chemical composition of the potential new oilseed cropsbarbarea vulgaris,barbarea verna andlepidium...

Journal of Science of Food and Agriculture J Sci Food Agric 79 :179–186 (1999)

Chemical composition of the potential newoilseed cropsBarbarea vulgaris,Barbareaverna andLepidium campestreAnnica AM Anders s on,1* Arnulf Merker,2 Peter Nils s on,2 Hilmer SÔrens en3

and Per A� man11 Department of Food Science, Swedis h Univers ity of Agricultural Sciences , PO Box 7051, S-750 07 Upps ala, Sweden

2 Department of Plant Breeding Res earch, Swedis h Univers ity of Agricultural Sciences , S-268 31 SwedenSvalo� v,3 Chemis try Department , Royal Veterinary and Agricultural Univers ity , 40 , Thorvalds ens vej , DK-1871 Frederiks berg C,Copenhagen,

Denmark

Abstract : Barbarea vulgaris, Barbarea verna and Lepidium campestre were selected as potential new

oilseed crops. To evaluate the nutritional and technological quality of the seeds, the chemical com-

position was studied. The major constituents found were dietary übre, crude fat and crude protein.

Barbarea contained about 350 g kg—1 dietary übre, 295 g kg—1 crude fat and 170 g kg—1 crude protein,

while Lepidium contained about 400 g kg—1 dietary übre, 200 g kg—1 crude fat and 190 g kg—1 protein.

The amino acid composition was found to be suitable for human consumption when comparison with

the amino acid pattern for high quality protein was made. Fatty acid composition was dominated by

erucic acid in B vulgaris (28%) and B verna (50%) and by linolenic acid in L campestre (34%). Insolu-

ble dietary übres were dominated by Klason lignin in both Barbarea and Lepidium. Uronic acid and

glucose residues were also found in large amounts. Soluble dietary übres were dominated by uronic

acid, arabinose and galactose residues. The major glucosinolates found were glucobarbarin in B vul-

garis (108 lmol g—1), gluconasturtiin in B verna (106 lmol g—1) and sinalbin in L campestre

(110 lmol g—1). No cyanogens were found in any of the seeds.

1999 Society of Chemical Industry(

Keywords: oilseed crops ; Barbarea; Lepidium; chemical composition.

INTRODUCTION

Recently, a plant-breeding programme was startedwith the aim of creating new oilseed crops by domes-ticating wild species of Barbarea and Lepidium.1Since there is a natural variation among individuals,the problems with small seeds, strong seed dormancyand weak shattering resistance could be solved byselection for genotypes with advantageous character-istics. The agronomical advantages of Barbarea vul-garis are its perennial nature, excellent winterhardiness and high seed yields. The advantages ofBarbarea verna and Lepidium campestre are the same,except that they are biennial and that B verna alsohas larger seeds, weaker seed dormancy, more evenmaturation and less good winter hardiness.

There are several reasons for creating new oilcrops. One is overproduction of food crops inmodern agriculture, where new crops for industrialraw material, for example new oil crops, could be asolution to the problem.2,3 Another reason is theserious environmental problem with leaching ofnutrients, especially nitrogen. New oil crops could be

used as catch crops which cover the üelds during thewinter and accumulate nitrogen.4 Furthermore, theycould also be used as alternative crops for productionof fuel and chemotechnical raw material. Finally,when introducing new genes into an oil crop for thepurpose of producing technical oil, it is importantthat the seeds with the new oil quality can be distin-guished from other common food oil seeds. Theseeds could otherwise be mixed up during handlingof them and problems with cross-fertilisation couldoccur.

A few studies concerning the chemical composi-tion of the seeds of B vulgaris and L campestre havebeen reported. Appelqvist2 investigated the fatty acidcomposition of B vulgaris, and studied theSÔrensen5structures of glucosinolates in B vulgaris and L cam-pestre. There is however no broad investigation ofthe chemical composition of the seeds. The aim ofthis work was thus to determine the variation inchemical composition of some seed samples of Bvulgaris, B verna and L campestre. This basicinformation is necessary for the evaluation of

* Corres pondence to : Annica AM Anders s on, Department of

Food Science, Swedis h Univers ity of Agricultural Sciences , PO

Box 7051, S-750 07 Upps ala, Sweden

(Received 3 July 1997; revis ed vers ion received 27 November

1997; accepted 14 April 1998)

( 1999 Society of Chemical Industry. J Sci Food Agric 0022–5142/99/$17.50 179

AAM Andersson et al

nutrient and technological quality of the potentialnew oil crops.

