Freie und gebundene Sterine in rohen und raffinierten Palmölen,Teil II: Sterinhaltige Lipoproteine

Free and Bound Sterols in Raw and Refined Palm Oils, Part II: Sterol Containing Lipoproteins Twelve lipid fractions were isolated from raw palm oil which contain beside sterols, fatty acids and pigments also low amounts of phospholipids and proteins. The very stable complexes can only be decomposed by acid hydrolysis. The composition of sterols and fatty acids in the hydrolysate and the phosphor and nitrogen content in the purified lipid fractions were determined. According to composition and chemical behaviour of these lipid complexes they are sterol containing lipoproteins with strong lipophilic character. In some of these fractions the extremely high cholesterol content is striking which is partly more than 50% of the total sterols. The release of sterols from these complexes during refining might be the reason for the high cholesterol content in some refined palm oils.     

Sterols and Oxidized Sterols in Feed Ingredients Obtained from Chemical and Physical Refining Processes of Fats and Oils

The by-products obtained from conventional chemical and physical refining processes for edible fats and oils are important sources of valuable fatty components such as sterols, tocopherols, fatty acids, etc., and are also used as ingredients in animal feed formulations. Reports on sterol composition and content are limited, and the levels of oxidized sterols in these valuable by-products are unknown. This study analyzed by-product fractions from European refineries intended for use as ingredients in animal feeds for their content and composition of sterols and sterol oxidation products. The complex mixtures of sterol oxidation products were separated and quantified by multidimensional capillary columns, a medium polar DB-17MS and an apolar DB-5MS, in GC and GC–MS. Sterol content ranged from 0.l to 3.4 and 0.03 to 5.0 g/100 g in the by-product fractions collected from chemical and physical refining processes, respectively, while the corresponding ranges for sterol oxidation products were 0.02–17 and 0.02–1.5 mg/100 g.     

Sterin- und Fettsäurezusammensetzung in Keimölen

Sterol and Fatty Add Composition in Germ Oil The sterol and fatty acid composition of 10 various wheat samples and one maize sample were investigated as well in the germ as in the endosperm to determine characteristics for identity and purity controls. A constantly low content of stigmasterol and an extremely high total sterol content are criteria for pure wheat germ oil. Another characteristic is the presence of small amounts of 5-dihydrositosterol and 5-dihydrocampesterol from lipids of the endosperm in germ oils obtained by technology.     

Freie und gebundene Sterine in rohen und raffinierten Palmölen,Teil I: Gehalt und Zusammensetzung der freien Sterine,Sterinester, freien und acylierten Steringlucoside

Free and Bound Sterols in Raw and Refined Palm Oil, Part I: Content and Composition of Sterols, Sterol Esters, Free and Acylated Sterol Glucosides A method for separation and quantitative determination of free sterols, sterol esters, free and acylated sterol glucosides in fats was developed and applied to the investigation of raw and refined palm oil. During refining the content and the composition of all 4 sterol fractions are varying characteristically. Some samples showed an evident increase of the cholesterol level during certain refining steps. Since none of the 4 investigated sterol fractions has such a high cholesterol level, sterols must be present in bound form, which can be liberated during refining and can be determined afterwards by conventional test methods.     

Analysis of sterol fractions from twenty vegetable oils

The unsaponifiables separated from 20 vegetable oils were divided into sterol and three other (less polar compound, triterpene alcohol, and 4-methylsterol) fractions by preparative thin layer chromatography. The amounts of the sterol fractions were more than ca. 30% in the unsaponifiables from all of the oils, except tohaku, pumpkin seed, and fagara seed oils. Composition of the sterol fractions were determined by gas liquid chromatography. Individual components of the sterol fractions were identified by gas liquid chromatography and combined gas liquid chromatography-mass spectrometry. β-Sitosterol was found as the most predominant component in the sterol fractions from all oils, except two, i.e. the sterol fraction from pumpkin seed oil contained no detectable amount of β-sitosterol and the sterol fraction from akamegashiwa oil contained Δ⁵-avenasterol as the most abundant component. Campesterol, stigmasterol, Δ⁵-avenasterol, Δ⁷-stigmastenol, and Δ⁷-avenasterol and also trace amounts (at the very least) of cholesterol and brassicasterol were found in most of the oils analyzed. It may be noted that a large amount (ca. 9%) of cholesterol was detected in the sterol fraction from capsicum seed oil. The presence of 24-methylenecholesterol and Δ⁵-avenasterol in the sterol fraction of akamegashiwa oil was demonstrated by isolation of these sterols.     

