Journal of the American Oil Chemists' Society

, Volume 93, Issue 2, pp 155–170 | Cite as

Characteristics of Specialty Natural Micronutrients in Certain Oilseeds and Oils: Plastochromanol-8, Resveratrol, 5-Hydroxytryptamine Phenylpropanoid Amides, Lanosterol, Ergosterol and Cyclolinopeptides

  • Jun Jin
  • Gayrat Sheraliev
  • Dan Xie
  • Wei Zhang
  • Qingzhe JinEmail author
  • Xingguo Wang


The current concern for health has raised the importance of natural micronutrients in edible oils and fats. Different from common micronutrients, e.g., tocopherols, tocotrienols, stigmasterol and sitosterol, new and emerging specialty micronutrients, such as plastochromanol-8, resveratrol, phenylpropanoid amides of 5-hydroxytryptamine, lanosterol, ergosterol and cyclolinopeptides, are becoming increasingly popular among health-conscious people. The first three are phenolic compounds, the forth and fifth sterols, and sixth a peptide. These micronutrients are usually present in certain oils or oilseed-related byproducts, including rapeseed, peanut, flaxseed, tea seed, and camellia oils, and safflower seed cakes, all of which are the highly valuable products of the lipid industry in China nowadays. The first object of this review is to discuss the characteristics of the micronutrients, mainly including their varieties, structures, and sources. Second, the antioxidant activities and indicative functions for oil quality were also analyzed in detail. Third, refining techniques, breeding programs and extraction methods are suggested. Suitable modification treatments of certain micronutrients are also advocated to make them easy to incorporate in other foods.


Natural micronutrients Oils Fats Plastochromanol-8 Resveratrol Phenylpropanoid amides of 5-hydroxytryptamine Lanosterol Ergosterol Cyclolinopeptides 



The research was financially supported by the Key Projects in the National Science and Technology Pillar Program during the Twelfth Five-year Plan Period (No. 2012BAK08B03 and No. 2011BAD02B03) and the National Key Technology R&D Program (No. 2012BAD36B06-5).


  1. 1.
    Shahidi F (2005) Bailey’s industrial oil and fat products, vol 3, 6th edn. Wiley, New York, pp 319–359CrossRefGoogle Scholar
  2. 2.
    Gunstone FD (2011) Vegetable oils in food technology composition, properties and uses, 2nd edn. Wiley, New YorkCrossRefGoogle Scholar
  3. 3.
    Gruszka J, Kruk J (2007) RP-LC for determination of plastochromanol, tocotrienols and tocopherols in plant oils. Chromatographia 66:909–913CrossRefGoogle Scholar
  4. 4.
    Zhang YM (2014) Research on the detection method and stability of resveratrol and polydatin in peanut. Master thesis, Jiangnan University (in Chinese) Google Scholar
  5. 5.
    Yi XT (2008) Enrichment of N-feruloylserotonin and N-(p-coumaroyl) serotonin in safflower (Carthamus tinctorius L.) seed meal. Master thesis, Jiangnan University (in Chinese) Google Scholar
  6. 6.
    Li LY (2014) Study on tea seed oil with ultrasound countercurrent extraction and molecular distillation refining. Master thesis, Jiangnan University (in Chinese) Google Scholar
  7. 7.
    Gui B, Shim YY, Reaney MJT (2012) Distribution of cyclolinopeptides in flaxseed fractions and products. J Agric Food Chem 60:8580–8589CrossRefGoogle Scholar
  8. 8.
    Soleas GJ, Diamandis EP, Goldberg DM (1997) Resveratrol: a molecule whose time has come? And gone? Clin Biochem 30:91–113CrossRefGoogle Scholar
  9. 9.
    Soleas GJ, Diamandis EP, Goldberg DM (1997) Wine as a biological fluid: history, production, and role in disease prevention. J Clin Lab Anal 11:287–313CrossRefGoogle Scholar
  10. 10.
