Biology Reference
In-Depth Information
10
Alkylresorcinols: Chemical
Properties, Methods of Analysis
and Potential Uses in Food, Industry
and Plant Protection
Marta A. Vattuone
1†
and César A.N. Catalán
2
1
LABIFITO;
2
INQUINOA-Facultad de Bioquímica Química y Farmacia,
Universidad Nacional de Tucumán, Argentina
10.1
Introduction
properties, bioactivities and their possible
uses in nutrition, agriculture and industry.
Phenolic compounds represent a large
group of molecules widely distributed in
the plant kingdom, where they have a vari-
ety of functions in growth, development
and defence. These natural products include
signalling molecules, pigments and flavours
that can attract or repel, as well as allelo-
chemicals that can protect plants against
insects, fungi, bacteria and viruses (Posmyk
and Janas, 2009). Phenolic lipids or long-
chain phenols belong to this type of molecule
and are of increasing interest in phytochem-
istry. This chapter focuses on the non-
isoprenoid alkyl derivatives of resorcinol,
also known as alkylresorcinols (ARs). Until
now, several good reviews were dedicated
to different aspects of ARs (Kozubek and
Tyman, 1999, 2005; Kozubek
et al
., 2001;
Zarnowski and Kozubek, 2002; Ross
et al
.,
2004a,c). Here, we revise ARs in the light of
our own research interests, including plant
sources, methods of analysis, biological role
in plants and microorganisms, chemical
10.2
Chemical Properties
and Biosynthesis
The chemical structure of 5-n-ARs is charac-
terized by a benzene ring with two hydroxyl
groups located at positions 1 and 3 (the
hydrophilic head), and a non-isoprenoid
alkyl chain attached at position 5 (the
hydrophobic tail; Fig. 10.1). Orcinol is the
simplest homologue of the 1,3-dihydroxy-5-
n-alk(en)ylbenzene series. Their homologues
differ in the alkyl tail and are classified
according to a combination of tail length
(11-29 carbons) and the degree of unsatura-
tion (0-4 double bonds). These compounds
have a strong amphiphilic character that is a
consequence of the hydrophilic and hydro-
phobic regions previously indicated. This
characteristic is an important aspect with
regard to AR analysis, absorption, metabo-
lism and potential bioactivity. The ARs are
* E-mail: dasampietro2006@yahoo.com.ar
†
Email: mavattu@gmail.com
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