联用色谱在中药活性成分和生物样品分析中的应用研究
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摘要
近年来,“回归自然”的浪潮使中药备受关注,中药现代化的步伐越来越快。中药现代化进程中主要面临着两方面的问题:①中药成分复杂,并且成分之间相互影响和作用,同一成分化合物的分析结果可能会因母体药材或制剂配方的改变而受到不同程度的影响。故建立简单、可靠的中药及其复方中活性成分的分析方法是实现中药现代化的基本前提之一。②中药的有效成分是新药开发的先导,但是中药的药效成分与生物体内的代谢作用机理还不是十分清晰,因此建立灵敏、准确、快速生物样品中中药活性成分的测定分析方法,为进一步实现中药药代动力学的研究就显得尤为迫切。联用色谱技术的发展为中药的质量控制研究和中药药效物质基础研究提供了一个高效、可靠的分析方法。基于此,本文主要开展了以下几方面的创新性研究工作:
(1)采用分子印迹技术,以表儿茶素作为模板分子,丙烯酰胺为功能单体,乙烯基二甲基丙烯酸酯为交联剂,合成了表儿茶素分子印迹聚合物。用红外光谱和扫描电子显微镜表征了所合成的分子印迹聚合物。通过筛分,粒子尺寸在15和38μm之间的分子印迹聚合物被选为固相萃取吸附剂。结果表明:分子印迹聚合物对表儿茶素具有较高的分子识别能力和选择性。而空白聚合物却不具备这样的特性。在此基础上,把此分子印迹聚合物固相萃取小柱用于萃取茶叶提取物,分离富集其中的活性成分单体表儿茶素,获得了满意的结果。
(2)我们选取了栀子中的主要生物活性物质栀子甙为目标分析物,建立了用于分析栀子和栀子中药制剂清火栀麦片中的栀子甙的高效液相色谱-二极管阵列-质谱联用(HPLC-DAD-ESI/MS)分析方法。为了进一步更全面的对栀子中药制剂清火栀麦片进行质量控制,针对现有分析栀子中药制剂的缺陷,发展了简便、灵敏的高效液相色谱-二极管阵列-质谱联用(HPLC-DAD-ESI/MS)方法同时分析中药栀子复方制剂清火栀麦片及其原料药材中的活性物质脱水穿心莲内酯,穿心莲内酯和栀子甙。这三种活性成分主要用来作为清火栀麦片的质量控制的标志物。相对于其他分析方法,此方法提供了更多的定性、定量信息,同时能更全面的对中药复方制剂进行质量控制。
(3)针对现有的流动相体系不能对橘属中药中生物碱类和黄酮类两种不同色谱保留行为的活性物质同时分析测定的现状,且对生物碱类分析的流动相不适合于液质联用分析,我们采用挥发性全氟羧酸为离子对添加剂,解决了生物碱类物质辛氟林的低保留和峰拖尾,并考察了对黄酮类物质的色谱保留行为的影响,首次成功地建立了橘属中药中生物碱类和黄酮类物质同时分析的高效液相色谱-二极管阵列-质谱联用(HPLC-DAD-ESI/MS)分析方法。并且把这种方法应用于橘属中药青皮、陈皮、枳实和枳壳的全面质量控制中,获得满意的结果。
(4)以中药人参中的大分子量活性化合物人参皂甙为研究对象,研究了高锥孔电压对其电离效率,检测灵敏度的影响。建立了简单、灵敏的分析人参皂甙的高效液相色谱-质谱联用分析方法。高锥孔电压的采用能大大提高检测灵敏度,并且得到用于人参皂甙结构鉴定的加合离子和特征碎片离子。分析方法的线性范围在5-2×105之间,线性相关系数超过0.990,检测限达到pg级。该方法成功地应用于人参以及人参制剂中的人参皂甙的分析检测中,为其质量控制提供了更为简单、有效的检测方法。
(5)在本章中,建立了磁性纳米粒子-微波萃取的新方法用于中药中的有效成分的提取。这种新方法基于磁性纳米粒子能够吸收辐射的微波,把磁性纳米粒子作为中间媒介吸收微波。以中药黄芩的有效成分提取为例,磁性纳米粒子-微波萃取整个的萃取过程只需要40 s的微波辐射时间。而且,与一般的微波萃取相比,加入磁性纳米粒子的萃取效率更高,需要的有机溶剂更少。得到的提取物用高效液相色谱-质谱联用分析。本文所建立的方法的回收率在97.6–104.1%之间,相对标准偏差小于2.5%。黄芩苷,黄芩素,汉黄芩素的检测限分别为0.05,1.0和2.0 ng/mL。此方法成功地应用到了实际样品中有效成分地提取分析检测。
(6)为了保护动物,减少或取代动物实验,体外评估化学药品对细胞的毒性作用对于开发新药用于治疗各种各样的癌症具有十分重要的作用。尽管伊立替康对白血病、消化道和卵巢肿瘤具有较好的治疗作用,而对乳腺癌治疗的报道很少。本文首次以乳腺癌细胞MCF-7为模型,体外评估了伊立替康对乳腺癌细胞的毒性后,建立了快速、简单的HPLC-ESI/MS测定细胞中伊立替康及其代谢产物SN-38的方法,本法采用-80℃甲醇一步沉淀蛋白,线性范围可达3个数量级,线性相关系数大于0.9995,且方法特异性高,基质效应小,具有合适的精密度和灵敏度。该法成功地测定了伊立替康作用不同时间下的MCF-7细胞内的药物浓度,对抗肿瘤药物伊立替康的细胞药物代谢动力学进行了初浅地探讨。
(7)样品制备在HPLC的生物样品分析中是关键性的一步,经典的样品预处理包括蛋白质沉淀和药物萃取。此方法的缺点是大大增加了劳动量和分析时间,同时由于分析物在沉积蛋白质上的吸附而降低了回收率。直接进样技术在节约时间和劳力方面显示出了相当大的优越性。本工作应用简单、可靠的胶束液相色谱(micellar liquid chromatography ,MLC)法直接进样分析了生物样品中的隐丹参酮和丹参酮ⅡA。隐丹参酮和丹参酮ⅡA是传统中药丹参中主要的活性成分。由于它们有活跃的强而广药理性质,受到广泛关注。在实验中,采用C18色谱柱,流动相是pH 5的0.15 M SDS-8%正丁醇(n-butanol)溶液。与高有机溶剂消耗的HPLC相比,更为绿色。该方法准确度、精确度好、回收率高。并且也能成功地应用到丹参制剂中的隐丹参酮和丹参酮ⅡA分析检测,为丹参及其制剂中活性成分的药理,药代动力学研究研究提供了简单可靠的分析检测方法。
