Physiological Effects of Eicosapentaenoic Acid (EPA) and Docosahexaenoic Acid (DHA)—A Review

Marine lipids have long been documented to be the major source of polyunsaturated fatty acids (PUFAs), especially n-3 fatty acids such as eicosapentaenoic acid (EPA; 20:5 n-3) and docosahexaenoic acid (DHA; 22:6 n-3). Both EPA and DHA have been documented to have significant influence on biochemical and physiological changes in the body. Although these long chain PUFA exert positive influences on human nutrition and health, there are also some controversies pertaining to the functioning of these n-3 PUFAs including the extent of their requirement by the body. As marine lipids have been thoroughly reviewed often, the present review mainly focuses on works related to physiological effects of EPA and DHA.     

GC/MS分析俄罗斯鲟鱼不同部位脂肪酸组成

通过Folch法提取俄罗斯鲟鱼不同部位总脂,采用GC/MS法对其脂肪酸组成进行分析。通过质谱数据库检索和标准品对照鉴定脂肪酸组成。研究表明,鱼肉、鱼卵、鱼皮、鱼腹中脂肪酸种类及含量类似,多不饱和脂肪酸含量均大于40%,其次为单不饱和脂肪酸(30%左右)和饱和脂肪酸(17%左右),多不饱和脂肪酸以9,12-十八碳二烯酸和DHA为主。鱼肉中总脂含量12.83%,其中,多不饱和脂肪酸为42.37%,EPA+DHA为17.25%;鱼卵总脂含量为14.46%,其中n-3脂肪酸为22.10%;鱼皮含有较高含量的n-6脂肪酸(19.43%);鱼腹总脂含量14.45%,含有较高含量的多不饱和脂肪酸(42.66%)和单不饱和脂肪酸(34.07%),EPA+DHA为17.38%;鱼鳔中未检测到n-3和n-6脂肪酸;鱼肝总脂含量为55.92%,单不饱和脂肪酸含量尤为突出,高达55.81%,以9-十八碳烯酸(49.82%)为主,饱和脂肪酸含量仅为17.24%;椎骨中总脂仅为0.09%。     

Evaluating nutritional quality of pacific fish species from fatty acid signatures

Eight fish species common to the Pacific Northwest coastal waters were categorised according to total lipids in a ranking from lean fish (e.g. walleye pollock) to oily fish (e.g. herring) species. Comprehensive fatty acid signatures were compared on both the relative proportion of total fatty acids and the proportion of total carcass lipid content. Generally, fish species from the Pacific coast had a relatively high proportion of n-3 highly polyunsaturated fatty acids (n-3 HUFAs), of which more than 80% was accounted for by C20:5n-3 (EPA) and C22:6n-3 (DHA), with species-specific and lower proportions of oleic acid (C18:1n-9) and palmitic acid (C16:0) also dominating. The MUFA contents of fish were lower (P < 0.05) in the lipids of lean and low-fat fish compared to those of fattier species. In contrast, higher (P < 0.05) proportions of polyunsaturated fatty acids (PUFAs) existed in the low-fat species with DHA contents ranging from 18% to 29% in the low-fat fish and from 8% to 10% in the fattier fish, such as herring and capelin. Expressing the same fatty acid content data in terms of absolute amount of fatty acids (e.g. gFA/100 g wet tissue) showed that both EPA and DHA contents in the flesh of pollock and hake were indeed many fold lower than those found in fatty fish, such as herring. The findings confirm that it is important that both the total lipid content and the fatty acid composition of these Pacific fish food sources be considered when making evaluations on the nutritional quality.     