MATERIAL AND METHODS

Material

The seeds analysed came from a yield trial in 1994.Collected material of the three species B vulgaris, Bverna and L campestre, was cultivated for two gener-ations in üeld trials in 1992 and 1994.1 The üeldswere situated at Ultuna, just south of Uppsala inSweden. Five of the highest yielding accessions ofeach species in the 1992 trial were chosen for the1994 trial. Their geographical origin is shown inTable 1. No breeding work was done on thismaterial. Selection was made for entire accessions.The 1994 trial was sown by machine in June 1993and fertilised in May 1994 with 40kg N ha~1. Har-vesting occurred in August 1994 by hand to mini-mise losses from shattering. The seeds were driedand stored at 10–15¡C until analysis. Before analysisthe seeds were cleaned in a sieve with openings of1] 1mm for B vulgaris, 1.5] 1.5mm for B vernaand 2] 2mm for L campestre.

Methods

Prior to analysis representative seed samples (10g)were ground in a coþee-type mill (Janke and Kunkel,IKA-WERK, Germany), to a particle size of lessthan 0.5mm. All analyses were performed in dupli-cate and are reported on a dry matter basis. The drymatter content was determined by oven-drying at105¡C for 5h. Starch was determined enzymically,6while ash and crude protein (N ] 6.25) wereanalysed according to standard methods.7 Crude fatwas extracted with light petroleum (bp 40–60¡C) in aTecator Soxtec System HT (Tecator AB, Sweden)after acid hydrolysis with 3M HCl.8

The samples were extracted twice with hexane/2-propanol (3 : 2v/v) (50ml g~1 sample), three timeswith 80% ethanol (75ml g~1 sample) and twice withacetone (50ml g~1 sample) in order to remove lipo-philic compounds and low-molecular-weight carbo-hydrates.9 Dietary übre, deüned as the sum ofnon-starch polysaccharide residues, amylase-resistant starch and Klason lignin, was analysed inthese samples essentially according to the AOACprocedure by Theander et al,10 but with some modi-ücations in order to separate soluble and insoluble

dietary übres. After incubation of the samples witha-amylase and amyloglucosidase in 15ml acetatebuþer, the tube was cooled and centrifuged. Thepellet, which contains insoluble übre, was washedwith 5ml buþer, followed by another centrifugation.The supernatants, which contain soluble übre, werecombined and diluted to 25ml in a volumetric ýask,of which 5ml was transferred to a new tube. Solubleübre was precipitated by addition of ethanol as in theAOAC procedure. Hydrolysis of soluble übre wascarried out on a scale of 1 : 10 of the original pro-cedure. The swelling in 12M was omittedH2SO4since no cellulose was present in this fraction. Thepellet containing insoluble übre was treated as in theAOAC procedure. Derivatisation, determination ofneutral sugars as alditol acetates by GC and determi-nation of uronic acids was performed according tothe AOAC procedure for both the insoluble andsoluble fraction.

The seeds (400mg) were homogenised in 5mllight petroleum (bp 85–95¡C) and 2ml of the homog-enisate was extracted with 6ml 0.02M methanolicsodium methoxide in a waterbath for 30min at 50¡C.After addition of 5ml 6% NaCl the ether phase wastaken for analysis of fatty acids by GC.11 Afterhydrolysis with 6N HCl, amino acids were analysedwith ion-exchange chromatography.12

Quantitative solid-state detection of cyanogens inthe seeds was carried out as described by Brimer.13Glucosinolates were analysed as intact glucosinolatesand desulphoglucosinolates, by using both HPLCand micellar electrokinetic capillary chromatog-raphy.5,14,15 Aromatic choline esters were analysedaccording to Bjergegaard et al16 using micellar elec-trokinetic capillary chromatography.

RESULTS AND DISCUSSION

The variation in gross chemical composition of theüve samples of B vulgaris, B verna and L campestre,respectively, is shown in Table 2. The major constit-uents found were dietary übre, crude fat and crudeprotein, which together constituted about 810g kg~1of the dry matter. The content of dietary übre washighest in L campestre with 414g kg~1, while thecontent in B vulgaris and B verna was about350g kg~1. The average content of crude fat wasabout 295g kg~1 in B vulgaris and B verna, and

Barbarea vulgaris Barbarea verna Lepidium campes tre

Fa- rhult, Sweden Belgium Arild, Sweden

Salzburg, Aus tria Go� ttingen, Germany O� land, SwedenOldenburg, Germany Belgium Gothenburg, Sweden

