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DEVELOPING DEVELOPING PURPLE WHEAT PURPLE WHEAT AS A SOURCE AS A SOURCE OFOF
ANTHOCYANIN PIGMENTS FOR FOOD ANDANTHOCYANIN PIGMENTS FOR FOOD ANDNON-FOOD APPLICATIONSNON-FOOD APPLICATIONS
El-Sayed M. Abdel-AalEl-Sayed M. Abdel-Aal11Guelph Food Research Centre, Guelph, Ontario, CanadaGuelph Food Research Centre, Guelph, Ontario, Canada
Euro Food June 2015Euro Food June 2015
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OUTLINEOUTLINE
• Development of colorful wheat and foodDevelopment of colorful wheat and food
• Anthocyanin in purple wheatAnthocyanin in purple wheat
• Role of anthocyanin in lifeRole of anthocyanin in life
• Purple wheat as a source of anthocyaninsPurple wheat as a source of anthocyanins
• Antioxidant properties of anthocyaninsAntioxidant properties of anthocyanins
• Preparation for human studiesPreparation for human studies
• ConclusionsConclusions
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DEVELOPMENT OF COLORFUL WHEATDEVELOPMENT OF COLORFUL WHEATAND PURPLE WHEAT FOODSAND PURPLE WHEAT FOODS
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Anthocyanin (mg/kg)
0 100 200 300 400 500 600
Dis
trib
uti
on
nu
mb
er
0
10
20
30
40
50
Range = 34.6-507.2Mean = 183.0SD = 95.7SE = 7.6n = 160
Abdel-Aal and Hucl, Cereal Chemistry, 1999, 76, 350
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Absorbance spectra of Cy-3-Glu and wheat extracts
Wavelength (nm)
440 480 520 560 600
Ab
so
rba
nc
e
0.0
0.2
0.4
0.6
0.8
Cy-3--Glu BW wholemeal BW bran PW wholemeal PW bran Blue barley
Abdel-Aal and Hucl, Cereal Chemistry, 1999, 76, 350
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Blue wheat Red wheat Purple wheat
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CDC Primepurple wheat2013
AnthoGrainTM
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Wheat Milling FractionsWheat Milling Fractions
Testa (3-4%)
Aleurone layer (7-8%)
Embryo (2-3%)
Pericarp (5-6%)
Endosperm (81-84%)
81849532212
ACNs, mg/kg
7.122.666.8100
Yield, %
Abdel-Aal et al., J. Agric. Food Chem., 2006, 54, 4696 Wheat kernelWheat kernel
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GlutenGlutenGliadinGliadin GluteninGlutenin
50 protein subunits50 protein subunits
Wheat Flour UniquenessWheat Flour Uniqueness
4-6 HMW & 15 LMW 4-6 HMW & 15 LMW >30 gliadins>30 gliadins
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Purple Wheat Food ApplicationsPurple Wheat Food Applications
• Breakfast CerealsBreakfast Cereals
• BreadsBreads
• SnacksSnacks
• CrackersCrackers
• NoodlesNoodles
• PancakesPancakes
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Purple Wheat FoodsPurple Wheat Foods
BreadBreadPancakePancake
NoodlesNoodlesFlakesFlakes MuffinMuffin
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ANTHOCYANINS IN PURPLE WHEATANTHOCYANINS IN PURPLE WHEAT
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OH
1
35
6
8
7
1'
2'
3'4'
6'
5'O
OH
HO
R1
R2
O glucose
2
4
Pelargonidin-3-glucoside: R1=H, R2=H
Cyanidin-3-glucoside: R1=OH, R2=H
Malvidin-3-glucoside: R1=OCH3, R2=OCH3
Peonidin-3-glucoside: R1=OCH3, R2=H
Petunidin-3-glucoside: R1=OCH3, R2=OH
Delphinidin-3-glucoside: R1=OH, R2=OH
Anthocyanin StructuresAnthocyanin Structures
Organic acid (aliphatic or phenolic)
A
B
C
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Compound Anthocyanin # of isomeric compounds
Major ion pair Concentration of anthocyanin
(µg/g) 1 Cy-diGlu 9 611/287 1.67 2 Dp-3-Glu 1 465/303 0.09 3 Dp-3-Rut 4 611/303 3.67 4 Dp-MalGlu 5 551/303 3.54 5 Dp-SucGlu 3 565/303 tr 6 Cy-3-Glu 1 449/287 116.66 7 Cy-3-Rut 1 595/287 85.06 8 Cy-MalGlu 4 535/287 150.28 9 Cy-SucGlu 3 549/287 1.00 10 Cy-MalSucGlu 1 635/287 tr 11 Pt-3-Glu 2 479/317 0.19 12 Pt-3-Rut 1 625/317 0.05 13 Pt-MalGlu 1 565/317 3.23 14 Pg-3-Glu 1 433/271 0.91 15 Pg-Rut 3 579/271 0.35 16 Pg- MalGlu 3 519/271 1.17 17 Pg-SucGlu 3 533/271 0.19 18 Pn-3-Glu 4 463/301 27.37 19 Pn-Rut 3 609/301 7.38 20 Pn-MalGlu 6 549/301 18.38 21 Pn-Glu Succ 3 563/301 0.03 22 Mv 3 Glu 3 493/331 0.28 23 Mv Rut 2 639/331 2.55 24 Mv Glu Mal 4 579/331 0.53 25 Mv Glu Succ 3 593/331 1.28 26 Mv Glu Mal Succ 1 679/331 0.16 Total 75 - 426.02
Characterization of anthocyanin compounds in purple wheat branCharacterization of anthocyanin compounds in purple wheat bran
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0100
Cy-3-Gl(+ ve)
449
287
465
303Dp-3-Gl
(+ ve)
0
100
100 1000
Pn-3-Gl(+ ve)
463
301
100 1000
Pt-3-Gl(+ ve)
479
317
100 1000100 1000
100
1000
Cy-dGl(+ ve)
611
287
100 1000
Cy-SGl(+ ve)287
