Comparison of 37 Fatty Acids and Squalene in Walnut Oil and Common Vegetable Oils
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摘要: 为探明核桃油与大豆油、芝麻油和玉米胚芽油等常用植物油的营养价值差异,本研究采用气-质联用法和气相色谱法对4种植物油中37种脂肪酸和角鲨烯的含量进行了测定,并开展了对比分析。结果表明,核桃油与常用植物油营养价值存在显著差异(P<0.05),核桃油富含α-亚麻酸、二十碳二烯酸和亚油酸3种多不饱和脂肪酸以及油酸等单不饱和脂肪酸,还含有少量的棕榈酸及硬脂酸等饱和脂肪酸,核桃油中多不饱和脂肪酸组成与比例显著高于其他植物油(P<0.05),而饱和脂肪酸则显著低于其他植物油(P<0.05);核桃油中角鲨烯含量略低于芝麻油,属于优质植物油。4种植物油中总脂肪酸含量从高到低顺序依次为大豆油、芝麻油、核桃油和玉米胚芽油,含量分别为78.11、73.96、69.20和48.83 g/100 g;4种植物油均含α-亚麻酸、亚油酸和二十碳二烯酸等人体必需脂肪酸(Essential fatty acids,EFA),EFA含量从高到低依次为核桃油、大豆油、玉米胚芽油和芝麻油,分别占总脂肪酸的90.0%、70.7%、64.9%和54.1%;4种植物油的油酸含量与亚油酸含量的比值(油亚比R)由高到低依次为芝麻油、玉米胚芽油、大豆油和核桃油,分别为0.62、0.35、0.27和0.10,表明4种植物油中,芝麻油的抗氧化能力最大,可保存时间最长。大豆油、核桃油和芝麻油中均检出角鲨烯,其含量从高到低依次为大豆油、芝麻油和核桃油,含量分别为173.3、72.9和31.4 mg/kg,玉米胚芽油中仅含有微量的角鲨烯,未检出。本研究表明不同植物油中脂肪酸及角鲨烯等营养物质含量存在差异,可为食用植物油的营养价值分析、相关的食品和保健品等产品研发提供科学依据。Abstract: To explore the difference of nutritional value between walnut oil and soybean oil, sesame oil, corn germ oil and other common vegetable oils. The content of 37 fatty acids and squalene in four vegetable oils were determined by the gas-mass spectrometry and gas chromatography method, and the results were compared and analyzed. The results showed that walnut oil and vegetable oil commonly used nutritional value exists significant difference (P<0.05), walnut oil was rich in α-linolenic acid, eicosadienoic acid, linoleic acid 3 kinds of polyunsaturated fatty acids and oleic acid and other unsaturated fatty acids, also contained a small amount of palmitic acid, stearic acid and other saturated fatty acids, polyunsaturated fatty acid in the walnut oil composition and proportion was significantly higher than other vegetable oils (P<0.05). The composition and proportion of saturated fatty acids were significantly lower than those of other vegetable oils (P<0.05). Walnut oil contained slightly less squalene than sesame oil, making it a high-quality vegetable oil. The order of total fatty acid content was soybean oil> sesame oil>walnut oil>corn germ oil, and the contents were 78.11, 73.96, 69.20 and 48.83 g/100 g, respectively. The four vegetable oils all contained human essential fatty acids (EFA) such as α-linolenic acid, linoleic acid and eicosadienoic acid. The content of ETA from high to low was walnut oil>soybean oil>corn germ oil>sesame oil, accounting for 90.0%, 70.7%, 64.9% and 54.1% of the total fatty acids, respectively. The ratio analysis of oleic acid content to linoleic acid content showed that the order of the ratio R for four kinds of vegetable oils from high to low was sesame oil>corn germ oil> soybean oil>walnut oil, and the value was 0.62, 0.35, 0.27 and 0.10, respectively. The results showed that sesame oil had the highest antioxidant capacity and the longest shelf life among the four vegetable oils in this study. Squalene was detected in soybean oil, sesame oil and walnut oil, but not in corn germ oil. The content of squalene in soybean oil, sesame oil and walnut oil from high to low were173.3、72.9 and 31.4 mg/kg , respectively. The study indicated that the content of fatty acids and squalene in different vegetable oils were different, which would provide scientific data support for the analysis of nutritional value of edible vegetable oil and the research and development of related food and health care products.