Oldenburg, Germany Bris tol, England Budapes t, Hungary

Oldenburg, Germany Freiburg, Germany Kris tians tad, Sweden

Table 1. Geographical origin of

s eeds of Barbarea vulgaris ,

Barbarea verna andLepidium

campes tre

180 J Sci Food Agric 79 :179–186 (1999)

Chemical composition of Barbarea vulgaris, B verna and Lepidium campestre

Table 2. Variation in chemical compos ition (g kg~1 dry matter) of collected s eeds of Barbarea vulgaris , Barbarea verna andLepidiumcampes tre

Cons tituent Barbarea vulgaris (n\ 5) Barbarea verna (n\ 5) Lepidium campes tre (n\ 5)

Mean Range CV(%) Mean Range CV(%) Mean Range CV(%)

Starch traces a traces a traces aCrude protein 172 165–178 3.2 170 167–174 1.6 191 175–202 5.3

Crude fat 294 282–311 4.4 295 288–301 1.9 204 189–211 4.3

As h 59 54–65 8.6 59 54–63 6.0 68 66–70 2.0

Dietary fibre 347 336–351 1.8 350 329–368 4.7 414 393–442 5.6

Total 872 865–881 0.9 874 862–904 1.8 877 849–899 2.4

a traces \5 g kg~1.

204g kg~1 in L campestre. The protein content washigher in L campestre (191g kg~1), than it was in Bvulgaris and B verna (about 170g kg~1). The meancontent of ash was 59g kg~1 in both the Barbareaspecies, while it was 68g kg~1 in L campestre. Starchwas only found in very small amounts (\5g kg~1).The coefficient of variation (CV) was \9% for allconstituents in all three species.

The chemical composition of rapeseed, which is acommonly grown oilseed crop, is 400–500g kg~1 oil,250g kg~1 protein, 180g kg~1 dietary übre and40g kg~1 ash.17 In comparison, Barbarea and Lepi-dium have a lower content of oil and protein, and ahigher content of ash and dietary übre. Oil andprotein are the desirable constituents of an oil crop,and the content of them in Barbarea and Lepidium

has to be increased to obtain a more satisfactoryproduct. Defatted rapeseeds have been reported tocontain 90–150g kg~1 low-molecular-weight sugars,including traces of starch.18 Low-molecular-weightcarbohydrates, together with glucosinolates, areprobably also the main components of the non-analysed part of Barbarea and Lepidium.

The main amino acids in B vulgaris and B vernawere glutamic acid and aspartic acid, which also werethe main ones in L campestre, together with arginine(Table 3). The CV was less than 10% for all aminoacids, except for proline (in B vulgaris and Lcampestre) and for threonine (in L campestre), whichwere somewhat higher. All the essential amino acidswere found in relatively high amounts in all threespecies. Rapeseed is known to have a very good

Table 3. Amino acid compos ition (g kgÉ1 protein) in collected s eeds of Barbarea vulgaris , Barbarea verna andLepidium campes tre



Cys tine 20 17–21 8.5 19 18–19 2.9 25 22–26 6.8

Methionine 16 15–17 6.2 16 16–17 2.8 12 11–14 9.2

As partic acid 79 75–82 3.4 81 78–84 3.2 71 66–76 6.7

Threonine 43 40–45 4.6 44 43–45 2.5 34 30–38 10.0

Serine 43 39–44 4.9 40 39–41 2.5 39 35–43 8.6

Glutamic acid 139 133–142 2.5 131 129–134 1.7 130 119–139 5.8

Proline 52 48–61 10.1 52 49–56 5.3 57 48–66 14.2

Glycine 54 52–55 2.1 53 53–54 1.0 49 47–53 6.2

Alanine 42 41–44 2.7 40 39–40 1.4 40 38–43 4.8

Valine 50 49–51 1.8 47 47–48 1.2 47 45–48 2.9

Is oleucine 40 39–40 1.1 39 38–40 2.2 38 37–40 4.3

Leucine 66 65–67 1.1 66 65–68 1.7 57 55–59 2.9

Tyros ine 35 33–36 3.3 34 33–35 2.6 31 29–33 5.1

Phenylalanine 41 40–42 1.7 38 38–39 1.4 40 39–42 3.8

His tidine 25 24–26 3.4 24 23–24 2.3 29 28–30 2.9

Lys ine 55 53–55 1.6 52 51–54 2.2 63 60–65 3.7

Arginine 60 58–61 2.0 57 56–58 1.5 76 72–79 4.4

Ammonia 13 12–14 7.1 13 13–13 0.0 15 14–16 5.7

Total 871 849–882 8.7 848 838–863 1.3 853 800–907 11.1

J Sci Food Agric 79 :179–186 (1999) 181

AAM Andersson et al

Table 4. Fatty acid compos ition (relative%) in collected s eeds of Barbarea vulgaris , Barbarea verna andLepidium campes tre



