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Plants of the Brassicales order, and, in particular, the species belonging to the Brassicaceae family, are characterized by the presence of the glucosinolate (GLs)- myrosinase (MYR) system, an efficient internal defensive system that plays a role in the control of several types of pathogens. After wounding or a pathogen attack, GLs are hydrolyzed by MYR and release isothiocyanates (ITCs) harmful to pathogens or pests. The exploitation of this system has led to the definition of the "biofumigation" technique arising from the use of the biocidal properties of ITCs released from GLcontaining plants and materials. In addition, Brassicaceae seeds are characterized by an oil content ranging from 10 to 45 % of their dry matter. The oils contain different fatty acids that confer different tribological properties for the production of bioenergy, biolubricants and molecules for lipochemistry. In order to better exploit and increase our knowledge of the Brassicaceae biodiversity, our research group has collected seeds from several wild and cultivated non-food species. They were characterized for their GL and fatty acid composition and the most interesting species were tested for their adaptability to full-field cultivation. This study characterizes a collection of seeds of 66 Brassicaceae species, preserved and available at CRA-CIN. The results confirm a wide variation in their profile that could open some application perspectives.
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331
Characterization of the Main Glucosinolate Content and Fatty Acid
Composition in Non-Food Brassicaceae Seeds
L. Lazzeri, L. Malaguti, M. Bagatta, L. D’Avino, L. Ugolini, G.R. De Nicola, N. Casadei,
S. Cinti, R. Matteo and R. Iori
Consiglio per la Ricerca e la Sperimentazione in Agricoltura
Centro di Ricerca per le Colture Industriali (CRA-CIN)
Bologna
Italy
Keywords: bioactive phytochemicals, isothiocyanates, non-food crops, myrosinase, green
chemicals
Abstract
Plants of the Brassicales order, and, in particular, the species belonging to the
Brassicaceae family, are characterized by the presence of the glucosinolate (GLs)-
myrosinase (MYR) system, an efficient internal defensive system that plays a role in
the control of several types of pathogens. After wounding or a pathogen attack, GLs
are hydrolyzed by MYR and release isothiocyanates (ITCs) harmful to pathogens or
pests. The exploitation of this system has led to the definition of the “biofumigation”
technique arising from the use of the biocidal properties of ITCs released from GL-
containing plants and materials. In addition, Brassicaceae seeds are characterized by
an oil content ranging from 10 to 45 % of their dry matter. The oils contain different
fatty acids that confer different tribological properties for the production of bioenergy,
biolubricants and molecules for lipochemistry. In order to better exploit and increase
our knowledge of the Brassicaceae biodiversity, our research group has collected seeds
from several wild and cultivated non-food species. They were characterized for their
GL and fatty acid composition and the most interesting species were tested for their
adaptability to full-field cultivation. This study characterizes a collection of seeds of 66
Brassicaceae species, preserved and available at CRA-CIN. The results confirm a wide
variation in their profile that could open some application perspectives.
INTRODUCTION
Brassicaceae is the most important family included in the Brassicales order,
containing about 350 plant genera and 3709 species (Warwick et al., 2006). These
vegetables are a rich source of Glucosinolates (GLs), a class of glucosidic sulphur-
containing secondary metabolites displaying a common structure and a hydrophobic
aglycon side chain. Around 132 GLs have been identified (Agerbirk and Olsen, 2012) and
classified as aliphatic, aromatic and indole GLs, according to the wide variety of their
side chain (Fahey et al., 2001). GLs constitute an efficient plant defensive system, being
hydrolyzed, upon plant tissue damage, by the endogenous enzyme myrosinase (β-thio-
glucoside glucohydrolase; EC 3.2.1.147) and releasing isothiocyanates (ITCs), bio-active
degradation products harmful to pathogens or pests (Hopkins et al., 2009). The principal
interests in ITCs are due both to their potential role as phytochemicals involved in
inhibiting cancer cell growth (Zhang, 2004) and to the effective action of their biocidal
properties exploited in the biofumigation technique (Gimsing and Kirkegaard, 2009).
