Antifeedant and Phytotoxic Activity of the Sesquiterpene
p-Benzoquinone Perezone and Some of its Derivatives
Eleuterio Burgueño-Tapia
&
Lucia Castillo
&
Azucena González-Coloma
&
Pedro Joseph-Nathan
Received: 30 January 2008 /Revised: 15 April 2008 /Accepted: 2 May 2008 /Published online: 5 June 2008
#
Springer Science + Business Media, LLC 2008
Abstract The sesquiterpene p-benzoquinone perezone (1),
isolated from Perezia adnata var.alamani(Asteraceae), and
its non-natural derivatives isoperezone (2), dihydroperezone
(3), dihydroisoperezone (4), and anilidoperezone (5) were
tested as antifeedants against the herbivorous insects
Spodoptera littoralis, Leptinotarsa decemlineata,andMyzus
persicae.Compounds1–5 exhibited strong antifeedant
activity against L. decemlineata and M. persicae, and elicited
a low response by S. littoralis. Antifeedant activity on L.
decemlineata and M. persicae increased when the hydroxyl
group at C-3 in perezone (1) was changed to C-6 to give
isoperezone (2). The same effect was found with hydroge-
nation of the double bond of the alkyl chain of (1) to yield
dihydroperezone (3). In contrast, hydrogenation of this
double bond in isoperezone (2) to give dihydroisoperezone
(4) led to a reduction in antifeedant activity. Determination of
the phytotoxic activity of 1–5 revealed that 3 had a
significant inhibition effect on Lactuca sativa radicle length
growth.
Keywords Perezone
.
Isoperezone
.
Antifeedant
.
Phytotoxicity
Introduction
Natural quinones and some derivatives have attracted
attention as insecticidal (Xu et al. 2003), antifeedant
(Marimoto et al. 2002; Wellsow et al. 2006), and phytotoxic
compounds (Hejl et al. 1993; Barbosa et al. 2001; Lima et
al. 2003;, Hejl and Koster 2004). To date, however, only a
small group of sesquiterpenoid quinones has been tested
with respect to these biological activities (Motti et al. 2007;
Burgueño-Tapia et al. 2008). Perezone (1), a sesquiterpe-
noid p-benzoquinone described by Río de la Loza (1852),
was the earliest natural product isolated in crystalline form
discovered in the New World (Fig. 1). It originally was
isolated from roots of Perezia adnata var. alamani
(Asteraceae), popularly known as ‘raiz del pipitzahuac’.
Its structure was characterized (Archer and Thomson 1965;
Bates et al. 1965; Wagner et al. 1965; Walls et al. 1965b)
113 years after its discovery, as a direct consequence of the
structural elucidation of α- and β-pipitzol (Walls et al.
1965a), obtained by heating 1. Ever since its original
isolation more than 155 years ago, perezone has been the
subject of extensive chemical studies (Joseph-Nathan and
Santillan 1989; Roura-Pérez et al. 2007), including its
rearrangement to isoperezone (2) (Rodríguez-Hernández et
al. 1994; Burgueño-Tapia and Joseph-Nathan 1997).
Some pharmacological effects have been reported for
perezone: hypoglycemic action (Alarcón-Aguilar et al.
1997), induction of a biphasic dose-dependent contractile
response in calcium-free intestinal smooth muscle prepara-
tion (García et al. 1995), an increase in intestinal motility
(Enríquez et al. 1980), lack of sensitizing capacity (Hausen
J Chem Ecol (2008) 34:766–771
DOI 10.1007/s10886-008-9495-2
E. Burgueño-Tapia
Departamento de Química Orgánica, Escuela Nacional de
Ciencias Biológicas, Instituto Politécnico Nacional, Prolongación
de Carpio y Plan de Ayala, Col. Santo Tomás,
México, D.F. 11340, México
L. Castillo
:
A. González-Coloma
Instituto de Ciencias Agrarias, CCMA, CSIC,
Serrano 115-bis,
28006 Madrid, España
P. Joseph-Nathan (*)
Departamento de Química, Centro de Investigación y de Estudios
Avanzados del Instituto Politécnico Nacional,
Apartado 14-740,
México, D.F. 07000, México
e-mail: pjoseph@nathan.cinvestav.mx