天然产物研究与开发 ›› 2024, Vol. 36 ›› Issue (3): 415-422.doi: 10.16333/j.1001-6880.2024.3.005

• 研究论文 • 上一篇    下一篇

中麻黄的化学成分研究

范锡玲,曹彦刚,焦新棉,郑晓珂,冯卫生*   

  1. 河南中医药大学药学院 河南省中药开发工程技术研究中心,郑州 450046
  • 出版日期:2024-03-20 发布日期:2024-03-20
  • 基金资助:
    国家重点研发计划-中医药现代化研究重点专项(2019YFC1708800)

Chemical constituents from Ephedra intermedia

FAN Xi-ling,CAO Yan-gang,JIAO Xin-mian,ZHENG Xiao-ke,FENG Wei-sheng*   

  1. The Engineering and Technology Center for Chinese Medicine Development of Henan Province, School of Pharmacy,Henan University of Chinese Medicine,Zhengzhou 450046,China
  • Online:2024-03-20 Published:2024-03-20

摘要:

研究中麻黄(Ephedra intermedia Schrenk et C.A.Mey.)干燥草质茎的化学成分及其抗哮喘活性。应用硅胶柱色谱、Sephadex LH-20柱色谱、Toyopreal HW-40C柱色谱以及半制备型高效液相色谱等多种手段对中麻黄草质茎的50%丙酮提取物进行化学成分研究,从中分离鉴定了22个化合物,根据其理化性质和波谱学数据鉴定其结构,分别为4-甲氧基肉桂酸(1)、肉桂酸(2)、ω-hydroxypropioguaiacone(3)、threo-8S-7-methoxysyringylglycerol(4)、3-(2,4′-dihydroxy-3′,5′-dimethoxyphenyl)propanoic acid(5)、8-hydroxy-9-methyl-7-(4-hydroxy-3,5-dimethoxyphenyl)-7-propanone(6)、3-羟基-1-(4-羟基-3,5-二甲氧基苯基)-1-丙酮(7)、2-羟基-1-(4-羟基-3-甲氧基)苯基-1-丙酮(8)、异咖啡酸甲酯(9)、trans-syringin(10)、cis-syringin(11)、(4R)-4-hydroxy-4-(2-hydroxypropan-2-yl)cyclo-hex-1-ene-1-carboxylic acid(12)、7-羟基-α-松油醇(13)、去氢吐叶醇(14)、脱落酸(15)、黑麦草素内脂(16)、(E)-3-(3-hydroxybut-1-enyl)-2,4,4-trimethylcyclohexa-2,5-dienone(17)、3-(3′-hydroxybutyl)-2,4,4-trimethylcyclohexa-2,5-dienone(18)、对异丙基苯甲酸(19)、p-cymen-7-yl β-D-glucopyranoside(20)、acyclic 7-hydroxygeranic acid(21)、7,7-dimethylbicyclo[3.1.1]hept-2-ene-1-carboxylic acid(22),其中化合物3~6810~1417~192122为首次从该植物中分离得到,同时经体外抗哮喘活性筛选,结果显示化合物1114能够显著抑制β-氨基己糖苷酶的释放。

关键词: 麻黄属, 中麻黄, 结构鉴定, 抗哮喘活性

Abstract:

To study the chemical constituents of the herbaceous stems of Ephedra intermedia Schrenk et C.A.Mey.Twenty-two compounds were isolated from the 50% aqueous acetone extract of Ephedra intermedia by silica gel,sephadex LH-20 column chromatography,Toyopreal HW-40C column chromatography,as well as semi-preparative HPLC methods.Their structures were identified by spectral analysis as 4-methoxycinnamic acid (1),cinnamic acid (2),ω-hydroxypropioguaiacone (3),threo-8S-7-methoxysyringylglycerol (4),3-(2,4′-dihydroxy-3′,5′-dimethoxyphenyl)propanoic acid (5),8-hydroxy-9-methyl-7-(4-hydroxy-3,5-dimethoxyphenyl)-7-propanone (6),3-hydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)-1-propanone (7),2-hydroxyl-1-[4-hydroxy-3-methoxyphenyl(propan-1-one)] (8),methyl caffeate (9),trans-syringin (10),cis-syringin (11),(4R)-4-hydroxy-4-(2-hydroxypropan-2-yl)cyclo-hex-1-ene-1-carboxylic acid (12),7-hydroxyterpineol (13),dehydrovomifoliol (14),abscisic acid (15),loliolide (16),(E)-3-(3-hydroxybut-1-enyl)-2,4,4-trimethylcyclohexa-2,5-dienone (17),3-(3′-hydroxybutyl)-2,4,4-trimethylcyclohexa-2,5-dienone (18),4-isopropyl benzoic acid (19),p-cymen-7-yl β-D-glucopyranoside (20),acyclic 7-hydroxygeranic acid (21),7,7-dimethylbicyclo[3.1.1]hept-2-ene-1-carboxylic acid (22).And compounds 3-6,8,10-14,17-19,21 and 22 are isolated from this plant for the first time.The results of their anti-asthma activities showed that compounds 11,14 could significantly inhibit the release of β-aminohexosidase.

Key words: Ephedra;Ephedra intermedia, structural identification;anti-asthmatic activities

中图分类号:  R284.2