• TUCHIVES
FISHERIES AND MARINE SERVICE
'Iranslation Series No 3984
Composition of the sterol fraction of lipids extracted from oil seeds
by E. Tiscornia and G. C. Bertini
Original title: Composizione della frazione steroliCa nei lipidi estratti da semi oleosi
From: Riv. Ital. Sostanze Grasse 50(Aug.): 251-268, 1973
Translated by the Translation Bureau (MG) • Mültilingual Services Division Department of the Secretary of State of Canada
Department of the Environment 41sheries and Marine Service Halifax Laboratory . Halifax, N.S.
1977
30 pages typescript Fd- M .tr- 3 `3 ^ `i
DEPARTMENT OF THE SECRETARY OF STATE SECRÉTARIAT D'ÉTAT TRANSLATION BUREAU BUREAU DES ♦,'i^ ï= • TRADUCTIONS ^^•t.' _ MULTILINGUAL SERVICES DIVISION DES SERVICES CANADA DIVISION MULTILINGUES
TRANSLATED FROM - TRADUCTION DE INTO - EN Italian English AUTHOR - AUTEUR E. Tiscornia, G.C. Bertini
TITLE IN ENGLISH - TITRE ANGLAIS
Composition of the sterol fraction of lipids extracted from oil seeds
TITLE IN FOREIGN LANGUAGE (TRANSLITERATE FOREIGN CHARACTERS) TITRE EN LANGUE ETRANGÉRE (TRANSCRIRE EN CARACTÉRES ROMAINS)
Composizione della frazione sterolica nei lipidi estratti da semi oleosi
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The Italian Review of Fatty Substances
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Fr cdy ?I ce61,51.F. T RA Us CT 0 0 siTION OF THE STEROL FRACTION OF LIPIDS EXTRACTED FROM OIL SEEDS informeion sainement E. Tiscornia, G.C. Bertini
Summary - Within the framework of research undertaken with a view to better characterizing the various kinds of natural vegetable oils and fats for ' human consumption, the Authors in this paper have considered the composition of the sterol fraction of oil seeds commonly used in the Italian oil industry. Based on the results obtained using "coordinated analytical techniques" (TLC and GLC), the Authors found that the qualitative sterol composition of the oils under consideration is generally independent of the variety and region of production. For some seeds, however, these factors seem to have some influence on the quantitaave composition which for some types remains within narrow limits of variability, whereas for others,.the variability shows broader fluctuations.
A systematic study of the non-glyceride constituents of vegetable
oils was'begun more than ten years ago by Jacini and his group (1-8). The
of these and other Authors provided a meaningful picture of the compo- work
sition of vegetable oils and demonstrated that this composition is closely
related to the species of plant from which the oil is extracted (9-31).
Among the various constituents which,.in the present state of our
knowledge, are believed to make up the unsaponifiable fraction of a vege-
table oil, the sterol fraction is the one that has been most extensively
investigated by researchers.
SEC 5-25T (6/76) 2
Recent studies appearing in the literature (27-39) have helped
'decisively in the selection and improvement of analytical methods in their
various phases, also providing interesting results on the sterol composi-
tion of several edible oils.
On the present state of researCh,all Authors essentially agree on
the analytical method which consists in separating the various unsaponifiable
fractions by TLC preparation on plates Of silica gel or alumina; however,
two different tendencies exist as regards the GLC analysis of sterols.
According to Wolff et al. (38, 40-43) GLC analysis can be carried
out directly on free sterols, using stainless steel columns kept at a high
' temperature for •a few days and inactivating the reaction centres of the
stationary phase with repeated injections of standard mixtures.
However, according to other Authors (35-37, 39, 44-53) it is pre-
ferable to convert free sterol into derivations better suited for GLC,
such as, for example, trimethylsilyl ethers (TMS). They also suggest the
use of special experimental conditions of gas chromatography, such as the
use of instruments permitting on-column injection, or quartz injectors and
glass columns filled with an acid-washed and silanized support.
In this manner, onè obtains optimum conditions for the qualitative
and especially for the quantitative determination of the individual sterols,
preventing the possibility of breakdown of the sterol molecule, dehydration
of the steràls on the column and phenomena of irrèversible adsorption on
the active points of the column.
It may be noted that the results reported in the literature generally
show very significant differences in the composition of the sterol fraction
of edible vegetable oils obtained from different species of seeds or fruits,
but much less is known about the relationship existing between sterol fraction 3
and variety and/or- place of production of a same species. These factors are known to noticeably affect the fatty acid composition of an oil, and
sometimes to cause marked variations.
Therefore, we can say that up to now, the possible effect of the
abovementioned factors on the composition of the sterol fraction, mainly with respect to different production zones (20, 24, 29, 36-739, 42, 43, 54, 55), has only been taken into account for the various types of oil derived from
"Olea europea", but similar experiments have not been carried out on oils obtained from other fruits or seeds (11, 17-19, 28, 29, 33, 36, 56, 57).
In fact, only few papers have been published on this subject, a paper by Capella and Losi (32) on the analysis of the sterol fraction obtained from two varieties of "Brassica Napus" seeds (Matador and Regina II), and a paper by Tiscornia and Monacelli (35) on the composition of the sterol fraction of the oil obtained from two different va-rieties of fruit, commonly called seeds, of "Carthamus Tinctorius". The two varieties-were found to contain different levels of linoleic acid.
