Supercritical fluid extraction and characterization of lipids from algae Scenedesmus obliquus

Supercritical carbon dioxide (SC-CO2) extractions (with and without ethanol as an entrainer) were carried out to remove lipids and pigments from protein concentrate of green algae (Scenedesmus obliquus) cultivated under controlled conditions. The content and fatty acid composition of algal lipids using column, thin-layer (TLC) and gas-liquid chromatography (GLC) were determined. Absorption spectra of extracted fractions showed the predominance of chlorophyll A (lambda max at 410 nm). Single step supercritical carbon dioxide (SC-CO2) extraction resulted mostly in removal of neutral lipids and a part of glycolipids, but phospholipids were not extracted. Addition of ethanol to SC-CO2 increased the amount of glycolipids and phospholipids in the extract. TLC pattern of algal lipids showed that the main part of neutral lipids consisted of diglycerides, triglycerides, hydrocarbons, free sterols, and sterol esters. The glycolipids were mostly monogalactosyl diglyceride, digalactosyl diglyceride, esterified sterol glycoside, and sterol glycoside. In phospholipids, phosphatidyl choline, phosphatidyl glycerol, and phosphatidyl ethanolamine were the main compounds. Fatty acid composition patterns indicated the main fatty acids to be 16:0, 16:1, 16:2, 16:3, 16:4, 18:1, 18:2, and 18:3(a). Relatively high recovery of polyunsaturated fatty acids and essential fatty acids in supercritical fluid extracted algal lipids and proteins isolates were observed.     

Supercritical fluid extraction and characterization of lipids from algae scenedesmus obliquus

Supercritical carbon dioxide (SC‐CO₂) extractions (with and without ethanol as an entrainer) were carried out to remove lipids and pigments from protein concentrate of green algae (Scenedesmus obliquus) cultivated under controlled conditions. The content and fatty acid composition of algal lipids using column, thin‐layer (TLC) and gas‐liquid chromatography (GLC) were determined. Absorption spectra of extracted fractions showed the predominance of chlorophyll A (λ_max at 410nm). Single step supercritical carbon dioxide (SC‐CO₂) extraction resulted mostly in removal of neutral lipids and a part of glycolipids, but phospholipids were not extracted. Addition of ethanol to SC‐CO₂ increased the amount of glycolipids and phospholipids in the extract. TLC pattern of algal lipids showed that the main part of neutral lipids consisted of diglycerides, triglycerides, hydrocarbons, free sterols, and sterol esters. The glycolipids were mostly monogalactosyl diglyceride, digalactosyl diglyceride, esterified sterol glycoside, and sterol glycoside. In phospholipids, phosphatidyl choline, phosphatidyl glycerol, and phosphatidyl ethanolamine were the main compounds. Fatty acid composition patterns indicated the main fatty acids to be 16:0, 16:1, 16:2, 16:3, 16:4, 18:1, 18:2 and 18:3(a). Relatively high recovery of polyunsaturated fatty acids and essential fatty acids in supercritical fluid extracted algal lipids and protein isolates were observed.     

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.     

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.     

Lipid Composition of Field Pea (Pisum sativum cv Trapper) Seed and Starch

The total lipids in field pea seeds and refined starch were extracted by five aqueous/organic solvent systems and the greatest yield of total. neutral and polar lipids was obtained with hot n-propanol-water (3:1 v/v). Lipids extracted from field pea seeds represented 2.9% of the seed weight and consisted of 43.2% neutral lipids, 3.2% glycolipids and 53.6% phospholipids. The major components of the three fractions were 70% triacylglycerol in neutral lipid, 28% esterified sterol glycoside in glycolipid and 55% phosphatidylcholine in phospholipid. The purified starch fraction contained 0.22% surface lipids and 0.09% internal lipids. The surface lipids were primarily sterol esters and free fatty acids while only free fatty acids were found in the internal lipids. The ability of lysophospholipids and fatty acids to complex with field pea starch was demonstrated by differential scanning calorimetry and X-ray diffraction, respectively.     

