Polar Lipids: Phospholipids and Glycolipids
Edible Oil and Fat Products: Chemistry, Properties, and Safety Aspects
Moghis U. Ahmad,
Shoukath M. Ali,
Ateeq Ahmad, Saifuddin Sheikh,
Paul Chen, Imran Ahmad,
Moghis U. Ahmad
Jina Pharmaceuticals Inc., Libertyville, IL, USA
Search for more papers by this authorShoukath M. Ali
Jina Pharmaceuticals Inc., Libertyville, IL, USA
Search for more papers by this authorSaifuddin Sheikh
Jina Pharmaceuticals Inc., Libertyville, IL, USA
Search for more papers by this authorMoghis U. Ahmad,
Shoukath M. Ali,
Ateeq Ahmad, Saifuddin Sheikh,
Paul Chen, Imran Ahmad,
Moghis U. Ahmad
Jina Pharmaceuticals Inc., Libertyville, IL, USA
Search for more papers by this authorShoukath M. Ali
Jina Pharmaceuticals Inc., Libertyville, IL, USA
Search for more papers by this authorSaifuddin Sheikh
Jina Pharmaceuticals Inc., Libertyville, IL, USA
Search for more papers by this authorAbstract
Nature was remarkably inventive in creating the variety of polar lipids that form the matrix of biological membranes. Both phospholipids and glycolipids are polar lipids and are important constituents of natural membranes. Typically found on the outer surface of cellular membranes, glycolipids maintain the stability of the membrane, facilitate cellular regulation, and enable cell-to-cell communication. Phospholipids are the major lipid constituent in cell membrane, thus maintaining the structural integrity between the cell and its environment and providing boundaries between compartments within the cell. Phospholipids have many functions in biological systems, including as fuels, as membrane structural elements, as signaling agents, and as surfactants. As main components of the cellular membrane, phospholipids have excellent biocompatibility and amphiphilicity. These unique properties make phospholipids most appropriate to be employed as important pharmaceutical excipients, and they have a very wide range of applications in drug delivery systems. In addition, phospholipids are widely used in food, feed, agriculture, cosmetics, and chemical industries. This article focuses on the basic chemistry, sources, synthesis, physical and analytical chemistry, and applications of phospholipids and glycolipids.
References
- 1 F.D. Gunstone (ed.) (2008). Phospholipid Technology and Applications, 1–16. London: Elsevier.
- 2Scholey, A.B., Camfield, D.A., Hughes, M.E. et al. (2013). Trials 14: 404.
- 3Buccoliero, R. and Futerman, A.H. (2003). Pharmacol. Res. 47: 409–419.
- 4Kolter, T. (2011). Chem. Phys. Lipids 164: 590–606.
- 5Li, J., Wang, X., Zhang, T. et al. (2015). Asian J. Pharmaceut. Sci. 10: 81–98.
- 6Hoogevest, P.V. and Wendel, A. (2014). Eur. J. Lipid Sci. Technol. 116: 1088–1107.
- 7Baer, E. and Pavanaram, S.K. (1961). J. Biol. Chem. 236 (5): 1269–1272.
- 8Paltauf, F. and Hermetter, A. (1990). Phospholipids, 1–12. Springer.
10.1007/978-1-4757-1364-0_1 Google Scholar
- 9Stafford, R.E. and Dennis, E.A. (1987). Colloids Surf. 30 (1): 47–64.
10.1016/0166-6622(87)80203-2 Google Scholar
- 10McIntosh, T.J., Simon, S.A., and Needham, D. (1992). Biochemistry 31: 2012–2020.
- 11Barenholz, Y. and Thompson, T.E. (1999). Chem. Phys. Lipids 102: 29–34.
- 12Gobley, T. (1846). J. Depharm. Chem., 3rd series (in French) 9: 81–91.
- 13Gobley, T. (1850). J. Depharm. Chem. 3rd series (in French) 17: 401–430.
- 14Gobley, T. (1874). J. Depharm. Chem. 4th series (in French) 19: 346–353.
- 15Hager, A., De Paoli, T., and Ihlo, J. (1993). Spectrochim. Acta A 49: 1999–2005.
- 16Rossi, M. (2007). Bioactive Egg Compounds, 229–239. Springer.
