Major Unsaturated Acids Research Articles

GC‒MS analysis of fatty acids of Malvaviscus arboreus leaves

Malvaceae plants have been reported to produce a wide range of structurally varied fatty acids. Therefore, in this work, the fatty acid content of Malvaviscus arboreus Cav. leaves was investigated using gas chromatography-mass spectrometry (GC‒MS) technique. A total of 17 fatty acids were characterized, with noticeable abundance of saturated acids (50.98%) that were principally dominated by palmitic acid (32.15%). Moreover, a number of mono-, di-, and tri-unsaturated fatty acids were detected constituting 24.92% of the total identified acids, of which 5,12-octadecadienoic acid (7.66%) was the major unsaturated acid identified. As a common feature of several genera of the Malvaceae family, some unusual fatty acids were identified from the saponifiable fraction of M. arboreus leaves, namely 9-methyl tetradecanoic, 3-methoxy pentadecanoic, and 9-heptadecynoic acids, that along with tetracosanoic, 9-octadecenoic, 13-octadecenoic, 5,12-octadecadienoic, and 9,11,15-octadecatrienoic acids, were also interestingly reported herein for the first time in the genus Malvaviscus.

Antiradical and antimicrobial properties of cold-pressed black cumin and cumin oils

Cold-pressed black cumin seed oil (BCSO) and cumin seed oil (CSO) were evaluated for their fatty acid profiles, phytosterol and tocopherol contents, antiradical properties and inhibition of microbial growth. The main fatty acids in BCSO were linoleic followed by oleic and palmitic acids. Petroselinic acid (C18:1n-12) was the main fatty acid in CSO, while linoleic acid was the second major unsaturated acid. Six sterol compounds were measured in BCSO and CSO, wherein the sterol marker was β-sitosterol. α-Tocopherol constituted 45% of tocopherols in BCSO, while β-tocopherol was the main component in CSO. BCSO and CSO oils had higher antiradical action against DPPH· and galvinoxyl radicals than virgin olive oil. Antimicrobial properties of BCSO and CSO were studied, and the results revealed that CSO inhibited the growth of all microorganisms tested, while BCSO inhibited the growth of all microorganisms tested except A. niger and A. flavus. BCSO and CSO had a drastic effect on the biosynthesis of protein and lipids in cells of B. subtilis.

Seed Yield and Quality of Winter Oilseed Rape as Affected by Nitrogen Rates, Sowing Time, and Fungicide Application

This work reports the results of studies on the impact of sowing times (three dates), application of fungicides (protected and unprotected plots), and nitrogen rates (five treatments) on the seed yield, contents of crude protein (CP), glucosinolates (GSL), and crude fat (CF) in seed and on major unsaturated acids (oleic C18:1, linoleic C18:2, and linolenic C18:3) in oil of winter rape (Brassica napus L.) cv. Kasimir. A split–split plot design was used in the field trial conducted on Endocalcari–Epihypogleyic Cambisol during 1998–2002. Seed samples were analyzed by near infrared spectroscopy. ANOVA analysis was used to assess the significance of each factor for the yield and quality of seed of the tested cultivar. The seed yield significantly depended on harvest year, N rates annually, sowing time in three experimental years, and fungicide application in two years. CF and CP concentrations were significantly affected by sowing time and N rates each year of the experiment. A significant effect of fungicides was identified only in one harvest year. GSL concentration was significantly affected by sowing time in three years, by fungicides in two years, and by nitrogen rate annually. The effect of the studied factors on the composition of major unsaturated acids was inconsistent. Sowing time significantly affected the content of all three unsaturated acids in two years and fungicides only in one of the four harvest years.

