来自滇金丝桃的具有抗神经炎症活性的多种多环多异戊烯基酰基间苯三酚
Diverse polycyclic polyprenylated acylphloroglucinols with anti-neuroinflammatory activity from Hypericum beanii.
作者信息
Li Ya-Wei, Lu Wei-Jia, Zhou Xin, Zhang Chao, Li Xue-Yan, Tang Peng-Fei, Kong Ling-Yi, Xu Wen-Jun
机构信息
Jiangsu Key Laboratory of Bioactive Natural product Research and Skate Key Laboratory of Natural Medicines, School of Traditional Chinese Pharmacy, China Pharmaceutical University, Nanjing 210009, People's Republic of China.
Jiangsu Key Laboratory of Bioactive Natural product Research and Skate Key Laboratory of Natural Medicines, School of Traditional Chinese Pharmacy, China Pharmaceutical University, Nanjing 210009, People's Republic of China.
出版信息
Bioorg Chem. 2022 Oct;127:106005. doi: 10.1016/j.bioorg.2022.106005. Epub 2022 Jul 6.
A phytochemical investigation on the roots of Hypericum beanii resulted in the isolation of six new polycyclic polyprenylated acylphloroglucinols (PPAPs), hyperberlones A-F, along with fourteen known analogues. The structural characterization of these compounds was carried out by analyzing the HRESIMS data, 1D and 2D NMR spectroscopic data, electronic circular dichroism (ECD) calculations, and gauge-independent atomic orbital (GIAO) NMR calculations. Hyperberlone A (1) was a caged PPAP with a rare tricyclo[4.3.1.0]decane carbon skeleton. It was deduced to be biosynthetically generated from hyperbeanol C (8) through key Paternò-Büchi reaction, radical cascade cyclizations, and retro-aldol reaction. Compounds 4, 6, 7, 9, 14, and 16 exhibited significant nitric oxide (NO) production inhibitory effects in lipopolysaccharide (LPS)-induced BV-2 microglial cells with IC values of 6.11-25.28 μM. Moreover, compound 4 significantly decreased the expression of cyclooxygenase-2 (COX-2) and inducible nitric oxide synthase (iNOS) in LPS-induced BV-2 microglia, as well as the phosphorylation of JNK.
对长柱金丝桃根进行植物化学研究，从中分离出6个新的多环多异戊烯基酰基间苯三酚（PPAPs），即长柱金丝桃素A - F，以及14个已知类似物。通过分析高分辨电喷雾电离质谱（HRESIMS）数据、一维和二维核磁共振波谱数据、电子圆二色（ECD）计算以及独立于规范的原子轨道（GIAO）核磁共振计算，对这些化合物进行了结构表征。长柱金丝桃素A（1）是一种具有罕见三环[4.3.1.0]癸烷碳骨架的笼状PPAP。据推测，它是通过关键的帕特诺 - 比希反应、自由基级联环化和逆羟醛反应，由长柱金丝桃醇C（8）生物合成产生的。化合物4、6、7、9、14和16在脂多糖（LPS）诱导的BV - 2小胶质细胞中表现出显著的一氧化氮（NO）生成抑制作用，半数抑制浓度（IC）值为6.11 - 25.28 μM。此外，化合物4显著降低了LPS诱导的BV - 2小胶质细胞中环氧化酶 - 2（COX - 2）和诱导型一氧化氮合酶（iNOS）的表达，以及JNK的磷酸化水平。
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