10.1007/978-3-540-37885-3_27 Google Scholar
- 17Terao, J., Hirota, Y., and Kawalatsu, M. (1981). Lipids 16: 427–432.
- 18Wiesehahn, G.A. (1937). Oil Soap 14: 119–122.
- 19Eichberg, J. (1939). Oil Soap 16: 51–53.
- 20Wittcoff, H. (1951). The Phosphatides. AOCS Monograph No. 112. New York: Reinhold.
- 21Orthoefer, F.T. and List, G.R. (2006). In: Nutraceutical and Specialty Lipids and Their Co-products (ed. F. Shahidi), 509–530. Boca Raton, FL: CRC/Taylor & Francis.
- 22Schneider, M. (2008). In: Phospholipids Technology and Applications (ed. F.D. Gunstone), 21–40. Bridgewater: Oily Press.
- 23List, G.R. (2015). In: Polar Lipids: Biology, Chemistry, and Technology (ed. M. Ahmad and X.B. Xu), 1–33. AOCS Press.
10.1016/B978-1-63067-044-3.50005-4 Google Scholar
- 24Van Nieuwenhuyzen, W. (2014). INFORM 25: 254–259.
- 25List, G.R., Orthoefer, F.T., Taylor, N. et al. (1999). J. Am. Oil Chem. Soc. 76: 57–66.
- 26Liu, D. and Ma, F. (2011). In: Recent Trends for Enhancing the Diversity and Quality of Soybean Products (ed. D. Krezhove) Chapter 22, 483–500.
- 27Palacios, L.E. and Wang, T. (2005). J. Am. Oil Chem. Soc. 82: 571–578.
- 28Burri, L., Hoem, N., Banni, S., and Berge, K. (2012). Int. J. Mol. Sci. 13: 15401–15419.
- 29Yamamoto, Y., Mizuto, E., Ito, M. et al. (2014). J. Oleo. Sci. 63: 1275–1281.
- 30Decsi, T. and Koletzko, B. (2005). Curr. Opin. Clin. Nutr. Metab. Care 8: 161–166.
- 31Guinot, D., Monroig, O., Hontoria, F. et al. (2013). Aquaculture 412/413: 173–178.
- 32Mangano, K.M., Sahni, S., Kerstetter, J.E. et al. (2013). Curr. Osteoporos. Res. 11: 203–212.
- 33Sedlmeier, E.M., Brunner, S., Much, D. et al. (2014). BMC Genom. 15: 941–960.
- 34Lemaitre-Delaunay, D., Pachiaudi, C., Laville, M. et al. (1999). J. Lipid Res. 40: 1867–1874.
- 35Galli, C., Sirtori, C.R., Mosconi, C. et al. (1992). Lipids 27: 1005–1012.
- 36Wijendran, V., Huang, M.C., Diau, G.Y. et al. (2002). Pediatr. Res. 51: 265–272.
- 37Haraldsson, G.G. and Thorarensen, A. (1999). J. Am. Oil Chem. Soc. 76: 1143–1149.
- 38Lauritizen, L., Hansen, H.S., Jørgensen, M.H., and Michaelsen, K.F. (2001). Prog. Lipid Res. 40: 1–94.
- 39Tam, O. and Innis, S.M. (2006). Dev. Neurosci. 28: 222–229.
- 40Lippmeier, J.C., Crawford, K.S., Owen, C.B. et al. (2009). Lipid 44: 621–630.
- 41Zhang, K. (2015). In: Polar Lipids: Biology, Chemistry, and Technology (ed. M. Ahmad and X.B. Xu), 463–493. AOCS Press.
10.1016/B978-1-63067-044-3.50018-2 Google Scholar
- 42Goh, S.H., Khor, H.T., and Gee, P.T. (1982). J. Am. Oil Chem. Soc. 59: 296–299.
- 43Choo, Y.M., Bong, S.C., Ma, A.N., and Chuah, C.H. (2004). J. Am. Oil Chem. Soc. 81: 471–475.
- 44Schneider, M. (2001). Eur. J. Lipid Sci. Technol. 103: 98–101.
- 45Guo, Z., Vikberg, A.F., and Xu, X. (2005). Biotechnol. Adv. 23: 203–259.