549
100 1000
100
1400
Cy-3-Gl(- ve)
0
284
447
493 659
1343
895
M/Z
Ab
und
ance
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ROLE OF ANTHOCYANINS IN LIFEROLE OF ANTHOCYANINS IN LIFE
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Protection against UVProtection against UV
Pollination and seed dispersalPollination and seed dispersal
Reduction of oxidative stressReduction of oxidative stress
PlantsPlants
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Human HealthHuman Health
Biological antioxidantBiological antioxidant
Anti-inflammatory effectAnti-inflammatory effect
Anti-cancerAnti-cancer
Anti-diabetic effectAnti-diabetic effect
Ocular effectOcular effect
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Natural colorantNatural colorant
Dietary antioxidantDietary antioxidant
Food IndustryFood Industry
Functional ingredient Functional ingredient
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Cosmetic and healthcare IndustryCosmetic and healthcare Industry
Natural colorantsNatural colorants
Natural antioxidantsNatural antioxidants
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Daily intake: 12.5 mgDaily intake: 12.5 mg
of the total intake:of the total intake:45% cyanidin45% cyanidin
21% delphinidin21% delphinidin77% nonacylated77% nonacylated
73% monoglucoside73% monoglucoside
Wu et al., J. Agric. Food Chem., 2006, 54, 4069.
Anthocyanin ConsumptionAnthocyanin Consumption
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PURPLE WHEAT AS A SOURCE OFPURPLE WHEAT AS A SOURCE OFANTHOCYANINSANTHOCYANINS
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PPurple urple WWheat heat KKernelsernels
Abrasive or Roller MillingAbrasive or Roller Milling
White endospermWhite endosperm
Aqueous ethanol extractionAqueous ethanol extraction
PurificationPurification
DryingDrying
Column chromatographyColumn chromatography(amberlite XAD-7)(amberlite XAD-7)
BranBran
Anthocyanin powderAnthocyanin powder
CharacterizationCharacterization
Solvent proof ovenSolvent proof oven
Composition, color, stabilityComposition, color, stabilityantioxidant and biologicalantioxidant and biological
propertiesproperties
Bakery productsBakery products
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Purification by column chromatographyPurification by column chromatography
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Batch size Yield(g/batch)
Yield(mg/g)
Concentration of anthocyanin (mg/g)
Concentration factora
Purified-Amberlite10g 0.21 21.0 57.4 13550g 0.79 15.8 38.9 91100g 2.05 20.5 34.7 81Purified-C1850g 0.75 15.0 33.9 80Non-purified50g 1.17 23.4 13.7 32
Average yield and anthocyanin concentration in isolates
aRatio of anthocyanin concentration in powder to that in purple wheat bran.
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ANTIOXIDANT PROPERTIESANTIOXIDANT PROPERTIESOF ANTHOCYANINSOF ANTHOCYANINS
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DPPH scavenging capacity of blue wheatDPPH scavenging capacity of blue wheatbran and powderbran and powder
BranAnthocyanin powder
Product
401686
μmole/g10 min
462526
μmole/g30 min
Abdel-Aal et al., J Agric. Food Chem., 2008, 56, 11171
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ABTS scavenging capacity of blue ABTS scavenging capacity of blue wheatwheat
bran and powderbran and powder
BranAnthocyanin powder
Product
231610
μmole/g3 min
572925
μmole/g10 min
Abdel-Aal et al., J Agric. Food Chem., 2008, 56, 11171
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Inhibition of human LDL cholesterol oxidationInhibition of human LDL cholesterol oxidation((μμmole diene/g LDL/mg sample)mole diene/g LDL/mg sample)
Control (no antioxidant)BranAnthocyanin powder
Product
52817
0.062
8 hrs
53032
0.29
12 hrs
3811
0.055
2 hrs
58433
1.44
24 hrs
Abdel-Aal et al., J Agric. Food Chem., 2008, 56, 11171
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DPPH scavenging capacity of anthocyaninsDPPH scavenging capacity of anthocyanins
Dp-3-GluCy-3-GluDp-3-RutCy-3-Rut
Anthocyanin
7921113567
3967
μmole/g10 min
8311232613
4346
μmole/g30 min
Abdel-Aal et al., J Agric. Food Chem., 2008, 56, 11171
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ABTS scavenging capacity of anthocyaninsABTS scavenging capacity of anthocyanins
Dp-3-GluCy-3-GluDp-3-RutCy-3-Rut
Anthocyanin
1925332321673
μmole/g3 min
38210154303261
μmole/g10 min
Abdel-Aal et al., J Agric. Food Chem., 2008, 56, 11171
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Inhibition of human LDL cholesterol oxidationInhibition of human LDL cholesterol oxidation((μμmole diene/g LDL/mg sample)mole diene/g LDL/mg sample)
