Liposomal formulations from phospholipids of Greek almond oil. Properties and biological activity

The seeds of the almond tree [(Prunus dulcis (Mill.) D. A. Webb. (syn. Prunus amygdalus)] were collected in two different periods of maturity and were studied for their lipid content. The total lipids (TL) were extracted by the Bligh-Dyer method and the lipid classes have been isolated by chromatographic techniques and were analyzed by HPTLC coupled with a flame ionization detector (HPTLC/FID) and GC-MS. The oils were found to be rich in neutral lipids (89.9% and 96.3% of total lipids) and low in polar lipids (10.1% and 3.7% of total lipids) for the immature and mature seed oils, respectively. The neutral lipid fraction consisted mainly of triacylglycerides whereas the polar lipids mainly consisted of phospholipids. GC-MS data showed that the main fatty acid for both oils was 9-octadecenoic acid (oleic acid). The unsaturated fatty acids were found as high as 89.4% and 89.7%, while the percentage of the saturated fatty acids was found 10.6% and 10.3% for the immature and mature seed oils, respectively. Liposomes were prepared from the isolated phospholipids using the thin lipid film methodology, and their physical properties were characterized. Cytotoxicity was found absent when assayed against normal and cancerous cell lines. These new formulations may have future applications for encapsulation and delivery of drugs and cosmetically active ingredients.     

超临界CO_2萃取韭菜籽油成分的GC-MS分析

以索氏提取法为对照,采用超临界二氧化碳(SC-CO_2)萃取韭菜籽油,气相色谱-质谱联用技术(GC-MS)对韭菜籽油成分进行分析,NIST 02质谱数据库对其进行分析和鉴定.结果表明,SC-CO_2萃取压力为22.25 MPa、温度为40.40℃条件下萃取86.7 min时,萃取得率为17.52%,共分离鉴定出17种物质,其中,饱和脂肪酸以棕榈酸(6.25%)为主,占脂肪酸总量的 9.05%;不饱和脂肪酸主要是亚油酸(69.71%)和油酸(19.53%),占脂肪酸总量的90.50%.采用索氏提取得率为16.50%,共鉴定出10种物质,饱和脂肪酸以棕榈酸(7.22%)为主,占总脂肪酸量的9.84%;不饱和脂肪酸主要是亚油酸(69.34%)和油酸(20.12%),不饱和脂肪酸占脂肪酸总量的90.16%.另外SC-CO_2萃取韭菜籽油还检出单不饱和脂肪酸7-棕榈烯酸、角鲨烯和β-谷甾醇.     

Fatty acid compositions of seed oils of Haematostaphis barteri and Ximenia americana

The fatty acid compositions of the seed oils of Haematostaphis barteri (blood plum) and Ximenia americana (Wild olive) plants were determined by the Gas Chromatography Mass Spectroscopy (GC-MS) technique. H. barteri contained six fatty acids with oleic (69.35%) and stearic (15.40%) the most abundant unsaturated and saturated fatty acids, respectively. Unsaturated higher fatty acids, namely Eicosadienoic (6.92%) and Erucic acid (2.74%) were detected and the total unsaturation for the oil was 79.01%. For X. americana, 10 fatty acids were identified of which seven were unsaturated yielding a total unsaturation of 92.42%. The oil contained essential fatty acids that is, Linoleic (1.34%), Linolenic (10.31%), Arachidonic (0.60%) and varying levels of unsaturated higher fatty acids, namely, Eicosatrienoic (3.39%), Erucic (3.46%) and Nervonic (1.23%) acids. The level of Oleic acid (72.09%) in the oil was close to the value for H. barteri.     

