Transcript Buckwheat enhanced wheat breads

4th International Conference and Exhibition on Food Processing & Technology
August 10-12, 2015 London, UK
Inhibitory Effect of Buckwheat Derived Bakery
Products on the Formation of Advanced
Glycation End Products – a Comparison Study
Henryk Zieliński
Institute of Animal Reproduction and Food
Research of the Polish Academy of Sciences in Olsztyn, Poland
4th International Conference and Exhibition on Food Processing & Technology
August 10-12, 2015 London, UK
INTRODUCTION
4th International Conference and Exhibition on Food Processing & Technology
August 10-12, 2015 London, UK
French chemist Louis-Camille Maillard
described the reaction between amino
acids and sugars in 1912.
His study did not offer much in the way of
analysis on the reaction’s impact on flavour
and aroma in food.
PROTEIN GLICATION
O
R - NH2
+
H
HO
H
H
OH
H
OH
OH
OH
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In 1973, American chemist John E Hodge
published a mechanism for the different steps of
the reaction.
He identified the first stage as being the reaction
between the sugar and the amino acid; this
produced a glycosylamine compound, which in the
second step rearranged to produce a ketosamine.
The final stage consists of this compound reacting
in a number of ways to produce several different
compounds, which can themselves react to
produce further products.
4th International Conference and Exhibition on Food Processing & Technology
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Scheme of Maillard reaction
Initial stage
Advanced stage
Amadori compounds
Fluorescence compounds
Carboxymethyllysine CML
Pyralline
Pentosidine
Final stage
Melanoidins
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Hodge Diagram Summarising the MR
+ amino compound
A
- H2O
Aldose
N-substituted glycosylamine
B
Amadori
rearrangement
Amadori product (1-amino-1-deoxy-2-ketose)
C - 3H2O
C
Schiff’s base of
hydroxymethylfurfural
or 2-furaldehyde
- 2H2O
Sugars
D
H
Fission products (acetol, diacetyl, pyruvaldehyde, etc.)
+ α-amino acid
E - CO2
(Strecker
degradation)
- amino compound
- 2H
Reductones
+ H2O
+ 2H
F
Hydroxymethylfurfural or 2-furaldehyde
G + amino
compound
F
E
Dehydroreductones
F
Aldehydes
F
Aldols and nitrogenfree polymers
G + amino
G + amino
compound
compound
Melanoidins (brown nitrogenous polymers and copolymers)
G + amino G + amino
compound compound
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FOOD
Advanced glycation endproducts (AGEs) are produced in the advanced stage of
nonenzymatic reaction between reducing sugars and amino groups, when the
group of intermediate compounds produced during Amadori rearrangements
react with amino groups either oxidatively or non-oxidatevely. AGEs formation is
a comprehensive result of amine blockage by the oxidative degradation
products of sugar or lipid.
HUMAN ORGANISM
In addition to dietary sources where they are generated during food processing and
storage, AGEs would also form and accumulate in vivo via sugar-protein
interactions and cause pathogenic concequences such as diabetic complications.
4th International Conference and Exhibition on Food Processing & Technology
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The initial reaction between glucose and protein amino groups forms a reversible
Schiff base that rearranges to a ketoamine or Amadori product. With time, these
Amadori products form AGEs via dicarbonyl intermediates such as 3-DG.
N. Ahmed /Diabetes Research and Clinical Practice 67 (2005) 3–21
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Autoxidative glycation where glucose is converted to a dicarbonyl ketoaldehye via
its enediol radical. This ketoaldehyde can react with a protein amino group to form
a ketoimine capable of forming AGEs. These steps are catalysed by transition metals
(M) and the superoxide radical generated can be converted to the hydroxyl radical
via the Fenton reaction.
