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从大戟属植物中分离得到的具有生物活性的对映-新松香烷二萜。

Bioactive ent-isopimarane diterpenoids from Euphorbia neriifolia.

机构信息

Faculty of Life Science and Technology, Kunming University of Science and Technology, Kunming, 650500, Yunnan, P.R. China.

Surgical Science, Department of Surgery, Duke University Medical Center, Durham, NC, 27710, USA.

出版信息

Phytochemistry. 2020 Jul;175:112373. doi: 10.1016/j.phytochem.2020.112373. Epub 2020 Apr 16.

DOI:10.1016/j.phytochem.2020.112373
PMID:32305684
Abstract

Twelve ent-isopimarane diterpenoids, including six undescribed ones, eupnerias J-O, were isolated from the stem barks of Euphorbia neriifolia L. Structurally, eupnerias J-M were the first examples of 18 (or 19)-norditerpenoid with ent-isopimarane skeleton from E. neriifolia. The absolute configuration of eupneria J was established based on the X-ray diffraction analysis and the experimental and calculated electronic circular dichroism (ECD), while the absolute configuration of eupnerias K-N were determined by the experimental and calculated ECD. In addition, the absolute configuration of the known compound, 3β-hydroxysandaracopimaric acid, was determined by comparing its ECD spectrum with eupneria J, and renamed as eupneria P. Furthermore, eupneria J and eurifoloid H showed significant anti-HIV-1 activities with IC values of 0.31 and 6.70 μg/mL, respectively, and ent-isopimara-8(14),15-dien-3β,12β-diol possessed obvious anti-influenza virus activity against A/Puerto Rico/8/1934, with an IC at 3.86 μg/mL.

摘要

从大戟属植物(Euphorbia neriifolia L.)茎皮中分离得到 12 个新的对映-新松香烷二萜,包括 6 个未知化合物,命名为 eupnerias J-O。结构上,eupnerias J-M 是首次从大戟属植物中分离得到的具有 18(或 19)-降新松香烷骨架的 18-降二萜。根据 X 射线衍射分析和实验及计算的圆二色(ECD)光谱确定了 eupneria J 的绝对构型,而 eupnerias K-N 的绝对构型则通过实验和计算 ECD 确定。此外,通过与 eupneria J 的 ECD 光谱比较,确定了已知化合物 3β-羟基松香酸的绝对构型,并将其重新命名为 eupneria P。此外,eupneria J 和 eurifoloid H 表现出显著的抗 HIV-1 活性,IC 值分别为 0.31 和 6.70μg/mL,而对映-新松香烷-8(14),15-二烯-3β,12β-二醇对 A/Puerto Rico/8/1934 具有明显的抗流感病毒活性,IC 值为 3.86μg/mL。

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