鲤、鲫卵的脂质和脂肪酸特性

鲤(Cyprinus carpio)、鲫(Carassius auratus)卵总脂分别为干基的16.90%和10.19%。两者脂质和脂肪酸组成总体比较接近。总脂中含较高的甘油三酯和极性脂,并含一定量的固醇及其酯。极性脂约占总脂的30%,主要为PC和PE,并含一定的心磷脂。两种鱼卵主要含C14～C22的19种脂肪酸,16:0和18:1含量最高,DHA等n-3族多烯酸和20:4n-6也较高,而EPA较低,P/S>>0.5。总脂中饱和、单不饱和、多不饱和脂肪酸的比例接近1:1:1,中性脂中C18、C20酸较多,极性脂中C22酸(DHA)较多。鲫卵18:2n-6较高,使得多烯酸含量稍高,胆固醇、磷脂含量及PC/PE和n-3/n-6稍低于鲤卵。研究表明:两种淡水鱼卵与其鱼肉相比,磷脂和胆固醇明显高,磷脂以PC为主,其次为PE;多烯酸稍高,其中DHA高而EPA低,并含20:4n-6。鲫卵PL的乳化稳定性低于相同浓度大豆磷脂的。其独特的脂质具有较大的研究利用价值。     

Changes in lipid composition and fatty acid profile of Nham,a Thai fermented pork sausage,during fermentation

Changes in lipid composition and fatty acid profile of Nham during fermentation were investigated. Total lipids of Nham were in the range 2–3%. The extracted lipid of initial Nham mix consisted mainly of triglycerides (TG), accounting for more than 75% of the total lipid, followed by phospholipids (PL) and a trace amount of diglycerides (DG) and free fatty acid (FFA). During fermentation, TG, DG and PL decreased with a concomitant increase in FFA, indicating lipolysis of Nham lipids during fermentation. Changes in fatty acids of the total lipids, non-polar and polar lipid fractions were observed during fermentation. In both total and non-polar lipid fractions, the major fatty acids found in a descending order were oleic (C18:1), linoleic (C18:2) and palmitic (C16:0) acids, which together accounted for 90% of the total fatty acids. Increases in fatty acid contents in both total and non-polar lipid fractions, were observed with a corresponding decrease in the quantity of fatty acids of phospholipids. As the fermentation proceeded, peroxide value generally increased while TBARS values decreased. Overall, lipid oxidation in Nham occurred during fermentation but did not cause the objectionable odour and taste in any Nham tested.     

Characterization of phospholipid composition of black cumin (Nigella sativa L.) seed oil

Black cumin (Nigella sativa L.) seed oil was extracted with two different solvents, n-hexane (H) and a mixture of chloroform/methanol (CM) (2:1, by volume). Amount of total lipid (TL) was higher in the CM miscelle (39.2% of seed fresh weight) than in the H extract (37.9%). Chemical characteristics as well as fatty acid profile of the TL extracts were compared and the analysis revealed that the major fatty acid was linoleic acid C18:2n-6 (ca. 57% of total fatty acid methyl esters (FAME)) followed by oleic acid C18:1n-9. Palmitic acid C16:0 was the major saturated fatty acid and detected in appreciable level. Chromatography on a silica column with solvent of increasing polarity yielded 96.1-97.2% neutral lipids (NL) and ca. 3% of polar lipids. Gas liquid chromatography with flame ionization detector (GLC/FID) showed that the major fatty acid present in all lipid classes was C18:2n-6 followed by C18:1n-9 and C16:0 acids, respectively. Phospholipid (PL) classes were separated via normal-phase HPLC. Separation was achieved on a silica column by gradient elution from isooctane/2-propanol (6:8, by volume) to isooctane/2-propanol/water (6:8:0.6, by volume) lasting 35 min with UV detection at 205 nm. The major individual PL classes were found to be phosphatidylcholine (PC; ca. 46-48% of total PL) followed by phosphatidylethanolamine (PE), phosphatidylserine (PS) and phosphatidylinositol (PI), respectively. Phosphatidylglycerol (PG), lysophosphatidylethanolamine (LPE) and lysophosphatidylcholine (LPC) were isolated in smaller quantities. The level of saturated fatty acids, namely palmitic C16:0 and stearic C18:0 acids, was considerably higher in PL classes than in the corresponding triacylglycerols. Characterization of PL profile from Nigella sativa L. seed oil as well as the development of new source of PL was the primary aim of this study.     