How does high DHA fish oil affect health? A systematic review of evidence

The health benefits of fish oil, and its omega-3 long chain polyunsaturated fatty acid content, have attracted much scientific attention in the last four decades. Fish oils that contain higher amounts of eicosapentaenoic acid (EPA; 20:5n-3) than docosahexaenoic acid (DHA; 22:6n-3), in a distinctive ratio of 18/12, are typically the most abundantly available and are commonly studied. Although the two fatty acids have traditionally been considered together, as though they were one entity, different physiological effects of EPA and DHA have recently been reported. New oils containing a higher quantity of DHA compared with EPA, such as fractionated and concentrated fish oil, tuna oil, calamari oil and microalgae oil, are increasingly becoming available on the market, and other oils, including those extracted from genetically modified oilseed crops, soon to come. This systematic review focuses on the effects of high DHA fish oils on various human health conditions, such as the heart and cardiovascular system, the brain and visual function, inflammation and immune function and growth/Body Mass Index. Although inconclusive results were reported in several instances, and inconsistent outcomes observed in others, current data provides substantiated evidence in support of DHA being a beneficial bioactive compound for heart, cardiovascular and brain function, with different, and at times complementary, effects compared with EPA. DHA has also been reported to be effective in slowing the rate of cognitive decline, while its possible effects on depression disorders are still unclear. Interestingly, gender- and age- specific divergent roles for DHA have also been reported. This review provides a comprehensive collection of evidence and a critical summary of the documented physiological effects of high DHA fish oils for human health.     

梭鱼脂肪及脂肪酸成分分析和评价

为了解梭鱼的应用价值,对江苏沿海滩涂池塘养殖梭鱼（均质量（445.8±26.9）g）6 种组织（鱼头、鱼皮、背肌、腹肌、肝脏、腹脂）的脂肪分布、性质、脂肪酸组成进行分析和评价。索氏提取法测定组织中脂肪含量,滴定法测定脂肪的碘值和酸价,气相色谱-质谱法分析脂肪酸的组成。结果表明：梭鱼体内各组织脂肪分布差异显著（P＜0.05）,其中背肌和腹肌中脂肪含量分别为3.66%、10.16%;各组织脂肪的不饱和程度较高,碘值为90～106 g/100 g;各组织脂肪酸价较高,介于4～9 mg KOH/g之间;梭鱼脂肪中C22∶6n 3和C20∶5n 3含量丰富,品质好;鱼头、背肌、腹肌中饱和脂肪酸、单不饱和脂肪酸、多不饱和脂肪酸构成比例约为1∶1.5∶（0.7～0.8）,n-3/n-6多不饱和脂肪酸比值在0.7～0.8之间,组成合理;肝脏和腹脂中脂肪含量丰富,其中含有大量的n-3和n-6多不饱和脂肪酸,因此梭鱼的内脏也具有较好的可利用前景。     

Seasonal changes of fatty acids of cuttlefish Sepia officinalis L. (Mollusca: Cephalopoda) in the north eastern Mediterranean sea

The total lipids and seasonal variations in the fatty acids of the mantle of cuttlefish (Sepia officinalis) captured in the north eastern Mediterranean were investigated and the mantle was found to be a good source of polyunsaturated fatty acids (ω3 PUFAs, in particular). In all seasons, the major fatty acids in the cuttlefish mantle were observed to be palmitic acid (16:0), stearic acid (18:0), eicosapentaenoic acid (EPA, 20:5ω3) and docosahexaenoic acid (DHA, 22:6ω3). A comparison of the saturated fatty acid (29.5–36.8%), monounsaturated fatty acids (7.81–9.84%) and polyunsaturated fatty acids (43.7–49.6%) of the cuttlefish mantle revealed that polyunsaturated fatty acids (PUFA) constituted the highest proportion. The levels of DHA in the cuttlefish mantle in autumn, winter, spring and summer were 27.6%, 28.5%, 29.5% and 23.9%, while those of EPA were 16.8%, 15.4%, 14.7% and 13.9%, respectively.     