Vitamin, Free Amino Acid and Fatty Acid Compositions of Some Marine Planktonic Microalgae Used in Aquaculture

Vitamin, free amino acid and fatty acid analyses were carried out on selected different microalgal species used in aquaculture as an evaluation for proposed cosmetic use. In most cases greater amounts of vitamins were obtained in the microalgae than in the usual human food sources. On a dry weight basis, tyrosine, alanine and glutamic acid were the main free amino acids found in the strains studied. Considering fatty acids and total lipid, the ratio of polyunsaturated fatty acids (PUFA) to saturated fatty acids remained nearly constant for the species analyzed and PUFA were dominant. For both Chaetoceros calcitrans and Skeletonema costatum, myristic and palmitic acids were the main saturated acids and EPA the major unsaturated acid, but for Tetraselmis suecica palmitic acid represented 29.4% of total fatty acids

Identification of long-chain fatty acids and alcohols from human cerumen by the use of picolinyl and nicotinate esters.

Human cerumen was hydrolysed with base and the constituents were examined as trimethylsilyl (TMS), methyl ester/TMS, picolinyl/TMS and nicotinate/TMS derivatives by gas chromatography and gas chromatography/mass spectrometry. A sample was also reacted with osmium tetroxide for double bond location. The major constituents were cholesterol, squalene and several series of long-chain fatty acids and alcohols. These latter compounds had chain lengths of 12-26 carbon atoms and were predominantly either straight-chain saturated or straight-chain unsaturated compounds. Saturated branched-chain acids with methyl groups predominantly on even-numbered carbon atoms were present but were less abundant. Unsaturated, branched-chain acids were also present. The major unsaturated acids contained unsaturation at the delta-6-position or were derived from these acids by chain elongation. The compounds were similar to those found in vernix caseosa. The mass spectra of picolinyl esters were, for the first time, shown to be capable of determining both the position of unsaturation and methyl branching in the same molecule.

Fatty acid composition of seed oils of some members of the meliaceae and combretaceae families

AbstractSeed oils of some members of the Meliceae (six) and Combretaceae (three) were analyzed for their fatty acid composition. In oils of members of both families palmitic acid was the most abundant saturated acid. Trace amounts of short chain (C12–C14) and long chain (C20–C22) saturated acids were detected in some members of the two families. Oleic acid was the most abundant unsaturated acids in the oils of four members of the Meliaceae. However, in the oils ofCedrella odorata andLovoa trichilloides, dienoic acid (C18:2) was the major unsaturated acid. Strikingly high levels of trienoic (C18:3) and monoenoic (C16:1) acids were detected in the seed oils ofC. odorata andEnthandrophragma angolense, respectively. Oleic acid also was the most abundant unsaturated acid in the Combretaceae. The nutritional value and industrial potentials of these oils are given.

Fatty acid composition of seed oils of some members of the leguminosae family

Seed oils of ten leguminous tree crops were investigated for their fatty acid composition. Saturated acid components of the leguminous seed oils analysed revealed that low molecular weight acids (capric and lauric) did not commonly occur. On average, palmitic acid (19·4 ± 10·6) was the only major saturated acid present. However, within the subdivision Mimosoideae stearic acid content was slightly higher than in the subdivision Caesalpinoideae. Two members of the subdivision Mimosoideae— Tetrapleura tetraptera (13·9%) and Parkia clappertoniana (19·7%)—showed unusually high levels of behenic acid (22·0). Lignoceric acid (24·0) was not detected in any of the oils analysed. The major unsaturated acids in the seed oils of the leguminous crops investigated were oleic and linoleic acids, both comprising about 68·3% of the component acids. All members except P. africana (Mimosoideae) and Pterocarpus osun (Papilionaceae) were richer in linoleic acid than in oleic acid. Linoleic acid even comprised more than 50% of the component fatty acids in the seed oils of Adenanthera pavonina, T. tetraptera, D. oliverii and Bauhinia monandra. Very low levels of linolenic acid were detected in all the leguminous seed oils investigated. The nutritional implications of the component fatty acids are discussed.

Fatty acids and fatty aldehydes of buffalo seminal plasma and sperm lipid

Analysis of the fatty acids of total and neutral lipids, glycolipids, phospholipids and gangliosides of buffalo spermatozoa and seminal plasma showed that there were high levels of polyunsaturated acids. Neutral lipids were the richest in polyunsaturated acids (55% in spermatozoa and 61% in seminal plasma). The major saturated acid of all the principal classes was stearic acid and the major unsaturated acid was docosahexaenoic acid (22:6omega3) except in the neutral lipids in which it was arachidonic acid (20:4omega6). The major aldehyde was palmitaldehyde (16:0) in buffalo sperm lipids and docosanal (22:0) in seminal plasma. More than 50% of the total aldehydes was contributed by aldehydes with a chain length greater than 18 carbon atoms.

