Plant Foods for Human Nutrition

, Volume 62, Issue 3, pp 85–91 | Cite as

Phytosterol, Squalene, Tocopherol Content and Fatty Acid Profile of Selected Seeds, Grains, and Legumes

  • E. Ryan
  • K. Galvin
  • T. P. O’Connor
  • A. R. Maguire
  • N. M. O’Brien
Article

Abstract

The unsaponifiable lipid fraction of plant-based foods is a potential source of bioactive components such as phytosterols, squalene, and tocopherols. The objective of the present study was to determine the levels of phytosterols, and squalene, as well as tocopherols (α and β + γ) in selected grains, seeds, and legumes. The method comprised acid hydrolysis and lipid extraction followed by alkaline saponification, prior to analysis by HPLC. In addition, the fatty acid profile of the foods was determined via total lipid extraction, fatty acid derivitisation and GC analysis. In general, β-sitosterol was the most prevalent phytosterol, ranging in concentration from 24.9 mg/100 g in pumpkin seed to 191.4 mg/100 g in peas. Squalene identified in all foods examined in this study, was particularly abundant in pumpkin seed (89.0 mg/100 g). The sum of α- and β+ γ-tocopherols ranged from 0.1 mg/100 g in rye to 15.9 mg/100 g in pumpkin seeds. Total oil content ranged from 0.9% (w/w) in butter beans to 42.3% (w/w) in pumpkin seed and the type of fat, in all foods examined, was predominantly unsaturated. In conclusion, seeds, grains, and legumes are a rich natural source of phytosterols. Additionally, they contain noticeable amounts of squalene and tocopherols, and in general, their fatty acid profile is favorable.

Keywords

Phytosterols Squalene Tocopherols Seeds Legumes Cereals 

Abbreviations

CHD

coronary heart disease

FAME

fatty acid methyl esters

GC

gas chromatography

HPLC

high performance liquid chromatography

LDL

low-density lipoprotein

MUFA

monounsaturated fatty acids

ND

not detected

NMK

nitrosaminoketone

PUFA

polyunsaturated fatty acids

SCE

sister chromatid exchange

SFA

saturated fatty acids

Tr

trace

Notes

Acknowledgements

This work has been supported by Enterprise Ireland Basic Research Grant.