利用生物技术生产廿碳五烯酸和廿二碳六烯酸

根据现在的了解，能产生有意义含量的廿碳五烯酸（ＥＰＡ）和廿二碳六烯酸（ＤＨＡ）的微生物有真菌和藻类。在微生物中，多不饱和脂肪酸的合成通常是以单不饱和脂肪酸、油酸为底物。合成途径中，有两个主要的反应，即碳链的增长和去饱和作用。ＥＰＡ和ＤＨＡ的生成通过ω－３代谢途径。微生物脂肪酸构成的质量和数量都受培养基的组分，通气、光照强度、温度和培养时间等环境因素的影响。大多数用于提取鱼油中的ＥＰＡ的方法也可用于微生物脂质中的ＥＰＡ的提取。几种方法被提出来生产高含量的ＥＰＡ和ＤＨＡ。它们一般是基于下列技术的结合：溶剂提取、尿素包合法、分子蒸馏、分馏、液相色谱法和超临界二氧化碳提取。     

摄食DHA-磷脂酰丝氨酸对发育期小鼠体组织DHA水平的影响

目的：比较研究断乳后干预二十二碳六烯酸-磷脂酰丝氨酸（docosahexaenoic acid-phosphatidylserine, DHA-PS）和DHA-甘油三酯（DHA-triglyceride,DHA-TG）对发育期ICR小鼠体组织DHA含量以及脂肪酸组成的影 响。方法：母鼠孕期及哺乳期喂饲n-3多不饱和脂肪酸（n-3 polyunsaturated fatty acids,n-3 PUFAs）缺乏饲料,子代 雄小鼠断乳后随机分为3 组,分别喂饲n-3 PUFAs缺乏饲料（n-3缺乏组）、DHA-TG饲料（DHA-TG组）、DHA-PS 饲料（DHA-PS组）,每组8 只,喂养2 周后检测小鼠脑皮质、精巢、肝脏、红细胞中脂肪酸组成和DHA含量。结 果：补充DHA-PS和DHA-TG可以使发育期小鼠各组织中DHA含量显著增加（P＜0.05）,二十二碳五烯酸和花生四 烯酸含量显著降低（P＜0.05）。DHA-TG组精巢中DHA含量明显高于DHA-PS组;DHA-PS组肝脏TG、磷脂和红细 胞中DHA水平显著高于DHA-TG组（P＜0.05）,而两组脑皮质DHA水平无显著性差异（P＞0.05）。结论：膳食补 充DHA-PS和DHA-TG均可明显提高发育期小鼠各组织中DHA水平,但二者的组织蓄积特性不同,DHA-PS可以更 高效地提高小鼠肝脏和红细胞中DHA水平。     

不同蛋白能量水平饲粮对黄渠桥羊羔背最长肌脂肪酸组成及含量的影响

为研究不同蛋白能量水平组合补饲日粮对宁夏地理标志农产品黄渠桥羊羔肉脂肪酸组成及含量的影响,采用随机区组设计,选择出生15 d、体质量10 kg左右的滩寒杂一代羔羊48 只,随机分为4 组,分别饲喂不同蛋白能量水平组合的全价颗粒饲料,羔羊生长体质量达20 kg屠宰后采集分析其背最长肌脂肪酸组成及含量变化。结果表明：实验3组（粗蛋白含量28.17%,代谢能11.79 MJ/kg）羔羊背最长肌多不饱和脂肪酸（polyunsaturated fatty acid,PUFA）与饱和脂肪酸（saturation fatty acid,SFA）比值（P/S）、必需脂肪酸、n-6 PUFA、n-3 PUFA、亚油酸、γ-亚麻酸、α-亚麻酸和二十二碳六烯酸含量较其他组差异显著（P＜0.05）,实验1组（粗蛋白含量18.5%,代谢能11.34 MJ/kg）n-6 PUFA与n-3 PUFA比值（n-6/n-3）、花生四烯酸和二十碳五烯酸含量较其他组差异显著（P＜0.05）;综合提示,实验3组和实验1组补饲羔羊背最长肌脂肪酸含量较其他组差异显著。     

Pasteurization Effect on Fatty Acid Stability in a Sous Vide Product Containing Seal Meat (Phoca groenlandica)