- 46Knuiman, J., Beynen, A., and Katan, M. (1989). Am. J. Clin. Nutr. 49: 266–270.
- 47Lieber, C., De Carli, K., Mak, K. et al. (1990). Hepatology 12: 1390–1398.
- 48Pepeu, G., Pepeu, L., and Amaducci, L. (1996). Pharmacol. Res. 33: 73–80.
- 49Koletzko, I., Edenhofer, S., Lipowsky, G., and Reinhardt, D. (1995). J. Pediatr. Gastroenterol. Nutr. 21: 200–208.
- 50Wilson, T., Mescervey, C., and Nicolosi, R. (1998). Atherosclerosis 140: 147–153.
- 51Haslenda, H. and Jamaluddin, M.Z. (2011). Resour. Conserv. Recycl. 55: 713–718.
- 52Gobi, K. and Vadivelu, V.M. (2013). Renew. Sust. Energ. Rev. 28: 788–803.
- 53Cheong, W.F., Weng, M.R., and Shui, G. (2014). J. Genet. Genom. 41: 293–304.
- 54Chua, S.C., Tan, C.P., Mirhosseini, H. et al. (2009). J. Food Eng. 92: 403–409.
- 55Majid, R.A., Mohamad, A.W., and May, C.Y. (2013). J. Oil Palm Res. 25: 253–264.
- 56Panpipat, W. and Chaijan, M. (2015). In: Polar Lipids: Biology, Chemistry, and Technology (ed. M. Ahmad and X.B. Xu), 77–90. AOCS Press.
10.1016/B978-1-63067-044-3.50008-X Google Scholar
- 57Koo, O.M., Rubinstein, I., and Onyuksel, H. (2005). Nanomedicine 1: 193–212.
- 58Warner, T.G. and Benson, A.A. (1977). J. Lipid Res. 18: 548–552.
- 59Hermetter, A. and Paltauf, F. (1981). Chem. Phys. Lipids 28: 111–115.
- 60Eibl, H. (1984). Angew. Chem. Int. Engl. 23: 257–271.
- 61Ohno, M., Fujita, K., Nakai, H. et al. (1985). Chem. Pharm. Bull. 33: 572–582.
- 62Hope, M.J. and Cullis, P.R. (1980). Biochem. Biophys. Res. Commun. 92: 840–852.
- 63Farren, S.B., Hope, M.J., and Cullis, P.R. (1983). Biochem. Biophys. Res. Commun. 111: 675–682.
- 64Hope, M.J., Walker, D.C., and Cullis, P.R. (1983). Biochem. Biophys. Res. Commun. 110: 15–22.
- 65Cullis, P.R., Hope, M.J., and Tilcock, C.P.S. (1986). Chem. Phys. Lipids 40: 127–144.
- 66Tilcock, C.P. (1986). Chem. Phys. Lipids 40: 109–125.
- 67Edwards, K., Johnson, M., Karleson, G. et al. (1997). Biophys. J. 73: 258–266.
- 68Allen, T.M. and Cullis, P.R. (2013). Adv. Drug Deliv. Rev. 65: 36–48.
- 69Ahmad, I. and Allen, T.M. (1992). Cancer Res. 52: 4817–4820.
- 70Ahmad, I., Longenecker, M., Samuel, J., and Allen, T.M. (1993). Cancer Res. 53: 1484–1488.
- 71Kenworthy, A.K., Simon, S.A., and Mcintosh, T.J. (1995). Biophys. J. 68: 1903–1920.
- 72Ahmad, I., Sarkar, A.K., and Bachhawat, B.K. (1990). Biotechnol. Appl. Biochem. 12: 550–556.
- 73Gu, L.W., Gao, X.R., and Zhao, J.L. (1999). China Oils Fats 24: 60–62.
- 74Song, Y.Q., Yu, D.Y., Luo, S.N., and Wang, S.R. (2007). Soybean Bull. 4: 22–29. ISSN: 1009-2765.
- 75Hama, S., Ogino, C., and Kondo, A. (2015). Appl. Microbiol. Biotechnol. 99: 7879–7891.
- 76Zhang, H.F., Gao, H., Huang, Y.R. et al. (2004). China Leather. 33: 48–51.
