Sterol composition inCoincya (Brassicaceae)

Sterol composition was determined for seed oils and leaf waxes in eleven taxa belonging to the genusCoincya (Brassicaceae) on the Iberian Peninsula (Spain and Portugal). Seed sterols ranged from 1.2 to 6.7%. The major components were sitosterol (42.6–54.6%), campesterol (20.4–33.2%), and brassicasterol (10.8–23.5%). In leaf waxes, the major free sterols were sitosterol (40.9–74.2%), campesterol (9.6–17.0%), and cholesterol (4.6–17.0%). In leaf wax esters, the major sterols were sitosterol (22.2–56.5%), cholesterol (7.3–32.8%), and campesterol (5.8–25.6%). An apparent substitution of brassicasterol in free sterols from the seeds by cholesterol in free sterols from the leaves was observed. There was an increase of cholesterol in sterols from leaf wax esters with respect to free sterols from leaves and seeds. InC. monensis subsp.nevadensis, the composition in sterols from leaf waxes may be an adaptation to low temperatures.     

Leaf wax alcohols inCoincya (Brassicaceae)

Free and ester alcohol compositions have been determined for leaf waxes in ten taxa belonging to the genusCoincya (Brassicaceae) on the Iberian Peninsula (Spain and Portugal). Size of leaf wax alcohols in the genusCoincya varies between 20 and 31 carbon atoms. This series is dominated by alcohols with an even number of carbon atoms. The most abundant alcohols are C₂₄, C₂₆ and C₂₈ among even and C₂₅, C₂₇ and C₂₉ among odd alcohols, both in free alcohols and in wax esters.     

Fatty acid composition of some pine seed oils

The fatty acid composition of seeds from seven species of the genusPinus (P. pinaster, P. griffithii, P. pinea, P. koraiensis, P. sylvestris, P. mughus, andP. nigra) was established. Pine seeds are rich in oil (31–68% by weight) and contain several unusual polymethylene-interrupted unsaturated fatty acids with acis-5 ethylenic bond. These are thecis-5,cis-9 18:2,cis-5,cis-9,cis-12 18:3,cis-5,cis-11 20:2, andcis-5,cis-11,cis-14 20:3 acids, with a trace ofcis-5,cis-9,cis-12,cis-15 18:4 acid. Their percentage relative to total fatty acids varies from a low of 3.1% (P. pinea) to a high of 30.3% (P. sylvestris), depending on the species. The majorcis-5 double bond-containing acid is generally thecis-5,cis-9,cis-12 18:3 acid (pinolenic acid). In all species, linoleic acid represents approximately one-half the total fatty acids, whereas the content of oleic acid varies in the range 14–36% inversely to the sum of fatty acids containing acis-5 ethylenic bond. The easily available seeds fromP. koraiensis appear to be a good source of pinolenic acid: their oil content isca. 65%, and pinolenic represents about 15% of total fatty acids. These values appear to be rather constant.Pinus pinaster, which is grown on several thousand acres in the southwest of France, is an interesting source ofcis-5,cis-11,cis-14 20:3 acid (7% in the oil, which isca. 35% of the dehulled seed weight), an acid sharing in common three double bonds with arachidonic acid. Apparently,P. sylvestris seed oil contains the highest level ofcis-5 double bond-containing acids among pine seed oils that have ever been analyzed.     

Fatty acid variation in seed oil amongOcimum species

Content, fatty acid composition, and glyceride profile of oil from seeds of seven basil (Ocimum sp.) chemotypes were determined. The species studied includedO. basilicum, O. canum, O. gratissimum, andO. sanctum. The oil content ranged from 18 to 26%, with triglycerides comprising between 94 and 98% of extracted neutral lipids. The major acylated fatty acids were linolenic (43.8–64.8%), linoleic (17.8–31.3%), oleic (8.5–13.3%), and palmitic acid (6.1–11.0%). Linolenic acid was similar among the fourO. basilicum chemotypes (57–62%), highest inO. canum (65%), and lowest inO. sanctum (44%). Basil seed oil appears suitable as an edible oil or can be used for industrial purposes, and could be processed in the same way as linseed oil. Preliminary calculations estimate that a hectare of basil could produce from 300 to 400 kg of seed oil.     