On the basis of the foregoing, we thought that an experimental work investigating the composition of the sterol fraction of lipids extracted from oil-seeds commonly used by the Italian oil industry would be of interest.
For each species of seeds used, the production zone was studied and for some samples the different varieties were also taken into account.
EXPERIMENTAL METHODS
The experiments were conducted on 38 samples of oil extracted from seeds or fruits, belonging to 11 different plant species, of foreign origin with the exception of the seeds of "Vitis vinifera" produced in Italy. 4
32 of these samples were obtained from homogenous, controlled lots of seeds from a single species, free of extraneous seeds, by an
industrial extraction method involving pressure and subsequent solvent
extraction; two samples, namely one obtained from fruits of "Carthamus
Tinctorius", of Spanish origin, and one obtained from seeds of "Brassica
Napus", of Canadian origin, were extracted in our laboratory by means of
a Soxhlet apparatus with petroleum ether (40-60 °C) following grinding and
drying at low temperature. The exact procedure used to extract the
remaining four samples, namely three samples of "Carthamus" oil of American
origin and one of "Thea" oil of Chinese origin was unknown since the samples
were already in the oil state. However, we can say with absolute certainty
that these samples were genuine.
For all oil samples, the composition of the unsaponifiable sterol
fraction was determined using the method of analysis described in N.G.C.
Ba III 13 (1971) (58). Essentially the method consists of the following steps:
a) preparation of the unsaponifiable fraction;
h) separation of the sterol fraction on TLC;
c) preparation of the sterol trimethylsilyl derivatives (TMS);
d) GLC analysis of TMS.
We should point out here that the gas chromatographic determination
of each sample were done on two different apparatus simultaneously under
the following experimental conditions;
1) Apparatus: Perkin Elmer gas chromatograph, mod. 990, equipped with flame
ionization detector and glass injection port;
Glass chromatographic column 3 m long with an interior diameter of 1.5 mm;
Liquid phase: methylsilicone polymer SE 30 2.5%; . 5
Support: Chromosorb W 100-120 mesh washed .with acids and silanized; o Temperature of the column: 245 C; o Temperature of the evaporator: 280 C;
Carrier gas: nitrogen with a flow rate of 25-30 ml/min;
Velocity of the paper: 1.25 mm/min. -
2) Apparatus: Fractovap Carlo Erba mod. G 1, equipped with flame ionization
detector and on-column injection; •
Glass chromatographic column 2.80 m long with an inner diam. of 2 mm;
Liquid phase: methylsilicone polymer SE 30 2%;
Support: Chromosorb W 100-120 mesh washed with acids and silanized;
Temperature of the column: 240°C; o Temperature of the injection block: 280 C;
Carrier gas: Helium with a flow rate of 20-25 ml/min;
Velocity of the paper: 6"/h.
The position of the single peaks corresponding to sterols was identi- fied both by determining their retention times and by the use of internal standards; columns with different liquid phases were used.
In this manner, the single sterols could be identified precisely, and when-it was not possible to identify a given peak with certainty, we called it a "non-identified sterol".
Lastly, we must point out that only those peaks were considered which were perfectly distinguishable in a gas chromatographic graph where the major component was, at most, full scale at the attenuation used.
Fig. 1-27 give the' original gas chromatograms showing the typical composition of the sterol fraction of a few edible vegetable oils. Table I shows the values, expressed as percentages of total sterols, of the sterol 6 4
composition of the samples studied; in the subdivision of the various botanical
families, the systematic order of families given by A. Engler (59) was ,
followed.
RESULTS AND DISCUSSION
Theaceae - The composition of the sterol fraction of the oil obtained from
the species "Thea Sinensis" (Fig. 1; Table I; Sample no. 1), of Chinese 7 origin, was essentially characterized by the presence of two sterols: A -
stigmastonal (64%) and 8-sitosterol (34%).
Moreover, under the experimental conditions used, the presence of
of campesterol (about 2%), of minimal amounts of cholesterol moderate amounts
and brassicasterol and non-measurable traces of stigmasterol was detected.
Cruciferae - The composition of the sterol fraction of lipids extracted
from the species "Brassica Napus" (Fig. 2-5; Table I; Sample 2-7) was
.essentially characterized by the constant presence of three sterols:
8-sitosterol, campesterol and brassicasterol.
Moreover, under the experimental conditions used, it was possible
to detect the presence of small amounts of stigmasterol (max 1.5%) and of
cholesterol (max 0.9%), while in one of the samples (Sample 3) non measurable 7 traces of A -stigmastanol were found.
Qualitatively, the sterol composition of rapeseed oil seemed to be
independent of the variety and place of origin of the seeds from which the oil
was extracted. In fact, the Vd0 varieties studied,coming from different
production zones, the first of which had a high erucic acid content (38-45%)
(Sample 2-6) and the second a zero erucic acid content, (Sample 7) showed no
significant qualitative difference in their sterol composition. 7 ,
Quantitatively, in sample of the samè variety but of different
origin, the percentage of sterols remained within narrow limits of variability
(s-sitosterol: 54.5-58.9%; campesterol: 27.5-31.7%; brassicasterol: 12.0-12.7%;
stigmasterol: traces-1.6%; cholesterol: 0.5-0.9%; A 7-stigmastano].: 0-traces).
It is interesting to note that thesè limits seemed to be particularly
narrow for brassicasterol, a sterol found mainly in sedds of Cruciferae.