Detailed structure of sphingomyelins and ceramides from different regions of bovine kidney with special reference to long-chain bases

1. 1. Sphingomyelins of whole bovine kidney (14.4 mg/g dry weight) have been isolated and characterized in detail. 2. 2. After selective N-demethylation and gas chromatography and mass spectrometry the polar part was shown to be N, N-dimethylphosphorylethanolamine, in accordance with an original phosphorylcholine structure. No phosphonate analogue was found. 3. 3. The fatty acids were straight-chain, mainly saturated C 16, C 18, C 22, C 23 and C 24 acids. The major unsaturated acid was C 24 cis-monoene. Small amounts of trans-monoenic acids were also present. 4. 4. The long-chain bases had a very complex pattern (about 30 molecular species). By a series of improved methods the bases were converted to dinitrophenyl derivatives, fractionated and structurally characterized. 5. 5. Three groups of bases were found by thin-layer chromatography; saturated dihydroxy bases, unsaturated dihydroxy bases and saturated trihydroxy bases, in the approximate ratio of 2:20:3. 6. 6. The paraffin chain distribution was similar for the three groups of bases; with C 16–C 20 bases, dominated by C 18 homologues, and with unusually high amounts of C 17 bases. No evidence for bases below C 16 was found. 7. 7. By thin-layer chromatography, infrared spectroscopy and optical rotation measurement the geometry and configuration were assigned for the major part of the three groups of bases. Thus the major saturated dihydroxy base was dihydrosphingosine ( d- erythro-1,3-dihydroxy-2-aminooctadecane), the major unsaturated dihydroxy base sphingosine ( d- erythro-1,3-dihydroxy-2-amino-4- trans-octadecene), and the major trihydroxy base phytosphingosine ( d- ribo-I,3,4-trihydroxy-2-aminooctade-cane). 8. 8. 10–15% of the bases were branched-chain bases, with a methyl branch in Position 2 or 3 from the methyl end. The major bases had the branch in the same position (16) from the polar end irrespective of total chain length. 9. 9. A minor dienic base was identified as eryth-I,3-dihydroxy-2-amino-4, 14-octadecadiene, probably identical with an earlier described base of human plasma sphingomyelin. 10. 10. Ceramides and sphingomyelins were prepared from bovine kidney cortex, medulla and papilla. Their concentration decreased from the cortex to the papilla. 11. 11. The medium paraffin chain length of long-chain bases increased from the cortex to the papilla. 12. 12. The relative amounts of branched long-chain bases decreased from the cortex to the papilla. 13. 13. The relative amounts of trihydroxy bases were higher in the medulla than in the cortex or papilla.

Fatty Acid Composition in Ips calligraphus (Coleoptera: Scolytidae) during Postembryonic Development1,2

Gas-liquid chromotographic analyses using lipid extracts of Ips calligraphus (Germar) in its various developmental stages showed the presence of 8:0, 10:0, 12:0, 14:0, 16:0, 16:1, 18:0, 18:1, 18:2, 18:3, and 19:0 fatty acids, plus one unidentified compound. The rearing medium contained hark phloem of Pinus elliottii Engelmann var. elliottii and was qualitatively similar in fatty acid composition to beetle tissues. The major fatty acids in all developmental stages of I. calligraphus were 16- and 18-carbon acids, and 16:0 and 18:1 acids each comprised about 30–40% of the total. Both 16:0 and 18:1 acids decreased in each sex during adult maturation. Unsaturated acids together comprised about 50% of total in prepupae, 64% in mature virgin females, and 62% in stage-I (nonfeeding) larvae. The major unsaturated acid in adult beetles and stage-I larvae was 18:1. Percents of 18:2 and 18:3 acids were higher in adult virgin females than in adult males of the same age, a sexassociated difference that increased during adult maturation. Both 18:2 and 18:3 acids increased from the prepupal to 15-day-old adult stages, but the percent of 18:2 was highest (22%) and 18:3 lowest (trace) in stage-I larvae.

