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WORL
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AND PH
ARPharmaceutical
MACEUTICSciences
AL SCIENCES
Taufeeque
etD
al.JOURNAL OF
World
Journal
ofYPharmacy
and
SJIF Impact Factor 5.210
Volume 4, Issue 05, 1808-1814.
Research Article
ISSN 2278 – 4357
OCCURRENCE AND CHARACTERIZATION OF GAMMALINOLENIC ACID IN SEED OIL OF ASTERACANTHA LONGIFOLIA
(L.) NEES
Mohammed Taufeeque*, Abdul Malik and M.R.K. Sherwani
Natural product Lab., Department of Chemistry, J.N.V. University, Jodhpur-342001, India.
ABSTRACT
Article Received on
15 March 2015,
Revised on 06 April 2015,
Accepted on 27 April 2015
The seed oil of Asteracantha longifolia (L.) Nees, family Acanthaceae
has been investigated for fatty acid composition as methyl ester, using
chromatographic and spectroscopic techniques. The seed oil was found
to contain 3.27% of gamma-linolenic acid (GLA), an essential fatty
*Correspondence for
acid (EFA) and 38.52% of oleic acid as a major component of fatty
Author
acids. The percentage GLA of total seed was found 0.91%.
Mohammed Taufeeque
Natural product Lab.,
Department of Chemistry,
KEYWORDS: Gamma-linolenic acid (GLA), Essential fatty acid
(EFA), Asteracantha longifolia, Acanthaceae.
J.N.V. University,
Jodhpur-342001, India
1. INTRODUCTION
Gamma-linolenic acid (GLA; Octadec-cis-6,9,12-trienoic acid) is an
Omega-6-fatty acid, is naturally present in human milk and in wide variety of common foods,
chiefly in meat.[1,2] The main sources of GLA are commercialized plant seed oils, namely
evening primrose (Oenothera biennis),[3] borage (Borago officinalis)[4] and black currant
(Ribes nigrum).[5] GLA is present in the seed oil of Boraginaceae species and its content to
total oil has been used as taxonomical significance.[6] GLA is an essential fatty acid (EFA)
and can cure the EFA deficiency symptoms.[7,8] The GLA appears in some seed oil besides
very common α-linolenic acid (ALA, 18:3ω3). GLA is an important intermediate in the
conversion of linoleic acid to prostaglandins, thromboxanes and other polyunsaturated fatty
acids (PUFAs).[9] Prostaglandins and thromboxanes are known as hormone regulators, affect
many cellular functions and also regulate some blood platelet activities.[10-14] GLA as dietary
supplement show beneficial effect on various pathological and physiological conditions like
inflammatory diseases, cancer, diabetes etc. and also beneficial as a cosmetic
component.[4,9,15-21]
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It is a desirable option to find new species, containing GLA in notable amount because of its
economical value as medicinal oil and as a pure compound for research, nutritional and
medicinal applications. No detailed study on fatty acid composition of the seed oil of
Asteracantha longifolia (L.) Nees syn. Hygrophila auriculata has been reported so far. This
paper mainly focuses on fatty acid composition of seed oil of A. longifolia containing γlinolenic acid.
2. EXPERIMENTAL SECTION
2.1 Materials
Seeds were collected at maturity from arid and semi arid region of western Rajasthan
(India).The whole seed was used for the analyses, they were freeze-dried and ground to
powder using mortar and analyzed immediately.
2.2 Oil Extraction And Trans-Esterification
Oil extraction was performed from grounded seeds of A. longifolia with light petroleum ether
(40-60oC) using soxhlet extraction technique. The solvent was removed completely under
vacuum using rotary evaporator. The analytical values of seed and seed oil were determined
according to the standard American Oil Chemist Society (AOCS) methods.[22] Methyl esters
of oil were prepared using trans-esterification technique.[23] Direct analytical TLC test[24] 2,4DNP TLC test.[25] Halphen test,[26] picric-acid TLC test[27] and alkaline picrate test[28] were
also performed for indication of any unusual fatty acid.
