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Untersuchung zur Zusammensetzung der
Lipide exotischer Ölsaaten
Investigation on Lipid Composition of
Exotic Oilseeds
Mohamed Fawzy Ramadan Hassanien
19.02.2004
1- The production of oil plants takes the third place in world production after starch plants and fruits.
2- More than 90% of the oil plants are produced in the tropical and subtropical areas.
4- The major oil crops of international importance: i.e., soybean (Glycine max), oil palm (Elaeis guineenis), rapeseed (Brassica spp.), sunflower (Helianthus
annuus), cottonseed (Gossypium spp.), and groundnut (Arachis
hypogaeo), together accounting for about 84% of world vegetable oil production.
Vegetable Oils : Production and Consumption .
World production of fats and oils
Animal
25%
Vegetable
75%
World consumption of fats and oils
Animal feed
7% Chemical
industry
13%
Edible uses
80%
Information on Black Cumin, Coriander and Niger Oilseeds
Black cumin
(Nigella sativa L.)
Family Ranonculaceae
Coriander
(Coriandrum sativum L.)
Family Umbelliferea
Niger
(Guizotia abyssinica Cass).
Family Compositae
Country of
source:
Mediterranean countries
and India.
Mediterranean countries, Eastern
Europe, and India.
-Ethiopia: (50-60% of total
production).
-India (2% of total production).
World Production: Not available 100 ton per year 400.000 ton per year (not
involved in the world oilseeds
trade).
Uses of oilseeds
and/or seed oils:
1- Edible uses: Sweet dish,
pastry, flavoring of food,
stomachic, carmanitive, and
diuretic agent.
2- Medicinal uses:
Antibacterial, Antifungal,
Antineoplastic,
Antihelmenthic.
1- Edible uses: Ingredient of curry
powder, Flavoring agent of certain
alcoholic beverages.
2-Industrial uses: Coriander produce
a high petroselinic acid of potential
uses (fine chemicals, softeners,
soaps, emulsifiers and nylon).
1- Edible uses.
2- Manufacture of soap and
paints.
3- Lubricant of illuminant.
4- Defatted Protein-rich meal
used as feed or fuel.
Total lipids
(fresh weight):
40% 30% 30-40%
Goals of The Study
1. To analyze the crude seed oils, their fractions and
their bioactive compounds.
2. To compare the Radical Scavenging Activity
(RSA) of the crude oils and their fractions and
to study the effect of minor components in oils,
especially polar lipids, on their RSA.
3. To assess oxidative stability of both crude and
stripped crude seed oils and to evaluate the
efficacy of a combination of polar lipids, in
delaying the oxidation of crude oils.
Adaptation of fast methods
Health Impact
Information for the Market
Black cumin, coriander and niger seed oils have been part of a diet in
many parts of the world and their consumption is also becoming
increasingly popular in the non-producer countries. However,
information on their composition and bioactives is limited.
Black cumin From Turkey
Oilseeds
Coriander From Hungary
Niger
From India
Grounding
(Particle size = 1-2 mm)
Extraction of crude seed oils
using n-hexane or
Chloroform:Methanol (2:1, v/v)
Fatty acid methyl esters
GLC/FID
Saponification
Phytosterols
GLC/FID
Experimental
Procedures
Fat-soluble vitamins
NP-HPLC/UV
Column Chromatography
(Silica gel 60)
Chloroform Acetone Methanol
Neutral lipids TLC and GLC
Glycolipids HPLC/UV, TLC
and GLC
Phospholipids HPLC/UV, TLC
and GLC
Radical Scavenging Activity ESR (galvinoxyl)
Photometric (DPPH radical).
Oxidative Stability Oven Test (21 days)
Peroxide Value, p-anisidine Value
UV (230 and 270 nm)
Levels of Fatty Acids in Crude Seed Oils
C1
6:0
C1
8:0
C1
8:1
n-1
2
C1
8:1
n-9
C1
8:2
n-6
C1
8:3
n-6
C2
0:2
n-6
C2
2:0
C2
2:1
n-9
C2
0:5
n-3
C2
2:6
n-3
0
10
20
30
40
50
60
70
Fatty acid
Black cumin seed oil
Coriander seed oil
Niger seed oilRelative
content
(%)
NP-HPLC/UV Analysis of Glycolipid Subclasses.
O
H O
H O
H O
C H 2 O H
O C H 2
CH-O-COR
CH-O-COR
O
H O
H O
C H 2 O H
O
O O
OH
OH
OH O - C O R 1
O - C O R 2
OH
O O R 1
N H - C O R 2
H O C H 2 O H
H O
H O H O
O
H O H O
H O
O
O R 1
R 2
O
H O
OH
C H 2 S O 3 H
H O O
O - C O R 1
O - C O R 2
Monogalactosyldiacylglycerol (MGDG)
Digalactosyldiacylglycerol (DGDG)
Cerebroside
(CER) R1= H, Steryl glucoside (SG)
R1= Acyl, Acylated steryl glucoside (ASG)
Sulfoquinovosyldiacylglycerol (SQD)
http://www.cyberlipid.org/glyt/glyt0008.htm
Compound
Black
cumin
Coriander Niger
seed
Acylated steryl glucoside (ASG) 9.95 25.1 38.5
Monoglucosyldiacylglycerol
(MGD)
7.88 nd nd
Steryl glucoside (SG) 9.45 34.9 29.5
Cerebroside (CER) 11.9 38.4 31.0
Diglucosyldiacylglycerol (DGD) 55.6 nd nd
Sulfoquinovosyldiacylglycerol
(SQD)
5.08 nd nd
NP-HPLC/UV Analysis of Phospholipid Subclasses.
