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Comprehensive chemical profiling and quantitative analysis of ethnic Yi medicine Miao-Fu-Zhi-Tong granules using UHPLC-MS/MS

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Chinese Journal of Natural Medicines 2023年第3期21卷 214-225页

作者： LEI Xiaoying ZHANG Chen ZHAO Suqing CHENG Shuohan ZHOU Wenbin XU Jiapeng ZHAN Ping zeper abliz School of Pharmacy Minzu University of ChinaBeijing 100081China Key Laboratory of Mass Spectrometry Imaging and Metabolomics Minzu University of ChinaNational Ethnic Affairs CommissionBeijing 100081China Key Laboratory of Ethnomedicine of Ministry of Education Minzu University of ChinaBeijing 100081China Traditional Chinese Medicine Hospital of Chuxiong Yi Autonomous Prefecture(Traditional Yi Medicine Hospital of Yunnan Province) Chuxiong 675000China

Developing analytical methods for the chemical components of natural medicines remains a challenge due to its diversity and complexity.Miao-Fu-Zhi-Tong(MFZT)granules,an ethnic Yi herbal prescription,comprises 10 herbs and has been clinically applied for gouty arthritis(GA)therapy.Herein,a series of chemical profiling strategies including in-house library matching,molecular networking and MS/MS fragmentation behavior validation based on ultra-high performance liquid chromatography-tandem mass spectrometry(UHPLC-MS/MS)were developed for qualitative analysis of MFZT granules.A total of 207 compounds were identified or characterized in which several rare guanidines were discovered and profiled into alkyl substituted or cyclic subtypes.Moreover,network pharmacology analysis indicated that MFZT’s anti-gout mechanism was mostly associated with the nuclear factor kappa-B(NF-κB)signaling,nucleotide oligomerization domain(NOD)-like signaling and rheumatoid arthritis pathways,along with the synergistic effect of 84 potential active compounds.In addition,a quantitative analytical method was developed to simultaneously determine the 29 potential effective components.Among them,berberine,pellodendrine,3-feruloylquinic acid,neoastilbin,isoacteoside and chlorogenic acid derivatives at higher concentrations were considered as the chemical markers for quality control.These findings provide a holistic chemical basis for MFZT granules and will support the development of effective analytical methods for the herbal formulas of natural medicines.

关键词： Natural medicines Miao-Fu-Zhi-Tong granules Chemical profiling Quantitative analysis Network pharmacology

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Integrated mass spectrometry imaging reveals spatial-metabolic alteration in diabetic cardiomyopathy and the intervention effects of ferulic acid

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Journal of Pharmaceutical Analysis 2023年第12期13卷 1496-1509页

作者： Yanhua Liu Xin Zhang Shu Yang Zhi Zhou Lu Tian Wanfang Li Jinfeng Wei zeper abliz Zhonghua Wang Key Laboratory of Mass Spectrometry Imaging and Metabolomics(Minzu University of China) National Ethnic Affairs CommissionBeijing100081China Center for Imaging and Systems Biology College of Life and Environmental SciencesMinzu University of ChinaBeijing100081China New Drug Safety Evaluation Center Institute of Materia MedicaPeking Union Medical CollegeBeijing100050China Key Laboratory of Ethnomedicine of Ministry of Education School of PharmacyMinzu University of ChinaBeijing100081China

Diabetic cardiomyopathy(DCM)is a metabolic disease and a leading cause of heart failure among people with diabetes.Mass spectrometry imaging(MSI)is a versatile technique capable of combining the molecular specificity of mass spectrometry(MS)with the spatial information of imaging.In this study,we used MSI to visualize metabolites in the rat heart with high spatial resolution and sensitivity.We optimized the air flow-assisted desorption electrospray ionization(AFADESI)-MSI platform to detect a wide range of metabolites,and then used matrix-assisted laser desorption ionization(MALDI)-MSI for increasing metabolic coverage and improving localization resolution.AFADESI-MSI detected 214 and 149 metabolites in positive and negative analyses of rat heart sections,respectively,while MALDI-MSI detected 61 metabolites in negative analysis.Our study revealed the heterogenous metabolic profile of the heart in a DCM model,with over 105 region-specific changes in the levels of a wide range of metabolite classes,including carbohydrates,amino acids,nucleotides,and their derivatives,fatty acids,glycerol phospholipids,carnitines,and metal ions.The repeated oral administration of ferulic acid during 20 weeks significantly improved most of the metabolic disorders in the DCM model.Our findings provide novel insights into the molecular mechanisms underlying DCM and the potential of ferulic acid as a therapeutic agent for treating this condition.