ControlDp-3-GluCy-3-GluDp-3-RutCy-3-RutBHT
Compound
5280.1190.6950.0923.13023.0
8 hrs
5300.2630.7200.2723.19630.5
12 hrs
3810.0420.3080.0471.25119.4
2 hrs
5840.2440.9280.2674.01836.6
24 hrs
Abdel-Aal et al., J Agric. Food Chem., 2008, 56, 11171
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HUMAN STUDIESHUMAN STUDIES
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Products Anthocyanin (µg/g)
Fresh weight basis
Dry matterbasis
Wholegrain bread 65 101
Wholegrain muffin 49 78
Wholegrain pancake 96 167
Wholegrain flakes (uncooked) 120 135
Wholegrain flakes (cooked) 48 116
Wholegrain instant flakes (uncooked) 129 146
Wholegrain instant flakes (cooked) 30 116
Anthocyanin content of Purple Wheat anthocyanin-enrichedproducts measured by spectrophotometric method
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Nutrient content of Purple Wheat anthocyanin-enrichedProducts (dry basis)
18.016.59.216.217.017.518.816.811.5
Wholegrain breadWholegrain bread + branWholegrain muffinWholegrain flakes (uncooked)Wholegrain flakes (cooked)Wholegrain instant flakes (uncooked)Wholegrain instant flakes (cooked)Wholegrain pancakeWholegrain flour
Products Protein
56.855.419.660.657.655.461.236.056.4
Starch
11.916.418.112.614.012.713.620.71.8
Fiber
6.45.114.52.11.51.71.37.912.6
Fat
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11stst study: bioavailability of anthocyanins and phenolic acids study: bioavailability of anthocyanins and phenolic acids & plasma antioxidant capacity& plasma antioxidant capacity
Foods:Foods:Purple wheat wholegrain breadPurple wheat wholegrain breadPurple wheat flakesPurple wheat flakes
Study participants:Study participants:Healthy individuals (18-55 Yrs, BMI 18-25)Healthy individuals (18-55 Yrs, BMI 18-25)
Study design:Study design:Randomized crossover acute meal study Randomized crossover acute meal study
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22ndnd study: intervention study, oxidative stress study: intervention study, oxidative stress and inflammation responsesand inflammation responses
Foods:Foods:Purple wheat wholegrain breadPurple wheat wholegrain breadPurple wheat flakesPurple wheat flakes
Study participants:Study participants:Individuals at riskIndividuals at risk
Study design:Study design:Randomized placebo crossover acute meal study Randomized placebo crossover acute meal study
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Dry and wet separation technologies can be used to isolateDry and wet separation technologies can be used to isolate anthocyanins from purple wheatanthocyanins from purple wheat
Take Home MessagesTake Home Messages
Purple wheat holds a promise for the development of natural Purple wheat holds a promise for the development of natural colorants and/or natural antioxidantscolorants and/or natural antioxidants
Purple wheat can be processed into a variety of staple foodsPurple wheat can be processed into a variety of staple foods for healthy dietsfor healthy diets
More research is underway to evaluate bioavailability and healthMore research is underway to evaluate bioavailability and health benefits of purple wheat productsbenefits of purple wheat products
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AcknowledgmentsAcknowledgments
CollaboratorsCollaborators• Dr. Pierre Hucl, U of SDr. Pierre Hucl, U of S• Dr. Amanda Wright, U of GDr. Amanda Wright, U of G• Mr. Mark Pickard, SaskatoonMr. Mark Pickard, Saskatoon
StudentsStudents• Tamer Gamel, U of GTamer Gamel, U of G• Tyler O’Leary, U of GTyler O’Leary, U of G• Riley DeForest, U of GRiley DeForest, U of G• Jacklyn Shipp, U of GJacklyn Shipp, U of G• Jessica SimonsJessica Simons
Research techniciansResearch technicians• Iwona RabalskiIwona Rabalski• Marta HernandezMarta Hernandez
Partners & GrantsPartners & Grants• InfraReady Inc, SaskatoonInfraReady Inc, Saskatoon• Canadian Food Innovation ClusterCanadian Food Innovation Cluster• Agriculture Development Fund of SaskatchewanAgriculture Development Fund of Saskatchewan• Agriculture and Agri-Food CanadaAgriculture and Agri-Food Canada
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THANK YOUTHANK YOUQuestions
AAFC Vision: Driving innovation and ingenuity to build a world leading agricultural and food economy for the benefit of all Canadians
AAFC Mission: to provide leadership in the growth and development of a competitive,innovative and sustainable Canadian agriculture and agri-food sector