Changes in fatty acids of frog legs during frozen storage

The changes in the fatty acids of frog leg meat during frozen storage were studied with column and gas-liquid chromatography. The major component of the lipids, the phospholipids constituted 90% of total lipids. 16:0, 18:0, 22:0 and 18:2 polyunsaturated fatty acid were the major fatty acids of the frog legs meat lipids. Short chain fatty acids were noticed to the extent of 10%. During frozen storage the proportion of phospholipids decreased, while that of neutral lipids increased. Since the total lipid content was constant, phospholipases were presumably responsible for this change. Alterations in the fatty acid composition of the neutral lipids during storage were consistent with such a hypothesis.     

热风干制前后凡纳滨对虾中脂质及其脂肪酸组成变化

为了研究凡纳滨对虾在热风干制前后脂质及其脂肪酸组成变化,通过硅胶柱层析法分离对虾脂质中的各个组分,采用气相色谱-质谱联用分析总脂、甘油三酯、脑磷脂与卵磷脂中脂肪酸组成在干制前后的变化.结果表明:干制后对虾总脂含量发生极显著下降(P<0.01),由6.46 g/100 g(以干基计)下降至4.28 g/100 g,甘油三...     

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.     

Phospholipids of marine origin. The lantern fish (Lampanyctodes hectoris)

Lantern fish of the species Lampanyctodes hectoris were shown to contain phospholipids (10 g kg^?1) and non-phosphorylated lipids (140 g kg^?1). The phospholipid fraction consisted of phosphatidyl choline (47% of total phospholipids), phosphatidyl ethanolamine (42%), phosphatidyl serine (3%), phosphatidyl inositol (1%), sphingomyelin (4%), lyso-phosphatidyl choline (1%) and cardiolipins (2%). Lantern fish (L hectoris) meals normally contain unacceptably high lipid contents (150 g kg^?1 and over); this characteristic was found not to be due to a high phospholipid level in the lantern fish. The major fatty acid of the phospholipids was C22:6n-3 (25% total fatty acids) followed by C16:0 (18%), C18:ln-9 (16%) and C20:5n-3 (8%). This distribution was different from that of the non-phosphorylated lipids where the major fatty acid was C16:0 (21%) followed by C18:ln-9 (19%), C20:5n-3 (11%), C20:l (7%) and C22:6n-3 (7%). The lantern fish press oil and residual meal lipids had fatty acid distributions similar to those of the non-phosphorylated lipids.     

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.     

Characterization of Shrimp Lipids

Edible shrimp (Penaeus aztecus) tissue contains approximately 1.2% extractable lipids, the majority of which are phospholipids. Data from the gravimetric quantitation of lipid classes isolated by column chromatography indicated that phosphatidyl choline was the predominant phospholipid and cholesterol the predominant neutral lipid in edible shrimp tissue. Fatty acid distribution data indicated that sphingomyelins contained the greatest percent by weight of unsaturated fatty acids while cholesterol esters contained the greatest proportion of saturated fatty acids. Enzymatic hydrolysis followed by gas liquid chromatography of phosphatidyl choline, phosphatidyl ethanolamine, and phosphatidyl serine indicated that fatty acids located at the β position were more highly unsaturated than those at the α position.     

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.     