Freie und gebundene Sterine in rohen und raffinierten Palmölen,Teil III: Verhalten der sterinhaltigen Lipoproteine bei der Raffination

Free and Bound Sterols in Raw and Refined Palm Oils, Part III: Behaviour of Sterol Containing Lipoproteins during Refining Studies have been carried out about the behaviour of sterol containing lipoproteins during refining. By neutralization and bleaching they are partly separated together with the free fatty acids. One part, however, is splitted mainly during deodorization. Thus content and composition of lipoproteins are changed during refining. The sterols released from lipoproteins are determined together with free sterols. Because of their high cholesterol content increased cholesterol values can be found in sterol determination of refined palm oils.     

Sterols,methylsterols, and triterpene alcohols in threeTheaceae and some other vegetable oils

The unsaponifiables from threeTheaceae (Camellia japonica L.,Camellia Sasanqua Thunb., andThea sinensis L.) oils and alfalfa, garden balsam, and spinach seed oils and shea fat were separated into four fractions: sterols, 4-methylsterols, triterpene alcohols, and less polar compounds by thin layer chromatography. While the sterol fraction was the major one for the unsaponifiables from alfalfa and spinach seed oils, the triterpene alcohol fraction was predominant for the unsaponifiables from all other oils. The sterol, 4-methylsterol, and triterpene alcohol fractions were analyzed by gas chromatography. All the sterol fractions were alike in their compositions, consisting exclusively of Δ⁷-sterols, such as α-spinasterol and Δ⁷-stigmastenol as predominant components together with Δ⁷-avenasterol and 24-methylcholest-7-enol. Obtusifoliol, gramisterol (occasionally accompanied with cycloeucalenol), and citrostadienol, together with several other unidentified components, were found in the 4-methylsterol fractions from all of the oils except shea fat. The 4-methylsterol fraction from shea fat showed a characteristic composition containing a large proportion of unidentified components which had relative retention time greater than that of citrostadienol, while no citrostadienol was detected. β-Amyrin, lupeol, and butyospermol were major components of the triterpene alcohol fractions from most of the oils, but the fraction from spinach seed oil contained cycloartenol and 24-methylene-cycloartanol as predominant components. There is a close similarity in the compositions of unsaponifiables (sterols, 4-methylsterols, and triterpene alcohols) of the threeTheaceae oils. Two sterols, α-spinasterol and Δ⁷-stigmastenol, and five triterpene alcohols were isolated from tea seed oil. Moreover, five unidentified components beside parkeol, butyrospermol, α-amyrin, and lupeol were isolated from the triterpene alcohol fraction of shea fat.     

Characterization of Turkish Olive Oils by Triacylglycerol Structures and Sterol Profiles

A characterization study of Turkish monovarietal olive oils using chemical variables such as fatty acid, sn‐2 fatty acid, triacylglycerol, and sterol composition is presented. A total of 101 samples of Olea europaea L. fruits from 18 cultivars were collected for two crop years from west, south, and southeast regions of Turkey. Olives were processed to oil and olive oil samples were evaluated for their triacylglycerol structures and sterol composition. Oleic acid content ranged from 60.15 to 80.46 % of total fatty acids and represented 70.90–89.02 % of sn‐2 position triacylglycerols. Major triglycerides of oil samples were triolein, palmitodiolein, dioleolinolein, palmitooleolinolein, dipalmitoolein, and stearodiolein. Triolein values were between 24.72 and 48.64 % and compatible with the fatty acid composition. Total sterol content varied from 1,145.32 to 2,211.77 mg/kg and Edremit yagl?k stood out because of its high sterol content. A one‐way analysis of variance revealed significant differences for variables among cultivars. Principle component analysis enabled the classification of common varieties on the basis of analytical data. Sterol composition achieved more relevant discrimination than fatty acid and triglyceride composition. Classification according to geographical origin was performed by discriminant analysis.     

Chemical characteristics of oils from naked and husk seeds of Cucurbita pepo L.

Pumpkin seed oils from naked and husk pumpkin seeds, produced by an industrial process and by laboratory extraction, were evaluated for fatty acid composition, tocopherol, sterol and squalene content. The major fatty acids in the oils from both varieties were oleic, linoleic and palmitic acid, followed by stearic acid. The ratios of monounsaturated to polyunsaturated fatty acids for husk and naked seed oils were about 0.60 and 0.75, respectively. Analysis of tocopherols in industrially pressed and laboratory‐extracted oils showed that husk seed oils had higher amounts of total tocopherols than naked seed oils. Oils extracted in the laboratory had higher amounts of tocopherols than industrial oils. Pumpkin seed oil, in general, had a high level of squalene, which was higher in husk seed oils than in naked seed oils and in extracted than in pressed oils. The total amount of sterols was higher in husk than in naked seed oils and in extracted oil samples. The main sterols were Δ7‐sterols and their content was similar in all samples, but the content of Δ5‐sterols was higher in oil samples of husk pumpkin seed and in extracted than in pressed oils.     