Temporal release of fatty acids and sugars in the spermosphere: impacts on Enterobacter cloacae-induced biological control

The aim of this study was to determine the temporal release of fatty acids and sugars from corn and cucumber seeds during the early stages of seed germination in order to establish whether sugars found in exudate can prevent exudate fatty acid degradation by Enterobacter cloacae. Both saturated (long-chain saturated fatty acids [LCSFA]) and unsaturated (long-chain unsaturated fatty acids [LCUFA]) fatty acids were detected in corn and cucumber seed exudates within 15 min after seed sowing. LCSFA and LCUFA were released at a rate of 26.1 and 6.44 ng/min/seed by corn and cucumber seeds, respectively. The unsaturated portion of the total fatty acid pool from both plant species contained primarily oleic and linoleic acids, and these fatty acids were released at a combined rate of 6.6 and 0.67 ng/min/seed from corn and cucumber, respectively. In the absence of seed exudate sugars, E. cloacae degraded linoleic acid at rates of 29 to 39 ng/min, exceeding the rate of total fatty acid release from seeds. Sugars constituted a significant percentage of corn seed exudate, accounting for 41% of the total dry seed weight. Only 5% of cucumber seed exudate was comprised of sugars. Glucose, fructose, and sucrose were the most abundant sugars present in seed exudate from both plant species. Corn seeds released a total of 137 microg/seed of these three sugars within 30 min of sowing, whereas cucumber seeds released 0.83 microg/seed within the same time frame. Levels of glucose, fructose, and sucrose found in corn seed exudate (90 to 342 microg) reduced the rate of linoleic acid degradation by E. cloacae to 7.5 to 8.8 ng/min in the presence of either sugar, leaving sufficient concentrations of linoleic acid to activate Pythium ultimum sporangia Our results demonstrate that elevated levels of sugars in the corn spermosphere can prevent the degradation of LCUFA by E. cloacae, leading to its failure to suppress P. ultimum sporangial activation, germination, and subsequent disease development.     

猫儿屎和三叶木通种子油中脂肪酸成分的GC-MS分析

采用索氏提取法提取木通科植物猫儿屎和三叶木通种子的脂溶性成分,甲酯化处理后用气相色谱-质谱联用技术(GC-MS)分离和鉴定其组成和含量。从猫儿屎种子油中鉴定出9种脂肪酸,占检出物总质量分数的94.67%(其中饱和脂肪酸占12.63%,不饱和脂肪酸占82.04%),主要成分为9-十六烯酸(47.22%)、9-油酸(27.13%)、棕榈酸(10.75%)、亚油酸(7.47%)和硬脂酸(1.61%)。从三叶木通种子油中鉴定出10种脂肪酸,占检出物总质量分数的99.75%(其中饱和脂肪酸占23.39%,不饱和脂肪酸占76.36%),主要成分为11-油酸(47.63%)、亚油酸(27.05%)、棕榈酸(20.14%)、16-甲基-十七烷酸(3.03%)和8-油酸(1.07%)。结果表明,猫儿屎和三叶木通种子油中脂肪酸含量丰富,在食用、医疗保健等方面具有较高的应用潜力和综合开发前景。     

Fatty acid composition of lipids from differentiated tissues and cell cultures of Euonymus europaeus

The fatty acid patterns of Euonymus europaeus callus cultures and cell suspension cultures were analysed at the beginning of stationary growth phase and compared with those from the respective differentiated tissues. The lipid and fatty acid patterns in cell cultures differed remarkably from those in the tissues of the mother plant. No glycerol triacetate was detected in the callus cultures derived from differentiated tissues whereas in seeds this lipid compound amounts to 29%. In addition to fatty acids normally occurring in differentiated tissues, lipids in cultured cells also contained short-chain (C₁₂–C₁₄) as well as very long-chain fatty acids (C₂₀–C₂₄). In tissue culture cells the major fatty acids were found to be saturated, whereas in the mother cells unsaturated fatty acids were predominant. Palmitic acid is the most abundant fatty acid in most of the cultures. Lauric, myristic and palmitic acid amount to 50% in lipids of cell suspension cultures.     

