Co-reporter:Xiaoyan Lu, Wei Tong, Shufang Wang, Jinghui Li, Jie Zheng, Xiaohui Fan, Li Liu
Journal of Pharmaceutical and Biomedical Analysis 2017 Volume 134() pp:60-70
Publication Date(Web):5 February 2017
DOI:10.1016/j.jpba.2016.11.025
•Chemical profiles of Ophiopogonis Radix from two areas were compared by LC–MS.•19 constituents were identified as chemical markers to distinguish ZMD from CMD.•ZMD possesses better immunomodulatory activities than CMD in zebrafish.•Geographical area should be considered in preparing herb medicine.Zhemaidong (ZMD) and Chuanmaidong (CMD) are the two genuine cultivation areas of Ophiopogonis Radix which has been widely used as a traditional Chinese medicine in China for treating cardiovascular and pulmonary diseases. Differences between ZMD and CMD in chemical constituents and pharmacological effects have been reported, however, the details remain largely unknown. The aim of this study was to comprehensively characterize the chemical composition of Ophiopogonis Radix from the two producing areas and compare their immunomodulatory activities. An approach of HPLC–MS coupled with multivariate statistical analysis was established to reveal the characteristic constituents of ZMD and CMD. Furthermore, the effects of ZMD and CMD on the macrophage phagocytosis and gastrointestinal peristalsis were also determined in zebrafish models for assessing the immunomodulatory activities of these two strains. The results revealed that the chemical constituents of ZMD and CMD were much different from each other, and 19 constituents could be served as chemical markers to distinguish these two strains. Moreover, ZMD showed higher promoting rates in macrophage phagocytosis and gastrointestinal motility than those of CMD, suggesting ZMD might possess better immunomodulatory activities. Taken together, the results generated from this study indicated that the herbs from different producing areas should be evaluated and considered in preparing TCM prescriptions.
Co-reporter:
Journal of Separation Science 2017 Volume 40(Issue 6) pp:1254-1265
Publication Date(Web):2017/03/01
DOI:10.1002/jssc.201601054
In this study, we propose an integrated strategy for the efficient identification and quantification of herbal constituents using liquid chromatography with mass spectrometry. First, liquid chromatography with quadrupole time-of-flight mass spectrometry was employed for the chemical profiling of herbs, where a targeted following nontargeted approach was developed to detect trace constituents by using structural correlations and extracted ion chromatograms. Next, ion pairs and parameters of MS2 of quadrupole time-of-flight mass spectrometry were selected to design multiple reaction monitoring transitions for the identified compounds on liquid chromatography with triple quadrupole mass spectrometry. The relative concentration of each constituent was then calculated using a semiquantitative calibration curve. The proposed strategy was applied in a study of chemical interactions between Glycyrrhizae Radix and Coptidis Rhizoma. A total of 140 compounds were identified or tentatively characterized from the herbs, 132 of which were relatively quantified. The visualized quantitative results clearly showed codecoction produced significant constituent concentration variations especially for those with a low polarity. The case study also indicated that the present methodology could provide a reliable, accurate, and labor-saving solution for chemical studies of herbal medicines.
Co-reporter:Xiaoyan Lu, Xueping Lian, Jie zheng, Ni Ai, Cai Ji, Cui Hao and Xiaohui Fan
RSC Advances 2016 vol. 6(Issue 23) pp:19545-19554
Publication Date(Web):04 Feb 2016
DOI:10.1039/C5RA24301G
As a major adverse drug reaction associated with traditional Chinese medicine injections (TCMIs), an anaphylactoid reaction has attracted a significant amount of attention from regulatory agencies and research communities. To ensure safe and effective use of TCMIs in the clinic, it is of great importance to identify the causative chemical responsible for the anaphylactoid reaction observed. Ginsenoside Rd (Rd) is one of the main active components in several TCMIs which have been recently reported to cause an anaphylactoid reaction. In this study, the possibility of an Rd-induced anaphylactoid reaction was first evaluated using general toxicological assessments. As a result, the in vitro model showed that Rd treatment could directly induce β-hexosaminidase release in RBL-2H3 cells through mast cell degranulation. Further in vivo studies revealed that cutaneous vascular permeability and plasma histamine levels were significantly increased in Rd-treated mice, strengthening the fact that Rd could induce an anaphylactoid reaction. Moreover, a comprehensive metabolomic approach was established to investigate the effects of an Rd-induced anaphylactoid reaction in mice using liquid chromatography-electrospray ionization-time-of-flight-mass spectrometry. Our results evinced that alterations in the metabolites related to inflammation and allergy diseases were observed during the early stage of an anaphylactoid reaction, including glycerophospholipids, corticosteroid hormones, bile acids, sterol lipids, and fatty acids, suggesting that the disturbances in lipid metabolism may be involved in the Rd-induced anaphylactoid reaction, such as glycerophospholipid and steroid hormone metabolism. Thus, Rd may be an allergenic factor inducing an anaphylactoid reaction in Rd-contained TCMIs.
Co-reporter:Zhenhao Li, Shun Xiao, Ni Ai, Kedi Luo, Xiaohui Fan, Yiyu Cheng
Journal of Chromatography A 2015 Volume 1376() pp:126-142
Publication Date(Web):9 January 2015
DOI:10.1016/j.chroma.2014.12.024
•Based on MS2 of IT/MS, DeMRM was proposed for direct and rapid transitions design.•SHCA was employed instead of standards to construct the calibration curve.•The method achieved favorable performance for multi-component quantification.•Compatibility-induced alterations in chemicals were investigated methodically.In comparison with monotherapy in western medicine, traditional Chinese medicine (TCM) advocates combinational therapy for treating diseases and TCM formula is a representative for this approach. Despite of extensive clinical applications of TCM formulae, knowledge about their pharmacological activities, mechanisms of action and cellular targets remains limited. A main contributing factor to these unanswered questions is unavailability of chemical compositions and their contents in the formulae. Several challenges hinder global qualitative and quantitative analysis of the formulae, including large quantities of constituents, potential physicochemical changes during decoction and lack of authentic standards. Herein we introduced an integrated strategy based on liquid chromatography coupled with mass spectrometry (LC-MS) systems to address such challenges. First, liquid chromatography-ion trap and quadrupole time-of-flight mass spectrometry (LC-IT/MS and LC-QTOF/MS) were utilized to characterize chemical profiling of the formulae. Meanwhile, MS2 of IT/MS produced major parameters for derivative multiple reaction monitoring (DeMRM) on liquid chromatography-triple quadrupole mass spectrometry (LC-TQ/MS), which offered rapid and direct transition design in the quantitative assay. Instead of authentic standards, serial dilutions of single herbs were employed in this study to construct calibration curves necessary for calculating relative concentrations of components. Xiao-Banxia decoction and its four analogous formulae were then taken to exemplify the feasibility of currently proposed methodology. Among the 160 qualitatively identified components, a total of 138 components were semi-quantified for these decoctions. Based on these results, we demonstrated that co-decoction of different herbs could result in concentration variations of components and this effect was more prominent when certain herbs were combined. Our results indicated that the present strategy would significantly contribute to chemical studies on TCM and its utilities could be extended to other research fields, such as metabolomics and comparative chemistry.
