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Characterization of the main glucosinolate content and fatty acid composition in no food Brassicaceae seeds

DOI:10.17660/ActaHortic.2013.1005.38
Authors:
Luca Lazzeri at Council for Agricultural Research and Agricultural Economy Analysis
Luca Lazzeri
Lorena Malaguti at Council for Agricultural Research and Agricultural Economy Analysis
Lorena Malaguti
Manuela Bagatta at Council for Agricultural Research and Agricultural Economy Analysis
Manuela Bagatta
Lorenzo D'Avino at CREA Council for Agricultural Research and Economics
Lorenzo D'Avino
  • CREA Council for Agricultural Research and Economics
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Abstract and Figures

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.
334
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
N°
FA range
(%)
Species
N°
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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... Further informations on the recipes are commercially confidential and their property is of Colussi-Group. E. sativa seeds were from CREA-CI Brassicaceae collection [14] and were defatted by an endless screw press. The E. sativa DSM full characterization was already ...
... Isothiocyanate compounds have a high biocidal activity over a wide range of pests [32][33][34] and pathogens [29,35,36]. Commonly used biofumigant species, such as brown and white mustard, rocket or radishes, contain different GSLs (sometimes a mixture of GSLs), hence produce different ITCs; different cultivars or plant parts may also contain different GSLs quantity or profiles [37,38]. ...
Non-Chemical Soil Fumigation for Sustainable Strawberry Production in Southern Italy
Article
Full-text available
  • Aug 2021
In intensive strawberry production, monoculture is a common practice worldwide; however, prolonged replanting can cause plant disorders and jeopardize profitable cultivation of this highly valuable crop. To mitigate replanting problems, the strawberry industry is still highly dependent on chemical fumigation. Given the increasing regulatory restrictions and concerns about human and environmental risks from fumigants use, there is a growing interest in the adoption of effective, non-chemical alternatives. Two non-chemical soil fumigation practices, i.e., anaerobic soil disinfestation (ASD) and bio-fumigation with biocide plants (BIOFUM), were tested against chemical fumigation by chloropicrin + 1,3-dichloropropene mixture (STANDARD) and untreated (UNTREAT) control in a 2-year trial established in a commercial strawberry farm in Southern Italy (40°25’ N, 16°42′ E). Overall, the alternative practices provided consistently better results than UNTREAT; whereas, compared to STANDARD, their performance was significantly different in the two years: in 2018/19 season the alternative practices registered a 20% (ASD) and 39% (BIOFUM) marketable yield loss compared to STANDARD, while in the 2019/20 season yield differences were not significant. Although both practices appear promising as eco-friendly alternatives to chemical fumigation, in this short-term trial ASD performed better than BIOFUM both in terms of yield and fruit size, resulting in a more advanced stage for practical adoption.
... Crambe VAR. Mario, from CREA-CI Brassicales collection [23], was cultivated in Italy, at the experimental station of CREA-CI located at Budrio (Bologna) in the Po Valley area (44°32′ 00″ N; 11°29′ 33″ E, 28 m above sea level), at an open field level adopting low-input techniques both for energy and for fertilisers, whilst no pesticides were requested. A spring sowing was adopted in March 2017 on a 1600-m −2 experimental plot prepared with a plough and a spring-tooth harrow. ...
