Roasting effects on fatty acid distribution of triacylglycerols and phospholipids in the kernels of pumpkin (Cucurbita spp) seeds

In this study, changes in fatty acid distributions of pumpkin seeds (Cucurbita spp) in the course of the roasting process were investigated. Whole pumpkin seeds were exposed to microwaves for 6, 12, 20 or 30 min at a frequency of 2450 MHz. The kernels were separated from the seeds, and the lipid components and the fatty acid distributions of triacylglycerols (TAGs) and phospholipids (PLs) were analysed by a combination of thin layer chromatography and gas chromatography. Major lipid components were TAGs, free fatty acids (FFAs) and PLs, while steryl esters and diacylglycerols were also present in minor proportions. The greatest PL losses (p < 0.05) were observed in phosphatidyl ethanolamine, followed by phosphatidyl choline or phosphatidyl inositol. With a few exceptions, significant differences (p < 0.05) in fatty acid distributions occurred when the seeds were microwaved for 20 min or more. Nevertheless, the positional characteristics of fatty acid distributions in the TAGs were still retained after 20 min of roasting: unsaturated fatty acids were predominantly concentrated in the sn‐2‐position, and saturated fatty acids primarly occupied the sn‐1‐ or sn‐3‐position. These results suggest that no significant changes in fatty acid distribution of TAGs and PLs would occur within 12 min of microwave roasting, thus ensuring that a good‐quality product would be obtained. Copyright © 2005 Society of Chemical Industry     

Mesocarp,seed and pollen lipids of Raphia palms

The lipid classes, fatty acids and sterols of the mesocarp, seed and pollen lipids of five species of Raphia palms endemic to Nigeria were analysed. Apart from quantitative differences in the fatty acid compositions, chromatographic analyses demonstrated very little change in the patterns of the characteristic lipids associated with either the mesocarps, seed endosperms or pollens. Mesocarp lipids contained mainly triglycerides, while palmitic, oleic and linoleic acids were the major acids. Contrary to published data for seed lipids, Raphia seed endosperms contained a relatively small amount of triglycerides and a high proportion of polar lipids. Fatty acids associated with this tissue were not only highly unsaturated, but were significantly different from typical fatty acids of seed lipids. Raphia pollens, on the other hand, showed a complex array of lipid types. Triglycerides, sterols and sterol esters constituted the main neutral lipids while phosphatidyl choline, phosphatidyl inositol, phosphatidyl ethanolamine and galactosyl diglycerides represented the polar fraction. Apart from minor trends, palmitic, oleic and linoleic acids constituted the major fatty acids in all species. The biological importance of the steroidal sapogenins found in all organs is discussed.     

虾头中磷脂提取与组学分析

研究虾头中磷脂的提取制备方法,并分别利用气相色谱法和多维度串联质谱法对样品磷脂的脂肪酸链结构进行脂质组学分析。利用乙醇浸提法制备得到虾头中的磷脂,并从乙醇体积分数、提取温度和提取时间3?个因素对提取方法进行优化,得到较优条件为乙醇体积分数90%、提取温度50?℃、提取时间30?min,磷脂的提取效果最佳,实际提取量可达到（11.58±0.03）mg/g,与优化前相比提高了83.8%。磷脂样品经甲酯化反应后用气相色谱法分析其脂肪酸链组成,并用高效液相色谱-质谱联用技术经负离子全扫描对磷脂分子实现分离鉴定和定量分析。结果显示,磷脂的脂肪酸链中主要含有棕榈酸链、亚油酸链、二十碳五烯酸和硬脂酸链等23?种脂肪酸链,其中单不饱和脂肪酸链占9.51%,多不饱和脂肪酸链占35.33%;磷脂样品中共检出磷脂酰胆碱、磷脂酰乙醇胺、磷脂酰肌醇和磷脂酰丝氨酸4?类共28?种磷脂分子,该提取方法所得各种类磷脂的脂肪酸链中存在许多不饱和度较高的脂肪酸链,如40∶8、36∶7、38∶7、O-40∶7、40∶7、34∶6、O-36∶6、36∶6、O-38∶6、38∶6、40∶6等。虾头中磷脂含量丰富,其脂肪酸链不饱和度较高,因此具有较高的开发利用价值。     

