Abstract
Results are given which confirm the structure of the furostanol glycoside from tomato seeds forming wastes of the preserving industry. From a butanolic extract of the seeds ofLycopersicum esculentum Mill. we have isolated the furostanol glycoside tomatoside A (I) the structure of which has been established as 25(S)-5α-furostan-3β,22α,26-triol 26-O-β-D-glucopyranoside 3-O-[O-β-D-glucopyranosyl-(1→2)-O-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside]. At the same time, by enzymatic and chemical transformations three new spirostanol glycosides of neotigogenin have been obtained: tomatoside B (III), which is 25(S)-5α-spirostan-3β-ol 3-O-[O-β-D-glucopyranosyl-(1→2)-β-D-galactopyranoside], 25(S)-5α-spirostan-3β-ol 3-O-[O-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside] (V), and 25(S)-5α-spirostan-3β-ol 3-O-β-D-galactopyranoside (IV).
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Literature cited
A. P. Shchelochkova and K. K. Koshoev, Izv. Akad. Nauk Kirg. SSR, No. 3, 52 (1971).
S. Kiyosawa, M. Huton, T. Komori, T. Nohara, I. Hosokawa, and T. Kawasaki, Chem. Pharm. Bull.,16, 1162 (1968).
T. Kawasaki, T. Komori, K. Miyahara, T. Nohara, I. Hosokawa, and K. Mihashi, Chem. Pharm. Bull.,22, 2164 (1974).
M. E. Wall, C. R. Eddy, M. L. McClennan, and M. E. Klumpp, Anal. Chem., No. 24, 1337 (1952).
C. R. Eddy, M. E. Wall, and M. K. Scott, Anal. Chem.,25, 266 (1953). L953).
R. Tschesche, G. Ludke, and G. Wulff, Chem. Ber.,102, 1253 (1969).
R. Tschesche and G. Wulff, Fortschr. Chem. Org. Naturst.,30, 479 (1973).
P. K. Kintya and G. V. Lazur'evskii, Steroid Glycosides of the Spirostan Series [in Russian], Kishinev (1979), p. 62.
H. Sato and S. Sakamura, Agr. Biol. Chem.,37, 225 (1973).
L. H. Goodson and C. R. Noller, J. Am. Chem. Soc.,61, 2420 (1939).
T. T. Gorovits, Khim. Prir. Soedin., 263 (1970).
V. T. Cherobai, Zh. Obshch. Khim.,34, 1018 (1964).
S. Hakomori, J. Biochem.,55, 205 (1964).
J. M. Van der Veen, J. Org. Chem.,28, 564 (1963).
H. K. Kochetkov, A. F. Bochkov, B. A. Dmitriev, A. I. Usov, O. S. Chizhov, and V. N. Shibaev, Chemistry of the Carbohydrates [in Russian], Moscow, 43 (1967).
W. Klyne, Biochem. J.,47, xli (1950).
R. Kuhn, I. Low, and H. Trischmann, Chem. Ber.,90, 293 (1957).
Yu. S. Vollerner, M. B. Gorovich, T. T. Gorovits, and N. K. Abugakirov, Khim. Prir. Soedin., 740 (1978).
A. H. Albert, G. R. Petit, and P. Brown, J. Org. Chem.,38, 2197 (1973).
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Institute of Organic Chemistry, Academy of Sciences of the Kirghiz SSR, Frunze. Institute of the Chemistry of Plant Substances of the Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 533–540, July–August, 1980.
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Shchelochkova, A.P., Vollerner, Y.S. & Koshoev, K.K. Tomatoside a from the seeds ofLycopersicum esculentum . Chem Nat Compd 16, 386–392 (1980). https://doi.org/10.1007/BF00568374
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DOI: https://doi.org/10.1007/BF00568374