黄酮类化合物和抗生素类药物的高效液相色谱检测技术研究
摘要
化学发光(chemiluminescence，简称CL)是化学反应的反应物或是生成物吸收了反应过程中释放的化学能，电子由基态跃迁至激发态，再由激发态返回基态时所产生的光辐射，根据化学发光反应在某一时刻的发光强度或发光总量来确定反应中的响应组分含量的分析方法叫做化学发光分析法。此法具有灵敏度高、线性范围宽、仪器简单、分析快速等优点。化学发光检测亦可与高效的分离手段如：高效液相色谱、毛细管电泳等联用，有效克服化学发光分析法固有的选则性差的缺点，成为一种有效的痕量分析方法，在环境科学、药物分析及生命科学等领域中具有广泛的应用前景。将具有高分离效率的高效液相色谱(HPLC)分离法与具有高灵敏度的化学发光分析法相结合已引起了国内外分析化学家的极大关注，成为从上个世纪80年代末至今分析化学研究的一大热点。毫无疑问，高效液相色谱分离技术与化学发光检测法的联用将在生物、临床医学、环境检测、药物分析等领域得到愈来愈广泛的应用。
本文包括两个部分。第一部分是综述，这部分结合化学发光分析法，评述了近十年高效液相色谱及其与化学发光柱后检测技术在黄酮类化合物和抗生素类药物中的应用。
第二部分是研究报告。第一节是高效液相色谱化学发光检测法在黄酮类化合物中的研究。详细研究了在碱性条件下，铁氰化钾氧化鲁米诺产生化学发光，而漆黄素能增强发光信号，从而建立了简单、灵敏、快速测定漆黄素高效液相色谱化学发光新方法。
第二节是高效液相色谱检测技术在抗生素类药物中的应用。研究了在C_(18)反相色谱柱，采用UV-VIS检测器，磷酸二氢钾-磷酸(pH 4．0)缓冲液为流动相于211 nm下检测新型抗生素中间体S-AMOSA；并研究了FMOC柱前衍生法测定S-AMOSA，以9-氯甲酸芴甲酯(FMOC)为衍生剂，与S-AMOSA发生衍生反应后，反相高效液相色谱法测定的方法。本法快速、简单、准确度高，适用于测定新型抗生素中间体S-AMOSA。
1．漆黄素的高效液相色谱化学发光检测法研究
本文研究发现，漆黄素在碱性条件下能大大增强Luminol-K_3F_e(CN)_6化学发光强度，基于此，并结合HPLC分离技术，建立起漆黄素的HPLC-CL分析新方法。在C_(18)反相键合相色谱柱，甲醇为流动相的条件下，实现了对人体血清中的漆黄素的分离与测定，方法的线性范围为7．7×10~(-6)～9．6×10~(-4)g／L，相关系数为r=0．9998，检出限为2．7×10~(-7)g／L，RSD为2．41％(n=11)。实验表明该法快速、简单、准确度高，适用于漆黄素的测定。
2．RP-HPLC法测定新型抗生素中间体S-AMOSA
建立快速、灵敏的反相高效液相色谱法测定新型抗生素中间体S-AMOSA的浓度。采用岛津SPD-6AV检测器，Hypersil C_(18)(150 mm×4．6 mm，5．0μm)色谱柱，磷酸二氢钾-磷酸(pH 4．0)缓冲液为流动相，柱温为室温时，于211 nm波长处以外标法测定。结果表明S-AMOSA在4．8～120μg／mL的范围内呈良好的线性关系(r=0．9999)。方法回收率为98．0％～103．0％。实验表明该法简便、快速、有效，重现性好，首次用于抗生素中间体S-AMOSA的测定，取得了很好的结果。
3．FMOC柱前衍生-高效液相色谱法测定新型抗生素中间体S-AMOSA
建立FMOC柱前衍生测定新型抗生素中间体S-AMOSA的高效液相色谱方法。以9-氯甲酸芴甲酯(FMOC)为衍生剂，与S-AMOSA发生衍生反应后，反相高效液相色谱法测定。以甲醇-水为流动相，C_(18)柱为分离柱，紫外可见检测器(263 nm)检测。结果表明S-AMOSA在0．01125～0．36 g／L的范围内呈良好的线性关系(r=0．9996)。方法回收率为97．78％～102．33％。实验表明该法快速、简单、准确度高，适用于新型抗生素中间体S-AMOSA的测定。
4．RP-HPLC法分离测定动物肝脏中多种维生素的含量
建立了一种同时测定4种水溶性维生素的高效液相色谱方法。采用Shimadzu VP-ODS(150mm×4．6 mm i．d．，5．0μm)色谱柱，以甲醇-0．01 mol／L磷酸氢二钾缓冲溶液梯度洗脱，在波长为267 nm处进行检测。维生素C、B_1、B_6和B_2分别在22．3～116．0，2．4～152．5，2．2～340．0，1．7～272．0μg／mL呈良好的线性关系，相对标准偏差为(n=6)1．14％～1．56％，平均回收率在98．6～102．3％范围以内。实验表明该方法可用于同时测定动物肝脏中维生素C、B_1、B_6和B_2的含量。
Chemiluminescence (CL) is defined as the emission of light from an electronically excited species which produced during the course of a chemical reaction, and is observed when the electronically excited product or intermediate formed decays to the ground state with a photon emitted. Due to its high sensitivity, wide linear range, rapidity, simplicity and so on, the chemiluminescence method can he combined with other separate method especially electrophoresis and high performance liquid chromatogram etc, which can avoid the disadvantage of CL (poor selectivity). This has been successfully applied in environmental science, pharmaceutical science,and life science, and has become one of the most powerful techniques in analytical chemistry. The chemiluminescence (CL) detection system combined with HPLC separation method can offer excellent analytical selectivity and sensitivity. No doubtable, chemiluminescence linked to HPLC will be widely applied in biological science, clinical science environmental science and pharmaceutical science.
The thesis consists of two parts. One is a review related to the application of HPLC with post-column chemiluminescence detection to flavones and antibiotics. Emphasis is taken on the development in the recent ten years.