Phospholipids of marine origin. I. The hake (Merlucius capensis, Castelnau)

The composition of hake flesh and hake liver phospholipids was determined by an hydrolytic procedure and by chromatography on silicic acid. The hydrolytic procedure involved determination of lecithin-choline, sphingornyelin-choline, lyso lecithin-choline, ethanolamine, serine, myo-inositol and the average equivalent weight of the liberated fatty acids. The composition of the flesh and liver phospholipids was very similar, the latter contained more sphingomyelins and cardiolipins at the expense of phosphatidyl choline. Phospholipid fatty acids had a markedly higher equivalent weight and unsaturation than the corresponding non-phosphorylated lipid fatty acids. The cephalin fractions contained more long chain polyunsaturated fatty acids, more stearic acid and less palmitic acid than the phosphatidyl choline fractions. Sphingomyelins were particularly rich in lignoceric and nervonic acid.     

Lipid content and fatty acid composition of green algae Scenedesmus obliquus grown in a constant cell density apparatus

The lipids of alga Scenedesmus obliquus grown under controlled conditions were separated and fractionated by column and thin-layer chromatography, and fatty acid composition of each lipid component was studied by gas-liquid chromatography (GLC). Total lipids were 11.17%, and neutral lipid, glycolipid and phospholipid fractions were 7.24%, 2.45% and 1.48% on a dry weight basis, respectively. The major neutral lipids were diglycerides, triglycerides, free sterols, hydrocarbons and sterol esters. The glycolipids were: monogalactosyl diglyceride, digalactosyl diglyceride, esterified sterol glycoside, and sterol glycoside. The phospholipids included: phosphatidyl choline, phosphatidyl glycerol and phosphatidyl ethanolamine. Fourteen fatty acids were identified in the four lipid fractions by GLC. The main fatty acids were C18:2, C16:0, C18:3(alpha), C18:1, C16:3, C16:1, and C16:4. Total unsaturated fatty acid and essential fatty acid compositions of the total algal lipids were 80% and 38%, respectively.     

Fumgal lipids. I. Effect of different nitrogen sources on the chemical composition

The effect of three nitrogen sources on the chemical composition of seven fungi, namely: Aspergillus niger, A. luchuensis, Penicillium crustosum, Alternaria tenuis, Rhizoctonia solani, Mucor sp. and Pythium irregulare has been studied. The various fungi showed a great variation with respect to lipid percentage and total lipid content. Lipid content varied from 3.2 to 41.5%. Non-polar lipids were comprised of monoglycerides, diglycerides, free sterols, free fatty acids and triglycerides. The quantitative make-up of the non-polar lipid varied with different nitrogen sources. Palmitic, stearic, oleic and linoleic acids were the major fatty acids while lauric, myristic, palmitoleic, linoleic and arachidic were the minor ones. The fatty acid composition was dramatically changed by changing the nitrogen source. Since different fungi responded differently to changes in nitrogen source, no generalisation could be made. Two-dimensional thin-layer chromatography of the polar lipid fraction of these fungi revealed the presence of a maximum of fifteen spots. Phosphatidyl choline, phosphatidyl ethanolamine and phosphatidyl inositol were the major spots while lysophosphatidyl choline, lysophosphatidyl ethanolamine and phosphatidyl glycerol were present in smaller quantities. In comparison to phospholipids, glycolipids (except sterol glycoside) were present in relatively lower concentration. Pythium irregulare was very characteristic in having no glycolipids at all.     

