Abstract
Sterols are important components of cell membranes, hormones, signalling molecules and defense-related biotic and abiotic chemicals. Sterol glycosyltransferases (SGTs) are enzymes involved in sterol modifications and play an important role in metabolic plasticity during adaptive responses. The enzymes are classified as a subset of family 1 glycosyltransferases due to the presence of a signature motif in their primary sequence. These enzymes follow a compulsory order sequential mechanism forming a ternary complex. The diverse applications of sterol glycosides, like cytotoxic and apoptotic activity, anticancer activity, medicinal values, anti-stress roles and anti-insect and antibacterial properties, draws attention towards their synthesis mechanisms. Many secondary metabolites are derived from sterol pathways, which are important in defense mechanisms against pathogens. SGTs in plants are involved in changed sensitivity to stress hormones and their agrochemical analogs and changed tolerance to biotic and abiotic stresses. SGTs that glycosylate steroidal hormones, such as brassinosteroids, function as growth and development regulators in plants. In terms of metabolic roles, it can be said that SGTs occupy important position in plant metabolism and may offer future tools for crop improvement.
Similar content being viewed by others
References
Li, Y., Baldauf, S., Lim, E. K., & Bowles, D. J. (2001). The Journal of Biological Chemistry, 276, 4338–4343.
Mackenzie, P. I., Owen, I. S., Burchell, B., Bock, K. W., Bairoch, A., Bélanger, A., et al. (1997). Pharmacogenetics, 7, 255–269.
Paquette, S., Moller, B. L., & Bak, S. (2003). Phytochemistry, 62, 399–413.
Ross, J., Li, Y., Lim, E. K., & Bowles, D. J. (2001). Genome Biology, 2, 3004.1–3004.6.
Kapitonov, D., & Yu, R. K. (1999). Glycobiology, 9, 961–978.
Vogt, T., & Jones, P. (2000). Trends in Plant Science, 5, 380–386.
Bowles, D. J., Poppenberger, B., & Vaistij, F. (2006). Annual Review of Plant Biology, 57, 567–597.
Ikan, R. (444). Naturally occurring glycosides. Chichester: Wiley.
Jones, P., & Vogt, T. (2001). Planta, 213, 164–174.
Lim, E. K., & Bowles, D. J. (2004). The EMBO Journal, 23, 2915–2922.
Pflugmacher, S. S. H. (1998). Phytochemistry, 49, 507–511.
Martinoia, E. K. M., Gesser, M., Sanchez-Hernandez, R., & Rea, P. A. (2001). Vacuolar transport of secondary metabolites and xenobiotics. UK: Sheffield Acad.
Dietz, K. J., Sauter, A., Wichert, K., Messdaghi, D., & Hartung, W. (2000). Journal of Experimental Botany, 51, 937–944.
Samuels, A. L., Rensing, K. H., Douglas, C. J., Mansfield, S. D., Dharmawardhana, D. P., & Ellis, B. E. (2002). Planta, 216, 72–82.
Wojciechowski, Z. A., & Van Uon, N. (1975). Acta Biochimica Polonica, 22, 25–38.
He, J. X., Fujioka, S., Li, T. S., Kang, S. G., Seto, H., Takatsuto, S., et al. (2003). Plant Physiology, 131, 1258–1269.
Schumacher, K., & Chory, J. (2000). Current Opinion in Plant Biology, 3, 79–84.
Wanke, M., Skorupinska-Tudek, K., & Swiezewska, E. (2001). Acta Biochemica Polonica, 48, 663–672.
Benveniste, P. (2004). Annual Review of Plant Biology, 55, 429–457.
Grille, S., Zaslawski, A., Thiele, S., Plat, J., & Warnecke, D. (2010). Progress in Lipid Research, 49, 262–288.
Ly, P. T. T., Singh, S., & Shaw, C. A. (2007). Journal of Neuroscience Research, 85, 231–237.
Cruz-Aguado, R., & Shaw, C. A. (2009). Neurology, 72, 474–476.
