State Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Medical University, Guiyang 550014, People's Republic of China.
School of Pharmaceutical Sciences, Guizhou Medical University, Guiyang 550025, China.
Org Biomol Chem. 2022 Dec 21;21(1):140-146. doi: 10.1039/d2ob01851a.
Hyperpatone A (1), a highly oxidated polycyclic polyprenylated acylphloroglucinol (PPAP), along with a biosynthesized related PPAP (2) was isolated from under the guidance of LC-MS investigation. Architecturally, compound 1 represents the first PPAP with an unprecedented 8/6/5/6/5 pentacyclic skeleton and an intramolecular peroxy bridge, which might be derived from the [3.3.1]-type bicyclic polyprenylated acylphloroglucinol the critical Baeyer-Villiger oxidation, decarboxylation, and intramolecular cyclization. The structures were established by extensive spectroscopic analysis, ACD software calculation, and quantum chemical computations. A plausible biogenetic pathway of 1 and 2 was also proposed. Importantly, both compounds exhibited moderate cytotoxic activities against the HEL cell line with the IC values ranging from 10.2 to 19.2 μM. Moreover, compound 1 showed an inhibitory effect on NO production in lipopolysaccharide-stimulated RAW264.7 cells at a lower concentration of 5 or 1 μM.
从 中分离到了高度氧化的多环聚异戊二烯基酰基间苯三酚（PPAP）化合物 1（1）和一种生物合成的相关 PPAP（2），这是在 LC-MS 研究的指导下进行的。从结构上看，化合物 1 代表了第一个具有前所未有的 8/6/5/6/5 五环骨架和分子内过氧桥的 PPAP，这可能是由 [3.3.1]-型双环聚异戊二烯基酰基间苯三酚通过关键的 Baeyer-Villiger 氧化、脱羧和分子内环化而来。通过广泛的光谱分析、ACD 软件计算和量子化学计算确定了其结构。还提出了化合物 1 和 2 的可能生物合成途径。重要的是，这两种化合物对 HEL 细胞系均表现出中等的细胞毒性，IC 值范围为 10.2 到 19.2 μM。此外，化合物 1 在较低浓度 5 或 1 μM 时对脂多糖刺激的 RAW264.7 细胞中 NO 的产生具有抑制作用。
