Distribution number. Anthocyanin (mg/kg) Range = Mean = SD = 95.7 SE = 7.6 n = 160

Full text

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DEVELOPING

DEVELOPING PURPLE WHEAT PURPLE WHEAT AS A SOURCE OF AS A SOURCE OF ANTHOCYANIN PIGMENTS FOR FOOD AND ANTHOCYANIN PIGMENTS FOR FOOD AND ANTHOCYANIN PIGMENTS FOR FOOD AND ANTHOCYANIN PIGMENTS FOR FOOD AND

NON

NON--FOOD APPLICATIONS FOOD APPLICATIONS

El

El--Sayed M. Abdel Sayed M. Abdel--Aal Aal

11Guelph Food Research Centre, Guelph, Ontario, CanadaGuelph Food Research Centre, Guelph, Ontario, Canada Euro Food June 2015

Euro Food June 2015

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OUTLINE OUTLINE

•• Development of colorful wheat and food Development of colorful wheat and food

•• Anthocyanin in purple wheat Anthocyanin in purple wheat

•• Role of anthocyanin in life Role of anthocyanin in life

•• Purple wheat as a source of Purple wheat as a source of anthocyanins anthocyanins

2

•• Purple wheat as a source of Purple wheat as a source of anthocyanins anthocyanins

•• Antioxidant properties of Antioxidant properties of anthocyanins anthocyanins

•• Preparation for human studies Preparation for human studies

•• Conclusions Conclusions

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DEVELOPMENT OF COLORFUL WHEAT DEVELOPMENT OF COLORFUL WHEAT

AND PURPLE WHEAT FOODS

AND PURPLE WHEAT FOODS

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Distribution number

20 30 40 50

Range = 34.6-507.2 Mean = 183.0 SD = 95.7 SE = 7.6 n = 160

4

Anthocyanin (mg/kg)

0 100 200 300 400 500 600

Distribution number

0 10

Abdel-Aal and Hucl, Cereal Chemistry, 1999, 76, 350

(5)

Absorbance

0.4 0.6 0.8

Cy-3--Glu BW wholemeal BW bran PW wholemeal PW bran Blue barley

Absorbance spectra of Cy-3-Glu and wheat extracts

Wavelength (nm)

440 480 520 560 600

0.0 0.2

(6)

Blue wheat Red wheat

Purple wheat

6

(7)

CDC Primepurple wheat 2013

AnthoGrainTM

(8)

Wheat Milling Fractions Wheat Milling Fractions

Testa (3-4%)

Aleurone layer (7-8%) Pericarp (5-6%)

Endosperm (81-84%)

818 ACNs, mg/kg 7.1

Yield, %

8 Embryo (2-3%)

818 495 32 212 7.1

22.6 66.8 100

Abdel-Aal et al., J. Agric. Food Chem., 2006, 54, 4696 Wheat kernel

Wheat kernel

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Wheat Flour Uniqueness Wheat Flour Uniqueness

Gluten Gluten Gliadin

Gliadin GluteninGlutenin

50 protein subunits 50 protein subunits

44--6 HMW & 15 LMW 6 HMW & 15 LMW

>30 gliadins

>30 gliadins

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Purple Wheat Food Applications Purple Wheat Food Applications

•• Breakfast CerealsBreakfast Cereals

•• BreadsBreads

•• SnacksSnacks

•• NoodlesNoodles

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•• CrackersCrackers

•• PancakesPancakes

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Purple Wheat Foods Purple Wheat Foods

Bread Bread Pancake

Pancake

Noodles Noodles Flakes

Flakes MuffinMuffin

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ANTHOCYANINS IN PURPLE WHEAT ANTHOCYANINS IN PURPLE WHEAT

12

(13)

OH

1

6 3 8 7

1' 2'

3' 4'

6'

O 5'

HO

R1

R2

O glucose

2

Pelargonidin-3-glucoside: R1=H, R2=H Cyanidin-3-glucoside: R1=OH, R2=H Petunidin-3-glucoside: R1=OCH3, R2=OH Delphinidin-3-glucoside: R1=OH, R2=OH

Anthocyanin Structures Anthocyanin Structures

A

B

C

5 3

OH

O glucose

4

Malvidin-3-glucoside: R1=OCH3, R2=OCH3 Peonidin-3-glucoside: R1=OCH3, R2=H

Organic acid (aliphatic or phenolic)

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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

Characterization of anthocyanin compounds in purple wheat bran Characterization of anthocyanin compounds in purple wheat bran

14

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

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Cy-3-Gl (+ ve) 449

287 465

303

Dp-3-Gl (+ ve)

0 100

100 1000

Pn-3-Gl (+ ve) 463

301

Pt-3-Gl (+ ve) 479

317

100 1000

100 1000

100

Cy-dGl (+ ve) 611

287

Cy-SGl (+ ve) 287

549

Abundance

16

0100 1000100 1000 100 1000

100 1000

100

1400 Cy-3-Gl

(- ve)

0

284 447

493 659

1343 895

M/Z

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ROLE OF ANTHOCYANINS IN LIFE