Haralampidis, K., Trijanowska, M., & Osbourn, A. E. (2002). Advances in Biochemical Engineering/Biotechnology, 75, 31–49.
Ullmann, P., Ury, A., Rimmele, D., Benveniste, P., & Bouvier-Nave, P. (1993). Biochimie, 75, 713–719.
Webb, M. S., Irving, T. C., & Steponkus, P. L. (1995). Biochimica et Biophysica Acta, 1239, 226–238.
Kojima, M., Ohnishi, M., Ito, S., & Fujino, Y. (1989). Lipids, 24, 849–853.
Mulichak, A. M., Losey, H. C., Walsh, C. T., & Garavito, R. M. (2001). Structure (Camb.), 9, 547–557.
Mulichak, A. M., Losey, H. C., Lu, W., Wawrzak, Z., Walsh, C. T., & Garavito, R. M. (2003). Proceedings of the National Academy of Science, 100, 9238–9243.
Mulichak, A. M., Lu, W., Losey, H. C., Walsh, C. T., & Garavito, R. M. (2004). Biochemistry, 43, 5170–5180.
Offen, W., Martinez-Fleites, C., Yang, M., Kiat-Lim, E., Davis, B. G., Tarling, C. A., et al. (2006). The EMBO Journal, 25, 1396–1405.
Shao, H., He, X., Achinine, L., Blount, J. W., Dixon, R. A., & Wang, X. (2005). The Plant Cell, 17, 3141–3154.
Madina, B. R., Sharma, L. K., Chaturvedi, P., Sangwan, R. S., & Tuli, R. (2007). Biochimica et Biophysica Acta, 1774, 392–402.
Madina, B. R., Sharma, L. K., Chaturvedi, P., Sangwan, R. S., & Tuli, R. (2007). Biochimica et Biophysica Acta, 1774, 1199–1207.
Sharma, L. K., Madina, B. R., Chaturvedi, P., Sangwan, R. S., & Tuli, R. (2007). Archives of Biochemistry and Biophysics, 460, 48–55.
Lescovac, V. (2003). Comprehensive enzyme kinetics. Newyork: Kluwer.
Mackenzie, P. I., & Rodbourn, L. (1990). The Journal of Biological Chemistry, 265, 11328–11332.
Mackenzie, P. I. (1990). The Journal of Biological Chemistry, 265, 3432–3435.
Evans, O. P., & O’reilly, D. R. (1998). The Biochemical Journal, 330, 1265–1270.
Ullmann, P., Bouvier-Nave, P., & Benveniste, P. (1987). Plant Physiology, 85, 51–55.
Warnecke, D. C., & Heinz, E. (1994). Plant Physiology, 105, 1067–1073.
Warnecke, D. C., Baltrusch, M., Buck, F., Wolter, F. P., & Heinz, E. (1997). Plant Molecular Biology, 35, 597–603.
Hartmann-Bouillon, M. A., & Benveniste, P. (1978). Phytochemistry, 17, 1037–1042.
Yoshida, S., & Uemura, M. (1986). Plant Physiology, 82, 807–812.
Burbulis, I. E., & Winkel-Shirley, B. (1999). Proceedings of the National Academy of Sciences of the United States of America, 96, 12929–12934.
Bartholomew, D. M., Van Dyk, D. E., Lau, S. M. C., O’Keefe, D. P., Rea, P. A., & Viitanen, P. V. (2002). Plant Physiology, 130, 1562–1572.
Rea, P. A. (1999). Journal of Experimental Botany, 50, 895–913.
Radominska-Pandya, A., Czernik, P. J., Little, J. M., Battaglia, E., & Mackenzie, P. I. (1999). Drug Metabolism Reviews, 31, 817–899.
Hirschberg, C. B., Robbins, P. W., & Abeijon, C. (1998). Annual Review of Biochemistry, 67, 49–69.
Sakaki, T., Zahringer, U., Warnecke, D. C., Fahl, A., Knogge, W., & Heinz, E. (2001). Yeast, 18, 679–685.