Recently, the traditional Chinese medicine (TCM) has attracted more and more attention for their therapeutic effects, which has accelerated the modernization process of TCM. Two aspects must be realized during the modernization of TCM. First, TCM is a complicated system, which contains a number of bioactive compounds. Herbal medicinal preparations are combined mixtures of herbal medicines. In order to ensure their maximal therapeutic effect, it is necessary and important to develop a simple and sensitive quality control method for TCM and the herbal medicinal preparations. Second, the bioactive compounds in TCM are the precursor of the new drug. However, the pharmacokinetics of the bioactive compounds is not very clear. So the method of determination of the bioactive compounds in biological sample is urgent to establish. The proposed method can applied to the pharmacokinetic studies. Based on the above situation, this thesis was concentrated on the quality control of the TCM and the determination of bioactive compounds in biological samples. The details are summarized as follows:
(1) Based on molecularly imprinted solid-phase extraction, a new molecularly imprinted polymer (MIP) was prepared by using epicatechin as the template molecule. The synthesized MIP was characterized by infrared spectroscopy and scanning electron microscopy and the MIP with 15-38μm particle size was selected as a solid-phase extraction (SPE) sorbent. It showed good selectivity and affinity for epicatechin in contrast to the structurally related compounds. The MIP cartridge enabled the selective extraction and preconcentration of epicatechin from tea samples.
(2) A rapid, specific, and reproducible high-performance liquid chromatography (HPLC)-photodiode array detection (DAD)-electrospray ionization mass spectrometry (ESI/MS) method has been developed for determination of geniposide in Gardenia jasminoides and its preparation. For full quality control of herbal medicinal preparations, the multiple bioactive compounds were analyzed. Dehydroandrographolide, andrographolide and geniposide are used as the markers to control the quality of such herbal preparations. A simple and sensitive high-performance liquid chromatographic (HPLC) method coupled with photodiode array detection (DAD) and electrospray mass spectrometry (ESI/MS) was developed to determine the three compounds simultaneously in the extracts of medicinal herbs and herbal preparations. Compared with the previously reported method, the proposed method is more simple and effective.