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Key words:
- walnut oil /
- common vegetable oil /
- fatty acid /
- squalene /
- comparison
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图 1 37种脂肪酸气-质联用总离子流图
Figure 1. Total ion chromatograms of GC-MS for 37 fatty acids
注:A.37种脂肪酸标准品;B. 大豆油;C. 核桃油;D. 芝麻油;E.玉米胚芽油。1.丁酸甲酯;2.己酸甲酯;3.辛酸甲酯;4.癸酸甲酯;5.十一酸甲酯;6.月桂酸甲酯;7.十三烷酸甲酯;8.肉豆蔻酸甲酯;9.肉豆蔻脑酸甲酯;10.十五烷酸甲酯;11.顺-10-十五碳烯酸甲酯;12.棕榈酸甲酯;13.棕榈烯酸甲酯;14.十七烷酸甲酯;15.顺-10-十七碳烯酸甲酯;16.硬脂酸甲酯;17.反油酸甲酯;18.油酸甲酯;19.反亚油酸甲酯;20.亚油酸甲酯;21.γ-亚麻酸甲酯;22.α-亚麻酸甲酯;23.花生酸甲酯;24.顺-11二十碳烯酸甲酯;25.顺-11,14-二十碳二烯酸甲酯;26.二十一烷酸甲酯;27.顺8,11,14-二十碳三烯酸甲酯;28.花生四烯酸甲酯;29.顺-11,14,17二十碳三烯酸甲酯;30.榆树酸甲酯;31.EPA甲酯;32.顺芥子酸甲酯;33.顺-13,16-二十二碳二烯酸甲酯;34.二十三烷酸甲酯;35.木蜡酸甲酯;36.神经酸甲酯;37. DHA甲酯。
表 1 核桃油和常用植物油中脂肪酸含量(g/100 g)
Table 1. Fatty acid content in walnut oil and common vegetable oils (g/100 g)
类别 脂肪酸种类 核桃油 大豆油 玉米胚芽油 芝麻油 饱和脂肪酸SFA 辛酸 C8:0 0.00232±0.00b 0 0.00325±0.00a 0 肉豆蔻酸 C14:0 0.00503±0.00c 0.0306±0.00a 0.0106±0.00b 0.00631±0.00c 十五酸 C15:0 0.00542±0.00a 0.00502±0.00a 0.00230±0.00b 0.000773±0.00c 棕榈酸 C16:0 1.25±0.01d 7.10±0.00a 5.15±0.01c 5.51±0.01b 十七酸 C17:0 0.00864±0.00c 0.0370±0.00a 0.0176±0.00b 0.0153±0.00b 硬脂酸 C18:0 0.257±0.00d 2.34±0.00b 0.526±0.00c 3.37±0.00a 花生酸 C20:0 0.00774±0.01d 0.117±0.09b 0.0927±0.02c 0.268±0.11a 二十一酸 C21:0 0.00129±0.37c 0.00670±0.30a 0.00135±0.01c 0.00245±0.01b 山嵛酸 C22:0 0.00245±0.00d 0.139±0.01a 0.0426±0.00c 0.0585±0.01b 二十三酸 C23:0 0 0.0113±0.00a 0.00325±0.00c 0.00696±0.00b 二十四酸 C24:0 0 0.0366±0.00b 0.0395±0.00a 0.0302±0.00c 合计 1.54±0.01d 9.82±0.01a 5.89±0.03c 9.27±0.03b 单不饱和脂肪酸MUFA 棕榈油酸 C16:1, cis-9 0.0173±0.00d 0.0380±0.00b 0.0250±0.00c 0.0488±0.00a 二十碳烯酸 C20:1, cis-11 0.0842±0.00a 0.0599±0.00b 0.0543±0.00c 0.0608±0.00b 油酸 C18:1, cis-9 5.32±0.00d 13.0±0.00b 11.1±0.00c 24.6±0.00a 合计 5.42±0.02d 13.1±0.11b 11.2±0.03c 24.7±0.04a 多不饱和脂肪酸PUMA α–亚麻酸 C18:3, cis-9, 12, 15 10.9±0.02a 7.93±0.01b 0.238±0.01c 0.185±0.00d 二十碳二烯酸 C20: 2, cis-11, 14 0.0146±0.00a 0.00935±0.00b 0.00284±0.00d 0.00580±0.00c 亚油酸 C18: 2, cis-9, 12 51.4±0.15a 47.3±0.08b 31.5±0.07d 39.9±0.11c 合计 62.3±0.17a 55.2±0.10b 31.7±0.08d 40.1±0.11c 总脂肪酸TFA 合计 69.2±0.21c 78.2±0.22a 48.8±0.14d 74.1±0.18b 注:同行不同小写字母表示差异显著(P<0.05);表3同。 表 2 不同植物油中必需脂肪酸占比
Table 2. Proportion of essential fatty acids in different vegetable oils
类别 核桃油 大豆油 玉米胚芽油 芝麻油 ω-3(%) 10.92 7.94 0.24 0.18 ω-6(%) 51.34 47.28 31.47 39.82 EFA(%) 62.26 55.22 31.71 40.00 TFA(%) 69.20 78.11 48.83 73.96 E/T(%) 90.00 70.70 64.90 54.10 ω-6/ω-3 4.70 6.00 132.20 215.90 表 3 不同植物油中角鲨烯含量(mg/kg)
Table 3. Squalene content in different vegetable oils (mg/kg)
样品名称 核桃油 芝麻油 大豆油 玉米胚芽油 角鲨烯含量 31.4±1.85c 72.9±0.50b 173.3±11.89a ND 注:ND表示未检出。 -
