Chair of Pharmaceutical Biology, University of Regensburg, Faculty of Chemistry and Pharmacy, Regensburg, Germany.
Planta Med. 2021 Nov;87(14):1167-1183. doi: 10.1055/a-1617-7573. Epub 2021 Oct 1.
H NMR-guided fractionation of the petroleum ether extract of the aerial parts from yielded to the isolation of 19 polyprenylated polycyclic acylphloroglucinols. Structure elucidation based on 1D and 2D NMR spectroscopy together with high-resolution electrospray ionization mass spectroscopy revealed 14 acylphloroglucinols with a homoadamantane scaffold (1: -14: ), while 5 further compounds showed an adamantane skeleton (15: -19: ). Except for hookerione C (15: ), all isolated metabolites are hitherto unknown. While structurally-related metabolites have been isolated from other species, it is the first report of admantan and homoadamantan type acylphloroglucinols in section Jaub. & Spach (Hypericaceae). The isolated compounds have been tested in a crystal violet-based assay on their properties to reduce the proliferation of human microvascular endothelial cells compared to hyperforin as the positive control. They showed a moderate reduction of proliferation with IC values in the range ~ 3 - 22 µM, with the homoadamantane-based compounds 2: and 4: being the most active. In addition, inhibition of the TNF--induced ICAM-1 expression was determined for 1: - 5, 7,: and 10: - 12: . Substances 3: and 12: reduced the ICAM-1 expression significantly (to 46.7% of control for 3: , 62.3% for 12,: at 50 µM).
1H NMR 引导的石油醚提取物的馏分从 中得到了 19 个聚异戊二烯多环酰基间苯三酚的分离。基于 1D 和 2D NMR 光谱以及高分辨率电喷雾电离质谱的结构阐明揭示了 14 个具有同金刚烷骨架的酰基间苯三酚（1: -14: ），而另外 5 个化合物则显示出金刚烷骨架（15: -19: ）。除了 hookerione C（15: ）之外，所有分离出的代谢物都是以前未知的。虽然在其他 种中分离出了结构相关的代谢物，但这是首次在 Jaub. & Spach （藤黄科）的 节中报道了金刚烷和同金刚烷型酰基间苯三酚。所分离的化合物已在基于结晶紫的测定中进行了测试，以比较其抑制人类微血管内皮细胞增殖的特性，与作为阳性对照的 hyperforin 相比。它们表现出适度的增殖抑制，IC 值在 ~3-22μM 范围内，基于同金刚烷的化合物 2: 和 4: 最活跃。此外，还测定了 1: - 5、7: 和 10: - 12: 对 TNF--诱导的 ICAM-1 表达的抑制作用。化合物 3: 和 12: 显著降低了 ICAM-1 的表达（对于 3: 为对照的 46.7%，对于 12: 为 62.3%，在 50μM 时）。