ROLE OF ANTHOCYANINS IN LIFE

(18)



 Protection against UVProtection against UV



 Pollination and seed dispersalPollination and seed dispersal



 Reduction of oxidative stressReduction of oxidative stress Plants

Plants

18



 Reduction of oxidative stressReduction of oxidative stress

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Human Health Human Health



 Biological antioxidantBiological antioxidant



 AntiAnti--inflammatory effectinflammatory effect



 AntiAnti--cancercancer



 AntiAnti--diabetic effectdiabetic effect



 Ocular effectOcular effect

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 Natural colorantNatural colorant



 Dietary antioxidantDietary antioxidant Food Industry

Food Industry



 Functional ingredient Functional ingredient

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 Functional ingredient Functional ingredient

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Cosmetic and healthcare Industry Cosmetic and healthcare Industry



 Natural colorantsNatural colorants



 Natural antioxidantsNatural antioxidants

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Daily intake: 12.5 mg Daily intake: 12.5 mg

of the total intake:

of the total intake:

45%

45% cyanidincyanidin 21%

21% delphinidindelphinidin 77%

77% nonacylatednonacylated

Anthocyanin Consumption Anthocyanin Consumption

22

77%

77% nonacylatednonacylated 73%

73% monoglucosidemonoglucoside

Wu et al., J. Agric. Food Chem., 2006, 54, 4069.

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PURPLE WHEAT AS A SOURCE OF PURPLE WHEAT AS A SOURCE OF

ANTHOCYANINS

ANTHOCYANINS

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P

P

urple urple

W W

heat heat

K K

ernelsernels

Abrasive or Roller Milling Abrasive or Roller Milling White endosperm

White endosperm

Aqueous ethanol extraction Aqueous ethanol extraction

Purification

Purification Column chromatographyColumn chromatography ((amberliteamberlite XADXAD--7)7)

Bran Bran

Bakery products Bakery products

24

Drying Drying

((amberliteamberlite XADXAD--7)7)

Anthocyanin powder Anthocyanin powder

Characterization Characterization

Solvent proof oven Solvent proof oven

Composition, color, stability Composition, color, stability antioxidant and biological antioxidant and biological

properties properties

(25)

Purification by column chromatography Purification by column chromatography

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Batch size Yield (g/batch)

Yield (mg/g)

Concentration of anthocyanin (mg/g)

Concentration factora Purified-Amberlite

10g 0.21 21.0 57.4 135

50g 0.79 15.8 38.9 91

Average yield and anthocyanin concentration in isolates

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100g 2.05 20.5 34.7 81

Purified-C18

50g 0.75 15.0 33.9 80

Non-purified

50g 1.17 23.4 13.7 32

aRatio of anthocyanin concentration in powder to that in purple wheat bran.

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ANTIOXIDANT PROPERTIES ANTIOXIDANT PROPERTIES

OF ANTHOCYANINS

OF ANTHOCYANINS

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DPPH scavenging capacity of blue wheat DPPH scavenging capacity of blue wheat

bran and powder bran and powder

Bran Product

40 µmole/g

10 min

46 µmole/g

30 min

28

Bran

Anthocyanin powder

40 1686

46 2526

Abdel-Aal et al., J Agric. Food Chem., 2008, 56, 11171

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ABTS scavenging capacity of blue wheat ABTS scavenging capacity of blue wheat

bran and powder bran and powder

Bran Product

23 µmole/g

3 min

57 µmole/g

10 min Bran

Anthocyanin powder

23 1610

57 2925

Abdel-Aal et al., J Agric. Food Chem., 2008, 56, 11171

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Inhibition of human LDL cholesterol oxidation Inhibition of human LDL cholesterol oxidation

((µµmole mole dienediene/g LDL/mg sample)/g LDL/mg sample)

Control (no antioxidant) Bran

Product

528 17 8 hrs

530 32 12 hrs 381

1 2 hrs

584 33 24 hrs

30

Bran

Anthocyanin powder

17 0.062

32 0.29 1

0.055

33 1.44

Abdel-Aal et al., J Agric. Food Chem., 2008, 56, 11171

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DPPH scavenging capacity of

DPPH scavenging capacity of anthocyaninsanthocyanins

Dp-3-Glu Anthocyanin

792 µmole/g

10 min

831 µmole/g

30 min Dp-3-Glu

Cy-3-Glu Dp-3-Rut Cy-3-Rut

792 1113

567 3967

831 1232

613 4346

Abdel-Aal et al., J Agric. Food Chem., 2008, 56, 11171

(32)

ABTS scavenging capacity of

ABTS scavenging capacity of anthocyaninsanthocyanins

Dp-3-Glu Anthocyanin

192 µmole/g

3 min

382 µmole/g

10 min

32

Dp-3-Glu Cy-3-Glu Dp-3-Rut Cy-3-Rut

192 533 232 1673

382 1015

430 3261

Abdel-Aal et al., J Agric. Food Chem., 2008, 56, 11171

(33)