More than 30 different GLs are present in Brassica species (Fahey et al., 2001). A
considerable natural polymorphism for the GL type has been found within species
(Agerbirck and Olsen, 2012). The qualitative GL profile is genetically determined and
distinct profiles can characterize genera of Brassicaceae, although plant age, genetic and
environmental factors influence the qualitative and quantitative GL composition (Rosa,
1997). Several cultivated Brassicaceae species, usually classified as oleaginous plants,
have a high seed oil content, generally characterized by a high level of monounsaturated
fatty acids (MFAs) that confer important tribological properties (Moser and Vaughn,
2012) useful for the production of biofuel, biolubricants and lipochemistry molecules. In
Proc. VIth IS on Brassicas and XVIIIth Crucifer Genetics Workshop
Eds.: F. Branca and A. Tribulato
Acta Hort. 1005, ISHS 2013
332
several crops and wild species of the Brassicaceae, variability in the oil composition has
been found (Velasco et al., 1999). Our group has more than 10 years’ experience in
applied research oriented to developing an environmental friendly approach with the goal
of producing bio-based products that are alternatives to conventional chemicals (Lazzeri
et al., 2009). We have collected seeds from wild and cultivated non-food species of the
Brassicaceae family to be evaluated and exploited as a potential source for the formula-
tion of high-value green chemicals. Plants from species selected for their interesting GL
content or fatty acid composition were tested for their adaptability to full-field cultivation.
In the present work we characterized a collection of seeds of 66 non-food Brassicaceae
species for their main GL and major fatty acids.
MATERIALS AND METHODS
The seed samples were provided by germplasm banks or collected from seed
companies. Seeds were cleaned, finely ground and sieved at 0.7μm. They were analyzed
for their GL content according to the EU official ISO 9167-1 method (EEC, 1990), with
some minor modifications. The method is based on the HPLC analysis of desulfo-GLs,
analyzed using an Agilent Model 1100 HPLC system with an Inertsil ODS-3 column (250
x 3 mm, 5 μm), thermostated at 30°C, having a diode array as detector (Lazzeri et al.,
2011). The fatty acid seed content was determined after extraction from ground seed with
hexane and transmethylation in 2N KOH methanolic solution (Conte et al., 1989). Fatty
acid methyl esters were analyzed by a gas chromatography-FID detector (Carlo Erba
HRGC 5300 MEGA SERIES) on a capillary column Restek RTx 2330 (30 m x 0.25 mm x
0.2 μm) with oven temperature programming (initial temperature of 170°C held for 12
min, followed by a gradient of 20°C/min to 240°C, held for 3 min), helium as carrier gas
at 1 ml/min and split mode 40:1. Detector and injector temperature were set at 260°C.
Standards were used for identification of individual fatty acids. The fatty acid composi-
tion was determined by the internal normalization method (ISO 5508, 1998).
RESULTS AND DISCUSSION
Our Brassicaceae collection containing, so far, 66 species characterized for their
main GL and major fatty acid (FA) is reported in Table 1. The collection consists of 50
wild species and 16 species currently cultivated also at agricultural full field level for
different uses.
Glucosinolates (GLs)
The GL analysis of the seed collection makes it possible to distinguish typical GL
profiles, in some cases exclusive to a species, as in Barbarea verna, or common to a
number of different species or different genera as for example in Alliaria petiolata,
Brassica juncea, Brassica carinata, Brassica nigra, Chorispora tenella and Iberis
umbellata. The profiles can be characterized either by a single and predominant GL
(Fig. 1) or by several types of GLs as in Lunaria annua (Fig. 2). As already reported in
Agerbirk et al. (2008), interspecific and intraspecific variation in the profile of the major
seed GL is displayed also in our collection (Table 1). Among the more than 30 different
GLs identified in the seeds, 22 had the highest content and belonged to two of the three
main GL chemical classes (Fahey et al., 2001). Aliphatic GLs are the most numerous and
abundant and they are present in the seeds of 54 species examined, followed by the
aromatic group predominant in 12 species, while the indole GLs are present only in minor
quantities and were never prevalent in the seeds of our collection (Fig. 3). Among the
aliphatic, the thiofunctionalized alkyl GLs, characterized by an additional thio-function –
namely sulfide, sulfoxide or sulfone present in the chain group, are the major GLs in the
seeds of 22 species, followed by the branched or straight chain class containing double
bonds (alkenyl GLs), prevalent in 16 species. The data confirm that these classes are the
largest among the GLs identified till now (Fahey et al., 2001). In Figure 4 we can observe
that gluconapin and sinigrin, belonging to the alkenyl group, are the predominant GLs in
a higher number of species if compared to the other classes of GLs. In particular, most
333
cultivated species, like the entire collection, contain either thio or alkenyl Gls as the major
GLs in the seed. Sinigrin is mostly predominant in a number of cultivated species,
interesting for being exploited for their application in non-food fields, such as B. carinata,
B. juncea and B. nigra.
Fatty Acids (FAs)
Focalizing attention on the most abundant FA present in the seeds, we can observe
(Fig. 5) that 37 species of the collection contain monounsaturated FAs as prevalent in
their seeds, while polyunsaturated FAs are predominant in 29 species. Comparing the
cultivated and wild species it can be highlighted that in 15 of the 16 cultivated species, the
monounsaturated FAs are clearly the main ones (Table 2); in particular, C22:1 is the major
FA in 11 species, with values ranging from 28 to 56%. On the contrary, 27 of the 50 wild
species analyzed mainly contain polyunsaturated FAs as the most abundant in their seeds.