Fatty acid composition of melon seed oil lipids and phospholipids

Fatty acid compositions of crude melon seed oil from two different sources were compared. Melon seeds fromCitrullus vulgaris (syn.C. lanatus) contained phosphatidylcholine (PC), lysophosphatidylcholine (LPC) and phosphatidylserine (PS), whereas melon seeds fromCitrullus colocynthis contained only PC and LPC, but not PS. Analysis of the total lipids revealed that the major fatty acid of the oils was 18:2n-6.Citrullus vulgaris seed oil contained 71.3% andC. colocynthis contained 63.4% of 18:2n-6. The predominant fatty acids in theC. vulgaris PC were 18:2n-6 (32.2%), 18:1n-9 (26.4%) and 16:0 (22.2%), whereas theC. colocynthis PC contained 44.6% of 18:1n-9 as the major fatty acid. The level of monoenes in theC. colocynthis variety (46.2%) was different from theC. vulgaris (27.3%). The major fatty acid in the LPC was 18:1n-9 for both varieties. Notably, theC. colocynthis variety did not contain any PS. The major fatty acids in theC. vulgaris PS were 18:1n-9 (37.9%) and 18:2n-6 (33.7%). Of all the phospholipids, LPC contained the greatest amount of monoenes, 48.6–52.4%.     

Fatty acid composition in seed oils of some onagraceae

The seeds ofOenothera picensis, O. indecora, Ludwigia longifolia andL. peruviana (Onagraceae) contained 18.3, 16.4, 13.9 and 10.1% oil, respectively. Chromatographic analyses showed high levels of linoleic acid (>71.5%) in the seed oils.     

Fatty acid composition, extraction, fractionation, and stabilization of bullfrog (Rana catesbeiana) oil

The oil extracted from the fat-storage organ (fat body) of the bullfrog (Rana catesbeiana) was characterized for its fatty acid composition. The main fatty acids were palmitic (18.1%), stearic (4.1%), myristic (2.7%), oleic (31.7%), and linoleic (12.9%) acids. Long-chain polyunsaturated fatty acids were also present in significant amounts, i.e., eicosapentaenoic (1.5%) and docosahexaenoic (4.7%), and were probably derived from the fish meal content of the diet. A partially fractionated oil was extracted from the homogenized and frozen fat body with an oleic acid content of 43.2%. The natural alkaloid boldine, added at 0.5 mg/g oil level, improved the oxidative stability by a factor ranging from 1.7 to 2.4, as assessed by the Oil Stability Index method between 90 and 110°C. The stabilization effect of boldine was higher than that of naringenin, morin, and quercitin and for the synthetic antioxidant butylated hydroxytoluene at the same concentration level.     

The seed oil ofBernardia pulchella (Euphorbiaceae) —A rich source of vernolic acid

The fatty acids from the seed oil ofBernardia pulchella (Euphorbiaceae) have been analyzed by gas chromatography (GC) and GC-mass spectrometry (MS) analysis of their methyl esters. Vernolic acid is the main compound (91%), along with other usual fatty acids. In addition to the quantitation by GC analysis,¹H-nuclear magnetic resonance (NMR) signals from the seed oil have been used to estimate the total epoxy fatty acid content. The structure of vernolic acid has been proven by spectroscopic methods (infrared,¹H, and¹³C-NMR) and by GC-MS analysis of the corresponding silylated hydroxy-methoxy derivative. The 4,4-dimethyloxazoline derivatives of the fatty acid mixture have also been examined by GC-MS, and it was shown that this derivazation reaction is not suitable for the structure analysis of vernolic acid.     

Cryptolepis buchnani seed oil: A rich source of keto fatty acid

A keto fatty acid (9-oxo-cis-12-octadecenoic acid) has been isolated in appreciable amounts (45.9%) fromCryptolepis buchnani seed oil. The identification was based on chemical and spectroscopic methods.     

Fatty acid composition of oil from adapted,elite corn breeding materials

The fatty acid composition of corn oil can be altered to meet consumer demands for “healthful” fats (i.e., lower saturates and higher monounsaturates). To this end, a survey of 418 corn hybrids and 98 corn inbreds grown in Iowa was done to determine the fatty acid composition of readily-available, adapted, elite corn breeding materials. These materials are those used in commercial hybrid production. Eighty-seven hybrids grown in France (18 of which also were grown in lowa) were analyzed to determine environmental influence on fatty acid content. The parents of the hybrids and the inbreds were classified in one of four heterotic groups: Lancaster, Stiff Stalk, non-Lancaster/non-Stiff Stalk, and Other.t-Tests and correlation analyses were performed with statistical significance accepted at a level ofP≤0.05. The findings showed a wide range of fatty acid profiles present in adapted, elite corn breeding materials with ranges for each fatty acid as follows: palmitic acid, 6.7–16.5%; palmitoleic acid, 0.0–1.2%; stearic acid, 0.7–6.6%; oleic acid, 16.2–43.8%; linoleic acid, 39.5–69.5%; linolenic acid, 0.0–3.1%; and arachidic acid, 0.0–1.0%. Small amounts of myristic acid, margaric acid, and gadoleic acid also were found. Three lines had total saturates of 9.1% or less. Thirty-six of thet-tests involving hybrids showed significant differences among heterotic groups. There were small but significant correlations among protein, starch and oil content and the amounts of several fatty acids. Results from the corn grown in France vs. lowa demonstrated a large environmental effect that overwhelmed the genetic differences among lines. This study shows that for some attributes, a breeding program involving adapted corn breeding materials might produce the desired oil. Other types of oil (such as high-oleic) would have to be produced in a different manner, for example, by a breeding program with exotic breeding materials.     