    Carollo C, Caimi G (2012) Wine consumption in the Mediterranean diet: old concepts in a new sight. Food Nutr Sci 3:1726–1733CrossRefGoogle Scholar
  11. 11.
    Wang RY (2015) Overview of China’s oil fats & oilseed market in 2014. Techno-marketing seminar on palm oil in food industries. Malaysian Palm Oil Council, China Cereals and Oils Association, Hefei, pp 47–52Google Scholar
  12. 12.
    Kruk J, Szymańska R, Cela J, Munne-Bosch S (2014) Plastochromanol-8: fifty years of research. Phytochemistry 108:9–16CrossRefGoogle Scholar
  13. 13.
    Mène-Saffrané L, Jones AD, DellaPenna D (2010) Plastochromanol-8 and tocopherols are essential lipid-soluble antioxidants during seed desiccation and quiescence in Arabidopsis. Proc Natl Acad Sci USA 107:17815–17820CrossRefGoogle Scholar
  14. 14.
    Siger A, Kachlicki P, Czubiński J, Polcyn D, Dwiecki K, Nogala-Kalucka M (2014) Isolation and purification of plastochromanol-8 for HPLC quantitative determinations. Eur J Lipid Sci Technol 116:413–422CrossRefGoogle Scholar
  15. 15.
    Mène-Saffrané L, DellaPenna D (2010) Biosynthesis, regulation and functions of tocochromanols in plants. Plant Physiol Biochem 48:301–309CrossRefGoogle Scholar
  16. 16.
    Matthaus B, Vosmann K, Pham LQ, Aitzetmüller K (2003) FA and tocopherol composition of Vietnamese oilseeds. J Am Oil Chem Soc 80:1013–1020CrossRefGoogle Scholar
  17. 17.
    Rammell CG, Hoogenboom JJL (1985) Separation of tocols by HPLC on an amino-cyano polar phase column. J Liq Chromatogr 8:707–717CrossRefGoogle Scholar
  18. 18.
    Matthäus B, Özcan M (2005) Glucosinolates and fatty acid, sterol, and tocopherol composition of seed oils from Capparis spinosa Var. spinosa and Capparis ovata Desf. Var. canescens (Coss.) Heywood. J Agric Food Chem 53:7136–7141CrossRefGoogle Scholar
  19. 19.
    Górnaś P, Siger A, Segliņa D (2013) Physicochemical characteristics of the cold-pressed Japanese quince seed oil: new promising unconventional bio-oil from by-products for the pharmaceutical and cosmetic industry. Ind Crop Prod 48:178–182CrossRefGoogle Scholar
  20. 20.
    Gawrysiak-Witulska M, Siger A, Wawrzyniak J, Nogala-Kalucka M (2011) Changes in tocochromanol content in seeds of Brassica napus L. during adverse conditions of storage. J Am Oil Chem Soc 88:1379–1385CrossRefGoogle Scholar
  21. 21.
    Ahmed MK, Daun JK, Przybylski R (2005) FT-IR based methodology for quantitation of total tocopherols, tocotrienols and plastochromanol-8 in vegetable oils. J Food Compos Anal 18:359–364CrossRefGoogle Scholar
  22. 22.
    García-Navarro E, Pérez-Vich B, Velasco L (2014) Changes in plastochromanol-8 and tocopherols during germination in Ethiopian mustard lines with contrasting tocopherol levels. Seed Sci Res 24:101–112CrossRefGoogle Scholar
  23. 23.
    Shrestha K, Gemechu FG, Meulenaer BD (2013) A novel insight on the high oxidative stability of roasted mustard seed oil in relation to phospholipid, Maillard type reaction products, tocopherol and canolol contents. Food Res Int 54:587–594CrossRefGoogle Scholar
  24. 24.
    Zubr J, Matthäus B (2002) Effects of growth conditions on fatty acids and tocopherols in Camelina sativa oil. Ind Crop Prod 15:155–162CrossRefGoogle Scholar
  25. 25.