Composition of unsaponifiable lipid from seed oils ofPanax ginseng andP. quiquefolium

The composition of the unsaponifiable lipid, which consisted of squalene, squalene-2,3-oxide, triterpene alcohols, 4α-methyl-sterols, and sterols, of the seed oils ofPanax ginseng andP. quiquefolium, was determined. Squalene was the most abundant component (54%) of the unsaponifiable lipid fromP. ginseng, whereas sterols constituted the principal components of unsaponifiable lipid fromP. quiquefolium. Both ginseng seed oils showed specific features in sterol composition, i.e., 28-isofucosterol (40%) and 24-ethyl-22E-dehydrocholesterol (66%) constituted the most predominant components of the sterol fractions fromP. ginseng andP. quiquefolium seed oils, respectively.     

Sterol composition during the life cycle of the soybean and the squash

Sterol analyses were performed on soybeans and squash at intervals throughout the life cycle from seed to mature seed-bearing plant. The sterols of the soybean (24-methyl-cholesterol, stigmasterol and sitosterol) increased in quantity from that in the seed in each stage examined except for a pause or decrease prior to flowering and a decrease at senescence. Individual sterols remained in the same proportion to each other and changes in content were similar in roots and shoots. In the squash a much more complicated sterol mixture was found, composed primarily of C-7 unsaturated sterols characteristic of Cucurbitaceae. Sterol composition also increased during the life cycle except for approximately two wk in the preflowering to early flowering period. The data indicate low synthesis or high turnover of sterols (or both) in these plants in the weeks at or just prior to flowering.     

Sterinanalyse als Mittel zum Nachweis von Vermischungen und Verfälschungen

Sterol Analysis as Means to Detection of Mixed and Adulterated Fats Sterols are components of all vegetable and animal fats. The identification of fats is often possible by sterol analysis, because their composition is mostly characteristic for a fat. Even adulteration and mixtures with other fats can be detected. For example sterol analysis is very important for investigation of purity and identity of butterfat, olive oils and other expensive food fats.     

Fatty Acid and Sterol Composition of the Seed Oils of Moringa hildebrantii,Brochoneura freneei and Strychnos spinosa

The fatty acid and the sterol composition of Moringa hildebrantii (Moringaceae), Brochoneura freneei (Myristicaceae) and Strychnos spinosa (Loganiaceae) seed oils were evaluated. The seed oil content ranged from 5 to 64.5%. The oils have iodine values from 47 to 79. Investigation by gas liquid chromatography using Carbowax 20 M capillary column revealed fourteen fatty acids, mainly oleic (31-80%). Myristic acid was the major component for B. freneei (54%). Testing for the sterol fraction on an OV 17 column enabled nine sterols to be separated and quantitatively analyzed, mainly β-sitosterol (42-62%), stigmasterol (18-27%) and campesterol (10-24%).     

Composition of Catalpa ovata Seed Oil and Flavonoids in Seed Meal as Well as Their Antioxidant Activities

In view of the growing demand for vegetable oil, currently exploration of some non‐conventional oils is of great concern. This study firstly analyzed the contents of fatty acids, phytosterols, and tocopherols in Catalpa ovata seed oil collected from four different Provinces in China. Then the composition of flavonoids as well as their antioxidant activities in defatted seed meal was determined. The results showed that the relative oil content in C. ovata seeds ranged from 24.0 to 36.0 % and seed oil was mainly composed of fatty acids linoleic acid (43.4–50.1 %), α‐linolenic acid (23.8–24.4 %), and oleic acid (13.1–16.2 %). The content of unsaturated fatty acids was up to 85.0 %. Sterol in seed oil mainly contained campesterol, stigmasterol, and β‐sitosterol. β‐sitosterol accounted for 74.0 % of the total sterol. The tocopherol content was 173.0–225.7 mg/100 g. Defatted seed meal from Hubei Province showed the highest content of total flavonoids (11 mg/g) and the strongest activities for DPPH radicals scavenging, ABTS radicals scavenging, and ferric reducing antioxidant power compared with other defatted seed meal in this study. Seven flavonoids were identified from C. ovata seed meal. These results suggest that C. ovata seeds may be developed as a new source of oil and can also be properly used in pharmaceuticals and cosmetics.     