More significant differences were found in samples extracted from
different varieties of seeds. In particular, the "genetically varied"
sample from the variety "Canbra" (Sample 7) showed a noticeable decrease in
brassicasterol content; as was mentioned previously, this sterol is charac-
teristic of the Cruciferae family. .
Leguminosae - The composition of the sterol fraction of lipids extracted
from the two species "Arachis Hypogaea" and "Soja ispida" (Fig. 6-9 and
10-13; Table I; Sample no. 8-13 and 14-20) was essentially characterized
by the constant presence of three sterols: ^-sitosterol, campesterol and
stigmasterol.
In additïon, under the experimental conditions used, it was possible
to detect the presence of moderate amounts of A7-stigmastanol and small
amounts of cholesterol; while in some samples non-measurable traces of
.brassicasterol were found.
For each sample of oil the following observations were made:
a) Peanut oil. The qualitative sterol composition of this oil seemed to be
independent of the place of origin of the seeds from which the oil was extracted.
In fact, the six samples (Sample nos.8-13) from five different production zones
which were studied showed no significance qualitative difference in their sterol
composition. 8
Quantitatively, while for five samples from four different places
of production (Sample no. 8-12), the sterol percentages remained within rather narrow limits of variability (e-sitosterol: 72.4-74.8%, campesterol: 7 13.9-15.8%; stigmasterol: 8.9-11.2%; A -stigmastanol: traces-1.3%; brassi-
casterol: 0-traces), in the sample coming from Sudan (Sample no. 13), of
unknown variety, the sterol percentage composition differed considerably
from that reported for oils of the sanie species.
b) Soybean oil. The qualitative sterol composition of this oil seemed to be
independent of the place of origin of the seeds from which the oil was
extracted. In fact, the seven samples (Samples no. 14-20) from three dif-
ferent production zones, which were studied showed no significant qualitative
difference in their sterol composition.
Quantitatively, while in six samples produced in three different
places (sample no. 14-19), the values for individual sterols were within narrow limits of variability (e-sitosterol: 50.3-60.2%; campesterol: 19.7-24.0%; 7 s stigmasterol: 14.5-22.3%; A - tigmastanol: 1.4-5.1%; cholesterol: 0.3-0.5%; brassicasterol: 0-traces); in the sample from Nigeria (Sample no. 20), of unknown variety, the sterol percentage composition differed considerably
from that reported for oils of the same species. In this last sample, the highest percentage variations were in campesterol, the value of which 7 markedly decreased and in A -stigmastanol which greatly increased.
Vitaceae - The composition of the sterol fraction of lipids extracted from
the species "Vitis vinifera" (Fig. 14 and 15;« Table I, Sample no. 21-23) was essentially characterized by the constant presence of three sterols: e-sitosterol, stigmasterol and campesterol. 9
In addition, under the experimental conditions used, it was possible 7 to detect the presence of moderate amounts of A -stigmastano1 (max 3%) and minimal amounts of cholesterol (max 0.4%), while in two samples (Sample no. 22 and 23) non-measurable traces of brassicasterol were found.
In particular, the qualitative sterèl composition of grape seed oil seemed to be independent of the place of origin of the seeds from which the oil was extracted. In fact, the three samples studied (Sample no. 21-23), all produced in Italy but in three different places, showed the same sterol
composition.
Quantitatively, the values found for the individual sterols showdd only very slight variations (-sitosterol: 74.2-75%; stigmasterol: 11.8-12.2%; 7 campesterol: 10.2-10.5%; A -stigmastanol: 2.2-3.0%; brassicasterol: 0-traces).
Pedialiaceae - The composition of the sterol fraction of lipids extracted from the species "Sesamum indicum" (Fig. 16-18; Table I; Sample no. 24-27) was essentially characterized by the constant presence of three sterols:
8-sitosterol, campesterol and stigmasterol.
In addition, under the experimental conditions used, it was possible . 7 to detect the presence of moderate amounts of A -stigmastanol, on the average not higher than 2%, while in one of the samples (Sample no. 27) the percentage of this sterol was 2.5%. Furthermore, minimal amounts of , cholesterol (max 0.3%) were found and in sample no. 27, non-measurable traces of brassicasterol.
In particular, the qualitative sterol composition of sesame oil seemed to be independent of the place of origin of the seeds from which the oil was extraced. In fact, the four sample (Sample no. 24-27) from four different production zones, which were studied showed a similar sterol composition. • 10
Quantitatively, while in three sample from three different zones
of production (Sample no. 24-26), the sterol percentages were within
narrow limits of variability (8-sitosterol: 68.5-71.9%; campesterol: 7 18.8-22.2%; stigmasterol: 7.4-8.6%; à -stigmastanol: 1.9-0.7%; cholesterol:
traces-0.3%), in the sample from High Volta (Sample no. 27), of unknown
variety, the sterol percentage composition differed from that of other.
oils of the same species. In this last sample, the highest percentage
variation was in campesterol, the value of which greatly increased, and
in 0-sitosterol, where it markedly decreased.
Compositae - The composition of the sterol fraction of lipids extracted from
the two species "Carthamus Tinctorius" and "Helianthus annuus" (Fig. 19-21
and 22-25; Table I; Sample no. 29731, and no. 32-36) were essentially
characterized by the constant presence of four sterols: 8-sitostero1, 7 A -stigmastano1, campesterol and stigmasterol.
