花椒果皮正丁醇部分化学成分研究

Chemical constituents of n-butanol fraction of pericarps of Zanthoxylum bungeanum

目的对花椒Zanthoxylum bungeanum果皮正丁醇部分化学成分进行研究。方法利用大孔树脂柱色谱、硅胶柱色谱、ODS柱色谱、Sephadex LH-20凝胶柱色谱、半制备HPLC等方法进行分离纯化,并综合应用HR-ESI-MS、NMR、IR、CD等多种波谱方法确定化合物结构。结果从花椒果皮正丁醇部分分离得到25个化合物,分别鉴定为2α,3β-dihydroxy-3α-vanilloylmethyl-γ-lactone(1)、phellolactone(2)、香草酸(3)、异香草酸(4)、4-hydroxycryptone(5)、ZP-amide A(6)、ZP-amide B(7)、ZP-amide D(8)、马齿苋酰胺E(9)佛手柑内酯(10)、(±)-dorsteniol(11)、苔黑酚葡萄糖苷(12)、phloroacetophenone 4-O-β-D-glucopyranoside(13)、(1R,2R,4S)-trans-2-hydroxy-1,8-cineole-2-O-β-D-glucopyranoside(14)、(3S,6S)-6-ethenyltetrahydro-2,2,6-trimethyl-2H-pyran-3-yl-6-O-β-D-glucopyranoside(15)、trans-linalool-3,6-oxide-7-O-β-D-glucopyranoside(16)、betulabuside A(17)、大豆苷(18)、葛根素(19)、金丝桃苷(20)、槲皮素-3-O-β-D-葡萄糖苷(21)、槲皮素-3-O-β-D-鼠李糖苷(22)、扁蓄苷(23)、橙皮苷(24)和tamarixetin 7-rutinoside(25)。结论化合物1为新的γ-内酯类化合物,命名为异花椒戊内酯(isophellolactone),化合物1、2、9、11、13、14、17~19和22、23系首次从花椒属植物中分离得到,化合物5、10、15和24系首次从花椒中分离得到。

Objective To investigate the chemical constituents of pericarps of Huajiao(Zanthoxylum bungeanum).Method The n-butanol fraction of pericarps of Z.bungeanum was isolated and purified by macroporous resin column chromatography,silica gel column chromatography,Sephadex LH-20 gel column chromatography and semi-preparative HPLC.And their structures were elucidated by various spectroscopic methods,such as HR-ESI-MS,NMR,IR,CD,et al.Result A total of 25 compounds were isolated from the n-butanol fraction of pericarps of Z.bungeanum.They were identified as 2α,3β-dihydroxy-3α-vanilloylmethyl-γ-lactone(1),phellolactone(2),vanillic acid(3),isovanillic acid(4),4-hydroxycryptone(5),ZP-amide A(6),ZP-amide B(7),ZP-amide D(8),oleracein E(9),bergapten(10),(±)-dorsteniol(11),orcinol glucoside(12),phloroacetophenone 4-O-β-D-glucopyranoside(13),(1R,2R,4S)-trans-2-hydroxy-1,8-cineole-2-O-β-D-glucopyranoside(14),(3S,6S)-6-ethenyltetrahydro-2,2,6-trimethyl-2H-pyran-3-yl-6-O-β-D-glucopyranoside(15),trans-linalool-3,6-oxide-7-O-β-D-glucopyranoside(16),betulabuside A(17),daidzin(18),puerarin(19),hyperin(20),quercetin 3-O-β-D-glucopyranoside(21),quercetin 3-O-β-D-rhamnoside(22),avicularin(23),hesperidine(24)and tamarixetin 7-rutinoside(25).Conclusion Compound 1 is obtained as a newγ-lactone named as isophellolactone.Compounds 1-2,9,11,13-14,17-19 and 22-23 are isolated from Zanthoxylum for the first time.Compounds 5,10,15 and 24 are isolated from Z.bungeanum for the first time.