Fatty acid composition of bovine teat canal keratin

Keratin from 507 excised teats was pooled, separated into three samples, and analyzed for fatty acid composition of extracellular and intracellular lipids. Mean weight of keratin collected per teat canal was 8.97 mg. Extracellular lipids were recovered in petroleum ether. Intracellular lipids were extracted in chloroform: methanol (2:1, vol/vol) solution. Average keratin wet weight of extracellular and intracellular lipid fractions were 37.1 and 21.9 mg/g, respectively. Polar and nonpolar lipids were present in both fractions. Predominant fatty acids in extracellular and intracellular lipids were C16, C18:1, and C18. Extracellular lipids contained greater concentrations of C4 to C18:1 fatty acids than did intracellular lipids. Percent of total fatty acid weight comprised by each of C4, C10, C12 and C14 was also significantly greater in extracellular than intracellular fractions. Intracellular lipids contained a greater concentration and percent total fatty acid content comprised by C18:2 than extracellular lipids. Data suggest lipids accessible at the keratin interface are in part of milk fat origin.     

Lipids in cereals. 1. Pennisetum typhoideum

Two improved strains of Pennisetum typhoideum (‘bajra’) were found to have a free lipid content of about 5.0% and bound lipid content of about 0.5%. In the non-polar fraction, sterol esters and hydrocarbons, triglycerides, free fatty acids, free sterols and partial glycerides were present with triglycerides as the principal constituents. Polar lipids were separated by two-dimensional thin-layer chromatography and lecithin was found to be the major component. Sterol-containing glycolipids (sterol glycosides and esterified sterol glycosides) were present in appreciable amounts. Phosphatidyl ethanolamine, phosphatidyl glycerol, phosphatidyl inositol, lysophosphatidyl ethanolamine, lysolecithin, phosphatidic acid, poly-glycerophosphatide, mono- and di-galactosyl glycerides and cerebrosides have also been tentatively identified.     

超高效液相色谱-静电场轨道阱高分辨质谱鉴定核桃仁的脂质构成

利用超高效液相色谱-静电场轨道阱高分辨质谱系统鉴定了核桃的脂质组.在正负离子模式下获得脂质的一级质谱和二级质谱信息后,共鉴定出4大类525种脂质分子,包括250种甘油酯、221种磷脂、18种糖脂、36种鞘脂类,含量分别占总脂质的87％、12.97％、0.02％和0.01％.甘油二酯(diacylglycerol,DG)...     

Changes in milk fat phospholipids during lactation

Changes in lipid composition were studied in milk obtained on postpartum d 3 (colostrum), 7, 42, and 180 from 12 Holstein cows. Triglycerides, 96 to 97% of total lipids, were relatively constant during lactation. Phospholipids and cholesterol declined with advancing lactation. Concentrations of the fatty acids synthesized within the mammary gland, C10:0 to C16:0, increased about 50% from 7 to 42 d of lactation. During this period, compensatory decreases were observed in C18:1. The phospholipids were separated into five major classes: sphingomyelin, phosphatidyl choline, serine, inositol, and ethanolamine for fatty acid analysis. The changes that occurred in milk total fatty acids were reflected in phosphatidyl phospholipid fatty acid composition: an increase in medium-chain fatty acids and a decrease in polyunsaturated fatty acids of 18, 20, and 22 carbon atom chain length as lactation progressed. These changes are consistent with the theory that milk phospholipids are synthesized de novo entirely in the mammary gland.     

Seasonal changes in phospholipids of mussel (Mytilus edulis Linne)

The phospholipids of mussels (Mytilus edulis Linne) from the coast of Qingdao were extracted, fractionated and analysed over a 12 month period. The contents of total lipids, neutral lipids, polar lipids and phospholipids were measured. The composition of phospholipids was determined by high‐performance liquid chromatography, and their fatty acid composition was analysed by gas chromatography. The phospholipid content ranged from 3.6 to 6.4 g kg^?1 soft tissue. PE (phosphatidyl ethanolamine) and PC (phosphatidyl choline) were the major constituents. C16:0, C20:5 and C22:6 were the major fatty acids. C20:5 (5.25–23.10%) and C22:6 (6.05–20.42%) varied regularly with the seasonal factors. Their total amounts were high from January to June, which would be an optimal time for the utilisation of the phospholipids of mussels. © 2002 Society of Chemical Industry