References

  1. 1.
    Weihrauch JL, Gardner JM (1978) Sterol content of foods of plant origin. J Am Diet Assoc 73:39–44Google Scholar
  2. 2.
    Moreau RA, Whitaker BD, Hicks KB (2002) Phytosterols, phytostanols, and their conjugates in foods: structural diversity, quantitative analysis, and health promoting uses. Prog Lipid Res 41:457–500CrossRefGoogle Scholar
  3. 3.
    de Jong N, Plat J, Mensink RP (2003) Metabolic effects of plant sterols and stanols. J Nutr Biochem 4:362–369Google Scholar
  4. 4.
    Berger A, Jones PJH, Abumweis SS (2004) Plant sterols: factors affecting their efficacy and safety as functional food ingredients. This article is available from:  http://www.lipidworld.com/content/3/1/5
  5. 5.
    Smith TJ (2000) Squalene: potential chemopreventive agent. Expert Opin Invest Drugs 9:1841–1848CrossRefGoogle Scholar
  6. 6.
    Aguilera Y, Dorado ME, Prada FA, Martinez JJ, Quesada A, Ruiz-Gutierrez V (2005) The protective role of squalene in alcohol damage in the chick embryo retina. Exp Eye Res 80:535–543CrossRefGoogle Scholar
  7. 7.
    Senthilkumar S, Devaki T, Manohar BM, Babu MS (2006) Effect of squalene on cyclophosphamide-induced toxicity. Clin Chim Acta 364:335–342CrossRefGoogle Scholar
  8. 8.
    Kohno Y, Egawa Y, Itoh S, Nagaoka S, Takahashi M, Mukai K (1995) Kinetic study of quenching reaction of singlet oxygen and scavenging reaction of free radicals by squalene in n-butanol. Biochem Biophys Acta 1256:52–56Google Scholar
  9. 9.
    O’Sullivan L, Woods JA, O’Brien NM (2002) Squalene but not n-3 fatty acids protect against hydrogen peroxide-induced sister chromatid exchanges in Chinese hamster V79 cells. Nutr Res 22:847–857CrossRefGoogle Scholar
  10. 10.
    Knekt P, Reunanen A, Jarvinen R, Seppanen R, Heliovaara M, Aromaa A (1994) Antioxidant vitamin intake and coronary mortality in a longitudinal population study. Am J Epidemiol 139:1180–1189Google Scholar
  11. 11.
    Kushi LH, Folsom AR, Prineas RJ, Mink PJ, Wu Y, Bostick RM (1996) Dietary antioxidant vitamins and death from coronary heart disease in postmenopausal women. N Engl J Med 330:1029–1035Google Scholar
  12. 12.
    Tucker JM, Townsend DM (2005) Alpha-tocopherol: roles in prevention and therapy of human disease. Biomed Pharmacother 59:380–387CrossRefGoogle Scholar
  13. 13.
    Toivo J, Philips K, Lampi AM, Piironen V (2001) Determination of sterols in foods: Recovery of free, esterified, and glycosidic sterols. J Food Comp Anal 14:631–643CrossRefGoogle Scholar
  14. 14.
    Maguire LS, O’Sullivan SM, Galvin K, O’Connor TP, O’Brien NM (2004) Fatty acid profile, tocopherol, squalene and phytosterol content of walnuts, almonds, peanuts, hazelnuts and the macadamia nut. Int J Food Sci Nutr 55:171–178CrossRefGoogle Scholar
  15. 15.
    Savage GP, McNeill DL, Dutta PC (1997) Lipid composition and oxidative stability of oils in hazelnuts (Corulus avellana L.) grown in New Zealand. J Am Oil Chem Soc 74:755–759CrossRefGoogle Scholar
  16. 16.
    Slover HT, Lanza E (1979) Quantitative analysis of food fatty acids by capillary gas chromatography. J Am Oil Chem Soc 56:933–943CrossRefGoogle Scholar
  17. 17.
    Ostlund RE, Racette SB, Okeke A (2002) Phytosterols that are naturally present in commercial corn oil significantly reduce cholesterol absorption in humans. Am J Clin Nutr 75:1000–1004Google Scholar
  18. 18.
    Andersson SW, Skinner J, Ellegard L, Welch AA, Bingham A, Mulligan A, et al. (2004) Intake of dietary plant sterols is inversely related to serum cholesterol concentration in men and women in the EPIC Norfolk population: a cross-sectional study. Eur J Clin Nutr 58:1378–1385CrossRefGoogle Scholar
