Free and Bound Phytosterols in Camellia Seed Oil and Their Dynamic Changes During Refining and Storage

Abstract

Abstract: Gas chromatography-mass spectrometry (GC-MS) was used to analyze the phytosterols of main products of camellia seed oil in China. The results showed that there were nine sterols detected in camellia seed oil, which were detected in bound and free form, with a total content of 3072.87~5713.48 mg/kg. The bound sterols were dominant, accounting for 97.4~99.4% of the total content. The main sterols include lanosterol, β-amirin and β-sitosterol. After refining, the content of free sterols decreased by 94.1%, the binding state decreased by 25.1%, and the deacidification process affected both forms of sterols most. During storage, the content of bound and free sterols decreased by 12.0% and 40.9%, respectively, and the bound sterols showed stronger oxidation stability. Through principal component analysis and load analysis of each trait, it was found that bound lanosterol and free β-sitosterol were the main characteristic components of camellia seed oil and they were stable in camellia seed oil of various origins.

Key words: camellia seed oil, free sterols, bound sterols, refining, storage

CLC Number:

TS225.1

References

[1]LUKI??M, ?LUKI??I, KRAPAC M, et al.Sterols and triterpene diols in olive oil as indicators of variety and degree of ripening[J].Food Chemistry, 2013, 136(1):251-258
[2]颜亚真, 傅彦君, 方超逸, 等.植物甾醇对油脂中体外模拟控制性释放的影响[J].中国食品学报, 2018, 18(03):37-43
[3]田丹丹, 李艳, 梅晓宏.牛油果中植物甾醇的鉴定及抗氧化、抑菌活性[J].食品科学, 2019, 40(3):30-35
[4]陈月晓, 何涛, 唐凌轩, 等.气相色谱法同时测定食品中的胆固醇和植物甾醇[J].食品科学, 2016, 37(14):180-183
[5]AZADMARD-DAMIRCHI S, DUTTA P C.Free and Esterified 4,4′-dimethylsterols in Hazelnut Oil and their Retention During Refining Processes[J].Journal of the American Oil Chemists' Society, 2007, 84(3):297-304
[6]MONTSERRAT-DE LA PAZ S, FERNáNDEZ-ARCHE M A, BERMúDEZ B, et al.The sterols isolated from evening primrose oil inhibit human colon adenocarcinoma cell proliferation and induce cell cycle arrest through upregulation of LXR[J].Journal of Functional Foods, 2015, 12:64-69
[7]COUDER-GARCíA B, JACOBO, N, ZENTELLA-DEHESA A, ROCHA-ZAVALETA L, et al.The Phytosterol Peniocerol Inhibits Cell Proliferation and Tumor Growth in a Colon Cancer Xenograft Model[J].Frontiers in Oncology, 2019, 9:1341-1352
[8]GRATTAN B J.Plant sterols as anticancer nutrients: evidence for their role in breast cancer[J].Nutrients, 2013, 5(2):359-387
[9]ALBERICI R M, FERNANDES G D, PORCARI, ANDRéIA M, et al.Rapid fingerprinting of sterols and related compounds in vegetable and animal oils and phytosterol enriched- margarines by transmission mode direct analysis in real time mass spectrometry[J].Food Chemistry, 2016, 211:661-668
[10]HAN Hao, MA Hongfei, RONG Shuang, et al.Flaxseed oil containing flaxseed oil ester of plant sterol attenuates high-fat diet-induced hepatic steatosis in apolipoprotein-E knockout mice[J].Journal of Functional Foods, 2015, 13(13):169-182
[11]张如春, 李婷婷, 李丹, 等.植物甾醇酯与维生素复配抗氧化剂对玉米油的抗氧化效果研究[J].中国粮油学报, 2018, 33(3):58-63
[12]MARQUES F G, DE O N J R, DA CUNHA L C, et al.Identification of terpenes and phytosterols in Dipteryx alata (baru) oil seeds obtained through pressing[J].Revista Brasilra De Farmacognosia, 2015, 25(5):522-525
[13]YANG C, LIU X, CHEN Z, et al.Comparison of Oil Content and Fatty Acid Profile of Ten New Camellia oleifera Cultivars[J].Journal of Lipids, 2016, 2016(2):1-6
[14]CANABATE-DIAZ B, CARRETERO A S, FERNANDEZ-GUTIERREZ A, et al.Separation and determination of sterols in olive oil by HPLC-MS[J].Food Chemistry, 2007, 102(3):593-598
