Page 1071 - Veterinary Toxicology, Basic and Clinical Principles, 3rd Edition

VetBooks.ir Chapter 71

Fumonisins

Geof W. Smith

INTRODUCTION BACKGROUND
Fumonisins are a group of naturally occurring mycotox- Chemical Structure
ins produced by the fungi Fusarium verticillioides (for-
First isolated in 1988, the fumonisins are a group of
merly F. moniliforme), Fusarium proliferatum and other
structurally related compounds with the terminal carboxy
Fusarium species. These toxic metabolites of corn have
group composed of propane-1,2,3-tricarboxylic acid
been implicated in field cases of porcine pulmonary
involved in ester formation with the C-14 and C-15
edema (PPE) (Colvin et al., 1993; Harrison et al., 1990;
hydroxy groups. The 20C chain base carries either 2-acet-
Osweiler et al., 1992) and equine leukoencephalomala-
ylamino or 2-amino-12,16-dimethyl-3,5,10,14,15, penta-
cia (ELEM) (Jovanovi´ c etal.,2015; Wilsonetal.,
hydroxyicosane (Fig. 71.1). The structures of FB 1 and
1990a). Experimentally, fumonisin has been shown to
cause liver damage in multiple species including pigs, FB 2 have been shown to have the empirical formulas of
C 34 H 59 NO 15 and C 34 H 59 NO 14 , respectively, with the only
horses, cattle, rabbits, and primates (Gumprecht et al.,
difference being the hydroxyl group present at the C-10
1995; Haschek et al., 1992; Jaskiewicz et al., 1987;
position in FB 1 (Bezuidenhout et al., 1988). Additional
Osweiler et al., 1993; Ross et al., 1993; Voss et al.,
fumonisin metabolites have been isolated (including B 3 ,
1989) as well as species-specific target organ toxicity,
B 4 ,B 5 ,B 6 ,A 1 , and A 2 ), but appear to occur in much
such as lung in pigs (Haschek et al., 1992), brain in
lower concentrations than FB 1 or FB 2 , and are considered
horses (Ross et al., 1993), kidney in rats, rabbits, and
less important at this time (Gelderblom et al., 1992).
sheep (Edrington et al., 1995; Gumprecht et al., 1995;
Voss et al., 1989), and esophagus in rats and pigs
(Casteel et al., 1993; Lim et al., 1996). Many grain-
based human foods have been shown to be contaminated Occurrence and Distribution
with fumonisin metabolites (Scott, 2012) and epidemio-
Although fumonisin metabolites have been found in many
logic data has linked ingestion of corn contaminated
different grains including barley, millet, oats, and wheat
with F. verticillioides to human esophageal cancer
(Scott, 2012), they are most commonly detected in corn
(Rheeder et al., 1992) and infant neural tube defects
and corn-based foods. ELEM has long been associated
(Voss et al., 2011). Fumonisins have been shown to be
with the consumption of moldy corn, and has been
hepatocarcinogenic in rats and mice (Gelderblom et al.,
reported in most of the world’s continents. Specific cases
1988; Howard et al., 2001) and the International Agency
of ELEM that were directly associated with fumonisin-
for Research on Cancer (IARC) has designated fumoni-
contaminated feed have been reported in South Africa
sin B1 in Group 2B meaning “possibly carcinogenic to
and Egypt (Thiel et al., 1991), the United States (Ross
humans.” More recently the fungus Aspergillus niger
et al., 1991; Wilson et al., 1990a), Brazil (Sydenham
has also been shown to produce some fumonisin meta-
et al., 1992), Hungary (Bela and Endre, 1996), Spain
bolites, whichhavebeenfoundingrapes, raisins, wine,
(Cerrillo et al., 1996), New Caldonia (Bailly et al., 1996),
and coffee (Scott, 2012).
Mexico (Rosiles et al., 1998), Iran (Raoofi et al., 2003),
Veterinary Toxicology. DOI: http://dx.doi.org/10.1016/B978-0-12-811410-0.00071-4
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