Industrial Crops and Products 21 (2005) 8999

Anti-nutritive constituents in oilseed crops from Italy

Bertrand Matthus a, , Luciana G. Angelini b
b

a Federal Research Center for Nutrition and Food, Institute for Lipid Research, Piusallee 68/76, Mnster 48147, Germany
Dipartimento di Agronomia e Gestione dellAgroecosistema, Universit di Pisa, Via S. Michele degli Scalzi 2, 56124 Pisa, Italy

Received 21 February 2003; accepted 23 December 2003

Abstract
Eight different oilseed crops (Brassica carinata, Camelina sativa, Coriandrum sativum, Euphorbia lagascae, Lepidium
sativum, Lesquerella fendleri, Madia sativa, Vernonia galamensis) grown in Italy were investigated regarding anti-nutritive
compounds, such as glucosinolates, sinapine, inositol phosphates and condensed tannins, which can adversely affect the nutritional value of residues from the oilseed processing. In all seeds at least one anti-nutritive compound was found, which possibly
could lower the nutritive value, but in most cases a real negative effect is not to be expected. The existence and the concentration
of the different anti-nutritive components varied in the different seeds. Glucosinolates and sinapine were found only in seeds
of B. carinata, L. sativum, C. sativa and L. fendleri, whereas condensed tannins and inositol phosphates appeared in all seeds.
In the different seeds the amount ranged from 0.2 mg/g (L. fendleri) to 13.1 mg/g (L. sativum) for sinapine, from 0.4 mg/g (E.
lagascae) to 19.6 mg/g (L. fendleri) for condensed tannins, from 6.6 mg/g (E. lagascae) to 23.1 mg/g (B. carinata) for inositol
hexa-phosphate as well as from 18.7 mol/g (C. sativa) to 164.6 mol/g (L. sativum) for glucosinolates.
2004 Elsevier B.V. All rights reserved.
Keywords: Anti-nutritive compounds; Condensed tannins; Glucosinolates; Inositol phosphates; Oilseeds; Sinapine

1. Introduction
In the last three decades a number of new oilseed
crops have been introduced on the market providing
the industry with new or unusual fatty acids, such as
fatty acids with hydroxy or epoxy groups (Mikolajczak
et al., 1961; Abbott et al., 1997; Princen and
Rothfus, 1984; Haumann, 1991; Bramm and Rhl,
1996). These fatty acids are used as ingredients in
the production of a huge number of products such as
paints and coatings, detergents, cosmetics, lubricants,
Corresponding author. Tel.: +49-251-48167-14;
fax: +49-251-519275.
E-mail address: matthaus@uni-muenster.de (B. Matthus).

flavours or biodegradable polymers (Muuse et al.,

1992; Watkins, 1999).
One important point for the introduction of a new
industrial oil crop is according to views of Rbbelen,
that the companies have to find new end-markets for
their new products (Haumann, 1991), but another point
is that it is absolutely necessary to find also an adequate utilisation for the residue of the oil-pressing process on the market (Steg et al., 1994). Oil and residue
are strongly tied together, so that the success of an oil
crop depends on the utilisation of both products.
The residue of the oil-pressing process can be used
as fuel for power stations, but from an economical
point of view this residue should be used in the diet of
animals to get a better commercial exploitation of the

0926-6690/$ see front matter 2004 Elsevier B.V. All rights reserved.
doi:10.1016/j.indcrop.2003.12.021

90

B. Matthus, L.G. Angelini / Industrial Crops and Products 21 (2005) 8999

agricultural product (Steg et al., 1994). For an effective

organisation of the oil-pressing process it is necessary
to supply the valuable press cake to an utilization with
an added value.
Several press cakes of commercially used oilseed
crops provide an excellent potential source of protein supplement for the diet of animals, because the
residues are high in protein and additionally they
have an interesting amino acid composition (Lennerts,
1984; Niewiadomski, 1990). Unfortunately they also
contain at least one anti-nutritional factor such as
alkaloids, lectins, inositol phosphates, phenolic compounds, glucosinolates or trypsin inhibitors, which
lower the nutritive value of the residues and limit
the application of the residues in human or animal
nutrition (Duncan, 1991; Goh et al., 1979; Singleton,
1981). While condensed tannins and inositol phosphates can be found in almost all plant seeds in
different concentrations, some of these anti-nutritive
components are typical of specific plant families or
genus. Glucosinolates are a chemotaxonomic feature of seeds belonging to the family Brassicaceae,
whereas lectins are found above all in legumes, but
also in potatoes, wheatgerms or castor. Another important group of anti-nutritive components are trypsin
inhibitors, which are able to inhibit the activity of
certain enzymes responsible for the degradation of
proteins during digestion. These inhibitors are characteristic of pumpkin, but also of potatoes and legumes
(Holak et al., 1989).
During the oil-pressing process some of these
anti-nutritive components, such as inositol phosphates
or sinapine remain in the residue and depending on the
loss of oil an accumulation of these compounds takes
place (Matthus and Zubr, 2000). On the other side
it is also possible that oil-soluble substances partially
disappear from the seed material with the extracted
oil, resulting in a reduction of these compounds in the
residue. The content of condensed tannins in seeds of
Camelina sativa was reduced by about 3060% during the pressing process (Matthus and Zubr, 2000).
For the assessment of the applicability of the
residues in diets of animals the knowledge of the nature and quantity of anti-nutritive compounds in the
seeds is very important. Only then it is possible to assign certain effects on the animals after feeding with
the residues to the composition of the constituents of
the oilseeds.

