Sulferalin, a novel sulfonyl pseudoguaianolide sesquiterpene lactone from Sendai Helenium autumnale L.

✍ Scribed by Yoshikazu Kondo; Fumihiko Yoshizaki; Fumio Hamada; Jiro Imai; Genjiro Kusano

• Book ID: 104235994
• Publisher: Elsevier Science
• Year: 1977
• Tongue: French
• Weight: 233 KB
• Volume: 18
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)83706-0

✦ Synopsis

Several sesquiterpene lactones have recently gained attention as potential experimental tumor inhibitorsl. Our earlier reports 2,3 described the isolation and structural elucidation of 2-methoxydihydrohelenalin and of picrohelenin, a cytotoxic and intensely bitter pseudoguaianolide from Sendai !feleniwn autwmza2e L. (Compositae). In the course of the continuing studies on the constituents of Sendai H. autwnnate, three new sesquiterpene lactones were isolated. One of these lactones was, to our knowledge, the first recognized naturally-occuring sulfonyl pseudoguaianolide. In this communication, we wish to describe the structural elucidation of the sulfur-containing pseudoguaianolide and two closely related guaianolides, which we named sulferalin 1, halshalin 2, and akihalin 3. Sulferalin l_, mp 255-256". [a]D-1670 (c=O.47, pyridine), was isolated from the roots as colorless needles. The molecular formula C16H~20tS was assigned on the basis of the elemental analysis and high resolution mass spectrometry [Anal. Calcd. for C1&20&: