This document summarizes the results of a study investigating the lipid composition and bioactive compounds of black cumin, coriander, and niger seed oils. High levels of oils were recovered from the seeds, making them suitable for vegetable oil production. The seed oils contained high amounts of essential fatty acids and antioxidants like tocopherols. Black cumin and coriander seed oils in particular could be produced and marketed as crude oils. The polar lipid fractions of the seeds oils showed antioxidant effects and could potentially be used as natural additives, lecithins, or in cosmetics. Further research is needed to understand how the seed oil compositions relate to biological effects and how processing may impact their structures and antioxidative

1. Untersuchung zur Zusammensetzung der
Lipide exotischer Ölsaaten
Investigation on Lipid Composition of
Exotic Oilseeds
Mohamed Fawzy Ramadan Hassanien
19.02.2004

2. Vegetable Oils : Production and Consumption .
1- The production of oil plants takes World production of fats and oils
the third place in world production
after starch plants and fruits. Animal
25%
2- More than 90% of the oil plants
are produced in the tropical and
subtropical areas.
Vegetable
75%
4- The major oil crops of
international importance: i.e., World consumption of fats and oils
soybean (Glycine max), oil palm
(Elaeis guineenis), rapeseed (Brassica Animal feed
spp.), sunflower (Helianthus 7% Chemical
industry
annuus), cottonseed (Gossypium 13%
spp.), and groundnut (Arachis
hypogaeo), together accounting for Edible uses
about 84% of world vegetable oil 80%
production.

3. Information on Black Cumin, Coriander and Niger Oilseeds
Black cumin Coriander Niger
(Nigella sativa L.) (Coriandrum sativum L.) (Guizotia abyssinica Cass).
Family Ranonculaceae Family Umbelliferea Family Compositae
Country of Mediterranean countries Mediterranean countries, Eastern -Ethiopia: (50-60% of total
source: and India. Europe, and India. 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 1- Edible uses: Sweet dish, 1- Edible uses: Ingredient of curry 1- Edible uses.
and/or seed oils: pastry, flavoring of food, powder, Flavoring agent of certain 2- Manufacture of soap and
stomachic, carmanitive, and alcoholic beverages. paints.
diuretic agent. 2-Industrial uses: Coriander produce 3- Lubricant of illuminant.
2- Medicinal uses: a high petroselinic acid of potential 4- Defatted Protein-rich meal
Antibacterial, Antifungal, uses (fine chemicals, softeners, used as feed or fuel.
Antineoplastic, soaps, emulsifiers and nylon).
Antihelmenthic.
Total lipids 40% 30% 30-40%
(fresh weight):

4. Goals of The Study
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.
1. To analyze the crude seed oils, their fractions and
their bioactive compounds. Adaptation of fast methods
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,
Health Impact
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
Information for the Market
delaying the oxidation of crude oils.

5. Experimental
Oilseeds
Procedures
Black cumin Coriander Niger
From Turkey From Hungary From India
Grounding
(Particle size = 1-2 mm)
Fatty acid methyl esters
Radical Scavenging Activity GLC/FID
ESR (galvinoxyl)
Photometric (DPPH radical). Extraction of crude seed oils Fat-soluble vitamins
using n-hexane or NP-HPLC/UV
Chloroform:Methanol (2:1, v/v)
Oxidative Stability Saponification
Oven Test (21 days)
Peroxide Value, p-anisidine Value Column Chromatography
UV (230 and 270 nm) Phytosterols
(Silica gel 60)
GLC/FID
Chloroform Acetone Methanol
Glycolipids Phospholipids
Neutral lipids HPLC/UV, TLC HPLC/UV, TLC
TLC and GLC
and GLC and GLC

6. Levels of Fatty Acids in Crude Seed Oils
70 Black cumin seed oil
60
Coriander seed oil
50
Relative Niger seed oil
content 40
(%)
30
20
10
0
C16:0
C18:0
C18:1n-12
C18:1n-9
C18:2n-6
C18:3n-6
C20:2n-6
C22:0
C22:1n-9
C20:5n-3
C22:6n-3
Fatty acid

7. NP-HPLC/UV Analysis of Glycolipid Subclasses.
http://www.cyberlipid.org/glyt/glyt0008.htm
C H 2O H C H 2O H
O
O
HO
O CH2
HO
OH
CH-O-COR O
HO CH-O-COR HO
O O
OH
HO O -C O R 1
OH O -C O R 2
Monogalactosyldiacylglycerol (MGDG)
OH
R2
Digalactosyldiacylglycerol (DGDG)
HO
C H2 OH
R1 O
O
O R1
O
O
N H -C O R 2
HO H O
HO
HO
HO
HO Compound Black Coriander Niger
Cerebroside
R1= H, Steryl glucoside (SG)
(CER) cumin seed
R1= Acyl, Acylated steryl glucoside (ASG)
C H 2S O 3H Acylated steryl glucoside (ASG) 9.95 25.1 38.5
O
Monoglucosyldiacylglycerol 7.88 nd nd
(MGD)
OH
HO O
Steryl glucoside (SG) 9.45 34.9 29.5
O -C O R 1
HO
Cerebroside (CER) 11.9 38.4 31.0
O -C O R 2
Diglucosyldiacylglycerol (DGD) 55.6 nd nd
Sulfoquinovosyldiacylglycerol (SQD)
Sulfoquinovosyldiacylglycerol 5.08 nd nd
(SQD)

8. 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 Coriander Niger seed
cumin
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

9. 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

10. Radical Scavenging Activity of Crude Seed Oils
100 A 100 B
90 90
80 80
% Remaining Galvinoxyl
70 70
% Remaining DPPH
60 60
50 50
40 40
Black cumin TL
Black cumin TL
30 30
Coriander TL Coriander TL
20 20
10 Niger TL 10 Niger TL
0
0 1 30 60
0
0
B 1 30 60
Time (min) Time (min)
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.
PUFA Polar lipids Total Color intensity Total Total
Unsaponifiables (420 nm) Tocopherols Phenolics
+ + + + - -

11. Comparison Between Antioxidant potential of Crude
Seed Oils under Study and Crude Vegetable Oils
Available in the Market.
30
25
20
Exhausted DPPH
% 15
(After 60 min).
10
5
0
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12. Oxidative Stability of Crude and Stripped Seed Oils
Crude Seed oils Triacylglycerols
120 120
Black cumin seed oil
Black cumin seed oil
Coriander seed oil
100
Coriander seed oil 100
Niger seed oil
Niger seed oil
80 80
meq/kg oil
meq/kg oil
60 60
40 40
20 20
0 0
0 3 6 9 12 15 18 21 0 3 6 9 12 15 18 21
Storage period at 60 °C (day) Storage period at 60 °C (day)
Changes in peroxide levels of crude (A) and stripped (B) seed oils during oven test.

13. 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.

14. 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.)

15. Zagazig: City and University
. One of the oldest cities in Egypt
Zagazig
(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.