Phytochemical analysis of sida ovata seed oil a new source of cyclopropenoid fatty acid ijsit 2.4.3

Seema Parveenet al., IJSIT, 2013, 2(4),277-283
IJSIT (www.ijsit.com), Volume 2, Issue 4, July-August 2013
277
PHYTOCHEMICAL ANALYSIS OF SIDA OVATA SEED OIL: A NEW SOURCE
OF CYCLOPROPENOID FATTY ACID
Seema Parveen*, Swatika Sharma, Abdul Malik and M.R.K. Sherwani
Department of Chemistry, Jai Narain Vvas University, Jodhpur 342001, Rajasthan, India
ABSTRACT
The seeds of Sidaovata were collected from the arid zone of Rajasthan and analysed for the
characterization of the fatty acids. This paper accounted the presence of Cyclopropenoid fatty acids(Malvalic
and Sterculic). The occurrence of CPFA was confirmed by HBr-titration, Halphen test, TLC, NMR and IR
spectroscopic methods.
Keywords: Sidaovata (Malvaceae), seed oil characterization, Cyclopropenoid fatty acids.
Structure of Malvalic and Sterculic acids (Cyclopropenoid fatty acids)

278
INTRODUCTION
The plant of Sidaovata (Malvaceae) is widely spread in the arid parts of tropical land in India. The
roots of Sida species are considered excellent adaptogenic and immunomodulator, general nutritive tonic and
prolonged life, useful in tuberculosis, heart diseases, cough and respiratory diseases1. The plant species
belonging to Malvaceae and Sterculeaceae are growing abundantly throughout the Arid zone of Rajasthan and
all over India, the fruit of some species Are demulcents, mildly astringent and commonly used in gripping and
flalulence2.
The seed oil of Sidaovata responded positive Halphen test3 and was selected for the estimation and
characterization of CPFA. The naturally occurring CPFA are sterculic (n=7) and malvalic (n=6), found mainly
in the seed lipids of four plant families of order malvales which includes (Sterculiaceae, Malvaceae,
Bombaceae and Tiliaceae). CPFA occur in plant lipids mainly as glycerides. CPFA have been the subject of
many investigations due to their Carcinogenic, Co-Carcinogenic activities4-8. The presence of CPFA in food is
dangerous not only for human healthbut also for animals9-14. Quantitative estimation of total cyclopropenoid
fatty acids content can be achieved most conveniently by HBr titrationto a level of .01%15.
EXPERIMENTAL
The soxhlet-extraction method was adopted to extract oil from ground seeds, using petroleum ether
(40-60oC). The moisture contents, Iodine value, Saponification value of the oil were estimated by standard
AOCSmethods16. The protein content of the oil was estimated by Kjeldahl method. Thin layer
chromatographic techniques were used to resolve different fatty acids components of the oil along with
silver ion TLC17.
The spots were made visible on analytical plates by charring with 20% aquous solution of perchloric
acid. The transesterification of the oil was carried out using sodium methoxide. Preparative TLC were used
for the separation of large quantity of cyclopropenoid fraction. AmilNucon gas chromatograph model no.
5700 equipped with a flame ionization detector was used for the GLC study of oil samples. The U.V spectra of
the oil and methyl esters have been conducted with a Shimadzu UV-1601 spectrophotometer. The NMR
spectra were recorded on Bruckerx300 spectrophotometer and oil samples were prepared in CDCl3
containing tetrametylsilane as an internal standard. The IR spectra of oil were obtained from Jasco-made FT-
IR spectrophotometer.

