New Eremophilenolides from Senecio dianthus

✍ Scribed by Yan-Hui Li; Yan Zhou; Gesang Suolang; Ciren Bianba; Li-Sheng Ding; Hui Feng

• Publisher: John Wiley and Sons
• Year: 2011
• Tongue: German
• Weight: 178 KB
• Volume: 94
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.201000237

✦ Synopsis

Abstract

From the aerial parts of Senecio dianthus, four new eremophilenolides (1–4, resp.) and one new eremophilenolide alkaloid (5), of the relatively uncommon eremophilenoid‐type sesquiterpenoid lactones, were isolated together with three known sesquiterpenoid lactones, 10__β__‐hydroxyeremophil‐7(11)‐en‐12,8__α__‐olide (6), 8__β__,10__β__‐dihydroxyeremophil‐7(11)‐en‐12,8__α__‐olide (7), and 10__α__‐hydroxy‐1‐oxoeremophila‐7(11),8(9)‐dien‐12,8‐olide (8). On the basis of IR, MS, and NMR data, particularly 2D‐NMR analyses, the structures of the new compounds were established as: 2__β__‐(angeloyloxy)‐10__β__‐hydroxyeremophil‐7(11)‐en‐12,8__α__‐olide (1), 6__β__‐(angeloyloxy)‐10__β__‐hydroxyeremophil‐7(11)‐en‐12,8__α__‐olide (2), 2__β__‐(angeloyloxy)‐8__β__,10__β__‐dihydroxyeremophil‐7(11)‐en‐12,8__α__‐olide (3), 2__β__‐(angeloyloxy)‐8__α__‐hydroxyeremophila‐7(11),9(10)‐dien‐12,8__β__‐olide (4), and 8__β__‐amino‐10__β__‐hydroxyeremophil‐7(11)‐en‐12,8__α__‐olide (5). In addition, the relative configuration of 1 was corroborated by X‐ray diffraction analysis.