关键词： Mass spectrometry imaging Diabetic cardiomyopathy Metabolic reprogramming Ferulic acid

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Spatiotemporal pharmacometabolomics based on ambient mass spectrometry imaging to evaluate the metabolism and hepatotoxicity of amiodarone in HepG2 spheroids

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Journal of Pharmaceutical Analysis 2023年第5期13卷 483-493页

作者： Limei Li Qingce Zang Xinzhu Li Ying Zhu Shanjing Wen Jiuming He Ruiping Zhang zeper abliz State Key Laboratory of Bioactive Substance and Function of Natural Medicines Institute of Materia MedicaChinese Academy of Medical Sciences and Peking Union Medical CollegeBeijing100050China Key Laboratory of Mass Spectrometry Imaging and Metabolomics(Minzu University of China) National Ethnic Affairs CommissionBeijing100081China Center for Imaging and Systems Biology College of Life and Environmental SciencesMinzu University of ChinaBeijing100081China

Three-dimensional(3D)cell spheroid models combined with mass spectrometry imaging(MSI)enables innovative investigation of in vivo-like biological processes under different physiological and pathological conditions.Herein,airflow-assisted desorption electrospray ionization-MSI(AFADESI-MSI)was coupled with 3D HepG2 spheroids to assess the metabolism and hepatotoxicity of amiodarone(AMI).High-coverage imaging of>1100 endogenous metabolites in hepatocyte spheroids was achieved using AFADESI-MSI.Following AMI treatment at different times,15 metabolites of AMI involved in Ndesethylation,hydroxylation,deiodination,and desaturation metabolic reactions were identified,and according to their spatiotemporal dynamics features,the metabolic pathways of AMI were proposed.Subsequently,the temporal and spatial changes in metabolic disturbance within spheroids caused by drug exposure were obtained via metabolomic analysis.The main dysregulated metabolic pathways included arachidonic acid and glycerophospholipid metabolism,providing considerable evidence for the mechanism of AMI hepatotoxicity.In addition,a biomarker group of eight fatty acids was selected that provided improved indication of cell viability and could characterize the hepatotoxicity of AMI.The combination of AFADESI-MSI and HepG2 spheroids can simultaneously obtain spatiotemporal information for drugs,drug metabolites,and endogenous metabolites after AMI treatment,providing an effective tool for in vitro drug hepatotoxicity evaluation.

关键词： Mass spectrometry imaging HepG2 spheroids Hepatotoxicity Drug metabolism Amiodarone

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Spatiotemporally resolved metabolomics and isotope tracing reveal CNS drug targets

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Acta Pharmaceutica Sinica B 2023年第4期13卷 1699-1710页

作者： Bo Jin Xuechao Pang Qingce Zang Man Ga Jing Xu Zhigang Luo Ruiping Zhang Jiangong Shi Jiuming He zeper abliz State Key Laboratory of Bioactive Substance and Function of Natural Medicines Institute of Materia MedicaChinese Academy of Medical Sciences and Peking Union Medical CollegeBeijing 100050China NMPA Key Laboratory for Safety Research and Evaluation of Innovative Drug Beijing 100050China Key Laboratory of Mass Spectrometry Imaging and Metabolomics(Minzu University of China) National Ethnic Affairs CommissionBeijing 100081China Key Laboratory of Ethnomedicine of Ministry of Education School of PharmacyMinzu University of ChinaBeijing 100081China

Deconvolution of potential drug targets of the central nervous system(CNS)is particularly challenging because of the complicated structure and function of the brain.Here,a spatiotemporally resolved metabolomics and isotope tracing strategy was proposed and demonstrated to be powerful for deconvoluting and localizing potential targets of CNS drugs by using ambient mass spectrometry imaging.This strategy can map various substances including exogenous drugs,isotopically labeled metabolites,and various types of endogenous metabolites in the brain tissue sections to illustrate their microregional distribution pattern in the brain and locate drug action-related metabolic nodes and pathways.The strategy revealed that the sedative-hypnotic drug candidate YZG-331 was prominently distributed in the pineal gland and entered the thalamus and hypothalamus in relatively small amounts,and can increase glutamate decarboxylase activity to elevateγ-aminobutyric acid(GABA)levels in the hypothalamus,agonize organic cation transporter 3 to release extracellular histamine into peripheral circulation.These findings emphasize the promising capability of spatiotemporally resolved metabolomics and isotope tracing to help elucidate the multiple targets and the mechanisms of action of CNS drugs.