[1] 赵新楠, 王秀嫔, 李培武, 等. 基于超高效液相色谱-高分辨质谱法的油料作物脂质组学分析[J]. 分析测试学报,2020,39(6):697−704. [ZHAO X N, WANG X B, LI P W, et al. Lipidomics analysis of oil crops based on ultra-high performance liquid chromatography-high resolution mass spectrometry[J]. Journal of Instrumental Analysis,2020,39(6):697−704. doi: 10.3969/j.issn.1004-4957.2020.06.001ZHAO X N, WANG X B, LI P W, et al. Lipidomics analysis of oil crops based on ultra-high performance liquid chromatography-high resolution mass spectrometry[J]. Journal of Instrumental Analysis, 2020, 39(6): 697-704. doi: 10.3969/j.issn.1004-4957.2020.06.001 [2] YE Z, LI R Z, CAO C, et al. Fatty acid profiles of typical dietary lipids after gastrointestinal digestion and absorbtion: A combination study between in-vitro and in-vivo[J]. Food Chem,2019,280:34−44. doi: 10.1016/j.foodchem.2018.12.032 [3] 王利民, 符真珠, 高杰, 等. 植物不饱和脂肪酸的生物合成及调控[J]. 基因组学与应用生物学,2020,39(1):254−258. [WANG L M, FU Z Z, GAO J, et al. Molecular mechanism of unsaturated fatty acids synthesis and regulation in plant[J]. Genomics and Applied Biology,2020,39(1):254−258.WANG L M, FU Z Z, GAO J, et al. Molecular mechanism of unsaturated fatty acids synthesis and regulation in plant[J]. Genomics and Applied Biology, 2020, 39(01): 254-258. [4] 杨敏, 魏冰, 孟橘, 等. ω-3多不饱和脂肪酸的来源及生理功能研究进展[J]. 中国油脂,2019,44(10):110−115. [YANG M, WEI B, MENG J, et al. Progress in sources and physiological function of ω-3 polyunsaturated fatty acids[J]. China Oils and Fats,2019,44(10):110−115.YANG M, WEI B, MENG J. et al. Progress in sources and physiological function of ω-3 polyunsaturated fatty acids[J]. China Oils and Fats, 2019, 44(10): 110-115. [5] 郑淑容. 脂肪酸的营养功能[J]. 畜禽业,2012(9):55−57. [ZHENG S R. Nutritional functions of fatty acids[J]. Livestock and Poultry Industry,2012(9):55−57. doi: 10.3969/j.issn.1008-0414.2012.09.046ZHENG S R. Nutritional functions of fatty acids[J]. Livestock and Poultry Industry, 2012(9): 55-57. doi: 10.3969/j.issn.1008-0414.2012.09.046 [6] 晁红娟, 雷占兰, 刘爱琴, 等. Omega-3多不饱和脂肪酸性质、功能及主要应用[J]. 中国食品添加剂,2019,30(10):122−130. [CHAO H J, LEI Z L, LIU A Q, et al. Properties, functions and main applications of omega-3 polyunsaturated fatty acids[J]. China Food Additives,2019,30(10):122−130.CHAO H J, LEI Z L, LIU A Q, et al. Properties, functions and main applications of omega-3 polyunsaturated fatty acids[J]. China Food Additives, 2019, 30(10): 122-130. [7] 阿拉坦图雅, 张丽, 乌志颜, 等. 9 种食用植物油脂肪酸成分分析[J]. 赤峰学院学报(自然科学版),2019,35(12):5−7. [A L T T Y, ZHANG L, WU Z Y, et al. Analysis of fatty acid components in 9 edible vegetable oils[J]. Journal of Chifeng University,2019,35(12):5−7.A L T T Y, ZHANG L, WU Z Y, et al. Analysis of fatty acid components in 9 edible vegetable oils[J]. Journal of Chifeng University, 2019, 35 (12): 5-7. [8] 徐云, 周玉婷, 熊婷, 等. 常见植物油以及调和油研究进展[J]. 