• In addition, under the experimental conditions adopted, we could
detect the presence of minimal amounts, generally higher than 0.2%, of
cholesterol and of another component present in some samples in quantities
as high as 4-6%. The retention time of this compoenent was between those
of stigmasterol and 8-sitosterol, but in the present state of our knowledge,
a full identification is not yet possible.
In particular, for each type of oil, the following observations
were made:
a) Safflower oil The qualitative sterol composition of this oil seemed to
be independent of both the variety and place of origin of the seeds from
which the oil was extracted. The two varieties studied, one with a high
content of linoleic acid (65-80%) (Sample no. 28-29) and one (UC-1) with 11 •
a low content of linoleic acid (10-13%) (Sample 30-31), coming from dif-
•erent places of production, showed no significant qualitative difference
in their sterol composition.
Quantitatively, in the two samples obtained from the variety with
a high linoleic acid content (Sample 28 and 29), but of different origin,
the percentages of individual sterols showed narrow limits of variability.
The variability was higher in the two samples obtained from the variety
with a low linoleic acid content (Sample 30-31) although they cauefrom
the same production zone.
More significant differences were found in the samples obtained
• from the two different varieties of fruit. In fact, in both the "genetically
varied" samples, variety UC-1, there was a considerable decrease in the 7 level of A -stigmastanol, a sterol mainly found in the family of Campositae.
In this regard, it is Worthwhile noting that the quantitative
variations in the sterol composition were smaller than those found in fatty
acids.
From these results, it could be concluded that genetic variations
induced in "Carthamus Tinctorius" may greatly affect the fatty acid compo-
sition 6f its lipids, but the same phenomenon does not occur in the unsaponi-
fiable (namely the sterol) fraction, the composition of which seemed to be
much less influenced by such genetic variations.
h) Sunflower oil - The qualitative sterol composition of this oil was inde-
pendent of the place of origin of the seed from which the oil was extracted.
In fact, the five samples (Sample 32-36) from four different production zones
which were studied showed no significant qualitative difference in their
sterol composition. • 12
Quantitatively, the sterol percentages were within narrow limits of 7 variability (e-sitosterol: 62.1-65.3%; A -stigmastanol: 13.7-17.0%;
stigmasterol: 10.1-11.6%; campesterol: 9.6-11.0%; cholesterol: traces 0.2%;
non-identified sterol: absent-present in small undetermined amounts).
It is interesting to - note that the greatest variations are in 7 A -stigmastanol which, as already mentioned, is Characteristic of the
Compositae.
The composition of the sterol fraction of lipids extracted from
the species "Zea Mays" (Fig. 26 and 27, Table I, Sample no. 37 and 38) was essentially characterized by the constant presence of three sterols:
e-sitosterol, campesterol and stigmasterol.
Moreover, under the experimental condition used, it was possible 7 to detect the presence of.moderate amounts of A -stigmastanol (max 5.1%)
and minimal amounts of cholesterol (max 0.4%).
In particular; the qualitative sterol composition of corn oil
'seem&I to be independent of the place of production of the seeds from which
the oil was extracted. In fact, the two samples (Sample no. 37-38) from
two different production zones which were studied showed no significant
qualitative difference in their sterol composition.
Quantitatively, the values found for the sterols showed narrow
limits of variability (-sitosterol: 68.2-71.5%; campesterol: 16.8-21.7%; 7 stigmasterol: 6.2-7.3%: A -stigmastano1: 2.8-5.1%; cholesterol: traces-0.4%).
CONCLUSIONS
The examination of the results obtained in this first study aimed at characterizing the sterol composition of the main edible vegetable oils used by the Italian oil industry, also in relation to the variety and zone 13
of origin of the fruit or the seeds from which the oil was extracted, enables us to draw some interesting conclusion:
- It is confirmed that the qualitative composition of the sterol
fraction of an oil is closely dependent on the species and variety of the
fruit or seed from which the oil is extracted.
- The qualitative composition of the sterol fraction of an oil is af-
fected neither by the genetic variations brought about inthe plant, to permit the obtention of oils with a varied fatty acid composition, nor by
the place of origin of the fruit or seed from which it was extracted.
- The quantitative percentage composition of the sterol fraction of
an oil can be affected both by the variety and the place of origin of the
fruit or seed from which the oil was extracted. This effect generally
remains within rather narow limits, so that the values of the individual
sterols vary only slightly. Only in a few cases, -mainly in genetically varied oils, are greater variations to be found. 14
4
f !
Fig. 1 - Gas c`irr,^^3tn^ram of the sterol fraction of the oil from "Thea Sinensis" (Sample no. 1). -
*) Cholesterol; **) Brassicasterol; 1) Campesterol; 2) Stigmasterol; 3) 43-sitosterol; 1+) Q7--stigmastunol (TMS derivatives - Perkin Elmer gas chromato,raph). ▪
TABLE I - Sterol composition in of total sterols of samples of edible vegetable oils.
