Institute of Medicinal Plant Development, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100193, People's Republic of China; School of Pharmacy, Henan University of Chinese Medicine, Zhengzhou 450046, People's Republic of China.
School of Pharmacy, Henan University of Chinese Medicine, Zhengzhou 450046, People's Republic of China.
Fitoterapia. 2022 Sep;161:105258. doi: 10.1016/j.fitote.2022.105258. Epub 2022 Jul 25.
A phytochemical investigation of the 95% ethanol extract from Gerbera piloselloides obtained fourteen compounds, including three undescribed phenone-monoterpenes (1a/1b and 2), seven undescribed chromone-monoterpenes (3a/3b-5a/5b and 6), and one undescribed coumarin-monoterpene (8). Among them, four pairs of enantiomers (1a/1b and 3a/3b-5a/5b) were successfully isolated by the chiral-phase HPLC resolution. The structures and absolute configurations were unambiguously determined based on comprehensive spectroscopic data, electronic circular dichroism (ECD) data, and X-ray diffraction analysis. Structurally, compound 1 is the first 5-methylphenone monoterpene formed through a circular 6-membered carbocycle. And their anti-inflammatory and antiproliferative activities were evaluated via LPS stimulated RAW 264.7 cells and five human cancer lines (HepG2, MDA-MB-231, SCG-7901, A549 and MCF-7), respectively. Compounds 4b, 5a and 5b showed moderate inhibitory effect against nitric oxide (NO) production with IC values ranging from 12.52 to 15.75 μM. Compound 8 significantly inhibited the proliferation of MDA-MB-231 human cancer line in a dose-dependent manner. Furthermore, the connection between phenone-monoterpenes, chromone-monoterpenes, and coumarin-monoterpenes in biosynthesis were also discussed.
从垂头菊中 95%乙醇提取物的植物化学研究中分离得到了 14 种化合物，包括 3 种新的苯甲酮单萜（1a/1b 和 2）、7 种新的色酮单萜（3a/3b-5a/5b 和 6）和 1 种新的香豆素单萜（8）。其中，通过手性相高效液相色谱拆分成功分离出 4 对非对映异构体（1a/1b 和 3a/3b-5a/5b）。基于综合光谱数据、电子圆二色（ECD）数据和 X 射线衍射分析，明确了它们的结构和绝对构型。结构上，化合物 1 是第一个通过环状 6 元碳环形成的 5-甲基苯甲酮单萜。并通过 LPS 刺激的 RAW 264.7 细胞和 5 个人类癌细胞系（HepG2、MDA-MB-231、SCG-7901、A549 和 MCF-7）分别评估了它们的抗炎和抗增殖活性。化合物 4b、5a 和 5b 对一氧化氮（NO）的产生具有中等抑制作用，IC 值范围为 12.52-15.75μM。化合物 8 对 MDA-MB-231 人癌细胞系的增殖具有显著的剂量依赖性抑制作用。此外，还讨论了苯甲酮单萜、色酮单萜和香豆素单萜在生物合成中的联系。