Co-reporter:Shun Xiao, Runru Yu, Ni Ai, Xiaohui Fan
Journal of Pharmaceutical and Biomedical Analysis 2015 Volume 104() pp:67-74
Publication Date(Web):10 February 2015
DOI:10.1016/j.jpba.2014.11.022
•Developed a rapid approach for screening lipase inhibitors from four TCM formulae by combing LC–MS with ultrafiltration.•Sixteen natural-origin lipase inhibitors was discovered and identified by high resolution and multistage mass spectrometry.•Inhibitory activities of two compounds were confirmed in a functional assay of lipase.•Molecular docking simulations were performed to investigate potential mechanism of action for these compounds.Lipase inhibitors generate hypolipidemic effect that is helpful to control or treat some obesity diseases by inactivating catalytic activity of human pancreatic lipase, a key enzyme involved in triglyceride hydrolysis in vivo. Many traditional Chinese medicine (TCM) formulae have been effectively used to treat obesity and other fat related diseases for centuries and modern biological experiments demonstrate therapeutic effect of these formulae can be linked to their lipid-lowering capability in blood. These observations suggest that these hypolipidemic decoctions (HDs) could be a promising resource of natural-origin lipase inhibitors. This work described a rapid approach for screening lipase inhibitors from four widely used HDs, including Wu-Ling-San (WLS), Ze-Xie decoction (ZX), Xiao-Xian-Xiong decoction (XXX) and Xiao-Chai-Hu decoction (XCH), by ultrafiltration combing with high performance liquid chromatography–mass spectrometry (HPLC–MS). Our results showed sixteen natural-origin lipase inhibitors were discovered and identified by high resolution and multistage mass spectrometry. Inhibitory activities of two compounds were confirmed by a functional assay of lipase, which validated the reliability of our approach. Molecular docking simulation was then performed to investigate potential mechanism of action for these compounds. Together we present an efficient method for rapid screening lipase inhibitors from complex natural products, which can be easily accommodated to other important enzymatic system with therapeutic values.
Co-reporter:Linli Wang, Zheng Li, Qing Shao, Xiang Li, Ni Ai, Xiaoping Zhao and Xiaohui Fan
Molecular BioSystems 2014 vol. 10(Issue 7) pp:1905-1911
Publication Date(Web):30 Apr 2014
DOI:10.1039/C3MB70581A
Chinese medicine has been widely used in clinical practice, but its mode of action often remains obscure. This has seriously hindered further development and better clinical applications of Chinese medicine. Among the most critical questions to be addressed, the identification of active ingredients is an important one requiring more research. Existing methods are only concerned the potential pharmacological effects of the individual purified chemical ingredients without consideration of the contents of these ingredients, which is critical to the comprehensive effect of Chinese medicine. A novel approach was proposed here to integrate network pharmacology analysis and ingredient content in Chinese medicine to identify active ingredients. The therapeutic action of Xuesaitong (XST) injection on myocardial infarction was analyzed as an example in this study. Firstly, we built a cardiovascular disease (CVD) related protein–protein interaction (PPI) network. Secondly, the potential targets of the ingredients of XST were identified by integrating microarray data, text mining and pharmacophore model-based prediction. The target–ingredient relationships were then mapped to the network. Topological attributes related to the targets of these ingredients, together with the ingredients’ contents, were combined to calculate a composition-weighted index for integrative evaluation of ingredient efficacy. Our results indicated that major active ingredients in XST were notoginsenoside R1, ginsenoside Rg1, Rb1, Rd and Re, which was further validated on myocardial infarction rat models. In conclusion, this study presented a novel approach to identify active ingredients in Chinese medicine.
Co-reporter:Li Xing;Leihong Wu;Yufeng Liu;Ni Ai;Xiaoyan Lu
Journal of Applied Toxicology 2014 Volume 34( Issue 7) pp:805-809
Publication Date(Web):
DOI:10.1002/jat.2923
ABSTRACT
Toxicogenomics (TGx) has played a significant role in mechanistic research related with hepatotoxicity as well as liver toxicity prediction. Currently, several large-scale preclinical TGx data sets were made freely accessible to the public, such as Open TG-GATEs. With the availability of a sufficient amount of microarray data, it is important to integrate this information to provide new insights into the risk assessment of potential drug-induced liver toxicity. Here we developed a web server for evaluating the potential liver toxicity based on genome-wide transcriptomics data, namely LTMap. In LTMap, researchers could compare signatures of query compounds against a pregenerated signature database of 20 123 Affymetrix arrays associated with about 170 compounds retrieved from the largest public toxicogenomics data set Open TG-GATEs. Results from this comparison may lead to the unexpected discovery of similar toxicological responses between chemicals. We validated our computational approach for similarity comparison using three example drugs. Our successful applications of LTMap in these case studies demonstrated its utility in revealing the connection of chemicals according to similar toxicological behaviors. Furthermore, a user-friendly web interface is provided by LTMap to browse and search toxicogenomics data (http://tcm.zju.edu.cn/ltmap). Copyright © 2013 John Wiley & Sons, Ltd.
Co-reporter:Shun Xiao, Cui Hao, Ni Ai, Kedi Luo, Xuexun Wen, Shufang Wang and Xiaohui Fan
Analytical Methods 2014 vol. 6(Issue 23) pp:9283-9290
Publication Date(Web):14 Oct 2014
DOI:10.1039/C4AY01972E
For traditional Chinese medicine (TCM), its most common application form is TCM formulae that assemble herbs and other materials together to treat diseases. According to the shared herbs or similar indications, most TCM formulae (Fangji or FJ in Chinese) can be grouped into several categories, namely analogous TCM formulae. Similarities/dissimilarities between these analogous TCM formulae provide a unique opportunity to understand mechanisms of action of TCM and discover biologically active compounds or components, as well as rationalize clinical use of TCM formulae. In this work, high performance liquid chromatography-mass spectrometry (HPLC-MS) coupled with microplate-based rapid screening assays was used to carry out systematic chemical analysis of the Wu-Ling-San (WLS) formula group. A total of thirty-seven compounds were identified in WLS and their MS fragmentation pathways were clarified. Seven potential anti-inflammatory components were discovered in WLS and other three analogous formulae by nitric oxide assay-based screening. The differences in chemical profiles and related mechanisms of action of the WLS group were discussed, which were reported for the first time and would be helpful for further pharmacological studies. Our results showed that this method is very effective and powerful for the research into TCM analogous formulae.
Co-reporter:Leihong Wu;Yi Wang;Zheng Li;Boli Zhang;Yiyu Cheng
Chinese Medicine 2014 Volume 9( Issue 1) pp:
Publication Date(Web):2014 December
DOI:10.1186/1749-8546-9-24
The role of “Jun-Chen-Zuo-Shi” (also known as “sovereign-minister-assistant-courier”) component herbs of Chinese medicine is not fully understood. This study aims to test the “Jun-Chen-Zuo-Shi” rule with the QiShenYiQi formula (QSYQ) on treating acute myocardial ischemia (AMI) by a network pharmacology approach.An Acute Myocardial Ischemia (AMI) specific Organism Disturbed Network (AMI-ODN), was constructed by integrating data of disease-associated genes, protein-protein interaction and microarray experiments. A network-based index, Network Recovery Index for Organism Disturbed Network (NRI-ODN), was developed to measure the therapeutic efficacy of QSYQ and its ingredients, i.e., the ability to recover disturbed AMI network model back to normal state.The whole formula of QSYQ got a NRI-ODN score of 864.48, which outperformed all individual herbs. Additionally, the primary component herbs, Radix Astragalus membranaceus and Radix Salvia miltiorrrhiza showed NRI-DON score of 680.27 and 734.31 respectively, which meant a better performance to recover disturbed AMI network than the supplementary component herbs, Panax notoginseng and Dalbergia sissoo did (545.76 and 584.88, respectively).AMI-ODN model and NRI-ODN identified the possible roles of “Jun-Chen-Zuo-Shi” component herbs of QSYQ in treating AMI at molecular network and pathway level.