  19. 19.
    Philips KM, Ruggio DM, Ashraf-Khorassani M (2005) Phytosterol composition of nuts and seeds commonly consumed in the United States. J Agric Food Chem 53:9436–9445CrossRefGoogle Scholar
  20. 20.
    Piironen V, Toivo J, Puupponen-Pimia R, Lampi AM (2003) Plant sterols in vegetables, fruit and berries. J Food Sci Agric 83:330–337CrossRefGoogle Scholar
  21. 21.
    Normen L, Bryngelsson S, Johnsson M, Evheden P, Ellegard L, Brants H, et al. (2002) The phytosterol content of some cereal foods commonly consumed in Sweden and in the Netherlands. J Food Comp Anal 15:693–704CrossRefGoogle Scholar
  22. 22.
    Morton G, Lee S, Buss D, Lawrance P (1995) Intakes and major dietary sources of cholesterol and phytosterols in the British diet. J Hum Nutr Diet 8:429–440Google Scholar
  23. 23.
    Normen AL, Brants HA, Voorrips LE, Andersson HA, van den Brandt PA, Goldbohm RA (2001) Phytosterol intakes and colorectal cancer risk in the Netherlands cohort study on diet and cancer. Am J Clin Nutr 74:141–148Google Scholar
  24. 24.
    Valsta LM, Lemstrom A, Ovaskainen M-L, Lampi AM, Toivo J, Korhonen T, et al. (2004) Estimation of plant sterol and cholesterol intake in Finland: quality of new values and their effect on intake. Br J Nutr 92:671–678CrossRefGoogle Scholar
  25. 25.
    Berganza BE, Moran AW, Rodriguez G, Coto NM, Santamaria M, Bressani R (2003) Effect of variety and location on the total fat, fatty acids and squalene content of Amaranth. Plant Food Hum Nutr 58:1–6CrossRefGoogle Scholar
  26. 26.
    Martirosyan DM, Miroshnichenko LA, Kulakova SN, Pogojeva AV, Zoloedov VI (2007) Amaranth oil application for coronary heart disease and hypertension. Lipids Health Dis 6:1Google Scholar
  27. 27.
    Liu GCK, Ahrens EH, Schreibman PH, Crouse JR (1976) Measurement of squalene in human tissues and plasma: validation and application. J Lipid Res 17:38–45Google Scholar
  28. 28.
    Fan S, Ho I, Yeoh FL, Lin C, Lee T (1996) Squalene inhibits sodium arsenite-induced sister chromatid exchanges and micronuclei in Chinese hamster ovary-K1 cells. Mutat Res 368:165–169CrossRefGoogle Scholar
  29. 29.
    Kamimara H, Koga N, Oguri K, Yoshimura H (1992) Enhanced elimination of theophylline, phenobarbital and strychnine from the bodies of rats and mice by squalene treatment. J Pharmacobiodyn 15:215–221Google Scholar
  30. 30.
    Richter E, Schafer SG (1982) Effect of squalene on hexachlorobenzene (HCB) concentrations in tissues of mice. J Environ Sci Health B 17:195–203CrossRefGoogle Scholar
  31. 31.
    Rao CV, Newmark HL, Reddy BS (1998) Chemopreventive effect of squalene on colon cancer. Carcinogenesis 19:287–290CrossRefGoogle Scholar
  32. 32.
    Smith TJ, Yang GY, Seril DN, Liao J, Kim S (1998) Inhibition of 4-(methylnitrosamine)-1-(3-pyridyl)-1-butanone-induced tumorogenesis by dietary olive oil and squalene. Carcinogenesis 19:703–706CrossRefGoogle Scholar
  33. 33.
    Eitenmiller RR, Lee J (2004) Vitamin E: food chemistry, composition and analysis. Marcel Decker, New YorkGoogle Scholar
  34. 34.
    Murkovic M, Piironen V, Lampi AM, Kraushofer T, Sontag G (2004) Changes in the chemical composition of pumpkin seeds during the roasting process for production of pumpkin seed oil. Food Chem 84:359–365CrossRefGoogle Scholar
  35. 35.
    Piironen V, Syvaoja EL, Varo P, Salminen K, Koivistoinen P (1986) Tocopherols and tocotrienols in cereal products from Finland. Cereal Chem 63:78–81Google Scholar
  36. 36.
    Wyatt CJ, Carballido SP, Mendez RO (1998) α- and γ-Tocopherol content of selected foods in the Mexican diet. J Agric Food Chem 46:4657–4661CrossRefGoogle Scholar