The other is a research report which is composed of 4 components as follows. 1) The determination of Fisten in human serum by high performance liquid chromatography with chemiluminescence detection; 2) RP-HPLC determination of a new intermediate S-AMOSA of antibiotic; 3) Determination of S-AMOSA by high performance liquid chromatography after derivatization with 9-flurenylmethyl chloroformate; 4) Determination of the water soluble vitamins in animal livers by revise-phase high performance liquid chromatography.
1. The Determination of Fisten in Human Serum by High Performance Liquid Chromatography with Chemiluminescence Detection
A novel chemiluminescence determination of fisetin in human serum by high performance liquid chromatographic (HPLC) separation with chemiluminescence detector was described. The signal produced by the chemiluminescent reaction (CL) between luminol and ferricyanide was greatly increased in presence of fisetin. The linear range of fisetin concentration is 7.7×10~(-6)～9.6×10~(-4)g/L (r=0.9998) and the detection limit is 2.7×10~(-7)g/L. The method is reliable, accurate and suitable to the determination of fisetin.
2. RP-HPLC Determination of a New Intermediate S-AMOSA of Antibiotic
A rapid and sensitive RP-HPLC method was established for the determination of intermediate S-AMOSA of antibiotic. A Hypersil C_(18)(4.6 mm×150 mm, 5.0μm) column and SPD-6AV detector were used. The mobile phase was composed of phosphate buffer. Detection wave length was 211 nm and the temperature of the column was room one. The linearity of the calibration curve was well correlated(r=0.9999) in the range of 4.8～120μg/mL. The recovery was 98.0%～103.0%. The method has been successfully applied to the determination of S-AMOSA, which was proved to be accurate, simple, effective and reproductive.
3. Determination of S-AMOSA by High Performance Liquid Chromatography after Derivatization with 9-flurenylmethyl Chloroformate
Objective to establish a high performance liquid chromatographic (HPLC) method for the determination of S-AMOSA. After derivatization with FMOC, S-AMOSA was separated and quantified by HPLC. A mobile phase of methanol-H_2O, an analytical column of C_(18) and UV-VIS detection wavelength of 263 nm were used in the study. The linearity of the calibration curve was well correlated(r=0.9996) in the range of 0.01125～0.36 g/L. The recovery was 97.78%～102.33%. The method is reliable, accurate and suitable to the determination of S-AMOSA.
4. Determination of the Water Soluble Vitamins in Animal Livers by Revise-phase High Performance Liquid Chromatography
To establish a method for assaying four water-soluble vitamins in animal livers by high performance liquid chromatographic method. Gradient elution was used for the separation of the four water-soluble vitamins in 12.5 min. The chromatographic conditions were: analytical column, Shimadzu VP-ODS(150 mm×4.6 mm i.d., 5.0μm); column temperature, ambient; mobile phase with gradient elution, 0.01 mol/L potassium dihydrogen phosphate buffer(pH6.2)/methanol from 13: 87 to 28: 72 in 12.5 min; flow rate, 1.2 mL/min. The standard curve of VitC, VitB_1, VitB_6, VitB_2 were linear in the concentration range of 22.3～116.0 , 2.4～152.5 , 2.2～340.0 , 1.7～272.0μg/mL respectively. The average of recovery of VitC, VitB_1, VitB_6, VitB_2 was in the range of 98.6～102.3% and the RSD was 1.14%, 1.56%, 1.34%, 1.38%respectively. This method is accurate, simple, rapid and reproducible and can assay simultaneously for VitC, VitB_1, VitB_6, VitB_2 in animal livers.
