Lipid-soluble phenolics might be the main reason of the health promoting properties of olive oil !!!

1. Antioxidant and Functional PropertiesAntioxidant and Functional Properties
of Novel Quercetin-enriched Lecithinof Novel Quercetin-enriched Lecithin
Dr. Mohamed Fawzy Ramadan-HassanienDr. Mohamed Fawzy Ramadan-Hassanien
Assistant ProfessorAssistant Professor,,
Biochemistry Department, Faculty of Agriculture, Zagazig University, EgyptBiochemistry Department, Faculty of Agriculture, Zagazig University, Egypt..
100th
AOCS Annual Meeting & Expo May 3-6, 2009 (Orlando, FLorida(

2. Phosphatidylcholine, with choline as
polar head group, is the main
glycerophospholipid in lecithin.
O P O
O−
O
H2C
CH
H2C
OCR1
O O C
O
R2
CH2 CH2 N CH3
CH3
CH3
+
phosphatidylcholine
-Lecithin is the main by-product of vegetable oil industry which
usually a mixture PC (13-18%), PE (10-15%), and PI (10-
15%), and is used in a wide variety of food and industrial
applications.
Antioxidative properties of lecithin have been attributed to:
1-Synergism between phospholipids and tocopherol,
2-Chelating of pro-oxidant metals by phosphate groups,
3-Formation of Maillard-type products between amino
phospholipids and oxidation products,
4-Action as an oxygen barrier between oil and air interfaces.
Lecithin (Phospholipids): Properties and ProblemsLecithin (Phospholipids): Properties and Problems
Problems in Food Industry:Problems in Food Industry:
-Two crucial PUFA of phospholipids [linoleic acid (C18:2) and linolenic acid (C18:3)] are sensitive sites
for autoxidation. Thus, lecithin is easily oxidized and these oxidative processes modify phospholipids'
properties responsible for their antioxidative activities. The products quality and their self-life could be
affected harmfully.
Lecithin properties need to be enhanced to meet the growing applications in different fieldsLecithin properties need to be enhanced to meet the growing applications in different fields
100th
AOCS Annual Meeting & Expo May 3-6, 2009 (Orlando, FLorida(

3. - Flavonoids comprise many subclasses such as the flavans,
flavanones, flavones, anthocyanins, etc . . .
- Phenolics have been attributed with positive
pharmacological properties such as having antimutagenic
and anticancerogenic effects as well as being antioxidants.
Flavonoids: Properties and problemsFlavonoids: Properties and problems
O
O
HO
OH
OH
OH
OH
Quercetin, the most ubiquitous
flavonoid, a 3,5,7,3′,4′-pentahydroxy
flavone
Bioavailability Problems:Bioavailability Problems:
-Poor absorption of flovonoids!!!Poor absorption of flovonoids!!!
1- Bacterial degradation of the phenol moiety of the molecule and a complex formation with other substances present1- Bacterial degradation of the phenol moiety of the molecule and a complex formation with other substances present
in the gastrointestinal tract thus preventing absorption.in the gastrointestinal tract thus preventing absorption.
2- Flavonoid molecules have poor miscibility with lipids, which limited their ability to pass across the lipid-rich outer2- Flavonoid molecules have poor miscibility with lipids, which limited their ability to pass across the lipid-rich outer
membranes of the small intestine.membranes of the small intestine.
It has been often stated that flavonoids present in foods can not be absorbed from the intestine if theyIt has been often stated that flavonoids present in foods can not be absorbed from the intestine if they
are bound to sugars as glycosides.are bound to sugars as glycosides.
100th
AOCS Annual Meeting & Expo May 3-6, 2009 (Orlando, FLorida(

4. Lipid-solubleLipid-soluble
phenolics might bephenolics might be
the main reason ofthe main reason of
the health promotingthe health promoting
properties of olive oilproperties of olive oil
!!!!!!
100th
AOCS Annual Meeting & Expo May 3-6, 2009 (Orlando, FLorida(

5. 1- Can we overcome those problems1- Can we overcome those problems
and enhance functional properties ofand enhance functional properties of
lecithin and flavonoids bylecithin and flavonoids by
mixing/binding them !?mixing/binding them !?
2- Can we produce novel formulations2- Can we produce novel formulations
(functional foods, nutraceuticals.. etc)(functional foods, nutraceuticals.. etc)
with certain phenolics-enriched polarwith certain phenolics-enriched polar
lipids !?lipids !?
100th
AOCS Annual Meeting & Expo May 3-6, 2009 (Orlando, FLorida(

6. 1-To prepare phenolics-enriched lecithin using commercial polar lipids1-To prepare phenolics-enriched lecithin using commercial polar lipids
and phenolic substances.and phenolic substances.
2-To study the antioxidant properties of quercetin-enriched lecithin in2-To study the antioxidant properties of quercetin-enriched lecithin in
lipophilic model system (triolein).lipophilic model system (triolein).
3- To investigate the3- To investigate the biologicalbiological properties (antimicrobial and antiviral)properties (antimicrobial and antiviral)
of the new formulations.of the new formulations.
Objectives of The WorkObjectives of The Work
100th
AOCS Annual Meeting & Expo May 3-6, 2009 (Orlando, FLorida(