Warnecke, D., Erdmann, R., Fahl, A., Hube, B., Muller, F., Zank, T., et al. (1999). The Journal of Biological Chemistry, 274, 13048–13059.
Smith, P. F. (1971). Journal of Bacteriology, 108, 986–991.
Patel, K. R., Smith, P. F., & Mayberry, W. R. (1978). Journal of Bacterial, 136, 829–831.
Mayberry, W. R., & Smith, P. F. (1983). Biochimica et Biophysica Acta, 752, 434–443.
Livermore, B. P., Bey, R. F., & Johnson, R. C. (1978). Infection and Immunity, 20, 215–220.
Hirai, Y., Haque, M., Yoshida, T., Yokota, K., Yasuda, T., & Oguma, K. (1995). Journal of Bacterial, 177, 5327–5333.
Lebrun, A. H., Wunder, C., Hildebrand, J., Churin, Y., Zähringer, U., Lindner, U. B., et al. (2006). The Journal of Biological Chemistry, 281, 27765–27772.
Wunder, C., Churin, Y., Winau, F., Warnecke, D., Vieth, M., Lindner, B., et al. (2006). Nature Medicine, 12, 1030–1038.
Berg, S., Edman, M., Li, L., Wikstrom, M., & Wieslander, A. (2001). The Journal of Biological Chemistry, 276, 22056–22063.
Holzl, G., Zahringer, U., Warnecke, D., & Heinz, E. (2005). Plant & Cell Physiology, 46, 1766–1778.
Khan, S., Sneddon, K., Fielding, B., Ward, V., & Davison, S. (2003). Virus Genes, 27, 17–27.
Esders, T. W., & Light, R. J. (1972). The Journal of Biological Chemistry, 247, 7494–7497.
McMorris, T. C., & White, R. H. (1977). Biochimica et Biophysica Acta, 486, 308–312.
Stasyk, O. V., Nazarko, T. Y., Stasyk, O. G., Krasovska, O. S., Warnecke, D., Nicaud, J. M., et al. (2003). Cell Biology, 27, 947–952.
Kim, Y. K., Wang, Y., Liu, Z. M., & Kolattukudy, P. E. (2002). The Plant Journal, 30, 177–187.
Murakami-Murofushi, K., & Ohta, J. (1989). Biochimica et Biophysica Acta, 992, 412–415.
Murakami-Murofushi, K., Nishikawa, K., Hirakawa, E., & Murofushi, H. (1997). The Journal of Biological Chemistry, 272, 486–489.
Abraham, W., Wertz, P. W., Burken, R. R., & Downing, D. T. (1987). Journal of Lipid Research, 28, 446–449.
Wertz, P. W., Stover, P. M., Abraham, W., & Downing, D. T. (1986). Journal of Lipid Research, 27, 427–435.
Weatherill, P. J., & Burchell, B. (1980). The Biochemical Journal, 189, 377–480.
Moghrabi, N., Sutherland, L., Wooster, R., Povey, S., Boxer, M., & Burchell, B. (1992). Annals of Human Genetics, 56, 81–91.
Ritter, J. K., Chen, F., Sheen, Y. Y., Tran, H. M., Kimura, S., Yeatman, M. T., et al. (1992). The Journal of Biological Chemistry, 267, 3257–3261.
Dutton, G. J. (1980). Glucuronidation of drugs and other compounds. Boca Raton: CRC.
Falany, C. N., Green, M. D., & Tephly, M. D. (1987). The Journal of Biological Chemistry, 262, 1218–1222.
Burchell, B., Nebert, D. W., Nelson, D. R., Bock, K. W., Iyanagi, T., Jansen, P. L., et al. (1991). Cell Biology, 10, 487–494.
Haque, S. J., Petersen, D. D., Nebert, D. W., & Mackenzie, P. I. (1991). DNA and Cell Biology, 10, 515–524.
Monaghan, G., Clarke, D. J., Povey, S., See, C. G., Boxer, M., & Burchell, B. (1994). Genomics, 23, 496–499.