Role of seed phosphatides as antioxidants for ghee (butter fat)

Antioxidant potentiality of seed phospholipids for stored ghee was found to be in the order of sunflower (Helianthus annuus L.), groundnut (Arachis hypogea), soybean (Glycine max) and cotton seed (Gossypium sp.), possibly corresponding to their phosphatidyl ethanolamine content. Out of phosphatidyl choline, phosphatidyl ethanolamine and phosphatidic acid, phosphatidyl ethanolamine was found to be the most effective antioxidant. Antioxidant property of phosphatidyl ethanolamine did not vary with the seed source, indicating that the fatty acid portion of the molecule played no role in protecting ghee against oxidation. In stored ghee addition of phosphatidyl ethanolamine and phosphatidyl choline reduced lipolysis, probably by interacting with the lipase system. During storage, phosphatidyl ethanolamine afforded better protection against the oxidation of unsaturated fatty acids.     

INHIBITION OF ASPERGILLUS GROWTH AND EXTRACELLULAR AFLATOXIN ACCUMULATION BY SORBIC ACID AND DERIVATIVES OF FATTY ACIDS

A study was conducted to determine the effects of sorbic acid and several derivatives of fatty acids (amides, aminimides, and monoglycerides) upon toxigenic cultures of Aspergillus flavus and A. parasiticus. A synthetic medium was inoculated with spores, incubated for 48 h at 27°C, and then supplemented with sorbic acid and fatty acid derivatives. Cultures were then incubated for an additional 5 days. Aflatoxins were extracted, separated, and quantitated. Mycelial mats were dried, weighed, and analyzed for lipid and mineral content. Cerulenin (8 μg/ml) was the most effective fatty acid derivative examined, reducing mycelial growth by 37% and completely inhibiting extracellular accumulation of aflatoxins. Other derivatives, in decreasing order of effectiveness, included M-20 (an aminimide), lauribic, and lauricidin. Mycelia grown in the presence of fatty acid derivatives contained less phosphorus, potassium, magnesium, phosphatidyl ethanolamine, phosphatidyl serine, cholesterol, and triglycerides, but more cardiolipin, phosphatidyl choline, free fatty acids, fatty acid esters, and diglycerides. Levels of monoglycerides and cholesterol esters remained essentially unchanged. Inhibition by sorbic acid was nonspecific, affecting both mycelial growth and extracellular aflatoxin accumulation to approximately the same extent. Utilization of fatty acid derivatives for determining mechanisms of aflatoxin accumulation and lipid biosynthesis appears promising.     

Lipid Content and Fatty Acid Composition in Bamboo Shoots

Lipids from bamboo shoots (Phyllostachys pubescens), peeled and divided from top to base, were extracted and fractionated into three classes, and each class separated into constituent components by thin-layer chromatography (TLC). Fatty acid composition and amount of separated lipids were determined. Total lipids (TL) ranged from 800 (top) to 380 mg (base) per 100g fresh weight and the ratio of nonpolar lipids (NPL):glycolipids (GL):phospholipids (PL) was about 17:27:56. The main fatty acids of the three lipid classes were palmitic, linoleic and linolenic acids, but composition was remarkably different among these fractions. The fatty acid composition of triglycerides (TG) was similar to the original NPL. Palmitic acid was almost all located in 1-, 3-position, linoleic acid mainly located in 2-position of TG, while linolenic acid was distributed in each position. Digalactosyl diglyceride (DGDG) and monogalactosyl diglyceride (MGDG) were the main components of GL; the average of the former had about 37% linoleic and 29% linolenic acids, while the latter had about 25% linoleic and 62% linolenic acids. Bamboo shoots contained 9 PL fractions, the major being phosphatidyl choline (PC) and phosphatidyl ethanolamine (PE). PC contained about 48% linoleic, 31% palmitic and 11% linolenic acids, and PE also had the similar tendency as PC.     