C16 : 0] 1 2.8 2.6–2.9 4.7 3.1 3.0–3.2 2.9 4.8 4.4–5.2 6.7

C18 : 0 0.5 0.4–0.5 9.3 0.3 0.3–0.4 14.0 1.1 1.0–1.3 10.0

C18 : 1 23.1 22.2–23.7 2.6 14.7 13.1–20.2 21.1 15.2 14.7–16.0 3.7

C18 : 2 20.5 19.9–21.2 2.5 14.7 14.2–16.1 5.4 9.9 9.4–10.6 4.5

C18 : 3 9.6 9.1–10.0 3.6 5.2 5.0–5.6 4.2 34.1 33.6–34.8 1.4

C20 : 0 0.4 0.3–0.4 15.2 0.4 0.4–0.4 0.0 0.6 0.6–0.7 8.6

C20 : 1 10.9 10.7–11.1 1.5 7.5 7.1–8.7 9.2 5.6 5.2–6.0 5.1

C20 : 2 0.8 0.7–0.8 5.7 0.7 0.6–0.7 6.6 0.5 0.5–0.6 10.1

C22 : 0 NDa 0.2 0.2–0.3 22.8 1.4 1.3–1.6 8.7

C22 : 1 28.3 27.0–28.9 2.6 49.4 42.3–51.5 8.1 22.7 21.6–24.1 4.0

C22 : 2 0.3 0.3–0.3 0.0 0.7 0.4–0.8 24.8 0.3 0.3–0.3 0.0

C24 : 0 ND ND 0.7 0.6–0.7 6.6

C24 : 1 2.4 2.2–2.6 6.9 2.6 2.3–2.9 10.2 2.1 2.0–2.2 4.0

a ND, not detected.

amino acid composition according to the referencepattern for the content of amino acids for humans.19Compared to rapeseed,20 Barbarea and Lepidiumhave a higher content of cysteine ] methionine, anequal content of threonine and tyrosine ]phenylalanine and a somewhat lower content ofvaline, isoleucine, leucine, histidine and lysine. Thecontent of histidine and lysine is, however, higherthan in the reference pattern for amino acid composi-tion and the content of valine is similar. Thus, Barb-area and Lepidium have an amino acid compositionsuitable for humans.

Erucic acid was the most abundant fatty acid inBarbarea, especially in B verna where it constitutedalmost 50% of the oil content (Table 4). The othermain fatty acids in Barbarea were oleic acid and lin-oleic acid. In Lepidium the main fatty acid was lin-olenic acid, followed by erucic acid and oleic acid.CV were low for most fatty acids, except for oleicacid in B verna, and for some fatty acids present invery low amount. Compared to erucic free rapeseedoil,21 the oil in Barbarea had a lower content of oleicacid, almost the same content of linoleic and linolenicacid and, of course, a higher content of erucic acid.The oil in L campestre had a lower content of oleicand linoleic acid, a higher content of linolenic acidand, also of course, a higher content of erucic acid. Ifthe oil is going to be used in food or feed, the erucicacid has to be removed by plant breeding, as it hasbeen in double low rapeseed varieties. However, intechnological oils as for example in a lubricant ingear boxes, erucic acid is advantageous due to its tol-erance of high temperatures.22 The high content oflinolenic acid in L campestre could be advantageous ifusing the oil in, for example, paints, because it givesan oil which rapidly oxidises.

The content and composition of soluble and insol-uble dietary übres are presented in Table 5. Insolu-

ble dietary übre dominated and it consisted mainlyof Klason lignin, a phenolic constituent mostly foundin the husk of seeds, as shown, for example, inrapeseed.17,21 Uronic acid and glucose residues werealso found in large amounts in the insoluble dietaryübres. Klason lignin, uronic acid and glucose resi-dues are known to be dominating constituents of thedietary übres also present in rapeseed, where themajority are found in the husk.17 Glucose residuesprobably originate from cellulose and xyloglucans.Other major residues were arabinose and galactose,which are also important residues in rapeseed dietaryübres.17 These components, together with uronicacid residues were dominating in the soluble dietaryübre fraction and probably originate from pecticsubstances. In Lepidium there was twice as muchsoluble dietary übre (21g kg~1) as in Barbarea(10g kg~1). The content of arabinose residues wasabout the same as in Barbarea, but a much highercontent of uronic acid and galactose residues waspresent. When seeds of Lepidium were soaked inwater a large transparent gel was formed surround-ing the whole seed. The gel could be a poly-saccharide gel containing soluble dietary übres. Inlinseed a similar gel forms, which consists mainly ofuronic acids and arabinoxylan.23 The variation incontent of soluble dietary übre polysaccharide resi-dues was large, due to the very small amounts ofthese components. Insoluble dietary übre poly-saccharides had CV generally less than 10%.