CH2-O-R
CH-OR1 = -Form
O
CH2-O-P-O-R2 = -Form
OH
R2 = CH2-CH2-N
+(CH3)3 Phosphatidylcholine.
R2 = CH2-CH2-NH3+ Phosphatidylethanolamine.
R2 = CH2-CH(NH3)+ CO2H Phosphatidylserine.
R2 = (CH)6 (OH)5 Phosphatidylinositol.
Compound
Black
cumin
Coriander Niger seed
Phosphatidylglycerol (PG) 1.51 0.48 2.91
Phosphatidylethanolamine (PE) 25.1 27.1 22.5
Phosphatidylinositol (PI) 9.56 19.2 14.6
Lyso-phosphatidylethanolamine (LPE) 1.20 2.50 Traces
Phosphatidylserine (PS) 12.3 7.20 8.74
Phosphatidylcholine (PC) 46.1 40.3 48.7
Lyso-phosphatidylcholine (LPC) 4.23 3.22 2.55
Levels of Phytosterols and Tocopherols (g/kg) in Seed Oils.
Compound
Black cumin seed oil Coriander seed oil Niger seed oil
Campesterol 0.226 0.735 0.713
Stigmasterol 0.314 1.512 0.667
Lanosterol 0.106 0.152 0.113
-Sitosterol 1.182 1.553 2.035
∆5-Avenasterol 1.025 1.466 0.530
∆7-Avenasterol 0.809 0.365 0.164
Total Sterols 3.662 5.973 4.222
α -Tocopherol 0.284 0.086 0.861
α -Tocopherol 0.040 0.672 0.331
α -Tocopherol 0.225 0.162 0.162
α -Tocopherol 0.048 0.347 0.185
Total Tocopherols 0.597 1.267 1.947
Radical Scavenging Activity of Crude Seed Oils
0
10
20
30
40
50
60
70
80
90
100
0 1 30 60
Time (min)
% R
em
ain
ing
DP
PH
Black cumin TL
Coriander TL
Niger TL
0
10
20
30
40
50
60
70
80
90
100
0 1 30 60
Time (min)%
Re
ma
inin
g G
alv
ino
xy
l
Black cumin TL
Coriander TL
Niger TL
B
Scavenging effect at different incubation times of crude seed oils on (A) DPPH
radical as measured by changes in absorbance values at 515 nm and on (B)
galvinoxyl radical as recorded by ESR.
A B
PUFA Polar lipids Total
Unsaponifiables
Color intensity
(420 nm)
Total
Tocopherols
Total
Phenolics
+ + + + - -
Comparison Between Antioxidant potential of Crude
Seed Oils under Study and Crude Vegetable Oils
Available in the Market.
0
5
10
15
20
25
30
Exhausted DPPH
%
(After 60 min).
Cor
iander
see
d oil
Bla
ck c
umin
see
d oil
Cot
tonse
ed o
il
Peanut o
il
Sunflo
wer
oil
Wal
nut oil
Hem
pseed
oil
Linse
ed o
il
Oliv
e oi
l (ex
tra
virg
in)
Nig
er see
d oil
Oxidative Stability of Crude and Stripped Seed Oils
0
20
40
60
80
100
120
0 3 6 9 12 15 18 21
Storage period at 60 °C (day)
me
q/k
g o
il
Black cumin seed oil
Coriander seed oil
Niger seed oil
0
20
40
60
80
100
120
0 3 6 9 12 15 18 21
Storage period at 60 °C (day)
me
q/k
g o
il
Black cumin seed oil
Coriander seed oil
Niger seed oil
Changes in peroxide levels of crude (A) and stripped (B) seed oils during oven test.
Crude Seed oils Triacylglycerols
Conclusions
1- Information on the bioactive compounds in black cumin, coriander and niger seed oils was
limited. Yet these phytochemicals may bring nutraceutical and functional benefits to food systems.
Therefore, the results will be of importance in processing and utilizing these seed oils and their
by-products as a new source of vegetable oils.
2- High levels of oils recovered from the studied oilseeds and their superior level of triacylglycerols
(ca. 90% of total lipid) make them a suitable source of vegetable oils and encourage their
commercial production.
3- Black cumin and coriander seed oils could be produced as a crude seed oil, but niger seed
should be refined before marketing.
4- Seed oils under study, are a rich source of essential fatty acids and fat-soluble bioactives. Thus,
utilization of these seed oils and their polar lipids is expected to be realized
A- As Additives to poor sources of FSB oils, mixed dishes and dessert.
B- As a source of lecithin (especially, coriander and black cumin seed oils).
C- As a row material for cosmetic (high levels of antioxidants).
Further Research 1- The link, if there any, between the antioxidnat properties of seed oils and their biological effects
under physiological conditions.
2- Oilseeds residues as a source of protein, fiber and water-soluble bioactives.
3- Structure-antioxidant action relationship of phytoglycolipids !?
4- The effect of processing (e.g. refining, microwave or roasting..etc) on the structure and
antioxidant properties of seed oils.
Danke
Dr. Jörg-Thomas Mörsel
Prof. Dr. Lothar W. Kroh
Frau K. Seifert
Frau K. Wilcopolski
Herr W. Seidl
Frau W. Jalyschko
Alle Mitarbeitern und Kollegen (Doktoraten und Diplomanten).
Organizations Technische Universität Berlin (Institut für Lebensmittelchemie).
Zagazig University (Agricultural Biochemistry Dept.)
Zagazig: City and University
Zagazig
. One of the oldest cities in Egypt
(about 4000 years old).
. The old name was POBASTA
which was the capital of Egypt.
. Population: 1 Million.
. Zagazig University was established
1974.
. Faculty of Agriculture was also
established 1974 and it contain 16
departments including Food Science and
Agricultural Biochemistry.