关键词： Ambient mass spectrometry imaging Spatiotemporally resolved metabolomics Isotope tracing Drug targets Central nervous system Drug candidate

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Study on fragmentation behavior of taxoids by tandem mass spectrometry

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Chinese Science Bulletin 2000年第8期45卷 688-698页

作者： zeper abliz Mitsuo Takayama Institute of Materia Medica Chinese Academy of Medical Sciences & Peking Union Medical CollegeBeiging 100050.ChinaFaculty of Pharmaceutical SciencesToho University2-2-1 MiyamaFunabashiChiba 274Japan

We have studied the fragmentation behavior of positive and negative ions of taxoi and 6/8/6 type taxoids, the influence of different substituents on fragmentation, and the correlativity between fragmentation patterns and structure by MS/MS technique with different ionization methods such as FAB-MS, ESI-MS, ete. We have also investigated in detail the fragmentation of various molecular-related ions, such as [M+H]+, [M+Na]+ and [M-H] ions, and the formation pathways of characteristic fragment ions. It has been found that there exists some competing reaction between the loss of C-13 side chain and decomposition by loss of acetic acid. In addition, by comparing CID spectra obtained with low- and high-energy collision, it is seen that CID-MS/MS with low-energy collision is more suitable for the study of the structural analysis of small molecules and drug metabolites. The experimental results demonstrate that MS/MS spectra can reflect more effectively the slight difference of structure between the related

关键词： taxol taxoids tandem mass spectrometry fragmentation behavior.

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Existence of aromatic sp^2 C-H…O = C intramolecular interaction similar to hydrogen bond

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Science China Chemistry 1996年第3期39卷 285-291页

作者： zeper abliz Hiroshi Moriyama Junji Aoki Toyotoshi Ueda Department of Chemistry Xin Jiang University Urumchi 830046ChinaDepartment of Chemistry Toho University Funabashi Chiba 274 JapanDepartment of Chemistry Toho University Funabashi Chiba 274 JapanDepartment of ChemistryMeisei UniversityHino Tokyo 191 Japan

A ’H NMR signal shifted drastically to down field (δ - 10.0) at the bay area and in dose proximity to C = O group for H-1 was observed through complete assignments of 1H NMR spectra for pyridino- and benzobenzanthrones. It is concluded that this phenomenon is due not only to the anisotropy effect of C=O plus aromatic ring current effect, but also to the electrostatic attraction of C-H (δ+)…O(δ-)=C interaction. The evidence for the sp2C-H…O = C intramolecular interaction similar to hydrogen bond has also been given by EI-MS and MS/MS (CID) spectroscopy and IR spectroscopy, as well as MNDO-PM3 calculations. This new kind of interaction might be called ’quasi-hydrogen bond’.

关键词： polycyclic aromatic ketone pyridinobenzanthrone intramolecular interaction hydrogen bond quasl-hydrogen bond.

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In situ metabolomics in nephrotoxicity of aristolochic acids based on air flow-assisted desorption electrospray ionization mass spectrometry imaging

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Acta Pharmaceutica Sinica B 2020年第6期10卷 1083-1093页

作者： Zhonghua Wang Bingshu He Yaqi Liu Meiling Huo Wenqing Fu Chunyan Yang Jinfeng Wei zeper abliz Center for Imaging and Systems Biology College of Life and Environmental SciencesMinzu University of ChinaBeijing 100081China New Drug Safety Evaluation Center Institute of Materia MedicaPeking Union Medical CollegeBeijing 100050China Key Laboratory of Ethnomedicine of Ministry of Education Minzu University of ChinaBeijing 100081China School of Pharmacy Minzu University of ChinaBeijing 100081China

Understanding of the nephrotoxicity induced by drug candidates is vital to drug discovery and development.Herein,an in situ metabolomics method based on air flow-assisted desorption electrospray ionization mass spectrometry imaging(AFADESI-MSI)was established for direct analysis of metabolites in renal tissue sections.This method was subsequently applied to investigate spatially resolved metabolic profile changes in rat kidney after the administration of aristolochic acid I,a known nephrotoxic drug,aimed to discover metabolites associated with nephrotoxicity.As a result,38 metabolites related to the arginine-creatinine metabolic pathway,the urea cycle,the serine synthesis pathway,metabolism of lipids,choline,histamine,lysine,and adenosine triphosphate were significantly changed in the group treated with aristolochic acid I.These metabolites exhibited a unique distribution in rat kidney and a good spatial match with histopathological renal lesions.This study provides new insights into the mechanisms underlying aristolochic acids nephrotoxicity and demonstrates that AFADESI-MSI-based in situ metabolomics is a promising technique for investigation of the molecular mechanism of drug toxicity.

