蜘蛛香中的环烯醚萜类成分及其抗流感病毒活性研究

Iridoids from Valeriana jatamansi and their related anti-influenza virus activity

目的研究蜘蛛香Valeriana jatamansi根及根茎的环烯醚萜成分及其抗流感病毒活性。方法采用正相硅胶柱色谱、羟丙基葡聚糖凝胶(SephadexLH-20)和高效液相色谱(HPLC)等色谱方法进行分离纯化,根据理化性质和NMR波谱技术对化合物进行结构鉴定,同时用流感A/WSN/33/2009(H1N1)病毒感染MDCK细胞模型评价化合物的抗流感病毒活性。结果从蜘蛛香的醋酸乙酯部位中共分离鉴定了20个环烯醚萜类成分,分别鉴定为缬草醛(1)、11-methoxyviburtinal(2)、去酰基缬草醛(3)、异缬草素(4)、去乙酰基异缬草素(5)、10-isovaleroxy-valtrathydrin(6)、jatamanvaltrate Q(7)、缬草醚F(8)、isovaltrate acetoxyhydrin(9)、jatamanvaltrate K(10)、rupesin B(11)、patriscadoid II(12)、jatamanvaltrate W(13)、patriscadoidI(14)、缬草醚D(15)、蜘蛛香素E(16)、jatamaninC(17)、(1S,3R,5S,7S,8S,9S)-1-methoxy-7-hydroxy-8-methyl-3,8-epoxy-Δ4,11-dihyronepetane(18)、(3S,4S,5S,7S,8S,9S)-3,8-ethoxy-7-dihydroxy-4,8-dimethylperhydrocyclopenta [c] pyran(19)、8,9-didehydro-7-hydroxy-dolichodial(20)。结论化合物5、9、12、14和20为首次从该植物中分离得到。化合物4和9对流感病毒具有抑制作用,半数抑制浓度(IC50)值分别为85.45、19.26μmol/L。

Objective To investigate the iridoids from the roots of Valeriana jatamansi and their anti-influenza virus activity. Methods The compounds were isolated and purified over several chromatographic methods, such as silica gel, Sephadex LH-20, HPLC and so on. Their structures were identified by the analysis of their physicochemical properties and NMR data. Their anti-influenza virus activity was evaluated by A/WSN/33/2009(H1 N1) infected MDCK cells. Results Twenty known iridoids(1-20) were isolated from the EtOAc-soluble fraction of 95% EtOH extract of V. jatamansi, and their structures were identified as baldrinal(1), 11-methoxyviburtinal(2), desacylbaldrinal(3), isovaltrate(4), deacetylisovaltrate(5), 10-isovaleroxy-valtrathydrin(6), jatamanvaltrate Q(7), valeriandoid F(8), isovaltrate acetoxyhydrin(9), jatamanvaltrate K(10), rupesin B(11), patriscadoid II(12), jatamanvaltrate W(13), patriscadoid I(14), valeriandoid D(15), valjatrate E(16), jatamanin C(17),(1 S,3 R,5 S,7 S,8 S,9 S)-1-methoxy-7-hydroxy-8-methyl-3,8-epoxy-Δ4,11-dihyronepetane(18),(3 S,4 S,5 S,7 S,8 S,9 S)-3,8-ethoxy-7-dihydroxy-4,8-dimethylperhydrocyclopenta [c] pyran(19) and 8,9-didehydro-7-hydroxy-dolichodial(20). Conclusion Compounds 5, 9, 12, 14, and 20 are isolated from V. jatamansi for the first time. Furthermore, compounds 4 and 9 exhibit anti-influenza A virus activity with IC50 values of 85.45 and 19.26 μmol/L.