    Goffman FD, Möllers C (2000) Changes in tocopherol and plastochromanol-8 contents in seeds and oil of oilseed rape (Brassica napus L.) during storage as influenced by temperature and air oxygen. J Agric Food Chem 48:1605–1609CrossRefGoogle Scholar
  26. 26.
    Velasco L, Goffman FD (2000) Tocopherol, plastochromanol and fatty acid patterns in the genus Linum. Plant Syst Evol 221:77–88CrossRefGoogle Scholar
  27. 27.
    Ciftci ON, Przybylski R, Rudzińska M (2012) Lipid components of flax, perilla, and chia seeds. Eur J Lipid Sci Technol 114:794–800CrossRefGoogle Scholar
  28. 28.
    Olejnik D, Gogolewski M, Nogala-Kalucka M (1997) Isolation and some properties of plastochromanol-8. Nahrung 41:101–104CrossRefGoogle Scholar
  29. 29.
    Kriese U, Schumann E, Weber WE, Beyer M, Brühl L, Matthäus B (2004) Oil content, tocopherol composition and fatty acid patterns of the seeds of 51 Cannabis sativa L. genotypes. Euphytica 137:339–351CrossRefGoogle Scholar
  30. 30.
    Gawrysiak-Witulska M, Siger A, Nogala-Kalucka M (2009) Degradation of tocopherols during near-ambient rapeseed drying. J Food Lipids 16:524–539CrossRefGoogle Scholar
  31. 31.
    Gruszka J, Pawlak A, Kruk J (2008) Tocochromanols, plastoquinol, and other biological prenyllipids as singlet oxygen quenchers-determination of singlet oxygen quenching rate constants and oxidation products. Free Radic Biol Med 45:920–928CrossRefGoogle Scholar
  32. 32.
    Nowicka B, Gruszka J, Kruk J (2013) Function of plastochromanol and other biological prenyllipids in the inhibition of lipid peroxidation—a comparative study in model systems. Biochim Biophys Acta Biomembr 1828:233–240CrossRefGoogle Scholar
  33. 33.
    Zambiazi RC (1997) The role of endogenous lipid components on vegetable oil stability. PhD thesis, University of ManitobaGoogle Scholar
  34. 34.
    Pan Q (1990) Flax production, utilization and research in China, In: Proceedings of the 53rd Flax Institute of the United States of America, Flax Institute of the United States of America, North Dakota, pp 59–63Google Scholar
  35. 35.
    Choo WS, Birch EJ, Dufour JP (2007) Physicochemical and stability characteristics of flaxseed oils during pan-heating. J Am Oil Chem Soc 84:735–740CrossRefGoogle Scholar
  36. 36.
    Filip V, Plocková M, Šmidrkal J, Špičková Z, Melzoch K, Schmidt Š (2003) Resveratrol and its antioxidant and antimicrobial effectiveness. Food Chem 83:585–593CrossRefGoogle Scholar
  37. 37.
    Chen RS, Wu PL, Chiou RYY (2002) Peanut roots as a source of resveratrol. J Agric Food Chem 50:1665–1667CrossRefGoogle Scholar
  38. 38.
    Davidov-Pardo G, McClements DJ (2015) Nutraceutical delivery systems: resveratrol encapsulation in grape seed oil nanoemulsions formed by spontaneous emulsification. Food Chem 167:205–212CrossRefGoogle Scholar
  39. 39.
    Ma F, Li PW, Zhang Q, Yu L, Zhang LX (2015) Rapid determination of trans-resveratrol in vegetable oils using magnetic hydrophilic multi-walled carbon nanotubes as adsorbents followed by liquid chromatography-tandem mass spectrometry. Food Chem 178:259–266CrossRefGoogle Scholar
  40. 40.
    Wang ML, Chen CY, Tonnis B, Barkley NA, Pinnow DL, Pittman RN, Davis J, Holbrook CC, Stalker HT, Pederson GA (2013) Oil, fatty acid, flavonoid, and resveratrol content variability and FAD2A functional SNP genotypes in the U.S. peanut mini-core collection. J Agric Food Chem 61:2875–2882CrossRefGoogle Scholar
  41. 41.