Co-reporter:Jihong Yang;Yufeng Liu;Zheng Li;Yiyu Cheng
Heart Failure Reviews 2014 Volume 19( Issue 6) pp:799-814
Publication Date(Web):2014 November
DOI:10.1007/s10741-013-9417-4
It is well established that cardiac remodeling plays a pivotal role in the development of heart failure, a leading cause of death worldwide. Meanwhile, sympathetic hyperactivity is an important factor in inducing cardiac remodeling. Therefore, an in-depth understanding of beta-adrenoceptor signaling pathways would help to find better ways to reverse the adverse remodeling. Here, we reviewed five pathways, namely mitogen-activated protein kinase signaling, Gs–AC–cAMP signaling, Ca2+-calcineurin-NFAT/CaMKII-HDACs signaling, PI3K signaling and beta-3 adrenergic signaling, in cardiac remodeling. Furthermore, we constructed a cardiac-remodeling-specific regulatory network including miRNA, transcription factors and target genes within the five pathways. Both experimental and clinical studies have documented beneficial effects of beta blockers in cardiac remodeling; nevertheless, different blockers show different extent of therapeutic effect. Exploration of the underlying mechanisms could help developing more effective drugs. Current evidence of treatment effect of beta blockers in remodeling was also reviewed based upon information from experimental data and clinical trials. We further discussed the mechanism of how beta blockers work and why some beta blockers are more potent than others in treating cardiac remodeling within the framework of cardiac remodeling network.
Co-reporter:Leihong Wu, Ni Ai, Yufeng Liu, Yi Wang, and Xiaohui Fan
Journal of Chemical Information and Modeling 2013 Volume 53(Issue 8) pp:2154-2160
Publication Date(Web):July 28, 2013
DOI:10.1021/ci400155x
The anatomical therapeutic chemical (ATC) system is a world standard to define drug indications. Despite its broad applications in pharmaceutical and biomedical research, only a few studies that examine the relationships among ATC classes have been published. Here we present a similarity-based approach, named the indication similarity ensemble approach (iSEA), that innovatively correlates ATC classes by their drug set similarity. Our study demonstrated that iSEA was capable of relating ATC classes, and these relationships could accurately assign the right indications for approved drugs and make reasonable predictions about possible clinical indications for unclassified drugs, which would provide valuable information for drug repositioning. Additionally, on the basis of iSEA, we constructed the first ATC relationship network to reflect correlations among ATCs from a network view, which would further render novel insight to understand the intrinsic relationships in the ATC system.
Co-reporter:Jianping Huang
Molecular Diversity 2013 Volume 17( Issue 1) pp:63-73
Publication Date(Web):2013 February
DOI:10.1007/s11030-012-9415-9
Predictability and prediction reliability are of utmost important to characterize a good Quantitative structure–activity relationships (QSAR) model. However, validation methods are insufficient to guarantee the prediction reliability of QSAR models. Moreover, high dimensional samples also pose great challenge to traditional methods in terms of predictive power. Therefore, this study presents a predictive classifier (i.e., TreeEC) that can assess prediction reliability with high confidence, especially for facing high dimensional QSAR data. Two approaches for assessing prediction reliability are provided, i.e., applicability domain and prediction confidence. We demonstrate that the applicability domain has difficulty to guarantee the models’ prediction reliability, where samples intensively close to the domain center are often poor predicted than those outside the domain. Instead, prediction confidence is more promising for assessing prediction reliability. Based on a large data set assessed by prediction confidence, external samples assessed with high confidence greater than 95 % can be reliably predicted with an accuracy of 94 %, in contrast to the average accuracy of 84 %. We also illustrate that TreeEC are less affected by high dimensionality than other popular methods according to 11 public data sets. A free version of TreeEC with a user-friendly interface can also be downloading from website http://pharminfo.zju.edu.cn/computation/TreeEC/TreeEC.html.
Co-reporter:Yufeng Zhang, Jianyang Pan, Jinghua Zhong, Yi Wang, Xiaohui Fan, Yiyu Cheng
Journal of Chromatography A 2012 Volume 1227() pp:181-193
Publication Date(Web):2 March 2012
DOI:10.1016/j.chroma.2012.01.006
In the present study, a tool called classifier for traditional Chinese medicine (CTCM) was developed to facilitate the discrimination of phytochemical constituents in two-dimensional datasets of liquid chromatography/mass spectrometry (LC/MS). Based on the full mass spectral characteristics of components in a mixture, particularly their adduct-ion patterns, an entire LC/MS dataset can be separated into several sub-datasets, each corresponding to one or several types of natural products. CTCM has been verified using 24 standard compounds and successfully applied in two previously reported LC/MS datasets, which confirmed the capability of proposed tool to extract adduct-ion patterns from LC/MS datasets. Moreover, the LC/MS dataset of a Wei-Fu-Chun (WFC) tablet, a prescription drug consisting of three crude herbs used for the treatment of enteric diseases, was analyzed using CTCM. The analysis indicated that the compounds in WFC could be split into three groups, with the main constituents including saponins from Radix Ginseng Rubra, flavonoids from Fructus aurantii, and phenolic compounds from Isodon amethystoides. The major compounds in the three groups were either positively identified or tentatively characterized by multi-stage and high resolution MS. The proposed tool provides a novel approach for processing the LC/MS datasets of complex samples, such as traditional Chinese medicine and botanical drugs.Highlights► We developed a tool (CTCM) to classify the constituents in herbal extracts after LC/MS analysis. ► This classification is based on the adduct-ion patterns of compounds in their full mass spectra. ► Peaks in the sub-datasets obtained from CTCM could be easily picked out. ► The chemical components in WFC tablet were systemically identified.
Co-reporter:Yi Wang, Xiaoping Zhao, Xiumei Gao, Xiaojing Nie, Yingxin Yang, Xiaohui Fan
Analytica Chimica Acta 2012 710() pp: 131
Publication Date(Web):13 January 2012
DOI:10.1016/j.aca.2011.10.037
Co-reporter:Yi Wang, Xiaoping Zhao, Xiumei Gao, Xiaojing Nie, Yingxin Yang, Xiaohui Fan
Analytica Chimica Acta 2011 Volume 702(Issue 1) pp:87-94
Publication Date(Web):19 September 2011
DOI:10.1016/j.aca.2011.06.020
Medicinal plants have been widely recognized as a renewable resource for the discovery of novel leads and drug. In this study, an approach for screening and identification compounds with cardioprotective activity from medicinal plant extracts by cellular-fluorescence imaging technique was developed. It is a cell-based assay for measuring mitochondrial membrane potential changes in H9c2 cardiac muscle cells exposed to H2O2 by using a fluorescence automatic microscopy screening platform. Rhodamine 123 was used as the fluorescent dye to indicate the change of mitochondrial membrane potential. The sensitivity and linear range of the proposed approach were evaluated and validated using vitamin C, an antioxidative compound. The method was applied to screen active components with potent cardioprotective effects from a traditional Chinese formula. The potential cardioprotective components were identified by liquid chromatography coupled with mass spectrometry (LC/MS). Moreover, the utility of the proposed approach was further validated by three compounds (salvianolic acid B, protocatechuic aldehyde, and tanshinone II A) identified from the formula which showed cardioprotective effects in a dose-dependent manner. These applications suggested that the proposed rapid and sensitive screening approach offers an efficient way to discover active components or compounds from medicinal plants.Graphical abstractHighlights• Based on cellular-fluorescence imaging technique combined with LC/MS, a rapid approach was constructed to discover active compounds from medicinal plants. • Rhodamine 123 was used as the fluorescent dye to indicate the change of mitochondrial membrane potential. • Good sensitivity and linear range in live cellular fluorescence imaging. • Cardioprotective components from Qi-Shen-Yi-Qi formula were screened and identified.