The major glucosinolates found diþered betweenthe three species (Fig. 1, Tables 6 and 7). In B vul-garis glucobarbarin was the quantitatively pre-dominant component (108lmol g~1 seed) whileglucosibarin, which is an epimer of glucobarbarin,was found only in small amounts. In Barbarea inter-media it was shown that the content of glucosibarinwas higher than the content of glucobarbarin (result

182 J Sci Food Agric 79 :179–186 (1999)


Table 5. Content of s oluble and ins oluble dietary fibre cons tituents (g kgÉ1 dry matter) in collected s eeds of Barbarea vulgaris , Barbarea

verna andLepidium campes tre



Soluble

Rhamnos e 0.6 0.3–1.1 58.7 0.5 0.5–0.6 7.7 1.5 1.2–1.8 13.0

Fucos e traces a traces traces

Arabinos e 2.3 1.9–2.8 13.4 1.7 1.5–2.0 11.9 2.2 1.9–2.3 7.9

Xylos e 0.9 0.8–1.1 14.9 0.6 0.5–0.7 15.6 0.7 0.6–0.8 12.2

Mannos e 0.3 0.2–0.3 10.6 0.2 0.2–0.3 21.9 0.4 0.3–0.4 10.8

Galactos e 1.3 1.2–1.5 8.0 1.1 0.9–1.2 7.8 3.4 3.1–3.8 9.5

Glucos e 0.7 0.6–0.7 5.6 0.4 0.3–0.5 14.7 0.6 0.5–0.7 8.4

Uronic acids 4.0 2.8–6.3 34.3 5.1 4.7–5.6 7.4 11.9 11.1–12.9 5.8

Total 10.2 2.9–7.8 19.4 9.7 9.1–10.9 7.9 20.7 19.3–22.3 5.3

Ins oluble

Rhamnos e 7.5 7.3–7.7 2.5 6.4 6.0–6.8 5.0 11.1 10.4–11.8 5.2

Fucos e 0.9 0.8–1.0 7.4 0.6 0.5–0.7 13.1 0.9 0.8–1.0 12.1

Arabinos e 24.2 23.1–25.3 3.3 24.7 22.6–26.7 7.0 25.2 23.0–27.1 6.8

Xylos e 11.3 10.5–11.9 5.1 9.4 8.6–10.2 7.5 10.8 10.2–11.9 7.0

Mannos e 4.0 3.9–4.1 1.8 4.2 4.0–4.3 3.0 4.2 3.9–4.6 6.8

Galactos e 13.7 12.8–14.4 4.5 11.4 0.7–12.0 4.9 21.5 17.5–24.1 11.7

Glucos e 42.1 41.1–43.2 2.1 50.5 49.0–52.0 2.5 84.8 81.5–89.8 3.6

Uronic acid 52.7 47.3–55.4 6.0 69.4 61.9–74.3 6.9 113 111–117 2.1

Klas on lignin 181 172–189 3.7 164 153–173 5.6 122 106–156 17.4

Total 337 326–341 1.8 341 320–357 4.6 393 372–420 5.7

a traces \ 0.05 g kgÉ1.

not shown). There was a large variation in thecontent of glucosibarin in B vulgaris, essentially dueto the fact that one of the samples, originating fromOldenburg, Germany, had a much higher contentthan the others. In B verna neither glucobarbarinnor glucosibarin was found. The major glucosinolatefound was instead gluconasturtiin (106lmol g~1).The major glucosinolate found in L campestre wassinalbin (110lmol g~1). Other glucosinolates foundin B vulgaris were glucobarbarin esteriüed with iso-ferulic acid at C2, C6 or both C2 and C6 of theglucose residues. These isoferuloyl glucosinolateswere also found in B intermedia (results not shown).B verna and L campestre did not contain any iso-feruloyl derivatives.