    Hüsken A, Baumert A, Milkowski C, Becker HC, Strack D, Möllers C (2005) Resveratrol glucoside (piceid) synthesis in seeds of transgenic oilseed rape (Brassica napus L.). Theor Appl Genet 111:1553–1562CrossRefGoogle Scholar
  42. 42.
    Mercy OA, Simeon OO, Saheed A, Ayokunle O, Temitope AE (2014) Analysis of phenolic compounds, phytosterols, lignans and stilbenoids in garlic and ginger oil by gas chromatography. J Food Chem Nutr 2:53–60Google Scholar
  43. 43.
    Jin QZ (2013) Functional lipids. China Light Industry Press, Beijing, pp 166–168 (in Chinese) Google Scholar
  44. 44.
    Zhao X, Ma F, Li PW, Li GM, Zhang LX, Zhang Q, Zhang W, Wang XP (2015) Simultaneous determination of isoflavones and resveratrols for adulteration detection of soybean and peanut oils by mixed-mode SPE LC–MS/MS. Food Chem 176:465–471CrossRefGoogle Scholar
  45. 45.
    Celotti E, Ferrarini R, Zironi R, Conte LS (1996) Resveratrol content of some wines obtained from dried Valpolicella grapes: Recioto and Amarone. J Chromatogr A 730:47–52CrossRefGoogle Scholar
  46. 46.
    Hung CF, Lin YK, Huang ZR, Fang JY (2008) Delivery of resveratrol, a red wine polyphenol, from solutions and hydrogels via the skin. Biol Pharm Bull 31:955–962CrossRefGoogle Scholar
  47. 47.
    Rigacci S, Stefani M (2015) Nutraceuticals and amyloid neurodegenerative diseases: a focus on natural phenols. Expert Rev Neurother 15:41–52CrossRefGoogle Scholar
  48. 48.
    Xu W, Lu Y, Yao JH, Li ZL, Chen Z, Wang GZ, Jing HR, Zhang XY, Li MZ, Peng JY, Tian XF (2014) Novel role of resveratrol: suppression of high-mobility group box 1 nucleocytoplasmic translocation by the upregulation of sirtuin 1 in sepsis-induced liver injury. Shock 42:440–447CrossRefGoogle Scholar
  49. 49.
    Lekli I, Ray D, Mukherjee S, Gurusamy N, Ahsan MK, Juhasz B, Bak I, Tosaki A, Gherghiceanu M, Popescu LM, Das DK (2010) Co-ordinated autophagy with resveratrol and γ-tocotrienol confers synergetic cardioprotection. J Cell Mol Med 14:2506–2518CrossRefGoogle Scholar
  50. 50.
    Medina I, Alcántara D, González MJ, Torres P, Lucas R, Roque J, Plou FJ, Morales JC (2010) Antioxidant activity of resveratrol in several fish lipid matrices: effect of acylation and glucosylation. J Agric Food Chem 58:9778–9786CrossRefGoogle Scholar
  51. 51.
    Corduneanu O, Janeiro P, Brett AMO (2006) On the electrochemical oxidation of resveratrol. Electroanalysis 18:757–762CrossRefGoogle Scholar
  52. 52.
    Murcia MA, Martínez-Tomé M (2001) Antioxidant activity of resveratrol compared with common food additives. J Food Prot 64:379–384Google Scholar
  53. 53.
    Marinova EM, Yanishlieva NV, Totseva IR (2002) Anti-oxidant activity and mechanism of action of trans-resveratrol in different lipid systems. Int J Food Sci Technol 37:145–152CrossRefGoogle Scholar
  54. 54.
    Brewer MS (2011) Natural antioxidants: sources, compounds, mechanisms of action, and potential applications. Compr Rev Food Sci Food Saf 10:221–247CrossRefGoogle Scholar
  55. 55.
