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Structure of steroidal glycosides from the seeds of Hyoscyamus niger L. and their biological activity

Author: Nedova Irina
Degree:doctor of chemistry
Speciality: 02.00.10 - Bioorganic chemistry; chemistry of natural and physiological active compounds
Scientific adviser: Pavel Chintea
doctor habilitat, professor, Institute of Genetics and Plant Physiology of the ASM
Scientific council:


The thesis was presented on the 6 November, 2008
Approved by NCAA on the 22 January, 2009


Adobe PDF document0.41 Mb / in russian
Adobe PDF document0.39 Mb / in romanian


CZU 581.19:547.918 (043.3)

Adobe PDF document 1.07 Mb / in russian
124 pages


steroidal glycosides, Hyoscyamus niger L., black henbane, Solanaceae, spirostan, furostan, pregnan, HPLC, NMR-spectroscopy.


The work is focused on the study of steroidal glycosides isolated from Hyoscyamus niger L. (black henbane) seeds. A new plant source, containing steroidal glycosides of the spirostan, furostan and pregnan series has been found. A rational method has been developed to isolate a mixture of furostan glycosides from Hyoscyamus niger L. seeds. 17 individual steroidal glycosides (hyoscyamozides) were isolated from henbane’s seeds, which differ in the structure of aglycon and oligosaccharide chain, nine of them being novel compounds, their chemical structure was elucidated by modern physico-chemical methods.

Spirostan glycosides – hyoscyamozides А, В, В1, В2, С, С1, D and D1 are derivatives of tigogenin, and hyoscyamozide В3 that of diosgenin. Hyoscyamozides - А, В1, В2, В3 and С1 turned out to be known compounds, but they were discovered in the Hyoscyamus genus for the first time. Hyoscyamozide С2 is glycoside of 5-pregn– 16 –еn –20 –оn.

Furostan glycosides – hyoscyamozides Е, Е1, F, F1, J and J1 are derivatives of (25R)-5-furostan-3,22,26-triol, and that of Е2 of (25R)-5-furosten-3,22,26-triol. Hyoscyamozides Е1 and F1 are known compounds but before they were not discovered in the Hyoscyamus genus.

Antifungal, antiprotozoan and growth stimulating activity was determined in hyoscyamozides, the degree of which depends, in the first turn, on the nature of aglycon and on the number of sugar moieties in the carbohydrate chain. Among furostan hyoscyamozides compounds which adjust growth and development of tomato, cucumber and tobacco plants were revealed.