antioxidant and functional properties of novel quercetin-enriched lecithin

Antioxidant and Functional Antioxidant and Functional Properties of Novel Quercetin-Properties of Novel Quercetin-

enriched Lecithinenriched LecithinDr. 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)

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


- 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 present 1- 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 outer 2- 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 they It 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.


Lipid-soluble Lipid-soluble phenolics might be phenolics might be the main reason of the main reason of

the health promoting the health promoting properties of olive oilproperties of olive oil

!!! !!!


1- Can we overcome those problems 1- Can we overcome those problems and enhance functional properties of and enhance functional properties of

lecithin and flavonoids by lecithin and flavonoids by mixing/binding them !?mixing/binding them !?

2- Can we produce novel formulations 2- Can we produce novel formulations (functional foods, nutraceuticals.. etc)(functional foods, nutraceuticals.. etc) with certain phenolics-enriched polar with certain phenolics-enriched polar

lipids !?lipids !?


1-To prepare phenolics-enriched lecithin using commercial polar lipids 1-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 in 2-To study the antioxidant properties of quercetin-enriched lecithin in lipophilic model system (triolein).lipophilic model system (triolein).

3- To investigate the 3- To investigate the biological biological properties (antimicrobial and antiviral) properties (antimicrobial and antiviral) of the new formulations.of the new formulations.

Objectives of The WorkObjectives of The Work


-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

Hypotheses Hypotheses

Lecithin + Lecithin + QuercetinQuercetin

Solubilization using different Solubilization using different solvents under different conditionssolvents under different conditions

Recovery of Recovery of Flavo-lipidsFlavo-lipids


Preparation of Quercitin-enriched LecithinPreparation of Quercitin-enriched Lecithin

Lecithin + Lecithin + QuercetinQuercetin(1:1, w/w)(1:1, w/w)

Solubilization in ethyl acetate Solubilization in ethyl acetate (1:10, w/v) at 40 °C for 30 min.(1:10, w/v) at 40 °C for 30 min.

Recovery of Recovery of Flavo-lipidsFlavo-lipids(Freeze drying)(Freeze drying)

Ramadan MF (2008) Food Science and Technology/LWT 41:581-587

Triolein Model System and Oxidation Experiment Triolein Model System and Oxidation Experiment

Quercetin-enriched lecithin + TrioleinQuercetin-enriched lecithin + Triolein))0.250.25 g/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 stability11 - -Peroxide valuePeroxide value

22 - -UV absorptivity values at 232 and 270 nmUV absorptivity values at 232 and 270 nm33 - -Radical scavenging activity (DPPH radical)Radical scavenging activity (DPPH radical)..


Antioxidant Properties of Quercitin-enriched Antioxidant Properties of Quercitin-enriched Lecithin in a Triolein Model SystemLecithin in a Triolein Model System


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)






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


Abs

orpt

ivity

232

nm







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


Abs

orpt

ivity

at 2

70 n

m







Scavenging effect after 60 min incubation time of triolein models on DPPH Scavenging 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


Rem

aini

ng D

PPH

%

Triolein







Antibacterial Activity of Quercetin, Lecithin and Antibacterial Activity of Quercetin, Lecithin and Quercetin-enriched Lecithin Formulations Against Quercetin-enriched Lecithin Formulations Against

E. coliE. coli, , P. aeruginosaP. aeruginosa, , B. subtilisB. subtilis and and St. aureusSt. aureus..

Ramadan MF, Askar MA (2009) Journal of Food Biochemistry, In press.

Compound/ formulation

µg/mLDiameter of inhibition zone (mm)a

Gram-negativeGram-positiveE. coliP. aeruginosaB. subtilisSt. aureus

Quercetin (Qu)2000

15.6615.6613.013.019.019.015.315.3

Lecithin (Le)Lecithin (Le)2000

9.679.6710.310.39.009.008.338.33

Qu-Le (1:99, w/w)2000

18.618.617.617.619.619.617.017.0

Qu-Le Qu-Le (3:97, w/w)(3:97, w/w)2000

23.323.324.324.327.027.022.022.0

Minimum Inhibitory Concentration Minimum Inhibitory Concentration (MIC)(MIC) of Quercetin, of Quercetin, Lecithin and Quercetin-enriched Lecithin Formulations Lecithin and Quercetin-enriched Lecithin Formulations

Against Against E. coliE. coli, , P. aeruginosaP. aeruginosa, , B. subtilisB. subtilis and and St. aureusSt. aureus..


Compound/ formulation

MIC (µg/mL)

E. coliP. aeruginosaB. subtilisSt. aureus

Quercetin (Qu)1000100012501250750750750750

Lecithin (Le)Lecithin (Le)17501750175017501750175015001500

Qu-Le (1:99, w/w)10001000750750750750750750

Qu-Le (3:97, w/w)Qu-Le (3:97, w/w)500500500500250250250250

Antiviral activity of quercetin, lecithin and quercetin-enriched Antiviral activity of quercetin, lecithin and quercetin-enriched lecithin formulation (3:97 w/w) against Hepatitis A Virus lecithin formulation (3:97 w/w) against Hepatitis A Virus

(HAV) Strain(HAV) Strain


0

10

20

30

40

50

60

70

80

% Inhibition

Lecithin Querectin Querectin-enriched lecithin(3:97, w/w)

Conclusions and Upcoming ResearchConclusions and Upcoming Research

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

We need toWe need to1-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 be unctional 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 synergism Biological 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 the absorbed 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 . .

. . One of the old cities in Egypt One 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

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

antioxidant and functional properties of novel quercetin-enriched lecithin

Health & Medicine