(3) The major active biological constituents in Citrus herbs are flavonoids and alkaloids, especially hesperidin, naringin and synephrine. However, they can not be detected in one run due to their different chromatographic retention behaviors. In this thesis, perfluorinated carboxylic acids, which are appropriate for MS detection due to their volatility, were used as ion pairing agents. The problems of the synephrine separation, such as band tailing and low retention were solved successfully. A new ion pairing chromatographic method was developed to exclude the most polar solute (synephrine) from the void volume and to maintain selectivity among the two other solutes (hesperidin, naringin). The two different kinds of the analytes were well separated in a single run using an isocratic eluent. The method is employed successfully to determine of hesperidin, naringin and synephrine in several Citrus herbs.
(4) High cone voltage was used to improve the quantification sensitivity of large molecular weight compounds in HPLC-ESI/MS, with ginsenosides as example. Investigations on the effect of cone voltage showed that within a voltage range of 3-?130 V, for all the ginsenosides tested, i.e., Rb1, Rb2, Rc, Rd, Re, Rf and Rg1, the increase of the applied cone voltage can significantly increase the sensitivity of the method. At the high cone voltage, both the molecular weight and structural information `were obtained from a single mass spectrum. It can also be used for isomer differentiation and structure determination of ginsenosides. Linear relationships between the peak area response and concentration were observed in the range of 50-2×10~5 ng/mL, with the correlation coefficients >0.99. The limits of detection reached down to pg for ginsenosides. The method was successfully applied to the determination of ginsenosides in commercial ginseng samples. It offers a simple and effective method to quality control of the ginseng.
(5) Based on the unique capacity of magnetite beads to absorb microwave radiation, a new magnetite nano-beads based microwave-assisted (MBMAE) technique was developed to improve the extraction of bioactive compounds from plant tissues, Scutellaria baicalensis Georgi and its herbal preparations were taken as application examples. In the presence of magnetite beads, 40 s microwave irradiation, was sufficient for carrying out the whole extraction process, Furthermore, it yields a higher extraction efficiency compared with the conventional microwave extraction technique and a lower consumption of organic solvent. The extracts were analyzed by high performance liquid chromatography–electrospray ionization mass spectrometry. The recovery of this method was in the range of 97.6–101.4% with relative standard deviation lower than 2.5 %. The limits of detection were 0.05, 1.0 and 2.0 ng/mL for wogonin, baicalein and baicalin, respectively. The present method has been successfully applied to the extraction determinination of wogonin, baicalein and baicalin in real samples. The results demonstrated the powerful application foreground of the proposed method in analysis of bioactive compounds contained in other Chinese herbal medicine.
(6) In order to protect the animal, decrease or replace the animal experiments, the in-vitro assessment of the toxicity of the drug using the cell mode is urgently. Many clinical researches showed that CPT-11 is useful in the treatment of many types of cancer, such as colorectal, ovarian and small cell lung cancers, while there are few reports about the treatment of breast tumors. Human breast cancer cell line MCF-7 was selected as a model to test the potent anticancer activity of CPT-11 in vitro. A a simple, rapid and sensitive method of liquid chromatography-electrospray mass spectrometry has been developed to assay the concentrations of anticancer drug irinotecan in human breast cancer cells. A single step protein precipitation with the -80℃methanol was used for sample preparation. High specificity and little matrix effects was obtained by this method. After exposure to irinotecan at different time interval, the intracellular drug concentration was successfully determined by the proposed method. The pharmacokinetics of irinotecan in human breast cancer cells was investigated.
