346
Views
16
CrossRef citations to date
0
Altmetric
Invited Article

Guerbet glycolipids from mannose: liquid crystals properties

, , &
Pages 1970-1986 | Received 27 Apr 2018, Published online: 04 Jul 2018

References

  • Hu X, Shi Y, Zhang P, et al. D‐mannose: properties, production, and applications: an overview. Compr Rev Food Sci Food Saf. 2016;15(4):773–785.
  • Mussatto SI, Carneiro LM, Silva JP, et al. A study on chemical constituents and sugars extraction from spent coffee grounds. Carbohydr Polym. 2011;83(2):368–374.
  • Herman RH. Mannose metabolism. I Am J Clin Nutr. 1971;24(4):488–498.
  • Wang B. Chemical characterization and ameliorating effect of polysaccharide from Chinese jujube on intestine oxidative injury by ischemia and reperfusion. Int J Biol Macromol. 2011;48(3):386–391.
  • Aravantinos-Zafiris G, Oreopoulou V, Tzia C, et al. Fibre fraction from orange peel residues after pectin extraction. LWT-Food Sci Technol. 1994;27(5):468–471.
  • Yashoda H, Prabha T, Tharanathan R. Mango ripening–role of carbohydrases in tissue softening. Food Chem. 2007;102(3):691–698.
  • Vicariotto F. Effectiveness of an association of a cranberry dry extract, D-mannose, and the two microorganisms Lactobacillus plantarum LP01 and Lactobacillus paracasei LPC09 in women affected by cystitis: a pilot study. J Clin Gastroenterol. 2014;48:S96–S101.
  • Toyota S, Fukushi Y, Katoh S, et al. Anti-bacterial defense mechanism of the urinary bladder. Role of mannose in urine. Nihon Hinyokika Gakkai Zasshi. 1989;80(12):1816–1823.
  • Robyt J. Essentials of carbohydrate chemistry. Berlin: Springer; 1998.
  • Niehues R, Hasilik M, Alton G, et al. Carbohydrate-deficient glycoprotein syndrome type Ib. Phosphomannose isomerase deficiency and mannose therapy. J Clin Invest. 1998;101(7):1414–1420.
  • Bayach I, Manickam Achari V, Wan Iskandar WFN, et al. Computational insights into octyl-D-xyloside isomers towards understanding the liquid crystalline structure: physico-chemical features. Liq Cryst. 2016;43(10):1503–1513.
  • Mosapour Kotena Z, Behjatmanesh–Ardakani R, Hashim R. AIM and NBO analyses on hydrogen bonds formation in sugar-based surfactants (α/β-D-mannose and n-octyl-α/βD-mannopyranoside): a density functional theory study. Liq Cryst. 2014;41(6):784–792.
  • Chong TT, Heidelberg T, Hashim R, et al. Computer modelling and simulations of thermotropic and lyotropic alkyl glycoside bilayers. Liq Cryst. 2007;34(3):349–363.
  • Manickam Achari V, Bryce RA, Hashim R. Conformational dynamics of dry lamellar crystals of sugar based lipids: an atomistic simulation study. PLOS ONE. 2014;9(6):e101110.
  • Vill V, Hashim R. Carbohydrate liquid crystals: structure-property relationship of thermotropic and lyotropic glycolipids. Curr Opin Colloid Interface Sci. 2002;7(5–6):395–409.
  • Cheung DL, Clark SJ, Wilson MR. Calculation of the rotational viscosity of a nematic liquid crystal. Chem Phys Lett. 2002;356(1–2):140–146.
  • Tiberio G, Muccioli L, Berardi R, et al. Towards in silico liquid crystals. realistic transition temperatures and physical properties for n‐cyanobiphenyls via molecular dynamics simulations. Chem Phys Chem. 2009;10(1):125–136.
  • Goodby JW, Pfannemüller B, Welte W, et al. Liquid‐crystalline glycolipids: towards understanding the roles of liquid crystals in biological and life processes. Liq Cryst. 2006;33(11–12):1229–1245.
  • Hashim R, Sugimura A, Minamikawa H, et al. Nature-like synthetic alkyl branched-chain glycolipids: a review on chemical structure and self-assembly properties. Liq Cryst. 2011;39(1):1–17.
  • Shah JC, Sadhale Y, Chilukuri DM. Cubic phase gels as drug delivery systems. Adv Drug Deliv Rev. 2001;47(2–3):229–250.
  • Borshchevskiy V, Moiseeva E, Kuklin A, et al. Isoprenoid-chained lipid β-xyloC16+4–a novel molecule for in meso membrane protein crystallization. J Cryst Growth. 2010;312(22):3326–3330.
  • MarketsandMarkets. Surfactants Market. http://www.marketsandmarkets.com/PressReleases/surfactants.asp2015 [cited 2015 Oct 28].