- 77Taylor, K.M. and Morris, R.M. (1995). Thermochim. Acta. 248: 289–301.
- 78Contreras, F.-X., Sot, J., Ruiz-Arguello, M.-B. et al. (2004). Chem. Phys. Lipids 130: 127–134.
- 79Samad, A., Sultana, Y., and Aqil, M. (2007). Curr. Drug Deliv. 4: 297–305.
- 80Ikeda, A., Kawai, Y., Kikuchi, J. et al. (2011). Org. Biomol. Chem. 9: 2622–2627.
- 81Hernandez, E. and Quezada, N. (2008). In: Phospholipid Technology and Applications (ed. F.D. Gunstone), 83–94. Bridgewater: The Oily Press.
- 82Van Nieuwehuyzen, W. (2015). In: Polar Lipids: Biology, Chemistry, and Technology (ed. M. Ahmad and X.B. Xu), 245–276. AOCS Press.
10.1016/B978-1-63067-044-3.50013-3 Google Scholar
- 83Ghyczy, M. (1994). Food Tech. Europe 1: 44–46.
- 84Van Hoogevest, P., Liu, X., Fahr, A., and Leigh, M.L.S. (2011). J. Drug. Deliv. Sci. Technol. 21: 5–133.
- 85Fricker, G., Kromp, T., Wendel, A. et al. (2010). Pharm. Res. 27: 1469–1486.
- 86 US Food and Drug Administration (2013). Inactive, Ingredient Search for Approved Drug Products. http://www.accessdata.fda.gov/scripts/cder/iig/index/cfm.
- 87Ahmad, I., Sarkar, A.K., and Bachhawat, B.K. (1989). Mol. Cellular Biochem. 91: 85–90.
- 88Sharma, A. and Sharma, U. (1997). Int. J. Pharmaceut. 154: 123–140.
- 89Immordino, M., Dosio, F., and Cattel, L. (2006). Int. J. Nanomed. 3: 297–315.
- 90Mufamadi, M., Pillay, V., Choonara, Y. et al. (2011). J. Drug Deliv. 2011: 1–19.
- 91Akbarzadeh, A., Sadabady, R.R., Davaran, S. et al. (2013). Nanoscale Res. Lett. 8: 102–110.
- 92Gambling, D., Hughes, T., Martin, G. et al. (2005). Anesth. Analog. 100: 1065–1074.
- 93Driscoll, D. (2006). Pharm. Res. 23: 1959–1969.
- 94Cada, D., Levien, T., and Baker, D. (2008). Hosp. Pharm. 43: 903–912.
10.1310/hpj4311-903 Google Scholar
- 95Shah, P., Bhalodia, D., and Shelat, P. (2010). Syst. Rev. Pharm. 1: 24–32.
- 96Hammad, M.A. and Müller, B.W. (1998). Eur. J. Pharm. Biopharm. 46: 361–367.
- 97Gregory, T.J., Steinberg, K.P., Spragg, R. et al. (1997). A. J. Respir. Crit. Care Med. 155: 1309–1315.
- 98Duncan, R. and Gaspar, R. (2011). Mol. Pharm. 8: 2101–2141.
- 99Mayer, L.D., Bally, M.B., and Cullis, P.R. (1986). Biochim. Biophys. Biomembr. 857: 123–126.
- 100Drummond, D.C., Meyer, O., Hong, K. et al. (1999). Pharmacol. Rev. 51: 691–743.
- 101Allen, T., Williamson, P., and Schigel, R.A. (1988). Proc. Natl. Acad. Sci. 85: 8067–8071.
- 102Allen, T.M., Hansen, C., and Ratledge, J. (1989). Biochim. Biophys. Acta 981: 27–35.
- 103Allen, T.M. (1992). J. Liposome Res. 2: 289–305.
- 104Allen, T. and Chonn, A. (1987). FEBS Lett. 223: 42–46.
- 105Webb, M., Harasym, T., Masin, D. et al. (1995). Brit. J Cancer 72: 42–46.
- 106Allen, T.M. (1981). Biochim. Biphys. Acta Biomembr. 640: 385–397.
- 107Papahadjouios, D., Allen, T., Gabizon, A. et al. (1991). Proc. Natl. Acad. Sci. 88: 11460–11464.
