ISSN 1070-4272, Russian Journal of Applied Chemistry, 2006, Vol. 79, No. 8, pp. 1371!1373. + Pleiades Publishing, Inc., 2006.
Original Russian Text + G. Khabdolda, V.I. Yamovoi, A.G. Berdin, K.M. Turdybekov, B.I. Tuleuov, P.V. Tarlykov, U.A. Baltaev, Yu.V. Gatilov,
A.B. Ospanova, S.M. Adekenov, 2006, published in Zhurnal Prikladnoi Khimii, 2006, Vol. 79, No. 8, pp. 1385!1387.
Crystal and Molecular Structure of Tigogenin
G. Khabdolda, V. I. Yamovoi, A. G. Berdin, K. M. Turdybekov, B. I. Tuleuov,
P. V. Tarlykov, U. A. Baltaev, Yu. V. Gatilov, A. B. Ospanova, and S. M. Adekenov
Institute of Phytochemistry, Ministry of Education and Science of the Republic of Kazakhstan,
Novosibirsk Institute of Organic Chemistry, Siberian Division, Russian Academy of Sciences,
Received April 12, 2006
Abstract-Tigogenin [(25R)-5a-spirostan-3b-ol] was isolated from Digitalis lanata Ehrh., and its crystal
and molecular structure was determined by single crystal X-ray diffraction.
Digitalis lanata Ehrh. is one of promising sources
of cardenolides ; it also contains steroid saponins
. Preparations from the Digitalis lanata Ehrh. tops
are widely used in medicine as cardiotonic agents .
Tigogenin [(25R)-5a-spirostan-3b-ol] has been pre-
viously found in Digitalis lanata Ehrh.  and in
some other plants [5, 6].
A TLC analysis and acid hydrolysis (5% H
1,3-dioxane3water, 1 : 1, 4 h, refluxing) showed that
the tops of Digitalis lanata Ehrh., collected in the
flowering period from the cultivated plants (herb seed
growing nursery of the Institute of Phytochemistry,
Ministry of Education and Science of the Republic of
Kazakhstan, Karaganda), contain both tigogenin and,
apparently, its glycosides.
The vegetable raw material was extracted with 70%
ethanol; lipophilic components were removed from
the extract by treatment with petroleum ether. Then
the extract was hydrolyzed as described above. From
the hydrolysis products, we isolated (25R)-5a-spiro-
stan-3b-ol by column chromatography on alumina.
The product was identified by its melting point and
the melting point of its acetate .
We found no data on the crystal and molecular
structure of I in the Cambridge Crystallographic Data-
base , and, therefore, we studied its structure by
single crystal X-ray diffraction.
Molecular structure of I.