The stability of selected fatty acids in a sous vide product containing seal meat (Phoca groenlandica) plus vegetables was examined. The product was processed at five time/temperature combinations. In addition to pasteurized and nonpasteurized products, a conventionally heated (about 100°C) product was prepared for comparison. Unsaturated fatty acids constituted 81.3% of the total fatty acids in the nonpasteurized product. Eicosapentaenoic acid (EPA, 20:5n-3) was 0.9 mg/g and docosahexaenoic acid (DHA, 22:6n-3) was 1.2 mg/g in the nonpasteurized product. EPA was 19% higher and DHA 68% higher in the sample pasteurized at 65°C vs the conventional. Furthermore, pasteurization at lower temperatures retained 22% more EPA and 57% more DHA than pasteurization at higher temperatures.     

LIPID CONTENT AND FATTY ACID COMPOSITION IN THE GREEN-LIPPED MUSSEL PERNA VIRIDIS (L.)

The lipid content and fatty acid profile in soft tissue of the green-lipped mussel Perna viridis, a widely distributed tropical and subtropical bivalve species, were investigated. The total and neutral lipid contents were 6.17 ± 0.71 and 2.71 ± 0.42 mg per 100 mg dw, respectively. The content of docosahexaenoic acid (DHA, C22:6n-3) was 24.38 ± 2.50 mg/g dw whereas eicosapentaenoic acid (EPA, C20:5n-3) was present at 12.29 ± 2.12 mg/g dw. These two fatty acids were also at the top high percentage among all the fatty acids, with 38.06 ± 0.86% and 17.89 ± 1.24% (w/w) in total lipids and 34.64 ± 2.74% and 20.33 ± 1.05% (w/w) in neutral lipids, respectively. Therefore, green-lipped mussel is a rich source of DHA and EPA, the two n-3 polyunsaturated fatty acids that are beneficial to human health and nutrition.     

Long-chain n-3 PUFA against breast and prostate cancer: Which are the appropriate doses for intervention studies in animals and humans?

The potential antineoplastic effect of the long-chain n-3 polyunsaturated fatty acids (LC n-3 PUFA) eicosapentaenoic (EPA) and docosahexaenoic acid (DHA) remains a highly controversial issue. Numerous animal studies have supported the anticancer role of these dietary fatty acids, whereas conflicting results have been obtained in population studies, and only a few intervention human trials have been so far performed. In view of the possibility that the anticancer effects may be maximally observed within a defined range of EPA and DHA doses, herein we critically review the results and doses used in both animal studies and human clinical trials focusing on the possible n-3 PUFA protective effects against breast and prostate cancer. Our main aim is to identify the EPA and/or DHA ranges of doses needed to obtain clear anticancer effects. This may be of great help in designing future animal studies, and also in understanding the most appropriate dose for further human intervention studies. Moreover, since the healthy effects of these fatty acids have been strictly related to their increased incorporation in plasma and tissue lipids, we also examine and discuss the incorporation changes following the administration of the effective anticancer EPA and/or DHA doses in animals and humans.     

Atlantic salmon (Salmo salar) muscle structure integrity and lysosomal cathepsins B and L influenced by dietary n-6 and n-3 fatty acids

