[关键词]
[摘要]
目的 研究花椒Zanthoxylum bungeanum正丁醇部位化学成分及其抗氧化活性。方法 采用多种柱色谱和高效液相色谱(HPLC)等进行分离纯化,利用NMR等多种波谱技术鉴定化合物结构;运用ABTS+和DPPH自由基清除法对所得化合物进行抗氧化活性评价。结果 从花椒正丁醇部位分离得到1个新化合物和13个已知化合物,分别鉴定为4-O-(3',4'-亚甲二氧基肉桂酰基)-肉桂酸甲酯(1)、苔黑酚(2)、1-甲氧基-7R,8S-二羟基苯丙醇(3)、咖啡酸甲酯(4)、没食子甲酯(5)、3-甲基2-烯丁醇-1-葡萄糖苷(6)、腺苷(7)、紫花前胡苷(8)、blumenol C glucoside(9)、(6R,9S)-3-氧-α-紫罗兰醇-β-D-吡喃葡萄糖苷(10)、长寿花糖苷(11)、丁香树脂酚-4'-O-β-D-吡喃葡萄糖苷(12)、(+)-南烛木树脂酚(13)、异落叶松脂素(14)。ABTS+和DPPH自由基清除实验表明,化合物2、4、5和12~14具有抗氧化活性,其中化合物13和14的ABTS+自由基清除活性半数抑制浓度(IC50)分别为5.7和11.0 μmol/L,与阳性对照维生素C(Vc)的IC50(6.4 μmol/L)相当。化合物4、5和13的DPPH自由基清除活性IC50分别为61.2、19.8和101.0 μmol/L,与阳性对照Vc的IC50(53.0 μmol/L)相当。结论 化合物1为1个新化合物,命名为花椒酚A;其中化合物1~5、7~10和14首次从花椒属植物中分离得到,化合物12首次从花椒中分离得到。化合物2、4、5和12~14具有一定的抗氧化活性。
[Key word]
[Abstract]
Objective To study the constituents of n-butanol portion of Zanthoxylum bungeanum pericarps and their anti-oxidative effects. Methods A variety of column chromatography and HPLC were used for separation and purification, and the structure of the compounds was identified by NMR and other spectroscopy techniques. ABTS+ and DPPH radical scavenging methods were used to evaluate the antioxidant activity of the compounds. Results One new compound (1) and 13 known compounds (2-14) were isolated from n-butanol portion of Z. bungeanum pericarps. They were identified as methyl 4-O-(3',4'-methylenedioxy-cinnamoyl)-cinnamate (1), orcinol (2), 1-methoxy-7R,8S-dihydroxyl-phenylpropanol (3), methylcaffeate (4), methylgallate (5), 3-methyl-but-2-en-1-yl-β-D-glucopyranoside (6), adenosine (7), marmesinin (8), blumenol C glucoside (9), (6R,9S)-3-oxo-α-ionol-β-D-glucopyranoside (10), roseoside (11), syringaresinol-4'-β-D-glucoside (12), (+)-lyoniresinol (13), and isolariciresinol (14). ABTS+ and DPPH radical scavenging experiments showed that compounds 2, 4, 5, and 12-14 had antioxidant activity. The IC50of ABTS+ radical scavenging activities of 13 and 14 were 5.7 and 11.0 μmol/L, respectively, which were equivalent to the IC50 of positive control (Vc=6.4 μmol/L), and the IC50 of DPPH radical scavenging activities of 4, 5 and 13 were 61.2, 19.8, and 101.0 μmol/L, respectively, which were equivalent to the IC50 of Vc=53.0 μmol/L. Conclusion Compound 1 is a new compound named as bungphenol A. Compounds 1-5, 7-10, and 14 are isolated from the genus Zanthoxylum for the first time, and compound 12 is isolated from Z. bungeanum for the first time. Compounds 2, 4, 5, and 12-14 show antioxidant activities.
[中图分类号]
R284.1
[基金项目]
国家自然科学基金资助项目(81673325);甘肃省自然科学基金资助项目(20JR10RA061,20JR5RA570);烟台中科先进材料与绿色化工产业技术研究院科技创新项目(AMGCE020);中国科学院百人计划人才项目