7. -Phenolics-enriched lecithin could be
prepared by reacting a flavonoid with
phospholipids (e.g., PC, PE and/or
lecithin) in a suitable solvent.
-After solubilization, the complex
formulation could be isolated by
removing the solvent under vacuum, or
by lyophilization.
-New formulation is anticipated to be
lipophilic in character and soluble in
non-polar solvents
HypothesesHypotheses
Lecithin +Lecithin + QuercetinQuercetin
Solubilization using differentSolubilization using different
solvents under different conditionssolvents under different conditions
Recovery ofRecovery of Flavo-lipidsFlavo-lipids
100th
AOCS Annual Meeting & Expo May 3-6, 2009 (Orlando, FLorida(

8. Preparation of Quercitin-enriched LecithinPreparation of Quercitin-enriched Lecithin
Lecithin +Lecithin + QuercetinQuercetin
(1:1, w/w)(1:1, w/w)
Solubilization in ethyl acetateSolubilization in ethyl acetate
(1:10, w/v) at 40 °C for 30 min.(1:10, w/v) at 40 °C for 30 min.
Recovery ofRecovery of Flavo-lipidsFlavo-lipids
(Freeze drying)(Freeze drying)
Ramadan MF (2008( Food Science and Technology/LWT 41:581-587

9. Triolein Model System and Oxidation ExperimentTriolein Model System and Oxidation Experiment
Quercetin-enriched lecithin + TrioleinQuercetin-enriched lecithin + Triolein
((0.250.25g/100 g and 0.50 g/100 gg/100 g and 0.50 g/100 g))
Accelerated oxidation experimentAccelerated oxidation experiment
(60 °C for 5, 10 and 15 days).(60 °C for 5, 10 and 15 days).
Monitoring oxidative stabilityMonitoring oxidative stability
11--Peroxide valuePeroxide value
22--UV absorptivity values at 232 and 270 nmUV absorptivity values at 232 and 270 nm
33--Radical scavenging activity (DPPH radicalRadical scavenging activity (DPPH radical).).
Ramadan MF (2008( Food Science and Technology/LWT 41:581-587

10. Antioxidant Properties of Quercitin-enrichedAntioxidant Properties of Quercitin-enriched
Lecithin in a Triolein Model SystemLecithin in a Triolein Model System
Ramadan MF (2008( Food Science and Technology/LWT 41:581-587
Changes in peroxide values of triolein models during oven testChanges in peroxide values of triolein models during oven test
0
2
4
6
8
10
12
14
16
18
0 5 10 15
Storage period (day)
meq/kg
Triolein
Model contains Q-L mixture (0.25 g/100g)
Model contains Quercetin (0.25 g/100g)
Model contains lecithin (0.25 g/100g)
Model contains Q-L mixture (0.50 g/100g)
Model contains Quercetin (0.50 g/100g)
Model contains lecithin (0.50 g/100g)

11. Antioxidant Properties of Quercitin-enrichedAntioxidant Properties of Quercitin-enriched
Lecithin in a Triolein Model SystemLecithin in a Triolein Model System
Ramadan MF (2008) Food Science and Technology/LWT 41:581-587
Absorptivity at 232 nm of triolein models during oven testAbsorptivity at 232 nm of triolein models during oven test
2.70
2.75
2.80
2.85
2.90
2.95
3.00
3.05
3.10
3.15
0 5 10 15
Storage period (day)
Absorptivity232nm
Model contains Q-L mixture (0.25 g/100g)
Model contains lecithin (0.25 g/100g)
Model contains Q-L mixture (0.50 g/100g)
Model contains lecithin (0.50 g/100g)

12. Antioxidant Properties of Quercitin-enrichedAntioxidant Properties of Quercitin-enriched
Lecithin in a Triolein Model SystemLecithin in a Triolein Model System
Ramadan MF (2008) Food Science and Technology/LWT 41:581-587
Absorptivity at 270 nm of triolein models during oven testAbsorptivity at 270 nm of triolein models during oven test
0.5
0.7
0.9
1.1
1.3
1.5
1.7
1.9
2.1
0 5 10 15
Storage period (day)
Absorptivityat270nm
Model contains Q-L mixture (0.25 g/100g)
Model contains lecithin (0.25 g/100g)
Model contains Q-L mixture (0.50 g/100g)
Model contains lecithin (0.50 g/100g)

13. Antioxidant Properties of Quercitin-enrichedAntioxidant Properties of Quercitin-enriched
Lecithin in a Triolein Model SystemLecithin in a Triolein Model System
Ramadan MF (2008) Food Science and Technology/LWT 41:581-587
Scavenging effect after 60 min incubation time of triolein models on DPPHScavenging effect after 60 min incubation time of triolein models on DPPH
radical as measured by changes in absorbance values at 515 nmradical as measured by changes in absorbance values at 515 nm
40
50
60
70
80
90
100
0 5 10 15
Storage period (day)
RemainingDPPH%
Triolein
Model contains Q-L mixture (0.25 g/100g)
Model contains Quercetin (0.25 g/100g)
Model contains lecithin (0.25 g/100g)
Model contains Q-L mixture (0.50 g/100g)
Model contains Quercetin (0.50 g/100g)
Model contains lecithin (0.50 g/100g)

