Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, Hubei Province, People's Republic of China.
Department of Pharmacy, Zhongnan Hospital of Wuhan University, Wuhan 430030, People's Republic of China.
Org Biomol Chem. 2022 Jun 22;20(24):4970-4975. doi: 10.1039/d2ob00562j.
(±)-Walskiiglucinol A (1a/1b), a pair of rearranged acylphloroglucinol derivatives with a new carbon skeleton, was obtained from . Compounds 1a/1b were the first examples of naturally occurring acylphloroglucinol derivatives possessing a unique 1-oxaspiro[4.4]nonane core bearing a new 5/5 ring system. Their planar and relative structures were identified by extensive spectroscopic analysis and NMR chemical shift calculations with DP4+ probability analysis, and their absolute configurations were determined by electronic circular dichroism (ECD) calculations. A plausible biogenetic pathway of 1a/1b was proposed in which the breakage of the C-2/C-3 linkage a retro-Claisen reaction and the cyclization between C-3 and C-1 were proposed as key steps. The isolates were evaluated for cytotoxic activities against a panel of cancer cell lines and anti-inflammatory activities against lipopolysaccharide (LPS)-induced NO production, and compounds 1a/1b showed moderate cytotoxic activities with IC values ranging from 9.72 to 36.75 μM.
(±)-Walskiiglucinol A（1a/1b）是一对具有新型碳骨架的重排酰基间苯三酚衍生物，从 中分离得到。化合物 1a/1b 是首例具有独特 1-氧杂螺[4.4]壬烷核心的天然存在的酰基间苯三酚衍生物，具有全新的 5/5 环系统。通过广泛的光谱分析和 NMR 化学位移计算，并结合 DP4+概率分析，确定了它们的平面和相对结构，通过电子圆二色性（ECD）计算确定了它们的绝对构型。提出了 1a/1b 的可能生物合成途径，其中 C-2/C-3 键的断裂和 C-3 与 C-1 之间的环化被认为是关键步骤。对这些分离物进行了针对一系列癌细胞系的细胞毒性活性和针对脂多糖（LPS）诱导的 NO 产生的抗炎活性评估，化合物 1a/1b 表现出中等的细胞毒性活性，IC 值范围为 9.72 至 36.75 μM。