N. Ahmed /Diabetes Research and Clinical Practice 67 (2005) 3–21
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August 10-12, 2015 London, UK
Chemical structure of (a) fluorescent cross-linking AGEs such as pentosidine and crossline, (b) nonfluorescent cross-linking AGEs such as imadazolium dilysine cross-links, alkyl formyl glycosyl pyrroles
and arginine–lysine imidazole cross-links, (c) non-cross-linking AGEs such as pyrraline and Ncarboxymethyllysine.
N. Ahmed /Diabetes Research and Clinical Practice 67 (2005) 3–21
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Medical consequences of protein glycation
Aging due to the colagen glycation
Diabetic complications
Skin aging
Cataract
Glycated hemoglobin
Enhanced formation and accumulation of AGEs have been implicated as a major pathogenesis
process leading to diabetic complications, normal aging, atherosclerosis, and Alzheimer’s
Disease.
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Studies for discovering and characteriying effective AGEs-inhibitors are
valuable in exploring therapeutic approaches for treating AGEs associated
diseases.
AGEs inhibitory mechanisms
Blocking sugar
attachment
Scavenging reactive radicals
and carbonyls from lipid or
sugar oxidation
Breaking sugar-protein
cross-links
4th International Conference and Exhibition on Food Processing & Technology
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AGEs-inhibitors
Synthetic
Aminoguanidine
Metformin
Carnosine
Tenilsetam
Aspirin
Vitamin B1 and B6 derivatives
Natural
Phenolic acid and flavonoids:
Caffeic acid
Chlorogenic acid
Epigallocatechin
Flavone C-glucosides
Quercitin
Rutin
Food rich in polyphenols:
Green tea
Tea infused with selected herbs
Tomato paste
Spices
4th International Conference and Exhibition on Food Processing & Technology
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Immunosupressive
Anti-inflammatory
POLYPHENOLS
FROM FOOD
Apoptosis Inducer
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Biologically active compounds of buckwheat with
beneficial action on consumer’s organism
Proteins
extract
Proteins
Phytosterols
Phytosterols
Cholesterollowering effect
Thiamin-binding
proteins
Fagopirins
D-chiro-inositol
Improving the
immunological status
Utilized in the
treatment of type II
diabetes
Flavonoids
Beneficial in treatment of
the hypertension, obesity,
alcoholism, constipation
Utilized for people
who suffer from the
lack of thiamin and can
not store thiamin
4th International Conference and Exhibition on Food Processing & Technology
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Buckwheat phytochemicals attracting attention due to
their potential health beneficial action
R1
3'
8
HO
4'
2'
R4
B
1
9
O
2
5'
1'
7
R3
6
5
OH
6'
C
A
10
OH
3
4
R2
O
Buckwheat
flavonoids
R1
R2
R3
R4
rutin
OH
rutinose
H
H
quercetin
OH
OH
H
H
quercitrin
OH
ramnose
H
H
orientin
OH
H
H
glucose
homoorientin
OH
H
glucose
H
vitexin
H
H
H
glucose
isovitexin
H
H
glucose
H
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BUCKWHEAT INDUSTRY IN POLAND
Raw buckwheat
Steaming
Roasting
Dehulling
Typical milling products from
unhusked and husked
buckwheat
Hulls – waste
byproduct
Roasted groat
Milling
Novel buckwheat
flour from roasted
groats
Flour from
husked
buckwheat
Wholegrain
buckwheat
flour
4th International Conference and Exhibition on Food Processing & Technology
August 10-12, 2015 London, UK
Potential health beneficial action of buckwheat flavonoids
Rutin (quercetin-3-rutinoside)
•
•
•
•
•
•
•
•
•
•
•
anti-inflammatory and vasoactive properties
capability to diminish capillary permeability
reduce the risk of arteriosclerosis
reducing coronary heart disease,
diminishing of platelet aggregation
inhibiting low-density lipoprotein (LDL) peroxidation
protective effects against ethanol-induced gastric lesions
against DNA damage
protective agent against carcinogenesis
the most potent natural inhibitors of AGEs formation
hypocholesterolemic effect in humans after the intake of buckwheat products.