C18:3 is prevalent in 23 wild species with a range from 25 to 55%.
Nevertheless, considering not only the major values but all the FA values
measured in the entire collection, it has to be pointed out that the content of each FA
identified and present in almost all the species examined showed a high variability. C22:1,
for example, showed a range of variability from 1% in Lesquerella fendleri to 56% in
Sinapis alba, while C18:3 varied from 1% in Chorispora tenella up to 55% in Lepidium
ruderale.
CONCLUSIONS
Bio-based raw materials play an increasing role for industrial applications as a
result of the inevitable rising cost of mineral oil and of the increased focus of negative
environmental impacts derived from petrochemicals. Any new industrial application
requires specific biomasses with specific tribological properties, and the high GL and FA
variability in the Brassicaceae is a fundamental starting point for new applications. In
particular, our collection can provide an industrial chain for the production of bio-
lubricants, bio-plastics, biocosmetic, biopesticides, nutraceuticals or molecules for fine
chemicals with the plants most suitable for industry application, selecting those most
adapted for cultivation in a particular area.. The high value-added features are sometimes
present in lesser known species. In this perspective our collection does not aspire to be
representative of the Brassicaceae germplasm, but it could contribute to exploration of
the great potential that the Brassicaceae family can offer to sustainable industry as an
alternative to the dominant species in agriculture.
Literature Cited
Agerbirk, N., Warwick, S.I., Hansen, R.P. and Olsen, C.E. 2008. Sinapis phylogeny and
evolution of glucosinolates and specific nitrile degrading enzymes. Phytochemistry
69:2937-2949.
Agerbirk, N. and Olsen, C.E. 2012. Glucosinolate structures in evolution. Phytochemistry
77:16-45.
Conte, L.S., Leoni, O., Palmieri, S., Capella, P. and Lercker, G. 1989. Half-seed analysis:
rapid chromatographic determination of the main fatty acids of sunflower seed. Plant
Breeding 102:158-165.
EEC Regulation No. 1864/90, Enclosure VIII. 1990. Oil seeds – determination of
glucosinolates. High performance liquid chromatography. Off. J. Eur. Communities,
L170, 27.
Fahey, J.W., Zalcmann, A.T. and Talalay, P. 2001. The chemical diversity and distribution
of glucosinolates and isothiocyanates among plants. Phytochemistry 56:5-51.
Gimsing, A.L. and Kirkegaard, J.A. 2009. Glucosinolates and biofumigation: fate of
glucosinolates and their hydrolysis products in soil. Phytochem. Rev. 8:299-310.
Hopkins, R.J., van Dam, N.M. and van Loon, J.J.A. 2009. Role of glucosinolates in
insect-plant relationships and multitrophic interactions. Annu. Rev. Entomol. 54:57-
83.
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ISO 5508:1998. Animal and vegetable fats and oils – Analysis by gas chromatography of
methyl esters of fatty acids).
Lazzeri, L., Curto, G., Dallavalle, F., D’Avino, L., Malaguti, L., Santi, R. and Patalano, G.
2009. Nematicidal efficacy of biofumigation by defatted Brassicaceae meal for
control of Meloidogyne incognita (Kofoid et White) Chitw on zucchini crop. J.
Sustain. Agr. 33:349-358.
Lazzeri, L., D’Avino, L., Ugolini, L., De Nicola, G.R., Cinti, S., Malaguti, L., Bagatta,
M., Patalano, G. and Leoni, O. 2011. Bio-based products from Brassica carinata A.
Braun oil and defatted meal by a second generation biorefinery approach. Proc. 19th
European Biomass Conference and Exhibition. Berlin, Germany 6-10 June. p.1080-
1092.
Moser, B.R. and Vaughn, S.F. 2012. Efficacy of fatty acid profile as a tool for screening
feedstocks for biodiesel production. Biomass Bioenerg. 37:31-41.