% Compoeo2s... ce F art/ c'rfeig'- Denee4n•aelsee- della fr..1.77.414.e sterolle fr...a criom eff..p., Farnig-ge G D . Species earlet Provenlenx plante CornmorciaV no, BotanIcaa dle- Brassica- Campe- Stigma- Steroid 5-sito- 4,7-stigma1 delPplio sterol% sterote sterole sterolp non I ent, F c...... : ree 'ie o ‘22,, ivez-c- sterols% strolf( h e à 1 Theaceae Thea sinensis - Cina SOL11.0 Theet Thea seed oil 0,2 0,3 1,7 tr. - 33,7 64,1 2 Cruciferae Brassica napus - Fitance, SEEM Colza Rapeseed oil 0,9 12,7 27,5 tr. - 58,9 - 3 • » - Franca.- 0,5 12,0 28,7 1,5 - 57,3 tr. 4 • • » - Franca, • • 0,5 12,4 28,9 1,6 - 56,6 - 5 • * • - Polq.nd., • • • . 0,6 12,7 31,3 tr. - 55,4 - • 6 • • • - Canada 0,6 12,2 31,7 1,0 - 54,5 - i 7 • » » Canbra* Canada 0,5 9,2 37,3 1,2 - 51,8 - 1 8 I Leguminosae Arachls hypogaea - Nigeria StAle Arachide Peanut o il 0,3 tr. 13,9 11,1 - 73,4 1,3 9 » » - Gambia ^ 0,8 13,9 10,0 - 74,6 0,7 10 • • • - Egitto fpl,i- • 0,3 - 14,3 8,9 - 75,6 0,9 11 • • • - . U.S.A. u • 0,6 tr. 15,8 11,2 - 72,4 - 12 » • • - U.S.A. • 0,4 14,4 9,7 - 74,8 0,7 13 • • • - 'Sudan • 0,9 18.4 13,0 - 66,9 0,8 14 • Soja hispida - Romania &erne- Soja Soybean• oll 0,5 19,7 14,5 - 60,2 5.1 15 • • • • , . - U.S.A. 0,3 21,3 19,3 - 57,7 1,4 16 • » 31 ...... U.S.A. 0,5 tr. 22,1 22,3 - 50,3 4,8 17 • » • - U.S.A. • 0,4 tr. 24,0 19,2 - 52,8 3,6 18 • . ,. ., - Brasile • 0,5 tr. 21,0 18,9 - 56,1 3.5 19 • • • - Brasile • 0,3 23,0 19,4 - 54,1 3,2 20 • • » - Nigeria • 0,5 0,2 13,0 22,1 - 54,0 10,2 21 Vitaceae Vitis vinifera - italja'e ' . (Puglia) S ti n e-fi Vinacclolo Grape seed oil 0,3 tr. 10,3 12,2 '7 74,2 3,0 22 • 24 le •••• italja' (Puglia) 0,2 , ■■■■■ 10,5 11,8 - 75,3 . 2.2 23 • •• » - Italjz( . •
1 • (Calabria) 0,4 tr. 10,2 . 12,2 - 74,3 2,9 V 24 Pedaliaceae 21 Sesamum indicum - Venezuela terne fi Sesamo Sesame oil 0,3 19,6 8,4 - 70,4 1.3 I 25 » • • - Sudan - 71,9 IA tr. 18,8 7,4 1,9 e 26 » » » - Nigeria • tr. 22,2 8,6 - 68,5 0,7 VIS 27 » • • - Alto Volta - 1 0,2 tr. 27,6 11,1 58,7 2,5
1. " 28 Compositae . Carthamus tinctorius Spagna ,.,--1 fruttlit Cartamo Safflower all 0,2 12.7 9,0 5,8 44,2 28,1 1V
I ... 29 • • • U.S.A. 0,2 13,1 10,8 3,6 45,0 27,2 30 • . • » UC4 U.S.A. VNV .... (California) 0,2 ■■■■• 15,2 11,7 3,8 47,6 21.5 M
1 31 • • • UC-1 U.S.A. (California) 0,7 10,6 11,7 presente: . . non deter. 58,4 18,6 SOS 31 32 • Hellanthus annuus - Spagnd LK. frunài,t- Glrasole Sunflower oll 0,2 ■•■■••• 9.6 11,0 presente: VI
N non deter. 62,2 17,0 7. 33 • • » - U.R.S.S. 0,1 10,1 10.8 - 65,5 13,7
>i0 3 34 • • • - U.S.A. tr. 11,0 11,6 - 63,6 13,8 V 35 • • - Argentina 0,2 10,8 11,1 presente: SS 1 non deter. 64,0 13.9 • 36 • • • . - Argentina tr. ■•••• 11,0 10,1 - 62,1 16,8 37 Gramineae Zea maya - Argentina '10A r- (Plata) . frutte 1- Mals Corn oll 0,4 16,8 6,2 - 71,5 5.1 36 • • • - Ital tr. 1■•••• 21,7 7,3 - 68.2 2,8 > o J o *) brucic53 0; o • ••) A. oleicji 18,2 0/0 - linoleic,c1 68,9%; •••) fer6: oleicy2,2% - lInolelcieSn.76.6%; • • • •) olelcp'07, 9,9% ) iinololc ,10,5%.
»0».», . 111111110110•1~May
^TI u-77 . 16 Fig. 2 - ,Gas chromatogram of the sterol. , fraction of rapeseed oil (Sample no. 2) 1.) cholesterol; 2) brassicasterol; 3) campesterol; 4) stigmasterol; 5) '.-sitosterol (TMS derivatives- Carlo Erba gas chromatograph).
3
2
1
3
2
Fig. 3 - Gas chromatogram.of the )iI sterol fraction of rapeseed oil (Sample ne. 5). ! ) 1) cholesterol; 2) brassicadterol; . 1 3) campesterol; stigmasterol; 5) !:;-sitosterol (TMS derivatives Carlo Erba gas chromatograph).