不同产地长柄扁桃种仁成分分析

采用GC-MS、AAS、HPLC等方法对选自陕西神木、内蒙古包头、内蒙古阿拉善盟、河北承德4个不同产地的长柄扁桃种仁的一般成分(粗脂肪、粗蛋白、水分、灰分、总糖、总膳食纤维)、氨基酸、微量元素、脂肪酸及苦杏仁苷含量等进行分析。研究表明,不同产地长柄扁桃种仁各组分含量有一定差别,但均富含粗脂肪(416~478g/kg)和粗蛋白(206~286g/kg);种仁中氨基酸种类齐全,含量丰富;均含Ca、Mg、P、Fe、K等9种对人体有益的矿质元素,未检出Pb、Cd、Hg、As等元素;长柄扁桃油中不饱和脂肪酸含量在96.8%以上,以油酸和亚油酸主;苦杏仁苷含量在3%左右。从测定结果来看,长柄扁桃种仁可以作为开发食用油、蛋白粉以及苦杏仁苷的原材料,具有较好的经济价值,适宜于广大北方荒漠地区推广种植。     

Determination of the lipid classes and fatty acid profile of Niger (Guizotia abyssinica Cass.) seed oil

Niger seeds (Guizotia abyssinica Cass.), which are of interest as a new source of vegetable oils, were subjected to Soxhlet-extraction with n-hexane and the extract analysed using a combination of CC, GC, TLC and normal-phase HPLC. The total lipid content was ca. 300 mg/g seed material, and the fatty acid profile showed a high content of linoleic acid (up to 63%) together with palmitic acid (17%), oleic acid (ca. 11%), and stearic acid (ca. 7%). CC separation over silica gel eluted with solvents of increasing polarity yielded 291 mg/g of neutral lipids, 5.76 mg/g of glycolipids, and 0.84 mg/g of phospholipids. GC analysis showed that the major fatty acid present in all lipid classes was linoleic acid together with minor amounts of palmitic, oleic and stearic acids. Polar lipid fractions, however, were characterised by higher levels of palmitic acid and a lower content of linoleic acid. Phospholipid classes separated by normal-phase HPLC consisted of phosphatidylcholine (ca. 49%), phosphatidylethanolamine (22%), phosphatidylinositol (14%), phosphatidylserine (ca. 8%), and minor amounts (2-3%) of phosphatidylglycerol and lysophosphatidylcholine.     

用GC-MS分析不同采收和贮存时期的麻疯树种子油的脂肪酸

将采收于青果期、黄果期、黑果期及储存1a、2a的麻疯树种子提油,测定其理化性质,并利用GC-MS分析这5个不同时期的种子所提取的麻疯树种子油成分。结果表明:5个油样的水分、酸值、出油率有较大差异,主要化学成分、碘值、皂化值差异不大。青果的出油率为13.13%,水分为0.66%,酸值为69.21,不饱和脂肪酸含量最低。新采成熟果实的出油率为54.64%,水分为0.36%,酸值为1.51,不饱和脂肪酸含量也相对较高。因此,新采的成熟果实较为适合作生物柴油的原料。     

Lipid composition of the extracellular matrix of Botrytis cinerea germlings

Six simple lipid classes (mono-, di- and tri-acylglycerols, free fatty acids, free fatty alcohols and wax esters) were identified by TLC in the extracellular matrix of Botrytis cinerea germlings and the molecular components of each class were characterized using GC-MS. The relative amounts of fatty acids and fatty alcohols within each lipid class were determined by GC-FID. Over all the lipid classes, the most abundant saturated fatty acids were palmitic (ca. 30%) and stearic acid (ca. 22%). Palmitoleic and oleic acids made up ca. 21% and 24% (respectively) of the free fatty acids, while erucic (ca. 4.1%) and linoleic (ca. 3.6%) acids were the most abundant unsaturated fatty acids in the acylglycerides. The acylglycerides also contained almost 35% long chain fatty acids (C20:0 to C28:0). Six fatty acids were identified which had odd-numbered carbon chain lengths (C15:0, C17:0, C19:0, C21:0, C23:0 and C25:0). Of these, pentacosanoic acid made up almost 14% of the fatty acids in the acylglycerides. Three methyl-branched chain fatty acids, namely isopalmitic, isoheptadecanoic and anteisopalmitic, were identified in the ECM, all in small amounts. Of the fatty alcohols identified, only palmityl and stearyl alcohols were found in the free form (ca. 57% and 43%, respectively) but arachidyl alcohol (ca. 47%) and 1-octacosanol (ca. 30%) were the most abundant fatty alcohols found in the wax ester fraction.     

