Collect. Czech. Chem. Commun.
1995, 60, 300-310
https://doi.org/10.1135/cccc19950300
X-Ray Structure Analysis and NMR Study of Sesquiterpene Lactone Hirsutolide
Urszula Rychłewskaa, Miloš Buděšínskýb, Halina Grabarczykc, Bohdan Drożdżc and Miroslav Holubb
a Department of Chemistry, Adam Mickiewicz University, 60-780 Poznań, Poland
b Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, 166 10 Prague 6, Czech Republic
c Department of Medical Plants, Academy of Medicine, 60-623 Poznań, Poland
Abstract
Hirsutolide, the C(8)-lactonized sesquiterpene of the heliangolide type has been studied by X-ray and NMR methods. In crystal the ten-membered ring conformation closely resembles the conformation observed in C(6)-lactonized heliangolides. This conformation, which can be described as a boat-chair is contrasted with the chair-chair conformation found in the crystals of other C(8)-lactonized heliangolide, scorpioidine. Broad signals in 1H and 13C NMR spectra indicated the conformation equilibrium in solution which was confirmed by observation of signals of two conformers (ca 3 : 1) in low temperature 1H NMR spectra. The major conformer is the one present in the crystal structure of hirsutolide and the minor conformer corresponds very likely to the one observed in the crystal structure of scorpioidine.