Fatty acid composition of French infant formulas with emphasis on the content and detailed profile oftrans fatty acids

The aim of the present study was to identify and quantitatetrans isomers of C18 fatty acids in some French infant formulas. Twenty powdered infant formulas were purchased in pharmacies and supermarkets in order to assess theirtrans mono- and poly-unsaturated fatty acids content. The fatty acid profiles were examined using methyl and isopropyl ester derivatives. The combination of gas-liquid chromatography, high-performance liquid chromatography, and silver nitrate thin-layer chromatography was needed to describe the detailed fatty acid compositions of the samples, includingtrans isomers of unsaturated C18 fatty acids. All the samples containedtrans isomers of C18∶1 acid (mean level 1.97±0.28% of total fatty acids), with vaccenic acid being generally the major isomer (15 out of 20 samples), thus indicating the origin from bovine milk. All the formulas also contained various isomers of linoleic and α-linolenic acids, but at lower levels.Trans PUFA isomers are the same as those present in deodorized oils. In conclusion, all the infant formulas analyzed in this study contained sometrans fatty acids, including isomers of essential fatty acids. This should be taken into account in the dietary intake of the newborn.     

Fatty acid composition of thirty-five Icelandic fish species

Fat content and fatty acid composition were determined in 35 fish species caught in Icelandic waters from November 1987 to March 1988. These were not only commonly edible species, but also underutilized and less common species, in which the fatty acid composition have not been reported before. The variation int he fat content and the fatty acid composition was found to be large between and within species. The fat content and n-3 fatty acid content varies sevenfold and twentyfold, respectively. An inverse relationship was obtained between the n-3 fatty acids content and the total fat content of the fish species studied. We believe that the data reported here on 35 fish species can be useful for nutritionists and food scientists, to aid them in dietary formulation, nutrient labelling, processing and product developments, as well as for the consumers.     

Triacylglycerol composition of Pinus koraiensis seed oil

The triacylglycerol (TG) composition of Pinus koraiensis seed oil, which contains Δ5 nonmethylene-interrupted (NMI) fatty acids (FA) (the main acid is pinolenic, 18:3 Δ5, 9, 12), was determined. TG were preliminarily separated by argentation thin-layer chromatography (TLC), and the obtained fractions were analyzed by high-temperature gas chromatography (GC) on a capillary column with methyl phenyl silicone phase. Additionally, high-performance liquid chromatography (HPLC) of TG was applied. The FA composition of all TG fractions was identified. The identification of TG was carried out by combining TLC, GC, HPLC, and calculated equivalent carbon numbers of TG standards. The TG species identification was confirmed by comparison of the theoretical recalculated and directly analyzed FA compositions of all TLC fractions of TG. Species of TG with unsaturation degrees of 1 to 7 and trace amounts of saturated and octaenoic TG species were found. Except for minor compounds, 26 TG molecular species of 32 main components were quantitatively determined. The main species were oleoyl dilinoleoylglycerol (14.7%), dilinoleoyl pinolenoylglycerol (10.7%), palmitoyl oleoyl linoleoylglycerol (8.3%), triolein (7.6%), and dioleoyl, linoleoylglycerol (7.4%). Seven TG species contained Δ5 NMI acyl groups. Of these, the major were dilinoleoyl pinolenoyglycerol (10.7%), stearoyl linoleoyl pinolenoylglycerol (6.5%) dioleoyl, pinolenoylglycerol (5.4%), and palmitoyl linoleoyl pinolenoyl-glycerol (5.5%). TG species with two or three NMI acyl groups were not detected.     

