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从三萜木本植物的茎和枝中分离得到的未知的扁柏烷型二萜和齐墩果烷型三萜。

Undescribed abietane-type diterpenoids and oleanane-type triterpenoids from the stem and branch of Tripterygium wilfordii.

机构信息

Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs Research, Institute of Traditional Chinese Medicine and Natural Products, College of Pharmacy, Jinan University, Guangzhou, China.

Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs Research, Institute of Traditional Chinese Medicine and Natural Products, College of Pharmacy, Jinan University, Guangzhou, China.

出版信息

Phytochemistry. 2022 Sep;201:113258. doi: 10.1016/j.phytochem.2022.113258. Epub 2022 May 30.

Abstract

Six undescribed abietane-type diterpenoids (tripterydinoids A-F) and five undescribed oleanane-type triterpenoids (tripterytrinoids A-E) were obtained and determined from the stem and branch of Tripterygium wilfordii Hook. f. (Celastraceae). Tripterydinoids A-C possessed the abietane-type diterpenoid skeleton with rare 8, 9-epoxy ring. The structures of undescribed compounds were established by extensive spectroscopic studies [HRESIMS, 1D/2D-NMR and electronic circular dichroism (ECD) calculation]. The absolute configurations of tripterydinoids A, B, E and tripterytrinoid A were defined by X-ray crystallographic analyses. Bioactivity screening indicated that tripterydinoids A-C exhibited potent inhibitory effects against NO release in LPS-activated RAW 264.7 macrophages with IC values of 6.93, 4.46 and 2.98 μM, respectively. Meanwhile, tripterydinoids A-D and tripterytrinoids B, C showed moderate and selective cytotoxicities against five human tumor cell lines (A375, Huh7, MCF-7, HCT-116 and NCI-H460).

摘要

从卫矛科雷公藤(Tripterygium wilfordii Hook. f.)的茎和枝中分离得到并鉴定了 6 个未描述的贝壳杉烷型二萜(三萜烯 A-F)和 5 个未描述的齐墩果烷型三萜(三萜烯 A-E)。三萜烯 A-C 具有贝壳杉烷型二萜骨架,具有罕见的 8,9-环氧环。通过广泛的光谱研究 [高分辨率质谱、1D/2D-NMR 和电子圆二色性(ECD)计算] 确定了未知化合物的结构。通过 X 射线晶体学分析确定了三萜烯 A、B、E 和三萜烯 A 的绝对构型。生物活性筛选表明,三萜烯 A-C 对 LPS 激活的 RAW 264.7 巨噬细胞中的 NO 释放具有很强的抑制作用,IC 值分别为 6.93、4.46 和 2.98 μM。同时,三萜烯 A-D 和三萜烯 B、C 对五种人肿瘤细胞系(A375、Huh7、MCF-7、HCT-116 和 NCI-H460)表现出中等程度的选择性细胞毒性。

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