Horse chestnut (Aesculus hippocastanum L.) seed fatty acids,flavonoids and heavy metals plasticity to different urban environments

Horse chestnut (Aesculus hippocastanum L.) is a deciduous tree which is widely used on urban green spaces in Serbia. Also, the seed of horse chestnut is an important raw material in pharmaceutical industry, owing to its medicinal properties. In this study, the content of fatty acids, flavonoids, aescin and heavy metals in seeds of 11 horse chestnut genotypes growing in urban conditions was investigated. A total of 16 fatty acids were identified. Unsaturated fatty acids in seed samples were the most abundat. Among the saturated fatty acids, palmitic acid was the dominant one, with a total average content of 8.12%. Oleic acid, with the total average content of 53.46%, was the most abundant unsaturated fatty acid. The results of this study indicated the presence of the following flavonoids: quercetin, kaempferol and rutin. Rutin was the most abundant, averagely contributing with 6.071 μg/g to the total quantified polyphenolics in all samples. The total aescin content ranged from 0.82% to 4.16%. Fruits of park and street trees from small- and middle-sized cities can be used in pharmaceutical industry as raw material. Differences between different urban site categories and localities were detected, which indicates the biochemical plasticity of the seeds to urban morphology.     

Lipids in Cruciferae IX. The Effect of Growth Temperature and Stage of Development on the Fatty Acid Composition of Leaves, Siliques and Seeds of "Zero-erucic-acid" Breeding Lines of Brassica napus

Two breeding lines of “zero-erucic-acid” rapeseed (Brassica napus) were grown in climate chambers at a constant night temperature (12°C) and constant photoperiod (16 hours) but with different day temperatures (15, 20 and 25°C). Samples of leaves, siliques and immature seeds were analysed for total fatty acid pattern. The content of different acyl lipids and the fatty acid pattern of these lipids were also determined in some of the samples by use of preparative TLC followed by GLC of the fatty acids. The mature seeds produced by ten plants of each selection in each climate were analysed separately for total fatty acid composition. Mono- and digalactosyl diglycerides (MGDG, DGDG) were the predominant acyl lipids in leaves and siliques. In developing seeds they also were more abundant than the phospholipids, but in this case the neutral lipids, mainly triacylglycerols, contained about 95% of the total fatty acids. Large variations were found in the fatty acid composition of monogalactosyl diglyceride and digalactosyl diglyceride, isolated from leaves, siliques and immature seeds. The palmitic acid content of leaf MGDG was about 15 %, atypically high for MGDG from photosynthetic tissue. The linolenic acid content of the MGDG was about 45 %, 30 % and 10 % in the leaf, silique and seed tissues respectively. A hexadecatrienoic acid (16: 3) was found almost exclusively in the MGDG samples of leaves, siliques and immature seeds (about 25 %, 10 % and 3 % 16:3 respectively). The lipids of siliques — mainly photosynthetising tissue — were different from those of leaves and had especially high contents of stearic acid (6–12 % in the different lipids). For all lipid classes studied, leaves grown at the lowest day temperature had a slightly lower oleic and higher linolenic acid content than those grown at the highest temperature. On the other hand, increasing the day temperature caused a decreased level of oleic, an increased level of linoleic and an essentially unchanged level of linolenic acids in the mature seeds from both selections.     

