He Xiao-Feng, Ma Yun-Bao, Li Tian-Ze, Chen Ji-Jun
State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China.
State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China; University of Chinese Academy of Sciences, Beijing 100049, China.
Phytochemistry. 2024 Jan;217:113930. doi: 10.1016/j.phytochem.2023.113930. Epub 2023 Nov 20.
The ethanol and EtOAc extracts of Artemisia sacrorum exhibited inhibitory effect against HepG2, Huh7, and SK-Hep-1 cell lines with inhibitory ratios of 65.5%, 28.1%, 84.6%, and 93.5%, 82.0%, 89.0% at 200 μg/mL. Twenty-three undescribed guaiane-type sesquiterpene lactones, artemisacrolides A‒W, were isolated from A. sacrorum under the guidance of antihepatoma activity. Their structures were elucidated by spectral data (HRESIMS, IR, UV, 1D and 2D NMR), ECD calculations, and a single-crystal X-ray diffraction. Artemisacrolides A‒U were guaiane-type sesquiterpene lactones possessing α-methylene-γ-lactone and containing acetoxyl groups at C-8, and artemisacrolides V and W represented the first report from the genus Artemisia with a 1,10-rearranged guaiane-type sesquiterpene lactone. Antihepatoma assay suggested that artemisacrolides A‒U demonstrated better inhibitory activity in Huh7 and SK-Hep-1 cells than those of HepG2 cells. Among them, nine compounds exhibited significant inhibitory activity against Huh7 cells with IC values of 8.2-14.3 μM, superior or equal to that of sorafenib; seven compounds demonstrated obvious activity against SK-Hep-1 cells with IC values of 13.5-19.2 μM, which were equivalent to that of sorafenib. Artemisacrolides B and E were the most active ones in three human hepatoma cell lines with IC values of 21.9, 8.2, 16.9 and 22.6, 9.0, 17.3 μM.
五月艾的乙醇提取物和乙酸乙酯提取物对HepG2、Huh7和SK-Hep-1细胞系具有抑制作用，在200μg/mL时抑制率分别为65.5%、28.1%、84.6%和93.5%、82.0%、89.0%。在抗肝癌活性的指导下，从五月艾中分离出23个未报道的愈创木烷型倍半萜内酯，即五月艾内酯A-W。通过光谱数据（高分辨电喷雾电离质谱、红外光谱、紫外光谱、一维和二维核磁共振谱）、电子圆二色光谱计算和单晶X射线衍射对其结构进行了确证。五月艾内酯A-U为具有α-亚甲基-γ-内酯且在C-8位含有乙酰氧基的愈创木烷型倍半萜内酯，五月艾内酯V和W代表了蒿属中首次报道的具有1,10-重排的愈创木烷型倍半萜内酯。抗肝癌实验表明，五月艾内酯A-U对Huh7和SK-Hep-1细胞的抑制活性优于HepG2细胞。其中，9个化合物对Huh7细胞表现出显著的抑制活性，IC50值为8.2-14.3μM，优于或等同于索拉非尼；7个化合物对SK-Hep-1细胞表现出明显活性，IC50值为13.5-19.2μM，与索拉非尼相当。五月艾内酯B和E在三种人肝癌细胞系中活性最强，IC50值分别为21.9、8.2、16.9和22.6、9.0、17.3μM。
