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Systematic screening and structural characterization of dipeptides using offline 2D LC-LTQ-Orbitrap MS:A case study of Cordyceps sinensis

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Journal of Pharmaceutical Analysis 2022年第2期12卷 263-269页

作者： Xiaodie Li changliang yao Yun Li Zhengming Qian c Wenlong Wei Jianqing Zhang Jiayuan Li Qirui Bi Wenjia Li Yajun Cui De-an Guo Shanghai Research Center for Modernization of Traditional Chinese Medicine National Engineering Laboratory for Traditional Chinese Medicine Standardization TechnologyShanghai Institute of Materia MedicaChinese Academy of SciencesShanghai201203China Shanghai University of Traditional Chinese Medicine Shanghai201203China Key Laboratory of State Administration of Traditional Chinese Medicine Sunshine Lake Pharma Co.LtdDongguanGuangdong523850China

Cordyceps sinensis(C.sinensis)is a widely used and highly valuable traditional Chinese medicine.Several dipeptides have been detected in C.sinensis,but current scientific knowledge of its chemical makeup remains limited.In this study,an improved approach that integrates offline two-dimensional liquid chromatography(2D LC)separation,precursor ion list,library screening,and diagnostic ion filtering was established to systematically screen and characterize dipeptides in C.sinensis.Offline 2D LC integrating hydrophilic interaction LC and reverse phase separations was established to eliminate interference and identify the target dipeptides.A library containing the potential 400 dipeptides was created,and a precursor ion list with all theoretical precursor ions was adopted to trigger the MS/MS scan with high sensitivity.To identify dipeptides,the type and connection sequence of amino acids were determined according to the product ions.Ile and Leu residues were differentiated for the first time according to the characteristic ion at m/z 69.07.Ultimately,170 dipeptides were identified or tentatively characterized from C.sinensis,and most are reported for the first time in this species herein.In addition,the identified dipeptides were also applied for discrimination among the three Cordyceps species,and 11 markers were identified.The obtained results provide a deeper understanding of the chemical basis of C.sinensis.

关键词： Dipeptides Cordyceps sinensis Two-dimensional liquid chromatography Identification Isoleucine

Insight into chemical basis of traditional Chinese medicine based on the state-of-the-art techniques of liquid chromatography-mass spectrometry

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Acta Pharmaceutica Sinica B 2021年第6期11卷 1469-1492页

作者： Yang Yu changliang yao De-an Guo Shanghai Research Center for Modernization of Traditional Chinese Medicine National Engineering Laboratory for TCM Standardization TechnologyShanghai Institute of Materia MedicaChinese Academy of SciencesShanghai 201203China University of Chinese Academy of Sciences Beijing 100049China

Traditional Chinese medicine(TCM) has been an indispensable source of drugs for curing various human diseases.However,the inherent chemical diversity and complexity of TCM restricted the safety and efficacy of its usage.Over the past few decades,the combination of liquid chromatography with mass spectrometry has contributed greatly to the TCM qualitative analysis.And novel approaches have been continuously introduced to improve the analytical performance,including both the data acquisition methods to generate a large and informative dataset,and the data post-processing tools to extract the structure-related MS information.Furthermore,the fast-developing computer techniques and big data analytics have markedly enriched the data processing tools,bringing benefits of high efficiency and accuracy.To provide an up-to-date review of the latest techniques on the TCM qualitative analysis,multiple data-independent acquisition methods and data-dependent acquisition methods(precursor ion list,dynamic exclusion,mass tag,precursor ion scan,neutral loss scan,and multiple reaction monitoring)and post-processing techniques(mass defect filtering,diagnostic ion filtering,neutral loss filtering,mass spectral trees similarity filter,molecular networking,statistical analysis,database matching,etc.) were summarized and categorized.Applications of each technique and integrated analytical strategies were highlighted,discussion and future perspectives were proposed as well.