Hauptkomponenten der 4-Methylsterin- und Triterpenfraktion von 12 Pflanzenfetten und ihr Einfluß auf die Sterinanalyse

Main Components of 4-Methyl-Sterol and Triterpene-Fraction of Twelve Vegetable Fats and their Influence on the Sterol Analysis 4-methylsterols and triterpenes are accompanying substances of the sterols in the unsaponifiable with partly very similar chromatographic properties. In 12 different vegetable fats both content and composition of the main components of these three substance groups were investigated and their influence on the sterol analysis was found out. For most fats a thin-layer chromatographic separation of the 4-methyl-sterols and triterpenes from the sterols is necessary to make possible an exact determination of the sterol content and the sterol composition by gas chromatography.     

Zusammensetzung einiger koreanischer Samenöle

Composition of Some Korean Seed Oils Seeds of some Korean plants, used in popular medicine, were investigated for oil content, fatty acid composition and sterol composition. Two seed oils of conifers contained unusual polyenoic acids having 18 and 20 C-atoms. cis-5, cis-9, cis-12-Octadecatrienoic acid was identified as one of the major component fatty acids in the seed oil of Pinus koraiensis. Apart from their medicinal use, some of the investigated seeds of angiosperms, such as perilla, sesame or rape, are used mainly for oil extraction. The oils in the varieties cultivated in Korea do not differ in their fatty acid composition from the figures considered as average composition in Europe.     

Sterol composition of 19 vegetable oils

The unsaponifiables from 19 vegetable oils were divided into a sterol and three other fractions by thin-layer chromatography. All except olive and palm kernel oils gave the sterol fraction in a large quantity. Compositions of the sterol fractions were determined by gas liquid chromatography. Identification of each sterol was carried out by gas liquid chromatography and combined gas chromatograph-mass spectrometry. Campesterol, stigmasterol and β-sitosterol were present in all oils, and a minor amount of cholesterol in majority of the oils. Brassicasterol occurrence was widespread but its content was extremely small in oils other than rapeseed oil. Other sterols, presumably δ⁷-stigmastenol and δ⁵- and δ⁷-avenasterol were detected in most of the oils.     

Effect of Gamma Irradiation on Biochemical Properties of Grape Seeds

In the present study, grape seed samples (Alicante Bouschet, Cabernet Franc, Cinsault, Merlot, Shiraz) were treated with 1.0, 3.0, 5.0, and 7.0 kGy of gamma radiation. Effect of irradiation dose on free fatty acids (FFA), peroxide value (PV), sterol, fatty acid composition, phenolic content, antioxidant activity of the seed oils, and chemical (dry matter, fat, ash, total sugar, invert sugar) changes of grape seeds were determined. Regarding fatty acid composition, oleic acid (C18:1) and linoleic acid (C18:2) levels decreased. β-sitosterol content with a highest percentage among sterols in grape seed oils decreased due to gamma irradiation. Generally gamma irradiation increased free fatty acids and peroxide value of the oils; however, phenolic content and antioxidant capacity of grape seeds decreased.     

Effects of dietary peanut oil on serum lipoprotein patterns of rats

Oils prepared from two varieties of peanuts and from a hybrid corn having linoleic acid concentrations substantially different from the respective commercial oils were compared with commercial oils for their effects on serum lipids of weanling female rats. In the first experiment, serum lipid patterns appeared to reflect linoleic acid content of the dietary oil. However, with a longer feeding period in the second experiment, serum lipid patterns were determined by the plant source of the dietary oil rather than its linoleic acid content; all peanut oils differed from both corn oils in their physiological effects. Diets containing triglyceride, hydrocarbon and sterol fractions obtained by liquid chromatography of peanut and corn oils were fed to female rats. The data provide no evidence that the hydrocarbon or sterol fractions of peanut oil are responsible for its unusual atherogenicity when fed as the sole fat source or that similar fractions from corn oil are protective against the effects of peanut oil.     

Triterpene alcohols and sterols of vegetable oils

Triterpene alcohols and sterols were separated by thin-layer chromatography and gas-liquid chromatography from the unsaponifiable fractions of the following 18 vegetable oils: linseed, peanut, olive, rice bran, palm kernel, corn, sesame, oiticica, palm, coconut, rapeseed, grape seed, sunflower, poppy seed, castor, tea seed, cocoa butter and soybean. Two triterpene alcohols, cycloartenol and 24-methylene cycloartanol, were found in all of the oils except soybean oil, which contained only cycloartenol. Triterpene alcohols such as α- and β-amyrin, euphorbol, butyrospermol and cyclolaudenol also were encountered occasionally. Three sterols, β-sitosterol, stigmasterol and campesterol were present in all of the oils. In addition a fourth sterol, not yet idenfified, was found in oils of palm, palm kernel and sunflower in varying amounts. This unknown sterol and brassicasterol were found in rapeseed oil in addition to the three sterols that were common to all of the oils studied. Experiment Station for Fats and Oils, National Center for Lipochemistry of National Research Council, Milan, Italy.