Semi-refined Crambe abyssinica (Hochst. EX R.E.Fr.) oil as a biobased hydraulic fluid for agricultural applications
Article
Full-text available
  • Jan 2021
Vegetable oils are well known for their potential applications in green chemistry, including use as hydraulic fluids. Among oilseed crops, Crambe abyssinica Hochst. EX R.E.Fr. gained attention for its low-input requirements during cultivation and for the properties of its oil, characterised by a high erucic acid content. This long-chain mono-unsaturated fatty acid provides appreciable features that make the oil suitable for interesting green chemistry sectors, as biolubricants and cosmetics. In the present work, Crambe oil was tested as a hydraulic fluid for sustainable agricultural applications. Crambe oil was partially refined through phospholipid removal and added with a food-grade antioxidant (tert-butylhydroquinone) at two different concentrations. The fluid efficiency tests were carried out using an experimental test rig, able to simulate a real hydraulic device, performing heavy work cycles at 40-MPa pressure and at 100 °C temperature, with the aim of strongly accelerating the ageing of the tested fluid. At a lower antioxidant concentration, 0.25 g kg⁻¹, the oil underwent a very quick degradation process. However, increasing the additive dose to 2.0 g kg⁻¹, the fluid maintained stable performances. Indeed, all parameters, referred to oil chemical-physical stability and technical performance, were constant along the entire work cycle, up to 290 h. Finally, the present work showed how Crambe seed cultivation, oil extraction and exploitation in the hydraulic circuit of farm machinery could be developed applying green chemistry approaches aiming at small-scale biorefineries linked to the local supply. Graphical abstract
... 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.). ...
Chemical Characterization of Three Accessions of Brassica juncea L. Extracts from Different Plant Tissues
Article
Full-text available
Indian mustard or Brassica juncea (B. juncea) is an oilseed plant used in many types of food (as mustard or IV range salad). It also has non-food uses (e.g., as green manure), and is a good model for phytoremediation of metals and pesticides. In recent years, it gained special attention due to its biological compounds and potential beneficial effects on human health. In this study, different tissues, namely leaves, stems, roots, and flowers of three accessions of B. juncea: ISCI 99 (Sample A), ISCI Top (Sample B), and “Broad-leaf” (Sample C) were analyzed by HPLC-PDA/ESI-MS/MS. Most polyphenols identified were bound to sugars and phenolic acids. Among the three cultivars, Sample A flowers turned were the richest ones, and the most abundant bioactive identified was represented by Isorhamnetin 3,7-diglucoside (683.62 µg/100 mg dry weight (DW) in Sample A, 433.65 µg/100 mg DW in Sample B, and 644.43 µg/100 mg DW in Sample C). In addition, the most complex samples, viz. leaves were analyzed by GC-FID/MS. The major volatile constituents of B. juncea L. leaves extract in the three cultivars were benzenepropanenitrile (34.94% in Sample B, 8.16% in Sample A, 6.24% in Sample C), followed by benzofuranone (8.54% in Sample A, 6.32% in Sample C, 3.64% in Sample B), and phytone (3.77% in Sample B, 2.85% in Sample A, 1.01% in Sample C). The overall evaluation of different tissues from three B. juncea accessions, through chemical analysis of the volatile and non-volatile compounds, can be advantageously taken into consideration for future use as dietary supplements and nutraceuticals in food matrices. Keywords: Brassica juncea spp.; metabolites; foods; volatile; non-volatile; nutraceuticals; HPLC; GC
... Camelina sativa var. Italia was provided by the Brassicaceae seed collection of CREA-CI (Bologna) (Lazzeri et al., 2013). It was sown in autumn on 5 th October 2012, 16 th October 2013, 20 th October 2014, and 30 th September 2015; harvests were accomplished on 7 th June 2013, 29 th May 2014, 4 th June 2015 and 8 th June 2016. ...
Camelina (Camelina sativa L. Crantz) under low-input management systems in northern Italy: yields, chemical characterization and environmental sustainability
Article
Full-text available
  • May 2020
Camelina can be considered a valuable crop for bio-based products and biofuels, but, to date, there are still many uninvestigated aspects concerning the optimization of its agricultural management and its environmental impact. Consequently, a low-input camelina cultivation has been realized, in northern Italy environment, through a 4-year camelina-wheat rotation in open field. In these conditions, camelina was grown as winter crop. Camelina reached, over the years, a variable (CV=28%) mean seed yield of 0.82 Mg ha-1. This notwithstanding, the oil content - 39.17% (CV=3%) - and its related quality were rather stable, reaching an oil yield of 320 kg ha-1 particularly rich in omega-3 fatty acid. The low input cultivation system here adopted implied an energy ratio (output energy/input energy) of 4 and a 30% decrease in Global Warming Potential per hectare, compared to the standard value reported by the European Renewable Energy Directive for sunflower, reducing, at the same time, other relevant environmental burdens. However, due to its relatively low oil production, the full use of all camelina co-products should be considered in order to fulfill the sustainability requirements for European jet fuel production. In fact, stability of yields and quality of oil, oilcake and straws makes low-input camelina eligible for many other novel green chemistry applications.