Co-reporter:Jianping Huang and Xiaohui Fan
Molecular Pharmaceutics 2011 Volume 8(Issue 2) pp:600-608
Publication Date(Web):March 3, 2011
DOI:10.1021/mp100423u
Although a number of pitfalls of QSAR have been corrected in the past decade, the reliability of QSAR models is still insufficient. The reason why QSAR fails is still under hot debate; our study attempts to address this topic from a practical and empirical perspective, evaluating two relatively large toxicological data sets using a typical combination of support vector machine (SVM) and genetic algorithm (GA). Our results suggest that the vast number of equivalent models to be chosen and the insufficient validation strategy are primarily responsible for the failure of many QSAR models. First, a method often produces much more equivalent models than we might expect, and the corresponding descriptor sets show little overlap, indicating the unreliability of the conventional approaches. Moreover, although external validation has been considered necessary, validation on an arbitrarily selected independent set is still insufficient to guarantee the true predictability of a QSAR model. Therefore, more effective training and validation strategies are demanded to enhance the reliability of QSAR models. The present study also demonstrates that combinatorial or ensemble models can greatly reduce the variance of equivalent models, and that models built with the most frequently selected descriptors used by the equivalent models seem to yield more promising performances.Keywords: combinatorial model; ensemble method; external validation; genetic algorithm; predictability; QSAR modeling; reliability; support vector machine;
Co-reporter:Peiying Shi;Yufeng Zhang;Haibin Qu
Phytochemical Analysis 2011 Volume 22( Issue 1) pp:66-73
Publication Date(Web):
DOI:10.1002/pca.1253
Abstract
Introduction – Ixeris sonchifolia (Bunge) Hance, a folk medicine, has been widely used in China for its anti-inflammatory and haemostatic effects. However, the miscellaneous component composition of this herbal medicine is not well known.
Objective – To develop a fast and comprehensive analytical method for the characterisation of various components from I. Sonchifolia, as a tool for the quality control of the herb and its related preparations.
Methodology – Ixeris sonchifolia samples were extracted with 60% aqueous methanol, purified by solid-phase extraction and then analysed by the combinatorial use of HPLC-TOFMS and HPLC-ITMS.
Results – A total of six sesquiterpene lactones, six phenolic acids and seven flavonoids were identified or tentatively characterised. Five of them were reported for the first time in I. sonchifolia and, in particular, two amino acid-sesquiterpene lactone conjugates, 11,13-dihydro-13-prolyl-ixerin Z and 11,13-dihydro-13-prolyl-ixerin Z1, that were first found in this plant source.
Conclusion – A global profile of I. sonchifolia constituents was described, which could be useful for the quality control of this herb and its related preparations. The employed combination of HPLC-TOFMS and HPLC-ITMS could also be a promising tool for the analysis of other herbal medicines containing sesquiterpene lactones, phenolic acids or flavonoids. Copyright © 2010 John Wiley & Sons, Ltd.
Co-reporter:Li Shao, Leihong Wu, Xiaohui Fan, and Yiyu Cheng
Journal of Chemical Information and Modeling 2010 Volume 50(Issue 11) pp:1941-1948
Publication Date(Web):November 4, 2010
DOI:10.1021/ci100305g
Co-reporter:Hong Yao, Peiying Shi, Ling Zhang, Xiaohui Fan, Qing Shao and Yiyu Cheng
Molecular BioSystems 2010 vol. 6(Issue 6) pp:1061-1070
Publication Date(Web):19 Mar 2010
DOI:10.1039/B925612A
Although some important biomarkers for myocardial injury have been identified, there still lacks a systematic view of the development and progression of myocardial infarction, including enzymatic regulation, metabolite levels, fluxes, etc., which are pivotal to elucidate the physiological mechanism of disease. Here we present an untargeted analytical approach based on gas chromatography coupled with mass spectrometry (GC-MS) to map the temporal metabolic profilings in blood sera of myocardial infarction rat model prepared by left coronary artery ligation. Using XCMS software (http://metlin.scripps.edu/download/), data processing was simplified greatly. We identified the changes in circulating levels of 24 metabolites during the myocardial ischemia. By combination of previous proteomic results, it gives rise to a new insight view of energy metabolism changes referring to anaerobic glycolysis, citric acid cycle, fatty acid β-oxidation, and some amino acids metabolism. With these altered metabolism pathways as possible drug targets, we validated a role for the presented metabonomic profiling in the systematic understanding of the action mechanism of component-complex medicine herbs, such as Radix Ophiopogonis, a widely-used anti-myocardial ischemia herbal medicine in Asia.
Co-reporter:Ni Ai, Xiaohui Fan, Sean Ekins
Advanced Drug Delivery Reviews (23 June 2015) Volume 86() pp:46-60
Publication Date(Web):23 June 2015
DOI:10.1016/j.addr.2015.03.006
Drug–drug interactions (DDIs) are associated with severe adverse effects that may lead to the patient requiring alternative therapeutics and could ultimately lead to drug withdrawal from the market if they are severe. To prevent the occurrence of DDI in the clinic, experimental systems to evaluate drug interaction have been integrated into the various stages of the drug discovery and development process. A large body of knowledge about DDI has also accumulated through these studies and pharmacovigillence systems. Much of this work to date has focused on the drug metabolizing enzymes such as cytochrome P-450s as well as drug transporters, ion channels and occasionally other proteins. This combined knowledge provides a foundation for a hypothesis-driven in silico approach, using either cheminformatics or physiologically based pharmacokinetics (PK) modeling methods to assess DDI potential. Here we review recent advances in these approaches with emphasis on hypothesis-driven mechanistic models for important protein targets involved in PK-based DDI. Recent efforts with other informatics approaches to detect DDI are highlighted. Besides DDI, we also briefly introduce drug interactions with other substances, such as Traditional Chinese Medicines to illustrate how in silico modeling can be useful in this domain. We also summarize valuable data sources and web-based tools that are available for DDI prediction. We finally explore the challenges we see faced by in silico approaches for predicting DDI and propose future directions to make these computational models more reliable, accurate, and publically accessible.Download high-res image (99KB)Download full-size image
Co-reporter:Shuyu Zhan, Wenjing Guo, Qing Shao, Xiaohui Fan, Zheng Li, Yiyu Cheng
Journal of Ethnopharmacology (14 March 2014) Volume 152(Issue 2) pp:333-339
Publication Date(Web):14 March 2014
DOI:10.1016/j.jep.2014.01.014
Ethnopharmacological relevanceGinsenoside Rg1, ginsenoside Rb1 and schizandrin are main bioactive components from Panax ginseng and Schisandra chinensis. They have been found in many prescriptions of Traditional Chinese Medicines (TCM) and proven to be effective for prevention and treatment of cardiovascular disease. It is valuable to investigate their pharmacokinetic and pharmacodynamic behavior and potential synergistic effect for better drug development and clinical application.Materials and methodsPharmacokinetic and nitric oxide (NO) release pharmacodynamic drug–drug interactions of ginsenoside Rg1, ginsenoside Rb1 and schisandrin were studied after intravenous administration of each compound with the dose of 10 mg/kg and their mixture with the total dose of 10 mg/kg to isoproterenol (ISO)-induced myocardial ischemia rats. Drug concentrations in serum were determined using LC–MS method. Nitrite and nitrate (NOx−), the predominant oxidation product of NO in serum was used as an effective marker and quantitated by the method of high-performance liquid chromatography coupled with fluorescence detection (HPLC-FL). The main pharmacokinetic parameters of T1/2β, MRT0−∞, Vd, Cl, and AUC, and the main pharmacodynamic parameters of Cmax, Tmax and AUEC were calculated by non-compartment model.ResultsThe results indicated ginsenoside Rb1 and (or) schisandrin in mixture could significantly postpone the elimination of ginsenoside Rg1 in rat serum. Co-administration of three compounds markedly increased the systemic exposure level of each compound in vivo. Ginsenoside Rg1 and ginsenoside Rb1 had the effect of inducing real-time NO release in rats concentration dependently. Schisandrin had no effect of inducing real-time NO release in this study. The mixture of ginsenoside Rg1, Rb1 and schisandrin administration exhibited synergistic effect of inducing NO release in ISO treated rats.ConclusionsThe result obtained from this study suggested pharmacokinetic and pharmacodynamic drug–drug interactions between ginsenoside Rg1, Rb1 and schisandrin. The study provided valuable information for drug development and clinical application of TCM.Download high-res image (236KB)Download full-size image
Co-reporter:
Analytical Methods (2009-Present) 2014 - vol. 6(Issue 23) pp:
Publication Date(Web):
DOI:10.1039/C4AY01972E
For traditional Chinese medicine (TCM), its most common application form is TCM formulae that assemble herbs and other materials together to treat diseases. According to the shared herbs or similar indications, most TCM formulae (Fangji or FJ in Chinese) can be grouped into several categories, namely analogous TCM formulae. Similarities/dissimilarities between these analogous TCM formulae provide a unique opportunity to understand mechanisms of action of TCM and discover biologically active compounds or components, as well as rationalize clinical use of TCM formulae. In this work, high performance liquid chromatography-mass spectrometry (HPLC-MS) coupled with microplate-based rapid screening assays was used to carry out systematic chemical analysis of the Wu-Ling-San (WLS) formula group. A total of thirty-seven compounds were identified in WLS and their MS fragmentation pathways were clarified. Seven potential anti-inflammatory components were discovered in WLS and other three analogous formulae by nitric oxide assay-based screening. The differences in chemical profiles and related mechanisms of action of the WLS group were discussed, which were reported for the first time and would be helpful for further pharmacological studies. Our results showed that this method is very effective and powerful for the research into TCM analogous formulae.