Hostettmann, K., & Marston, A. (1995). Saponins. Cambridge: Cambridge University Press.
Hostettmann, A. M. K., Hostettmann, A., & Marston, A. (1995). Saponins, saponins chemistry and pharmacology of natural products. Cambridge: Cambridge University Press.
Morrissey, J. P., & Osbourn, A. E. (1999). Microbiology and Molecular Biology Reviews, 63, 708–724.
Misiak, M., Kalinowska, M., & Wojciechowski, Z. A. (1991). Acta Biochimica Polonica, 38, 43–45.
Dupéron, R., & Dupéron, P. (1989). Comptes Rendus de l’Academie des Sciences Serie III, 308, 31–34.
Verhoek, B., Haas, R., Wrage, K., Linscheid, M., & Heinz, E. (1983). Zeitschrift für Naturforschung, 38, 770–777.
Debolt, S., Scheible, W. R., Schrick, K., Auer, M., Beisson, F., Bischoff, V., et al. (2009). Plant Physiology, 151, 78–87.
Potocka, A., & Zimowski, J. (2008). Acta Biochimica Polonica, 55, 127–134.
Potocka, A., & Zimowski, J. (2008). Acta Biochimica Polonica, 55, 135–140.
Moehs, C., Friedman, P. A. M., & Belknap, W. (1997). The Plant Journal, 11, 227–236.
Kohara, A., Nakajima, C., Hashimoto, K., Ikenaga, T., Tanaka, H., Shoyama, Y., et al. (2005). Plant Molecular Biology, 57, 225–239.
Hillig, I., Leipelt, M., Ott, C., Zahringer, U., Warnecke, D., & Heinz, E. (2003). FEBS Letters, 553, 365–369.
Suzuki, H., Naoumkina, M. R. M., Aziz, N., & May, G. (2005). Planta, 220, 696–707.
Achnine, L., Huhman, D. V., Farag, M. A., Sumner, L. W., Blount, J. W., & Dixon, R. A. (2005). The Plant Journal, 41, 875–877.
Richman, A., Swanson, A., Humphrey, T., Chapman, R., & McGarvey, B. (2005). The Plant Journal, 41, 56–67.
Peng, L. C., Kawagoe, Y., Hogan, P., & Delmer, D. (2002). Science, 295, 147–150.
Cai-Jun, Y., & Jian-Jiang, Z. (2005). Process Biochemistry, 40, 3742–3748.
Paquin, R. (1966). American Potato Journal, 43, 349–354.
Andrivon, D., Corbière, R., Lucas, J. M., Pasco, C., Gravoueille, J. M., Pellé, R., et al. (2003). American Journal of Potato Research, 80, 125–134.
Chong, J., Baltz, R., Schmitt, C., Beffa, R., Fritig, B., & Saindrenan, P. (2002). The Plant Cell, 14, 1093–1097.
Jadhav, S. J., Sharma, R. P., & Salunkhe, D. K. (1981). Critical Reviews in Toxicology, 9, 21–104.
Osbourn, A. (1996). The Plant Cell, 10, 1821–1831.
Becker, P. (1998). FEMS Microbiology Letters, 167, 197–202.
Poppenberger, B., Berthiller, F., Lucyshyn, D., Sieberer, T., Schuhmacher, R., Krska, R., et al. (2003). The Journal of Biological Chemistry, 28, 47905–47914.
Keukens, E. A. J., Vrije, T. D., Boom, C. V. D., Waard, P. D., Plasmna, H. H., Theil, F., et al. (1995). Biochimica et Biophysica Acta, 1240, 216–228.
Armah, C. N., Mackie, A. R., Roy, C., Price, K., Osourn, A. E., Bowyer, P., et al. (1999). Biophysical Journal, 76, 281–290.
Sandrock, R. W., & Van Etten, H. D. (1998). Phytopathology, 88, 137–143.
Wubben, J. P., Price, K. R., Daniels, M. J., & Osbourn, A. E. (1996). Phytopathology, 86, 986–992.