关键词： Liquid chromatography-mass spectrometry Qualitative analysis Traditional Chinese medicine Data acquisition Data post-processing

Characterization of natural peptides in Pheretima by integrating proteogenomics and label-free peptidomics

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Journal of Pharmaceutical Analysis 2023年第9期13卷 1070-1079页

作者： Xiaoxiao Luo Qirui Bi Dongdong Huang Yun Li changliang yao Jianqing Zhang Wenlong Wei Jiayuan Li Zhenwei Li Jingxian Zhang Shen Ji Yurong Wang De-an Guo School of Basic Medicine and Clinical Pharmacy China Pharmaceutical UniversityNanjing211198China Shanghai Research Center for Modernization of Traditional Chinese Medicine National Engineering Research Center of TCM Standardization TechnologyShanghai Institute of Materia MedicaChinese Academy of SciencesShanghai201203China University of Chinese Academy of Sciences Beijing100049China NMPA Key Laboratory for Quality Control of Traditional Chinese Medicine Shanghai Institute of Materia MedicaChinese Academy of SciencesShanghai201203China

Pheretima,also called“earthworms”,is a well-known animal-derived traditional Chinese medicine that is extensively used in over 50 Chinese patent medicines(CPMs)in Chinese Pharmacopoeia(2020 edition).However,its zoological origin is unclear,both in the herbal market and CPMs.In this study,a strategy for integrating in-house annotated protein databases constructed from close evolutionary relationship-sourced RNA sequencing data from public archival resources and various sequencing algorithms(restricted search,open search,and de novo)was developed to characterize the phenotype of natural peptides of three major commercial species of Pheretima,including Pheretima aspergillum(PA),Pheretima vulgaris(PV),and Metaphire magna(MM).We identified 10,477 natural peptides in the PA,7,451 in PV,and 5,896 in MM samples.Five specific signature peptides were screened and then validated using synthetic peptides;these demonstrated robust specificity for the authentication of PA,PV,and MM.Finally,all marker peptides were successfully applied to identify the zoological origins of Brain Heart capsules and Xiaohuoluo pills,revealing the inconsistent Pheretima species used in these CPMs.In conclusion,our integrated strategy could be used for the in-depth characterization of natural peptides of other animal-derived traditional Chinese medicines,especially non-model species with poorly annotated protein databases.

关键词： Pheretima Natural peptides Label-free peptidomics Proteogenomics Animal derived medicine

Chinese herbal medicines with beneficial effects

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Frigid Zone Medicine 2021年第2期1卷 79-83页

作者： De-an Guo Wenlong Wei changliang yao Jianqing Zhang Qirui Bi Shanghai Research Centre for Modernization of Traditional Chinese Medicine National Engineering Laboratory for TCM Standardization TechnologyShanghai Institute of Materia MedicaChinese Academy of Sciences501 Haike RoadShanghai 201203China

Among the vast resources of traditional Chinese medicine(TCM)herbal species,only a handful of Chinese herbs are growing in frigid regions or extreme environment but they have a unique property.The most recognizable TCM herb falling in this category is Panax ginseng,which is widely considered the representative tonic herb with oceans of beneficial effects on human health.In this article,we will introduce several typical Chinese herbal medicines with beneficial effects aiming to arouse broader attention from the scientific community to expand the exploration and exploitation on this for their potential applications to meet the increasingly demanding medical needs.

关键词： traditional Chinese medicine beneficial effects panax ginseng rhodiola rosea schisandra chinensis

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瑞德西韦制备工艺中手性杂质的合成

中国医药工业杂志 2022年第8期53卷 1141-1147页

作者：方治坤朱阳姚长亮上海医药集团股份有限公司中央研究院上海201203

为了增强对瑞德西韦的质量控制,设计合成了其工艺路线中易产生的重要手性杂质,包括(S)-2-[[(S)-[[(2R,3S,4R,5S)-5-(4-氨基吡咯并[2,1-f][1,2,4]三嗪-7-基)-5-氰基-3,4-二羟基四氢呋喃-2-基]甲氧基](苯氧基)磷酰基]氨基]丙酸-2-乙基丁基... 详细信息

为了增强对瑞德西韦的质量控制,设计合成了其工艺路线中易产生的重要手性杂质,包括(S)-2-[[(S)-[[(2R,3S,4R,5S)-5-(4-氨基吡咯并[2,1-f][1,2,4]三嗪-7-基)-5-氰基-3,4-二羟基四氢呋喃-2-基]甲氧基](苯氧基)磷酰基]氨基]丙酸-2-乙基丁基酯,以及其(S)-2-[(R)-(2R,3S,4R,5R)]-型和(S)-2-[(R)-(2R,3S,4R,5S)]-型光学异构体,这些化合物的结构通过MS和NMR确证。本工艺条件温和、收率高、无需手性分离,适合实验室规模制备。