  • Yang Z, Xu R, Ali-Rachedi F, et al. Liquid crystalline glycosteroids and acyl steroid glycosides (ASG). Liq Cryst. 2017;44(12–13):2089–2107.
  • Mannock DA, McElhaney RN. Thermotropic and lyotropic phase properties of glycolipid diastereomers: role of headgroup and interfacial interactions in determining phase behaviour. Curr Opin Colloid Interface Sci. 2004;8(6):426–447.
  • Von Minden HM, Brandenburg K, Seydel U, et al. Thermotropic and lyotropic properties of long chain alkyl glycopyranosides. Part II. Disaccharide headgroups. Chem Phys Lipids. 2000;106(2):157–179.
  • Vill V, Von Minden HM, Koch MHJ, et al. Thermotropic and lyotropic properties of long chain alkyl glycopyranosides: part I: monosaccharide headgroups. Chem Phys Lipids. 2000;104(1):75–91.
  • Minamikawa H, Murakami T, Hato M. Synthesis of 1,3-di-O-alkyl-2-O-(β-glycosyl)glycerols bearing oligosaccharides as hydrophilic groups. Chem Phys Lipids. 1994;72(2):111–118.
  • Velayutham TS, Ng BK, Gan WC, et al. Phase sensitive molecular dynamics of self-assembly glycolipid thin films: a dielectric spectroscopy investigation. J Chem Phys. 2014;141(8):085101.
  • Velayutham TS, Nguan HS, Ng BK, et al. Molecular dynamics of anhydrous glycolipid self-assembly in lamellar and hexagonal phases. Phys Chem Chem Phys. 2016;18(22):15182–15190.
  • Liao G, Zewe SK, Hagerty J, et al. Thermotropic liquid crystalline properties of amphiphilic branched chain glycolipids. Liq Cryst. 2006;33(3):361–366.
  • Abeygunaratne S, Hashim R, Vill V. Evidence for uncorrelated tilted layer structure and electrically polarized bilayers in amphiphilic glycolipids. Phys Rev E. 2006;73(1):011916.
  • Vill V, Fischer F, Thiem J. Helical twisting power of carbohydrate derivatives. Z Naturforsch. 1988;43a:1119–1126.
  • Von Minden HM, Milkereit G, Vill V. Effects of carbohydrate headgroups on the stability of induced cubic phases in binary mixtures of glycolipids. Chem Phys Lipids. 2002;120(1–2):45–56.
  • Gurtovenko AA, Vattulainen I. Molecular mechanism for lipid flip-flops. J Phys Chem B. 2007;111(48):13554–13559.
  • Narain A, Asawa S, Chhabria V, et al. Cell membrane coated nanoparticles: next-generation therapeutics. Nanomedicine. 2017;12(21):2677–2692.
  • Carmona-Ribeiro AM. Lipid-based biomimetics in drug and vaccine delivery. In: Mukherjee A, editor. Biomimetics learning from nature. Rijeka: InTech; 2010. p. Ch. 25.
  • Balzer D, Luders H, editors. Nonionic surfactants: alkyl polyglucosides. New York: Marcel Dekker Inc.; 2000.
  • Guerbet M. Condensation de l’alcool isopropylique avec son dérivé sodé; formation du méthylisobutylcarbinol et du diméthyl-2.4-heptanol-6. Comptes Rendus Acad Sci. 1909;149:129–132.
  • Knothe G. Synthesis, applications, and characterization of Guerbet compounds and their derivatives. Lipid Technol. 2002;14:101–104.
  • Claesson P, Stubenrausch C, Krustev R, et al. Thin film and foam properties of sugar-based surfactants. In: Ruiz CC, editor. Sugar-based surfactants: fundamentals and applications. United State of America: CRC Press; 2008. p. 144.
  • Hashim R, Hashim HHA, Rodzi NZM, et al. Branched chain glycosides: enhanced diversity for phase behavior of easily accessible synthetic glycolipids. Thin Solid Films. 2006;509(1–2):27–35.
  • Zahid NI, Conn CE, Brooks NJ, et al. Investigation of the effect of sugar stereochemistry on biologically relevant lyotropic phases from branched-chain synthetic glycolipids by small-angle X-ray scattering. Langmuir. 2013;29(51):15794–15804.
  • Liew CY, Salim M, Zahid NI, et al. Biomass derived xylose Guerbet surfactants: thermotropic and lyotropic properties from small-angle X-ray scattering. RSC Adv. 2015;5(120):99125–99132.
  • Israelachvili JN. Intermolecular and surface forces. 2nd ed. London: Academic Press; 1991.
  • Hato M, Yamashita J, Shiono M. Aqueous phase behavior of lipids with isoprenoid type hydrophobic chains. J Phys Chem B. 2009;113(30):10196–10209.
  • Shearman GC, Khoo BJ, Motherwell M-L, et al. Calculations of and evidence for chain packing stress in inverse lyotropic bicontinuous cubic phases. Langmuir. 2007;23(13):7276–7285.
