马齿苋中水溶性有机酸和异喹啉生物碱化学成分及其生物活性研究

发布时间：2018-04-11 21:23

本文选题：马齿苋 + 化学成分　；参考：《山东大学》2017年硕士论文

【摘要】：马齿苋(Portulaca oleracea L.)为马齿苋科马齿苋属一年生草本植物,是药食两用中药,被中国历代药典收载,具有清热解毒、凉血止血、止痢功效。现代药理学研究表明,马齿苋具有抗菌、抗氧化、抗衰老、耐缺氧、降血糖、降血脂、抗痴呆、抗抑郁、松弛支气管平滑肌、抗炎及抗哮喘等多种药理作用。马齿苋中化学成分类型众多,包括有机酸、多糖、黄酮、香豆素、萜类、甾体和生物碱,但其活性成分并不十分清楚,缺乏深入的研究。有机酸和生物碱是马齿苋的两大类主要成分。本文主要对马齿苋中水溶性有机酸和异喹啉生物碱进行提取、分离和结构鉴定,并对其醌还原酶(quinone reductase,QR)诱导、抗炎和β2-肾上腺素受体(β2-adrenergic receptor,β2-AR)激动等活性进行研究。通过聚酰胺、硅胶、葡聚糖凝胶等柱色谱方法进行分离纯化,利用核磁共振波谱等数据鉴定结构。共分离鉴定了 38个化合物,分别为丁二酸(1)、丁二酸单甲酯(2)、L-苹果酸(3)、L-苹果酸-1-甲酯(4)、L-苹果酸-4-甲酯(5)、L-苹果酸二甲酯(6)、柠檬酸-6-乙酯(7)、L-柠檬酸-1-甲酯(8)、柠檬酸-1,5-二甲酯(9)、4-羟基-5-甲基-3-呋喃甲酸(10)、5-羟甲基糠酸(11)、硬脂酸(12)、L-焦谷氨酸(13)、环-(酪氨酸-亮氨酸)(14)、L-异亮氨酸(15)、(-)-dehydrovomifoliol(16)、(-)-epiloliolide(17)、3,4-二羟基苯乙醇(18)、丁二酰亚胺(19)、尿嘧啶(20)、柠檬酸(21)、5-羟基-吡喃酮-2-甲酸甲酯(22)、L-亮氨酸(23)、L-苯丙氨酸(24)、多巴胺(25)、2-磺酸-多巴胺(26)、(5)-(-)-3-(6,7-二羟基-1,2,3,4-四氢异喹啉-1-基)-丙酸乙酯(27)、马齿苋酰胺E(28)、1-甲基-6,7-二羟基-3,4-二氢异喹啉(29)、6,7-二羟基-3,4-二氢异喹啉(30)、(5)-去甲猪毛菜碱(31)、(R)-(+)-1-异丁基-6,7-二羟基-1,2,3,4-四氢异喹啉(32)、1-(5-羟甲基呋喃-2-基)-6,7-二羟基-3,4-二氢异喹啉(33)、1-(呋喃-2-基)-6,7-二羟基-3,4-二氢异喹啉(34)、2-(呋喃-2-甲基)-6,7-二羟基-3,4-二氢异喹啉(35)、(R)-(+)-1-苯甲基-6,7-二羟基-1,2,3,4-四氢异喹啉(36)、L-酪氨酸(37)、腺嘌呤(38)。其中化合物33-35为新异喹啉生物碱,27个化合物2、4-8、10、11、13、15-18、22、25-27、29-37为首次从马齿苋中分离得到。对化合物1-38的活性筛选发现,化合物16(6.25 μM)和18(12.5 μM)可提高Hepa lclc7细胞的QR诱导活性,QR诱导率分别为16%和29%,化合物1-15、17、19-21未显示出QR诱导活性;化合物18、25-36具有不同程度的抗炎作用,能够显著抑制脂多糖(lipopolysaccharide,LPS)诱导RAW264.7小鼠巨噬细胞NO释放,其中,化合物18、25、27、28、31、34 抗炎活性较强,其 EC50值分别为 45.42 μM、17.96 μM、36.33 μM、35.36 μM、58.71 μM、18.12 μM,化合物 1-17、19-21 未显示出抗炎活性;化合物25-36具有不同程度的β2-AR激动作用,其中,化合物34和36具有较强的β2-AR激动作用,并呈剂量依赖关系,其EC50值分别为5.125 μM和87.86 nM。由上可以看出,新的异喹啉生物碱34既具有较强的抗炎活性,又具有较强的β2-AR受体激动作用,其进一步的药理作用及构效关系有待深入研究。
[Abstract]:Portulaca oleracea L.)Purslane is an annual herb of the genus Portulaca. It is a dual-purpose Chinese medicine and food. It was collected by Chinese pharmacopoeia and has the effect of clearing away heat and detoxifying, cooling blood to stop bleeding and stopping dysentery.Modern pharmacological studies show that Portulaca oleracea has many pharmacological effects, such as antibacterial, anti-oxidation, anti-aging, anti-hypoxia, hypoglycemia, hypolipidemia, anti-dementia, antidepressant, relaxation of bronchial smooth muscle, anti-inflammation and anti-asthma and so on.There are many chemical constituents in Portulaca oleracea, including organic acids, polysaccharides, flavonoids, coumarins, terpenoids, steroids and alkaloids.Organic acids and alkaloids are two main components of Portulaca oleracea.In this paper, water-soluble organic acids and isoquinoline alkaloids from Portulaca oleracea were extracted, isolated and identified, and the activities of quinone reductase-induced, anti-inflammatory and 尾 _ 2-adrenergic receptor (尾 _ 2-ARR) were studied.Polyamide, silica gel and dextran gel were separated and purified by column chromatography. The structure was identified by NMR and other data.A total of 38 compounds were isolated and identified.L-tyrosine, adenine, adenine, and adenine.Compound 33-35 is a new isoquinoline alkaloid, and 27 compounds are isolated from Portulaca oleracea for the first time.The activity screening of compound 1-38 showed that compound 1666.25 渭 M) and compound 1812.5 渭 M) could increase QR-induced activity of Hepa lclc7 cells by 16% and 29%, respectively. Compound 1-15C171719-21 did not show QR-inducing activity, and compound 18C25-36 had different anti-inflammatory effects.Compounds 25-36 have different degrees of 尾 2-AR activation, among which compounds 34 and 36 have strong 尾 2-AR activation in a dose-dependent manner. Their EC50 values are 5.125 渭 M and 87.86 nm, respectively.It can be seen from above that the new isoquinoline alkaloid 34 has both strong anti-inflammatory activity and strong activation of 尾 2-AR receptor, and its further pharmacological action and structure-activity relationship need to be further studied.
【学位授予单位】：山东大学
【学位级别】：硕士
【学位授予年份】：2017
【分类号】：R284.1;R285

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