) A RIVISTA ITALIANA DELLE SOSTANZE GRASSE - Vol i . Anns-rn 1071 Fig. 4 - Gas chromatogram of the sterol, fraction of rapeseed 17 oil.(Sample no.6). 1) cholesterol; 2) brassicasterol; campesterol; 4) stigmasterol;' 5) 5-sitosterol (TMS derivatives Carlo Erba gas chromatograph).
'lg. 6
;) cot 1:terolc
pie11; iito :e rre :o de taent }rte
?anti. 1.2 .stra JI fat), 'aent :silo Ir. iFig. 5 - Gas chromatogram of the di uu .ale, sterol. , fraction of rapeseed !iscr. oil (Sample no. 7). ) stie- 4 tri cholesterol; 2) brassicastcrol; re )graiu . 13 campesterol; 4) stir,mastcrol; adiv 5) 5-sitosterol (TMS derivltives- ' Perkin Elmer gas chromatcy:raph). r 18
Fig. 6- Gas chromatogram of the sterol. fraction of peanut oil (Sample nO. 9). 1) cholesterol; 2) campesterol; 3) asterol; 4) ^i-sitosterol; stiEY-stigmastanol5) (TT1S derivatives - Perkin Elmer gas chromatograph).
Fig. ' 7 - Gas chromatogram of the sterol fraction -of peanut oil (S:imp7.e no. 11). 1) cholesterol; *) brassi.casterol; 2) campes:.erol; 3) stiI;r'zst('rol.; 4) 0--sitosterol (Tl:S derivatives - Perkin Elmer gas chromatograph). A I ig
Fig. g- Gas chromatogram of the sterol. fraction of peanut oil (Sample no. 12). 1) cholesterol.; 2) campesterol; 2 3) s$^ igmasterol; 4) R-sitosterol; 5) ®`-stigmastanol (TMS derivatives - Perkin Elmer gas chromatograph).
I
Fig. 9° Gas chron:ato^;rarn of t.-:r sterol. fraction of peanut oi7. (Sample no. 13). ].) cholesterol; 2),^camnesterol; 3) sti^;masterol; 5) c^ - st^ ^;rn:istanol ( 'l'i:S derivatives - Perkin Elmer gas ct:rom,itoCraph Fig. 10 - Gas chromatogram of the 5 sterol:. fraction of soybean oil (Sample no. 17). 1 1) cholesterol; 2) brassicasterol; 3) campesterol; 4) sggmasterol; 5) p-sitosterol; 6)!Y-stigmastanol (TMS derivatives - Carlo Erba gas chromatograph).
3
4
!
3
Fig. 11 - Gas chromatogram of the sterol. ,fraction of soybean oil Sanple no. 18). 1).cholesterol; 2) brassicasterol; 3) campesterol; 4) sUgmasterol; 5) p-sitosterol; 6)!Y-stigmastanol (TMS derivatives - Perkin Elmer gas chro.datograph). 21 Fig. 12 Ga§ chromatogram of the sterol._ fraction of soybean oil (Sample no. 19). 1) cholesterol; 2) brassicasterol; campesterol; 4) stàigmasterol; 5) 0-sitostero1; 6) A4igmastanol (TMS derivatives - Carlo .r...rba gas chromatograph).
3
5
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4
sterol
In late, :ninir: sti co :mnp un %tigin
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Fig. 13 - Gas chromatogram of the ()i sterol fraction of soybean oil (Sample no. 20). 1) cholesterol; 2) brassicasterol; :uqp. 3) campesterol; 4) - sggmasterol; sta 5) 0-sitostero1; 6) à ( -stigmastanol vr.at (TMS derivatives - Perkin Elmer -unt, gas chromatograph).
260 LA RIVISTA ITALIANA SOSTANZE GRASSE • VOL. L AGOSTO F. 22.
32
1
Fig. 14 - Gas chromatogram of the sterol fraction of grape seed oil.(Sample no. 22). cholesterol; 2) campesterol; . 13 stigmasterol; 4) 5-sitosterol; 4 5)A 7-stigmastanol (TMS derivatives - 3 Perkin Elmer gas chromatograph).
Fig. 15 - Gas chromatogram of the sterol fraction of grape seed oil (Sample no. 23). 1) cholesterol; 2) brassicasterol; 3) campesterol; 4) stigmasterol; 5) p-sitq sterol; 6)4 7-stignastanol (TM3 derivatives - Perkin lilmer gas chromatograph). . h
Fig. 16 - Ga s chromatogram of the j23 sterol fraction of sesame oil (Sample no. 24). ' 1) cholesterol; 2) campesterol;
3) s-ggmasterol; 4) • - sitosterol; ‘ 5f-stigmastanol (TMS derivatives- Ferkin Elmer gas chromatograph).
à
Fig. 17 - Gas chromatogram of the Fi• sterol fraction of sesame oil roJj- (Sample no. 26). 1 cot choltsterol; 2) campesterol; 3 s4igmastero1; 4) 0-sitosterol; 5 5W-stigmastano1 (TMS derivatives Carlo Erba gas chromatograph).
262 LA RIVISTA ITALIANA DELLE SOSTANZE GRASSE - VOL. L AGOSTO 22 Fig. 18 - Gas chromatogram of the sterol_ fraction of sesame oil (Sample no. 27). 1) cholesterol; *) brassicasterol; 2) , campesterol; 3) stigmâstrrol; 4) 5-sitesterol; 5) G'-stigmastanol (TMS derivatives - Perkin Elmer gas . chromatograph).