Orientin
Homoorientin
Isovitexin
Vitexin
•
•
•
•
•
•
hypotensive properties
anti-inflammatory
antispasmodic
antimicrobial
radioprotective effects
anti-glycation activity
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Degradation of rutin in the colon
Pashikanti S., de Alba D.R., Boissonneault G.A., Cervanted-Laurean. Rutin metabolites: Novel inhibitors of
nonoxidative advanced glycation end products. Free Radical Biology & Medicine 48 (2010) 656-663
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THE AIM OF THE STUDY
To find out the potential non-pharmacologic
prevention of buckwheat enhanced bakery products
against formation of advanced glycation end
products (AGEs) due to the presence of quercetin-3O-rutinoside (rutin) – the main buckwheat flavonoid
and other polyphenol sources.
4th International Conference and Exhibition on Food Processing & Technology
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MATERIAL
PART I. BUCKWHEAT ENHANCED WHEAT BREADS
PART II. RYE-BUCKWHEAT GINGER CAKES ENRICHED WITH RUTIN
PART III. INNOVATIVE BREADS ENHANCED WITH NATURAL
INGREDIENTS CONTAINING POLYPHENOLS
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PART I. BUCKWHEAT ENHANCED WHEAT BREADS
• White wheat flour type 500,
• buckwheat flour “BIO” from whole grain of common
buckwheat (variety Kora),
• novel flour from roasted buckwheat groats
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August 10-12, 2015 London, UK
Buckwheat enhanced wheat breads
Reference white wheat bread
100%
buckwheat flour
“BIO”
10%
90%
Buckwheat enriched wheat bread (10/90)
20%
80%
Buckwheat enriched wheat bread (20/80)
30%
70%
40%
60%
50%
50%
white wheat
flour
Buckwheat enriched wheat bread (40/60)
Buckwheat enriched wheat bread (50/50)
Reference white wheat bread
100%
buckwheat
flour from
roasted groat
Buckwheat enriched wheat bread (30/70)
10%
90%
20%
80%
30%
70%
40%
60%
50%
50%
Buckwheat enriched wheat bread (10/90)
white wheat
flour
Buckwheat enriched wheat bread (20/80)
Buckwheat enriched wheat bread (30/70)
Buckwheat enriched wheat bread (40/60)
Buckwheat enriched wheat bread (50/50)
4th International Conference and Exhibition on Food Processing & Technology
August 10-12, 2015 London, UK
Buckwheat enhanced white wheat breads formulation and baking conditions
White wheat flour type 500
Buckwheat flour „BIO”
Dough making
Flour mixing
Substitution 10%, 20%, 30% and 50%
Buckwheat flour from
roasted groats
Dough making
Dough making
Flour, salt, yeasts and water
Cutting dough into pieces (250g)
Shaping into loaf
Dough rising at 37°C, 25min
Baking
250°C, 30min
Baking
250°C, 30min
Buckwheat
enhanced white
wheat breads
Reference
white wheat
bread
Baking
250°C, 30min
Roasted buckwheat
enhanced white wheat
breads
4th International Conference and Exhibition on Food Processing & Technology
August 10-12, 2015 London, UK
PART II. RYE-BUCKWHEAT GINGER
CAKES ENRICHED WITH RUTIN
flour from husked
buckwheat
flour from roasted
buckwheat groats
Rye-buckwheat ginger cakes
with LOW addition of rutin
(2.5 mg of rutin in 50 g of product)
Rye-buckwheat ginger cakes
with MEDIUM addition of rutin
(12.5 mg rutin in 50 g of product)
Rye-buckwheat ginger cakes
with HIGH addition of rutin
(25 mg rutin in 50 g of product)
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August 10-12, 2015 London, UK
FORMULATION OF RYE-BUCKWHEAT GINGER CAKES WITH RUTIN
