Research Center for Drug Discovery, School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou 510006, People's Republic of China.
Research Center for Drug Discovery, School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou 510006, People's Republic of China.
Bioorg Chem. 2019 Nov;92:103292. doi: 10.1016/j.bioorg.2019.103292. Epub 2019 Sep 18.
Seven new diterpenoids, euphorantones A-D (1, 3, 6, and 10), 8,12,13-epi-3,7,12-O-triacetyl-8-O-(2-methylbutanoyl)-ingol (9), 8,12,13-epi-3,12-O-diacetyl-7-O-benzoyl-8-methoxyingol (11), 2,3-epi-7,12-diacetate-8-benzoate-ingol (12), together with eighteen known compounds (2, 4-5, 7-8, and 13-25), were isolated from the aerial parts of Euphorbia antiquorum L.. The structures of new compounds 1, 3, 6, and 9-12 were elucidated by extensive spectroscopic analyses. The absolute configurations of new compounds were assigned using X-ray diffraction, Rh(OCOCF)-induced CD spectrum, and confirmed through comparison of the calculated and experimental C NMR and electronic circular dichroism (ECD) data. Compounds 1-25 were evaluated for their inhibition of RANKL-induced osteoclastogenesis. Compound 1 showed the most potent inhibition of RANKL-induced osteoclastogenesis with IC value of 0.3 μM. It inhibited NFAT transcript activity and osteoclast related genes TRAcP, CTSK, and NFATc1 expression.
从Euphorbia antiquorum L. 的地上部分分离得到七个新的二萜类化合物， euphorantones A-D（1、3、6 和 10）、8、12、13-epi-3、7、12-O-三乙酰-8-O-(2-甲基丁酰基)-ingol（9）、8、12、13-epi-3、12-O-二乙酰-7-O-苯甲酰-8-甲氧-ingol（11）、2、3-epi-7、12-二乙酸酯-8-苯甲酸酯-ingol（12），以及十八个已知化合物（2、4-5、7-8 和 13-25）。新化合物 1、3、6 和 9-12 的结构通过广泛的光谱分析阐明。新化合物的绝对构型通过 X 射线衍射、Rh(OCOCF)-诱导的 CD 光谱和通过比较计算和实验 C NMR 和电子圆二色性 (ECD) 数据来确定。对化合物 1-25 进行了抑制 RANKL 诱导的破骨细胞分化的评价。化合物 1 对 RANKL 诱导的破骨细胞分化的抑制作用最强，IC 值为 0.3 μM。它抑制 NFAT 转录活性和破骨细胞相关基因 TRAcP、CTSK 和 NFATc1 的表达。
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