当前位置: X-MOL 学术Phytochemistry › 论文详情
Our official English website, www.x-mol.net, welcomes your feedback! (Note: you will need to create a separate account there.)
Grayanane diterpenoid glucosides as potent analgesics from Pieris japonica
Phytochemistry ( IF 3.8 ) Pub Date : 2020-03-01 , DOI: 10.1016/j.phytochem.2019.112234
Guijuan Zheng 1 , Pengfei Jin 1 , Lang Huang 1 , Na Sun 1 , Hanqi Zhang 1 , Hao Zhang 2 , Mingbo Yue 2 , Lingkui Meng 1 , Guangmin Yao 1
Affiliation  

A total of fifteen grayanane diterpenoid glucosides including eight undescribed ones, pierisjaponosides A-H, were isolated from the leaves of Pieris japonica (Thunb.) D. Don ex G. Don (Ericaceae). Their structures were established by extensive spectros copic techniques including HRESIMS and NMR, as well as chemical methods. The absolute configurations of pierisjaponosides A, B, and D were finally established by single-crystal X-ray diffraction with Cu Kα radiation. This is the first time to report the crystal structure of a 5,9-epoxygrayanane diterpenoid glucoside. Pierisjaponoside E represents the first example of a 9β-hydroxygrayan-1(10)-ene diterpenoid. All the isolated grayanane diterpenoid glucosides were evaluated for their analgesic activities in the acetic acid-induced writhing models in mice, and showed significant analgesic effects. Pierisjaponosides A and C-H, micranthanoside A, pieroside A, and craiobiosides A and B displayed significant analgesic effects with the writhe inhibition rates over 50% at a dose of 5.0 mg/kg. Pierisjaponoside E exhibited significant analgesic activities with the percentage inhibitions of 81.7%, 70.4%, and 52.1% at the doses of 5.0, 1.0, and 0.2 mg/kg, respectively. The preliminary structure-activity relationships of grayanane diterpenoid glucosides as potent analgesics were discussed, giving some clues to design novel analgesics.

中文翻译:

Grayanane 二萜葡萄糖苷作为来自粳稻的强效镇痛剂

从 Pieris japonica (Thunb.) D. Don ex G. Don (Ericaceae) 的叶子中分离出总共 15 种灰烷二萜糖苷,包括 8 种未描述的,pierisjaponosides AH。它们的结构是通过广泛的光谱复制技术(包括 HRESIMS 和 NMR)以及化学方法建立的。通过使用 Cu Kα 辐射的单晶 X 射线衍射,最终确定了芍药苷 A、B 和 D 的绝对构型。这是首次报道5,9-环氧grayanane二萜糖苷的晶体结构。Pierisjaponoside E 代表了 9β-hydroxygrayan-1(10)-ene 二萜的第一个例子。在醋酸诱导小鼠扭体模型中评估了所有分离的灰烷二萜糖苷的镇痛活性,并显示出显着的镇痛作用。Pierisjaponosides A 和 CH、micranthanoside A、pieroside A、craiobiosides A 和 B 表现出显着的镇痛作用,在 5.0 mg/kg 的剂量下抑制率超过 50%。Pierisjaponoside E 在 5.0、1.0 和 0.2 mg/kg 的剂量下表现出显着的镇痛活性,抑制百分比分别为 81.7%、70.4% 和 52.1%。讨论了作为强效镇痛药的灰烷二萜糖苷的初步构效关系,为设计新型镇痛药提供了一些线索。1% 的剂量分别为 5.0、1.0 和 0.2 mg/kg。讨论了作为强效镇痛药的灰烷二萜糖苷的初步构效关系,为设计新型镇痛药提供了一些线索。1% 的剂量分别为 5.0、1.0 和 0.2 mg/kg。讨论了作为强效镇痛药的灰烷二萜糖苷的初步构效关系,为设计新型镇痛药提供了一些线索。
更新日期:2020-03-01
down
wechat
bug