buckwheat honey 50 g
sugar
20 g
baking soda
3g
butter
25 g
spice mix
2g
buckwheat honey 50 g
sugar
20 g
baking soda
3g
butter
25 g
spice mix
2g
rye flour
100 g
CONTROL
rye flour
70 g
flour from roasted
buckwheat groats
30 g
rye flour
70 g
flour from husked
buckwheat
30 g
Dought making
Baking
180 ⁰C 18 minutes
synthetic rutin
10 mg
50 mg
100 mg
synthetic rutin
10 mg
50 mg
100 mg
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THE IDEA
weight: 50 g
6 pieces
1 tablet
contains
25 mg of rutin
50 g of ginger cakes with high amount of rutin corresponds to one tablet of rutin
4th International Conference and Exhibition on Food Processing & Technology
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PART III. INNOVATIVE BREADS ENHANCED WITH NATURAL
INGREDIENTS CONTAINING POLYPHENOLS
IN-1: spelt bread with cherry (P.410947, 2015, PL),
IN-2: mixed wheat/rye bread enhanced with roasted buckwheat flour
(P.411732, 2015, PL)
IN-3: mixed wheat/rye bread enriched with dry onion skins
(P.411555, 2015, PL)
IN-4: sourdough fermented rye bread enriched with roasted buckwheat hull
(P.411731, 2015, PL)
IN-5: roll type graham with raw buchwheat hull
(P.410730, 2014, PL)
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METHODS
HOW DID WE PERFORM THE IN VITRO STUDY?
MODEL SYSTEMS:
BSA + glucose
BSA + methylglyoxal
side-product of several
metabolic pathways
(intermediate ot threonine
catabolism, lipid peroxidation
and glycolysis)
Methylglyoxal is proven to be the most important glycation agent
(forming AGEs)
4th International Conference and Exhibition on Food Processing & Technology
August 10-12, 2015 London, UK
Glucose
Protein-NH2
Glycation
Glycoxydation
Oxydative stress
Schiff base
Amadori products
Glyoxal
3-Deoxyglucosone
Protein-NH2
Intermediary glycation products
Methylglyoxal…
Protein-NH2
Advanced Glycation End-products
aminoguanidine
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HOW DID WE DETERMINE AGES
FORMATION/INHIBITION?
FLUORESCENCE
ANALYSIS
4th International Conference and Exhibition on Food Processing & Technology
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fluorescence of the solution with inhibitors
% inhibition = {1 – (------------------------------------------------------------------)} x 100%
fluorescence of the solution without inhibitors
aminoquanidine (AG) 1 mM was used as positive control
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Measurement of the inhibitory effect of buckwheat enhanced bakery
products on the formation of advanced glycation end products (AGEs)
BREAD/CAKE EXTRACTS
(1g/5mL 67% MeOH; 37°C; 1h)
EVAPORATION TO DRYNES
(40°C)
BUFFER BREAD/CAKE EXTRACTS
(dissolved in 5mL of phosphate buffer 0,1M pH 7,4)
BSA-GLUCOSE
BSA-MGO
Incubation (55°C; 40h)
Fluorescence intensity (λEX-330nm; λEM-410nm)
Incubation (37°C; 168h)
Fluorescence intensity (λEX-320nm; λEM-420nm)
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RESULTS
4th International Conference and Exhibition on Food Processing & Technology
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PART I. BUCKWHEAT ENHANCED WHEAT BREADS
4th International Conference and Exhibition on Food Processing & Technology
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Rutin content
Quercetin content
buckwheat flour from
roasted groat
buckwheat flour “BIO”
white wheat flour