Inhibition of human LDL cholesterol oxidation Inhibition of human LDL cholesterol oxidation

((µµmole mole dienediene/g LDL/mg sample)/g LDL/mg sample)

Control Dp-3-Glu Compound

528 0.119 8 hrs

530 0.263 12 hrs 381

0.042 2 hrs

584 0.244 24 hrs

Dp-3-Glu Cy-3-Glu Dp-3-Rut Cy-3-Rut BHT

0.119 0.695 0.092 3.130 23.0

0.263 0.720 0.272 3.196 30.5 0.042

0.308 0.047 1.251 19.4

0.244 0.928 0.267 4.018 36.6

Abdel-Aal et al., J Agric. Food Chem., 2008, 56, 11171

(34)

HUMAN STUDIES HUMAN STUDIES

34

(35)

Products Anthocyanin (µg/g) Fresh weight

basis

Dry matter basis

Wholegrain bread 65 101

Wholegrain muffin 49 78

Anthocyanin content of Purple Wheat anthocyanin-enriched products measured by spectrophotometric method

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

(36)

Nutrient content of Purple Wheat anthocyanin-enriched Products (dry basis)

18.0 16.5 9.2 16.2 Wholegrain bread

Wholegrain bread + bran Wholegrain muffin

Wholegrain flakes (uncooked)

Products Protein

56.8 55.4 19.6 60.6 Starch

11.9 16.4 18.1 12.6 Fiber

6.4 5.1 14.5

2.1 Fat

36

16.2 17.0 17.5 18.8 16.8 11.5 Wholegrain flakes (uncooked)

Wholegrain flakes (cooked)

Wholegrain instant flakes (uncooked) Wholegrain instant flakes (cooked) Wholegrain pancake

Wholegrain flour

60.6 57.6 55.4 61.2 36.0 56.4

12.6 14.0 12.7 13.6 20.7 1.8

2.1 1.5 1.7 1.3 7.9 12.6

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11

stst

study: bioavailability of study: bioavailability of anthocyanins anthocyanins and phenolic acids and phenolic acids

& plasma antioxidant capacity

& plasma antioxidant capacity Foods:

Foods:

Purple wheat wholegrain bread Purple wheat wholegrain bread Purple wheat flakes

Purple wheat flakes Study participants:

Study participants:

Study participants:

Study participants:

Healthy individuals (18

Healthy individuals (18--55 55 Yrs Yrs, BMI 18 , BMI 18--25) 25) Study design:

Study design:

Randomized crossover acute meal study

Randomized crossover acute meal study

(38)

22

ndnd

study: intervention study, oxidative stress study: intervention study, oxidative stress and inflammation responses

and inflammation responses Foods:

Foods:

Purple wheat wholegrain bread Purple wheat wholegrain bread Purple wheat flakes

Purple wheat flakes Study participants:

Study participants:

38

Study participants:

Study participants:

Individuals at risk Individuals at risk Study design:

Study design:

Randomized placebo crossover acute meal study

Randomized placebo crossover acute meal study

(39)



 Dry and wet separation technologies can be used to isolateDry and wet separation technologies can be used to isolate

Take Home Messages Take 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 antioxidants

colorants 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 diets

for healthy diets



 Dry and wet separation technologies can be used to isolateDry and wet separation technologies can be used to isolate anthocyanins

anthocyanins from purple wheatfrom purple wheat



 More research is underway to evaluate bioavailability and healthMore research is underway to evaluate bioavailability and health benefits of purple wheat products

benefits of purple wheat products

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Acknowledgments Acknowledgments

Collaborators Collaborators

•• Dr. Pierre Dr. Pierre HuclHucl, U of S, U of S

•• Dr. Amanda Wright, U of GDr. Amanda Wright, U of G

•• Mr. Mark Pickard, SaskatoonMr. Mark Pickard, Saskatoon

Students Students

•• Tamer Gamel, U of GTamer Gamel, U of G Research technicians Research technicians

•• Iwona RabalskiIwona Rabalski

•• Marta HernandezMarta Hernandez

Partners & Grants Partners & Grants

40

•• Tamer Gamel, U of GTamer Gamel, U of G

•• Tyler O’Leary, U of GTyler O’Leary, U of G

•• Riley Riley DeForestDeForest, U of G, U of G

•• Jacklyn Shipp, U of GJacklyn Shipp, U of G

•• Jessica SimonsJessica Simons Partners & Grants

Partners & Grants

•• InfraReadyInfraReady Inc, SaskatoonInc, Saskatoon

•• Canadian Food Innovation ClusterCanadian Food Innovation Cluster

•• Agriculture Development Fund of SaskatchewanAgriculture Development Fund of Saskatchewan

•• Agriculture and Agriculture and AgriAgri--Food CanadaFood Canada

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THANK YOU THANK YOU THANK YOU THANK YOU

Questions

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AAFC Mission:to provide leadership in the growth and development of a competitive, innovative and sustainable Canadian agriculture and agri-food sector

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References

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Related subjects : RANGE AND MEAN