(7) The sample pretreatment is the key step in the biological sample analysis by HPLC. The sample pretreatment contains the protein precipitation and the analyte extraction, thus the operation is relatively laborious and time-consuming. Meantime, the recovery is low. A simple and sensitive micellar liquid chromatography (MLC) method is proposed for the determination of Cryptotanshinone (CT) and tanshinone IIA (TS) in biological samples. No extraction step is required. A C18 column and a micellar mobile phase of 0.15 M SDS and 8% n-butanol were used. CT and TS are the major active compounds contained in traditional Chinese medicine Radix salvia miltiorrhiza (Danshen), with powerful pharmacological activities. Satisfactory recoveries in the biological matrices were achieved for CT and TS. Compared with the conventional reversed-phase chromatography method, the proposed MLC method is more sensitive, time-saving and less organic solvent is required. The proposed method could be used for the pharmacokinetic studies of the CT and TS.
(1)采用分子印迹技术,以表儿茶素作为模板分子,丙烯酰胺为功能单体,乙烯基二甲基丙烯酸酯为交联剂,合成了表儿茶素分子印迹聚合物。用红外光谱和扫描电子显微镜表征了所合成的分子印迹聚合物。通过筛分,粒子尺寸在15和38μm之间的分子印迹聚合物被选为固相萃取吸附剂。结果表明:分子印迹聚合物对表儿茶素具有较高的分子识别能力和选择性。而空白聚合物却不具备这样的特性。在此基础上,把此分子印迹聚合物固相萃取小柱用于萃取茶叶提取物,分离富集其中的活性成分单体表儿茶素,获得了满意的结果。
(2)我们选取了栀子中的主要生物活性物质栀子甙为目标分析物,建立了用于分析栀子和栀子中药制剂清火栀麦片中的栀子甙的高效液相色谱-二极管阵列-质谱联用(HPLC-DAD-ESI/MS)分析方法。为了进一步更全面的对栀子中药制剂清火栀麦片进行质量控制,针对现有分析栀子中药制剂的缺陷,发展了简便、灵敏的高效液相色谱-二极管阵列-质谱联用(HPLC-DAD-ESI/MS)方法同时分析中药栀子复方制剂清火栀麦片及其原料药材中的活性物质脱水穿心莲内酯,穿心莲内酯和栀子甙。这三种活性成分主要用来作为清火栀麦片的质量控制的标志物。相对于其他分析方法,此方法提供了更多的定性、定量信息,同时能更全面的对中药复方制剂进行质量控制。
(3)针对现有的流动相体系不能对橘属中药中生物碱类和黄酮类两种不同色谱保留行为的活性物质同时分析测定的现状,且对生物碱类分析的流动相不适合于液质联用分析,我们采用挥发性全氟羧酸为离子对添加剂,解决了生物碱类物质辛氟林的低保留和峰拖尾,并考察了对黄酮类物质的色谱保留行为的影响,首次成功地建立了橘属中药中生物碱类和黄酮类物质同时分析的高效液相色谱-二极管阵列-质谱联用(HPLC-DAD-ESI/MS)分析方法。并且把这种方法应用于橘属中药青皮、陈皮、枳实和枳壳的全面质量控制中,获得满意的结果。
(4)以中药人参中的大分子量活性化合物人参皂甙为研究对象,研究了高锥孔电压对其电离效率,检测灵敏度的影响。建立了简单、灵敏的分析人参皂甙的高效液相色谱-质谱联用分析方法。高锥孔电压的采用能大大提高检测灵敏度,并且得到用于人参皂甙结构鉴定的加合离子和特征碎片离子。分析方法的线性范围在5-2×105之间,线性相关系数超过0.990,检测限达到pg级。该方法成功地应用于人参以及人参制剂中的人参皂甙的分析检测中,为其质量控制提供了更为简单、有效的检测方法。
(5)在本章中,建立了磁性纳米粒子-微波萃取的新方法用于中药中的有效成分的提取。这种新方法基于磁性纳米粒子能够吸收辐射的微波,把磁性纳米粒子作为中间媒介吸收微波。以中药黄芩的有效成分提取为例,磁性纳米粒子-微波萃取整个的萃取过程只需要40 s的微波辐射时间。而且,与一般的微波萃取相比,加入磁性纳米粒子的萃取效率更高,需要的有机溶剂更少。得到的提取物用高效液相色谱-质谱联用分析。本文所建立的方法的回收率在97.6–104.1%之间,相对标准偏差小于2.5%。黄芩苷,黄芩素,汉黄芩素的检测限分别为0.05,1.0和2.0 ng/mL。此方法成功地应用到了实际样品中有效成分地提取分析检测。
(6)为了保护动物,减少或取代动物实验,体外评估化学药品对细胞的毒性作用对于开发新药用于治疗各种各样的癌症具有十分重要的作用。尽管伊立替康对白血病、消化道和卵巢肿瘤具有较好的治疗作用,而对乳腺癌治疗的报道很少。本文首次以乳腺癌细胞MCF-7为模型,体外评估了伊立替康对乳腺癌细胞的毒性后,建立了快速、简单的HPLC-ESI/MS测定细胞中伊立替康及其代谢产物SN-38的方法,本法采用-80℃甲醇一步沉淀蛋白,线性范围可达3个数量级,线性相关系数大于0.9995,且方法特异性高,基质效应小,具有合适的精密度和灵敏度。该法成功地测定了伊立替康作用不同时间下的MCF-7细胞内的药物浓度,对抗肿瘤药物伊立替康的细胞药物代谢动力学进行了初浅地探讨。
