Abstract
A new triterpene (I) has been isolated from the unsaponifiable fraction of an ethereal extract of the leaves ofBetula mandschurica to which, on the basis of the results of a physicochemical investigation and a comparison of the13C spectra with the spectra of known triterpenes — ocotillone (II) and 20(S)-hydroxydammar-24-en-3-one (III) — the structure of 20(S),24(S)-dihydroxydammar-25-3n-3-one has been assigned. An approach to the determination of the configuration of the asymmetric center at C24 in 24-hydroxy derivatives of tetracyclic triterpenoids with an open side chain by the use of13C NMR spectroscopy is proposed.
Similar content being viewed by others
Literature cited
P. G. Gorovoi, N. I. Uvarova, G. I. Oshitok, and G. B. Elyakov, Rast. Res.,11, 97 (1975)
N. I. Uvarova, G. V. Malinovskaya, Yu. N. El'kin, V. V. Isakov, A. K. Dzizenko, and G. B. Elyakov, Khim. Prir. Soedin., 757 (1976).
N. I. Uvarova, G. V. Malinovskaya, and G. B. Elyakov, Tetrahedron Lett., 4617 (1976).
G. V. Malinovskaya, N. D. Pokhilo, V. V. Isakov, and N. I. Uvarova, Khim. Prir. Soedin., 587 (1978).
A. K. Dzizenko, Yu. N. El'kin, E. V. Shapkina, L. I. Strigina, and G. B. Elyakov, Dokl. Akad. Nauk SSSR,173, 1080 (1967).
Yu. N. El'kin, A. K. Dzizenko, and G. B. Elyakov, Khim. Prir. Soedin., 286 (1971).
M. Nagai, N. Tanaka, O. Tanaka, and S. Ichikawa, Chen. Pharm. Bull.,21, 2061 (1973).
J. Asakawa, R. Kasai, K. Yamasaki, and O. Tanaka, Tetrahedron,33, 1935 (1977).
O. Tanaka and S. Yahara, Phytochemistry,17, 1353 (1978).
D. E. Dorman, M. Jautelat, and J. D. Roberts, J. Org. Chem.,36, 2757 (1971).
N. Koizumi, J. Fujimoto, T. Takeshita, and N. Ikekawa, Chem. Pharm. Bull.,27, 38 (1979).
S. Yakara, R. Kasai, and S. Tanaka, Chem. Pharm. Bull.,25, 2041 (1977).
S. Yahara, K. Kaji, and O. Tanaka, Chem. Pharm. Bull.,27, 88 (1979).
L. P. Linderman and J. G. Adams, Anal. Chem.,43, 1245 (1971).
G. Levy and G. Nelson, Carbon-13 in Nuclear Magnetic Resonance for Organic Chemists, Wiley-Interscience, New York (1972).
H. Beierbeck, J. K. Saunders, and J. W. Apsimon, Can. J. Chem.,55, 2813 (1977).
D. K. Dalling and D. M. Grant, J. Am. Chem. Soc.,96, 1827 (1974).
H. Beierbeck and J. K. Saunders, Can. J. Chem.,54, 2985 (1976).
F. Bohlmann, R. Zeisberg, and E. Klein, Org. Magn. Res.,7, 426 (1975).
F. C. Fischer and N. Seiler, Ann. Chem.,626, 185 (1959).
Additional information
Pacific Ocean Institute of Bioorganic Chemistry of the Far Eastern Scientific Center, Academy of Sciences of the USSR, Vladivostok. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 346–351, May–June, 1980.
Rights and permissions
About this article
Cite this article
Malinovskaya, G.V., Novikov, V.L., Denisenko, V.A. et al. A new triterpene from the leaves ofBetula mandschurica . Chem Nat Compd 16, 257–261 (1980). https://doi.org/10.1007/BF00567286
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00567286