Identification of nine acetylenic fatty acids, 9-hydroxystearic acid and 9,10-epoxystearic acid in the seed oil ofJodina rhombifolia hook et arn. (Santalaceae)

In addition to some usual fatty acids, the seed oil ofJodina rhombifolia (Santalaceae) contains nine acetylenic fatty acids [9-octadecynoic acid (stearolic acid) (1.1%),trans-10-heptadecen-8-ynoic acid (pyrulic acid) (20.1%), 7-hydroxy-trans-10-heptadecen-8-ynoic acid (2.3%),trans-10,16-heptadecadien-8-ynoic acid (0.7%), 7-hydroxy-trans-10,16-heptadecadien-8-ynoic acid (0.1%),trans-11-octadecen-9-ynoic acid (ximenynic acid) (20.3%), 8-hydroxy-trans-11-octadecen-9-ynoic acid (12.2%),trans-11,17-octadecadien-9-ynoic acid (1.5%), 8-hydroxy-trans-11,17-octadecadien-9-ynoic acid (1.3%), 9-hydroxystearic acid (<0.1%) and 9,10-epoxystearic acid (0.7%)]. The fatty acids have been analyzed by gas chromatography/mass spectrometry of their methyl ester and 4,4-dimethyloxazoline derivatives. The hydroxy fatty acid methyl esters have been examined also as trimethyl-silyl ethers. Furthermore, the fatty acid methyl esters (FAME) have been fractionated according to their polarity (FAME-A: nonhydroxy; FAME-B: hydroxy fatty acids) and to their degree of unsaturation (FAME-A1/A2; FAME-B1/B2) by preparative thin-layer chromatography and argentation chromatography, respectively. All of these fractions have been analyzed by ultraviolet and infrared spectroscopy, and the fractions FAME-A and FAME-B have been analyzed further by nuclear magnetic resonance (¹H,¹³C, 2D H/C, attached proton test) spectroscopy and gas chromatography/mass spectrometry. This work is dedicated to the 65th birthday of Prof. Dr. K. Pfeilsticker, Institut of Food Science, University Bonn (Germany).     

Fatty acid composition of two new pepper varieties (Capsicum annuum L. cv. Jaranda and Jariza). Effect of drying process and nutritional aspects

Composition in fatty acids of the pericarp and seeds of two new pepper fruits (Capsicum annuum L. cv. Jaranda and Jariza) and the effects of different processing stages on the fatty acid composition of these tissues and of paprika are shown. In the pericarp the polyunsaturated fatty acids (PUFA), linoleic and linolenic, both in the same proportion, are the major acids; in the seed, linoleic is in a very high concentration as compared to in the pericarp. In the pericarp, a storage zone of carotenoid pigments, linolenic acid does not participate in the carotenoid esterification process. From the different lipid patterns, nutritional aspects are deduced. In the drying step the concentrations of constituent fatty acids are constant in the seed, while in the pericarp there is a net increase in the total content of fatty acids.     

Fatty acid composition of meat from ruminants, with special emphasis on trans fatty acids

The fatty acid composition was determined in 39 samples of beef, 20 samples of veal, and 34 samples of lamb, representative of the supply of ruminant meat in Denmark. Five cuts of beef and veal and three cuts of lamb with increasing fat content were selected, and analysis of the fatty acid methyl esters was performed by gas-liquid chromatography (GLC) on a polar 50-m capillary column CP Sil 88 with flame-ionization detection. Lamb had the highest content of saturated fatty acids (52.8±1.8 g/100 g fatty acids), higher than beef and veal (45.3±3.1 and 45.4±0.8 g/100 g fatty acids, respectively). Cis monounsaturated fatty acids were 49.2±3.1, 44.9±1.8, and 37.7±1.7, and polyunsaturated fatty acids were 3.3±0.7, 5.8±2.0, and 5.0±0.1 g/100 g fatty acids in beef, veal, and lamb, respectively. Beef contained 2.1±0.8 g trans C_18:1 per 100 g fatty acids, about half that found in veal (4.0±1.2 g/100 g fatty acids) and lamb (4.5±0.6 g/100 g fatty acids). Trans C_16:1 was 0.24±0.01, 0.14±0.02, and 0.79±0.02 g/100 g fatty acids in beef, veal, and lamb, respectively. Only small variations in trans and other fatty acids could be demonstrated between cuts. The overlap between cis and trans C_18:1 by capillary GLC was verified by argentation-thin-layer chromatography followed by GLC, on three samples of veal and three samples of lamb. In veal 1.0 g, and in lamb 1.4 g trans C_18:1 per 100 g fatty acids were hidden under the cis C_18:1 peak. The mean intake of trans fatty acids from ruminant meat is estimated at 0.2 g/d.     