Ru and Q
white wheat flour
Ru and Q
4th International Conference and Exhibition on Food Processing & Technology
August 10-12, 2015 London, UK
The inhibitory effect of buckwheat enhanced wheat bread extracts on the
formation of AGEs
BSA-Glucose model system
BSA-MGO model system
Inhibition AGEs vs Ru r = 0.86 (BIO)
Inhibition AGEs vs Ru r = 0.94 (BIO)
Inhibition AGEs vs Ru r = 0.89
(ROASTED)
Inhibition AGEs vs Ru r = 0.88
(ROASTED)
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PART II. RYE-BUCKWHEAT GINGER CAKES ENRICHED WITH RUTIN
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Determination of rutin content
Ginger cakes based on flour from buckwheat flour
Ru [ug/g DM]
1000
829.79
800
467.45
600
RUTIN
400
200
17.62
44.34
98.19
0
control
rye-buckwheat LOW amount
without rutin
of rutin
MEDIUM
amount of
rutin
HIGH amount
of rutin
4th International Conference and Exhibition on Food Processing & Technology
August 10-12, 2015 London, UK
Determination of rutin content
Ru [ug/g DM]
Ginger cakes formulated on flour from milled roasted buckwheat groats
1000
900
800
700
600
500
400
300
200
100
0
787.23
470.13
RUTIN
151.91
17.62
control
44.64
rye-buckwheat LOW amount
without rutin
of rutin
MEDIUM
amount of
rutin
HIGH amount
of rutin
4th International Conference and Exhibition on Food Processing & Technology
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The inhibitory effect of buckwheat ginger cake extracts on the formation of AGEs
[%]
Bovine serum albumin -glucose system (BSA/glucose)
79.68
80
70
60
47.62
50
40
26.07
30
33.02 26.09
34.08
33.54
21.24
28.81
36.38
20
10
0
aminoguanidyne
control
rye-buckwheat
gingercake
without rutin
LOW amount of
rutin
MEDIUM
amount of rutin
HIGH amount of
rutin
ginger cakes based on flour from husked buckwheat
Rutin vs BSA /Glu r = 0.47
ginger cakes formulated on flour from milled roasted buckwheat groats
Rutin vs BSA /Glu r = 0.93
4th International Conference and Exhibition on Food Processing & Technology
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The inhibitory effect of buckwheat ginger cake extracts on the formation of AGEs
[%]
Bovine serum albumin- methylglyoxal system (BSA/
MGO)
80
70
65.94
58.82
60
64.85 58.8
62.65
72.42
63.81
57.42
60.48
63.83
50
40
30
20
10
0
aminoguanidine
control
rye-buckwheat
gingercake
without rutin
LOW amount of
rutin
MEDIUM
amount of rutin
HIGH amount
of rutin
ginger cakes based on flour from husked buckwheat
Rutin vs BSA /MGO r= 0.22
ginger cakes formulated on flour from milled roasted buckwheat groats
Rutin vs BSA /MGO r= 0.96
4th International Conference and Exhibition on Food Processing & Technology
August 10-12, 2015 London, UK
PART III. INNOVATIVE BREADS ENHANCED WITH NATURAL
INGREDIENTS CONTAINING POLYPHENOLS
IN-1: spelt bread with cherry
IN-2: mixed wheat/rye bread enhanced with roasted buckwheat flour
IN-3: mixed wheat/rye bread enriched with dry onion skins
IN-4: sourdough fermented rye bread enriched with roasted buckwheat hull
IN-5: roll type graham with raw buchwheat hull
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Total polyphenols
Quercetin content
XIC of -MRM (30 pairs): 193.000/134.100 Da ID: k.ferulowy from Sample 208 (P1 2 W 5x) of chleby.wiff (Turbo Spray)
XIC of -MRM (30 pairs): 301.100/151.100 Da ID: Q from Sample 96 (P2 M1 25% 5x) of chleby.wiff (Turbo Spray)
Max. 9.5e4 cps.
