Investigation on Lipid Composition of Exotic Oilseeds

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.