摘要
本论文共由三章组成。第一章采用活性追踪的方法对黄海棠、梭梭、槐花、槲栎4种植物进行化学成分的研究,共分离得到31个化合物,鉴定了其中的21个化合物；第二章对4种植物的不同溶剂提取物以及从中分离得到的部分化合物进行体外抗氧化和抑制α-葡萄糖苷酶活性研究,并对藤黄科金丝桃属植物黄海棠的提取物进行了体内降血糖活性评价；第三章,对沙漠地区梭梭属植物梭梭的化学成分、药理活性及其利用价值进行综述,以期对其进行更好的保护和合理利用。
第一章黄海棠、梭梭、槐花和槲栎的化学成分研究
一、近年来,金丝桃属植物提取物显示出的良好的抗抑郁和抗病毒活性引起人们的广泛关注。活性筛选发现,金丝桃属植物黄海棠具有抗氧化和α-葡萄糖苷酶抑制活性。我们在抗氧化和α-葡萄糖苷酶抑制活性指导下对河南产黄海棠进行了系统的化学成分研究,从中分离得到9个化合物并全部鉴定出来,其中化合物3,5,8,3’,4’-五羟基黄酮(4)和白桦酸(8)为首次从该植物中分离得到。
二、梭梭属植物,作为荒漠区中分布面积最广的一种典型荒漠植物,传统上外用于治疗昆虫叮咬,植物的灰烬内用对炎症有效,整个植物水煎剂可用于治疗各种神经紊乱。未见有对我国内蒙古梭梭属植物梭梭的化学成分的研究报道。我们从梭梭乙酸乙酯和甲醇提取物中分离得到10个化合物,已鉴定了其中的6个化合物,其中化合物槲皮素(SS-4)和Chikusetsusaponin Iva(SS-6)为首次从该属植物中分离得到。
三、在体外抑制α-葡萄糖苷酶活性的指导下,对河南产槐花进行系统的化学成分研究,共分离得到11个化合物,已鉴定了其中的5个化合物。
四、河南栎属植物资源丰富,除了传统的用材、橡实、栲胶三大用途外,还具有广泛的药理作用,为了对其进行更好的开发利用,对采自河南栾川地区的槲栎老叶进行系统的化学成分研究,但由于槲栎老叶中色素较多,对分离干扰大,从中分离得到1个化合物,为首次从该植物中分离得到。
第二章黄海棠、梭梭、槐花和槲栎的生物活性研究
一、采用DPPH、ABTS和FRAP3种方法综合评价3种植物不同溶剂提取物(黄海棠、梭梭、槲栎)的抗氧化活性,发现槲栎叶的抗氧化能力最强,黄海棠的抗氧化能力次之,梭梭也具有一定的抗氧化活性；采用DPPH微量法测定了从黄海棠中分离得到的9个单体化合物的抗氧化活性,其中槲皮素、槲皮素-3-O-β-D-葡萄糖苷、槲皮素-3-O-β-D-半乳糖苷、山奈酚具有强的抗氧化能力。
二、利用建立的α-葡萄糖苷酶抑制剂体外微量筛选模型,首次对黄海棠、梭梭、槐花、槲栎这四种植物的不同溶剂提取物及部分单体化合物进行酵母菌来源的α-葡萄糖苷酶抑制活性研究。其中槐花抑制α-葡萄糖苷酶活性最强,且抑制类型研究显示槐花不同提取物对a-葡萄糖苷酶抑制作用均属非竞争性抑制；槲栎和黄海棠抑制α-葡萄糖苷酶活性次之；梭梭的4个提取物,都具有一定的酶抑制活性。在考察的8个单体化合物中,槲皮素、山奈酚和熊果酸显示了强的抑制α-葡萄糖苷酶活性,其余化合物也具有一定的抑制活性,但较弱。
三、在对酵母菌来源的α-葡萄糖苷酶的抑制活性研究基础上,进一步对黄海棠提取物进行了哺乳动物来源的大鼠小肠糖苷酶抑制活性研究。结果显示黄海棠乙酸乙酯、甲醇提取物及化合物槲皮素和山奈酚具有较好的大鼠肠酶抑制活性,为黄海棠的降糖作用和机制提供新的实验和理论证据。
四、利用建立的四氧嘧啶诱导的糖尿病模型,首次对黄海棠进行体内降血糖活性研究。黄海棠乙酸乙酯和甲醇提取物不仅能显著降低糖尿病小鼠的血糖水平,还可以升高糖尿病小鼠血清中SOD的含量,降低血清中MDA的含量,并且具有一定的治疗血脂代谢异常的作用。
第三章沙漠地区梭梭属植物的研究概况
本章从化学成分、药理作用、生态及经济价值等方面对我国西北荒漠地区梭梭属植物进行概述,以期对其进行进一步的保护和开发利用。
This dissertation is composed of three chapters. The first chapter showed the isolation and identification of all kinds of compounds from Hypericum ascyron, Haloxylon ammodendron, Sophora japonica L. and Quercus aliena Blume by bioassay guide. Thirty-one compounds were isolated and twenty-one compounds were identified. The second chapter reported antioxidant andα-glucosidase inhibitory activity in vitro of extracts and compounds from H. ascyron, H. ammodendron, S. japonica L., Q. aliena Blume, and hypoglycemic effect in vivo of extracts from H. ascyron. In last chapter, the study progress of chemical constituent, pharmaceutical and utility value of the genus Haloxylon were summarized.
