Norsesquiterpenoid glucosides and a rhamnoside of pyrrolizidine alkaloid from Tephroseris kirilowii

Abstract

Four new glycosylated compounds have been isolated from the whole plant of Tephroseris kirilowii, including ( − )-(1R,5R,6S,7R,8S)-8-O-β-d-glucopyranosyloxy-7-hydroxy-6-(2-hydroxypropan-2-yl)-9-methylenebicyclo[4.3.0]non-3-one (tephroside A, 1), ( − )-(1R,5R,6R,8R)-6-(2-O-β-d-glucopyranosyloxypropan-2-yl)-8-hydroxy-9-methylenebicyclo[4.3.0]non-3-one (tephroside B, 2), thesinine-4′-O-α-l-rhamnoside (3), and p-coumaric acid 4-O-α-l-rhamnoside (4), together with the known roseoside. The structures of the new compounds were established by means of spectroscopic analysis.

Keywords:

• Tephroseris kirilowii
• Compositae
• Sesquiterpenoids
• Pyrrolizidine alkaloid
• Oplopane
• Tephroside

Acknowledgements

This work was financially supported by two grants from National Natural Science Foundation of China (No. 30370957) and Natural Science Foundation of Yunnan Province, China (No. 2003C0061M). We also thank Dr Jin-Jun Chen for affording the plant material.