This study had two main objectives: first, to evaluate the impact of different types and levels of dietary n-6 and n-3 fatty acids (FAs) on Atlantic salmon muscle structure integrity; second, to highlight a possible role of lysosomes and lysosomal degrading enzymes, cathepsins, in fish muscle structure integrity, in relation to dietary fatty acids. Four groups of Atlantic salmon (90 g starting weight) in fresh water tanks were fed one of four diets containing 23% crude lipids, with 100% of the added oils as either fish oil (FO), rapeseed oil (RO), eicosapentaenoic acid (EPA) enriched-oil or docosahexaenoic acid (DHA) enriched-oil. The RO diet was characterised by low levels of EPA + DHA (10% of total FAs), whereas the EPA and DHA diets were characterised by very high levels of EPA + DHA (>50% of total FAs). Fatty acid composition of the muscle crude lysosomal fraction (CLF) generally reflected the diets. Salmon fed the RO diet presented a muscle CLF FA composition close to the one of the FO group, showing moderate PUFA levels, and comparable cathepsin B and cathepsin L activities, relative gene expression of cathepsin B and cathepsin L in the muscle and rate of myofibre–myofibre detachments post-mortem. Salmon fed the EPA and DHA-enriched-oil diets presented a fairly similar muscle CLF FA composition, but different from the FO and RO groups. In the EPA and DHA groups, the percentage of PUFAs in the muscle CLF, the rate of myofibre–myofibre detachments and the relative gene expression of cathepsin B were higher than in the FO and RO groups. Cathepsin B and cathepsin L total activities in the muscle were however lower in the EPA and DHA groups 0 h post-mortem. Dietary lipids influenced the level of lysosomal degrading enzyme activity cathepsin B and cathepsin L as well as the relative gene expression of cathepsin B. Feeding Atlantic salmon with rapeseed oil and extreme levels of EPA + DHA highlighted the impact of fatty acid composition of the diet on salmon muscle integrity and the complexity of the process involving muscle lysosomes and cathepsins in relation to these dietary fatty acids.     

泌乳期母乳脂肪酸变化及其多不饱和脂肪酸影响因素

采用气相色谱-质谱联用技术测定不同泌乳期母乳中脂肪酸的动态变化,并分析乳母血型、生育年龄、孕周、孕前身体质量指数（body mass index,BMI）、分娩方式和婴儿性别、胎次对成熟母乳中与婴儿生长发育直接相关的重要多不饱和脂肪酸（polyunsaturated fatty acid,PUFA）,亚油酸（linoleic acid,LA）、α-亚麻酸（α-linolenic acid,ALA）、花生四烯酸（arachidonic acid,AA）,二十碳五烯酸（eicosapentaenoic acid,EPA）、二十二碳六烯酸（docosahexaenoic acid,DHA）相对含量的影响。结果显示,饱和脂肪酸（saturated fatty acid,SFA）含量在初乳和成熟乳间差异显著（P＜0.05）,单不饱和脂肪酸（monounsaturated fatty acid,MUFA）含量随着泌乳期的延长逐渐降低,但差异不显著（P＞0.05）,PUFA含量在各泌乳期无显著差异（P＞0.05）,AA、DHA含量随着泌乳期的延长逐渐降低,在初乳、过渡乳中含量差异均不显著（P＞0.05）,但均显著高于成熟乳中含量（P＜0.05）;母乳中LA含量与婴儿性别有关,ALA含量与乳母孕前BMI有关,母乳中AA、EPA含量与乳母血型有关,DHA含量与乳母孕前BMI、乳母血型有关,均具有统计学意义（P＜0.05）。     

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。     

草鱼片热风干制过程中脂质氧化特性研究

探讨热风干燥过程中青鱼片油脂的变化情况。在青鱼片的不同干燥阶段提取油脂,检测油脂氧化程度,油脂成分及脂肪酸组成的含量变化。在干燥过程中鱼片油脂的过氧化值、羰基价和酸价显著性升高(P<0.05)。随着甘油三酯和磷脂含量的下降,游离脂肪酸含量明显增加,表明在干制过程中油脂在酯酶和磷酸化酶的催化下发生了水解反应。在总油脂和总磷脂中多不饱和脂肪酸,尤其是二十碳五烯酸(EPA)和二十二碳六烯酸(DHA)含量下降。在游离脂肪酸中,除DHA以外的多不饱和脂肪酸含量均显著升高。研究结果表明,青鱼片热风干燥过程中其油脂被氧化,同时发生脂质降解,特别是不饱和脂肪酸被释放为游离态。     

Health beneficial long chain omega-3 fatty acid levels in Australian lamb managed under extensive finishing systems

