Institute of Traditional Chinese Medicine and Natural Products, College of Pharmacy, Jinan University, Guangzhou, People's Republic of China.
Phytochemistry. 2012 Apr;76:133-40. doi: 10.1016/j.phytochem.2012.01.003. Epub 2012 Jan 23.
Pseudoguaianolide sesquiterpene lactones minimolides A (1), B (2), C (3) and D (4) and two guaianolide sesquiterpene lactones minimolides E (5) and F (6), along with seven known ones (7-13), were isolated from the supercritical fluid extract of Centipeda minima. The structures of these compounds were elucidated by extensive spectroscopic methods (IR, UV, HRESIMS, 1D-NMR and 2D-NMR), and the complete structure and stereochemistry of 1 was further confirmed by X-ray diffraction analysis. Compounds 1, 5-8,11 and 13 displayed inhibitory activity against human nasopharyngeal cancer cells (CNE) with IC(50) values ranging from 1.1 to 20.3 μM. Compound 13 containing both α-methylene-γ-lactone and α, β-unsaturated cyclopentenone moieties exhibited even stronger inhibitory activity than that of cisplatin (positive control) through cell cycle arrest at G2/M phase. Isolation of six sesquiterpene lactones from Centipeda minima highlighted the potential of supercritical fluid extraction for enrichment of minor constituents for phytochemical study.
从 Centipeda minima 的超临界流体提取物中分离得到了假荆芥内酯倍半萜类化合物 minimolides A（1）、B（2）、C（3）和 D（4）以及两个荆芥内酯倍半萜类化合物 minimolides E（5）和 F（6），以及另外七个已知化合物（7-13）。通过广泛的光谱方法（IR、UV、HRESIMS、1D-NMR 和 2D-NMR）阐明了这些化合物的结构，并且通过 X 射线衍射分析进一步证实了 1 的完整结构和立体化学。化合物 1、5-8、11 和 13 对人鼻咽癌（CNE）细胞表现出抑制活性，IC（50）值范围为 1.1-20.3 μM。含有α-亚甲基-γ-内酯和α,β-不饱和环戊烯酮部分的化合物 13 通过将细胞周期阻滞在 G2/M 期，表现出比顺铂（阳性对照）更强的抑制活性。从 Centipeda minima 中分离出六种倍半萜类化合物，突出了超临界流体提取在富集植物化学成分研究中的次要成分方面的潜力。