14. Antibacterial Activity of Quercetin, Lecithin andAntibacterial Activity of Quercetin, Lecithin and
Quercetin-enriched Lecithin Formulations AgainstQuercetin-enriched Lecithin Formulations Against
E. coliE. coli,, P. aeruginosaP. aeruginosa,, B. subtilisB. subtilis andand St. aureusSt. aureus..
Ramadan MF, Askar MA (2009) Journal of Food Biochemistry, In press.
Compound/
formulation
µg/mL Diameter of inhibition zone (mm)a
Gram-negative Gram-positive
E. coli P. aeruginosa B. subtilis St. aureus
Quercetin (Qu) 2000 15.6615.66 13.013.0 19.019.0 15.315.3
Lecithin (LeLecithin (Le)) 2000 9.679.67 10.310.3 9.009.00 8.338.33
Qu-Le (1:99, w/w) 2000 18.618.6 17.617.6 19.619.6 17.017.0
Qu-LeQu-Le (3:97, w/w(3:97, w/w)) 2000 23.323.3 24.324.3 27.027.0 22.022.0

15. Minimum Inhibitory ConcentrationMinimum Inhibitory Concentration (MIC)(MIC) of Quercetin,of Quercetin,
Lecithin and Quercetin-enriched Lecithin FormulationsLecithin and Quercetin-enriched Lecithin Formulations
AgainstAgainst
E. coliE. coli,, P. aeruginosaP. aeruginosa,, B. subtilisB. subtilis andand St. aureusSt. aureus..
Ramadan MF, Askar MA (2009) Journal of Food Biochemistry, In press.
Compound/
formulation
MIC (µg/mL)
E. coli P. aeruginosa B. subtilis St. aureus
Quercetin (Qu) 10001000 12501250 750750 750750
Lecithin (LeLecithin (Le)) 17501750 17501750 17501750 15001500
Qu-Le (1:99, w/w) 10001000 750750 750750 750750
Qu-Le (3:97, w/wQu-Le (3:97, w/w)) 500500 500500 250250 250250

16. Antiviral activity of quercetin, lecithin and quercetin-enrichedAntiviral activity of quercetin, lecithin and quercetin-enriched
lecithin formulation (3:97 w/w) against Hepatitis A Viruslecithin formulation (3:97 w/w) against Hepatitis A Virus
(HAV) Strain(HAV) Strain
Ramadan MF, Askar MA (2009) Journal of Food Biochemistry, In press.
0
10
20
30
40
50
60
70
80
% Inhibition
Lecithin Querectin Querectin-enriched lecithin
(3:97, w/w)

17. Conclusions and Upcoming ResearchConclusions and Upcoming Research
100th
AOCS Annual Meeting & Expo May 3-6, 2009 (Orlando, Florida)
We need toWe need to
1-Prepare phenolic-enriched polar lipids using different techniques.
2-Study the impact of processing (e.g., thermal processing) on the properties and
stability of new formulations.
3-Determine the optimal concentration of quercetin–lecithin mixtures depending on
the application.
11--Quercetin-enriched lecithin was superior to native lecithin and quercetin as a stabilizing agentQuercetin-enriched lecithin was superior to native lecithin and quercetin as a stabilizing agent..
22--FFunctional and health promoting properties of commercial lecithin and plant extracts could beunctional and health promoting properties of commercial lecithin and plant extracts could be
significantly enhanced in different applicationssignificantly enhanced in different applications..
33--Biological activities of quercetin-enriched lecithin seems to be the result of the synergismBiological activities of quercetin-enriched lecithin seems to be the result of the synergism
between phospholipids and quercetin with antioxidative propertiesbetween phospholipids and quercetin with antioxidative properties..
44--Phenolics-enriched lecithinPhenolics-enriched lecithin, thanks to their lipophilic character, is expected to be perfectly, thanks to their lipophilic character, is expected to be perfectly
absorbed through oral administration and increase the therapeutic effectiveness of theabsorbed through oral administration and increase the therapeutic effectiveness of the
flavonoids both by oral or topical administrationflavonoids both by oral or topical administration..
55--Quercetin-enriched lecithin can be targeted for specific applications as functional foods,Quercetin-enriched lecithin can be targeted for specific applications as functional foods,
pharmaceuticals and cosmeticspharmaceuticals and cosmetics..

18. .. One of the old cities in EgyptOne of the old cities in Egypt
(about 4000 years old).(about 4000 years old).
. Population: 1 Million.. Population: 1 Million.
Zagazig: City and UniversityZagazig: City and University
. Zagazig University was
established 1974 and it include 20
colleges.
. Faculty of Agriculture was also
established 1974 and it consist of
16 departments.
www.zu.edu.eg

19. 100th
AOCS Annual Meeting & Expo May 3-6, 2009 (Orlando, Florida)