    Marinova E, Yanishlieva N, Toneva A (2004) Synergetic activity of some natural antioxidants in triacylglycerols of sunflower oil. Riv Ital Sostanze Grasse 81:290–294Google Scholar
  56. 56.
    Wani TA, Shah AG, Wani SM, Wani IA, Masoodi FA, Nissar N, Shagoo MA (2005) Suitability of different food grade materials for the encapsulation of some functional foods well reported for their advantages and susceptibility. Crit Rev Food Sci Nutr. doi: 10.1080/10408398.2013.845814 Google Scholar
  57. 57.
    Cao Y, Yu HZ, Zhang M, Li GZ, Xiao LT (2004) HPLC determination of resveratrol content in Polygonum cuspidatum and the stability of resveratrol. Chem Ind For Prod 24:61–64 (in Chinese) Google Scholar
  58. 58.
    Sanders TH, McMichael RW, Hendrix KW (2000) Occurrence of resveratrol in edible peanuts. J Agric Food Chem 48:1243–1246CrossRefGoogle Scholar
  59. 59.
    Jin QZ, Yue JH, Shan L, Tao GJ, Wang XG, Qiu AY (2008) Process research of macroporous resin chromatography for separation of N-(p-coumaroyl)serotonin and N-feruloylserotonin from Chinese safflower seed extracts. Sep Purif Technol 62:370–375CrossRefGoogle Scholar
  60. 60.
    Kang K, Jang SM, Kang S, Back K (2005) Enhanced neutraceutical serotonin derivatives of rice seed by hydroxycinnamoyl-CoA: serotonin N-(hydroxycinnamoyl) transferase. Plant Sci 168:783–788CrossRefGoogle Scholar
  61. 61.
    Harmatha J, Budĕšínský M, Vokáč K, Pavlík M, Grüner K, Laudová V (2007) Lignan glucosides and serotonin phenylpropanoids from the seeds of Leuzea carthamoides. Collect Czech Chem Commun 72:334–346CrossRefGoogle Scholar
  62. 62.
    Kim EO, Oh JH, Lee SK, Lee JY, Choi SW (2007) Antioxidant properties and quantification of phenolic compounds from safflower (Carthamus tinctorius L.) seeds. Food Sci Biotechnol 16:71–77Google Scholar
  63. 63.
    Ly D, Kang K, Choi JY, Ishihara A, Back K, Lee SG (2008) HPLC analysis of serotonin, tryptamine, tyramine, and the hydroxycinnamic acid amides of serotonin and tyramine in food vegetables. J Med Food 11:385–389CrossRefGoogle Scholar
  64. 64.
    Jang SM, Ishihara A, Back K (2004) Production of coumaroylserotonin and feruloylserotonin in transgenic rice expressing pepper hydroxycinnamoyl-coenzyme a: serotonin N-(hydroxycinnamoyl)transferase. Plant Physiol 135:346–356CrossRefGoogle Scholar
  65. 65.
    Kim EO, Lee JY, Choi SW (2006) Quantitative changes in phenolic compounds of safflower (Carthamus tinctorius L.) seeds during growth and processing. J Food Sci Nutr 11:311–317CrossRefGoogle Scholar
  66. 66.
    Jin QZ, Zou XQ, Shan L, Wang XG, Qiu AY (2010) β-d-Glucosidase-catalyzed deglucosidation of phenylpropanoid amides of 5-hydroxytryptamine glucoside in safflower seed extracts optimized by response surface methodology. J Agric Food Chem 58:155–160CrossRefGoogle Scholar
  67. 67.
    Lee KS, Kim YH, Chung NJ (2008) Determination and isolation of antioxidative serotonin derivatives, N-(p-Coumaroyl)serotonin and N-feruloylserotonin from safflower seeds. Korean J Crop Sci 53:171–178Google Scholar
  68. 68.
    Zhang HL, Nagatsu A, Sakakibara J (1996) Novel antioxidants from safflower (Carthamus tinctorius L.) oil cake. Chem Pharm Bull 44:874–876CrossRefGoogle Scholar
  69. 69.
