【作者】 宋妍；

【导师】 李铣； 吴立军；

【作者基本信息】 沈阳药科大学 ， 天然药物化学， 2008， 硕士

【摘要】 留兰香为唇形科薄荷属植物留兰香（Mentha spicata L）的全草。其味辛、甘,性微温,具有和中理气、祛风散寒、消炎、止血、收敛之功效,用于治疗伤风感冒、胃气痛、鼻衄、目赤、疗疮热疥等症。历代本草对留兰香记述不多但均有提及。另外,根据我们前期的药效学研究结果,留兰香具有抗炎、止痛、抗溃疡、抗菌、抗病毒的功效。本研究是以“863国家重大科技专项——二类新药留兰香软胶囊治疗重症痔疮”的研究与开发为基础,以抗炎活性为指导,对留兰香水溶性部分进行了化学成分的研究,采用甲基化的方法处理水溶性部分样品以降低其极性,并应用萃取技术、大孔树脂D101、硅胶柱色谱、葡聚糖凝胶（Sephadex LH-20）色谱等多种分离手法对留兰香水溶性部分经甲基化后的化学成分进行了分离,共获得15个单体成分,通过理化性质和波谱数据分析(¹H-NMR、¹³C-NMR)并结合文献,鉴定了其中13个化合物的结构,分别为:柠檬酸三甲酯（trimethyl citrate,1）、原儿茶酸甲酯（methyl protocatechuate,2）、香草酸甲酯（methyl vanillate,3）、次黄嘌呤核苷（inosine,4）、尿苷（uridine,5）、胡萝卜苷（daucosterol,6）、香草醛（vanillin,7）、4-羟基苯甲酸正丁酯（n-butyl-4-hydroxybenzoate,8）、紫云英苷（astragalin,9）、丁香苷（syringin,10）、腺苷（adenosine,11）、芦丁（rutin,12）、槲皮素-3-O-β-D-吡喃葡萄糖苷（quercetin-3-O-β-D-pyranoglucoside,13）。将化合物1、2和3还原为有机酸,依次为柠檬酸（citric acid,1′）、原儿茶酸（protocatechuic acid,2′）、香草酸（vanillic acid,3′）,并经高效液相色谱验证这三个化合物均为甲基化后的产物。以上化合物1′、2′、3′及4-13中,化合物4、5和11为首次从薄荷属植物中分离得到的己知化合物;化合物1′、7-10、12-13为首次从留兰香中分离得到的已知化合物。本研究的意义在于:首次采用甲基化的化学转化方法来降低留兰香水溶性部分的极性,并利用多种色谱分离方法明确了甲基化产物的化学成分,进而发现了留兰香中更多的活性单体成分,也为后继开发提供了物质基础。更多还原

【Abstract】 Mentha spicata L.belongs to the genus Mentha（Lamiaceae）,which tastes pungent and sweet, and its natural character is a little warm.This plant has used to treat cold,peratodynia,rhinitis and furunculosis dieases,and it also showed the anti-inflammatory,hemostatic and pain-relieving properties by our previous work.Based on the previous work and guided by its bioactive results,the water-soluble fraction was dealt with the methylation method for reducing its polarity,then the products were isolated by silica gel column chromatography,macroporous resin D 101,Sephadex LH-20 and so on.Fifteen compounds were isolated and their structures were identified by physical and chemical characters and spectroscopic analysis(¹H-NMR,¹³C-NMR).Thirteen compounds were elucidated as trimethyl citrate（1）,methyl protocatechuate（2）,methyl vanillate（3）,inosine（4）,uridine（5）,daucosterol（6）, vanillin（7）,n-butyl-4-hydroxybenzoate（8）,astragalin（9）,syringin（10）,adenosine（11）,rutin（12）, quercetin-3-O-β-D-pyranoglucoside（13）.Respectively,among them,compound 1,2 and 3 were reverted and give to citric acid（1’）,protocatechuic acid（2’）,vanillic acid（3’）.Compounds 1-3 were proved to be the products of menthylation by means of HPLC analysis.So compound 1’,2’,3’ and from 4 to 13,compound 4,5 and 11 were firstly isolated from the Mentha.genus,and compound 1’, 7—10,12—13 were isolated from this plant for the first time.The menthylation reaction was firstly used to reduce the polarity of water-soluble fraction of Mentha spicata L.Many compounds were obtained from this methylated fraction.This result will helpful to confirm the natural basis of Mentha spicata L.for its bioactivities.更多还原