Petasins from the R hizomes of Ligularia fischeri and I ts D erivatives
Records of Natural Products
Year: 2014 Issue: 2 April-June
p.156 - 164
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Caifang Wang, Junping Li, Ru Yang, Yuan Zhao, Yuefang Cheng, Zhenzhong Zhang and Lan He
Five eremophilane sesquiterpenoids were isolated from the rhizomes of Ligularia fischeri grown in Henan province of China and identified as 3α-Tigloyloxyeremophila-9,11-dien-8-one (3), Isopetasan (4), Neopetasan (5), Isopetasol(6) and Petasol (7), by spectroscopic methods. Petasin (1) previously isolated was analyzed to determine its absolute configuration by X-ray single crystal diffraction. Five petasin derivatives including three new compounds (2a, 6a and 6b) were synthesized. 12 eremophilane sesquiterpenoids including the derivatives except for 4 (minor amount) were assessed against human neuroblastoma (SKN-SH) by the SRB method. 1 was also tested on inhibiting prostate carcinoma (Bc3) cell lines. The results showed 1 has the strong inhibitory activity against SKN-SH and Bc3 cell lines and other compounds with α-isopropylidene group also have the strong activity against the human neuroblastoma (SKN-SH). The above results indicated the α - isopropylidene group might be the active center against pulmonary carcinoma (SKN-SH) in the same eremophilane-type skeleton. Petasins may be interesting for their good bioactivities.KEYWORDS
- Ligularia fischeri
- isolation and structural modification
- single crystal X-ray diffraction. © 2014 ACG Publications. All rights reserved.