  • Brooks NJ, Hamid HA, Hashim R, et al. Thermotropic and lyotropic liquid crystalline phases of Guerbet branched-chain-D-glucosides. Liq Cryst. 2011;38(11–12):1725–1734.
  • Polakova M, Belanova M, Petrus L, et al. Synthesis of alkyl and cycloalkyl α-D-mannopyranosides and derivatives thereof and their evaluation in the mycobacterial mannosyltransferase assay. Carbohydr Res. 2010;345:1339–1347.
  • Loewenstein A, Igner D. Deuterium NMR studies of n-octyl α and β–glucopyranoside liquid-crystalline srystems. Liq Cryst. 1991;10(4):457–466.
  • Vill V, Böcker T, Thiem J, et al. Studies on liquid-crystalline glycosides. Liq Cryst. 1989;6(3):349–356.
  • Hashim R, Zahid NI, Velayutham TS, et al. Dry thermotropic glycolipid self-assembly: a review. J Oleo Sci. 2018;67(6):651–668.
  • Ogawa S, Asakura K, Osanai S. Thermotropic and glass transition behaviors of n-alkyl β-D-glucosides. RSC Adv. 2013;3(44):21439–21446.
  • Ogawa S. Phase behavior of n-alkyl glucosides in the arid system—recent developments and experimental notes. In: Boyd I, editor. Glucosides, sources, applications, and new research. United State of America: Nova Science Publishers, Inc.; 2017. p. 63.
  • Wunderlich B, Boller A, Okazaki I, et al. Heat-capacity determination by temperature-modulated DSC and its separation from transition effects. Thermochim Acta. 1997;304:125–136.
  • Atkins PW, Atkins PW. The elements of physical chemistry. Vol. 496. United Kingdom: Oxford University Press; 1992.
  • Tenchov B. On the reversibility of the phase transitions in lipid-water systems. Chem Phys Lipids. 1991;57(2–3):165–177.
  • Rappolt M, Rapp G. Structure of the stable and metastable ripple phase of dipalmitoylphosphatidylcholine. Eur Biophys J. 1996;24(6):381–386.
  • The authors thank Dr. Charlotte E Conn, Dr. Nigel Kirby, Dr. Stephen Mudie, and Dr. Adrian Hawley at the Australian Synchrotron for their assistance with SAXS experiments.
  • Elouatib A, Gors C, Fouret R. Metastable phases in kinetics of phase transformations in the frozen liquid crystal 4-ethoxybenzylidene-4′-n-butylaniline. Liq Cryst. 1991;9(4):539–550.
  • Fouret R, Elouatib A, Gors C, et al. Metastable phases and kinetics of phase transformations in quenched liquid crystals. Ph Transit. 1991;33(1–4):209–225.
  • Chung H, Caffrey M. The curvature elastic-energy function of the lipid-water cubic mesophase. Nature. 1994;368(6468):224–226.
  • Seddon JM, Squires AM, Conn CE, et al. Pressure-jump X-ray studies of liquid crystal transitions in lipids. Philos Trans Royal Soc A 2006. 2006;364(1847):2635–2655.
  • Hyde ST. Bicontinuous structures in lyotropic liquid crystals and crystalline hyperbolic surfaces. Curr Opin Solid State Mater Sci. 1996;1(5):653–662.
  • Salim M, Zahid NI, Liew CY, et al. Cubosome particles of a novel Guerbet branched chain glycolipid. Liq Cryst. 2016;43(2):168–174.
  • Radiman S, Toprakcioglu C, McLeish T. Rheological study of ternary cubic phases. Langmuir. 1994;10(1):61–67.
  • Tiddy GJT. Surfactant-water liquid crystal phases. Phys Rep. 1980;57(1):1–46.
  • Ahmadi S, Manickam Achari V, Hussain Z, et al. Epimeric and anomeric relationship of octyl-α-D-gluco/galactosides: insight from density functional theory and atom in molecules studies. Comput Theor Chem. 2017;1108:93–102.
  • Seddon JM. Structure of the inverted hexagonal (HII) phase, and non-lamellar phase transitions of lipids. Biochim Biophys Acta. 1990;1031(1):1–69.
  • Stubenrauch C. Sugar surfactants–aggregation, interfacial, and adsorption phenomena. Curr Opin Colloid Interface Sci. 2001;6(2):160–170.
  • Production of manna in Sicily 2006 [cited 2018 Mar]. Available from: http://www.oleaceae.info/fraxinus/manna.html
  • Rodzi N Branched chain galactosides and melibiosides: synthesis and mesomorphic properties. MSc. Dissertation University of Malaya: Kuala Lumpur. 2006.
  • Hashim R, Mirzadeh SM, Heidelberg T, et al. A reevaluation of the epimeric and anomeric relationship of glucosides and galactosides in thermotropic liquid crystal self-assemblies. Carbohydr Res. 2011;346(18):2948–2956.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.