本文包括两个部分。第一部分是综述，这部分结合化学发光分析法，评述了近十年高效液相色谱及其与化学发光柱后检测技术在黄酮类化合物和抗生素类药物中的应用。
第二部分是研究报告。第一节是高效液相色谱化学发光检测法在黄酮类化合物中的研究。详细研究了在碱性条件下，铁氰化钾氧化鲁米诺产生化学发光，而漆黄素能增强发光信号，从而建立了简单、灵敏、快速测定漆黄素高效液相色谱化学发光新方法。
第二节是高效液相色谱检测技术在抗生素类药物中的应用。研究了在C_(18)反相色谱柱，采用UV-VIS检测器，磷酸二氢钾-磷酸(pH 4．0)缓冲液为流动相于211 nm下检测新型抗生素中间体S-AMOSA；并研究了FMOC柱前衍生法测定S-AMOSA，以9-氯甲酸芴甲酯(FMOC)为衍生剂，与S-AMOSA发生衍生反应后，反相高效液相色谱法测定的方法。本法快速、简单、准确度高，适用于测定新型抗生素中间体S-AMOSA。
1．漆黄素的高效液相色谱化学发光检测法研究
本文研究发现，漆黄素在碱性条件下能大大增强Luminol-K_3F_e(CN)_6化学发光强度，基于此，并结合HPLC分离技术，建立起漆黄素的HPLC-CL分析新方法。在C_(18)反相键合相色谱柱，甲醇为流动相的条件下，实现了对人体血清中的漆黄素的分离与测定，方法的线性范围为7．7×10~(-6)～9．6×10~(-4)g／L，相关系数为r=0．9998，检出限为2．7×10~(-7)g／L，RSD为2．41％(n=11)。实验表明该法快速、简单、准确度高，适用于漆黄素的测定。
2．RP-HPLC法测定新型抗生素中间体S-AMOSA
建立快速、灵敏的反相高效液相色谱法测定新型抗生素中间体S-AMOSA的浓度。采用岛津SPD-6AV检测器，Hypersil C_(18)(150 mm×4．6 mm，5．0μm)色谱柱，磷酸二氢钾-磷酸(pH 4．0)缓冲液为流动相，柱温为室温时，于211 nm波长处以外标法测定。结果表明S-AMOSA在4．8～120μg／mL的范围内呈良好的线性关系(r=0．9999)。方法回收率为98．0％～103．0％。实验表明该法简便、快速、有效，重现性好，首次用于抗生素中间体S-AMOSA的测定，取得了很好的结果。
3．FMOC柱前衍生-高效液相色谱法测定新型抗生素中间体S-AMOSA
建立FMOC柱前衍生测定新型抗生素中间体S-AMOSA的高效液相色谱方法。以9-氯甲酸芴甲酯(FMOC)为衍生剂，与S-AMOSA发生衍生反应后，反相高效液相色谱法测定。以甲醇-水为流动相，C_(18)柱为分离柱，紫外可见检测器(263 nm)检测。结果表明S-AMOSA在0．01125～0．36 g／L的范围内呈良好的线性关系(r=0．9996)。方法回收率为97．78％～102．33％。实验表明该法快速、简单、准确度高，适用于新型抗生素中间体S-AMOSA的测定。
4．RP-HPLC法分离测定动物肝脏中多种维生素的含量
建立了一种同时测定4种水溶性维生素的高效液相色谱方法。采用Shimadzu VP-ODS(150mm×4．6 mm i．d．，5．0μm)色谱柱，以甲醇-0．01 mol／L磷酸氢二钾缓冲溶液梯度洗脱，在波长为267 nm处进行检测。维生素C、B_1、B_6和B_2分别在22．3～116．0，2．4～152．5，2．2～340．0，1．7～272．0μg／mL呈良好的线性关系，相对标准偏差为(n=6)1．14％～1．56％，平均回收率在98．6～102．3％范围以内。实验表明该方法可用于同时测定动物肝脏中维生素C、B_1、B_6和B_2的含量。
Chemiluminescence (CL) is defined as the emission of light from an electronically excited species which produced during the course of a chemical reaction, and is observed when the electronically excited product or intermediate formed decays to the ground state with a photon emitted. Due to its high sensitivity, wide linear range, rapidity, simplicity and so on, the chemiluminescence method can he combined with other separate method especially electrophoresis and high performance liquid chromatogram etc, which can avoid the disadvantage of CL (poor selectivity). This has been successfully applied in environmental science, pharmaceutical science,and life science, and has become one of the most powerful techniques in analytical chemistry. The chemiluminescence (CL) detection system combined with HPLC separation method can offer excellent analytical selectivity and sensitivity. No doubtable, chemiluminescence linked to HPLC will be widely applied in biological science, clinical science environmental science and pharmaceutical science.