The structures of adipose tissue and heart muscle triglycerides in the domestic chicken (Gallus gallus)

Chicken (Gallus gallus) perineal, subcutaneous (leg), perinephric and pericardial adipose tissue and heart muscle triglycerides were subjected to stereospecific analysis. All were found to be asymmetric with a preponderance of saturated fatty acids in position 1 and a preponderance of unsaturated fatty acids in position 2. Position 1, for example, contained 48–55% saturated acids while position 2 contained 17–22% and position 3, 33–41%. Stereospecific analysis of fractions of the perineal triglycerides separated by argentation chromatography indicated that the proportions of the individual molecular species could be calculated assuming that there was 1-random, 2-random, 3-random arrangement of fatty acids in the triglycerides.     

Composition of wheat-flour lipids

Lipids were extracted from a single sample of wheat flour using three solvent systems: ethanol–diethyl ether–water (2:2:1 by vol.); chloroform–methanol (2:1 by vol.); and water-saturated n-butanol. Analysis of the extracts and of residual lipid in the extracted flour showed that water-saturated n-butanol was the most efficient solvent. Wheat-flour lipids were extracted with water-saturated n-butanol and separated by chromatographic procedures into individual components. The lipid classes which were isolated and studied were steryl ester, free sterol, 6-O-acyl steryl glucoside, steryl glucoside, triglyceride, diglyceride, monoglyceride, free fatty acid, monogalactosyl diglyceride, 6-O-acyl monogalactosyl diglyceride, digalactosyl diglyceride, digalactosyl monoglyceride, monoglycosyl ceramide, diglycosyl ceramide, N-acyl phosphatidyl ethanolamine, N-acyl lysophosphatidyl ethanolamine, phosphatidyl ethanolamine, lysophosphatidyl ethanolamine, phosphatidyl choline, lysophosphatidyl choline, phosphatidyl serine and phosphatidyl inositol. Monogalactosyl monoglyceride was also tentatively identified. The quantitative distributions of the lipid classes were determined. Monoglycosyl ceramide contained small amounts of normal fatty acids (12:0–24:0) and large amounts of 2-hydroxy fatty acids (principally 16:0 and 20:0), with similar amounts of dihydroxy long-chain bases (18:0 and 18:1) and trihydroxy long-chain bases (18:0, 18:1, 19:0, 19:1, 20:0, 22:0). The principal sterols were identified as β-sitosterol, campesterol, and C₂₈ and C₂₉ saturated sterols. The fatty acids in the sterol lipids were principally 16:0 (50–60%) and 18:2 (28–30%) with small amounts of 16:1, 18:0, 18:1 and 18:3. The fatty acids in all the glycerides were principally 18:2 (51–84%) with lesser amounts of 16:0, 18:0, 18:1 and 18:3.     

Phospholipids of marine origin. IV. The abalone (Haliotis midae)

Phospholipids of the abalone were separated into component fractions by chromatography on silicic acid. The phospholipids were remarkable for the presence (6%) of an unusual sphingolipid liberating 2-amino-ethylphosphonic acid on hydrolysis, and for the high proportion of plasmalogens (23%). The presence of phosphatidyl ethanolamine plus ethanolamine plasmalogen (32%), phosphatidyl serine (5%), phosphatidyl inositol (5%), phosphatidyl choline (41%) and sphingomyelin (1%) were also demonstrated. The fatty acid distribhion in the phospholipids, the non-phosphorylated lipids and the unusual sphingolipid was determined by gas chromatography. In general these results show a similarity between the phospholipid and the non-phosphorylated lipid fatty acids, the former being richer in long chain polyunsaturated fatty acids. Fatty acids of the unusual sphingolipid were outstanding for the high palmitic (53%) and stearic acid (15%) content.     

The composition of the fatty acids and aldehydes of the ethanolamine and choline phospholipids of various meats

The ethanolamine phospholipids of beef, lamb, pork and chicken examined in this study contained over 40% of ethanolamine plasmalogen, whereas fish contained only 13%. The level of choline plasmalogen in choline phospholipids was less than 1% in fish and ranged from 10 to 30% in the other four meats. Palmitaldehyde was the major fatty aldehyde in the choline plasmalogens of beef, lamb, pork and chicken (65–80% of total aldehydes), but was present at lower levels in the ethanolamine plasmalogens. The per cent fatty acid compositions of phosphatidylethanolamine and the corresponding ethanolamine plasmalogen were very similar, being typically low in palmitic acid but very high (56–74%) in polyunsaturated fatty acids. The fatty acids of the choline plasmalogens contained more polyunsaturated fatty acids than the corresponding phosphatidyl cholines, but at lower levels than in the fatty acids of the ethanolamine phospholipids.     