粮油与饲料科技,2021(5):8−12. [XU Y, ZHOU Y T, XIONG T, et al. Research progress of common vegetable oil and blend oil[J]. Grain Oil and Feed Technology,2021(5):8−12. doi: 10.3969/j.issn.1008-6137.2021.05.003XU Y, ZHOU Y T, XIONG T, et al. Research progress of common vegetable oil and blend oil[J]. Grain Oil And Feed Technology, 2021(5): 8-12. doi: 10.3969/j.issn.1008-6137.2021.05.003 [9] LAYÉ S, NADJAR A, JOFFRE C, et al. Anti-inflammatory effects of omega-3 fatty acids in the brain: Physiological mechanisms and relevance to pharmacology[J]. Pharm Rev,2018,70(1):12−38. doi: 10.1124/pr.117.014092 [10] HAYES D, ANGOVE M J, TUCCI J, et al. Walnuts (Juglans regia) chemical composition and research inhuman health[J]. Crit Rev Food Sci Nutr,2016,56(8):1231−1241. doi: 10.1080/10408398.2012.760516 [11] 易善军. 世界核桃生产概况及中国核桃提升策略[J]. 四川林业科技,2017,38(5):105−108. [YI S J. General situation of international walnut production and promotion strategy of walnut industry in China[J]. Journal of Sichuan Forestry Science and Technology,2017,38(5):105−108.YI S J. General situation of international walnut production and promotion strategy of walnut industry in China[J]. Journal of Sichuan Forestry Science and Technology, 2017, 38(5): 105-108. [12] OZCAN M M, IMAN C, ARSLAN D. Physicochemical properties, fatty acid and mineral content of some walnuts (Juglans regia L.) types[J]. Agric Sci,2010,1(2):62−67. [13] GRIEL A E, KRIS-ETHERTON P M. Tree nuts and thelipid profile: A review of clinical studies[J]. Brit J Nutr,2006,96:68−78. doi: 10.1017/BJN20061866 [14] TSAMOURIS G, HATZIANTONIOU S, DEMETZOS C. Lipid analysis of greek walnut oil (Uglans regia L.)[J]. Zeitschrift Fur Natur forschung Section C,2002,57(1):51−56. [15] 刘纯友, 马美湖, 靳国锋, 等. 角鲨烯及其生物活性研究进展[J]. 中国食品学报,2015,15(5):147−156. [LIU C Y, MA M H, JIN G F, et al. Research process on squalene and bioactivities[J]. Journal of Chinese Institute of Food Science and Technology,2015,15(5):147−156.LIU C Y, MA M H, JIN G F, et al. Research process on squalene and bioactivities[J]. Journal of Chinese Institute of Food Science and Technology, 2015, 15(5): 147-156. [16] FARVIN K, KUMAR S, ANANDAN R, et al. Supplementation of squalene attenuates experimentally induced myocardial infarction in rats[J]. Food Chemistry,2007,105(4):1390−1395. doi: 10.1016/j.foodchem.2007.05.034 [17] REDDY L H, COUVREUR P. Squalene: A natural triterpene for use in disease management and therapy[J]. Adv Drug Deliv Rev,2009,61(15):1412−1426. doi: 10.1016/j.addr.2009.09.005 [18] HYE JC, TAYLOR W, TIMOTHY P, et al. Vibrational spectra and DFT calculations of squalene[J]. Journal of Molecular Structure,2013,1032:203−206. doi: 10.1016/j.molstruc.2012.10.008 [19] KIN S, KARADENIZ F. Biological importance and application of squalene and squalane[J]. Advances in Food and Nutrition Research,2012,65:223−233. [20] HUANG Z R, LIN Y K, FANG J Y. Biological and pharmacological activities of squalene and related compounds: Potential uses in cosmetic dermatology[J]. Molecules,2009,14(1):540−554. doi: 10.3390/molecules14010540 [21] LUCIUS W, WILLIAM S J. Application of the chlorocetal claisen reaction to the total synthesis of squalene[J]. Proceedings of the National Academy of Science of the United States of America,1970,67(3):1465−1467. doi: 10.1073/pnas.67.3.1465 [22] LUCIUS W, WILLIAM S J. Application of the Chloro Ketal Claisen Reaction to the total synthesis of squalene experimental details[J]. Proceedings of the National Academy of Science of the United States of America,1970,67(4):1810−1970. doi: 10.1073/pnas.67.4.1810 [23] 赵振东. 