Grayanane Diterpenoids from the Leaves of Rhododendron auriculatum and Their Analgesic Activities
文献类型： 外文期刊
作者： Sun, Na 1 ; Zheng, Guijuan 1 ; He, Meijun 2 ; Feng, Yuanyuan 1 ; Liu, Junjun 1 ; Wang, Meicheng 1 ; Zhang, Hanqi 1 ; Zhou 1 ;
作者机构： 1.Huazhong Univ Sci & Technol, Hubei Key Lab Nat Med Chem & Resource Evaluat, Sch Pharm, Tongji Med Coll, Wuhan 430030, Hubei, Peoples R China
2.Hubei Acad Agr Sci, Inst Chinese Herbal Med, Enshi 445500, Peoples R China
期刊名称：JOURNAL OF NATURAL PRODUCTS （ 影响因子：4.05； 五年影响因子：4.603 ）
ISSN： 0163-3864
年卷期： 2019 年 82 卷 7 期
页码：
收录情况： SCI
摘要： Twenty-four grayanane diterpenoids (1-24) including 12 new ones (1-12) were isolated from Rhododendron auriculatum. The structures of the new grayanane diterpenoids (1-12) were defined via extensive spectroscopic data analysis. The absolute configurations of compounds 2-4, 10-12, 14, and 16 were established by single-crystal X-ray diffraction analysis, and electronic circular dichroism data were used to define the absolute configurations of auriculatols D (8) and E (9). Auriculatol A (1) is the first example of a 5,20-epoxygrayanane diterpenoid bearing a 7-oxabicyclo[4.2.1]nonane motif and a trans/cis/cis/cis-fused 5/5/7/6/5 pentacyclic ring system. Auriculatol B (2) is the first example of a 3 alpha,5 alpha-dihydroxy-1-beta H-grayanane diterpenoid. 19-Hydroxy-3-epi-auriculatol B (6) and auriculatol C (7) represent the first examples of 19-hydroxygrayanane and grayan-5(6)-ene diterpenoids, respectively. Diterpenoids 1-24 showed analgesic activities in the writhing test induced by HOAc, and 2, 6, 10, 13, 19, and 24 at a dose of 5.0 mg/kg exhibited significant analgesic effects (inhibition rates >50%). Grayanane diterpenoids grayanotoxins I (19) and IV (24) at doses of 0.2 and 0.04 mg/kg showed more potent analgesic activities than morphine.
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