The Efficacy of Camelina sativa Defatted Seed Meal against Colitis-Induced Persistent Visceral Hypersensitivity: The Relevance of PPAR α Receptor Activation in Pain Relief
Article
Full-text available
  • Jul 2022
Brassicaceae are natural sources of bioactive compounds able to promote gut health. Belonging to this plant family, Camelina sativa is an ancient oil crop rich in glucosinolates, polyunsaturated fatty acids, and antioxidants that is attracting renewed attention for its nutraceutical potential. This work aimed at investigating the therapeutic effects of a defatted seed meal (DSM) of Camelina sativa on the colon damage and the persistent visceral hypersensitivity associated with colitis in rats. Inflammation was induced by the intrarectal injection of 2,4-dinitrobenzenesulfonic acid (DNBS). The acute administration of Camelina sativa DSM (0.1–1 g kg−1) showed a dose-dependent pain-relieving effect in DNBS-treated rats. The efficacy of the meal was slightly enhanced after bioactivation with myrosinase, which increased isothiocyanate availability, and drastically decreased by pre-treating the animals with the selective peroxisome proliferator-activated receptor alpha (PPAR α) receptor antagonist GW6471. Repeated treatments with Camelina sativa DSM (1 g kg−1) meal counteracted the development, as well as the persistence, of visceral hyperalgesia in DNBS-treated animals by reducing the intestinal inflammatory damage and preventing enteric neuron damage. In conclusion, Camelina sativa meal might be employed as a nutraceutical tool to manage persistent abdominal pain in patients and to promote gut healing.
Preserving effect of Loboob (a traditional multi-herbal formulation) on sperm parameters of male rats with busulfan-induced subfertility
Article
Full-text available
  • Jan 2022
Objective: Male infertility secondary to exposure to gonadotoxic agents during reproductive age is a concerning issue. The aim of this experimental study was to determine the effect of Loboob on sperm parameters. Methods: 55 healthy rats were selected, weighted and divided into five groups consisting of 11 rats each. The control group received no medication. Rats in Treatment Group 1 received 10mg/kg Busulfan and rats in Treatment Groups 2, 3, and 4 received 35,70 and 140 mg/kg Loboob respectively in addition to 10mg/kg Busulfan. Finally, the sperm parameters and weights of the rats were compared using the Kolmogorov-Smirnov, non-parametric Kruskal-Wallis, and Dunn-Bonferroni tests. Results: All sperm parameters and weights were significantly decreased among rats receiving Busulfan. All dosages of Loboob were effective to enhance the motility of slow spermatozoa, while only in the rats given 70 and 140 mg/kg of Loboob saw improvements in progressively motile sperm percentages (0.024 and 0.01, respectively). Loboob at a dosage of 140mg/kg improved sperm viability. It did not improve normal morphology sperm or decrease immotile sperm counts. Loboob did not affect mean rat weight. Conclusions: Loboob offered a dose-dependent protective effect on several sperm parameters in rats with busulfan-induced subfertility.