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![6-O-beta-D-glucopyranosyl-1-O-[(2,6,6-trimethylcyclohex-1-en-1-yl)carbonyl]-beta-D-glucopyranose](http://img.cochemist.com/ccimg/1401000/1400912-98-2_b.png)
![(4R)-4-{{6-O-[(2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)-1-oxoprop-2-en-1-yl]-beta-D-glucopyranosyl}oxy}-2,6,6-trimethylcyclohex-1-ene-1-carboxylic acid](http://img.cochemist.com/ccimg/1229700/1229609-48-6.png)
![(4R)-4-{{6-O-[(2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)-1-oxoprop-2-en-1-yl]-beta-D-glucopyranosyl}oxy}-2,6,6-trimethylcyclohex-1-ene-1-carboxylic acid](http://img.cochemist.com/ccimg/1229700/1229609-48-6_b.png)
![(3-methoxy-5H-9,11-dioxabenzo[3,4]cyclohepta[1,2-f]inden-7-yl)methanol](http://img.cochemist.com/ccimg/1188000/1187955-78-7.png)
![(3-methoxy-5H-9,11-dioxabenzo[3,4]cyclohepta[1,2-f]inden-7-yl)methanol](http://img.cochemist.com/ccimg/1188000/1187955-78-7_b.png)
![Azuleno[4,5-b]furan-3-methanesulfonicacid, dodecahydro-6,9-bis(methylene)-2-oxo-, (3R,3aS,6aR,9aR,9bS)-](http://img.cochemist.com/ccimg/1059700/1059671-65-6.png)
![Azuleno[4,5-b]furan-3-methanesulfonicacid, dodecahydro-6,9-bis(methylene)-2-oxo-, (3R,3aS,6aR,9aR,9bS)-](http://img.cochemist.com/ccimg/1059700/1059671-65-6_b.png)
![Azuleno[4,5-b]furan-3-methanesulfonicacid, dodecahydro-6,9-bis(methylene)-2-oxo-, (3S,3aS,6aR,9aR,9bS)-](http://img.cochemist.com/ccimg/1017000/1016983-51-9.png)
![Azuleno[4,5-b]furan-3-methanesulfonicacid, dodecahydro-6,9-bis(methylene)-2-oxo-, (3S,3aS,6aR,9aR,9bS)-](http://img.cochemist.com/ccimg/1017000/1016983-51-9_b.png)
![[4]-shogaol](http://img.cochemist.com/ccimg/211200/211176-76-0.png)
![[4]-shogaol](http://img.cochemist.com/ccimg/211200/211176-76-0_b.png)
![(5alpha,8xi,9xi,12alpha,13xi,14beta)-12-hydroxy-17-[(2S)-2-hydroxy-6-methylhept-5-en-2-yl]-4,4,5,10,14-pentamethylgonan-3-yl 2-O-(6-O-acetyl-beta-D-glucopyranosyl)-beta-D-glucopyranoside](http://img.cochemist.com/ccimg/194900/194861-70-6.png)
![(5alpha,8xi,9xi,12alpha,13xi,14beta)-12-hydroxy-17-[(2S)-2-hydroxy-6-methylhept-5-en-2-yl]-4,4,5,10,14-pentamethylgonan-3-yl 2-O-(6-O-acetyl-beta-D-glucopyranosyl)-beta-D-glucopyranoside](http://img.cochemist.com/ccimg/194900/194861-70-6_b.png)
![(3beta,12beta,23E)-20-[(6-O-beta-D-glucopyranosyl-beta-D-glucopyranosyl)oxy]-12,25-dihydroxydammar-23-en-3-yl 2-O-beta-D-glucopyranosyl-beta-D-glucopyranoside](http://img.cochemist.com/ccimg/193900/193895-21-5.png)
![(3beta,12beta,23E)-20-[(6-O-beta-D-glucopyranosyl-beta-D-glucopyranosyl)oxy]-12,25-dihydroxydammar-23-en-3-yl 2-O-beta-D-glucopyranosyl-beta-D-glucopyranoside](http://img.cochemist.com/ccimg/193900/193895-21-5_b.png)
![(E)-3-(3,4-DIHYDROXY-2-METHOXYPHENYL)-1-[4-HYDROXY-3-(3-METHYLBUT-2-ENYL)PHENYL]PROP-2-EN-1-ONE](http://img.cochemist.com/data/images/144506-15-0.png)
![(E)-3-(3,4-DIHYDROXY-2-METHOXYPHENYL)-1-[4-HYDROXY-3-(3-METHYLBUT-2-ENYL)PHENYL]PROP-2-EN-1-ONE](http://img.cochemist.com/data/images/144506-15-0_b.png)
![b-D-Glucopyranoside,2-(3,4-dihydroxyphenyl)ethyl O-b-D-galactopyranosyl-(1®2)-O-6-deoxy-a-L-mannopyranosyl-(1®3)-, 4-[(2E)-3-(3,4-dihydroxyphenyl)-2-propenoate]](http://img.cochemist.com/ccimg/143700/143617-02-1.png)
![b-D-Glucopyranoside,2-(3,4-dihydroxyphenyl)ethyl O-b-D-galactopyranosyl-(1®2)-O-6-deoxy-a-L-mannopyranosyl-(1®3)-, 4-[(2E)-3-(3,4-dihydroxyphenyl)-2-propenoate]](http://img.cochemist.com/ccimg/143700/143617-02-1_b.png)
![1,3-Benzenediol,4-[(3R)-3,4-dihydro-5,7-dimethoxy-6-(3-methyl-2-buten-1-yl)-2H-1-benzopyran-3-yl]-](http://img.cochemist.com/ccimg/142600/142561-10-2.png)
![1,3-Benzenediol,4-[(3R)-3,4-dihydro-5,7-dimethoxy-6-(3-methyl-2-buten-1-yl)-2H-1-benzopyran-3-yl]-](http://img.cochemist.com/ccimg/142600/142561-10-2_b.png)
![5,7-dihydroxy-2-[4-hydroxy-3-(3-methylbut-2-en-1-yl)phenyl]-6-(3-methylbut-2-en-1-yl)-4H-chromen-4-one](http://img.cochemist.com/ccimg/135000/134958-52-4.png)
![5,7-dihydroxy-2-[4-hydroxy-3-(3-methylbut-2-en-1-yl)phenyl]-6-(3-methylbut-2-en-1-yl)-4H-chromen-4-one](http://img.cochemist.com/ccimg/135000/134958-52-4_b.png)
![4H-1-Benzopyran-4-one,3-[3,4-dihydroxy-5-(3-methyl-2-buten-1-yl)phenyl]-5,7-dihydroxy-6-(3-methyl-2-buten-1-yl)-](http://img.cochemist.com/ccimg/129300/129280-34-8.png)
![4H-1-Benzopyran-4-one,3-[3,4-dihydroxy-5-(3-methyl-2-buten-1-yl)phenyl]-5,7-dihydroxy-6-(3-methyl-2-buten-1-yl)-](http://img.cochemist.com/ccimg/129300/129280-34-8_b.png)
![4-[6-hydroxy-4-methoxy-5-(3-methylbut-2-en-1-yl)-1-benzofuran-2-yl]benzene-1,3-diol](http://img.cochemist.com/ccimg/118600/118524-14-4.png)
![4-[6-hydroxy-4-methoxy-5-(3-methylbut-2-en-1-yl)-1-benzofuran-2-yl]benzene-1,3-diol](http://img.cochemist.com/ccimg/118600/118524-14-4_b.png)
![b-D-Allopyranoside,2-(3,4-dihydroxyphenyl)ethyl O-6-deoxy-a-L-mannopyranosyl-(1®2)-O-[b-D-glucopyranosyl-(1®6)]-, 3-[(2E)-3-(3,4-dihydroxyphenyl)-2-propenoate] (9CI)](http://img.cochemist.com/ccimg/116900/116872-05-0.png)
![b-D-Allopyranoside,2-(3,4-dihydroxyphenyl)ethyl O-6-deoxy-a-L-mannopyranosyl-(1®2)-O-[b-D-glucopyranosyl-(1®6)]-, 3-[(2E)-3-(3,4-dihydroxyphenyl)-2-propenoate] (9CI)](http://img.cochemist.com/ccimg/116900/116872-05-0_b.png)