黄蜀葵种子形态及其化学成分的研究

本文报道了黄蜀葵种子的形态特征和化学成分。研究结果表明 :种子含有脂肪油 ,含量为31 16 % ,其主要成分为 :亚油酸 (82 179% )、油酸 (9 195 % )、棕榈酸 (4 75 6 % )、硬脂酸 (2 6 81% )、亚麻酸 (0 32 8% )等 ,此外 ,还含有 18种氨基酸和 2 4种矿质元素。其种子含有多种氨基酸和矿质元素 ,而且种子油含有大量人体所必需的不饱和脂肪酸 ,含量达 91 815 %。因此 ,其种子和种子油具有较高的营养价值和医疗保健功效 ,具有潜在开发利用的价值。     

The fatty acid compositions of seed oils and their significance in the taxonomy of the family Ulmaceae

22 kinds of seed oils were extracted from 8 genera of the family Ulmaceae in China The seed oils were examined for their characteristics and fatty acid compositions by gas liquid chromatography. The fatty acid compositions of these oils were found to fall into two classes. Some genera (such as Ulmus, Zelkova) contain mainly lower saturated acids, in which the chief acid is capric acid 10:0, while the genera (such as Celtis, Pteroceltis, Aphananthe, Trema, Gironniera) contain mainly unsaturated acids, in which the chief acid is linoleic acid 18:2. Hemiptelea davidii (Hance) Planch contain however either certain amount of short-chain saturated acids or higher unsaturated acids, it appears a intermediate genus between the two classes. According to the component acids we support that the Ulmaceae be split into two subfamilies. The genera arrangement based on the component acids corresponds basically with the view based on mophological characters and flavonoids found in leaves of Ulmaceae, but there are some discrepancies in certain genera, for example, the Aphananthe should beplaced in Celtoid instead of Ulmoid by the present study.     

女贞果实及种子的化学成分

女贞子为木犀科植物女贞 (ＬｉｇｕｓｔｒｕｍｌｕｃｉｄｕｍＡｉｔ.)的果实 ,有滋补肝肾、明目乌发等功效 ,主治眩晕耳鸣、腰膝酸软、须发早白和目暗不明等症 ,女贞子主产江苏、浙江、福建、湖南、广东、广西、江西和四川等省区 ,资源丰富。女贞的化学成分已有报道[1,2 ] ,作者对其全果及种子的化学成分进行较全面分析 ,旨在为其综合开发利用提供科学依据。1　材料和方法1 1　材料和仪器女贞子 2 0 0 0年 11月至 2 0 0 1年 3月分批采自福建省福州市建新郊区、仓山长安山和永泰方广岩。石油醚 (30～6 0℃ )和乙醇等均为分析纯 (上海生化制品…     

Analysis of the fixed oils of the genus Nigella L. (Ranunculaceae) in Turkey

The fatty acid composition of fixed oils obtained from the seeds of 10 species of Nigella (Nigella orientalis L., Nigella oxypetala L., Nigella latisecta P.H. Davis, Nigella segetalis Bieb., Nigella arvensis L., Nigella damascena L., Nigella elata Boiss., Nigella nigellastrum (L.) Willk., Nigella unguicularis (Lam.) Spenner, and Nigella lancifolia Hub.-Mor.) from Turkey have been investigated. The seeds contained 17.6–41.3% fixed oils. Linoleic (31.21–69.5%) and oleic acids (15.79–36.03%) were the major fatty acids in the oils. Eicosenoic acid was found in high amounts in the oils of N. nigellastrum and N. unguicularis seeds (23.12 and 17.47%, respectively). N. nigellastrum, N. elata and N. unguicularis seed oils showed the highest concentration of eicosadienoic acid (9.40, 8.39 and 7.17%, respectively). In all fixed oils, the quantities of unsaturated fatty acids were higher than those of the saturated analogues.     

Reducing saturated fatty acids in Arabidopsis seeds by expression of a Caenorhabditis elegans 16:0–specific desaturase