The variation in levels of the health claimable long chain omega-3 fatty acids, eicosapentaenoic acid (EPA, 20:5n-3) plus docosahexaenoic acid (DHA, 22:6n-3) across production regions of Australia was studied in 5726 lambs over 3 years completed in 87 slaughter groups. The median level of EPA plus DHA differed dramatically between locations and sometimes between slaughters from the same location. The ratio of EPA plus DHA from lambs with high values (97.5% quantile) to lambs with low values (2.5% quantile) also differed dramatically between locations, and between slaughters from the same location. Consistency between years, at a location, was less for the high to low value ratio of EPA plus DHA than for the median value of EPA plus DHA. To consistently obtain high levels of omega-3 fatty acids in Australian lamb, there must be a focus on lamb finishing diets which are likely to need a supply of α-linolenic acid (18:3n-3), the precursor for EPA and DHA.     

Different specificity of two types of Pseudomonas lipases for C20 fatty acids with a Delta5 unsaturated double bond and their application for selective concentration of fatty acids

Two kinds of lipases, AK-lipase and HU-lipase, produced by two different Pseudomonas fluorescens strains, AK102 and HU380, respectively, were evaluated as to fatty acid hydrolysis specificity using six types of oil containing higher amounts of C20 fatty acids such as arachidonic acid (5,8,11,14-eicosatetraenoic acid, AA, or 20:4omega6), dihomo-gamma-linolenic acid (8,11,14-eicosatrienoic acid, DGLA, or 20:3omega6), 5,8,11,14,17-eicosapentaenoic acid (EPA or 20:5omega3), mead acid (5,8,11-eicosatrienoic acid, MA, or 20:3omega9), 8,11-eicosadienoic acid (20:2omega9) and 8,11,14,17-eicosatetraenoic acid (20:4omega3). Although HU-lipase did not show any specificity for C20 fatty acids with respect to the presence or absence of a Delta5 unsaturated bond, it exhibited comparatively low reactivity for 4,7,10,13,16,19-docosahexaenoic acid (DHA or 22:6omega3). In contrast, AK-lipase was less reactive for C20 fatty acids with a Delta5 unsaturated bond. However, the specificity of hydrolysis of AK-lipase gradually decreased as the reaction proceeded. Utilizing this fatty acid specificity, we concentrated either EPA or DHA from fish oils containing both EPA and DHA by means of lipase-catalyzed hydrolysis and urea adduction. Hydrolysis and urea adduction of refined cod oil including 12.2% EPA and 6.9% DHA with HU-lipase provided free fatty acids with 43.1% EPA and 7% DHA, respectively. The resulting yield of concentrated total fatty acids comprised 2.6% of the fatty acids from the cod oil. Thus, EPA was particularly concentrated in the fatty acids derived from refined cod oil on partial hydrolysis with HU-lipase followed by urea adduction. On the other hand, hydrolysis of cuttlefish oil with AK-lipase followed by urea adduction increase slightly the EPA composition from 14.2% to 16.8%, and markedly enhanced the composition of DHA from 16.3% to 44.6% in the hydrolyzed fatty acids. The yield of purified total fatty acids by urea concentrate was 9.4% of the fatty acids from the cuttlefish oil. Thus, DHA was particularly concentrated in the fatty acids derived from on partial hydrolysis with AK-lipase followed by urea adduction. We concluded that EPA and DHA concentrates can be easily and inexpensively obtained using HU-lipase and AK-lipase, respectively. Furthermore, it might be possible to separate and concentrate C20 polyunsaturated fatty acids (PUFAs) with or without a Delta5 double bond from PUFAs rich oils including both fatty acids.     

α-亚麻酸研究进展

α-亚麻酸属于n-3系列多不饱和脂肪酸,分子结构为△9,12,15-18:3,主要来源于陆地植物, 如杜仲、藿香、亚麻、紫苏等。在体内代谢过程中,它主要作为EPA和DHA前体物质,并具有降低胆固醇、血脂,预防心血管疾病、保护视力和抑制过敏反应等功能。该文主要介绍α-亚麻酸的来源、分离提取方法进展及生理功能,并对α-亚麻酸发展前景进行展望。