Abstract
Spirostanol 3-O-oligosides (steroid saponins) are widely distributed in the plant kingdom, particularly in species belonging to the Liliaceae, Scrophulariaceae, Dioscoreaceae, Zygophyllaceae, and Solanaceae families1,2. The importance of these glycosides for chemical protection of plants against microbial pathogens and/or herbivores has been suggested3,4. The frequently observed fungitoxic, antiviral, cytostatic, and hypocholesterolemic activities6 of steroid saponins showed that these compounds are of more than academic interest. There are, however, only sparse data on the formation of steroid saponins in plants, especially at the enzyme level. The major part of information concerning the biosynthesis of these compounds is derived from experiments in which more or less distant labeled precursors (e.g. acetate, mevalonate, or cholesterol) were fed to the intact plants, plant organs, or cell cultures7,8. These experiments have elucidated in outline the biosynthetic pathways leading to the formation of spirostanol aglycones but until recently almost nothing was known about the synthesis of sugar chains of steroid saponins.
This is a preview of subscription content, log in via an institution to check access.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
Unable to display preview. Download preview PDF.
References
S.B. Mahato, A.N. Ganguly and N.P. Sahu, Steroid saponins, Phytochemistry 21: 959 (1982).
T. Nohara, Analysis of steroid sapogenins, in: Analysis of Sterols and Other Biologically Significant Steroids, W.D. Nes and E.J. Parish, Eds., Academic Press, San Diego (1989).
J.G. Roddick, Antifungal activity of plant steroids, in: Ecology and Metabolism of Plant Lipids, G. Fuller and W.D. Nes, Eds., American Chemical Society, Washington, DC (1987).
S. Grünweller, E. Schröder and J. Kesselmeier, Biological activities of furostanol saponins from Nicotiana tabacum, Phytochemistry 29: 2485 (1990).
T. Kawasaki, Spirostanol and furostanol type, in: Natural Products for Medicinal Use, S. Shibata, Ed., Nanzando Co., Tokyo (1982).
P.K. Kintia, G.W. Lazurevskii, N.N. Balashova, I.T. Balashova, A.I. Suruzhyu and W A. Lach, Structure and Biological Activity of Steroid Glycosides of Spirostane and Furostane Type (in Russian), Shtiinca, Kishinev (1987).
E. Heftmann, Biogenesis of steroids in Solanaceae, Phytochemistry 22: 1843 (1983).
V.A. Pasechnichenko, Biosynthesis and Biological Activity of Plant Terpenoids and Steroids (in Russian), Viniti, Moscow (1987).
M. Kalinowska and Z.A. Wojciechowski, Enzymatic synthesis of nuatigenin 3 ß-D-glucoside in oat (Avena sativa L.) leaves, Phytochemistry 25: 2525 (1986).
M. Kalinowska and Z.A. Wojciechowski, Subcellular localization of UDPG: nuatigenin glucosyltransferase in oat leaves, Phytochemistry 26: 353 (1987).
M. Kalinowska and Z.A. Wojciechowski, Substrate specificity of partially purified UDP-glucose: nuatigenin glucosyltransferase from oat leaves, Plant Sci. 55: 239 (1988).
C. Pgczkowski and Z.A. Wojciechowski, The occurrence of UDPG-dependent glucosyltransferase specific for sarsasapogenin in Asparagus officinalis, Phytochemistry 27: 2743 (1988).
C. Pgczkowski, J. Zimowski, D. Krawczyk and Z.A. Wojciechowski, Steroid specific glucosyltransferases in Asparagus plumosus shoots, Phytochemistry 29: 63 (1990).
C. Pgczkowski and Z.A. Wojciechowski, Glucosylation and galactosylation of diosgenin and solasodine by soluble glucosyltransferase(s) from Solanum melongena leaves, Phytochemistry 35: 1429 (1994).
P.K. Kintia and S.A. Shvets, Melongoside L and melongoside M - steroidal saponins from Solanum melongena seeds, Phytochemistry 24: 197 (1985).
P.K. Kintia and S.A. Shvets, Melongosides N, O and P - steroidal saponins from seeds of Solanum melongena, Phytochemistry 24: 1567 (1985).
M.M. Bradford, A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding, Analyt. Biochem. 72: 248 (1976).
Z.A. Wojciechowski, J. Zimowski. J.G. Zimowski and A. Lyznik, Specificity of sterol-glucosylating enzymes from Sinapis alba and Physarum polycephalum, Biochim. Biophys. Acta 570: 363 (1979).
U. Keil and P. Schreier, Purification and partial characterization of UDP-glucose: phenol- 3-Dglucosyltransferase from papaya fruit, Phytochemistry 28: 2281 (1989).
A. Bechthold, U. Berger and L. Heide, Partial purification, properties and kinetic studies of UDPglucose: p-hydroxybenzoate glucosyltransferase from cell cultures of Lithospermum erythrorhizon, Arch. Biochem. Biophys. 288: 38 (1991).
O.P. Sati and G. Pant, Spirostanol glycosides from Asparagus plumosus, Phytochemistry 24: 123 (1984).
G.M. Goryanu, V.V. Krohmalyuk and P.K. Kintia, Structure of asparagosides A and B from Asparagus officinalis (in Russian), Khim. Prir. Soedin. 3: 400 (1976).
R.A. Joly, J. Bonner, RD. Bennett and E. Heftmann, Conversion of cholesterol to an open-chain saponin by Dioscorea floribunda, Phytochemistry 8: 857 (1969).
F. Ronchetti, G. Russo, G. Ferrara and G. Vecchio, The role of (25S)-5a-cholestane-3f3,26-diol and (25S)-5a-furostane-313,26-diol in the biosynthesis of tomatidine and neotigogenin, Phytochemistry 13: 2423 (1975).
K.G. Gurielidze, V.A. Pasechnichenko and I.S. Vasilieva, Glucohydrolase from the leaves and roots of Dioscorea deltoidea Wall, Biokhirnya 52: 562 (1987).
B. Tal, J. Tamir, J.S. Rokem and J. Goldberg, Isolation and characterization of an intermediate steroid metabolite in diosgenin biosynthesis in suspension cultures of Dioscorea deltoidea cells, Biochem. J. 219: 619 (1984).
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 1996 Springer Science+Business Media New York
About this chapter
Cite this chapter
Paczkowski, C., Wojciechowski, Z.A. (1996). Purification and Properties of UDP-Glucose : Diosgenin/Tigogenin Glucosyltransferase from Solanum melongena Leaves. In: Waller, G.R., Yamasaki, K. (eds) Saponins Used in Traditional and Modern Medicine. Advances in Experimental Medicine and Biology, vol 404. Springer, Boston, MA. https://doi.org/10.1007/978-1-4899-1367-8_4
Download citation
DOI: https://doi.org/10.1007/978-1-4899-1367-8_4
Publisher Name: Springer, Boston, MA
Print ISBN: 978-1-4899-1369-2
Online ISBN: 978-1-4899-1367-8
eBook Packages: Springer Book Archive