A series of monosubstituted troxerutin esters have been synthesized by enzyme-catalyzed regioselective acylation of troxerutin in nonaqueous medium.Using divinyl dicarboxylates(CH_2=CH-OOC-(CH_2)_n-COO-CH=CH_2,n = 2,3...A series of monosubstituted troxerutin esters have been synthesized by enzyme-catalyzed regioselective acylation of troxerutin in nonaqueous medium.Using divinyl dicarboxylates(CH_2=CH-OOC-(CH_2)_n-COO-CH=CH_2,n = 2,3,4,7,8,11) featuring different chain length as acyl donors and alkaline protease from Bacillus subtilis as catalyst,troxerutin was regioselective acylated at B ethoxyl group.The results indicated that the regioselectivity of the enzyme-catalyzed acylation was not affected by the chain length o...展开更多
Troxerutin fatty acid esters were prepared using troxerutin and fatty acid vinyl esters as substrates in pyridine through enzymatic route. The structures of as-prepared compounds were identified by FT-TR, NMR, and ESI...Troxerutin fatty acid esters were prepared using troxerutin and fatty acid vinyl esters as substrates in pyridine through enzymatic route. The structures of as-prepared compounds were identified by FT-TR, NMR, and ESI-HRMS. Using alkaline protease(≥30 mg/mL) as enzyme, maximum yields reached 58% at 3:1(vinyl hexanoate to troxerutin) in pyridine(water content ≤1%). The yields gradually declined as chain length of acyl donors rose. The antioxidation abilities of the as-obtained compounds were confirmed by both DPPH free radical scavenging and potassium ferricyanide reduction methods. The antioxidation ability of troxerutin fatty acid esters was found lower than that of troxerutin. However, the logP values of troxerutin fatty acid esters varied from 0.15 to 1.94, suggesting that troxerutin fatty acid esters had better lipophilicity than troxerutin(logP =-2.12) when compared to their oil-water distribution coefficients. Overall, these findings look promising as reference for further development of future troxerutin.展开更多
[Objectives]This study aims to establish a simple,convenient,fast,low-cost,low-consumption and efficient method for quality control of troxerutin.[Methods]In NaAc-phosphate buffer at pH=8,troxerutin could react with C...[Objectives]This study aims to establish a simple,convenient,fast,low-cost,low-consumption and efficient method for quality control of troxerutin.[Methods]In NaAc-phosphate buffer at pH=8,troxerutin could react with Cu^2+to form complex,which had a characteristic absorption peak at 408 nm in the ultraviolet spectrum.The content of troxerutin could be determined indirectly by measuring the absorbance of the complex.[Results]Within the linear range of 27.82-74.19μg/mL,the absorbance of the complex has a good linear relationship with the concentration of troxerutin.The regression equation is A=0.0119C-0.1384(r=0.9991),and the detection limit is 1.59μg/mL.This method used to determine the content of troxerutin in samples from different manufacturers,and the recovery is 100.9%-102.7%.[Conclusions]The ultraviolet spectrophotometry is used in this experiment to indirectly determine the content of troxerutin by measuring the absorbance of troxerutin-Cu^2+complex,and the results are accurate,reproducible and highly precise.This method can be used for quantitative analysis of troxerutin.展开更多
Troxerutin(TRO)is a mixture of semi-synthetic flavonoids prepared by hydroxyethylation of rutin,and it is commonly used for the treatment of cerebrovascular diseases.The main active ingredient is trishydroxyethyl ruti...Troxerutin(TRO)is a mixture of semi-synthetic flavonoids prepared by hydroxyethylation of rutin,and it is commonly used for the treatment of cerebrovascular diseases.The main active ingredient is trishydroxyethyl rutin.The mother liquor of TRO contains a lot of TRO and other derivatives of hydroxyethylated rutin.In order to make full use of the mother liquor of TRO,an efficient method was developed for recovering high-purity TRO from mother liquor of TRO by combining silica gel column chromatography with semi-preparative liquid chromatography.In the silica gel column chromatographic separation,the ratio of silica gel to sample and eluent composition were investigated to obtain optimum separation effect.The results showed that when the ratio of silica gel to sample was 50,and acetone–ethyl acetate–water–glacial acetic acid(10:10:3:1,v/v/v/v)was used as the eluent,the separation effect of TRO and adjacent impurities was good.Moreover,150 g of TRO with a purity of 80%could be obtained from 1 kg of mother liquor of TRO by the silica gel column chromatographic separation,and the results were consistent with the quality standard of TRO raw material.Subsequently,the semi-preparative HPLC was performed,and 100 g TRO with a purity of up to 98%(w/w)was obtained.Meanwhile,tetrahydroxyethylrutin and tetrahydroxyethylquercetin with purity greater than 98%were obtained.This work proposed the separation and preparation of TRO with high-purity from the production waste of TRO for the first time,which had certain environmental benefits and economic benefits.展开更多
基金the Science and Technology hall of Henan Province(No.072300420070No.82102330014)China,for financially supported to this work.