![4H-1-Benzopyran-4-one,7-[(6-O-D-apio-b-D-furanosyl-b-D-glucopyranosyl)oxy]-2,3-dihydro-5-hydroxy-2-(4-hydroxyphenyl)-,(2S)- (9CI)](http://img.cochemist.com/ccimg/116300/116271-35-3.png)
![4H-1-Benzopyran-4-one,7-[(6-O-D-apio-b-D-furanosyl-b-D-glucopyranosyl)oxy]-2,3-dihydro-5-hydroxy-2-(4-hydroxyphenyl)-,(2S)- (9CI)](http://img.cochemist.com/ccimg/116300/116271-35-3_b.png)
![b-D-Allopyranoside,2-(3,4-dihydroxyphenyl)ethyl 2-O-(6-deoxy-a-L-mannopyranosyl)-,3-[(2E)-3-(3,4-dihydroxyphenyl)-2-propenoate] (9CI)](http://img.cochemist.com/ccimg/113600/113557-95-2.png)
![b-D-Allopyranoside,2-(3,4-dihydroxyphenyl)ethyl 2-O-(6-deoxy-a-L-mannopyranosyl)-,3-[(2E)-3-(3,4-dihydroxyphenyl)-2-propenoate] (9CI)](http://img.cochemist.com/ccimg/113600/113557-95-2_b.png)
![(2r,6s)-6-[(3s,5r,10s,12s,13r,14r,17r)-12-acetyloxy-3-hydroxy-4,4,10,13,14-pentamethyl-7,11,15-trioxo-1,2,3,5,6,12,16,17-octahydrocyclopenta[a]phenanthren-17-yl]-2-methyl-4-oxoheptanoic Acid](http://img.cochemist.com/ccimg/98700/98665-19-1.png)
![(2r,6s)-6-[(3s,5r,10s,12s,13r,14r,17r)-12-acetyloxy-3-hydroxy-4,4,10,13,14-pentamethyl-7,11,15-trioxo-1,2,3,5,6,12,16,17-octahydrocyclopenta[a]phenanthren-17-yl]-2-methyl-4-oxoheptanoic Acid](http://img.cochemist.com/ccimg/98700/98665-19-1_b.png)
![[6-[2-(3,4-dihydroxyphenyl)ethoxy]-5-hydroxy-4-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy-2-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxymethyl]oxan-3-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate](http://img.cochemist.com/ccimg/94100/94079-81-9.png)
![[6-[2-(3,4-dihydroxyphenyl)ethoxy]-5-hydroxy-4-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy-2-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxymethyl]oxan-3-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate](http://img.cochemist.com/ccimg/94100/94079-81-9_b.png)
![b-D-Glucopyranoside, (3b,12b)-20-[(6-O-b-D-glucopyranosyl-b-D-glucopyranosyl)oxy]-12-hydroxydammar-24-en-3-yl2-O-[6-O-(carboxyacetyl)-b-D-glucopyranosyl]-](http://img.cochemist.com/ccimg/88200/88140-34-5.png)
![b-D-Glucopyranoside, (3b,12b)-20-[(6-O-b-D-glucopyranosyl-b-D-glucopyranosyl)oxy]-12-hydroxydammar-24-en-3-yl2-O-[6-O-(carboxyacetyl)-b-D-glucopyranosyl]-](http://img.cochemist.com/ccimg/88200/88140-34-5_b.png)
![4-[5-hydroxy-6-(2-hydroxy-3-methyl-4-methylideneoxolan-2-yl)-1,3-dioxan-4-yl]piperidine-2,6-dione](http://img.cochemist.com/ccimg/85800/85719-78-4.png)
![4-[5-hydroxy-6-(2-hydroxy-3-methyl-4-methylideneoxolan-2-yl)-1,3-dioxan-4-yl]piperidine-2,6-dione](http://img.cochemist.com/ccimg/85800/85719-78-4_b.png)
![(3beta,12beta)-20-[(6-O-beta-glucopyranosyl-beta-D-glucopyranosyl)oxy]-12-hydroxydammar-24-en-3-yl 2-O-(6-O-acetyl-beta-D-glucopyranosyl)-beta-D-glucopyranoside](http://img.cochemist.com/ccimg/85100/85013-02-1.png)
![(3beta,12beta)-20-[(6-O-beta-glucopyranosyl-beta-D-glucopyranosyl)oxy]-12-hydroxydammar-24-en-3-yl 2-O-(6-O-acetyl-beta-D-glucopyranosyl)-beta-D-glucopyranoside](http://img.cochemist.com/ccimg/85100/85013-02-1_b.png)
![[(2r,3r,4r,5r,6r)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-5-hydroxy-2-[[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-4-[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl] (e)-3-(3,4-dihydroxyphenyl)prop-2-enoate](http://img.cochemist.com/ccimg/82900/82854-37-3.png)
![[(2r,3r,4r,5r,6r)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-5-hydroxy-2-[[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-4-[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl] (e)-3-(3,4-dihydroxyphenyl)prop-2-enoate](http://img.cochemist.com/ccimg/82900/82854-37-3_b.png)
![4H-1-Benzopyran-4-one,2,3-dihydro-5,7-dihydroxy-2-[4-hydroxy-3-(3-methyl-2-buten-1-yl)phenyl]-8-(3-methyl-2-buten-1-yl)-,(2S)-](http://img.cochemist.com/ccimg/80600/80510-05-0.png)
![4H-1-Benzopyran-4-one,2,3-dihydro-5,7-dihydroxy-2-[4-hydroxy-3-(3-methyl-2-buten-1-yl)phenyl]-8-(3-methyl-2-buten-1-yl)-,(2S)-](http://img.cochemist.com/ccimg/80600/80510-05-0_b.png)
ethanoic acid](http://img.cochemist.com/ccimg/66500/66427-92-7.png)
ethanoic acid](http://img.cochemist.com/ccimg/66500/66427-92-7_b.png)
![3-[2,4-dihydroxy-3-(3-methylbut-2-en-1-yl)phenyl]-5,7-dihydroxy-4H-chromen-4-one](http://img.cochemist.com/ccimg/66100/66056-19-7.png)
![3-[2,4-dihydroxy-3-(3-methylbut-2-en-1-yl)phenyl]-5,7-dihydroxy-4H-chromen-4-one](http://img.cochemist.com/ccimg/66100/66056-19-7_b.png)
![(1S)-1,5-anhydro-1-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-6-yl]-2-O-beta-D-glucopyranosyl-D-glucitol](http://img.cochemist.com/ccimg/60800/60767-80-8.png)
![(1S)-1,5-anhydro-1-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-6-yl]-2-O-beta-D-glucopyranosyl-D-glucitol](http://img.cochemist.com/ccimg/60800/60767-80-8_b.png)
![2-Butanone,4-[4-[[6-O-(3,4,5-trihydroxybenzoyl)-b-D-glucopyranosyl]oxy]phenyl]-](http://img.cochemist.com/ccimg/59300/59282-56-3.png)
![2-Butanone,4-[4-[[6-O-(3,4,5-trihydroxybenzoyl)-b-D-glucopyranosyl]oxy]phenyl]-](http://img.cochemist.com/ccimg/59300/59282-56-3_b.png)