Eruca sativa Mill. seed extract promotes anti-obesity and hypoglycemic effects in mice fed with a high-fat diet
Article
Obesity is currently considered a major source of morbidity, with dramatic complications on health status and life expectancy. Several studies demonstrated the positive effects of Brassicaceae vegetables on obesity and related diseases, partially attributing these beneficial properties to glucosinolates and their derivatives isothiocyanates. Recently, isothiocyanates have been described as a hydrogen sulfide (H2S)-releasing moiety, suggesting that H2S may be at least in part responsible for the beneficial effects of Brassicaceae. In this work, the metabolic effects of an extract obtained from Eruca sativa Mill. seeds (E.S., Brassicaceae), containing high levels of glucoerucin, were evaluated in an experimental model of obesity. Male balb/c mice were fed for 10 weeks with standard (Std) diet or high fat (HF) diet supplemented with E.S. E.S. significantly contained the body weight gain in this obesity model, improving also glucose homeostasis. Interestingly, lower values of white adipose tissue mass and a significant reduction of adipocytes size were also observed. Moreover, E.S. enhanced the adipocytes metabolism, improving the citrate synthase activity and reduced triglyceride levels in mice fed with HF diet. Taken together, these results suggest that E.S. is endowed with an interesting translational and nutraceutical value in the prevention of metabolic disorders, suggesting that H2S could be a key player.
Nematicidal Efficacy of Biofumigation by Defatted Brassicaceae Meal for Control of Meloidogyne incognita (Kofoid et White) Chitw. on a Full Field Zucchini Crop
Article
Full-text available
  • Apr 2009
The use of Brassicaceae biocidal green manure crops (e.g., Raphanus sativus ssp oleiformis and Eruca sativa ssp oleiformis) is an agronomic technique for the control of several nematodes including Heterodera schachtii and Meloidogyne incognita. Recently, these crops have been extensively studied and even commercially applied in horticulture rotations. In addition, the possibility of producing a formulation based on Brassicaceae defatted seed meals characterized by biocidal activity has been developed. These meals are able to amend soils with organic matter containing nematicidal volatile compounds, derived from the enzymatic hydrolysis of endogenous glucosinolates. This option opens new perspectives for an organic and low environmental impact nematode control. In this study, the effect of a treatment with industrial defatted meals on a commercial zucchini cultivation in greenhouse, on sandy soil heavily and uniformly infested by root-knot nematode Meloidogyne incognita was evaluated. This effect was compared with the effectiveness of six liquid applications during zucchini crop using Oxamyl distributed by drip irrigation, a technique allowed, recommended and commercially applied on zucchini in the area where the experiment was conducted. During harvesting time, the nematode level both in roots and in soil, and some qualitative (length, weight and diameter) and quantitative (yield) zucchini parameters were evaluated. Compared with the chemical control, defatted seed meal application clearly limited nematode infestation and allowed plant roots with a lower root gall index (2.0 to 3.5 versus 3.5 to 4.5). The zucchini yield in biocidal seed meal treated plot was the same as the control in the first month of harvesting, but it was 9% higher in the second month of harvesting due to the lower infestation of zucchini roots. In addition, in the plot treated with defatted seed meal, harvesting time was one week longer than chemical plot with a final 14% total yield improvement.
Development of Calibration Equations to Predict Oil Content and Fatty Acid Composition in Brassicaceae Germplasm by Near-Infrared Reflectance Spectroscopy
Data
Full-text available
  • Jan 1999
The use of nondestructive analytical methods is critical for the evaluation of very small seed samples such as those from germplasm collections. The objective of this study was to evaluate the potential of near-infrared reflectance spectroscopy (NIRS) for the simultaneous analysis of seed oil content and concentration of major fatty acids in intact-seed samples of the family Brassicaceae. A total of 495 samples from 56 genera and 128 species were analyzed by NIRS. The fatty acid composition of the seed oil was determined in all the samples by gas-liquid chromatography (GLC). The total seed oil content was determined by solvent extraction in 129 samples from 22 genera. Calibration equations for oil content (n = 97) and individual fatty acids (n = 410) were developed and tested through external validation with the samples not included in the calibration sets. The calibration equations for oil content (r2 = 0.97 in validation) and concentrations of C18:1 (r2 = 0.93), C18:3 (r2 = 0.95), and C22:1 (r2 = 0.94) showed very good performance and provided reliable estimations of these traits in the samples of the validation set. The calibration equations for C16:0, C18:0, and C18:2 content were less reliable, with r2 from 0.67 to 0.73. There was practically no response of NIRS to differences in C20:1 (r2 = 0.31). These results demonstrated that the oil content and concentrations of C18:1, C18:3, and C22:1 can be estimated reliably within the family Brassicaceae by using NIRS calibration equations integrating broad taxonomic variability.
