Bioactive ent-isopimarane diterpenoids from Euphorbia neriifolia
2020
Li, Jian-Chun | Dai, Wei-Feng | Liu, Dan | Jiang, Ming-Yan | Zhang, Zhi-Jun | Chen, Xuan-Qin | Chen, Chin-Ho | Li, Rong-Tao | Li, Hong-Mei
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 IC₅₀ 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 IC₅₀ at 3.86 μg/mL.
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