The thesis consists of two parts. One is a review related to the application of HPLC with post-column chemiluminescence detection to flavones and antibiotics. Emphasis is taken on the development in the recent ten years.
The other is a research report which is composed of 4 components as follows. 1) The determination of Fisten in human serum by high performance liquid chromatography with chemiluminescence detection; 2) RP-HPLC determination of a new intermediate S-AMOSA of antibiotic; 3) Determination of S-AMOSA by high performance liquid chromatography after derivatization with 9-flurenylmethyl chloroformate; 4) Determination of the water soluble vitamins in animal livers by revise-phase high performance liquid chromatography.
1. The Determination of Fisten in Human Serum by High Performance Liquid Chromatography with Chemiluminescence Detection
A novel chemiluminescence determination of fisetin in human serum by high performance liquid chromatographic (HPLC) separation with chemiluminescence detector was described. The signal produced by the chemiluminescent reaction (CL) between luminol and ferricyanide was greatly increased in presence of fisetin. The linear range of fisetin concentration is 7.7×10~(-6)～9.6×10~(-4)g/L (r=0.9998) and the detection limit is 2.7×10~(-7)g/L. The method is reliable, accurate and suitable to the determination of fisetin.
2. RP-HPLC Determination of a New Intermediate S-AMOSA of Antibiotic
A rapid and sensitive RP-HPLC method was established for the determination of intermediate S-AMOSA of antibiotic. A Hypersil C_(18)(4.6 mm×150 mm, 5.0μm) column and SPD-6AV detector were used. The mobile phase was composed of phosphate buffer. Detection wave length was 211 nm and the temperature of the column was room one. The linearity of the calibration curve was well correlated(r=0.9999) in the range of 4.8～120μg/mL. The recovery was 98.0%～103.0%. The method has been successfully applied to the determination of S-AMOSA, which was proved to be accurate, simple, effective and reproductive.
3. Determination of S-AMOSA by High Performance Liquid Chromatography after Derivatization with 9-flurenylmethyl Chloroformate
Objective to establish a high performance liquid chromatographic (HPLC) method for the determination of S-AMOSA. After derivatization with FMOC, S-AMOSA was separated and quantified by HPLC. A mobile phase of methanol-H_2O, an analytical column of C_(18) and UV-VIS detection wavelength of 263 nm were used in the study. The linearity of the calibration curve was well correlated(r=0.9996) in the range of 0.01125～0.36 g/L. The recovery was 97.78%～102.33%. The method is reliable, accurate and suitable to the determination of S-AMOSA.
4. Determination of the Water Soluble Vitamins in Animal Livers by Revise-phase High Performance Liquid Chromatography
To establish a method for assaying four water-soluble vitamins in animal livers by high performance liquid chromatographic method. Gradient elution was used for the separation of the four water-soluble vitamins in 12.5 min. The chromatographic conditions were: analytical column, Shimadzu VP-ODS(150 mm×4.6 mm i.d., 5.0μm); column temperature, ambient; mobile phase with gradient elution, 0.01 mol/L potassium dihydrogen phosphate buffer(pH6.2)/methanol from 13: 87 to 28: 72 in 12.5 min; flow rate, 1.2 mL/min. The standard curve of VitC, VitB_1, VitB_6, VitB_2 were linear in the concentration range of 22.3～116.0 , 2.4～152.5 , 2.2～340.0 , 1.7～272.0μg/mL respectively. The average of recovery of VitC, VitB_1, VitB_6, VitB_2 was in the range of 98.6～102.3% and the RSD was 1.14%, 1.56%, 1.34%, 1.38%respectively. This method is accurate, simple, rapid and reproducible and can assay simultaneously for VitC, VitB_1, VitB_6, VitB_2 in animal livers.
引文
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