广藿香油中1个新的愈创木烷型倍半萜

A novel guaiane sesquiterpenoid from patchouli oil

目的研究广藿香油中化学成分的结构及神经细胞保护活性。方法利用硅胶柱、Sephadex LH-20柱、C18反相硅胶制备薄层色谱及半制备HPLC等方法进行分离纯化,根据化合物的理化性质、MS、1D和2D NMR等波谱数据鉴定化合物的结构;进一步采用X单晶衍射法和计算ECD确定结构。运用MTT法测定化合物的神经保护活性。结果从广藿香挥发油中分离得到2个愈创木烷型倍半萜化合物,分别是(+)-(1S,4S,5S,7R,10R)-愈创木烷-5,15-环氧-11-烯-10-醇(1)、patchouliguaiol C(2)。结论化合物1是新化合物,命名为环氧愈创木醇。其C-5与C-15通过醚键相连形成五元环氧结构。神经细胞保护活性筛选结果显示,化合物2在50μmol/L浓度下对β淀粉样蛋白1-42(amyloidβ-protein,Aβ1-42)损伤人神经母细胞瘤细胞SH-SY5Y和H2O2损伤PC12神经细胞具有显著的保护作用,存活率分别是(79.57±4.33)%和(69.14±2.55)%。

Objective To investigate the chemical constituents from and their neuroprotective effects from patchouli oil.Methods The compounds were isolated and purified by column chromatographies over silica gel,Sephadex LH-20,ODS,preparative TLC,and semi-preparative RP-HPLC.Their structures were elucidated by physicochemical properties,MS,1 D and 2 D NMR spectra data.The absolute configuration of compound 1 was determined by X-single crystal diffraction method and ECD data.In vivo efficacy of neuroprotection was evaluated by the MTT method.Results Two guaiane sesquiterpenoids were obtained from the patchouli oil and their structures were identified as(+)-(1 S,4 S,5 S,7 R,10 R)-guaiacane-5,15-epoxy-11-ene-10-ol(1)and patchouliguaiol C(2).Conclusion Compound 1 is a new compound named epoxy guaiol,whose C-5 and C-15 are connected by ether bond to form a five-membered epoxy structure.In addition,the compound 2 shows significant neuroprotective effects on H2 O2 induced PC12 cell and Aβ1-42 injured SH-SY5 Y cell at 50μmol/L with maximal protection of(79.57±4.33)%and(69.14±2.55)%.