(7)样品制备在HPLC的生物样品分析中是关键性的一步,经典的样品预处理包括蛋白质沉淀和药物萃取。此方法的缺点是大大增加了劳动量和分析时间,同时由于分析物在沉积蛋白质上的吸附而降低了回收率。直接进样技术在节约时间和劳力方面显示出了相当大的优越性。本工作应用简单、可靠的胶束液相色谱(micellar liquid chromatography ,MLC)法直接进样分析了生物样品中的隐丹参酮和丹参酮ⅡA。隐丹参酮和丹参酮ⅡA是传统中药丹参中主要的活性成分。由于它们有活跃的强而广药理性质,受到广泛关注。在实验中,采用C18色谱柱,流动相是pH 5的0.15 M SDS-8%正丁醇(n-butanol)溶液。与高有机溶剂消耗的HPLC相比,更为绿色。该方法准确度、精确度好、回收率高。并且也能成功地应用到丹参制剂中的隐丹参酮和丹参酮ⅡA分析检测,为丹参及其制剂中活性成分的药理,药代动力学研究研究提供了简单可靠的分析检测方法。
Recently, the traditional Chinese medicine (TCM) has attracted more and more attention for their therapeutic effects, which has accelerated the modernization process of TCM. Two aspects must be realized during the modernization of TCM. First, TCM is a complicated system, which contains a number of bioactive compounds. Herbal medicinal preparations are combined mixtures of herbal medicines. In order to ensure their maximal therapeutic effect, it is necessary and important to develop a simple and sensitive quality control method for TCM and the herbal medicinal preparations. Second, the bioactive compounds in TCM are the precursor of the new drug. However, the pharmacokinetics of the bioactive compounds is not very clear. So the method of determination of the bioactive compounds in biological sample is urgent to establish. The proposed method can applied to the pharmacokinetic studies. Based on the above situation, this thesis was concentrated on the quality control of the TCM and the determination of bioactive compounds in biological samples. The details are summarized as follows:
(1) Based on molecularly imprinted solid-phase extraction, a new molecularly imprinted polymer (MIP) was prepared by using epicatechin as the template molecule. The synthesized MIP was characterized by infrared spectroscopy and scanning electron microscopy and the MIP with 15-38μm particle size was selected as a solid-phase extraction (SPE) sorbent. It showed good selectivity and affinity for epicatechin in contrast to the structurally related compounds. The MIP cartridge enabled the selective extraction and preconcentration of epicatechin from tea samples.
(2) A rapid, specific, and reproducible high-performance liquid chromatography (HPLC)-photodiode array detection (DAD)-electrospray ionization mass spectrometry (ESI/MS) method has been developed for determination of geniposide in Gardenia jasminoides and its preparation. For full quality control of herbal medicinal preparations, the multiple bioactive compounds were analyzed. Dehydroandrographolide, andrographolide and geniposide are used as the markers to control the quality of such herbal preparations. A simple and sensitive high-performance liquid chromatographic (HPLC) method coupled with photodiode array detection (DAD) and electrospray mass spectrometry (ESI/MS) was developed to determine the three compounds simultaneously in the extracts of medicinal herbs and herbal preparations. Compared with the previously reported method, the proposed method is more simple and effective.