Glucosinolates, as well as their degradation pro-ducts, have been shown to cause antinutritionaland/or toxic eþects in animals.5 If the oil seed mealfrom these crops is to be used as human food or feed,glucosinolate levels have to be reduced to a low levelby plant breeding, as have been achieved in double

Figure 1. General s tructure of glucos inolates . R\ s ide chainaccording to Table 7. and or acyl derivative accordingR

2R

6\H

to Table 7.

low rapeseed. Alternatively, they have to be isolatedduring processing, as is now possible by aqueousenzymatic processing.24 Earlier varieties of rapeseedcontained high amounts of glucosinolates. Contentsof between 60 and 150lmol g~1 have been reportedfor diþerent rapeseed varieties.20,21 The content ofglucosinolates in Barbarea and Lepidium was 123–138lmol g~1. New varieties of rapeseed have acontent of less than 30lmol g~1 (Ref. 25) or to be adouble low variety in EU the level need to be below18lmol g~1. The major glucosinolates reported inrapeseed are progoitrin, gluconapin, glucobrassicana-pin, napoleiferin, glucoraphanin, glucoalyssin, glu-cobrassicin and neoglucobrassicin20 and for doublelow rapeseed it is especially 4-hydroxyglucobrassicinwhich is quantitatively dominating.26,27 These glu-cosinolates are totally diþerent from those found inBarbarea and Lepidium. In a study of antinutritionaland toxic eþects caused by glucosinolates addedsingly to a standard rat diet, it has been shown thatdiþerent glucosinolates have diþerent eþects, includ-ing eþects on internal organs.28,29 For example, glu-cobarbarin reduced consumption and increased theweight of the liver, kidney and thyroid, while sinal-bin decreased the biological value and net proteinutilisation.

The relative composition of the aromatic cholineesters cis-coumaroyl choline, trans-coumaroylcholine, cis-isoferuloyl choline and trans-isoferuloylcholine was about the same in both B vulgaris and Bverna, and with a total content of about 15lmol g~1

J Sci Food Agric 79 :179–186 (1999) 183

AAM Andersson et al

Table 6. Content of glucos inolates and is oferuloylderivatives of glucos inolates (lmol gÉ1) in collected s eeds of Barbarea vulgaris ,

Barbarea verna andLepidium campes tre



Glucoiberin NDa ND traces

Glucoalys s in ND ND 24.4 22.0–26.6 7.8

Glucoraphanin ND ND 4.0 2.4–5.2 30.4

Gluconapin ND ND traces

Glucoibervirin ND ND traces

Glucotropaeolin ND ND ND

Gluconas turtiin 7.5 5.3–12.6 38.7 105.8 92.2–134.3 15.7 ND

Glucobarbarin 108.2 86.3–124.8 14.5 ND ND

Is oferuloyl at C6 1.7 1.5–1.8 8.0 ND ND

Is oferuloyl at C2 0.2 0.2–0.2 0.0 ND ND

Diis oferuloyl

at C2 and C6 0.05 0.05–0.05 0.0 ND ND

Glucos ibarin 4.3 1.3–12.4 108.0 ND ND

Sinalbin ND ND 109.9 93.2–116.3 8.6

Glucobras s icin 0.8 0.4–1.6 64.9 traces traces

4-Methoxy-

glucobras s icin traces traces ND

Neoglucobras s icin traces traces traces

a ND, not detected.

seed. In L campestre another choline ester domi-nated, namely 4-hydroxybenzoylcholine. Thecontent of aromatic choline esters has been investi-gated before in seeds of cruciferous species by Bou-chereau et al.30 They found for example4-hydroxybenzoylcholine in Matthiola sinuata,Sinapis alba and Sinapis arvenis, and isoferuloylcholine in M sinuata.

There were no cyanogens found at all in theungerminated seeds of either B vulgaris, B verna orL campestre, which is advantageous if the meal isgoing to be used as human food or animal feed, sincecertain central nervous system syndromes have beenshown to be cyanide dependent.31

CONCLUSIONS

The chemical composition of the potential newoilseed crops B vulgaris, B verna and L campestreshowed little variation between diþerent samples.The major constituents found were dietary übre,crude fat and crude protein. Ash was found insmaller amounts and starch only in trace amounts.The content of ash and dietary übre was high com-pared to rapeseed, while the content of fat andprotein was low. To make Barbarea and Lepidiumvaluable oil crops, the content of fat and protein hasto be increased.

The amino acid composition was good accordingto the reference pattern for amino acid compositionfor humans. The fatty acid composition was domi-nated by erucic acid in Barbarea and linolenic acid inLepidium. The major constituents of the dietaryübres were Klason lignin and uronic acid, glucose,

arabinose and galactose residues, which are the sameas have been found in rapeseed. The content of glu-cosinolates was about the same as in old rapeseedvarieties but the types found were totally diþerent.However, as glucosinolates and especially degrada-tion products thereof are antinutritional and toxic,they have to be removed from the seeds by plantbreeding or during processing, if the meal is going tobe used as human food or animal feed.