CHEMICAL CHARACTERIZATION AND STEREOSPECIFIC ANALYSIS OF LIPIDS SYNTHESIZED BY CERTAIN YEAST STRAINS

Fatty acid analysis of lipids from yeast strains, Apiotrichum curvatum ATCC 10567, Cryptococcus albidus ATCC 56297, Lipomyces starkeyi ATCC 12659, and Rhodosporidium toruloides ATCC 10788, grown on whey permeate revealed palmitic, stearic, oleic and linoleic acids as the predominant fatty acids in the triacylglycerol fractions. The phospholipid fractions were dominated by oleic and linoleic acids. The stereospecific distribution of fatty acids in the triacylglycerol fractions of lipids from two yeast strains, Apiotrichum curvatum ATCC 10567 and Lipomyces starkeyi ATCC 12659, was determined and revealed the presence of almost entirely unsaturated fatty acids at the sn-2 position (91.9% and 82.8%, respectively). The dominance of unsaturated fatty acids (in the range of 61.5 to 72.3%) at the sn-1 position was also observed. Oleic acid was the predominant fatty acid at positions sn-1 and sn-2 for both yeast strains. Position sn-3 had the greatest concentrations of saturated fatty acids, with palmitic acid as the predominant fatty acid.     

Changes in the composition of the fatty acids and aldehydes of meat lipids after heating

The effects of heating at 132°C on the fatty acids and fatty aldehydes of neutral lipids and phospholipids of lean beef, veal, lamb, pork and chicken were studied. Heating caused hydrolysis of the plasmalogens in the phospholipids, and varying amounts of the liberated fatty aldehydes were recovered in the neutral lipid fractions. Beef phosphatidyl choline lost more polyunsaturated fatty acids than that of the other meats. Beef and veal phosphatidyl ethanolamine lost more polyunsaturated fatty acid than that of lamb, pork or chicken, but the effect was obscured by the influx of fatty acids from elsewhere into this fraction after heating.     

EFFECT OF POSTMORTEM AGING ON CHICKEN MUSCLE LIPIDS

Neutral lipids of fresh chicken breast muscles are shown to be triglycerides, sterols and sterol esters with only traces of mono- and diglycerides and free fatty acids. Phospholipids include measurable quantities of phosphatidyl choline, phosphatidyl ethanolamine, phosphatidyl inositol, phosphatidyl serine, sphingomyelin, diphosphatidyl glycerol, lysophosphatidyl choline and lysophosphatidyl ethanolamine. Fatty acid analyses of several of the lipid fractions are also included. Decreases in phosphatidyl choline and phosphatidyl ethanolamine coupled with increases in lysophosphatidyl choline, lysophosphatidyl ethanolamine and free fatty acids after 48 hr postmortem in the cold indicate phospholipase A activity concurrent with other postmortem changes. The significance of the results is discussed.     

Lipid composition of five species of Indian prawns

The lipid and fatty acid compositions of five Indian species of prawns, Metapenaeus monoceros, M. dobsoni, M. affinis, Penaeus indicus and Parapenaeopsis stylifera, were examined. Phospholipids constituted 50–70% of the total lipids, with phosphatidyl choline (50%) and phosphatidyl ethanolamine (29%) as their chief components. Unsaponifiable matter comprised 21–40%, chiefly cholesterol: triglycerides only constituted 9–14.5%. In the total lipids (I.V. 90–112), saturated, monoenoic and polyenoic fatty acids averaged 42, 24 and 34%. Palmitic acid is high, oleic low, and 20:5 generally, but not always, higher than 22:6. The only brackish water prawn, M. monoceros, though generally in conformity, was distinctive in several respects.     