In literature only very little information about the

occurrence and the composition of anti-nutritive compounds in new oilseed crops is available. Most information, if any, deals with anti-nutritive compounds in
residues of usually used oilseeds, such as rapeseed or
sunflower seeds. Unfortunately the data are also scattered in works of Bouchereau et al. (1991); Dabrowski
and Sosulski, (1984); Daxenbichler et al., 1991 and
no coherent work is available which investigates the
content of different anti-nutritive compounds in one
examination.
Therefore the aim of this work was to evaluate some
oilseed crops grown in Italy regarding anti-nutritive
constituents apparently important for the applicability
of the residues as a potential feed ingredient.

2. Materials and methods

2.1. Materials
Eight oilseed species, Brassica carinata, Camelina
sativa, Coriandrum sativum, Euphorbia lagascae, Lepidium sativum, Lesquerella fendleri, Madia sativa,
Vernonia galamensis, were assembled in a germplasm
collection and evaluated under field conditions at the
Experimental Centre of Rottaia (Pisa, Central Italy,
43 40 N.; 10 19 E.). Some accessions were provided by the Regional Plant Introduction Station of
Ames, Iowa (USA) and others were received from different European Botanical Gardens. The largest part
of these accessions included undomesticated forms
(Table 1).
Seeds of each species were sown in a cold greenhouse in March/April, and the resulting 3-week-old
plants were transplanted to deep silt loam soil (clay
18%, silt 66%, sand 16%, total nitrogen 1.1%,
pH = 7.7, and organic matter 2.2%). Seedlings of
each species were planted in small plots of 6 m2 ,
with inter-row and inter-plant spacing of 0.5 m and
0.1 m, respectively. For Euphorbia lagascae and Vernonia galamensis an inter-plant spacing of 0.3 m was
adopted. Fertilizer was applied at soil preparation, at
rates of 100/100/100 kg ha1 of N/P/K. Plots were
kept weed-free by hand hoeing.
Seeds were harvested manually at full maturity and
then seeds were forced-air dried (30 C) in a ventilated
chamber until 10% seed humidity was reached.

B. Matthus, L.G. Angelini / Industrial Crops and Products 21 (2005) 8999

91

Table 1
List of source and origin of samples
Species

Source

Origin

Code

Brassica carinata L.

L079444

Ethiopia

BC

Camelina sativa (L.) Crantz.

IGK Gattersleben
B.G. Frankfurt and Main
B.G. Poland
B.G. Russia
B.G. Russia
B.G. Sweden
B.G. Sweden
USDA-ARS

Germany
Germany
Poland
Russia
Russia
Sweden
Sweden
USA

CAM
CAM
CAM
CAM
CAM
CAM
CAM
CAM

Coriandrum sativum L.var. sativum

C. sativum L. var. microcarpum

SAIS SeedCo.
B.G. Gatersleben

Italy
Germany

COR
COR

Euphorbia lagasca

USDA-ARSPI296064
USDA-ARSPI308128

Spain
Spain

EU
EU

Lepidium sativum L.

SAIS SeedCo.

Italy

LE

Lesquerella fendleri (Gray) Wats.

USDA-ARS
USDA-ARSPI279649

USA
USA

FE
FE

Madia sativa Molina

B.G. Gatersleben
B.G. Frankfurt and Main

Germany
Germany

MAD
MAD

Israel

VE

Kenya

VE

Vernonia galamensis subsp. galamensis

var. ethiopica
V. galamensis subsp. afromontana

USDA-ARSPI500003

B.G indicates botanic garden. The pin number is the USA Genetic Resource Centre Storage number.

2.2. Determination of sinapine

The determination of sinapine was performed
according to a modified method of Clausen et al.
(1983) under isocratic conditions as described by
Clausen et al. (1985). The extraction of sinapine
from 2.00 g of grinded seed material was achieved
with 70% methanol as recommended by Bjerg et al.
(1984). The extract of was evaporated to dryness,
diluted in water and centrifuged. The centrifugation was carried out for 10 min at room temperature
with 4500 g. Then 20 l of the solution was injected
onto a LiChrospher 60 RP-select B column (5 m)
125 4 mm (Merck, Darmstadt, Germany) used with
a flow rate of 1.0 ml/min without further purification.
The mobile phase consisted of 0.01 M sodium heptanesulphonic acid (Fluka, Taufkirchen, Germany),
0.01 M sodium dihydrogenphosphate and 0.01 M
dibutylamine in acetonitrile/water (2:8) at pH = 2.0.
The UV-detector was set at 325 nm. Calibration and
evaluation of the method was made using sinapine

thiocyanate, isolated from a rapeseed sample as described by Kerber and Buchloh (Kerber and Buchloh,
1980). In brief, after extraction of grinded rapeseed
by ethanol, sinapine was precipitated by a solution of
10% potassium thiocyanate and then the raw material
was recrystallised two to four times with hot ethanol
(96%).
2.3. Determination of inositol hexa-phosphate and
its degradation products
Phytic acid and its degradation products inositol
(penta-phosphate, tetra-phosphate and tri-phosphate)
were determined by HPLC as described by Matthus
et al. (1995).
The grinded seed material (0.30 g) was defatted by
20 ml of petroleum ether and the air-dried residue was
extracted with 0.5 M HCl at 90 C to isolate the inositol phosphates. Afterwards the extract was passed
through an anion exchange column (Dowex 1 2
(Fluka, Taufkirchen, Germany)), where the inositol

