A new eremophilanolide from Senecio sinuatus Gilib

✍ Scribed by Eleuterio Burgueño-Tapia; Susana López-Escobedo; Manuel González-Ledesma; Pedro Joseph-Nathan

• Publisher: John Wiley and Sons
• Year: 2007
• Tongue: English
• Weight: 214 KB
• Volume: 45
• Category: Article
• ISSN: 0749-1581
• DOI: 10.1002/mrc.1990

✦ Synopsis

Abstract

From the hexane extracts of Senecio sinuatus roots, the new 3β‐angeloyloxy‐6β‐hydroxyeremophil‐1(10)‐en‐8β,12‐olide (3), along with the known compounds 3β‐angeloyloxy‐6β‐hydroxyeremophil‐1(10)‐ene (1), 3β‐senecioyloxy‐6β‐hydroxyeremophil‐1(10)‐ene (2), and 3β‐angeloyloxy‐6β,8α‐dihydroxyeremophil‐1(10)‐en‐8β,12‐olide (4), were isolated. Complete ^1^H and ^13^C NMR chemical shift assignments of 1–4 were achieved using one‐ and two‐dimensional NMR techniques, including gHMQC and gHMBC experiments. A Monte Carlo search, followed by B3LYP/6‐31G*DFT calculation, provided the theoretical conformations of the eremophilane rings, which were in agreement with results derived from ^1^H^1^H NMR coupling constant analysis, and confirmed by NOESY experiments. Copyright © 2007 John Wiley & Sons, Ltd.