关键词： Aristolochic acid Nephrotoxicity Mass spectrometry imaging In situ metabolomics AFADESI

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Rapid and sensitive liquid chromatography–tandem mass spectrometric method for the quantitative determination of potentially harmful substance 5,5′-oxydimethylenebis (2-furfural) in traditional Chinese medicine injections

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Acta Pharmaceutica Sinica B 2018年第2期8卷 235-241页

作者： Qingce Zang Yang Gao Luojiao Huang Jiuming He Sheng Lin Hongtao Jin Ruiping Zhang zeper abliz State Key Laboratory of Bioactive Substance and Function of Natural Medicines Institute of Materia Medica Chinese Academy of Medical Science and Peking Union Medical College New Drug Safety Evaluation Center Institute of Materia Medica Chinese Academy of Medical Sciences and Peking Union Medical College Centre for Bioimaging & Systems Biology Minzu University of China

With the rapid development and wide application of traditional Chinese medicine injection(TCMI), a number of adverse events of some TCMIs have incessantly been reported and have drawn broad attention in recent years. Establishing effective and practical analytical methods for safety evaluation and quality control of TCMI can help to improve the safety of TCMIs in clinical applications. In this study, a sensitive and rapid high-performance liquid chromatography–tandem mass spectrometry(HPLC–MS/MS)method has been developed and validated for the quantitative determination of potentially harmful substance5,5′-oxydimethylenebis(2-furfural, OMBF) in TCMI samples. Chromatographic separation was performed on a C18 reversed-phase column(150 mm × 2.1 mm, 5 μm) by gradient elution, using methanol–water containing 0.1% formic acid as mobile phase at the flow rate of 0.3 m L/min. MS/MS detection was performed on a triple quadrupole mass spectrometer with positive electrospray ionization in the multiple reaction-monitoring mode. The method was sensitive with a limit of quantification of 0.3 ng/m L and linear over the range of 0.3–30 ng/m L(r = 0.9998). Intra-and inter-day precision for analyte was o9.52% RSD withrecoveries in the range 88.0–109.67% at three concentration levels. The validated method was successfully applied to quantitatively determine the compound OMBF in TCMIs and glucose injections. Our study indicates that this method is simple, sensitive, practicable and reliable, and could be applied for safety evaluation and quality control of TCMIs and glucose injections.

关键词： 5,5′-Oxydimethylenebis (2-furfural) LC–MS/MS Quantitative analytical method Traditional Chinese medicine injection Quality control

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Design and performance of air flow-assisted ionization imaging mass spectrometry system

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Chinese Chemical Letters 2014年第5期25卷 687-692页

作者： Fei Tang Yi Chen Jiu-Ming He Zhi-Gang Luo zeper abliz Xiao-Hao Wang State Key Laboratory of Precision Measurement Technology and Instruments Department of Precision InstrumentTsinghua University State Key Laboratory of Bioactive Substance and Function of Natural Medicines Institute of Materia MedicaChinese Academy of Medical Sciences and Peking Union Medical College

The imaging mass spectrometry（IMS） technology has experienced a rapid development in recent years.A new IMS technology which is based on air flow assisted ionization（AFAI） was reported.It allows for the convenient pretreatment of the samples and can image a large area of sample in a single measurement with high sensitivity.The AFAI in DESI mode was used as the ion source in this paper.The new IMS method is named AFADESI-IMS.The adoption of assisted air flow makes the sample pretreatment easy and convenient.An optimization of the distance between the ion transport tube and MS orifice increases the sensitivity of the system.For data processing,a program based on MATLAB with the function of numerical analysis was developed.A theoretical imaging resolution of a few hundred microns can be achieved.The composite AFAI-IMS images of different target analytes were imaged with high sensitivity.A typical AFAI-IMS image of the whole-body section of a rat was obtained in a single analytical measurement.The ability to image a large area for relevant samples in a single measurement with high sensitivity and repeatability is a significant advantage.The method has enormous potentials in the MS imaging of large and complicated samples.

关键词： Imaging mass spectrometry Air flow assisted ionization imaging mass spectrometry Whole-body imaging Large and complicated sample imaging

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Self-assembly of Pyrene-modified Rhomboidal Metalloden- drimers via Directional Metal-ligand Bonding Approach

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Chinese Journal of Chemistry 2013年第5期31卷 663-672页

作者： Menglan He Qing Han Jiuming He Quanjie Li zeper abliz Hongwei Tan Lin Xu Haibo Yang Shanghai Key Laboratory of Green Chemistry and Chemical Processes Department of Chemistry East China Normal University Shanghai 200062 China Institute of Materia Medica Chinese Academy of Medical Sciences and Peking Union Medical College Beijing 100050 China Department of Chemistry Beijing Normal University Beijing 100875 China

设计并且经由方向性的 metal-ligand 的修改分核的长斜方形的 metallodendrimers R1R6 自己组装结合的途径被描述。由采用包含分核 120 敺搠獩牴扩瑵潩 ? 景 ? 偄华 ? 敷敲搠瑥牥業敮 ? 祢搠湹浡捩氠杩?

关键词：斜方晶系金属配体自组装改性树枝状聚合物半经验分子轨道法芘质谱数据

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