Characterization of pili nut (Canarium ovatum) oil: Fatty acid and triacylglycerol composition and physicochemical properties

The fatty acid and triacylglycerol composition of pili nut (Canarium ovatum) oil and fractions were analyzed by gas chromatography and reversed-phase high-performance liquid chromatography, respectively. The oil obtained by solvent extraction was low in polyunsaturated fatty acids and high in saturates. The polyunsaturated fatty acid (18∶2 and 18∶3) contents were less than 11%, whereas palmitic (16∶0) and stearic acid (18∶0) were 33.3 and 10.9%, respectively. The saturated fatty acid level of the low-melting fraction oil was reduced from 44.4 to 35.5% and the total unsaturated fatty acid levels were increased from 55.6 to 65% by fractional crystallization. Triacylglycerol analysis showed that the high-melting fraction (HM) from pili nut oil consisted of POP, POS, and SOS+SSO (P=palmitic acid, O=oleic acid, and S=stearic acid) in the proportion of 48.6, 38.8, and 8.7%, respectively. The physicochemical properties of the HM fraction were studied using differential scanning calorimetry and pulsed nuclear magnetic resonance. The results showed that the melting range and solid fat content of the HM fraction were very similar to those isolated from cocoa butter and olive oil. The content of POP played an important role in determining the melting range of the HM fraction. It is suggested that this HM fraction may have applications as a cocoa butter substitute in confectionery products.     

Large-scale preparation of linoleic acid-d2-enriched triglycerides fromCrepis alpina seed oil

Catalytic deuteration ofCrepis alpina seed oil provided a convenient one-step method for the direct synthesis of large quantities of triglycerides enriched with deuteriumlabelled linoleic acid.Crepis alpina seed (19 kg) was crushed, and the oil [74% crepenynic acid (cis-9-octadecen-12-ynoic acid)] was extracted with hexane. After purification by column chromatography (silica gel), > 170-g batches of oil were deuterated with Lindlar catalyst and deuterium (D₂) gas. Purification (silica gel) resulted in > 150-g samples of triglyceride containing 74%cis-9,cis-12-octadecadienoic acid-12,13-d₂ (18:2-d₂) and 14% unlabelled linoleic acid. Pure (> 99%) tricrepenynin was recovered by further fractionation of theCrepis alpina triglycerides on silica gel. Deuteration of this sample produced deuteriumlabelled trilinolein containing linoleic acid-d₂ of > 98% isotopic purity.     

Fatty acid selectivity of lipases: γ-linolenic acid from borage oil

The γ-linolenic acid (Z,Z,Z-6,9,12-octadecatrienoic acid, GLA) present in borage oil free fatty acids was concentrated in esterification reactions that were catalyzed by several preparations of the acyl-specific lipase ofGeotrichum candidum. In this manner, a 95% recovery of the GLA originally present in borage oil (25% GLA) was obtained as a highly enriched fatty acid fraction with a GLA content of >70%. Other fatty acids concentrated in this fraction were the monounsaturated fatty acids with chainlengths of C-20 and longer that were present in the oil. An immobilized preparation ofG. candidum on silica gel also was used for the enrichment of GLA in borage oil. In this instance, a 75% recovery of GLA was obtained, and the supported lipase was reusable (three cycles) with minimal loss in activity. Presented in part at the 84th Annual Meeting of the American Oil Chemists’ Society, Anaheim, California, May 1993.     

Variation in fatty acid composition of the different acyl lipids in seed oils from fourSesamum species

Seeds from different collections of cultivatedSesamum indicum Linn. and three related wild species [specifically,S. alatum Thonn.,S. radiatum Schum and Thonn. andS. angustifolium (Oliv.) Engl.] were studied for their oil content and fatty acid composition of the total lipids. The wild seeds contained less oil (ca. 30%) than the cultivated seeds (ca. 50%). Lipids from all four species were comparable in their total fatty acid composition, with palmitic (8.2–12.7%), stearic (5.6–9.1%), oleic (33.4–46.9%) and linoleic acid (33.2–48.4%) as the major acids. The total lipids from selected samples were fractionated by thin-layer chromatography into five fractions: triacylglycerols (TAG; 80.3–88.9%), diacylglycerols (DAG; 6.5–10.4%), free fatty acids (FFA; 1.2–5.1%), polar lipids (PL; 2.3–3.5%) and steryl esters (SE; 0.3–0.6%). Compared to the TAG, the four other fractions (viz, DAG, FFA, PL and SE) were generally characterized by higher percentages of saturated acids, notably palmitic and stearic acids, and lower percentages of linoleic and oleic acids in all species. Slightly higher percentages of long-chain fatty acids (20∶0, 20∶1, 22∶0 and 24∶0) were observed for lipid classes other than TAG in all four species. Based on the fatty acid composition of the total lipids and of the different acyl lipid classes, it seems thatS. radiatum andS. angustifolium are more related to each other than they are to the other two species.