5
3 4
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Fig. 19 - Gas chromatogram of the sterol . fraction of safflower oil (Samrle no. 28). 1) cholesterol; 2) campelgSrol; 3) stigma- sterol; 4) unidentified sterol; 5) p-sito- sterol; 6)A 7-stigmastanol (TMS derivativei Perkin Elmer gas chromatograph).
RIVISTA ITALIANA IDELLL SOblANLt UF 2 li [U. 6 2 3 Fig. 21 Gas chromatogram of the sterol fraction of safflower oil (Simple no. 31).. 1 1) cholesterol; 2) cnmpesterol; 3) stigmnsterol; 4) unidentified stergl; 5) P-sitosterol; 6)2Y-stigmastanol (TMS derivatives ; Perkin Elmer chromatograph). LA RIVISTA ITALIANA DELLE SOSTANZE GRASSE VOL. L - AGOSTO 1S.1 .r...\J Fig. 22 - Gas chromatogr-3m of the stF .rol ', fraction of sunflower oil 4 (Sample no. 32). 1) cholesterol; 2) campesterol; 3) stigmasterol; *) unidentified s.^rol; 4) S-sitosterol; 5) ^ -stigmastanol (Tr:S derivatives Perkin Elmer gas chromatograph). ' 5 n 3 2 A ! U V MM Fig. 2^- Gas chromatogram of the sterol fraction of sunflower oil (Sample no. 33)- 1) cholesterol; 2) c=jmpesterol, 3) stimasterol; 4) (^-si;tosterol; 5) n7-stip,mastanol (TMS ders.vqtives Perk9.n Elmer r-as c'•iromatograph). LC^i,.rr. ._.....^. ..^...- ^..^^.,...^ .....^..- ..n. , .nn.^rn .n-... 27 of the s• Fig. 24 - Gas chromatogram sterol fraction of sunflower oil (Sample - no. 34). 1) cholesterol; 2) camresterol; gigmasterol; 4) P-sitosterol; 5 ,Vrstipmastarol (TMS derivatives Perkin Elmer gas chromatograph). 2 Fig.• 2é • ) colE Fig. 25 - Gas chromatorram of the sterol fraction of sunflower oil (Sample no. 36). 1) cholesterol; 2) campesterol; 3) stigmasterol; 3) unidentifj7ed sterol; 4) q-sitosterol; 5) - stigmastar,o1 (TMS derivatives - Perkin lruer gis chro7lato!-raPh). .• 28 • 4 e* Fig. 26. - Gas chromatogram of the sterol . frction of corn oil (Samtle no. 1 •cholesterol; 2) campesterol; 3 sigmasterol; 4) f3 -sitosterol; 5 à -stigmastanol (TMS derivatives Perkin Elmer gas chromatograph). 3 Fig. 27 - Gas chromatogram of the • stero] fraction of corn oil (Sample no. 38). -;,)es • 1) cholesterol; 2) campesterol; 3) stigiyastnrol; 4) Ç-sitosterol; 5) 5)4 -stigmastanol (TMS derivatives Perkin Elmer gas chromatograph). LA RIVISTA ITALIANA DELLE SOSTANZE GRASSE - VOL. L AG0510 1 973 267 29 BIBLIOGRAPHY 1) DE Zorn G., CAPELLA P., La Chimica e PInclustria, 40, 651 (1933). 2 2) DE Zorn G., CAPELLA P., JAciNT G., Fette Seifen Anstr., 61, 114 (1959). — • 3) DE Zorn G., CAPELLA P., JACINI G., 0111 Min. Grassi Saponi, /0, 431 (1960). 4) JAcrNI G., DE Zorn G., CAPELLA P., ARPIN° A., Inf. Oléic. Int., 9, 81 (1960). 5) CAPELLA P., DE ZOTTI G., RtccA G. S., VALENTINI A. F., JAct>tt G., J. Ans. Oil Chem. Soc., 37, 564 (1960). 6) CAPELLA P., Nature, 190, lb! (1961). 7) CAPELLA Zorrt G., RICCA G. S., VALENTINriv,%.. P. DE ., _b• e». G., Riv. Sost. Grasse, 38, 198 (1961). 8) JAC'S( G., CAPELLA P., Riv. Sost. Gras, 39, 670 (1,. 9) CAPELLA P., FEDELI E., CIRIMEIE. M., JACINI G., R Ital 40, 603 (1963). Grasse, 10) CAPELLA P., FEDELI E., CIRIMELE M., LAN7-ANI A., l'Aetul G, Ital. Sost. Grasse, 40, 645 (1963). liv. 11) CAPELLA P., FEDELI E., CIRINIELE M., LANym A., Ni c. Ris'. Ital. Sost. Grasse, 40, 660 (1963). 12) CAPELLA P., EEDEL1 E., CtramELE M., Chem. • 77- . t-71 (1963). • _ 13) JAcINI G., Atti del Symposium I.F.M.A. 'Wiesbaden, ..1) Aprile 1963, pag. 13. 14) CAPELLA P., FEDELI E., CIRIMELE M., CHAVERON H., R.Rev F rr Corps Gras, 11, 583 (1964). 15) FUMAGALLI R., CAPELLA P., vANDENHEuve. J. A., Anal. Bioch. 1 10, 377 (1965). 16) WALDECO M., WOLFF J. P., Les costituants de l'insapnnifiabk Journée d'étude I:T.E.R.G. (1965). 