Identification and quantitative determination of the lipids of dried Origanum dictamnus leaves

The Origanum dictamnus plant was examined for its lipid and fatty acid compositions. A combination of chromatographic techniques has been employed for the qualitative and quantitative determination of the lipids of dried leaves of O. dictamnus. The following polar lipids were identified: mono-, di- and poly-digalactosyl diglycerides, sulpholipids, cerebrosides, phosphatidyl-ethanolamine, phosphatidylserine, phosphatidylglycerol, phosphatidylinositol, phosphatidyl choline and phosphatidic acid. The non-polar lipids identified were sterols, steryl esters, fatty alcohols, free fatty acid, waxes, traces of triglyceride, triterpenic acids and essential oil. The predominant fatty acids were palmitic, oleic and linoleic acids.     

Changes in lipid components during the development of the french bean seed (Phaseolus vulgaris)

Changes in lipid classes, fatty acid composition and distribution have been monitored during the germination, development and maturation of the French bean seed Phaseolus vulgaris. A lipase activity profile over time was also determined. Ungerminated seeds contained high levels of triglycerides and free fatty acids, but low levels of polar lipids, monoglycerides, and diglycerides. Five days after germination there was a decrease in the quantity of triglycerides and free fatty acids and a concomitant increase in the levels of monoglycerides, diglycerides, and polar lipids. As development and maturation progressed, triglycerides increased substantially at the expense of mono- and diglycerides. Ungerminated seeds contained high levels of C₂₀-C₂₂ fatty acids which decreased after germination with a concomitant increase in C₁₆-C₁₈ unsaturated fatty acids. A study of the fatty acid distribution among the different classes of lipids demonstrated that 55% of the unsaturated fatty acids in the ungerminated seeds were present in the triglycerides, whereas the remainder were distributed among the mono- and diglycerides as well the other lipid classes (free fatty acids, polar lipid, and sterols). Five days after germination, the majority of these unsaturated fatty acids were found in the glyceride form. Overall the lipid classes, fatty acid composition and distribution changes during development and maturation of the French bean seed indicated that it shares many of the characteristics of soya bean development.     

Changes in the composition of the rumen and abomasum lipids of sheep from birth to maturity

The composition of the lipids of the rumen and abomasum tissues of foetal (at term), 1 month, 2 month and 1-2-year old sheep grazed on pasture has been determined. The lipid content of the rumen tissues increased from 2.0% at birth to 3.4% in 1-2-year old sheep While that of the abomasum tissues increased from 2.6 to 5.7%. The main change in the neutral lipid fraction was a decrease in the hydrocarbon content from 0.13 % in the rumen tissues and 0.08 % in the abomasum tissues at birth to 0.003% and 0.006% respectively in the 1-2-year old sheep. The main components of the phospholipid fraction of the rumen and abomasum tissues were 34.9- 46.8% phosphatidyl choline; 14.623.5 % phosphatidyl ethanolamine; 14.3-21.1 % sphingomyelin; with smaller amounts of lysophosphatidyl choline (4 13-12.6 %), acidic phospholipids (cardiolipin) (4.1-8 -5 %) and phosphatidyl inositol/phosphaticlyl serine (3.0-5.5 %). No marked changes in phos- pholipid composition with age were noted. The amounts of phosphatidyl choline and phosphatidyl ethanolamine tended to be higher in the abomasum than in the rumen whereas the sphingomyelin content of the rumen tissue phospholipids was generally greater than that of the abomasurn tissue phospholipids. From the fatty acid composition of the triglycerides of the rumen and abomasum tissues it appeared that the foetal triglycerides were largely, though not entirely, of endogenous origin. In contrast the phospholipids of the foetal rumen and abomasum tissues contained di- and poly-unsaturated as well as branched-chain fatty acids in proportions similar to those found in older animals having access to pasture. From these results it is suggested that the phospholipids of the foetus are derived to a considerable extent from the maternal phospholipids.