92

B. Matthus, L.G. Angelini / Industrial Crops and Products 21 (2005) 8999

phosphates were retained. The column was washed

with a solution of sodium chloride and water to remove impurities and then the inositol phosphates were
eluted with 2 M HCl. The eluate was evaporated to
dryness and redissolved in 1 ml water. This solution
was used for HPLC, whereas the inositol phosphates
were detected by RI-detector. Samples of 10 l were
injected onto a LiChrospher 60 RP-select B (5 m)
125 4 mm (Merck, Darmstadt, Germany) used with
a flow rate of 1.0 ml/min. The mobile phase used consisted of 500 ml water, 500 ml methanol and 22.5 ]/l
tetrabutylammonium hydroxide (Fluka, Taufkirchen,
Germany) adjusted with 9 M H2 SO4 at pH 4.3.
2.4. Determination of condensed tannins
The determination of condensed tannins or its
monomeric components was carried out as described
by Price et al. (1978) and Butler et al. (1982). After
defatting of 2.00 g grinded seed material by 20 ml
petroleum ether, the samples were extracted with
70% (v/v) acetone, the extracts carefully evaporated
to dryness and then dissolved in 10 ml methanol. One
millilitre of this extract was mixed with 5 ml of the
vanillin reagent consisting of 4% concentrated HCl
and 0.5% vanillin in methanol. The reaction time was
20 min in the dark and the absorbance was read at
500 nm. As standard substance (+)-catechin was used
for calculating the level of condensed tannins in the
samples.
2.5. Determination of desulfoglucosinolates
Desulfoglucosinolates were determined as described by Fiebig and Jrden (1990). Sample extraction of 0.200 g grinded seed material was carried out
with 70% (v/v) methanol at 75 C for 10 min twice under ultrasonic treatment. The crude extract (1 ml) was
added on the top of a SAX exchange column (LiChrolut SAX 500 mg, Merck, Darmstadt, Germany) and
allowed to drain. The column was washed with water
and a sodium acetate buffer (1.3608 g sodium acetate
3 H2 O/500 ml water adjusted to pH = 4.0 by acetic
acid). A sulphatase solution (10.0 mg sulfatase/25 ml
water) (Type H-1 from Helix pomatia; E.C. 3.1.6.1,
SigmaAldrich Chemie GmbH, Taufkirchen, Germany) was added and allowed to remain on the column overnight. Desulphoglucosinolates were eluted

with water from the column and this solution was

used for the HPLC on a LiChrospher 60 RP-select B
column (5 m) 125 4 mm (Merck, Darmstadt, Germany). Separation was performed by gradient elution
using water (A) and 20% (v/v) acetonitrile in water
(B). The solvent gradient changed according to the
following conditions: after 2.5 min with 95% (A) and
5% (B) to 80% (A) and 20% (B) in 18 min. These
conditions were held for 5 min and then changed
to 95% (A) and 5% (B) in 2 min. The desulfoglucosinolates were detected at 229 nm with a variable
wavelength UV-detector.
The analyses were performed with five replicates.
The mean values and S.D. were calculated and tested
using the Student-t-test (P < 0.05). A statistical
analysis of variance (ANOVA) was performed on all
values using the statistical program Statgrafics Statistical Graphics System version 4.0 (Statgraphics,
1989).

3. Results and discussion

Eight different oilseeds were investigated regarding the content of sinapine, inositol phosphates, glucosinolates and condensed tannins, which lower the
nutritive value of residues from the oilseed processing. The investigation was performed with the whole
seeds instead of the residues. But it should be kept in
mind that during oilseed processing an accumulation
of glucosinolates, sinapine and inositol phosphates in
the residue took place, because these compounds remain in the residue, while the oil is removed from the
seeds (Matthus and Zubr, 2000). This accumulation
depends on the yield of oil during the oilseed processing and with the knowledge of this yield the results could be converted. On the other hand condensed
tannins will be extracted with the oil from the seeds,
so that the amount in the residue will be decreased
(Matthus and Zubr, 2000).
From L. sativum only one cultivar or genotype was
investigated, whereas from the other oilseeds at least
two cultivars or genotypes were available. In Figs. 14
the results of the investigation are summarized and the
variations of the results of different cultivars or genotypes of one individual species are given as vertical
black lines. Table 1 gives the sources and codes for
all species tested in this investigation.

Content of sinapine [mg/g] (calculated as sinapine

thiocyanate)

B. Matthus, L.G. Angelini / Industrial Crops and Products 21 (2005) 8999

93

14
12
10
8
6
4
2
0
BC

CAM

LE

FE

Fig. 1. Concentration of sinapine in B. carinata (BC), C. sativa (CAM), L. sativum (LE) and L. fendleri (FE). The vertical line on the
bars shows the variation of the results of different cultivars or genotypes of each species.

