School of Pharmacy , Sungkyunkwan University , Suwon 16419 , Republic of Korea.
College of Korean Medicine , Gachon University , Seongnam 13120 , Republic of Korea.
J Nat Prod. 2020 Feb 28;83(2):354-361. doi: 10.1021/acs.jnatprod.9b00837. Epub 2020 Jan 28.
The absolute configuration and corrected NMR assignment of 17-hydroxycyclooctatin isolated from sp. M56 recovered from a nest of South African termites are reported. 17-Hydroxycyclooctatin is a unique tricyclic diterpene (C) consisting of a fused 5-8-5 ring system, and in this study, its structure was unambiguously determined by a combination of HR-ESIMS and 1D and 2D NMR spectroscopic experiments to produce corrected NMR assignments. The absolute configuration of 17-hydroxycyclooctatin is reported for the first time in the current study using chemical reactions and quantum chemical ECD calculations. The corrected NMR assignments were verified using a gauge-including atomic orbital NMR chemical shifts calculation, followed by DP4 probability. To understand the pharmacological properties of 17-hydroxycyclooctatin, a network pharmacological approach and molecular docking analyses were used, which also predicted its effects on human breast cancer cell lines. Cytotoxicity and antiestrogenic activity of 17-hydroxycyclooctatin were determined, and it was found this compound may be an ERα antagonist.
从南非白蚁巢中回收的 sp. M56 中分离得到的 17-羟基环辛烷的绝对构型和修正的 NMR 分配被报道。17-羟基环辛烷是一种独特的三环二萜（C），由一个融合的 5-8-5 环系统组成，在本研究中，通过高分辨电喷雾电离质谱（HR-ESIMS）和 1D 和 2D NMR 波谱实验的组合，明确确定了其结构，并对 NMR 分配进行了修正。使用化学反应和量子化学 ECD 计算，首次在本研究中报告了 17-羟基环辛烷的绝对构型。使用包含原子轨道的赝核核磁共振化学位移计算和 DP4 概率验证了修正的 NMR 分配。为了了解 17-羟基环辛烷的药理学特性，使用网络药理学方法和分子对接分析进行了研究，这也预测了它对人乳腺癌细胞系的作用。测定了 17-羟基环辛烷的细胞毒性和抗雌激素活性，发现该化合物可能是 ERα 拮抗剂。