关键词：瑞德西韦新型冠状病毒肺炎手性杂质

SIMULTANEOUS QUANTITATION OF FIVE PANAX NOTOGINSENG SAPONINS IN EIGHT CHINESE PATENT MEDICINES BY MULTI HEART-CUTTING TWODIMENSIONAL LIQUID CHROMATOGRAPHY

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World Journal of Traditional Chinese Medicine 2015年第4期1卷 69-69页

作者： changliang yao Wenzhi Yang Wanying Wu Jinjun Hou Jingxian Zhang Yanhai Zhang Dean Guo Shanghai Research Center for Modernization of Traditional Chinese Medicine National Engineering Laboratory for TCM Standardization Technology Shanghai Institute of Materia Medica Chinese Academy of Sciences Thermo Fisher Scientific

Current China Pharmacopoeia(ChP)standards employ diversified and case-dependent assay methods to evaluate the quality of different Chinese patent medicines(CPM)that contain Panax notoginseng as the monarch drug.This study is aimed to develop a two-dimensional liquid chromatography(2D LC)based assay approach to unify and simplify the quality assessment of Notoginseng containing CPMs.Multi heart-cutting 2D LC(MHC-2D LC)was used to separate and quantify five major

关键词： MHC SIMULTANEOUS QUANTITATION OF FIVE PANAX NOTOGINSENG SAPONINS IN EIGHT CHINESE PATENT MEDICINES BY MULTI HEART-CUTTING TWODIMENSIONAL LIQUID CHROMATOGRAPHY

美登素衍生物DM1聚合物杂质聚合物1的合成研究

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上海医药 2022年第23期43卷 75-78页

作者：朱阳姚长亮夏广兵上海医药集团股份有限公司中央研究院上海201203

目的:在制备DM1的过程中研究DM1的聚合物杂质聚合物1的简便合成方法,以期在DM1制备过程中有效控制该杂质的产生。方法:DM1在1,3-二甲基-2-咪唑啉酮中很容易脱氢聚合,生成聚合物1。结果:所得聚合物1的化学结构已经得到质谱、核磁共振氢... 详细信息

目的:在制备DM1的过程中研究DM1的聚合物杂质聚合物1的简便合成方法,以期在DM1制备过程中有效控制该杂质的产生。方法:DM1在1,3-二甲基-2-咪唑啉酮中很容易脱氢聚合,生成聚合物1。结果:所得聚合物1的化学结构已经得到质谱、核磁共振氢谱、核磁共振碳谱等检测的确证。结论:本合成方法操作简便,不需繁琐的后处理或柱层析纯化即能获得高纯度的聚合物1,可直接用作DM1有关物质质量控制的对照品。

关键词： DM1 聚合物杂质合成

基于λ一级红波长补偿器与偏振光显微镜联合应用对木通类药材及其混淆品的生药学显微鉴别研究

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世界科学技术-中医药现代化 2022年第9期24卷 3346-3363页

作者：蒙倩李小蝶韩文凯金如艳姚长良崔亚君上海中医药大学中药学院上海201203 中国科学院上海药物研究所上海201203

目的对显微鉴别3种视场(正常光明场、偏振光暗场、λ一级红波长补偿器与偏振光显微镜联合应用显微鉴别法)进行方法学研究,并基于该研究结果对市场上8种常见木通类药材及其混淆品(木通、三叶木通、白木通;小木通、绣球藤;粗齿铁线莲、钝... 详细信息

