Phenolipids

HO

OH

HO O

OH :Phenolipids
O O
Novel Phenolics Enriched Lecithin
H
For Functional And Pharmaceutical
O
Applications
H2C O P O CH
2

O

.Mohamed Fawzy Ramadan Hassanien, Ph.D
,Associate Professor
.Biochemistry Department, Faculty of Agriculture, Zagazig University, Egypt

101 st(Annual Meeting & Expo, May 16-19, 2010 (Phoenix, Arizona, USA

Lecithin (Phospholipids): Properties and Problems
O
-Lecithin is usually a mixture PC (13-18%), PE (10-15%), H2C O C R2
and PI (10-15%). O

HC O C R1
- Phospholipids have many health-promoting properties O CH3

(e.g., antioxidative properties) and used in a wide H2C O
+
P O CH2 CH2 N CH3

variety of food and industrial applications. O
-
CH3

Phosphatidylcholine, with choline as polar
.head group
Auto-oxidation Problem

-PUFA of phospholipids [e.g., linolenic acid (C18:3)] are sensitive sites for autoxidation. Therefore,
lecithin is easily oxidized which affect harmfully the products quality and their self-life.

Lecithin properties need to be enhanced to meet the growing applications in different fields


Flavonoids: Properties and Problems
HO
-Flavonoids comprise many subclasses such as flavans,
OH
flavanones, flavones, anthocyanins, etc . . .
HO O
-Phenolic compounds have many health-promoting
properties (e.g., antimutagenic and anticancerogenic OH
effects) as well as being antioxidants. OH O

Quercetin,
Bioavailability Problem a 3,5,7,3′,4′-pentahydroxy flavone

-Poor absorption of flovonoids could be due to:
1- Bacterial degradation of phenol moiety and a complex formation with other substances which prevent absorption.
2- Flavonoids have poor miscibility with lipids, which limited their ability to pass across the lipid-rich membranes of
small intestine.

Phenolic compounds bioavailability need to be improved to magnify their health-promoting effects


1- Can we overcome those problems
and enhance functional properties of
lecithin and flavonoids by
mixing/binding them !?

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


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


Hypotheses
-Phenolipids could be prepared by Lecithin
reacting flavonoids with phospholipids + Phenolic compounds
(e.g., quercetin and rutin)
(e.g., PC and/or lecithin) in a suitable
solvent.

-After solubilization, the complex
Solubilization using different
formulation could be isolated by solvents under different conditions
removing the solvent under vacuum, or
by lyophilization.

-New formulation is anticipated to be
lipophilic in character and soluble in Recovery of Phenolipids
non-polar solvents.


Liposoms and Phenolipids

HO

-Liposomes OH

are formed by mixing water-soluble
HO O
substances with phospholipids without
forming chemical bonds. OH

O

H

-Phenolipids O

unlike liposomes, result H C O theP
from
2 O CH2

reaction of phospholipids with selected
O
phenolics. They are lipophillic
substances freely soluble in some
solvents and in fats.


Objectives of The Work

1-To prepare phenolics-enriched lecithin (Phenolipids) using
commercial polar lipids and phenolic substances.

2-To study the antioxidant properties of phenolics-enriched
lecithin in different lipophilic model systems (e.g., triolein).

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


Preparation of Phenolipids
(e.g., Quercitin-enriched Lecithin)
Lecithin + Quercetin
(1:1, w/w)

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

Recovery of Phenolipids
(Freeze drying)

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

Antiradical Properties of Phenolipids
100 Phenolipids
90

80

70
% Inhibition

60

50

40

Phospholipids
30

20
Phenolics
10

0
Lecithin PC Querectin Rutin (Ru) QMG Qu/Le Rutin/Le QMG/Le Qu/PC Rutin/PC QMG/PC
(Le) (Qu)

Scavenging effect after 60 min incubation time of different individual bioactive
compounds and Phenolipids on DPPH radical


Oxidation in Triolein Model System

Quercetin-enriched lecithin + Triolein
(g/100 g and 0.50 g/100 g 0.25)

Accelerated oxidation experiment
(60 °C for 5, 10 and 15 days).