  37. 37.
    Saldeen K, Saldeen T (2005) Importance of tocopherols beyond α-tocopherol: evidence from animal and human studies. Nutr Res 25:877–889CrossRefGoogle Scholar
  38. 38.
    Chung TY, Nwokolo EN, Sim JS (1989) Compositional and digestibility changes in sprouted barley and canola seeds. Plant Food Hum Nutr 39:267–278CrossRefGoogle Scholar
  39. 39.
    Maatta K, Lampi AM, Petterson J, Fogelfors BM, Piironen V, Kamal-Eldin A (1999) Phytosterol content in seven oat cultivars grown at three locations in Sweden. J Food Sci Agric 79:1021–1027CrossRefGoogle Scholar
  40. 40.
    Marcone MF, Kakuda Y, Yada RY (2004) Amaranth as a rich dietary source of β-sitosterol and other phytosterols. Plant Food Hum Nutr 58:207–211CrossRefGoogle Scholar
  41. 41.
    Zangenberg M, Hansen HB, Jorgensen JR, Hellgren LI (2004) Cultivar and year to year variation of phytosterol content in rye (Secale cereale L). J Agric Food Chem 52:2593–2597CrossRefGoogle Scholar
  42. 42.
    Kalinova J, Triska J, Vrchotova N (2006) Distribution of vitamin E, squalene, epicatechin, and rutin in common buckwheat plants (Fagopyrum esculentum Moench). J Agric Food Chem 54:5330–5335CrossRefGoogle Scholar
  43. 43.
    Zhang H, Vasanthan T, Wettasinghe M (2007) Enrichment of tocopherols and phytosterol in canola oil during seed germination. J Agric Food Chem 55:355–359CrossRefGoogle Scholar
  44. 44.
    Karunanandaa B, Post-Beittenmiller M, Venkatramesh M, Kishore GM, Thorne GM, LeDeaux JR (2004) Transgenic plants containing altered levels of steroid compounds. US patent 6,882,214,2Google Scholar
  45. 45.
    Karunanandaa B, Qi Q, Hao M, Baszis SR, Jensen PK, Wong YH (2005) Metabolically engineered oilseed crops with enhanced seed tocopherol. Metab Eng 7:384–400CrossRefGoogle Scholar
  46. 46.
    Hey SJ, Powers SJ, Beale MH, Hawkins ND, Ward JL, Halford NG (2006) Enhanced seed phytosterol accumulation through expression of a modified HMG-CoA reductase. Plant Biotechnol J 4:219–229CrossRefGoogle Scholar
  47. 47.
    Keys A, Parlin RW (1966) Serum-cholesterol response to changes in dietary lipids. Am J Clin Nutr 19:175–181Google Scholar
  48. 48.
    Lovejoy JC (1999) Dietary fatty acids and insulin resistance. Curr Atheroscler Rep 1:215–220CrossRefGoogle Scholar
  49. 49.
    Hu F, Salmeron J, Manson J, Stampfer M, Colditz G, Rimm E, Willet W (1999) Dietary fat and risk of type 2 diabetes in women. Am J Epidemiol 149:S1Google Scholar
  50. 50.
    Abeywardena MY, McLeannan PL, Charnock JS (1991) Differential effects of dietary fish oil on myocardial prostaglandin 12 and thromboxane A2 production. Am J Physiol 260:379–385Google Scholar
  51. 51.
    Hu FB, Manson JE, Willett WC (2001) Types of dietary fat and risk of coronary heart disease: a critical review. J Am Coll Nutr 20:5–19Google Scholar
  52. 52.
    Watkins TR, Lenz PH, Siderits R, Struck M, Bierenbaum ML (1995) Dietary mustard, rape seed oils and selenium exert distinct effects on serum Se, lipid, peroxidation products and platelet aggregability. J Am Coll Nutr 14(2):176–183Google Scholar

Copyright information

© Springer Science+Business Media, Inc. 2007

Authors and Affiliations

  • E. Ryan
    • 1
  • K. Galvin
    • 1
  • T. P. O’Connor
    • 1
  • A. R. Maguire
    • 2
  • N. M. O’Brien
    • 1
  1. 1.Department of Food and Nutritional SciencesUniversity CollegeCorkIreland
  2. 2.Department of Chemistry and School of Pharmacy, Analytical and Biological Chemistry Research FacilityUniversity CollegeCorkIreland

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