For the continuation of the breeding programme,individual plants from the accessions would have tobe analysed for variation of quality traits. Availablemutation populations might add even more variation.There is a great need of a new oilseed crop in thetemperate region, and by selection for advantageouscharacteristics and with help of gene technology,Barbarea and Lepidium have every chance of suc-ceeding.

ACKNOWLEDGEMENTS

Leon Brimer at The Royal Veterinary and Agricul-tural University is gratefully acknowledged for carry-ing out the analysis of cyanogens. The authors alsowish to thank Svenska Cereallaboratoriet AB,Svalo� v, Sweden for performing the fatty acidanalysis and AnalyCen AB, Lidko� ping, Sweden forperforming the amino acid analysis. Financialsupport for this work was partly provided bySwedish Farmers Foundation for AgriculturalResearch. Financial support from the Commission ofthe European Communities, Agriculture and Fish-eries (FAIR) speciüc RTD programme CT95-0260High Quality Oils, Proteins and Bioactive Products

184 J Sci Food Agric 79 :179–186 (1999)


Table 7. Structures and trivial names of the glucos inolates found inBarbarea vulgaris , Barbarea verna andLepidium campes tre .

Compare with Fig 1 for explanations of R, andR2

R6

Glucos inolate R R2

R6

Glucoiberin CH3SOCH

2CH

2CH

2É H H

Glucoalys s in CH3SOCH

2CH

2CH

2CH

2CH

2É H H

Glucoraphanin CH3SOCH

2CH

2CH

2CH

2É H H

Gluconapin CH2CHCH

2CH

2É H H

Glucoibervirin CH3SCH

2CH

2CH

2É H H

Glucotropaeolin H H

Gluconas turtiin H H

Glucobarbarina H H

Is oferuloyl at C6 H

Is oferuloyl at C2 H

Diis oferuloyl

at C2 and C6

Glucos ibarinb H H

Sinalbin H H

Glucobras s icin H H

Neoglucobras s icin H H

4-Methoxy- H H

glucobras s icin

a (2S)-configuration.

b (2R)-configuration.

J Sci Food Agric 79 :179–186 (1999) 185

AAM Andersson et al

for Food and Non-Food Purposes based on Bio-reüning of Cruciferous Oilseed Crops is gratefullyacknowledged.

REFERENCES1 Merker A and Nilsson P, Some oil crop properties in wild

Barbarea and Lepidium species. Swedish J Agric Res 25 :173–178 (1995).

2 Appelqvist L-A, Lipids in Cruciferae: VIII : The fatty acidcomposition of seeds of some wild or partially domesticatedspecies. J Am Oil Chem Soc 48 :740–744 (1971).

3 Princen LH, New oilseed crops on the horizon. Econ Bot

37 :478–492 (1983).4 Jensen ES, Nitrogen accumulation and residual eþects of

nitrogen catch crops. Acta Agric Scand 41 :333–344 (1991).H, Glucosinolates : structure–properties–function, in5 SÔrensen

Canola and Rapeseed. Production, Chemistry, Nutrition and

Processing Technology, Ed by Shahidi F. Van NostrandReinhold, New York, USA, pp 149–172 (1990).

P, Westerlund E and Theander O, Determination of6 A� manstarch using a thermostable alfa-amylase. Methods Carbohydr

Chem 10 :111–115 (1994).7 AOAC, Official Methods of Analysis (14th edn). Association of

Official Analytical Chemists, Washington, DC, USA (1984).8 Anon, Determination of crude oils and fats. Offic J Eur Comm

L15 :29–30 (1984).9 Theander O and Westerlund EA, Studies on dietary übre. 3.

Improved procedures for analysis of dietary übre. J Agric

Food Chem 34 :330–336 (1986).10 Theander O, P, Westerlund E, Andersson R and Pet-A� man

tersson D, Total dietary übre determined as neutral sugarresidues, uronic acid residues, and Klason lignin, gas-chromatographic-colorimetric-gravimetric method (UppsalaMethod), in AOAC Official Methods of Analysis (16th edn,Suppl 1), AOAC, Washington, DC, USA, method 994.13(1995).

11 Johansson and Uppstro� m B, Analys av oljeva� xtfro� :S-A�Besta� mning av fettsyrasammansa� ttning. Sveriges

Tidskrift 88 :35–44 (1978).Utsa� desfo� renings

12 Llames CR and Fontaine J, Determination of amino acids infeed: Colloborative study. J AOAC Int 77 :1362–1402(1994).

13 Brimer L, Quantitative solid-state detection of cyanogens :From üeld test kits to semi-automated laboratory systemsallowing kinetic measurements. Acta Hortic 375 :105–116(1994).