3.1. Sinapine

traces of sinapine (0.2 mg/g). The values found for L.

sativum, B. carinata and C. sativa were comparable
with contents of other common used oilseeds such as
mustard (13 mg/g) and rapeseed (7 mg/g) (Matthus,
1997). However, seeds of Crambe abyssinica, another
member of the family Brassicaceae, consisted of only
1 mg sinapine/g.
Sinapine is described as the bitter constituent of different oilseeds belonging to the family Brassicaceae.

25

inositol hexaphosphate
inositol pentaphosphate

20

15

10

5
0

Concentration of inositolpenta- and -hexaphosphate

(phytic acid) [mg/g]

In the present investigation sinapine was detected

in seeds of B. carinata, C. sativa, L. fendleri and
L. sativum. Seeds of L. sativum contained the highest amount of sinapine (13.2 mg/g), whereas in seeds
of B. carinata and C. sativa not even a half of this
amount was found (5.9 mg/g and 4.0 mg/g, respectively) (Fig. 1). Seeds of L. fendleri contained only

BC

CAM

COR

EU

LE

FE

MAD

VE

Fig. 2. Concentration of inositol (penta- and hexa-phosphates) in different oilseeds. The vertical line on the bars shows the variation of
the results of different cultivars or genotypes of each species. Codes for each crop are defined in Table 1.

B. Matthus, L.G. Angelini / Industrial Crops and Products 21 (2005) 8999

Content of condensed tannins [mg/g] (calculated as
catechin)

94

25

20

15

10

0
BC

CAM

COR

EU

LE

FE

MAD

VE

Fig. 3. Concentration of condensed tannins in different oilseeds. The vertical line on the bars shows the variation of the results of different
cultivars or genotypes of each species.

Some hens are unable to change TMA in odourless TMA-oxid because of a reduced TMA-oxidaseactivity, which results in stink eggs.
The occurrence of a crabby or fishy taint of
eggs is described for the use of rapeseed meal in the
fodder of certain hens and an inclusion of more than
1 g of sinapine/kg of laying ration caused eggs with a
fishy odour (Pearson et al., 1980; Goh et al., 1979).

80
70
60
50
40
30
20

Glucoiberin

MSG-11

MSG-9

Glucobrassicin

4Hydro.glucobr.

MSG-10

CAM

Glucotropaeolin

BC

Gluconapin

Progoitrin

Sinigrin

10
Glucotropaeolin

Content of glucosinolates [mol/g]

This component is of special interest because of its

bitter taste and its responsibility for crabby or fishy
taint notes in eggs from some brown-egg-laying
hens (Butler et al., 1982; Fenwick et al., 1984) fed
with rapeseed meal. During the digestion sinapine is
hydrolysed and the formed choline is converted to
trimethylamine (TMA) by micro organisms (Pearson
et al., 1979). Traces of TMA go into the yolk.

LE

FE

Fig. 4. Concentration of different glucosinolates in B. carinata (BC), C. sativa (CAM), L. sativum (LE) and L. fendleri (FE). (10-MSG)
is 10-methylsulfinyldecyl-Gls, (9-MSG) 9-methylsulfinylnonyl-Gls and (11-MSG) 11-methylsulfinylundecyl-Gls). The vertical line on the
bars shows the variation of the results of different cultivars or genotypes of each species. Codes for each crop are defined in Table 1.

B. Matthus, L.G. Angelini / Industrial Crops and Products 21 (2005) 8999

For rapeseed an amount of about 7 mg sinapine/g was

found (Matthus, 1997). Therefore it could be expected from the concentrations found in seeds of B.
carinata, C. sativa and L. sativum that an addition of
residues of these seeds to a diet would result in a similar effect. For residues of B. carinata and C. sativa
this effect will be a little less pronounced than for L.
sativum, which contained nearly double the amount as
rapeseed. For all residues the part in the ratio has to
be limited to avoid a fishy taint of eggs.
3.2. Inositol phosphates
In all investigated seeds inositol phosphates in different amounts were found (Fig. 2). The main part
of inositol phosphates was contributed by inositol
hexa-phosphate (phytic acid (IP6)), whereas the part
of inositol penta-phosphate (IP5) normally constitutes less than 10% of the total inositol phosphates.
Other degradation products of IP6 were not detected,
which indicated that a greater degradation of inositol
hexa-phosphate took not place.
The values for IP6 varied between 6.6 mg/g for E.
lagascae and 23.1 mg/g for B. carinata. The amount
of IP6 in most of the seeds was in a range between 10
and 20 mg/g, only in seeds of E. lagascae, L. fendleri
and V. galamensis lower amounts were found.
The amount of IP6 found in seeds of C. sativa, C.
sativum, L. sativum and M. sativa was comparable
with the amount found in rapeseed (17.4 mg/g), which
is widely applied as constituent of fodder for animal
nutrition.
Inositol hexa-phosphate represents the major storage form of phosphorus in plants. Both, in human and
animal nutrition this compound is responsible for different anti-nutritive effects such as forming of insoluble complexes with nutritionally important minerals
(Fe, Zn, Mg and Ca). As a result of the strong chelating properties phytic acid is able to interact with proteins or digestive enzymes (Thompson, 1990). During
food processing, storage and germination of seeds
also degradation products of phytic acid with fewer
phosphate groups (IP5 to IP1) are formed by chemically or enzymatically dephosphorylation. The ability
of these degradation products to form complexes with
minerals or proteins is much smaller than that of IP6
(Jackman and Black, 1951; Kaufman and Kleinberg,
1971).