![5-(2-Chlorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine](http://img.cochemist.com/ccimg/55200/55142-85-3.png)
![5-(2-Chlorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine](http://img.cochemist.com/ccimg/55200/55142-85-3_b.png)
![Cyclopenta[c]pyran-4-carboxylic acid, 1-(β-D-glucopyranosyloxy)-1,4a,7,7a-tetrahydro-7-hydroxy-7-(hydroxymethyl)-, methyl ester, (1S,4aS,7R,7aS)-](/data/chemimg/1846600/54712-59-3.png)
![Cyclopenta[c]pyran-4-carboxylic acid, 1-(β-D-glucopyranosyloxy)-1,4a,7,7a-tetrahydro-7-hydroxy-7-(hydroxymethyl)-, methyl ester, (1S,4aS,7R,7aS)-](/data/chemimg/1846600/54712-59-3_b.png)
![5,7-DIHYDROXY-2-(4-HYDROXYPHENYL)-6-[(2S,3S,4R,5R,6R)-3,4,5-TRIHYDROXY-6-(HYDROXYMETHYL)OXAN-2-YL]-8-[(2S,3S,4R,5S,6S)-3,4,5-TRIHYDROXY-6-METHYL-OXAN-2-YL]CHROMEN-4-ONE](http://img.cochemist.com/ccimg/40600/40581-17-7.png)
![5,7-DIHYDROXY-2-(4-HYDROXYPHENYL)-6-[(2S,3S,4R,5R,6R)-3,4,5-TRIHYDROXY-6-(HYDROXYMETHYL)OXAN-2-YL]-8-[(2S,3S,4R,5S,6S)-3,4,5-TRIHYDROXY-6-METHYL-OXAN-2-YL]CHROMEN-4-ONE](http://img.cochemist.com/ccimg/40600/40581-17-7_b.png)
![Benzo[g]-1,3-benzodioxolo[5,6-a]quinolizinium,5,6-dihydro-9,10-dimethoxy-13-methyl- (9CI)](http://img.cochemist.com/ccimg/38700/38691-92-8.png)
![Benzo[g]-1,3-benzodioxolo[5,6-a]quinolizinium,5,6-dihydro-9,10-dimethoxy-13-methyl- (9CI)](http://img.cochemist.com/ccimg/38700/38691-92-8_b.png)
![6H,8H-Benzo[a]pyrano[3,4-g]quinolizin-8-one,12-ethenyl-11-(b-D-glucopyranosyloxy)-5,11,12,12a,13,13a-hexahydro-2-hydroxy-3-methoxy-,(11S,12R,12aS,13aR)-](http://img.cochemist.com/ccimg/34500/34482-51-4.png)
![6H,8H-Benzo[a]pyrano[3,4-g]quinolizin-8-one,12-ethenyl-11-(b-D-glucopyranosyloxy)-5,11,12,12a,13,13a-hexahydro-2-hydroxy-3-methoxy-,(11S,12R,12aS,13aR)-](http://img.cochemist.com/ccimg/34500/34482-51-4_b.png)
![(3WEI )-3-{[6-DEOXY-WEI -L-MANNOPYRANOSYL-(1->2)-[WEI -D-XYLOPYRANOSYL-(1->3)]-WEI -L-ARABINOPYRANOSYL]OXY}-20-HYDROXY-19-OXODAMMAR-24-EN-21-YL WEI -D-GLUCOPYRANOSIDE](http://img.cochemist.com/ccimg/33300/33228-65-8.png)
![(3WEI )-3-{[6-DEOXY-WEI -L-MANNOPYRANOSYL-(1->2)-[WEI -D-XYLOPYRANOSYL-(1->3)]-WEI -L-ARABINOPYRANOSYL]OXY}-20-HYDROXY-19-OXODAMMAR-24-EN-21-YL WEI -D-GLUCOPYRANOSIDE](http://img.cochemist.com/ccimg/33300/33228-65-8_b.png)
![b-D-Glucopyranoside,3-[(1E)-2-(3,4-dihydroxyphenyl)ethenyl]-5-hydroxyphenyl](http://img.cochemist.com/ccimg/29900/29884-49-9.png)
![b-D-Glucopyranoside,3-[(1E)-2-(3,4-dihydroxyphenyl)ethenyl]-5-hydroxyphenyl](http://img.cochemist.com/ccimg/29900/29884-49-9_b.png)
![(2s,3s)-4-[(e)-3-[(1r)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-enyl]-2-(3,4-dihydroxyphenyl)-7-hydroxy-2,3-dihydro-1-benzofuran-3-carboxylic Acid](http://img.cochemist.com/ccimg/28900/28831-65-4.png)
![(2s,3s)-4-[(e)-3-[(1r)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-enyl]-2-(3,4-dihydroxyphenyl)-7-hydroxy-2,3-dihydro-1-benzofuran-3-carboxylic Acid](http://img.cochemist.com/ccimg/28900/28831-65-4_b.png)
![6H-Dibenzo[a,g]quinolizin-3-ol,5,8,13,13a-tetrahydro-2,9,10-trimethoxy-](http://img.cochemist.com/ccimg/27400/27313-86-6.png)
![6H-Dibenzo[a,g]quinolizin-3-ol,5,8,13,13a-tetrahydro-2,9,10-trimethoxy-](http://img.cochemist.com/ccimg/27400/27313-86-6_b.png)
![Butanoic acid,3-(acetyloxy)-3-methyl-,(1S,2'R,6S,7aS)-4-[(acetyloxy)methyl]-6,7a-dihydro-1-(3-methyl-1-oxobutoxy)spiro[cyclopenta[c]pyran-7(1H),2'-oxiran]-6-ylester](http://img.cochemist.com/ccimg/25200/25161-41-5.png)
![Butanoic acid,3-(acetyloxy)-3-methyl-,(1S,2'R,6S,7aS)-4-[(acetyloxy)methyl]-6,7a-dihydro-1-(3-methyl-1-oxobutoxy)spiro[cyclopenta[c]pyran-7(1H),2'-oxiran]-6-ylester](http://img.cochemist.com/ccimg/25200/25161-41-5_b.png)
![6H-Benzofuro[3,2-c][1]benzopyran-6-one,3,9-dihydroxy-1-methoxy-2-(3-methyl-2-buten-1-yl)-](http://img.cochemist.com/ccimg/23100/23013-84-5.png)
![6H-Benzofuro[3,2-c][1]benzopyran-6-one,3,9-dihydroxy-1-methoxy-2-(3-methyl-2-buten-1-yl)-](http://img.cochemist.com/ccimg/23100/23013-84-5_b.png)
![(1S,4aS,5R,7aS)-1-(beta-D-glucopyranosyloxy)-5-hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylic acid](http://img.cochemist.com/ccimg/18900/18842-99-4.png)
![(1S,4aS,5R,7aS)-1-(beta-D-glucopyranosyloxy)-5-hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylic acid](http://img.cochemist.com/ccimg/18900/18842-99-4_b.png)
![Isoquinolinium,1,2,3,4-tetrahydro-7-hydroxy-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2,2-dimethyl-,(1S)-](http://img.cochemist.com/ccimg/18500/18446-73-6.png)
![Isoquinolinium,1,2,3,4-tetrahydro-7-hydroxy-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2,2-dimethyl-,(1S)-](http://img.cochemist.com/ccimg/18500/18446-73-6_b.png)
![10-hydroxy-9-methoxy-5,6-dihydro[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-7-ium](http://img.cochemist.com/ccimg/18300/18207-71-1.png)
![10-hydroxy-9-methoxy-5,6-dihydro[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-7-ium](http://img.cochemist.com/ccimg/18300/18207-71-1_b.png)
![9-hydroxy-10-methoxy-5,6-dihydro[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-7-ium](http://img.cochemist.com/ccimg/17400/17388-19-1.png)
