Extraction limitations of functional native products: Bioactive lipids chemically modified;Limitations extractives des ingrédients fonctionnels natifs: Lipides bioactifs par modifications chimiques

OCL - Oleagineux Corps Gras Lipides

Volumn 13, Issue 1, 2006, Pages 16-22

  Mouloungui, Zéphirin ^a   Roche, Jane ^a   Bouniols, Andrée ^a  

^a UNIVERSITÉ DE TOULOUSE   (France)

Author keywords

Chemical modification; Industrial application; Lipids; Phytosterols

Indexed keywords

EID: 33746238200     PISSN: 12588210     EISSN: None     Source Type: Journal    
DOI: 10.1051/ocl.2006.0016     Document Type: Review

References (56)

1. MIETTINEN TA, TILVIS RS, KESANIEMI YA. Serum plant sterols and cholesterol precursors reflect cholesterol absorption and synthesis in volunteers of a randomly selected male population. Am J Epidemiol 1990; 131: 20-31.
2. PELLETIER X, et al. A diet moderately enriched in phytosterols lowers plasma cholesterol concentrations in normo-cholesterolemic human. Annal of Nutr and Metab 1995; 39: 291-5.
3. BOSNER MS, LANG LG, STENSON WF, OSLUND JRRE. Percent cholesterol absorption in normal women and men quantified with dual stable isotopic tracers and negative ion mass spectrometry. J Lipid Res 1999; 40: 302-8.
4. OSTLUND JRRE, et al. Gastrointestinal absorption and plasma kinetics of soy-Delta (5)-phytosterols and phytostanols in humans. Am J Physiol Endocrinol Metab 2002; 282: E911-E916.
5. BERGER A, JONES PJH, ABUMWEIS SS. Plants sterols: factors affecting their efficacy and safety as functional food ingredients. Lipids Health Dis 2004: 3-5.
6. MOREAU R, WHITAKER BD, HICKS KB. Phytosterol, phytostanols, and their conjugates in foods: structural diversity, quantitative analysis, and health-promoting uses. Prog Lipid Res 2002; 41: 457-500.
7. VAN DANSIK P. Phytosterols. In: Proc. of the final conference CTVO-net, Bonn (Germany). 2000: 149-80.
8. FOLMER BM. Sterol surfactants: from synthesis to applications. Adv Colloid Interface Sci 2003; 103: 99-109.
9. DAGUET, COÏC JP. Phytosterols extraction: state of the art. OCL 1999; 6: 25-8.
10. PIIRONEN V, TOIVO J, LAMPI AM. Plants sterols: biosynthesis, biological function and their importance to human nutrition. J Food Compos Anal 2000; 12: 619-24.
11. KARLESKIND A. Oils and Fats Manual. Paris: Lavoisier Publishing, 1992: 323; (Vol. 1-1).
12. PHILLIPS KM, RUGGIO DM, TOIVO JI, SWANK MA, SIMPKINS AH. Free and esterified composition of edible oils and fats. J Food Compos Anal 2002; 15: 123-42.
13. ROCHE J. Thèse, Institut National Polytechnique de Toulouse, Toulouse (FR). Composition de la graine de tournesol (Helianthus annuus L.) sous l'effet conjugué des contraintes agri-environnementales et des potentiels variétaux. 2005: 298.
14. VENKETESHEWER RAO A, JANEZIC SA. The role of dietary phytostérols in colon carcinogenesis. Nutr Cancer 1992; 18: 44-52.
15. VLAHAKIS C, HAZEBROEK J. Phytosterol accumulation in canola, sunflower, and soybean oils: effects of genetics, planting location, and temperature. JAOCS 2000; 77: 49-53.
16. WESTER I. Cholesterol lowering effect of plant sterols. Eur J Lipid Sci Technol 2000: 37-44.
17. DE JONG I, PLAT J, MENSINK RP. Metabolic effects of plant sterols and stanols (review). J Nutr Biochem 2003; 14: 362-9.
18. SUGANO WJ, KAMO I, IKEDA I, MORIOKO H. Lipid-lowering activity of phytostanols in rats. Atherosclerosis 1976; 24: 301-9.