Rosa, E.A.S., Heaney, R.K., Fenwick, G.R. and Portas, C.A.M. 1997. Glucosinolates in
crop plants. Horticultural Reviews 19:99-215.
Velasco, L., Goffman, F.D. and Becker, H.C. 1999. Development of calibration equations
to predict oil content and fatty acid composition in Brassicaceae germplasm by near-
infrared reflectance spectroscopy. JAOCS 76:25-30.
Warwick, S., Francis, A. and Al-Shehbaz, I.A. 2006. Brassicaceae: species checklist and
database on CD-Rom. Plant Syst. Evol. 259:249-258.
Zhang, Y. 2004. Cancer-preventive isothiocyanates: measurements of human exposure
and mechanism of action. Mutat. Res. 555:173-190.
335
Tabl e s
Table 1. List of the wild and cultivated species of the collection, reporting the main GL
and FA for each species.
Botanical name Wild/cultivated Main GL Main FA
A
lliaria petiolata
Arabidopsis thaliana
Barbarea arcuata
Barbarea verna
Barbarea vulgaris
Berteroa incana
Brassica alboglabra
Brassica carinata
Brassica chinensis
Brassica deflexa
Brassica juncea
Brassica maurorum
Brassica napus HE 2
Brassica napus 00 3
Brassica narinosa
Brassica nigra
Brassica rapa
Brassica tournefortii
Bunias orientalis
Camelina microcarpa
Camelina sativa
Capsella bursa-pastoris
Cardamine pentaphylla
Cardaria draba
Cheiranthus cheiri
Chorispora tenella
Conringia orientalis
Coronopus didymus
Crambe abyssinica
C. hispanica hispanica
C. hispanica glabrata
Descurainia pinnata
Descurainia sophia
Diplotaxis tenuifolia
Eruca vesicaria
E. sativa spp. oleifera
Erucastrum
g
allicum
Wil
d
Wild
Wild
Cultivated
Wild
Wild
Wild
Cultivated
Wild
Wild
Cultivated
Wild
Cultivated
Cultivated
Wild
Cultivated
Cultivated
Wild
Wild
Wild
Cultivated
Wild
Wild
Wild
Cultivated
Wild
Wild
Wild
Cultivated
Wild
Wild
Wild
Wild
Wild
Wild
Cultivated
Wil
d
Sinigrin
Glucoerucin
Glucobarbarin
Gluconasturtiin
Glucobarbarin
Glucoberteroin
Gluconapin
Sinigrin
Gluconapin
Glucocheirolin
Sinigrin
Gluconapin
Progoitrin
Progoitrin
Gluconapin
Sinigrin
Gluconapin
Glucoiberin
Sinalbin
Glucocamelinin
Glucocamelinin
Glucoarabin
n.i.4
Sinalbin
Glucocheirolin
Sinigrin
Glucoconringin
Glucotropaeolin
Epiprogoitrin
Epiprogoitrin
Glucoputrangjivin
Gluconapin
Gluconapin
Glucoerucin
Glucoerucin
Glucoerucin
Glucoerucin
C22:1 48 % 1
C18:2 27 %
C22:1 35 %
C22:1 55 %
C22:1 30 %
C18:3 34 %
C22:1 46 %
C22:1 40 %
C22:1 44 %
C22:1 27 %
C22:1 33 %
C22:1 32 %
C22:1 53 %
C18:1 63 %
C22:1 45 %
C22:1 40 %
C22:1 45 %
C22:1 32 %
C18:3 44 %
C18:3 28 %
C18:3 32 %
C18:3 26 %
C22:1 38 %
C18:3 25 %
C22:1 28%
C18:2 43 %
C22:1 27 %
C18:3 44 %
C22:1 54 %
C22:1 52 %
C22:1 42 %
C18:3 39 %
C18:3 43 %
C18:3 25 %
C22:1 36 %
C22:1 47 %
C22:1 45 %
Erysimum officinalis
Hesperis matronalis
Hirschfeldia incana
Iberis amara
Iberis linifolia
Iberis umbellata
Wil
d
Wild
Wild
Cultivated
Wild
Wil
d
Glucoputrangjivin
n.i. 4
Gluconapin
Glucoiberin
Glucoiberin
Sini
g
rin
C18:3 38 %
C18:3 38%
C18:3 30 %
C22:1 42 %
C22:1 43 %
C22:1 53 %
(continued)
336
Table 1. Continued.