文摘A series of monosubstituted troxerutin esters have been synthesized by enzyme-catalyzed regioselective acylation of troxerutin in nonaqueous medium.Using divinyl dicarboxylates(CH_2=CH-OOC-(CH_2)_n-COO-CH=CH_2,n = 2,3,4,7,8,11) featuring different chain length as acyl donors and alkaline protease from Bacillus subtilis as catalyst,troxerutin was regioselective acylated at B ethoxyl group.The results indicated that the regioselectivity of the enzyme-catalyzed acylation was not affected by the chain length o...
基金financially supported by Science and Technology Department of Henan Province (No. 132102310028)the Program for Innovative Research Team from Zhengzhou (No. 131PCXTD605)
文摘Troxerutin fatty acid esters were prepared using troxerutin and fatty acid vinyl esters as substrates in pyridine through enzymatic route. The structures of as-prepared compounds were identified by FT-TR, NMR, and ESI-HRMS. Using alkaline protease(≥30 mg/mL) as enzyme, maximum yields reached 58% at 3:1(vinyl hexanoate to troxerutin) in pyridine(water content ≤1%). The yields gradually declined as chain length of acyl donors rose. The antioxidation abilities of the as-obtained compounds were confirmed by both DPPH free radical scavenging and potassium ferricyanide reduction methods. The antioxidation ability of troxerutin fatty acid esters was found lower than that of troxerutin. However, the logP values of troxerutin fatty acid esters varied from 0.15 to 1.94, suggesting that troxerutin fatty acid esters had better lipophilicity than troxerutin(logP =-2.12) when compared to their oil-water distribution coefficients. Overall, these findings look promising as reference for further development of future troxerutin.
基金Basic Ability Enhancement Project for Young and Middle-aged Teachers in Colleges and Universities of Guangxi in 2017(2017KY0284)Guangxi Key Laboratory of Zhuang and Yao Ethnic Medicine(GXZYKF2019-7)Collaborative Innovation Center of Zhuang and Yao Ethnic Medicine[(2013)No.20].
文摘[Objectives]This study aims to establish a simple,convenient,fast,low-cost,low-consumption and efficient method for quality control of troxerutin.[Methods]In NaAc-phosphate buffer at pH=8,troxerutin could react with Cu^2+to form complex,which had a characteristic absorption peak at 408 nm in the ultraviolet spectrum.The content of troxerutin could be determined indirectly by measuring the absorbance of the complex.[Results]Within the linear range of 27.82-74.19μg/mL,the absorbance of the complex has a good linear relationship with the concentration of troxerutin.The regression equation is A=0.0119C-0.1384(r=0.9991),and the detection limit is 1.59μg/mL.This method used to determine the content of troxerutin in samples from different manufacturers,and the recovery is 100.9%-102.7%.[Conclusions]The ultraviolet spectrophotometry is used in this experiment to indirectly determine the content of troxerutin by measuring the absorbance of troxerutin-Cu^2+complex,and the results are accurate,reproducible and highly precise.This method can be used for quantitative analysis of troxerutin.
基金Shaanxi science and technology hall project(Grant No.2018JM7060)Provincial Key Discipline Construction Project of pharmacy of Xi’an Medical University(Grant No.2016YXXK08)。
文摘Troxerutin(TRO)is a mixture of semi-synthetic flavonoids prepared by hydroxyethylation of rutin,and it is commonly used for the treatment of cerebrovascular diseases.The main active ingredient is trishydroxyethyl rutin.The mother liquor of TRO contains a lot of TRO and other derivatives of hydroxyethylated rutin.In order to make full use of the mother liquor of TRO,an efficient method was developed for recovering high-purity TRO from mother liquor of TRO by combining silica gel column chromatography with semi-preparative liquid chromatography.In the silica gel column chromatographic separation,the ratio of silica gel to sample and eluent composition were investigated to obtain optimum separation effect.The results showed that when the ratio of silica gel to sample was 50,and acetone–ethyl acetate–water–glacial acetic acid(10:10:3:1,v/v/v/v)was used as the eluent,the separation effect of TRO and adjacent impurities was good.Moreover,150 g of TRO with a purity of 80%could be obtained from 1 kg of mother liquor of TRO by the silica gel column chromatographic separation,and the results were consistent with the quality standard of TRO raw material.Subsequently,the semi-preparative HPLC was performed,and 100 g TRO with a purity of up to 98%(w/w)was obtained.Meanwhile,tetrahydroxyethylrutin and tetrahydroxyethylquercetin with purity greater than 98%were obtained.This work proposed the separation and preparation of TRO with high-purity from the production waste of TRO for the first time,which had certain environmental benefits and economic benefits.
