Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College , Huazhong University of Science and Technology , Wuhan 430030 , People's Republic of China.
Institute of Chinese Herbal Medicines, Hubei Academy of Agricultural Sciences , Enshi 445500 , People's Republic of China.
J Nat Prod. 2019 Jul 26;82(7):1849-1860. doi: 10.1021/acs.jnatprod.9b00095. Epub 2019 Jun 27.
Twenty-four grayanane diterpenoids (-) including 12 new ones (-) were isolated from . The structures of the new grayanane diterpenoids (-) were defined via extensive spectroscopic data analysis. The absolute configurations of compounds -, -, , and were established by single-crystal X-ray diffraction analysis, and electronic circular dichroism data were used to define the absolute configurations of auriculatols D () and E (). Auriculatol A () is the first example of a 5,20-epoxygrayanane diterpenoid bearing a 7-oxabicyclo[4.2.1]nonane motif and a ///-fused 5/5/7/6/5 pentacyclic ring system. Auriculatol B () is the first example of a 3α,5α-dihydroxy-1-β-grayanane diterpenoid. 19-Hydroxy-3--auriculatol B () and auriculatol C () represent the first examples of 19-hydroxygrayanane and grayan-5(6)-ene diterpenoids, respectively. Diterpenoids - showed analgesic activities in the writhing test induced by HOAc, and , , , , , and at a dose of 5.0 mg/kg exhibited significant analgesic effects (inhibition rates >50%). Grayanane diterpenoids grayanotoxins I () and IV () at doses of 0.2 and 0.04 mg/kg showed more potent analgesic activities than morphine.
二十四种格里烷二萜类化合物（-），包括 12 种新化合物（-），从 中分离得到。通过广泛的光谱数据分析，确定了新格里烷二萜类化合物（-）的结构。通过单晶 X 射线衍射分析确定了化合物 -、-、- 和 的绝对构型，并利用电子圆二色性数据确定了 auriculatols D () 和 E () 的绝对构型。Auriculatol A () 是第一个具有 7-氧杂双环[4.2.1]壬烷基序和 ///-稠合 5/5/7/6/5 五环系统的 5,20-环氧格里烷二萜类化合物。Auriculatol B () 是第一个具有 3α,5α-二羟基-1-β-格里烷二萜类化合物。19-羟基-3--auriculatol B () 和 auriculatol C () 分别代表 19-羟基格里烷和格里烷-5(6)-烯二萜类化合物的第一个例子。二萜类化合物 - 在 HOAc 诱导的扭体试验中表现出镇痛活性，而 、、、、、和 ，在 5.0 mg/kg 的剂量下，表现出显著的镇痛作用（抑制率>50%）。格里烷二萜类化合物 grayanotoxins I () 和 IV () ，在 0.2 和 0.04 mg/kg 的剂量下，表现出比吗啡更强的镇痛活性。