95

Additionally to the anti-nutritive effects of inositol

phosphates it was shown in recent research that IP6
prevents and possibly reverses carcinogenesis (Graf
and Eaton, 1993; Shamsuddin, 1995), that it is considered to work as a hypocholesterolemic agent (Jariwalla
et al., 1990) and that it is able to prevent renal stone
formation (Sharma, 1986) as well as phytic acid has
antioxidative properties (Graf and Eaton, 1990).
From the amounts of inositol phosphates found in
the different seeds a concrete effect on the animals fed
with residues from these seeds can not be assumed.
However, a worst availability of enzymes or minerals
as a result of the presence of inositol hexa-phosphate
and its degradation products is conceivable.
3.3. Condensed tannins
All seeds contained condensed tannins, but only in
seeds of L. fendleri (19.5 mg/g), L. sativum (7.4 mg/g)
and B. carinata (3.4 mg/g) higher amounts were found
(Fig. 3). The content in the other seeds ranged between 0.4 g/mg (E. lagascae) and 1.1 mg/g (C. sativa).
Compared with other oilseeds the amounts of condensed tannins in seeds of L. fendleri and L. sativum
were remarkable high. In seeds from sunflower, mustard, rapeseed, crambe or soybeans the amounts varied
between 0.1 (sunflower seeds) to 4 mg/g (rapeseed)
(Matthus, 1997).
Phenolic compounds such as phenolic acids or tannins represent a wide and diverse group of secondary
plant products. They can be found in a wide range of
plant species. Condensed tannins may be considered
as dimers or higher oligomers of variously substituted
flavan-3-ols. In oilseeds these compounds are mainly
located in the seed coats.
Regarding the nutritive value of these components
in animal nutrition, they represent potentially toxic
dietary substances which can seriously lower the digestibility of feeds in nonruminants (Clandinin and
Robblee, 1981; Martin-Tanguy et al., 1977) and ruminants (Kumar and Singh, 1984). The anti-digestive
effect was ascribed to reactions with proteins, enzymes or essential amino acids after enzymatic or
non-enzymatic oxidation of the phenolics and the
formation of various complexes. It was also found
that the addition of extracted tannins from rapeseed,
to soybean-containing diets for chicks resulted in a
reduction of its metabolisable energy, whereas the

96

B. Matthus, L.G. Angelini / Industrial Crops and Products 21 (2005) 8999

absorption of protein was not affected (Yapar and

Clandinin, 1972).
The vanillin method, used in the present investigation is specific for tannins that possess a single bond at
the 2,3-position of the pyran ring and free OH groups
at positions 5 and 7 of the benzene ring (Sarkar and
Howarth, 1976). Additionally to tannins this reagent
is known to react with some flavanols, dihydrochalcones and anthocyanins, whereas the specificity of
this method is much higher in comparison to different redox-based methods, such as the FolinDennis
method.
The total amount of condensed tannins in seeds
of B. carinata, C. sativa, C. sativum, E. lagascae,
M. sativa and V. galamensis was relatively low and
therefore only a small nutritive effect, if any, can
be expected. Higher amounts were found merely in
seeds of L. fendleri and L. sativum. This data indicate
that especially meal of L. fendleri should be tested
for nutritional utilisation before it can be used as an
animal feed. Tannins are only seriously toxic when
consumed in large amounts (more than 1% of the
diet) (Singleton, 1981), but the tannin level necessary
for rejection by grazing animals is about 20 mg/g of
dry matter (Kumar and Singh, 1984), which is comparable with the amount found in seeds of L. fendleri.
3.4. Glucosinolates
Only in seeds of B. carinata, L. fendleri, L. sativum
and C. sativa glucosinolates were found. The amounts
and patterns of glucosinolates were very different
(Fig. 4). The highest amount of glucosinolates was
found in seeds of L. sativum (164.6 mol/g), whereas
seeds of C. sativa and L. fendleri comprised only relatively small amounts (18.6 and 27.5 mol/g, respectively). Seeds of B. carinata contained 77.1 mol/g.
While glucosinolates of B. carinata consisted of
six different compounds, seeds of L. sativum and
L. fendleri contained only one glucosinolate in a
high amount. In these seeds glucotropaeolin and
glucoiberin, respectively, were found as only glucosinolates. The main glucosinolate of B. carinata was
sinigrin with more than 90% of the total glucosinolates. Seeds of C. sativa comprised of three different
glucosinolates. The distribution of glucosinolates
was a little more well-balanced. Glucocamelinin
(10-methylsulfinyldecyl-Gls i.e. 10-MSG) was the