Development of calibration equations to predict oil content and fatty acid composition in Brassicaceae germplasm by near-infrared reflectance spectroscopy
Article
Full-text available
  • Sep 1999
The use of nondestructive analytical methods is critical for the evaluation of very small seed samples such as those from germplasm collections. The objective of this study was to evaluate the potential of near-infrared reflectance spectroscopy (NIRS) for the simultaneous analysis of seed oil content and concentration of major fatty acids in intact-seed samples of the family Brassicaceae. A total of 495 samples from 56 genera and 128 species were analyzed by NIRS. The fatty acid composition of the seed oil was determined in all the samples by gas-liquid chromatography (GLC). The total seed oil content was determined by solvent extraction in 129 samples from 22 genera. Calibration equations for oil content (n=97) and individual fatty acids (n=410) were developed and tested through external validation with the samples not included in the calibration sets. The calibration equations for oil content (r 2=0.97 in validation) and concentrations of C18:1 (r 2=0.93), C18:3 (r 2=0.95), and C22:1 (r 2=0.94) showed very good performance and provided reliable estimations of these traits in the samples of the validation set. The calibration equations for C16:0, C18:0, and C18:2 content were less reliable, with r 2 from 0.67 to 0.73. There was practically no response of NIRS to differences in C20:1 (r 2=0.31). These results demonstrated that the oil content and concentrations of C18:1, C18:3, and C22:1 can be estimated reliably within the family Brassicaceae by using NIRS calibration equations integrating broad taxonomic variability.
Brassicaceae: Species checklist and database on CD-Rom
Article
Full-text available
  • Jul 2006
A species checklist has been prepared for the Brassicaceae (Cruciferae) family, providing the first updated list in over 70 years. The family, currently, includes 338 genera and 3709 species. The database contains approximately 14,000 taxonomic names (records). Taxon status and synonymy, taxon name, scientific authority, literature source and source verification, and the basionym are provided for each record.
Efficacy of fatty acid profile as a tool for screening feedstocks for biodiesel production
Article
Fuel properties are largely dependent on the fatty acid (FA) composition of the feedstock from which biodiesel is prepared. Consequently, FA profile was employed as a screening tool for selection of feedstocks high in monounsaturated FAs for further evaluation as biodiesel. Those feedstocks included ailanthus (Ailanthus altissima L.), anise (Pimpinella anisum L.), arugula (Eruca vesicaria L.), cress (Lepidium sativum L.), cumin (Cuminum cyminum L.), Indian cress (Tropaeolum majus L.), shepherd’s purse (Capsella bursa-pastoris L.) and upland cress (Barbarea verna (Mill.) Asch.). Other selection criteria included saturated FA content, iodine value (IV), content of FAs containing twenty or more carbons and content of trienoic FAs. Anise oil satisfied all selection criteria and was therefore selected for further investigation. Arugula, cumin and upland cress oils were selected as antagonists to the selection criteria. Preparation of FA methyl esters (FAMEs, ≥ 92 wt % yield) following conventional alkaline-catalyzed methanolysis preceded fuel property determination. Of particular interest were oxidative stability and cold flow properties. Also measured were kinematic viscosity (40 °C), IV, acid value, free and total glycerol content, sulfur and phosphorous content, cetane number, energy content and lubricity. FAMEs prepared from anise oil yielded properties compliant with biodiesel standards ASTM D6751 and EN 14214 whereas the antagonists failed at least one specification contained within the standards. As a result, FA profile was an efficient predictor of compliance with biodiesel standards and is therefore recommended as a screening tool for investigation of alternative feedstocks.