    Jin QZ (2008) Extraction, purification and biological activities of phenylpropanoid amides of 5-hydroxytryptamine from safflower seeds. PhD thesis, Jiangnan University (in Chinese) Google Scholar
  70. 70.
    Tanaka E, Tanaka C, Mori N, Kuwahara Y, Tsuda M (2003) Phenylpropanoid amides of serotonin accumulate in witches’ broom diseased bamboo. Phytochemistry 64:965–969CrossRefGoogle Scholar
  71. 71.
    Nagatsu A, Zhang H, Mizukami H, Okuyama H, Sakakibara J, Tokuda H, Nishino H (2000) Tyrosinase inhibitory and anti-tumor promoting activities of compounds isolated from safflower (Carthamus tinctorius L.) and cotton (Gossypium hirsutum L.) oil cakes. Nat Prod Lett 14:153–158CrossRefGoogle Scholar
  72. 72.
    Takii T, Kawashima S, Chiba T, Hayashi H, Hayashi M, Hiroma H, Kimura H, Inukai Y, Shibata Y, Nagatsu A, Sakakibara J, Oomoto Y, Hirose K, Onozaki K (2003) Multiple mechanisms involved in the inhibition of proinflammatory cytokine production from human monocytes by N-(p-coumaroyl)serotonin and its derivatives. Int Immunopharmacol 3:273–277CrossRefGoogle Scholar
  73. 73.
    Katsuda S, Suzuki K, Koyama N, Takahashi M, Miyake M, Hazama A, Takazawa K (2009) Safflower seed polyphenols (N-(p-coumaroyl)serotonin and N-feruloylserotonin) ameliorate atherosclerosis and distensibility of the aortic wall in Kurosawa and Kusanagi-hypercholesterolemic (KHC) rabbits. Hypertens Res 32:944–949CrossRefGoogle Scholar
  74. 74.
    Takii T, Hayashi M, Hiroma H, Chiba T, Kawashima S, Zhang HL, Nagatsu A, Sakakibara J, Onozaki K (1999) Serotonin derivative, N-(p-coumaroyl)serotonin, isolated from safflower (Carthamus tinctorius L.) oil cake augments the proliferation of normal human and mouse fibroblasts in synergy with basic fibroblast growth factor (bFGF) or epidermal growth factor (EGF)1. J Biochem 125:910–915CrossRefGoogle Scholar
  75. 75.
    Roh JS, Sun WS, Oh SU, Lee JI, Oh WT, Kim JH (1999) In vitro antioxidant activity of safflower (Carthamus tinctorius L.) seeds. Food Sci Biotechnol 8:88–92Google Scholar
  76. 76.
    Kang GH, Chang EJ, Choi SW (1999) Antioxidative activity of phenolic compounds in roasted safflower (Carthamus tinctorius L.) seeds. J Food Sci Nutr 4:221–225Google Scholar
  77. 77.
    Zhang HL, Nagatsu A, Watanabe T, Sakakibara J, Okuyama H (1997) Antioxidative compounds isolated from safflower (Carthamus tinctorius L.) oil cake. Chem Pharm Bull 45:1910–1914CrossRefGoogle Scholar
  78. 78.
    Zhu JX (2013) Research on the quality change of tea seed oil in oil extraction process. Master thesis, Jiangnan University (in Chinese) Google Scholar
  79. 79.
    Gwatidzo L, Botha BM, McCrindle RI, Combrinck S (2014) Extraction and identification of phytosterols in manketti (Schinziophyton rautanenii) nut oil. J Am Oil Chem Soc 91:783–794CrossRefGoogle Scholar
  80. 80.
    Ramadan MF, Mörsel JT (2002) Neutral lipid classes of black cumin (Nigella sativa L.) seed oils. Eur Food Res Technol 214:202–206CrossRefGoogle Scholar
  81. 81.