Chapter 1. The chemical constituents of Hypericum ascyron, Haloxylon ammodendron, Sophora japonica L. and Quercus aliena Blume
i. Recently, H. perforatum is used as a herbal medicine for the treatment of moderate depression, and this effect has inspired further investigations on secondary metabolites from Hypericum species. Bioassay guided fractionation of antioxidant and antihyperglycemic EtOAC and MeOH extract of H. ascyron in our study led to the isolation of nine known compounds. Compounds 4 and 8 were isolated from H. ascyron firstly.
ii. The genus Haloxylon as a typical desert plants is traditionally used as an external application to treat insect stings. The ash of the plant is used to treat internal ulcers. No phytochemical work has so far been reported on H. ammodendron collected from inner Mongolia. From EtOAC and MeOH extract of H. ammodendron, ten compounds were isolated, six compounds were identified. Compounds SS-4 and SS-6 were firstly obtained from the genus Haloxylon. iii. Bioassay guided fractionation of a-glucosidase inhibitory activity EtOAC and MeOH extract of S. japonica L. in our study led to the isolation of eleven compounds, and six compounds were identified.
iv. The genus quercus distribute widely in Henan province, and have a wide range of pharmacological effects. In order to develop the plant, we investigated the old leaves of Q. aliena Blume collected from Luanchuan of Henan province. But only one compound was isolated and identified asα-Glutenol for the first time from this plant, because the leaves of this plant contain large phenolic contents and xanthophylls interfered the separation.
Chapter 2. Bioassay of Hypericum ascyron, Haloxylon ammodendron, Sophora
japonica L. and Quercus aliena Blume
i. The antioxidant activities of different solvent extracts of H. ascyron, H. ammodendron and Q. aliena Blume were evaluated by the DPPH, ABTS and FRAP assay comprehensively.The antioxidant capacity of extracts from leaves of Q. aliena Blume was strongest, H. ascyron was second, and H. ammodendron also showed certain antioxidant activities. The activity of compounds from H. ascyron was screened by scavenging activity against DPPH radical with microplate assay. Quercetin, quercetin-3-O-β-D-galactoside, quercetin-3-O-β-D-glucoside and kaempferol exhibited strong activity against DPPH radical with IC50 value 6.94,24.02,24.02 and 14.78μg/mL respectively.
ii. For the first time, we assayed the inhibitory effect againstα-glucosidase of different solvent extracts and several compounds from H. ascyron, H. ammodendron, S. japonica L. and Q. aliena Blume in a 96-well plate. Petroleum ether, EtOAC, MeOH, and water soluble extracts from S. japonica L.showed stronger inhibitory effect against a-glucosidase, and all of them showed noncompetitive type model on a-glucosidase. The inhibitory effect of H. ascyron and Q. aliena Blume was slightly secondary to S. japonica L., and four extracts from H. ammodendron also showed certain inhibitory activities. In eight compounds assayed, quercetin, kaempferol and ursolic acid showed stronger inhibiting activity compared with acarbose as positive control.
iii. Based on the above study on H. ascyron, the inhibitory effect against rat intestinal a-glucosidase was evaluated furtherly. EtOAC and MeOH extracts and compounds quercetin and kaempferol from H. ascyron showed good inhibitory activity, which provided a new experimental and theoretical evidence for hypoglycemic effect and mechanism.
iv. Based on the antioxidant and a-glucosidase inhibitory activities of H. ascyron in vitro, hypoglycemic and antioxidant activities of EtOAC and MeOH extracts were investigated on normal and alloxan-induced diabetic mice in vivo for the first time. The results showed that EtOAC and MeOH extracts had hypoglycemic effect on alloxan-induced diabetic mice, lowered the blood lipid level, and inhibited the oxidant stress and oxidative damage to tissues.
Chapter 3. The study progress of chemical constituent, pharmaceutical and utility value of the genus Haloxylon
The study progress of chemical constituent, pharmaceutical and utility value of the genus Haloxylon were summarized.
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