5.2e6
5.0e6
2.5e5
2.4e5
4.8e6
2.3e5
4.6e6
2.2e5
4.4e6
2.1e5
4.2e6
2.0e5
4.0e6
1.9e5
3.8e6
1.8e5
3.6e6
1.7e5
3.4e6
1.6e5
3.2e6
I n te n s i ty , c p s
I n te n s i ty , c p s
3.0e6
2.8e6
2.6e6
2.4e6
2.2e6
1.5e5
1.4e5
1.3e5
1.2e5
1.1e5
1.0e5
2.0e6
9.0e4
1.8e6
1.6e6
8.0e4
1.4e6
7.0e4
1.2e6
6.0e4
1.0e6
5.0e4
8.0e5
4.0e4
6.0e5
3.0e4
4.0e5
1.41
2.0e4
2.0e5
0.0
0.0
Max. 5.6e4 cps.
1.34
0.97 1.05
0.2
0.4
0.6
0.8
1.0
1.2
1.0e4
1.57
1.4
1.6
Time, min
1.8
2.0
2.2
2.4
2.6
2.8
Profile of phenolics acids determined by HPLC-MS/MS
0.0
0.0
0.2
0.4
0.6
0.8
1.0
1.2
1.4
1.6
Time, min
2.0
2.2
2.4
2.6
2.8
Profile of flavonoids determined by HPLC-MS/MS
sinapic acid
p-coumaric acid
m-coumaric acid
caffeic acid
Isoferrulic acid
quercetin
quercetin glycosides
rutin
Content of phenolic acids and flavonoids
1.8
4th International Conference and Exhibition on Food Processing & Technology
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The inhibitory effect of innovative breads enhanced with natiral ingriedients
containing polyphenols on the formation of AGEs
BSA-Glucose model system
(phenolic acids + flavonoids) vs BSA /Glu r= 0.96
Q vs BSA /Glu r= 0.95
Total phenolic compounds by Follin
reagent
TPC vs BSA /Glu r= 0.96
4th International Conference and Exhibition on Food Processing & Technology
August 10-12, 2015 London, UK
The inhibitory effect of innovative breads enhanced with natiral
ingriedients containing polyphenols on the formation of AGEs
BSA-MGO model system
(phenolic acids + flavonoids) vs BSA /Glu r= 0,89
Q vs BSA /Glu r= 0,89
Total phenolic compounds by Follin reagent
TPC vs BSA /Glu r= 0,89
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quercetin - Q
3,3’,4’,5,7–pentahydroksyflavon
185 – 1917 mg Q/kg WM
OH
2'
O
7
6
5'
O
7
6'
3
5
2'
4'
B
2
3'
OH
3'
6
O
C
5
O
3'
2'
7
6
O
A
C
5
O
H
O
4'
5'
2
6'
3
O
H
2
3
4'
5'
6'
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SUMMARY
Extracts from buckwheat enhanced wheat breads, formulated on white wheat
flour and flour from roasted buckwheat groats showed higher inhibitory effects
against AGEs formation than those formulated on white wheat flour and
buckwheat flour “BIO”.
Rye-buckwheat ginger cakes with high rutin addition showed the highest
inhibitory activity against AGEs formation as compared to ginger cakes with low
and medium rutin supplementation.
Mixed wheat/rye bread enriched with dry onion skins showed the highest
inhibitory activity against AGEs formation amongs innovative breads.
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CONCLUSIONS
This study showed possibility of formulation buckwheat derived bakery
products with effective inhibition the formation of AGEs in vitro.
This further supports that buckwheat derived bakery products may be
beneficial food choice for diabetics as AGEs have been implicated in
the pathogenesis of various diabetic complications and other diseases.
The rich source of polyphenols such as buckwheat flours, buckwheat
hull or dry onion skins should be considered as a new ingredients in
innovative breads for diabetics.
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ISSN 1230-0322
Published by the Division of
Food Science, Institute of
Animal Reproduction and
Food Research of the Polish
Academy of Sciences
Impact Factor = 0.643
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