松节油合成生物活性角鲨烯反应路线的研究[J]. 林产化学与工程,2004,24(8):20−24. [ZHAO Z D. Study on synthesis route of bioactive squalene from turpentine[J]. Chemistry and Industry of Forest Products,2004,24(8):20−24.ZHAO Z D. Study on synthesis route of bioactive squalene from turpentine[J]. Chemistry and Industry of Forest Products, 2004, 24 (8): 20-24. [24] 孙震, 赵振东, 李冬梅, 等. 金合欢基溴合成角鲨烯反应及异构体形成机理的研究[J]. 林产化学与工程,2005,25(6):1−5. [SUN Z, ZHAO Z D, LI D M, et al. Researches on synthesis of squalene from farnesyl bromide and mechanism and mechanism of isomer formation[J]. Chemistry and Industry of Forest Products,2005,25(6):1−5.SUN Z, ZHAO Z D, LI D M, et al. Researches on synthesis of squalene from farnesyl bromide and mechanism and mechanism of isomer formation[J]. Chemistry and Industry of Forest Products, 2005, 25(6): 1-5. [25] 卢克刚, 张红霞. 植物来源角鲨烯的制备与检测方法研究进展[J]. 食品研究与开发,2019,40(9):217−224. [LU K G, ZHANG H X. Research progress in preparation and detection methods of squalene from plants[J]. Food Research and Development,2019,40(9):217−224. doi: 10.3969/j.issn.1005-6521.2019.09.037LU K G, ZHANG H X. Research progress in preparation and detection methods of squalene from plants[J]. Food Research and Development, 2019, 40(9): 217-224. doi: 10.3969/j.issn.1005-6521.2019.09.037 [26] 陈学兵, 史宣明, 赵抒娜, 等. 植物油中提取角鲨烯的研究进展[J]. 中国油脂,2013,38(11):72−75. [CHEN X B, SHI Y M, ZHAO S N, et al. Progress of squalene extraction from vegetable oils[J]. China Oils and Fats,2013,38(11):72−75.CHEN X B, SHI Y M, ZHAO S N, et al. Progress of squalene extraction from vegetable oils[J]. China Oils and Fats, 2013, 38(11): 72-75. [27] 甘欢华, 张斌, 刘钟栋, 等. 气相色谱法同时快速测定大豆油脱臭馏出物中的生育酚、植物甾醇和鲨烯含量[J/OL]. 中国油脂, 2021, 46(5): 39-42, 70.GAN H H, ZHANG B, LIU Z D, et al. Simultaneous and rapid determination of tocopherol, phytosterol and squalene in soybean oil deodorized distillate by gas chromatography[J/OL]. China Oils and Fats, 2021, 46(5): 39-42, 70. [28] 张协光, 蓝雄, 彭祖茂, 等. 气相色谱测定动植物中角鲨烯含量[J]. 食品工业,2020,41(3):303−307. [ZHANG X G, LAN X, PENG Z M, et al. Determination of squalene in plants and animals by gas chromatography[J]. The Food Industry,2020,41(3):303−307.ZHANG X G, LAN X, PENG Z M, et al. of squalene in plants and animals by gas chromatography[J]. The Food Industry, 2020, 41(3): 303-307. [29] 吕春玲, 陈小媚, 王秀嫔, 等. 气相色谱-质谱联用法测定植物油料中角鲨烯的含量及方法比较[J]. 