Roddick, J. G., Rijnenberg, A. L., & Osman, S. F. (1988). Journal of Chemical Ecology, 14, 889–902.
Fewell, A. M., & Roddick, J. G. (1993). Phytochemistry, 33, 323–328.
Miyakoshi, M., Tamura, Y., Masuda, H., Mizutani, K., Tanaka, O., Ikeda, T., et al. (2000). Journal of Natural Products, 63, 332–348.
Flanders, K. L., Hawkes, J. G., Radcliffe, E. B., & Lauer, F. I. (1992). Euphytica, 61, 83–91.
Kowalski, S. P., Domek, J. M., Sanford, L. L., & Deahl, K. L. (2000). Journal of Entomological Science, 35, 290–300.
Sanford, L. L., Domek, J. M., Cantelo, W. W., Kobayashi, R. S., & Sinden, S. L. (1996). American Potato Journal, 73, 79–88.
Palta, J. P., & Li, P. H. (1980). Physiologia Plantarum, 50, 169–175.
Schaller, H. (2003). The role of sterols in plant growth and development. Progress in Lipid Research, 42, 163–175.
Bouvier-Nave, P., Ullmann, P., Rimmele, D., & Benveniste, P. (1984). Plant Science Letters, 36, 19–27.
Kingston, R. E., Schuetz, T. J., & Larin, Z. (1987). Molecular and Cellular Biology, 7, 1530–1534.
Kunimoto, S., Kobayashi, T., Kobayashi, S., & Murakami-Murofushi, K. (2000). Cell Stress & Chaperones, 5, 3–7.
Kunimoto, S., Kai, W. M. H., Ishida, Y., Uchiyama, A., Kobayashi, T., & Kobayashi, S. (2002). Cell Structure and Function, 27, 157–162.
Mongrand, S., Morel, J., Laroche, J., & Claverol, S. (2004). The Journal of Biological Chemistry, 279, 36277–36286.
Hansen, J., Türk, R., Vogg, G., Heim, R., & Beck, E. (1997). In H. Rennenberg, W. Eschrich, & H. Ziegler (Eds.), Trees-contributions to modern tree physiology (pp. 97–98). Leiden: Backhuys.
Nanjo, T., Kobayashi, M., Yoshida, Y., Kakubari, Y., Yamaguchi-Shinozaki, K., & Shinozaki, K. (1999). FEBS Letters, 461, 205–210.
Steponkus, P. L., Uemura, M., Joseph, R. A., Gilmour, S. J., & Thomashow, M. F. (1998). Proceedings of the National Academy of Science, 95, 14570–14575.
Steponkus, P. L. (1984). Annual Review of Plant Physiology, 35, 543–584.
Thomashow, M. F. (1998). Plant Physiology, 118, 1–7.
Patterson, G. W., Hugly, S., & Harrison, D. (1993). Phytochemistry, 33, 1381–1383.
Uemura, M., Joseph, R. A., & Steponkus, P. L. (1995). Plant Physiology, 109, 15–30.
Zhang, C. L. G. (2006). Plant Physiology and Biochemistry, 44, 844–850.
Wang, R. W. M. F., & Ding, C. K. (2005). ISHS Acta Horticult. 682.
Anderson, J. V., Li, Q. B., Haskell, D. W., & Guy, C. L. (1994). Plant Physiology, 104, 1359–1370.
Li, Q. B., Haskell, D. W., & Guy, C. L. (1999). Plant Molecular Biology, 39, 21–34.
Clouse, S. D., & Sasse, J. M. (1998). Annual Review of Plant Physiology and Plant Molecular Biology, 49, 427–451.
Grove, M. D., Spencer, G. F., Rohwedder, W. K., Mandava, N., Worley, J. F. Jr., Warthen, J. D., et al. (1979). Nature, 281, 216–217.
Adam, G., Schmidt, J., & Schneider, B. (1999). Fortschritte der Chemie Organischer Naturstoffe, 78, 1–46.