Lipids of Rhizopus arrhizus Fischer.

The lipids of Rhizopus arrhizus Fischer mycelia and sporangiospores were extracted, isolated, and separated by thin-layer, liquid, and gas chromatography. Structural confirmations of the compounds were made by a gas chromatographmass spectrometer combination. The n-heptane fraction contained squalene (1%) as a major hydrocarbon constituent. Other major lipid classes detected were free fatty acids, naturally occurring methyl esters of fatty acids, triglycerides, sterols, and polar lipids. The polar lipids (44.4%) were found in the highest concentrations, and the triglycerides (22.1%), sterols (16.7%), and free fatty acids (11.7%) were present in lesser concentrations. This is the first report of naturally occuring methyl esters of long-chain fatty acids being present in fungal mycelium. There appears to be a preference for incorporation of unsaturated acids into the complex lipids, with the exception of the triglycerides. The major saturated fatty acids in the mycelium were palmitic (C(16)) and arachidic (C(20)), whereas the major unsaturated acids were oleic (C(18:1)) and linoleic (C(18:2)), respectively.

The fatty acid composition of porcine spermatozoa phospholipids.

The fatty acid composition of three phospholipids of boar spermatozoa from 32 ejaculates was determined; choline phosphatide, ethanolamine phosphatide, and serine phosphatide were the phospholipids in which 19 fatty acids and two aldehydes were identified. Thin-layer and gas-liquid chromatography were employed for separation of phospholipids and determination of fatty acids. Major saturated fatty acids present were palmitic (16:0), stearic (18:0), and myristic (14:0). Palmitic and stearic acid were present in highest concentrations, ranging from 8 to 19% and 4 to 36%, respectively, in the three phosphatides. Unsaturated fatty acids predominated in the choline and ethanolamine phosphatides, while saturated acids predominated in the serine phosphatides. Docosapentaenoic acid (22:5ω6) was the major unsaturated acid at a high of 38.6%. Docosahexaenoic acid (22:6) was somewhat less at 25.2%. Oleic acid (18:1ω9), linoleic acid (18:2ω6), and arachidonic acid (20:4ω6) were present in lesser quantities.

The component fatty acids of some sea-weed fats

The component acids of the fats of the following marine algae have been investigated by gas-liquid chromatography:Rhodymenia palmata, Laurencia pinnatifida, Laminaria digitata, L. saccharina, Fucus vesiculosus, F. serratus, Pelvetia canaliculata, Ascophyllum nodosum. The principal saturated acids are palmitic and myristic acids, some contain ca. 2–5% of stearic acid; traces of C8 and C10 saturated acids are present, but C12 (and in all but one) C 20saturated acids are absent. The major unsaturated acids are octadecenoic and octadecadienoic acids (probably oleic and linoleic acids), but some species also contain appreciable amounts (up to 12%) of hexadecenoic acid. All the oils contain significant amounts of an eicosatetraenoic acid (probably arachidonic acid) and in some eicosatrienoic and/or eicosapentaenoic acids are also present in small quantities. Two acids of unknown constitution (possibly branched chain acids) are also present in minor amounts. No C22 unsaturated acids could be detected.INTRODUCTIONVery little is known about the component fatty acids of marine algae. Lovern (1936) examined the fatty acids from the fats of Fucus vesiculosus, Laminaria digitata and Rhodymenia palmata using lead salt crystallization and fractional distillation techniques (Table 2). With these methods, however, it was not possible to separate individual unsaturated acids having the same number of carbon atoms from one another. The mean unsaturation values of these fractions were therefore evaluated from their iodine values and expressed as the number of hydrogen atoms necessary to convert the fraction to the corresponding fully saturated state; thus ( — 4–0H) indicates an average unsaturation corresponding with two double bonds.