食品工业科技,2021,42(2):210−214,222. [LU C L, CHEN X M, WANG X B, et al. Determination of squalene in vegetable oil by gas chromatography-mass spectrometry and methods comparison[J]. Science and Technology of Food Industry,2021,42(2):210−214,222.LU C L, CHEN X M, WANG X B, et al. Determination of squalene in vegetable oil by gas chromatography-mass spectrometry and methods comparison[J]. Science and Technology of Food Industry, 2021, 42(2): 210-214, 222. [30] 任传义, 张延平, 汤富彬, 等. 油茶籽油、油橄榄油、核桃油、香榧油中主要化学成分分析[J]. 食品安全质量检测学报,2015,6(12):5011−5016. [REN C Y, ZHANG Y P, TANG F B, et al. Analysis of main chemical components in camellia oil, olive oil, walnut oil and torreya seeds oil[J]. Journal of Food Safety & Quality,2015,6(12):5011−5016.REN C Y, ZHANG Y P, TANG F B, et al. Analysis of main chemical components in camellia oil, olive oil, walnut oil and torreya seeds oil[J]. Journal of Food Safety & Quality, 2015, 6(12): 5011-5016. [31] 熊秋芳, 张效明, 文静, 等. 菜籽油与不同食用植物油营养品质的比较—兼论油菜品质的遗传改良[J]. 中国粮油学报,2014,29(6):122−128. [XIONG Q F, ZHANG X M, WEN J, et al. Comparation of nutritional values between rapeseed oil and several other edible vegetable oils—discussion of rapeseed quality genetic improvement[J]. Journal of the Chinese Cereals and Oils Association,2014,29(6):122−128.XIONG Q F, ZHANG X M, WEN J, et al. Comparation of nutritional values between rapeseed oil and several other edible vegetable oils—discussion of rapeseed quality genetic improvement[J]. Journal of the Chinese Cereals and Oils Association, 2014, 29(6): 122-128 [32] WANNAMETHEE S G, JEFFERIS B J, LENNON L, et al. Serum conjugated linoleic acid and risk of incident heart failure in older man: The British regional heart study[J]. Journal of the American Hert Association,2018(7):e006653. [33] 孟阿会. 核桃油成分及抗氧化性质研究[D]. 北京: 北京林业大学, 2012.MENG A H. Studies on components and antioxidative function of walnut oil[D]. Beijing: Beijing Forestry University, 2012. [34] 赵声兰, 陈朝银, 葛锋, 等. 核桃油功效成分研究进展[J]. 云南中医学院学报,2010,33(6):71−74. [ZHAO S L, CHEN C Y, GE F, et al. Research progress on functional components of walnut oil[J]. Journal of Yunnan University of Traditional Chinese Medicine,2010,33(6):71−74. doi: 10.3969/j.issn.1000-2723.2010.06.021ZHAO S L, CHEN C Y, GE F, et al. Research progress on functional components of walnut oil[J]. Journal of Yunnan University of Traditional Chinese Medicine, 2010, 33(6): 71-74. doi: 10.3969/j.issn.1000-2723.2010.06.021 [35] 李俊南, 习学良, 熊新武, 等. 核桃的营养保健功能及功能成分研究进展[J]. 中国食物与营养,2018,24(5):60−64. [LI J N, XI X L, XIONG X W, et al. Nutritional function and functional components of walnut[J]. Food and Nutrition in China,2018,24(5):60−64. doi: 10.3969/j.issn.1006-9577.2018.05.013LI J N, XI X L, XIONG X W, et al. Nutritional function and functional components of walnut[J]. Food and Nutrition in China, 2018, 24(5): 60-64. doi: 10.3969/j.issn.1006-9577.2018.05.013 [36] 杨帆, 薛长勇. 常用食用油的营养特点和作用研究进展[J]. 