites that were considered 
for years to be merely biosynthetic intermediates of 
the more widespread C-prenylated derivatives. These 
secondary metabolites have been recognized in the last 
two decades as interesting and valuable biologically 
active phytochemicals. Approximately 300 
compounds have been isolated and structurally 
characterized from plants, primarily from the families 
Rutaceae, Compositae, Guttiferae, and Leguminosae, 
comprising several edible vegetables and fruits. The 
phytochemistry and pharmacology of 
prenyloxyphenylpropanoids was recently reviewed 
(Epifano et al., 2007).
 
Among these auraptene 1 
(Genovese and Epifano, 2011), boropinic acid 2 
(Curini et al., 2008), and 4'-geranyloxyferulic acid 3
 
(Curini et al., 2006) were shown to exert significant 
and appreciable biological effects as anti-cancer, anti-
protozoal, anti-fungal, anti-inflammatory, and anti-
oxidant agents. Aim of the current work was to study 
the anti-bacterial properties of these secondary 
metabolites together with those of two 
isopentenyloxycinnamic acids, namely valencic acid 4, 
previously isolated from plants of the genus Citrus, 
and 4'-isopentenyloxyvanillic acid 5, extracted from 
plants belonging to the genus Tricocholea (Epifano et 
al., 2007). 
 
 
 
 
 
 
 
 
 
 
 
 
 
MATERIALS AND METHODS 
Both for the chemical synthesis of compounds 1-5 
(Genovese et al., 2009) and for the in vitro anti-
bacterial growth assays (agar diffusion method using 
Muellener-Hinton agar) (Richardson et al., 1968) the 
same general procedures as reported previously were 
followed. Analytical data (m.p., IR, 1H, 13C NMR, 
elemental analysis) for 1-5 were in full agreement with 
those previously reported for the same compounds 
(Genovese et al., 2009). The three bacterial strains 
used were Staphylococcus aureus ATCC 29213, 
Escherichia coli ATCC 700926, and Streptococcus 
mutans ATCC 25175. All phytochemicals were were 
dissolved in DMSO and tested in the concentration 
range 0.5 – 62.5 g/mL. 100 l of 18 h bacterial 
cultures were used to spread a lawn on the agar. The 
cultures were adjusted to 10
5
 CFU/ml using 
McFarland standard and solutions of each compound 
at the indicated concentration was added to each 
culture. The plates were left 30 min at room 
temperature for the diffusion of solutions containing 
compounds 1-5 and incubated at 37 °C for 18 h. The 
zones of inhibition were measured by a ruler and each 
experiment was repeated three times. Chloramphenicol 
was used as reference drug. 
 
RESULTS AND DISCUSSION 
Results of the inhibition of growth of the three 
bacterial strains under investigation, expresses as the 
minimum inhibitory concentration (MIC), are reported 
in the Table 1. 
The five compounds under investigation 
exhibited a different range of activity towards the three 
microrganisms. Streptococcus mutans was the less 
sensible and all products can be considered virtually 
inactive. 4'-Geranyloxyferulic acid, valencic acid, and 
'-isopentenyloxyvanillic acid were only slightly active 
on Escherichia coli, while auraptene and boropinic 
acid were found by far less potent than these three 
products. The most interesting results were obtained 
on the growth of Staphylococcus aureus. All 
compounds exhibited a significant activity with MIC 
ranging from 4.1 to 6.9 g/mL. These data are of 
interest considering that S. aureus is nowadays well 
recognized as one of the most dangerous bacterium 
able to lead to severe syndromes in humans as well as 
to resist to the most part of chemotherapeutics 
currently at disposition. In particular the phenomenon 
of resistance by S. aureus is growing all over the 
world (Rogers et al. 2011). 
 
CONCLUSIONS 
In this manuscript we studied the in vitro anti-bacterial 
properties and disclose a novel potential application of 
auraptene and oxyprenylated benzoic and cinnamic 
acids. The results obtained in the case of S. aureus will 
be further and better characterized in the next future  
O OO
1
R1
R2
OR3
2 R1 = CH=CH-COOH, R2 = OCH3, R
3 = H
3 R1 = CH=CH-COOH, R2 = OCH3, R
3 = isopentenyl
4 R1 = COOH, R2 = R3 = H
5 R1 = COOH, R2 = OCH3, R
3 = H 
Curini et al. Anti-bacterial activity of prenyloxyphenylpropanoids  
 
Boletin Latinoamericano y del Caribe de Plantas Medicinales y Aromáticas/76 
 
 
Table 1 
Antibacterial activity of selected prenyloxyphenylpropanoids 
 
 MIC ( g/mL) 
Compound Escherichia coli Staphylococcus aureus Streptococcus mutans 
1 30 6.9 > 62.5 
2 30 4.3 38 
3 10 5.3 23 
4 10 4.1 41 
5 10 5.3 23 
Chloramphenicol 5 5 15 
 
but, although preliminary, the data reported in this 
manuscript could be useful to identify novel 
therapeutic weapons against this extremely dangerous 
bacterium and prenyloxyphenylpropanoids as novel 
lead anti-bacterial compounds. In the mean time 
studies to evaluate the toxicological profile of these 
secondary metabolites are ongoing.  
 
REFERENCES 
Curini M, Genovese S, Menghini L, Marcotullio MC, 
Epifano F 2008. Phytochemistry and 
Pharmacology of Boronia pinnata Sm. Nat 
Prod Commun 3: 2145 - 2150. 
Curini M, Epifano F, Genovese S, Marcotullio MC 
Menghini L 2006. 3-(4'-Geranyloxy-3'-
Methoxyphenyl)-2-trans Propenoic Acid: a 
Novel Promising Cancer Chemopreventive 
Agent. Anticanc Agents  Med Chem 6: 571 - 
577. 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
Epifano F, Genovese S, Menghini L, Curini M. 2007. 
Chemistry and pharmacology of 
oxyprenylated secondary plant metabolites 
(Review). Phytochemistry 68: 939 - 953. 
Genovese S, Epifano F 2011. Auraptene: a Natural 
Biologically Active Compound with Multiple 
Targets. Curr Drug Targets 12: 381 - 386. 
Genovese S, Epifano F, Curini M, Dudra-Jastrzebska 
M, Luszczki JJ 2009. Prenyloxyphenyl-
propanoids as a Novel Class of Anticonvulsive 
Agents. Bioorg Med Chem Lett 19: 5419 - 
5422. 
Richardson H, Emslie-Smith AH, Senior BW 1968. 
Agar Diffusion Method for the Assay of 
Colicins. Appl Microbiol 16: 1468 - 1474. 
Rogers BA, Aminzadeh Z, Hayashi Y, Paterson DL 
2011. Country-to-country transfer of patients 
and the risk of multi-resistant bacterial 
infection. Clin Infect Dis 53: 49 - 56. 


Propiedades antibacterianas del auraptene y acidos benzoicos y cinámicos oxi-prenilados naturales

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Propiedades antibacterianas del auraptene y acidos benzoicos y cinámicos oxi-prenilados naturales

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