    Fauquant C, Briard-Bion V, Leconte N, Guichardant M, Michalski MC (2007) Membrane phospholipids and sterols in microfiltered milk fat globules. Eur J Lipid Sci Technol 109:1167–1173CrossRefGoogle Scholar
  82. 82.
    Li ZX (2015) Impact on trace nutrients and antioxidant activity of camellia seed oil in processing. Master thesis, Jiangnan University (in Chinese) Google Scholar
  83. 83.
    Pronyk C, Abramson D, Muir WE, White NDG (2006) Correlation of total ergosterol levels in stored canola with fungal deterioration. J Stored Prod Res 42:162–172CrossRefGoogle Scholar
  84. 84.
    Kritchevsky D, Chen SC (2005) Phytosterols-health benefits and potential concerns: a review. Nutr Res 25:413–428CrossRefGoogle Scholar
  85. 85.
    Lagarda MJ, García-Llatas G, Farré R (2006) Analysis of phytosterols in foods. J Pharm Biomed Anal 41:1486–1496CrossRefGoogle Scholar
  86. 86.
    Li TSC, Beveridge THJ, Drover JCG (2007) Phytosterol content of sea buckthorn (Hippophae rhamnoides L.) seed oil: extraction and identification. Food Chem 101:1633–1639CrossRefGoogle Scholar
  87. 87.
    Benchekroun K, Bonaly R (1992) Physiological properties and plasma membrane composition of Saccharomyces cerevisiae grown in sequential batch culture and in the presence of surfactants. Appl Microbiol Biotechnol 36:673–678Google Scholar
  88. 88.
    Deng ZL, Yuan JP, Zhang Y, Xu XM, Wu CF, Peng J, Wang JH (2013) Fatty acid composition in ergosteryl esters and triglycerides from the fungus Ganoderma lucidum. J Am Oil Chem Soc 90:1495–1502CrossRefGoogle Scholar
  89. 89.
    Barreira JCM, Oliveira MBPP, Ferreira ICFR (2014) Development of a novel methodology for the analysis of ergosterol in mushrooms. Food Anal Method 7:217–223CrossRefGoogle Scholar
  90. 90.
    Winkler JK, Warner K (2008) Effect of phytosterol structure on thermal polymerization of heated soybean oil. Eur J Lipid Sci Technol 110:1068–1077CrossRefGoogle Scholar
  91. 91.
    He WS, Yin J, Xu HS, Qian QY, Jia CS, Ma HL, Feng B (2014) Efficient synthesis and characterization of ergosterol laurate in a solvent-free system. J Agric Food Chem 62:11748–11755CrossRefGoogle Scholar
  92. 92.
    He WS, Ma Y, Pan XX, Li JJ, Wang MG, Yang YB, Jia CS, Zhang XM, Feng B (2012) Efficient solvent-free synthesis of phytostanyl esters in the presence of acid-surfactant-combined catalyst. J Agric Food Chem 60:9763–9769CrossRefGoogle Scholar
  93. 93.
    As’wad AWM, Sariah M, Paterson RMM, Abidin MAZ, Lima N (2011) Ergosterol analyses of oil palm seedlings and plants infected with Ganoderma. Crop Prot 30:1438–1442CrossRefGoogle Scholar
  94. 94.
    Ruibal-Mendieta NL, Rozenberg R, Delacroix DL, Petitjean G, Dekeyser A, Baccelli C, Marques C, Delzenne NM, Meurens M, Habib-Jiwan JL, Quetin-Leclercq J (2004) Spelt (Triticum spelta L.) and winter wheat (Triticum aestivum L.) wholemeals have similar sterol profiles, as determined by quantitative liquid chromatography and mass spectrometry analysis. J Agric Food Chem 52:4802–4807CrossRefGoogle Scholar
  95. 95.
    Gui B, Shim YY, Datla RSS, Covello PS, Stone SL, Reaney MJT (2012) Identification and quantification of cyclolinopeptides in five flaxseed cultivars. J Agric Food Chem 60:8571–8579CrossRefGoogle Scholar
  96. 96.