目的对显微鉴别3种视场(正常光明场、偏振光暗场、λ一级红波长补偿器与偏振光显微镜联合应用显微鉴别法)进行方法学研究,并基于该研究结果对市场上8种常见木通类药材及其混淆品(木通、三叶木通、白木通;小木通、绣球藤;粗齿铁线莲、钝萼铁线莲;关木通)进行生药学再研究,为显微鉴别技术提供新方法,也为市场上常见木通类药材及其混淆品的鉴定提供依据。方法采用传统性状鉴别法、微性状鉴别法、正常光明场、正交偏振光暗场及λ一级红波长补偿器与偏振光显微镜联合应用显微鉴别法对比研究,结合大型图像拼接及实时景深扩展技术获取全息彩色影像数据。结果建立了λ一级红波长补偿器与偏振光显微镜联合应用于木通类药材及其混淆品的微鉴别研究新方法;通过方法学研究获取了8种木通类药材及其混淆品的性状及精细结构微性状影像数据、药材横断面及粉末正常光明场、正交偏振光暗场及λ一级红波长补偿器与偏振光显微镜联合应用视场下全息彩色影像数据,结果显示木通类药材及其混淆品横断面特征具有差异较大。结论木通类药材及其混淆品髓部微性状及断面维管束分布规律具有较大差异;λ一级红波长补偿器与偏振光显微镜联合应用适合木通类药材及其混淆品的显微鉴别,方法学研究结果表明正常光明场下获得的全息彩色影像数据可真实展示显微组织横切面完整信息,正交偏振光暗场下所获得的全息彩色影像数据可以突显双折性物质的植物组织构造及细胞内含物显微特征及分布规律,适于木化组织构造和结晶类细胞内含物存在部位的整体观察,缺点是非双折射性组织构造及内含物融入黑色背景,导致该部分形态学信息缺失,λ一级红波长补偿器与偏振光显微镜联合应用显微鉴别法可以使具有双折射性特征的组织构造被突显的同时,无偏振光现象的非双折射性组织构造能够显示,综合体现了正常光、正交偏振光显微影像下的共有优势,一级红波长条件下,细胞间隙等透明部分呈粉色背景,但由于色彩过多,易影响完整组织图像缩略图观察效果,适合局部特征观察;基于λ一级红波长补偿器与偏振光显微镜联合应用显微鉴别法为生药显微鉴别的方法学研究提供了新借鉴,也为木通类药材及其混淆品的鉴别提供科学依据。

关键词：木通川木通关木通显微鉴别偏振光显微镜补偿器

Temporal variations of δ^(18)O of atmospheric water vapor at Delingha

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Science China Earth Sciences 2008年第7期51卷 966-975页

作者： YIN changliang1, yao TanDong2, TIAN LiDe2, LIU DongNian3, YU WuSheng2 & QU DongMei2 1 State Key Laboratory of Cryoshperic Science, Cold and Arid Regions Environmental and Engineering Research Institute, Chinese Academy of Sciences, Lanzhou 730000, China 2 Laboratory of Environment and Processes, Institute of Tibetan Plateau Research, Chinese Academy of Sciences, Beijing 100085, China 3 Meteorological Observatory of Haixi Prefecture of Qinghai Province, Delingha 817000, China State Key Laboratory of Cryoshperic Science Cold and Arid Regions Environmental and Engineering Research Institute Chinese Academy of Sciences Lanzhou China Laboratory of Environment and Processes Institute of Tibetan Plateau Research Chinese Academy of Sciences Beijing China Meteorological Observatory of Haixi Prefecture of Qinghai Province Delingha China

Oxygen stable isotope of atmospheric water vapor is widely used to study the modern process of cli- mate. Atmospheric water vapor samples were collected at Dlingha, northeast of Tibetan Plateau during the period from July 2005 to February 2006. The variation of δ18O and the relationships between δ18O and both the temperature and specific humidity are analyzed in this paper. Results show that the sea- sonal variation of δ18O of atmospheric water vapor at Delingha is remarkable with higher δ18O in summer and lower δ18O in winter. The temporal variation of vapor δ18O shows obvious fluctuations, with magnitude of over 37‰. The daily variation of the δ18O is highly correlated with air temperature. The relationship between δ18O and atmospheric water vapor content is complex. Study shows that δ18O of atmospheric water vapor is positively correlated with specific humidity in winter in seasonal scale and inversely correlated with specific humidity in summer rainy period. The δ18O values of at- mospheric water vapor are lower than those of precipitation at Delingha, and the average difference is 10.7‰. Variations of δ18O of atmospheric water vapor is also found to be affected by precipitation events, The model results show that the precipitation effect could have caused the vapor δ18O in the raining season to lower by 7% in average in July and August.

关键词： Delingha δ18O atmospheric water vapor