Botanical name Wild/cultivated Main GL Main FA
Isatis tinctoria
Lepidium campestre
Lepidium densiflorum
L. virginicum spp. menziesii
Lepidium ruderale
Lepidium sativum
Lesquerella fendleri
Lesquerella grandiflora
Lobularia maritima
Lunaria annua
Lunaria rediviva
Matthiola incana
Orychofragmus violaceus
Raphanus raphanistrum
Raphanus sativus oleiformis
Rapistrum rugosum
Sinapis alba
Sinapis arvensis
Sisymbrium austriacum
S. austriacum spp. contortum
Sisymbrium loeselii
Sisymbrium officinalis
Sisymbrium polyceratum
Trachistoma ballii
Cultivate
d
Wild
Wild
Wild
Wild
Cultivated
Cultivated
Wild
Wild
Wild
Wild
Wild
Wild
Wild
Cultivated
Wild
Cultivated
Wild
Wild
Wild
Wild
Wild
Wild
Wil
d
Gluconapin
Sinalbin
Glucotropeolin
Glucolepidin
Glucotropaeolin
Glucotropaeolin
Glucoiberin
Glucolesquerellin
Gluconapin
Glucoputrangjivin
Glucoalissin
Glucoraphenin
Epiprogoitrin
Glucoraphenin
Glucoraphenin
Glucocheirolin
Sinalbin
Sinalbin
Glucosisimbrin
Glucosisimbrin
Glucosisimbrin
Glucoputrangjivin
Glucosisaustricin
Glucocheirolin
C18:3 28 %
C18:3 36 %
C18:3 49 %
C18:3 50 %
C18:3 55 %
C18:1 30 %
C20:1 OH 51%
n.i 4
C20:1 42 %
C22:1 41 %
C18:2 27 %
C18:3 44 %
C18:2 53 %
C22:1 37 %
C18:1 36 %
C22:1 36 %
C22:1 56 %
C22:1 38 %
C18:3 38 %
C18:3 33 %
C18:3 36 %
C18:3 27 %
C18:3 26 %
C22:1 30 %
1 % of total fatty acids.
2 Brassica napus high erucic acid content.
3 Brassica napus low erucic acid content – high oleic acid content.
4 not identified.
Table 2. Number of cultivated and wild species of our collection in which each fatty acid
listed is the major component and relative range of variation.
Fatty acid
Cultivated species Wild species
Species
FA range
(%)
Species
FA range
(%)
Monounsaturate
d
C18:1 3 30 - 63 0 -
C20:1 0 - 1 42
2
C20:1OH 1 1 51
2--
C22:1 11 28 - 56 22 27 - 52
Polyunsaturate
d
C18:2 0 - 4 27 - 53
C18:3 1 32
223 25 - 55
1 Fatty acid present only in Lesquerella fendleri.
2 Single value, the FA being predominant only in 1 species.
337
Figurese
Fig. 1. Barbarea verna GL profile. Fig. 2. Lunaria annua GL profile.
Fig. 3. Distribution of the major GLs in the species of the collection according to the GL
classification.
338
Fig. 4. Distribution of the single major GL belonging to the different chemical classes in
the seed collection.
Fig. 5. Distribution within the 66 collection species of the major FA present in the oil
composition.
0 2 4 6 8 10 12
GLUCOALYSSIN
GLUCOARABIN
GLUCOCAMELININ
GLUCOBERTEROIN
GLUCOCHEIROLIN
GLUCOERUCIN
GLUCOIBERIN
GLUCORAPHENIN
GLUCOLESQUERELLIN
GLUCONAPIN
SINIGRIN
GLUCOLEPIDIN
GLUCOPUTRANJIVIN
EPIPROGOITRIN
GLUCOCONRINGIN
GLUCOSYSIMBRIN
GLUCOSISAUSTRICIN
PROGOITRIN
GLUCOBARBARIN
GLUCONASTURTIIN
SINALBIN
GLUCOTROPAEOLIN
Glucosinolate type
Number of species
Thiofunctionalised
Alkenyl
Alkyl
HydroxyAlkyl-
HydroxyAlkenyl
Aromatic
0
5
10
15
20
25
30
35
40
Species (N.)
Monounsaturated Polyunsaturated
Major fatty acid
C22:1
C18:1
C20:1OH
C20:1
C18:3
C18:2
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... B. juncea selections were provided by the Brassica seed collection of CREA-CI [42]. They were sown in autumn on 15 October 2017, each in a 30 m 2 plot, at the CREA experimental farm located at Budrio (Bologna) in the Po Valley area (Emilia Romagna region, 44 • 32 00 N; 11 • 29 33 E, altitude 28 m a.s.l.). ...
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