main glucosinolate by about 60% of the total glucosinolates, whereas 9-methylsulfinylnonyl-Gls (9-MSG)
and 11-methylsulfinylundecyl-Gls (11-MSG) came to
about 30 and 10%, respectively.
These values found in the different seeds were comparable to other investigations. Daxenbichler et al.
(1991) described similar amounts of glucosinolates in
B. carinata (111 mol/g), C. sativa (38 mol/g), L.
fendleri (70 mol/g) and L. sativum (127 mol/g).
In comparison to other oilseeds such as crambe
or mustard (115 and 130 mol/g, respectively) the
amounts found in C. sativa or L. fendleri were low,
whereas the content of glucosinolates found in B. carinata and L. sativum was comparable to levels reported
on crambe and mustard. The content of glucosinolates
found in C. sativa and L. fendleri was comparable to
amounts found in rapeseed.
Glucosinolates are natural substances, which can
be found in many plants and vegetables. These compounds are especially widespread in the family of
Brassicaceae. More than 100 different glucosinolates are known (Kjaer and Skrydstrup, 1987). They
are relatively non-toxic (Bell, 1984), but glucosinolates gain importance from the fact that the products
of a myrosinase (thioglucoside glucohydrolase (EC
3.2.3.1)) induced degradation adversely affect animal
growth, reproductive performance as well as intake
and palatability of fodder. Degradation products also
cause goitre and abnormalities in internal organs of
animals (Mawson et al.,1994a,b; Singleton, 1981;
Griffiths, 1989; Thompson, 1990). On the other hand
it is known that glucosinolates are responsible for
the anticarcinogenic activity of Brassica vegetables
(Mithen et al., 2000; Uhl et al., 2001).
From a nutritional point of view the composition
of glucosinolates is important for the assessment of
the glucosinolates, because the effects resulting from
the presence of glucosinolates depend on the nature
of the breakdown products, after degradation and
absorption. Depending on the conditions, if the formation of nitriles predominates, this results in liver
and kidney damage (VanEtten et al., 1966; Nishie
and Daxenbichler, 1980), whereas oxazolidines are
formed from high levels of -hydroxy substituted
aliphatic glucosinolates such as progoitrin, affecting
the organic iodination of thyroxine in the biosynthesis of tyroid hormones. Low iodine availability in the
diet in combination with high levels of thiocyanate

B. Matthus, L.G. Angelini / Industrial Crops and Products 21 (2005) 8999

ions from the degradation of glucosinolates under acidic conditions will cause goitrogenic effects
(Mawson et al.,1994a,b). Investigations of Nishie and
Daxenbichler, 1980 had shown that the toxicity of
short-chain sulfinyl-glucosinolates like glucoiberin
was comparable to the toxicity of sinigrin or progoitrin. Glucosinolates with longer side-chains should
have a smaller effect (Schumann and Stlken, 1996).
Thus, the effect of glucosinolates from C. sativa could
be considered as comparable or rather smaller than
the effect of glucosinolates from rapeseed products.
This is different to B. carinata and L. fendleri which
contain short-chain glucosinolates such as sinigrin or
glucoiberin in high amounts.
The glucosinolate content of seeds from L. fendleri
and C. sativa, but especially from B. carinata and L.
sativum indicates that the use of residues from these
oilseeds is strongly limited. There are different studies showing that a high amount of glucosinolates is
responsible for growth depression, reduced food intake or enlargement of the thyroid (Fenwick et al.,
1989; Pusztai, 1989). For example, at a concentration
of 36.6 mol glucosinolates/g a reduction of the food
intake by 45% took place (Pusztai, 1989). In L. fendleri and C. sativa the amount of glucosinolates was
comparable to the amount found in rapeseed, so with
regard to this class of compounds the use of such
residues should be comparable. It looks different for
residues from B. carinata and L. sativum, which contained three- to nine-fold higher amounts of glucosinolates. This leads to the assumption that the use of
these residues is questionable.

4. Conclusions
All seeds included in this investigation contained
at least one anti-nutritive compound with possible adverse effects on living organisms, but in most cases a
real negative influence is hardly to be expected from
the use of the residues as fodder in animal nutrition.
Only the composition of seeds from L. fendleri indicated that the use of this residue as fodder could result in negative effects, because of the high level of
glucosinolates and condensed tannins.
Regarding the content of glucosinolates it is to be
expected that it may not be possible to add unlimited
amounts of residues from L. fendleri, C. sativa, B.

97

carinata as well as L. sativum to the fodder of animals.

As in the case of rapeseed the admixture have to be
limited to certain amounts. A further factor that limits
the use of residues from C. sativa, B. carinata and
L. sativum is the presence of sinapine in remarkable
amounts.
For all the seeds certain interactions between phytic
acid and condensed tannins on the one hand, and
protein and minerals on the other hand can result
in a lower bioavailability of important nutritive compounds.