14 Michaelsen S, Mo� ller P and H, Factors inýuencingSÔrensenthe separation and quantitation of intact glucosinolates anddesulphoglucosinolates by micellar electrokinetic capillarychromatography. J Chromatogr 608 :363–374 (1992).

15 Bjergegaard C, Michaelsen S, Mo� ller P and H,SÔrensenSeparation of desulphoglucosinolates by micellar electro-kinetic capillary chromatography based on a bile salt. J

Chromatogr A 717 :325–333 (1995).16 Bjergegaard C, Ingvardsen L and H, DeterminationSÔrensen

of aromatic choline esters by micellar electrokinetic capillarychromatography. J Chromatogr 653 :99–108 (1993).

17 Eriksson I, Westerlund E and P, Chemical compositionA� manin varieties of rapeseed and turnip rapeseed, includingseveral samples of hull and dehulled seed. J Sci Food Agric

66 :233–240 (1994).18 Blair R and Reichert RD, Carbohydrate and phenolic constitu-

ents in a comprehensive range of rapeseed and canola frac-tions : Nutritional signiücance for animals. J Sci Food Agric

35 :29–35 (1984).19 Food and Nutrition Board, RDA (Recommended dietary

allowances) National Academy of Sciences, Washington DC,USA (1980).

20 Bell JM, Nutrients and toxicants in rapeseed meal : a review. J

Anim Sci 58 :996–1010 (1984).21 Anjou K, Lo� nnerdal B, Uppstro� m B and P, Composi-A� man

tion of seeds from Brassica cultivars. Swedish J Agric Res

7 :169–178 (1977).22 Jo� nsson R and Uppstro� m B, Quality breeding in rapeseed, in

1886–1986 Research and Results in Plant Breeding,SVALO� FEd by Olsson G. LT, Stockholm, Sweden, pp 173–184(1986).

23 Wannerberger K, Nylander T and Nyman M, Rheological andchemical properties of mucilage in diþerent varieties fromlinseed (Linum usitatissimum). Acta Agric Scand 41 :311–319(1991).

24 Bagger CL, H, JC, High quality oils, pro-SÔrensen SÔrensenteins and bioactive products for food and non-food purposesbased on bioreüning of cruciferous oilseed crops, in Pro-

ceedings of Conference on Plant Proteins from European Crops.Food and Non-Food Applications. p 71, Nantes, France,(1996).

25 Shahidi F, Rapeseed and canola: Global production and dis-tribution, in Canola and Rapeseed. Production, Chemistry,Nutrition and Processing Technology, Ed by Shahidi F. VanNostrand Reinhold, New York, USA, pp 3–13 (1990).

26 Bjerg B, Larsen LM and H, Reliability of analyticalSÔrensenmethods for quantitative determination of individual gluco-sinolates and total glucosinolate content in double lowoilseed rape, in 7th International Rapeseed Congress. pp1330–1341, Poznan, Poland, (1987).

27 Jensen SK, Michaelsen S, Kachlicki P and H, 4-SÔrensenHydroxyglucobrassicin and degradation products of gluco-sinolates in relation to unsolved problems with the quality ofdouble low oilseed rape, in GCIRC-Congress, 1359–1364Saskatoon, Canada, (1991).

28 Bille N, Eggum BO, Jacobsen I, Olsen O and H,SÔrensenAntinutritional and toxic eþects in rats of individual gluco-sinolates (] / [ myrosinases) added to a standard diet. 1.Eþects on protein utilization and organ weight. Z Tierphy-

siol, u Futtermittelkde 49 :195–210 (1983).Tiererna� hrg

29 Bjerg B, Eggum BO, Jacobsen I, Otte J and H, Anti-SÔrensennutritional and toxic eþects in rats of individual glucosinol-ates (] / [ myrosinases) added to a standard diet (2). Z

Tierphysiol Futtermittelkd 61 :227–244 (1989).Tiererna� hr

30 Bouchereau A, Hamelin J, Lamour I, Renard M and LarherF, Distribution of sinapine and related compounds in seedsof Brassica and allied genera. Phytochemistry 30 :1873–1881(1991).

31 Tylleska� r T, Banea M, Bikangi N, Cooke R, Poulter NH andRosling H, Cassava cyanogens and konzo, an upper moto-neuron disease found in Africa. Lancet 339 :208–211 (1992).

186 J Sci Food Agric 79 :179–186 (1999)

chemical composition of the potential new oilseed cropsbarbarea vulgaris,barbarea verna andlepidium...

Documents