    Shim YY, Gui B, Arnison PG, Wang Y, Reaney MJT (2014) Flaxseed (Linum Usitatissimum L.) bioactive compounds and peptide nomenclature: a review. Trends Food Sci Technol 38:5–20CrossRefGoogle Scholar
  97. 97.
    Okinyo-Owiti DP, Young L, Burnett PGG, Reaney MJT (2014) New flaxseed orbitides: detection, sequencing, and 15N incorporation. Pept Sci 102:168–175CrossRefGoogle Scholar
  98. 98.
    Okinyo-Owiti DP, Burnett PGG, Reaney MJT (2014) Simulated moving bed purification of flaxseed oil orbitides: unprecedented separation of cyclolinopeptides C and E. J Chromatogr B 965:231–237CrossRefGoogle Scholar
  99. 99.
    Lao YM, Mackenzie K, Vincent W, Krokhin OV (2014) Characterization and complete separation of major cyclolinopeptides in flaxseed oil by reversed-phase chromatography. J Sep Sci 37:1788–1796CrossRefGoogle Scholar
  100. 100.
    Aladedunye F, Sosinska E, Przybylski R (2013) Flaxseed cyclolinopeptides: analysis and storage stability. J Am Oil Chem Soc 90:419–428CrossRefGoogle Scholar
  101. 101.
    Jadhav PD, Okinyo-Owiti DP, Ahiahonu PWK, Reaney MJT (2013) Detection, isolation and characterisation of cyclolinopeptides J and K in ageing flax. Food Chem 138:1757–1763CrossRefGoogle Scholar
  102. 102.
    Brühl L, Matthäus B, Fehling E, Wiege B, Lehmann B, Luftmann H, Bergander K, Quiroga K, Scheipers A, Frank O, Hofmann T (2007) Identification of bitter off-taste compounds in the stored cold pressed linseed oil. J Agric Food Chem 55:7864–7868CrossRefGoogle Scholar
  103. 103.
    Brühl L, Matthäus B, Scheipers A, Hofmann T (2008) Bitter off-taste in stored cold-pressed linseed oil obtained from different varieties. Eur J Lipid Sci Technol 110:625–631CrossRefGoogle Scholar
  104. 104.
    Bell A, McSteen PM, Cebrat M, Picur B, Siemion IZ (2000) Antimalarial activity of cyclolinopeptide A and its analogues. Acta Pol Pharm 57:134–136Google Scholar
  105. 105.
    Rossi F, Saviano M, Talia PD, Blasio BD, Pedone C, Zanotti G, Mosca M, Saviano G, Tancredi T, Ziegler K, Benedetti E (1996) Solution and solid state structure of an aib-containing cyclodecapeptide inhibiting the cholate uptake in hepatocytes. Pept Sci 40:465–478CrossRefGoogle Scholar
  106. 106.
    Sharav O, Shim YY, Okinyo-Owiti DP, Sammynaiken R, Reaney MJT (2014) Effect of cyclolinopeptides on the oxidative stability of flaxseed oil. J Agric Food Chem 62:88–96CrossRefGoogle Scholar

Copyright information

© AOCS 2015

Authors and Affiliations

  • Jun Jin
    • 1
  • Gayrat Sheraliev
    • 1
    • 2
  • Dan Xie
    • 1
    • 3
  • Wei Zhang
    • 3
  • Qingzhe Jin
    • 1
    Email author
  • Xingguo Wang
    • 1
  1. 1.State Key Laboratory of Food Science and Technology, Synergetic Innovation Center of Food Safety and Nutrition, School of Food Science and TechnologyJiangnan UniversityWuxiPeople’s Republic of China
  2. 2.Tashkent Chemical Technological InstituteTashkentUzbekistan
  3. 3.ZhongHai Ocean (Wuxi) Marine Equipment Engineering Co., Ltd.Jiangnan University National University Science ParkWuxiPeople’s Republic of China

Personalised recommendations