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Studies on the Hepatoprotective Activity of Kinsenoside and the Synthesis of Its Fully Acetylated Derivative

Author: HuGuangHua
Tutor: ZhangYongHui;JiangFengChao
School: Huazhong University of Science and Technology
Course: Of Pharmacy
Keywords: Gold line lotus Active ingredient Hepatoprotective Synthesis
CLC: R285
Type: Master's thesis
Year: 2009
Downloads: 128
Quote: 0
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Abstract


Gold line lotus (Anoectochilus roxburghii (Wall.) Lindl.), Is the Orchidaceae open lips and blue is a perennial herb. Gold line lotus is a traditional precious herbs, liver, lowering blood sugar, blood pressure, diuretic, anti-tumor effects, and non-toxic side effects, safe to use. More civil with the treatment of diabetes, hepatitis B, high cholesterol, cancer and other diseases. The main component of glycosides, alkaloids, steroids, flavonoids, taurine, amino acids, trace elements and other. Studies have shown that gold line lotus direct effect on the liver cell membrane, to protect the integrity of the liver cell membrane, prevent harmful material damage the liver cell membrane and prevent lesions of the liver cell necrosis. Gold line lotus Origin forest vegetation soil suffered varying degrees of damage, the scarcity of natural resources, is now endangered. Gold line lotus folk wider application, efficacy, and the actual situation of scarcity of resources, this study mainly in lotus glycosides, gold wire and gold wire lotus glycosides full-acetyl compounds protect liver enzymes activity screening under the guidance and found gold wire lotus glycosides acetylated derivative activity is stronger than gold line lotus glycosides, lotus glycosides acetyl compounds, gold wire fully synthetic. Content and methods of this study include: 1 gold wire Lin glycosides, and its wholly-acetyl compounds active research mainly through experimental investigation gold line lotus glycosides and its wholly-acetyl compounds protective effect on carbon tetrachloride-induced liver injury in mice by intraperitoneal injection of 0.125? L4 oil solution modeling to study the impact of different doses of the two compounds in ATS liver injury in mice serum ALT indicators. The results showed that the two compounds with different doses of ALT, AST index values ??were lower than the model group, with a significant dose-dependent histopathological examination also showed that the gold line lotus glycosides and its wholly-acetyl compounds doses of liver cell swelling, necrosis and inflammatory cell infiltration and model group, compared with a significant improvement. Compared with silymarin group, the gold wire Lin glycosides acetyl compounds protect liver enzymes activity and silymarin, and stronger than the gold line lotus glycosides. 2. Of gold wire Lin glycosides full acetylation product synthesis by our group has been committed to natural medicine research to find the active ingredient, the general the track separation methods are based on the active ingredient, our group by the chemical composition of the gold line lotus found glycoside activity Anoectochilus Preferably, in order to obtain sufficient quantity sample pharmacological studies and structural transformation of the experimental project its chemical synthesis. Based on the idea of ??reverse synthesis, gold wire Lin glycosides acetyl matter theory can be divided into two parts: aglycone and sugar moiety, aglycone part we were lactose and maltodextrin starting materials synthesized by three different The synthetic pathway for the aglycone portion Finally, we select the method 3 is a more ideal synthesis method, the maltodextrin feedstock peroxide hydroxy cumene catalyst, microwave irradiation participate in the reaction, One-Pot Synthesis of (S) - 3 - hydroxy-gamma-butyrolactone. Sugar moiety, we synthesized two sugar intermediate donor, respectively, 1 - bromo-2, 3, 4, 6 - tetra-O-acetyl-alpha-D-glucose and 2, 3, 4, 6 - 4 - O-acetyl the groups-alpha-D-glucose trichloroacetyl imide ester, wherein the glucose trichloroacetimidate sugar ester intermediates were used two methods for the synthesis method is more desirable, i.e. glucose bromopeptide taking off the anomeric carbon reaction as a starting material, so that the reaction yield and purity are improved. Then we also carried out the synthesis of the target compound exploration of the two methods, respectively, 1 - bromo-2, 3, 4, 6 - tetra-O-acetyl-alpha-D-glucose and 2, 3, 4, 6 - tetra-O-acetyl-alpha-D-glucose trichloroacetimidate ester sugar intermediate glycosidation reaction, the ideal final Route 2, TMSOTf glucose trichloroacetyl imide esters and glycosides $ hydroxy successfully connected to the synthesis of the final product on physicochemical properties and spectral data are consistent with the literature, provides the basis for the gold wire Lin glycosides Structural Modification.

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