胆木木质部中一个新的酚酸苷

A new phenolic acid glycoside isolated from the xylem of Nauclea offcinalis

为了研究胆木(Nauclea offcinalis)木质部正丁醇组分化合物及其生物活性,利用硅胶、Sephadex LH-20凝胶柱色谱等多种色谱学方法,对化合物进行了分离纯化,通过分析包括核磁共振和质谱等波谱数据结合理化性质鉴定了化合物的结构,分别采用pNPG法和MTT法测试了化合物的α-葡萄糖苷酶抑制和肿瘤细胞毒活性。从中分离鉴定了15个化合物:胆木酚苷A(1)、4-O-β-D-香草酸-6-O-香草酰基吡喃葡萄糖苷(2)、saccharumoside B(3)、1-O-香草酸-6-(3″,5″-二甲氧基没食子酰)-β-D-吡喃葡萄糖苷(4)、獐牙菜苷(5)、phoenixoside A(6)、杜仲树脂酚(7)、rel-5-(1 R,5 S-dimethyl-3 R,4 R,8 S-trihydroxy-oxa-6-oxobicyclo-[3,2,1]oct-8-yl)-3-methyl-2 Z,4 E-pentadienoic acid(8)、3,4-二甲氧基-肉桂酸(9)、反式肉桂酸(10)、3,4-二甲氧基苯基-β-D-吡喃葡萄糖苷(11)、3,4,5-三甲氧基苯酚-β-D-吡喃葡萄糖苷(12)、苯甲酸(13)、原儿茶酸(14)和1,3,5-三甲氧苯(15)。其中胆木酚苷A(1)为新化合物,化合物2~4和6~8均为首次从胆木中分离得到。活性筛选结果表明化合物3、7、8、13和14显示出弱的α-葡萄糖苷酶抑制活性,且所有化合物在测试浓度下无细胞毒活性。

To study the chemical constituents from the n-BuOH extraction of Nauclea offcinalis xylem and their biological activities.The n-BuOH extraction of N.offcinalis were separated with silica gel,Sephadex LH-20 and other chromatographic materials.The isolates’structures were identified by the analysis of NMR,MS and other physicochemical properties.And then,the pNPG and MTT methods were employed to evaluate theirα-glucosidase inhibitory and tumor cell cytotoxicity activities,respectively.Fifteen compounds were isolated and identified as naucleaphenol A(1),4-O-β-D-(6-O-vanilloylglucopyranosyl)-vanillicacid(2),saccharumoside B(3),1-O-(vanillicacid)-6-(3′′,5′′-dimethoxygalloyl)-β-D-glucopyranoside(4),swerosid(5),phoenixoside A(6),medioresinol(7),rel-5-(1 R,5 S-dimethyl-3 R,4 R,8 S-trihydroxy-7-oxa-6-oxobicyclo-[3,2,1]oct-8-yl)-3-methyl-2 Z,4 E-pentadienoic acid(8),3,4-dimethoxycinnamic acid(9),trans-cinnamic acid(10),3,4-dimethoxyphenyl-β-D-glucopyranoside(11),3,4,5-trimethoxyphenyl-β-D-glucopyranoside(12),p-hydroxybenzaldehyde(13),protocatechuic acid(14)and 1,3,5-trimethoxybenzene(15).Naucleaphenol A(1)is a new compound,and compounds 2-4,6-8 and 11 were isolated from N.offcinalis for the first time.The bioactivity result showed that compounds 3,7,8,11 and 13 presented weakα-glucosidase inhibitory activities,while all the compounds showed no cytotoxicity at the test concentration.