17) Runcoi.vsKf A., JACINI. G., CAPELLA P., CIRIMIIE M., kiy, Ital. Sost. Grasse, 43, 89 (1966). ' • 18) FEDELI E., LANZA.•II A., CAPELLA P., JACINI G., J..Am. Chem. Soc., 43, 234 (1966). 19) WALDECO M., Rev. Franç. Corps Gras, .13, 101 (1966). - 20) CoLsacocLu M., Rev. Franç. Corps Gras, 13, 261 (1966). 21) CHAVEROM H., Rev. Franç. Corps Gras, 14, 21 (1967). 22) KARLESKIND A., Rev. Franç. Corps Gras, 14, 251 (1967). 23) KAITLESKIND A., Chimie Analytique, 86, 49 (1967). : 24) DuPEnom P., C. R. Acad. Sci., Paris Ser. D. 265, 409 (1967). 25) KNIGHTS B. A., J. Gas Chrom., 5, 273 (1967). 26) JACINI G., FEDELI E., LANZANI A., J.A.O.A.C., 50. 84 (1967).. 27) KARLESKIND A., Rev. Franç. Corps Gras, 15, 379 (1968). 28) FEnELT E., Rev. Franç. Corps Gras, 15, 281 (1968). 29) WoLpF J. P., Riv. Ital. Sost. Grasse, 45, 634 (1968). 30) Work-P J. P., Manuel d'analyse5 des corps gras, Azoulay, • Paris, 1968. - • 31) BOEKENOOGEN H. A., Analysis and characterization of oils fats and fat products, Vol. II. London Intersdience blishers, 1968. 32) CAPELLA P., Losi G., Atti VI Congresso Studi Igiene Bologma, 1-3 Aprile 1968. 33) GRACTAN J., MAnrEt L, Grasas y Aceites, 20, 231 (1969). 34) MORDRET F., Rev. Franç. Corps Gras, 16, 639 (1969). 35) rscogNIA E., MoNAcart R., Scienza Alim., 16, 423 (1970).' 36) AMATI A., CARRARO ZANIRATO F., Pow G., Riv. It. Sost. Gras- se, 48, 39 (1970). 31) MANZONE A. M., BONIFORTI L., MoNAcEnt R., liv. It. Scat Grasse, 48, 416 (1971). 38) WoLrp J. P., KARLESKIND A., Re!. presentata alla CITO. Torremolinos, 1419 Giug-no 1971. 39) TISCORNIA E.. BErrrn-rx G. C., liv. It. Sost. Grasse, 49, 3 (19771 40) KARLESKIND A., AUDIAU F., WoLIT J. P., Rev. Franç. Corp Gras, 12, 399 (1965)- 41) KARLESKIND A., AUDIAU F., Waif' J. P., Rev. Franç. Corps Gras, 13, 165 (1966). 42) WOLFF J. P., Inf. Oléic. Inter. N. S., 36, 125 (1966). :- 43) 1.1rotFP J. P., liv. Ital. Sost. Grasse, 45, 634 (1068). :24' 44) Worrz I-I. jr.. M‘RTIN. H. F., J. I3iol. Chem., 236, 1312 (19611 45) LUKKAINEN T., VAKnEz‘r HEWES. W. LA., ITAAIITI E. 0./. HORNING E. C., 13iochim. Biophis. Acta, 52, 599 (1961)... 46) VANDEN Minya W. J., STOVALL J., IloaNtNc E. C., Biochint Biophys. Acta, 43 595 (1961). 47) CLAYTON R. 13.. Nature, 190, 1071 (1961). 48) HORNING E. C., VANDEN HE.trvEt. W. J. A., CREECH 13. d- Methods of I3iochemical Analysis. D. Glick Interscience. • Sohn Wiley, New York, 1963. Vol. XI, pag. 69. 49) CtAYroN R. 13., Biochem., /, 357 (1962). 50) KNIGHTS B. A., J. Gas Chromatog., 2, 160 (1964). 51) Kmcwrs B. A., J. Gas Chromatog.. 2, 338 (1964). I 52) KUKSIS A., Can. J. Biochem„ 42, 407 (1964). 53) ROZANSKI A., Anal. Chem., 38, 36 (1966). 54) EtsNER 3.. IvEnsoN J., biloziNco A. K., PRESTONE D„ J.A.O.A.C- 48. 417 (1965). 55) Fédération Internationale d'Oléiculture, Contrôl de • is pûreté des huiles d'olives par l'étude de la composition des stérols. Madrid, 18 Novembre 1968. 56) REcouar I. II., BEERTHUIS R. K., Fette Seifen Anstr, 619 (1963). 57) Eïsin 3.. FIRESTONE D., J.A.O.A.C., 46, 542 (1963). 58) Norme Italiane per il Control lo dei Gr-iissi e Derivati. Ed. 1957 - Stipp. 1971. 59), ENGLER A., Syllabus der i'flarenfamilien-Gebril der iice-rfi' traeger Berlin, Nikolassee 1964. . .. FOREIGN BIBLIOGRAPHIC ITEMS 32) CAPELLA,P., LOSI, G. Proceedings of the VI Congress of Studies on Food Hygiene. Bologna, 1-3 April, 1968. 38) WOLFF, J.P., KARLESKIND, A. Report presented at III CITO - Torremolinos, 14-19 June, 1971. 58) Italian rules for the control of fats and derivatives II Ed. 1957 - -- Suppl. 1971. 59) Syllabus of Plant families.