References
Abbott, T.P., Dierig, D.A., Foster, M., Nelson, J.M., Coates, W.,
Frykman, H.B., Carlson, K.D., Arquette, J.D., 1997. Status of
lesquerella as an industrial crop. INFORM 8, 11691175.
Bell, J.M., 1984. Nutrients and toxicants in rapeseed meal: a
review. J. Anim. Sci. 58, 9961010.
Bjerg, B., Olsen, O., Rassmussen, K.W., Sorensen, H., 1984.
New principles of ion-exchange techniques suitable to sample
preparation and group separation of natural products prior to
liquid chromatography. J. Liq. Chromatogr. 7, 691707.
Bouchereau, A., Hamelin, J., Lamour, I., Renard, M., Larher, F.,
1991. Distribution of sinapine and related compounds in seeds
of brassica and allied genera. Phytochemistry 30, 18731881.
Bramm, A., Rhl, G., 1996. Evaluierung potentieller lpflanzenarten zur einheimischen Erzeugung hochwertiger
Ausgangsstoffe fr die chemische Industrie. In: Eierdanz H.
(Ed.), Perspektiven nachwachsender Rohstoffe in der Chemie,
VCH, pp. 223227.
Butler, E.J., Pearson, A.W., Fenwick, G.R., 1982. Problems which
limit the use of rapeseed meal as a protein source in poultry
diets. J. Sci. Food Agric. 33, 866875.
Clandinin, D.R., Robblee, A.R., 1981. Rapeseed meal in animal
nutrition. Part II. Non-ruminant animals. J. Am. Oil Chem.
Soc. 58, 682686.
Clausen, S., Olsen, O., Sorensen, H., 1983. Separation of aromatic
choline esters by high performance liquid chromatography. J.
Chromatogr. 260, 193199.
Clausen, S., Larsen, L.M., Plger, A., 1985. Aromatic choline
esters in rapeseed. In: Sorensen, H. (Ed.), Vol. 11. Martinus
Nijhoff/Dr. W. Junk Publishers, pp. 6171.
Dabrowski, K.J., Sosulski, F.W., 1984. Composition of free and
hydrolyzable phenolic acids in defatted flours of ten oilseeds.
J. Agric. Food Chem. 32, 128130.
Daxenbichler, M.E., Spencer, G.F., Carlson, D.G., Rose, G.B.,
Brinker, A.M., Powell, R.G., 1991. Glucosinolate composition
of seeds from 297 species of wild plants. Phytochemistry 30,
26232638.
Duncan, A.J., 1991. Glucosinolates. In: DMello, J.P.F., Duffus,
C.M., Duffus, J.J. (Ed.), Toxic Substances in Crop Plants,
Royal Society of Chemistry, pp. 126147.

98

B. Matthus, L.G. Angelini / Industrial Crops and Products 21 (2005) 8999

Fenwick, G.R., Curl, C.L., Pearson, A.W., Butler, E.J., 1984.

The treatment of rapeseed meal and its effect on chemical
composition and egg tainting potential. J. Sci. Food Agric. 35,
757761.
Fenwick, G.R., Heaney, R.K., Mawson, R., 1989. Glucosinolates.
In: Cheeke, R.R. (Ed.), Toxicants of Plant Origin, Vol. 2. CRC
Press, pp. 141.
Fiebig, H.-J., Jrden, M., 1990. HPLC of desulfoglucosinolates.
J. High Resolut. Chromatogr. Chromatogr. Commun. 13, 377
379.
Goh, Y.K., Glandinin, D.R., Robblee, A.R., Darlington, K., 1979.
The effect of level of sinapine in a laying ration on the
incidence of fishy odor in eggs from brown-shelled egg layers.
Can. J. Anim. Sci. 59, 313316.
Graf, E., Eaton, J.W., 1990. Antioxidant functions of phytic acid.
Free Radic. Biol. Med. 8, 6169.
Graf, E., Eaton, J.W., 1993. Suppression of colonic cancer by
dietary phytic acid. Nutr. Cancer 19, 1119.
Griffiths, D.W., 1989. Polyphenolics and their possible effects on
nutritive value. Asp. Appl. Biol. 19, 93103.
Haumann, B.F., 1991. Work continues on new oils for industrial
use. INFORM 2, 678692.
Holak, T., Gondol, D., Otlewski, J., Wilusz, T., 1989.
Determination of the complete three-dimensional structure of
the trypsin inhibitor from squash seeds in aqueous solution
by nuclear magnetic resonance and a combination of distance
geometry and simulated annealing. J. Mol. Biol. 210, 635
648.
Jackman, R.H., Black, C.A., 1951. Solubility of iron, aluminium,
calcium, and magnesium inositol phosphates at different pH
values. Soil Sci. 72, 179186.
Jariwalla, R.J., Sabin, R., Lawson, S., Herman, Z.S., 1990.
Lowering of serum cholesterol and triglycerides and
modulation of divalent cations by dietary phytate. J. Appl.
Nutr. 42, 1825.
Kaufman, H.W., Kleinberg, T., 1971. Effect of pH on calcium
binding by phytic acid and its inositol phosphoric acid
derivations on the solubility of their calcium salts. Aral. Oral
Biol. 16, 445460.
Kerber, E., Buchloh, G., 1980. The sinapine content of seeds of
crucifers. Angew. Botanik 54, 4754.
Kjaer, A., Skrydstrup, T., 1987. Selenoglucosinolates: synthesis
and enzymatic hydrolysis. Acta. Chem. Scand. 41, 2933.
Kumar, R., Singh, M., 1984. Tannins: their adverse role in ruminant
nutrition. J. Agric. Food Chem. 32, 447453.
Lennerts, L., 1984. lschrote, lkuchen, pflanzliche le und
FetteHerkunft, Gewinnung und Verwendung, Verlag Alfred
Strothe.
Martin-Tanguy, J., Guillaume, J., Kossa, A., 1977. Condensed
tannins in horse bean seeds: chemical structure and apparent
effects on poultry. J. Sci. Food Agric. 28, 757765.
Matthus, B., Lsing, R., Fiebig, H.-J., 1995. Determination of
inositol phosphates IP3-IP6 in rapeseed and rapeseed meal by
an HPLC method I. Method Fat Sci. Technol. 97, 289291.
Matthus, B., 1997. Anti-nutritive compounds in different oilseeds.
Fett. Lipid 99, 170174.

