Abstract
Five sterylglycosides (acylmono-, mono-, di tri- and tetraglycosylsterol) and a saponin were isolated from Adzuki beans and characterized. In the glycosylsterols, the principal component sterols were sitosterol and stigmasterol; the major sugar component was glucose. The glucose units were shown to be linked by β1,6-bonds. The three oligoglycosylsterols were shown to be gentiobiosylsterol, gentiotriosylsterol and gentiotetraosylsterol; the latter two are novel sterylglycosides. The saponin was identified as glucopyranosyl-(β1→2)-glucopyranurosyl-(β1→3′)-soyasapogenol B (Azukisaponin I) which had previously been found in Adzuki beans.
Similar content being viewed by others
Abbreviations
- AG1ST:
-
acylmonoglycosy Isterol
- FD-MS:
-
field desorption-mass spectrometry
- G2SA:
-
diglycosyl type of Adzuki bean saponins
- G1ST:
-
monoglycosylsterol
- G2-5ST, di-, tri:
-
tetra-, pentaglycosylsterol
- GC-MS:
-
gas chromatography-mass spectrometry
- GLC:
-
gas-liquid chromatography
- IR:
-
infrared
- PMR:
-
proton magnetic resonance
- TLC:
-
thin-layer chromatography
- TMS:
-
trimethylsilyl
References
Eichenberger, W. (1977) inLipids and Lipid Polymers in Highre Plants (Tevini, M., and Lichtenthaler, H.K., eds.), pp. 169–182, Springer-Verlag, Berlin.
Mudd, J.B. (1980) inThe Biochemistry of Plants (Stumpf, P.K., and Conn, E.E., eds.), Vol. 4., pp. 509–534, Academic Press, New York, NY.
Hara, A., and Taketomi, T. (1980)Lipids 17, 515–518.
Muhindeen, I.A., Koerner, T.A.W., Samuelsson, B., Hirabayashi, Y., Degasperi, R., Li, S.-C., and Li, Y.-T. (1984)J. Lipid Res. 25, 1117–1123.
Livermore, B.P., Bey, R.F., and Johnson, R.C. (1978)Infection and Immunity 20, 215–220.
Mayberry, W.R., and Smith, P.F. (1983)Biochim. Biophys. Acta 752, 434–443.
Fujino, Y., and Ohnishi, M. (1979)Biochim. Biophys. Acta 574, 94–102.
Ohnishi, M., and Fujino, Y. (1980)Agric. Biol. Chem. 44, 333–338.
Tanaka, H., Ohnishi, M., and Fujino, Y. (1984)Nippon Nogeikagaku Kaishi 58, 17–24.
Ohnishi, M., and Fujino, Y. (1981)Phytochemistry 20, 1357–1358.
Khanma, I., Seshadri, R., and Seshadri, T.R. (1974)Phytochemistry 13, 199–202.
Tiwari, K.P., and Choudhary, R.N. (1979)Phytochemistry 18, 2044–2045.
Ghosal, S. and Saini, K.S. (1984)J. Chem. Research (M), 965–975.
Ghosal, S. (1985)Phytochemistry 24, 1807–1810.
Okuyama, E., and Yamazaki, M. (1983)Yakugaku Zasshi 103, 43–48.
Tietz, A., Kimura, Y., and Tamura, S. (1976)Z. Pflanzenphysiol. 81, 57–67.
Ito, S., Kojima, M., Ohnishi, M., and Fujino, Y. (1985)Nippon Nogeikagaku Kaishi 59, 895–900.
Rouser, G., Kritchevsky, G., Simon, G., and Nelson, G.T. (1967).Lipids 2, 37–40.
Kuroda, N., Ohnishi, M., and Fujino, Y. (1977)Cereal Chem. 54, 997–1006.
Kitagawa, I., Wang, H.K., Saito, M., and Yoshikawa, M. (1983)Chem. Pharm. Bull. 31, 683–688.
Kuhn, R. and Egge, H. (1963)Chem. Ber. 96, 3338–3348.
Hakomori, S. (1964)J. Biochem. 55, 205–208.
Laine, R.A., and Renkonen, O. (1975)J. Lipid Res. 16, 102–106.
Fujino, Y., Ohnishi, M., and Ito, S. (1985)Lipids 20, 337–342.
Nes, W.R. (1977) inAdvances in Lipid Research (Paoletti, R., and Kritchevsky, D., eds.) Vol. 15, pp. 233–324, Academic Press, New York, NY.
Nes, W.R., Krevitz, K., and Behzadan, S. (1976)Lipids 11, 118–126.
Kitagawa, I., Yoshikawa, M., and Yoshida, I. (1976)Chem. Pharm. Bull. 24, 121–129.
Björndal, H., Hellerqvist, C.G., Lindberg, B., and Svensson, S. (1970)Angew. Chem. 9, 610–619.
Matsubara, T., and Hayashi, A. (1974)Biomed. Madd Spectrom. 1, 62–65.
Radwan, S.S., Spener, F., and Mangold, H.K (1975)Chem. Phys. Lipids 14, 72–80.
Author information
Authors and Affiliations
About this article
Cite this article
Kojima, M., Ohnishi, M., Ito, S. et al. Characterization of acylmono-, mono-, di-, tri- and tetraglycosylsterol and saponin in Adzuki bean (Vigna angularis) seeds. Lipids 24, 849–853 (1989). https://doi.org/10.1007/BF02535758
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF02535758