Half-Seed Analysis: Rapid Chromatographic Determination of the Main Fatty Acids of Sunflower Seed
Article
The halt-seed technique, with some recent modifications of traditional analytic methods, is proposed for selecting sunflower with modified fatty acid composition. A rapid method was used for extracting the oil and for methylating the fatty acids (about 3 min per sample). Thin-layer chromatography (TLC) plates activated with AgNO3, and/or gas chromatography (GLC) with capillary columns were used to analyse the methylated esters. Half-seed, whole-seed and meal analysts of sunflower and other oilseed species confirmed the validity of the method with regard to sampling, analytic result and embryo germinability. In addition, GLC using a suitable internal standard can be used to evaluate the percentage oil content of the seed. About ten samples per hour can be analyzed with GLC versus 20—25 with TLC. These times can be further shortened in practice in the laboratory by partially overlapping some steps.
Sinapis phylogeny and evolution of glucosinolates and specific nitrile degrading enzymes
Article
Levels of sinalbin (4-hydroxybenzylglucosinolate) and 28 other glucosinolates were determined in leaves and roots of 20 species that were either phylogenetically close to Sinapis alba, Sinapis arvensis, or Sinapis pubescens (tribe Brassiceae, Brassicaceae), or were expected to contain arylalkyl nitrilase activity. Comparison with a molecular phylogenetic tree based on ITS DNA sequences identified two separate occurrences of sinalbin. The first in a group of species related to S. alba (including members of the genera Coincya and Kremeriella); and the second in S. arvensis, nested among sinalbin deficient species. Significant 4-hydroxyphenylacetonitrile degrading enzyme activity was found in both S. alba and S. arvensis, but in S. alba the major product was the corresponding carboxylic acid, while in S. arvensis the major product was the amide. Both investigated enzyme activities, nitrilase and nitrile hydratase, were specific, accepting only certain arylacetonitriles such as 4-hydroxy and 4-methoxyphenylacetonitrile. Only the S. alba enzyme required an oxygen in para position of the substrate, as found in sinalbin. Indole-3-acetonitrile, arylcyanides, and arylpropionitriles were poor substrates. The nitrilase activity of S. alba was quantitatively comparable to that reported in the monocot Sorghum bicolor (believed to be involved in cyanogenic glycoside metabolism). Glucosinolates derived from methionine were found in all Sinapis clades. Glucosinolate patterns suggested a complex evolution of glucosinolates in the investigated species, with several apparent examples of abrupt changes in glucosinolate profiles including chain length variation and appearance of glucosinolates derived from branched-chain amino acids. NMR data for desulfated homosinalbin, 9-methylsulphonylnonylglucosinolate, 3-methylpentylglucosinolate and related glucosinolates are reported, and a facultative connection between sinalbin and specific nitrilases is suggested.
Cancer-preventive isothiocyanates: Measurement of human exposure and mechanism of action
Article
Numerous studies in rodents have documented the cancer-preventive activity of a significant number of isothiocyanates (ITCs), the majority of which occur in plants, especially in cruciferous vegetables. Dietary ITCs may play an important role in the prevention of human cancers. Several recent epidemiological studies have already shown that dietary consumption of ITCs inversely correlates with the risk of developing lung, breast and colon cancers. ITCs are principally metabolized through the mercapturic acid pathway in vivo, giving rise to N-acetylcysteine conjugates, which are excreted in the urine. Analytical methods have been developed to allow detection of ITCs and their metabolites formed in the mercapturic acid pathway. Studies show that total urinary level of ITC equivalent is an excellent biomarker of human exposure to ITCs. Moreover, these methods also have made it possible to learn the bioavailability of ITCs from cruciferous vegetables. ITCs possess multiple anticarcinogenic mechanisms, including inhibition of carcinogen-activating enzymes, induction of carcinogen-detoxifying enzymes, increase of apoptosis, arrest of cell cycle progression, as well as several other mechanisms that are not yet fully described. These mechanisms, which are discussed in detail in this review, illustrate the remarkable ability of ITCs to inhibit cancer development-effective against both developing and developed cancer cells.