中国食物与营养,2013,19(3):63−66. [YANG F, XUE C Y. Research progress on nutritional characteristics and functions of common edible oil[J]. Food and Nutrition in China,2013,19(3):63−66. doi: 10.3969/j.issn.1006-9577.2013.03.015YANG F, XUE C Y. Research progress on nutritional characteristics and functions of common edible oil[J]. Food and Nutrition in China, 2013, 19(3): 63-66. doi: 10.3969/j.issn.1006-9577.2013.03.015 [37] 马立红, 王晓梅. 多不饱和脂肪酸药理作用研究[J]. 吉林中医药,2006(12):69−70. [MA L H, WANG X M. Pharmacological effects of polyunsaturated fatty acids[J]. Jilin Journal of Traditional Chinese Medicine,2006(12):69−70. doi: 10.3969/j.issn.1003-5699.2006.12.057MA L H, WANG X M. Pharmacological effects of polyunsaturated fatty acids[J]. Jilin Journal of Traditional Chinese Medicine, 2006(12): 69-70. doi: 10.3969/j.issn.1003-5699.2006.12.057 [38] FRENCH P, STANTON C, LAWLESS F, et al. Fatty acid composition, including conjugated linoleic acid, of intramuscular fat from steers offered grazed grass, grass silage, or concentrate-based diets[J]. Journal of Animal Science,2000,78(11):2849−2855. doi: 10.2527/2000.78112849x [39] 张洪涛, 单雷, 毕玉平. n-6和n-3多不饱和脂肪酸在人和动物体内的功能关系[J]. 山东农业科学,2006(2):115−120. [ZHANG H T, SHAN L, BI Y P. Functional relationships of n-6 and n-3 polyunsaturated fatty acids in humans and animals[J]. Shandong Agricultural Sciences,2006(2):115−120. doi: 10.3969/j.issn.1001-4942.2006.02.044ZHANG H T, SHAN L, BI Y P. Functional relationships of n-6 and n-3 polyunsaturated fatty acids in humans and animals[J]. Shandong Agricultural Sciences, 2006(2): 115-120. doi: 10.3969/j.issn.1001-4942.2006.02.044 [40] 黎斌, 刘小羽, 俞璐萍, 等. 气相色谱-串联质谱法测定植物油中角鲨烯的含量[J]. 食品安全质量检测学报,2020,11(8):2385−2392. [LI B, LIU X Y, YU L P, et al. Determination of squalene in vegetable oil by gas chromatography-tandem mass spectrometry[J]. Journal of Food Safety & Quality,2020,11(8):2385−2392.LI B, LIU X Y, YU L P, et al. Determination of squalene in vegetable oil by gas chromatography-tandem mass spectrometry[J]. Journal of Food Safety & Quality, 2020, 11(8): 2385-2392. [41] 国家市场监督管理总局, 国家卫生健康委员会. GB 2716-2018 食品安全国家标准 植物油[S]. 北京: 中国标准出版社, 2018.State Market Supervision and Administration, State Health Commission. GB 2716-2018 National food safety standard for vegetable oil[S]. Beijing: China Standards Press, 2018. [42] 戚登斐, 张润光, 韩海涛, 等. 核桃油中亚油酸分离纯化技术研究及其降血脂功能评价[J]. 中国油脂,2019,44(2):104−108. [QI D F, ZHANG Z G, HAN G T, et al. Separation and purification of linoleic acid from walnut oil and its hypolipidemic function evaluation[J]. China Oils and Fats,2019,44(2):104−108. doi: 10.3969/j.issn.1003-7969.2019.02.024QI D F, ZHANG Z G, HAN G T, et al. Separation and purification of linoleic acid from walnut oil and its hypolipidemic function evaluation[J]. China Oils and Fats, 2019, 44(2): 104-108. doi: 10.3969/j.issn.1003-7969.2019.02.024 [43] KERGOMARD J, PABOEUF G, BAROUH N, et al. Stability to oxidation and interfacial behavior at the air/water interface of minimally-processed versus processed walnut oil-bodies[J]. Food Chemistry,2021,360:129880−129880. doi: 10.1016/j.foodchem.2021.129880 -