Isolation and Structure of the New Sesquiterpene Lactone 3-oxo-10β-hydroxy-5,7α(H),4,6β(H)-guai-1,11(13)-diene-6,12-olide
Жаңа сесквитерпендік лактон 3-оксо-10β-гидрокси-5,7α(Н),4,6β(Н)-гвай-1,11(13)-диен-6,12-олидтың оқшаулануы және құрылымы
Выделение и структура нового сесквитерпенового лактона 3-оксо-10β-гидрокси-5,7α(H),4,6β(H)-гвай-1,11(13)-диен-6,12-олида
Turdybekov K.M. Ivasenko S.A. Turdybekov D.M. Makhmutova A.S. Gatilov Yu.V. Adekenov S.M.
2022E.A.Buketov Karaganda State University Publish House
Bulletin of the Karaganda University Chemistry Series
2022#106Issue 252 - 60 pp.
The article presents the results of a chemical study of Tanacetopsis pjataevae, which is an endemic plant in Kazakhstan. The number of extractive substances was obtained by extraction with chloroform from the air-dry crushed above-ground part of the plant collected in the flowering phase. Isolation of compounds was carried out by column chromatography on a column of silica gel brand KSK at a ratio of sum - carrier = 1:20. A colorless crystalline substance of the composition C15H18O4 with m.p. 189–191°C (recrystallized from diethyl ether) was found when the column was eluted with a mixture of petroleum ether-ethyl acetate (87.5:12.5). The structure of the obtained new compound (3-oxo-10β-hydroxy-5,7α(Н),6β(Н)-guai-1,11(13)-diene-6,12-olide) was established based on IR, NMR analysis and mass spectra. The spatial structure was determined by the X-ray diffraction method. It was established that the 3-oxo-10β-hydroxy-5,7α(Н),6β(Н)-guai-1,11(13)-diene-6,12-olide molecule in the crystal is disordered over two conformational states in the 6:4 ratio. The stability of these conformers was confirmed by semi-empirical quantum-chemical calculations. It was established that the difference in the heat of formation of two conformers was 6.3 kJ/mol for a free molecule.
11(13)-diene-6 , 12-olide , 3-oxo-10β-hydroxy-5 , 6β(Н)-guai-1 , 7α(Н) , endemic , IR spectroscopy , mass spectrometry , NMR spectroscopy , sesquiterpene lactones , Tanacetopsis pjataevae , X-ray analysis
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Karagandy University of the name of academician E.A. Buketov, Universitetskaya street, 28, Karaganda, 100024, Kazakhstan
School of Pharmacy, Karaganda Medical University, Gogol street, 40, Karaganda, 100008, Kazakhstan
Candidate of Chemical Sciences, Karaganda Technical University, N. Nazarbayev str., 56, Karaganda, 100010, Kazakhstan
N.N. Vorozhtsov Institute of Organic Chemistry of Siberian Branch of Russian Academy of Sciences, Lavrentiev Avenue, 9, Novosibirsk, 630090, Russian Federation
International Research and Production Holding “Phytochemistry”, Gazaliev str. 4, Karaganda, 100009, Kazakhstan
Karagandy University of the name of academician E.A. Buketov
School of Pharmacy
Candidate of Chemical Sciences
N.N. Vorozhtsov Institute of Organic Chemistry of Siberian Branch of Russian Academy of Sciences
International Research and Production Holding “Phytochemistry”
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