Plant oilseeds are a major source of nutritional oils. Their fatty acid composition, especially the proportion of saturated and unsaturated fatty acids, has important effects on human health. Because intake of saturated fats is correlated with the incidence of cardiovascular disease and diabetes, a goal of metabolic engineering is to develop oils low in saturated fatty acids. Palmitic acid (16:0) is the most abundant saturated fatty acid in the seeds of many oilseed crops and in Arabidopsis thaliana. We expressed FAT–5, a membrane‐bound desaturase cloned from Caenorhabditis elegans, in Arabidopsis using a strong seed‐specific promoter. The FAT‐5 enzyme is highly specific to 16:0 as substrate, converting it to 16:1?9; expression of fat‐5 reduced the 16:0 content of the seed by two‐thirds. Decreased 16:0 and elevated 16:1 levels were evident both in the storage and membrane lipids of seeds. Regiochemical analysis of phosphatidylcholine showed that 16:1 was distributed at both positions on the glycerolipid backbone, unlike 16:0, which is predominately found at the sn‐1 position. Seeds from a plant line homozygous for FAT–5 expression were comparable to wild type with respect to seed set and germination, while oil content and weight were somewhat reduced. These experiments demonstrate that targeted heterologous expression of a desaturase in oilseeds can reduce the level of saturated fatty acids in the oil, significantly improving its nutritional value.     

唇形科益母草等7种植物果实化学成分分析及形态特征

益母草、白花益母草、紫苏、野紫苏、小鱼仙草、石荠苎和细风轮菜系唇形科常见的药用植物。常生于路旁、沟边及空旷草地 ,民间也有广泛栽培。分布于广东、广西、湖南、湖北、云南、贵州、浙江、安徽、福建等省区。益母草、白花益母草民间全草入药 ,有活血调经、去痰生津的功效 ,果实称茺蔚子。用于月经不调 ,产后子宫出血及复位不全等症 [14 ]。野紫苏和紫苏的果实有镇咳、平喘和祛痰的功效 ,用于治疗咳嗽气喘、肠热便秘等症 [3 ] 。小鱼仙草用于治疗感冒头痛 ,胃炎 ,肾积水等症。石荠苎全草入药 ,用于治疗胃炎 ,慢性气管炎和肺积水等症[1] …     

Synthesis and characterization of vegetable oil derived esters: evaluation for their diesel additive properties

Trans-esterification of four vegetable oils; canola oil, greenseed canola oil from heat-damaged seeds, processed waste fryer grease and unprocessed waste fryer grease, was carried out using methanol, and KOH as catalyst. The methyl esters of the corresponding oils were separated from the crude glycerol, purified, and characterized by various methods to evaluate their densities, viscosities, iodine values, acid numbers, cloud points, pour points and gross heat of combustion, fatty acid and lipid compositions, lubricity properties, and thermal properties. The fatty acid composition suggests that 80-85% of the ester was from unsaturated acids. Substantial decrease in density and viscosity of the methyl esters compared to their corresponding oils suggested that the oils were in their mono or di glyceride form. The lubricity of the methyl esters, when blended at 1 vol% treat rate with ISOPAR M reference fuel, showed that the canola methyl ester enhanced the fuel's lubricity number. From the analyses performed, it was determined that the ester with the most potential for being an additive or a substitute for diesel fuel is the canola methyl ester, whose physical and chemical characteristics are similar to diesel fuel.     

Characterization of seed oils from fresh Bokbunja (Rubus coreanus Miq.) and wine processing waste

The physicochemical characteristics, fatty acid (FA) profile, and triacylglyceride (TAG) composition of seed oils from fresh Bokbunja (Rubus coreanus Miq.) fruits and traditional Bokbunja wine processing waste were determined in this study. Oil contents of the fresh seeds and the seeds from wine processing waste were similar, accounting for about 18% of dry weight. The free fatty acid (FFA) content between the two seed oils was significantly different (0.50% for fresh seed oil and 73.14% for wine seed oil). Iodine, conjugated diene, saponification values, and unsaponifiable matter were very similar in the oil samples, but the specific extinction coefficients at 232 and 270 nm of wine seed oil were higher than those of fresh seed oil. Linoleic (C18:2, 50.45-53.18%, L) and linolenic (C18:3, 29.36-33.25%, Ln) acids were the dominant FAs in the two seed oils, whereas oleic (C18:1, 7.32-8.04%, O), palmitic (C16:0, 1.55-1.65%, P), and stearic (C18:0, 0.65-0.68%, S) acids were the minor FAs. LLL, OLL, LLLn, OOL, LLnLn, and OOO were the abundant TAGs, representing >90% of the oils.