Monitoring oxidative stability
Peroxide value -1
UV absorptivity at 232 and 270 nm -2
.(Radical scavenging activity (DPPH radical -3


Antioxidant Properties of Quercitin-enriched
Lecithin in a Triolein Model System
18
Triolein
16
Model contains Q-L mixture (0.25 g/100g)

Model contains Quercetin (0.25 g/100g)
14
Model contains lecithin (0.25 g/100g)
12

10
Model contains Quercetin (0.50 g/100g) L
meq/kg

8

Q
6

4 Q-L

2

0
0 5 10 15

Storage period (day)

Changes in peroxide values of triolein models during oven test

3.15
3.10
L
3.05 Model contains Q-L mixture (0.50 g/100g)

3.00 Model contains lecithin (0.50 g/100g)
Absorptivity 232 nm

2.95
Q-L
2.90

2.85

2.80

2.75

2.70
0 5 10 15


Absorptivity at 232 nm of triolein models during oven test

L
2.1

1.9

1.7
1.5 Model contains Q-L mixture (0.50 g/100g)
Absorptivity at 270 nm

1.3

Q-L
1.1

0.9

0.7

0.5
0 5 10 15

Absorptivity at 270 nm of triolein models during oven test

100 Triolein


90 Model contains Quercetin (0.25 g/100g)

L
80 Model contains Q-L mixture (0.50 g/100g)
Remaining DPPH%

Model contains Quercetin (0.50 g/100g)
70
Q

60

Q-L
50

40
0 5 10 15

Scavenging effect after 60 min incubation time of triolein models on DPPH
radical as measured by changes in absorbance values at 515 nm

Antibacterial Activity of Quercetin, Lecithin and
Quercetin-enriched Lecithin Formulations Against
E. coli, P. aeruginosa, B. subtilis and St. aureus.

/ Compound µg/mL Diameter of inhibition zone (mm)a
formulation
Gram-negative Gram-positive
E. coli P. aeruginosa B. subtilis St. aureus

(Quercetin (Qu 2000 15.66 13.0 19.0 15.3
(Lecithin (Le 2000 9.67 10.3 9.00 8.33
Qu-Le((1:99, w/w 2000 18.6 17.6 19.6 17.0
Qu-Le((3:97, w/w 2000 23.3 24.3 27.0 22.0

Ramadan MF, Askar MA (2009( Journal of Food Biochemistry 33: 557-571

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

80

70

60

50

% Inhibition 40
30

20

10

0
Lecithin Querectin Querectin-enriched lecithin
(3:97, w/w)

Ramadan MF, Askar MA (2009( Journal of Food Biochemistry 33: 557-571

Conclusions
-1Phenolipids are superior to native lecithin and/or phenolic
.compounds as a stabilizing agent
HO

OH
F -2unctional and health promoting properties of lecithin and
phenolic compounds could be greatly enhanced in different HO O

.applications
OH

O O
-3 Biological activities ofPhenolipids seems to be the result
of the synergism between phospholipids and phenolics with H

.antioxidative properties
O
-4Phenolics-enriched lecithin, thanks to their lipophilic
H2C O P O CH
character, is expected to be perfectly absorbed through oral 2

administration that increase the therapeutic effectiveness of O

.the flavonoids

-5Phenolipids can be targeted for specific applications as
.functional foods, pharmaceuticals and cosmetics

Upcoming Research

We need to
Prepare-1Phenolipids. using different techniques

Study the impact of processing )e.g., thermal processing( on-2
. the properties and stability ofPhenolipids

Determine the optimal concentration of-3Phenolipids
.depending on the application


Zagazig: City and University

. One of the old cities in Egypt
(about 4000 years old).
. Population: 1 Million.

. Zagazig University was
established 1974.

. Faculty of Agriculture established
1974 including 16 departments.

www.zu.edu.eg

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