Abstract
A triterpenoid glycoside has been isolated from the roots of a herb used in traditional Chinese medicine. The molecular structure of this compound and its derivatives have been determined by spectroscopic studies and an X-ray analysis of the 2α,3β,23α-triacetoxy-28β-methyl ester of the aglycone. This aglycone belongs to the ursene structure series. The hydroxy group on ring E of these triterpenoids is α orientated and the side chains at C(2), C(3), C(4) and C(17) are α.,β, α andβ orientated, respectively. The C ring, which has a double bond at C(12)=C(13), adopts a sofa conformation.
Similar content being viewed by others
References
Chang, Hson-Mou., Chiang, Teh-Chang., and Mak, T. C. W. (1982)J. Chem. Soc. Chem. Commun. 1197.
Chen, T. K., Ales, D. C., Baenziger, N. C., and Wiemer, D. F. (1983)J. Org. Chem. 48, 3525.
Durham, D. G., Liu, X., and Richards, R. M. E. (1992)J. Pharm. Pharmacol. 44 (suppl.), 1080.
Higuchi, R., Kawasaki, T., Biswas, M., Pandey, V. B., and Dasgupta, B. (1982)Phytochemistry. 21, 907.
Maartmann-Moe, K., Bickell, W., and Francis, G. W. (1987)Acta Cryst. C 43, 2362.
Mak, T. C. W., Chiang, Teh-Chang., and Chang, Hson-Mou. (1982)J. Chem. Soc. Chem. Comm. 785.
Mallinson, P. R., and Muir, K. W. (1985)J. Appl. Crystallogr. 18, 51.
Romussi, G., Bignardi, G., Sancassan, F., and Falsone, G. (1983)Liebigs Ann. Chem. 1448.
Seto, T., Tanaka, T., Tanaka, O., and Narahashi, N. (1984)Phytochemistry 23, 2829.
Sheldrick, G. M. (1976)Shelx76.Program for crystal structure determination (University of Cambridge, England).
Sheldrick, G. M. (1986)Shelxs-86. Program for the solution of crystal structures from diffraction data (Der Universität Göttingen, Germany).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Cox, P.J., Durham, D.G., Liu, X. et al. Molecular structures of four triterpenoids. X-ray crystallographic analysis of methyl 2α,3β,23α-triacetoxy-19α-hydroxyurs-12-en-28β-oate. Journal of Crystallographic and Spectroscopic Research 23, 779–783 (1993). https://doi.org/10.1007/BF01247240
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF01247240