[15]DIAZ T G, DURáN MERáS I, SáNCHEZ CASAS J, et al.Characterization of virgin olive oils according to its triglycerides and sterols composition by chemometric methods[J].Food Control, 2005, 16(4):339-347
[16]GáZQUEZ-EVANGELISTA D, PéREZ-CASTANO, E, SáNCHEZ-VINAS, M, et al.Using offline HPLC-GC-FID 4-Desmethylsterols Concentration Profiles,Combined with Chemometric Tools,to Discriminate Different Vegetable Oils[J].Food Analytical Methods, 2014, 7(4):912-925
[17]PHILLIPS K M, RUGGIO D M, TOIVO J I, et al.Free and Esterified Sterol Composition of Edible Oils and Fats[J].Journal of Food Composition & Analysis, 2002, 15(2):123-142
[18]徐宝成, 张良晓, 王华, 等.检测油脂中游离甾醇及精炼废弃油脂的判别[J].食品科学, 2015, 36(2):188-193
[19]CHEN Shuai, BI Yanlan, SUN Shangde, et al.The Content and Composition of Total,Free,and Esterified Sterols of Lotus Plumule Oil by GC–MSFID[J].Journal of the American Oil Chemists' Society, 2017, 94(3):363-373
[20]MIETTINEN T A, GYLLING H.Regulation of cholesterol metabolism by dietary plant sterols[J].Current Opinion in Lipidology, 1999, 10(1):9-14
[21]MALINOWSKI J M, GEHRET M M, Phytosterols for dyslipidemia.[J].American journal of health-system pharmacy, 2010, 67(14):1165-1173
[22]王俐娟, 曾秋梅, 王晓琴.组山茶属植物油脂研究进展[J].中国粮油学报, 2017, 32(11):165-171
[23]YANG K, HSU F L, CHEN C W, et al.Quality characterization and oxidative stability of Camellia seed oils produced with different roasting temperatures[J].Journal of Oleo Science, 2018, 67(4):389-396
[24]Codex Standard For Named Vegetable Oils[S].Italy: Codex Alimentarius Commission, 1999.
[25]汤富彬, 沈丹玉, 刘毅华, 等.油茶籽油和橄榄油中主要化学成分分析[J].中国粮油学报, 2013, 28(7):108-113
[26]刘小亚, 李静, 温志刚, 等.庐山和井冈山不同海拔高度野生油茶籽油及化学成分的比较[J].中国食品学报, 2019, 19(8):248-256
[27]WANG X Q, ZENG Q M, VITO V, et al.Fatty acid and sterol composition of tea seed oils: Their comparison by the “FancyTiles” approach[J].Food Chemistry, 2017, 233:302-310
[28]ISO 12228—1999 Animal and vegetable fats and oils-determination of individual and total sterols contents-gas chromatographic method[S].Switzerland: International Organization for Standardization, 1999.
[29]XU B, ZHANG L, MA F, et al.Determination of free steroidal compounds in vegetable oils by comprehensive two-dimensional gas chromatography coupled to time-of-flight mass spectrometry[J].Food Chemistry, 2017, 245:415-425
[30]GENSER B, SILBERNAGEL G, DE B G, et al.Plant sterols and cardiovascular disease: a systematic review and meta-analysis[J].European Heart Journal, 2012, 33(4):444-451
[31]CLIFTON P, KEOGH J.Cholesterol-Lowering Effects of Plant Sterols in One Serve of Wholegrain Wheat Breakfast Cereal Biscuits-a Randomised Crossover Clinical Trial[J].Foods, 2018, 7(3):39-46
[32]张东生, 薛雅琳, 金青哲, 等.精炼过程对油茶籽油品质影响的研究[J].中国油脂, 2014, 39(9):18-22
[33]石晓丽, 王亚萍, 姚小华, 等.不同精炼程度油茶籽油储藏品质变化研究[J].中国粮油学报, 2015, 30(3):51-54
[34]VERLEYEN T, SOSINSKA U, IOANNIDOU S, et al.Influence of the vegetable oil refining process on free and esterified sterols[J].Journal of the American Oil Chemists Society, 2002, 79(10):947-953
[35]LUCARINI, M, D’EVOLI, L, LOMBARDI-BOCCIA G.Phytosterols and Phytosterol Oxides in Bronte’s Pistachio (Pistacia vera L) and in Processed Pistachio Products[J].European Food Research and Technology, 2020, 246(11):307-314
[36]胡银洲, 黄伟素, 陆柏益.食品中植物甾醇氧化物研究进展[J].中国粮油学报, 2013, 028(011):117-122
[37]NOUROOZ-ZADEH J, APPELQVIST L.Isolation and quantitative determination of sterol oxides in plant-based foods: soybean oil and wheat flour[J].Journal of the American Oil Chemists' Society, 1992, 69(3):288-293
[38]PHILLIPS K M, RUGGIO D M, TOIVO J I, et al.Free and esterified sterol composition of edible oils and fats[J].Journal of Food Composition and Analysis, 2002, 15(2):123-142