(3) The major active biological constituents in Citrus herbs are flavonoids and alkaloids, especially hesperidin, naringin and synephrine. However, they can not be detected in one run due to their different chromatographic retention behaviors. In this thesis, perfluorinated carboxylic acids, which are appropriate for MS detection due to their volatility, were used as ion pairing agents. The problems of the synephrine separation, such as band tailing and low retention were solved successfully. A new ion pairing chromatographic method was developed to exclude the most polar solute (synephrine) from the void volume and to maintain selectivity among the two other solutes (hesperidin, naringin). The two different kinds of the analytes were well separated in a single run using an isocratic eluent. The method is employed successfully to determine of hesperidin, naringin and synephrine in several Citrus herbs.
(4) High cone voltage was used to improve the quantification sensitivity of large molecular weight compounds in HPLC-ESI/MS, with ginsenosides as example. Investigations on the effect of cone voltage showed that within a voltage range of 3-?130 V, for all the ginsenosides tested, i.e., Rb1, Rb2, Rc, Rd, Re, Rf and Rg1, the increase of the applied cone voltage can significantly increase the sensitivity of the method. At the high cone voltage, both the molecular weight and structural information `were obtained from a single mass spectrum. It can also be used for isomer differentiation and structure determination of ginsenosides. Linear relationships between the peak area response and concentration were observed in the range of 50-2×10~5 ng/mL, with the correlation coefficients >0.99. The limits of detection reached down to pg for ginsenosides. The method was successfully applied to the determination of ginsenosides in commercial ginseng samples. It offers a simple and effective method to quality control of the ginseng.
(5) Based on the unique capacity of magnetite beads to absorb microwave radiation, a new magnetite nano-beads based microwave-assisted (MBMAE) technique was developed to improve the extraction of bioactive compounds from plant tissues, Scutellaria baicalensis Georgi and its herbal preparations were taken as application examples. In the presence of magnetite beads, 40 s microwave irradiation, was sufficient for carrying out the whole extraction process, Furthermore, it yields a higher extraction efficiency compared with the conventional microwave extraction technique and a lower consumption of organic solvent. The extracts were analyzed by high performance liquid chromatography–electrospray ionization mass spectrometry. The recovery of this method was in the range of 97.6–101.4% with relative standard deviation lower than 2.5 %. The limits of detection were 0.05, 1.0 and 2.0 ng/mL for wogonin, baicalein and baicalin, respectively. The present method has been successfully applied to the extraction determinination of wogonin, baicalein and baicalin in real samples. The results demonstrated the powerful application foreground of the proposed method in analysis of bioactive compounds contained in other Chinese herbal medicine.
(6) In order to protect the animal, decrease or replace the animal experiments, the in-vitro assessment of the toxicity of the drug using the cell mode is urgently. Many clinical researches showed that CPT-11 is useful in the treatment of many types of cancer, such as colorectal, ovarian and small cell lung cancers, while there are few reports about the treatment of breast tumors. Human breast cancer cell line MCF-7 was selected as a model to test the potent anticancer activity of CPT-11 in vitro. A a simple, rapid and sensitive method of liquid chromatography-electrospray mass spectrometry has been developed to assay the concentrations of anticancer drug irinotecan in human breast cancer cells. A single step protein precipitation with the -80℃methanol was used for sample preparation. High specificity and little matrix effects was obtained by this method. After exposure to irinotecan at different time interval, the intracellular drug concentration was successfully determined by the proposed method. The pharmacokinetics of irinotecan in human breast cancer cells was investigated.
(7) The sample pretreatment is the key step in the biological sample analysis by HPLC. The sample pretreatment contains the protein precipitation and the analyte extraction, thus the operation is relatively laborious and time-consuming. Meantime, the recovery is low. A simple and sensitive micellar liquid chromatography (MLC) method is proposed for the determination of Cryptotanshinone (CT) and tanshinone IIA (TS) in biological samples. No extraction step is required. A C18 column and a micellar mobile phase of 0.15 M SDS and 8% n-butanol were used. CT and TS are the major active compounds contained in traditional Chinese medicine Radix salvia miltiorrhiza (Danshen), with powerful pharmacological activities. Satisfactory recoveries in the biological matrices were achieved for CT and TS. Compared with the conventional reversed-phase chromatography method, the proposed MLC method is more sensitive, time-saving and less organic solvent is required. The proposed method could be used for the pharmacokinetic studies of the CT and TS.
引文
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