19. HEINEMANN T, KULLACK-UBLICK GA, PIETRUCK B, VON BERGMANN K. Mechanisms of action of plant sterols on inhibition of cholesterol absorption. Comparison of sitosterol and sitostanol. Eur J Clin Pharmacol 1991; 40: 59-63.
20. GRUNDY SM, MOK HYI. Optimizing the effect on cholesterol absorption in man. J Lipid Res 1997; 18: 263-71.
21. NIGON F, SERFATY-LACROSNIERE C, CHAUVOIS D, NEVEU C, CHAPMAN J, BRUCKERT E. Les phytostérols: une nouvelle approche diététique de l'hypercholésterolémie. STV 2000; 12: 483-90.
22. QUILES JL, HUERTAS JR, OCHOA JJ, BATTINO M, MATAIX J, MANAS M. Dietary fat (virgin olive oil or sunflower oil) and physical training interactions on blood lipids in the rat. Nutrition 2003; 19: 363-8.
23. LAW MR, WALD NJ, THOMPSON SG. By how much and how quickly does reduction in serum cholesterol concentration lower risk of ischaemic heart disease? BMJ 1994; 308: 367-72.
24. AWAD AB, ROY R, FINK CS. Beta-sitosterol, a plant sterol induces apoptosis and activates key caspases in MDA-MB-231 human breast cancer cells. On Col Rep 2003; 10: 497-500.
25. TAPIERO H, TOWNSEND DM, TEW KD. Phytosterols in the prevention of human pathologies. Biomed Pharmacother 2003; 57: 321-5.
26. MOGHADASIAN MH, MCMANUS BM, PRITCHARD PH, FROHLICH JJ. "Tall oil"-derived phytosterols reduce antherosclerosis in ApoE-deficient mice. Anterioscler Thromb Vasc 1997; 17: 119-26.
27. MOGHADASIAN MH, MCMANUS BM, GODIN DV, RODRIGUES B, FROHLICH JJ. Proatherogenic and antiatherogenic effects of probucol and phytosterols in apolipoprotein E-deficient mice: possible mechanisms of action. Circulation 1999: 1733-9.
28. BOUIC PJ. The role of phytosterols and phytosterolins in immune modulation: a review of the past 10 years. Curr Opin Clin Nutr Metab Care 2001; 4: 471-5.
29. VAN RENSBURGET SJ, DANIELS WM, VAN ZYL JM, TALJJARD JJ. A comparative study of the effects of cholesterol, beta-sitosterol, beta-sitosterol glucoside, dehydroepiandrosterone, sulphate and melatonin on in vitro lipid peroxidation. Metab Brain Dis 2000; 15: 257-65.
30. FOLMER BM, SVENSSON M, HOLMBERG K, BROWN W. The physicochemical behavior of phytosterol ethoxylation. J Colloid Interface Sci 1999; 213: 112-20.
31. URATA K, TAKAISHI N. Cholesterol as synthetic building blocks for artificial lipids with characteristic physical, chemical and biological properties. Eur J Lipid Sci Technol 2001; 103: 29-39.
32. URATA K, TAKAISHI N. Cholesteryl ester compounds containing alkyl branched acyl groups - their preparations, properties and applications. Fett/Lipid 1997; 99: 327-32.
33. TAKAISHI N, URATA K, INAMOTO Y, OKAMOTO K, TSUCHIYA S. Branched fatty acids cholesteryl esters and cosmetic composition containing the same. US Pat. No. 4309448 Kao Corp; 1982.
34. GOKEL GW, HERNANDEZ JC, VISCARIELLO AM, et al. Steroidal lariat ethers: a new class of macrocycles and the crystal structure of N-(cholesteryloxy- carbonyl)aza-15-crown-5. J Org Chem 1987; 52: 2963-8.
35. HE GX, WADA F, KIKUKAWA K, SHINKAI S, MATSUDA TJ. Syntheses and thermal properties of new liquid crystals bearing a crown ether ring: cation binding in the nematic ohase. J Org Chem 1990; 55: 541-8.
36. SHINKAI S, NISHI T, MATSUDA TJ. Chirality recognition by a color change in crowned cholesteric liquid crystals. Chem Lett (Jpn) 1991: 437-40.
37. JUN Q, MING-GUI X, ZI-LUN H, HUA-MING Z. Synthesis of amicyclic crown ether liquid crystals. Synth Commun 1992: 2253-8.