- 108Glycolipids: Nature Publishing Group. http://www. nature.com/subjects/glycolipids/research-and-reviews (retrieved May 2016).
- 109Gillard, B.K., Thurmon, L.T., and Marcus, D.M. (1993). Glycobiology 3: 57–67.
- 110Simons, K. and Toomre, D. (2000). Natl. Rev. Mol. Cell Biol. 1: 31–41.
- 111Shaul, P.W. and Anderson, R.G. (1998). Am. J. Physiol. 275: 843–851.
- 112Malhotra, R. (2012). Biochem. Anal. Biochem. 1: 108. doi: 10.4172/2161-1009.1000108.
10.4172/2161‐1009.1000108 Google Scholar
- 113Christie, W.W. (2003). Lipid Analysis, 3e. Bridgewater: Oily Press.
- 114Ishizuka, I. (1997). Prog. Lipid Res. 36: 245–319.
- 115Shulze, H. and Sandhoff, K. (2011). Cold Spring Harb. Perspect. Biol. 3: a004804.
- 116Heinz, E. and Christie, W.W. (1996). Advances in Lipid Methodology, vol. 3. Dundee: Oily Press.
- 117Fujino, Y., Nakano, M., and Saeki, T. (1970). Agri. Biol. Chem. 34: 442–447.
- 118Frankenburg, S., Leibovici, V., Mansbach, N. et al. (1990). J. Immunol. 145: 4284–4289.
- 119Forestier, C.-L., Gao, Q., and Boons, G.-J. (2014). Front. Cell Infect. Microbiol. 4: 193. doi: 10.3389/fcimb.2014.000193.
- 120Goel, A., Vohra, H., and Varshney, G.C. (1999). Parasitol. Res. 85: 19–24.
- 121Pinherio, R.O., Pinto, E.F., De Matos Guedes, H.L. et al. (2007). Vaccine 25: 2716–2722.
- 122Pinheiro, R.O., Pinto, E.F., Lopes, J.R. et al. (2005). Microb. Infect. 7: 1317–1323.
- 123Tonui, W.K., Mpoke, S.S., Orago, A.S. et al. (2003). Onderstepoort. J. Vet. Res. 70: 255–263.
- 124Amprey, J.L., Im, J.S., Turco, S.J. et al. (2004). J. Exp. Med. 200: 895–904.
- 125Martinez Salazar, M.B., Delgado Dominguez, J., Silva Estrade, J. et al. (2014). Vaccine 32: 1259–1265.
- 126DeVries, A.L. and Wohlschlag, C. (1969). Science 163: 1073–1075.
- 127DeVries, A.L. (1971). Science 172: 1152–1155.
- 128Wharton, D.A., Pow, B., Kristensen, M. et al. (2009). J. Insect. Physiol. 55: 27–31.
- 129Walters, K.R., Serianni, A.S., Voituron, Y. et al. (2011). J. Comp. Physiol. B. 181: 631–640.
- 130Walters, K.R., Pan, Q., Serianni, A.S., and Duman, J.G. (2009). J. Biol. Chem. 284: 16822–16831.
- 131Walters, K.R., Serianni, A.S., Sformo, T. et al. (2009). Proc. Natl. Acad. Sci. USA 106: 20210–20215.
- 132Duman, J.G. (2015). J. Exp. Biol. 218: 1846–1855.
- 133Daniotti, J.L., Vilcaes, A.A., Demichelis, V.T. et al. (2013). Front. Oncol. 3: 306. doi: 10.3389/fonc.2013.00306.
- 134 Bovine Spongiform Encephalopathy (BSE) Letter-FDA (2000). https://www.fda.gov/downloads/BiologicsBloodVaccines/¨./UCM162938.pdf (19 April 2000).
- 135Ali, S.M., Ahmad, A., Sheikh, S. et al. (2010). Int. Immunopharmacol. 10: 325–330.
- 136Ahmad, A., Sheikh, S., Ali, S.M. et al. (2015). J. Cancer Sci. Ther. 7: 116–120.
- 137Ahmad, A., Sheikh, S., Ali, S.M. et al. (2015). J. Nanomed. Nanotech. 6: 295. doi: 10.4172/2157-7439.1000295.
10.4172/2157‐7439.1000295 Google Scholar