Clouse, S. (2001). Current Biology, 11, R904.
Fujioka, S., & Yokota, T. (2003). Annual Review of Plant Biology, 54, 137–164.
Kleczkowski, K., & Schell, J. (1995). Critical Reviews in Plant Sciences, 14, 283–298.
Barbier, O., Bélanger, A., & Hum, D. W. (1999). The Biochemical Journal, 337, 567–574.
Turgeon, D., Carrier, J. S., Chouinard, S., & Belanger, A. (2003). Drug Meta Dispo., 31, 670–676.
Poppenberger, B., Fujioka, S., Soeno, K., George, G. L., Vaistij, F. E., Hiranuma, S., et al. (2005). Proceedings of the National Academy of Science, 102, 15253–15258.
Choi, D., Ha, J. J. Y., Park, H., Su, I. D., Chung, H., & Liu, J. (2005). Plant Cell Reports, 23, 557–566.
Yue, C. J., & Zhong, J. J. (2005). Process Biochemistry, 40, 3742–3748.
Chen, R., Chung, T., Lin, F. N., & Tzen, J. (2009). Acta Pharmacologica Sinica, 30, 61–69.
Matsuda, H., Murakami, T., Kishi, A., & Yoshikawa, M. (2001). Bioorganic & Medicinal Chemistry, 9, 1499–1507.
Zhao, J., Nakamura, N., Hattori, M., Kuboyama, T., Tohda, C., & Komatsu, K. (2002). Chemical & Pharmaceutical Bulletin, 50, 760–765.
Jayaprakasam, B., & Muraleetharan, N. G. (2003). Tetrahedron, 59, 841–849.
Ahuja, A., Kaur, D., Sharada, M., Kumar, A., Suri, K. A., & Dutt, P. (2009). Nat Prod Comm., 4, 479–482.
Caradoc-Davies, K. M., Graves, S., O’Reilly, D. R., Evans, O. P., & Ward, V. K. (2001). Virus Genes, 22, 255–264.
Manzan, M. A., Lozano, M. E., Sciocco-Cap, A., Ghiringhelli, P. D., & Romanowski, V. (2002). Virus Genes, 24, 119–130.
Rodrigues, J. C., De Souza, M. L., O’Reilly, D., Velloso, L. M., Pinedo, F. J., Razuck, F. B., et al. (2001). Virus Genes, 22, 103–112.
Tumilasci, V. F., Leal, E., Zanotto, P. M., Luque, T., & Wolff, J. L. (2003). Virus Genes, 27, 137–144.
Wormleaton, S. L., & Winstanley, D. (2001). The Journal of General Virology, 82, 2295–2305.
Paczkowski, C., Kalinowska, M., & Wojciechowski, Z. A. (2001). Phytochemistry, 58, 663–669.
McCue, K. F., Allen, P. V., Shepherd, L. V., Blake, A., Whitworth, J., Maccree, M. M., et al. (2006). Phytochemistry, 67, 1590–1597.
Kurosawa, Y., Takahara, H., & Shiraiwa, M. (2002). Planta, 215, 620–629.
Bedir, E., & Khan, I. A. (2000). Journal of Natural Products, 63, 1699–1701.
Bedir, E., Pugh, N. P., Çalış, I., Pasco, D. A., & Khan, I. A. (2000). Biological & Pharmaceutical Bulletin, 23, 834–837.
Acknowledgements
The authors are thankful to the Council of Scientific and Industrial Research, New Delhi, Government of India, for providing the financial support under NMITLI scheme and Network Project (NWP-08) and also to the Department of Biotechnology, New Delhi, Government of India, for financial help through the project no. GAP 231225, for functional analysis of SGT genes of Withania somnifera.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Chaturvedi, P., Misra, P. & Tuli, R. Sterol Glycosyltransferases—The Enzymes That Modify Sterols. Appl Biochem Biotechnol 165, 47–68 (2011). https://doi.org/10.1007/s12010-011-9232-0
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s12010-011-9232-0