Highly functionalized cyclohexanone-monocyclic polyprenylated acylphloroglucinols from Hypericum perforatum induce leukemia cell apoptosis
Highly functionalized cyclohexanone-monocyclic polyprenylated acylphloroglucinols from Hypericum perforatum induce leukemia cell apoptosis
复制标题
贯叶连翘中的高功能化环己酮单环聚异戊二烯酰基间苯三酚诱导白血病细胞凋亡
DOI：
10.1039/c8qo01268g
复制
发表时间：
2019-03-21
影响因子：
5.4
通讯作者：
Zhang, Yonghui
中科院分区：
文献类型：
--
作者：
Guo, Yi;Tong, Qingyi;Zhang, Yonghui
从贯叶连翘茎叶中分离得到5个降解型环己酮-单环多戊烯基间苯三酚(C-MPAP)衍生物，分别为螺内酯A(1)、B(2)和超己酮C-E(3-5)。通过广泛的光谱分析和电子圆二色谱(ECD)计算确定了这些化合物的结构。化合物1和2是具有2-氧杂螺[4.5]正庚烷螺环骨架的天然C-MPAP的第一个例子。化合物5具有一个不寻常的十二氢-4H-氧代并[4，3-g]苯并呋喃环系。值得注意的是，化合物3和4通过激活caspase-3和降解PARP来诱导急性髓系白血病细胞株NB4和HL-60的凋亡。并对生物合成途径和生物活性进行了讨论。
Spirohypolactones A (1) and B (2) and hyperhexanones C-E (3-5), five degraded cyclohexanone-monocyclic polyprenylated acylphloroglucinol (C-MPAP) derivatives were isolated from the stems and leaves of Hypericum perforatum. The structures of these compounds were established by extensive spectroscopic analyses and electronic circular dichroism (ECD) calculations. Compounds 1 and 2 are the first examples of naturally occurring C-MPAPs possessing 2-oxaspiro[4.5]decane spirocyclic skeletons. Compound 5 featured an unusual dodecahydro-4H-oxocino[4,3-g]benzofuran ring system. Notably, compounds 3 and 4 induce apoptosis in the acute myeloid leukemia cell lines NB4 and HL-60 by the activation of caspase-3, and degradation of PARP. The proposed biosynthetic pathways and biological activities are also discussed.