2.3 Analyses of Fame
IR spectrum of FAME was recorded by using Perkin Elmer RX-I FTIR on KBr cell. The UVVis. spectrum was performed on Perkin Elmer Lambda 15 UV/Vis spectrophotometer. Mixed
fatty acid methyl esters (FAME) were analyzed in Perkin Elmer Autosystem XL gas
chromatograph equipped with flame ionization detector. A capillary column of fused silica of
high polarity ( SP 2330; length: 30 m; internal diameter: 0.25 mm; thickness of film: 0.2 µm )
was used. Nitrogen was the carrier gas at a flow rate of 0.75 l/min. The injector temperature
and detector temperature was 260 oC. The oven starting temperature was 80 oC and increased
to 200 oC at a rate of 6 oC/min, held for 5 min. then increased to 250 oC at a rate of 10
o
C/min. Peaks were identified using methyl ester standards (Rapeseed oil mix and PUFAS
from Sigma).
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Position of double bonds was verified by a Thermo scientific TSQ 8000 Gas Chromatographmass spectrophotometer. A capillary column of polysilphenylene-siloxane ( BPX 70 TM;
length: 25 m; internal diameter: 0.22 mm; thickness of film: 0.25 µm ) was used. Helium
was the carrier gas at a flow rate of 1 ml/min. The injector temperature was 250 oC and
detector temperature was 260 oC. The oven starting temperature was 80 oC and increased to
200 oC at rate of 8 oC/min, held for 10 min. then increased to 250 oC at rate of 10 oC/min,
held for 10 min.
3. RESULT AND DISCUSSION
Seed oil of A. longifolia is light yellow in colour and free from any sediments. It is liquid at
room temperature (at 27±2oC). The analytical values of seed and seed oil are given in Table I.
Seed of A. longifolia contain 27.97% of oil, 26.93% of protein and 3.38% of moisture content
to the total seed weight.
Table I: Analytical values of A. longifolia seed and seed oil
Oil content
27.97%
Protein content
26.93%
Moisture
3.38%
Unsaponifible matter
0.79%
Iodine value
107.13
Saponification value
210.46
Refractive index
1.4751
Direct TLC test
-ve
2,4-DNP TLC test
-ve
Halphen test
-ve
Picric acid TLC test
-ve
Picrate test
-ve
Seed oil has 0.79% of unsaponifible matter to the total oil. Iodine value and saponifible value
of seed oil are 107.13 and 210.46 respectively. The seed oil and its FAME showed negative
response to Direct TLC test, 2,4-DNP TLC test, Halphen Test, Picric acid TLC test and
Alkaline picrate test, indicate absence of any unusual fatty acid in the seed oil.
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Table II: Fatty acid composition of A. longifolia seed oil
Fatty acids
Percentage
Myristic
3.67
Palmitic
18.76
Stearic
8.83
Oleic
38.52
Linoleic
16.31
α-linolenic
6.57
γ-linolenic
3.27
Arachidic
1.49
Behenic
0.73
Others
1.82
% GLA of total seed
0.91%
Fatty acid composition of seed oil of A. longifolia is given in Table II. Oleic acid (38.52%)
found to be major fatty acid. Seed oil also has sufficient amount of linoleic acid (16.31%)
with 6.57% of α-linolenic acid (ALA) and 3.27% of γ-linolenic acid (GLA). GLA is found to
be 0.91% of total seed. The composition of fatty acid obtained from GLC and GC-MS were
in good agreement and confirm the position of double bonds. The IR spectra of FAME
exhibited peak at 1738 cm-1 for carbonyl ester besides the usual peaks for hydrocarbon end,
confirmed the absence of any other functional group. The IR and UV-Vis spectra of FAME
exhibited no absorption band for the presence of any trans unsaturation and conjugation.
Besides this, methanolic extract of A. longifolia seed show hepatoprotective activity.[29] In
young and healthy individual, the Δ6- desaturase enzyme effectively catalyzes the conversion
of linoleic acid to GLA.[9] It has been observed that in certain conditions like diabetes, aging,
stress and alcohol consumption, the activity of Δ6- desaturase enzyme inhibit or reduce.[9,30]
It has been established in medical research that GLA as dietary supplement can be effective
in treatment of these conditions.[31]
4. CONCLUSION
On accounting this and fair amount of oil %, protein% in seed and good amount of linoleic
acid with presence of gamma linolenic acid (GLA), it could be a new source of GLA and
vegetable oil. However, before considering A. longifolia as a potential source for human
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consumption, the absence of toxic compounds and other parameters should be checked, this
requires further investigation.
ACKNOWLEDGEMENT
We are indebted to Head, Department of Chemistry, J.N.V. University for providing
necessary facilities and Prof. Pavan Kasera for plant identification and UGC for providing
financial assistance to Abdul Malik.
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