38. NAGVEKAR DS, DELAVIZ Y, PRASAD A, MEROLA H, MARAND H, GIBSON HW. Synthesis and properties of cholesteryl esters bearing 32- and 16-membered crown ethers. J Org Chem 1996; 61: 1211-8.
39. ZHANG JH, BAZUIN CG, FREIBERG S, BRISSE F, ZHU XX. Effect of side chain structure on the liquid crystalline properties of polymers bearing cholesterol, dihydrocholesterol and bile acid pendant groups. Polym 2005; 46: 7266-72.
40. GEORGE M, DAS S. Nonlinear optical properties of some cholesterol based liquid crystals. Chem Lett (Jpn) 1999: 1081 -2.
41. YELAMAGGARD CV, HIREMATH US, SHANKAR RAODS, PRASAD SK. A novel calamitic liquid crystalline oligomer composed of three non-identical mesogenic entities: synthesis and characterization. Chem Commun 2000: 57-8.
42. FASBENDER AJ, WELSH CS, SIEGEL CS, et al. Compositions comprising cationic amphiphiles and co-lipids for intracellular delivery of therapeutic molecules. WO Pat. No. 97/46223 Genzyme Corp. 1997.
43. SIEGEL CS, HARRIS DJ, LEE SC, et al. Cationic amphiphiles containing steroid lipophilic groups for intracellular delivery of therapeutic molecules. US Pat. No. 5747471 Genzyme Corp. 1998.
44. SIEGEL CS, HARRIS DJ, LEE SC, et al. New N-spermidine cholesteryl carbamate cationic amphiphiles for facilitating the delivery of biologically active molecules into cells. US Pat. No. 5783565 Genzyme Corp. 1998.
45. SIEGEL CS, HARRIS DJ, LEE SC, et al. New cationic amphiphiles compounds used for facilitating transport of biologically active molecules into cells. Particularly for gene therapy. US Pat. No. 5910487 Genzyme Corp. 1999.
46. GEALL AJ, TAYLOR RJ, EARLL ME, EATON MAW, BLAGBROUGH IS. Synthesis of cholesterol-polyamine carbamates: pKa studies and condensation of calf thymus DNA. Chem Commun 1998: 1400-4.
47. COOPER RG, et al. Polyamine analogues of 3β-[N- (N′,N′- Dimethylaminoethane) carbamoyl]-Cholesterol (DC-Chol) as agents for gene delivery. Chem Eur J 1998; 4: 134-51.
48. HELMUT R, GEORG D, NORBERT M, ULRICH S, VOLKER R. Polymerizable liquid crystalline monomers and dental materials based thereon. EP 0754675 Ivoclar AG. 1997.
49. TAJIMA K, AIDA T. Controlled polymerizations with constrained geometries. Chem Commun 2000: 2399-412.
50. e Congrès de l'ACFAS. 1998: 209.
51. ROCHE J, et al. Diversified composition of sunflower (Helianthus annuus L.) seeds within cultural practices and genotypes (hybrids and populations). Helia 2004; 27(40): 73-98.
52. ROCHE J, BOUNIOLS A, MOULOUNGUI Z, BARRANCO T, CERNY M. Management of environmental crop conditions to produce useful sunflower-oil components. Eur J Lipid Sci Technol 2006. Sous-presse.
53. MOULOUNGUI Z, MECHLING E. Method for preparing fatty acids by hydrolysing in situ lipids contained in a plant seeds. WO Pat. No. 2004/022677, R28L3970/17/02/2006.
54. MOULOUNGUI Z, TRUONG-DINH NG, MARECHAL P. Polycarbonate de glycérol. Compositions organiques le contenant. Procédé d'obtention de ces compositions organiques et procédé d'extraction du polycarbonate de glycérol et leurs applications. PCT/FR05/02065 (10/08/2005), FR 0408796 (10/08/2004) (WO 2006/021676/02/03/2006)
55. MOULOUNGUI Z. Voies inhabituelles de synthèse de composés oléophiles à partir des substrats végétaux solides (graines oléoprotéagineuses), liquides (huiles végétales et dérivés, glycérol) par l'industrie chimique. OCL 2004; 11(6): 425-35.
56. MOULOUNGUI Z, PELET S. Study of the acyl transfer reaction: structure and properties of glycerol carbonate esters. Eur J Lipid Sci Technol 2001; 103: 216-22.