279
RESULTS AND DISCUSSION
The seed oil Sidaovata was evaluated for its physiochemical properties (Tabie-I). The quantitation of
total CPFA material was carried out by H-Br titration which revealed the presence of 16% by weight of
CPFA15. Thin layer liquid chromatography revealed two spots. The methyl ester obtained from the oil sample
exhibited the IR band at 1010cm-1 and 1852cm-1, supporting the presence of cyclopropene ring. The
characterization of unusual acids was achieved by separation using preparative TLC.
Characterization of fraction-I:
The combined GLC-TLC techniques were used for the analyses of component acids in the CPFA
fraction. This fraction have RF value 0.75 on TLC. The quantitative results of direct, reversed phase and silver
ion TLC of this fraction were compared with the esters of Sterculiafoetida used as a reference standard. The
spots corresponding to saturated, monoene, diene and triene in this fraction of oil were resolved by AgNO3-
TLC[17] parallel to those obtained from Linseed esters. The negative Halphen test indicated the absence of
CPFA in this fraction. The IR spectrum did not show any peak corresponding to CPFA, however a band at
1710cm-1 observed corresponding to ester-carbonyl group.
Characterization of fraction-II:
This fraction showed RF 0.55.The occurrence of CPFA in this fraction was confirmed by the positive
Halphentest[3]. The resulting methyl esters obtained from the base catalyzed transesterification showed IR
band at 1010cm-1 and 1852cm-1. The quantitative estimation of CPFA by HBr-titration showed the presence of
16% by wt. of CPFA. The absence of conjugation or trans-unsaturation in this fraction of oil was confirmed by
U.V spectrum. The NMR spectra of this fraction showed typical cyclopropenoid group signal at δ 0.71(singlet)
other proton signals were also observed at δ 3.6(3H,-COCH3), δ 2.2 (2H, α to carbonyl), δ 1.2 (chain-CH2-)
and δ 0.88 (3H, term—CH3). The GLC analysis of the AgNO3-methanol treated methyl esters confirmed the
presence of Malvalic and Sterculic acids by comparison of relative retention time of similar derivatives from
Sterculiafoetida esters. The GLC data given in table-II of the CPFA were found in close agreement with those
obtained by H-Br titration [15] methods. The Fatty acids composition of the seed oil is shown in Table-II. The
Malvalic and Sterculic acids were found at levels of 14.20% and 6.30% respectively as silver nitrate adduct
and the products obtained have been depicted in the scheme. The presence of CPFA has been reported for the
first time in the seed oil of Sidaovata.

280
SCHEME
CH3 (CH2)7 C C (CH2)n C OCH3
O
CH2
AgNO3 Methanol
n=6 (Malvalic acid)
n=7 (Sterculic acid)
CH3 (CH2)7 C C (CH2)6 C OCH3
OCH2OCH3
H- CH3 (CH2)7 C C (CH2)6 C OCH3
OCH2OCH3
H-
OCH2OCH3
H- CH3 (CH2)7 C C (CH2)7 C OCH3
OCH2OCH3
H-
O
CH2
O
O
CH2
O
O
CH2
O
O
CH2
O
Ethers and Keto derivatives of malvalic and sterculic acids
Seed Analysis Oil Properties
Nameand Family Oil % Protein%
N X6.25
Moisture% I.V
Wij’s
S.V Refractive
Index
HBr
equivalent
Sidaovate
(Malvaceae)
2.85 17.12 2.3 122 185 1.4890 16.0
Table 1:Analytical Data of Seed and Oil
I.V=Iodine value, S.V=Saponification value, HBr = Hydrogen Bromide Equivalent

281
Name and
Family
16:0 18:0 18:1 18:2 18:3 20:0 Others
Sida ovate
(Malvaceae)
35.2 12.3 15.9 29.6 6.9 _ Traces
Table 2: Fatty Acid Composition Determined by GLC of Fraction-I
Fatty Acids Sterculiafoetida Fraction-II
Myristic ----- 2.4
Palmitic 24.8 18.0
Palmitoleic 1.0 ------
Stearic 3.4 2.4
Oleic 9.4 14.6
Linoleic 1.8 38.5
Linolenic 1.2 3.5
Malvalic 7.1 14.2
Sterculic 51.2 6.3
Table 3: GLC Analysis of AgNO3 –Methanol treated Methyl Esters:
Fraction-II (uncorrected wt. %)
Structure of Malvalic and Sterculic acids

282
Sidaovata plant Sidaovata seeds
REFERENCES
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4. Hendrick, J.D; Sinnhuber, R.O; Loveland, P.M; Pawlowski, N.E; Nixon, J.E. Hepatocarcinogenicity of
glandless cotton seede and cotton seedoil to rainbow trout (Salmogairdnerii). Science 1980; 208:309-
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5. Sinnhuber, R.O; Lee, D.J; Wales, J.H; Landens, M.K; Keyl, A.C. Hepatic carcinogenesis of alfatoxin M, in
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Phytochemical analysis of sida ovata seed oil a new source of cyclopropenoid fatty acid ijsit 2.4.3