Matthus, B., Zubr, J., 2000. Variability of specific components

in Camelina sativa oilseed cakes. Ind. Crops Prod. 12, 9
18.
Mawson, R., Heaney, R.K., Zdunczyk, Z., Kozlowska, H., 1994a.
Rapeseed meal-glucosinolates and their antinutritional effects.
Part 4. Goitrogenicity and internal organs abnormalities in
animals. Die Nahrung 38, 178191.
Mawson, R., Heaney, R.K., Zdunczyk, Z., Kozlowska, H., 1994b.
Rapeseed meal-glucosinolates and their antinutritional effects.
Part 5. Animal reproduction. Die Nahrung 38, 588598.
Mikolajczak, K.L., Miwa, T.K., Earle, F.R., Wolff, I.A., 1961.
Search for new industrial oils. Part V. Oils of Cruciferae. J.
Am. Oil Chem. Soc. 38, 678681.
Mithen, R.F., Dekker, M., Verkerk, R., Rabot, S., Johnson,
I.T., 2000. The nutritional significance, biosynthesis and
bioavailability of glucosinolates in human food. J. Sci. Food
Agric. 80, 967984.
Muuse, B.G., Cuperus, F.P., Derksen, J.T.P., 1992. Composition
and physical properties of oils from new oilseed crops. Ind.
Crops Prod. 1, 5765.
Niewiadomski H., 1990. RapeseedChemistry and Technology
Nutritional Value of Rapeseed Meal, Elsevier, pp. 397428.
Nishie, K., Daxenbichler, M.E., 1980. Toxicology of glucosinolates, related compounds (nitriles, r-goitrin, isothiocyantes)
and vitamin U found in cruciferae. Fd. Cosmet. Toxicol. 18,
159172.
Pearson, A.W., Butler, E.J., Curtis, F., Fenwick, R.G., HobsonFrohock, A., Land, D., 1979. Effect of rapeseed meal on
hepatic trimethylamine oxidase activity in the domestic fowl
in relation to egg taint. J. Sci. Food Agric. 30, 291298.
Pearson, A.W., Butler, E.J., Fenwick, R.G., 1980. Rapeseed meal
and egg taint: the role of sinapine. J. Sci. Food Agric. 31,
898904.
Price, M.L., Van Scoyoc, S., Butler, L.G., 1978. A critical
evaluation of the vanillin reaction as an assay for tannin in
sorghum grain. J. Agric. Food Chem. 26, 12141218.
Princen, L.H., Rothfus, J.A., 1984. Development of new crops for
industrial raw materials. J. Am. Oil Chem. Soc. 61, 281289.
Pusztai, A., 1989. Anti-nutrients in rapeseeds. Nut. Abstracts and
Rev. (Series B) 59, 427433.
Sarkar, S.K., Howarth, R.E., 1976. Specificity of the vanillin test
for flavanols. J. Agric. Food Chem. 24, 317320.
Schumann, W., Stlken, B., 1996. Glucosinolate content
and type of Camelina sativa seed. VDLUFA-Schriftenr.
Kongressband 1996. Trier Sekundrrohstoffe im Stoffkreislauf
der Landwirtschaft 44, 233236.
Shamsuddin, A.M., 1995. Inositol phosphates have novel
anticancer function. J. Nutr. 125, 725S732S.
Sharma, R.D., 1986. Phytate and the epidemiology of heart disease,
renal calculi and colon cancer. In: Graf, E. (Ed.), Phytic Acid
Chemistry and Applications, Pilatus Press, p. 161.
Singleton, V.L., 1981. Naturally occurring food toxicants: phenolic
substances of plant origin common in foods. Adv. Food Res.
27, 149242.
Steg, A., Hindle, V.A., Yong-Gang, L., 1994. By-products of some
novel oil seeds for feeding: laboratory evaluation. Anim. Feed
Sci. Technol. 50, 8799.

B. Matthus, L.G. Angelini / Industrial Crops and Products 21 (2005) 8999

Thompson, L.U., 1990. Phytates in canola/rapeseed. In: Shahidi,
F. (Ed.), Canola and Rapeseed Production, Chemistry,
Nutrition and Processing Technology, Van Nostrand Reinhold,
pp. 171192.
Uhl, M., Steinkellner, H., Kassie, F., Laky, B., Knasmller,
S., 2001. Beeinflussung der menschlichen Gesundheit durch
Glukosinolate (EFGLU)Ziele und Ergebnisse. Zeitschrift fr
Ernhrungskologie 2, 5660.

99

VanEtten, C.H., Daxenbichler, M.E., Peters, J.E., Tookey, H.L.,

1966. Variation in enzymatic degradation products from the
major thioglucosides in Crambe abyssinica and Brassica napus
seed meals. J. Agric. Food Chem. 14, 426430.
Watkins, C., 1999. Crambeready to be a commercial success.
INFORM 10, 828836.
Yapar, Z., Clandinin, D.R., 1972. Effect of tannins in rapeseed meal
on its nutritional value for chicks. Poultry Sci. 51, 222228.