![9-hydroxy-10-methoxy-5,6-dihydro[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-7-ium](http://img.cochemist.com/ccimg/17400/17388-19-1_b.png)
![4H-1-Benzopyran-4-one,7-[[2-O-(6-deoxy-伪-L-mannopyranosyl)-尾-D-glucopyranosyl]oxy]-5-hydroxy-2-(4-hydroxyphenyl)-](http://img.cochemist.com/ccimg/17400/17306-46-6.png)
![4H-1-Benzopyran-4-one,7-[[2-O-(6-deoxy-伪-L-mannopyranosyl)-尾-D-glucopyranosyl]oxy]-5-hydroxy-2-(4-hydroxyphenyl)-](http://img.cochemist.com/ccimg/17400/17306-46-6_b.png)
![[4,8'-Bi-2H-1-benzopyran]-3,3',5,5',7,7'-hexol,2,2'-bis(3,4-dihydroxyphenyl)-3,3',4,4'-tetrahydro-](http://img.cochemist.com/ccimg/15600/15514-06-4.png)
![[4,8'-Bi-2H-1-benzopyran]-3,3',5,5',7,7'-hexol,2,2'-bis(3,4-dihydroxyphenyl)-3,3',4,4'-tetrahydro-](http://img.cochemist.com/ccimg/15600/15514-06-4_b.png)
![(+-)-1-(4-Hydroxy-3-methoxy-phenyl)-2-[2]piperidyl-aethanon](http://img.cochemist.com/ccimg/7400/7363-20-4.png)
![(+-)-1-(4-Hydroxy-3-methoxy-phenyl)-2-[2]piperidyl-aethanon](http://img.cochemist.com/ccimg/7400/7363-20-4_b.png)
![Isoquinolinium,1,2,3,4-tetrahydro-7-hydroxy-1-[(4-hydroxyphenyl)methyl]-6-methoxy-2,2-dimethyl-,(1R)-](http://img.cochemist.com/ccimg/6900/6801-40-7.png)
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![Bis[1,3]benzodioxolo[5,6-a:4',5'-g]quinolizinium,6,7-dihydro-](http://img.cochemist.com/ccimg/3500/3486-66-6.png)
![Bis[1,3]benzodioxolo[5,6-a:4',5'-g]quinolizinium,6,7-dihydro-](http://img.cochemist.com/ccimg/3500/3486-66-6_b.png)
![(2aR,3R,5S,5aR,6S,6aR,8R,9aR,10aS,10bR,10cR)-3-(acetyloxy)-8-furan-3-yl-6-(2-methoxy-2-oxoethyl)-2a,5a,6a,7-tetramethyl-2a,4,5,5a,6,6a,8,9,9a,10a,10b,10c-dodecahydro-2H,3H-cyclopenta[d]naphtho[2,3-b:1,8-b'c']difuran-5-yl (2E)-2-methylbut-2-enoate](http://img.cochemist.com/ccimg/1000/992-20-1.png)
![(2aR,3R,5S,5aR,6S,6aR,8R,9aR,10aS,10bR,10cR)-3-(acetyloxy)-8-furan-3-yl-6-(2-methoxy-2-oxoethyl)-2a,5a,6a,7-tetramethyl-2a,4,5,5a,6,6a,8,9,9a,10a,10b,10c-dodecahydro-2H,3H-cyclopenta[d]naphtho[2,3-b:1,8-b'c']difuran-5-yl (2E)-2-methylbut-2-enoate](http://img.cochemist.com/ccimg/1000/992-20-1_b.png)
![Card-20(22)-enolide,3-[(2,6-dideoxy-b-D-ribo-hexopyranosyl)oxy]-5,14-dihydroxy-19-oxo-,(3b,5b)-](http://img.cochemist.com/ccimg/700/630-64-8.png)
![Card-20(22)-enolide,3-[(2,6-dideoxy-b-D-ribo-hexopyranosyl)oxy]-5,14-dihydroxy-19-oxo-,(3b,5b)-](http://img.cochemist.com/ccimg/700/630-64-8_b.png)
![1,5-Cyclohexadiene-1-carboxylicacid, 3-[(1-carboxyethenyl)oxy]-4-hydroxy-, (3R,4R)-](http://img.cochemist.com/ccimg/700/617-12-9.png)
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![2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2R,3S,4R,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-chromen-4-one](http://img.cochemist.com/ccimg/500/482-35-9.png)
![2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2R,3S,4R,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-chromen-4-one](http://img.cochemist.com/ccimg/500/482-35-9_b.png)
![2H-1-Benzopyran-6-ol,3,4-dihydro-2,5,8-trimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-, (2R)-rel-](http://img.cochemist.com/ccimg/200/148-03-8.png)
![2H-1-Benzopyran-6-ol,3,4-dihydro-2,5,8-trimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-, (2R)-rel-](http://img.cochemist.com/ccimg/200/148-03-8_b.png)
![(12bS)-6,7,12b,13-tetrahydro-4H-[1,3]dioxolo[4,5-g][1,3]dioxolo[7,8]isoquino[3,2-a]isoquinoline](http://img.cochemist.com/ccimg/100/84-39-9.png)
![(12bS)-6,7,12b,13-tetrahydro-4H-[1,3]dioxolo[4,5-g][1,3]dioxolo[7,8]isoquino[3,2-a]isoquinoline](http://img.cochemist.com/ccimg/100/84-39-9_b.png)
![(S)-3-(hydroxymethyl)-5,5-dimethyl-4-[(O-beta-D-glucopyranosyl)methyl]cyclohex-2-enone](http://img.cochemist.com/ccimg/871600/871589-35-4.png)
![(S)-3-(hydroxymethyl)-5,5-dimethyl-4-[(O-beta-D-glucopyranosyl)methyl]cyclohex-2-enone](http://img.cochemist.com/ccimg/871600/871589-35-4_b.png)
![PROPANEDIOIC ACID, [(4-HYDROXYPHENYL)METHYL]-](http://img.cochemist.com/ccimg/90900/90844-16-9.png)
![PROPANEDIOIC ACID, [(4-HYDROXYPHENYL)METHYL]-](http://img.cochemist.com/ccimg/90900/90844-16-9_b.png)
![methyl (1S,4aS,5S,7aS)-5-hydroxy-7-(hydroxymethyl)-1-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate](http://img.cochemist.com/ccimg/52700/52613-28-2.png)
![methyl (1S,4aS,5S,7aS)-5-hydroxy-7-(hydroxymethyl)-1-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate](http://img.cochemist.com/ccimg/52700/52613-28-2_b.png)
![Cyclopenta[c]pyran-4-carboxylicacid, 1-(b-D-glucopyranosyloxy)-1,4a,5,6,7,7a-hexahydro-5,7-dihydroxy-7-methyl-,(1S,4aS,5R,7S,7aS)-](http://img.cochemist.com/ccimg/29900/29836-27-9.png)
![Cyclopenta[c]pyran-4-carboxylicacid, 1-(b-D-glucopyranosyloxy)-1,4a,5,6,7,7a-hexahydro-5,7-dihydroxy-7-methyl-,(1S,4aS,5R,7S,7aS)-](http://img.cochemist.com/ccimg/29900/29836-27-9_b.png)
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![(1s,3r,4r,5r)-3,4-bis[[(e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-1,5-dihydroxycyclohexane-1-carboxylic Acid](http://img.cochemist.com/ccimg/14600/14534-61-3.png)
![(1s,3r,4r,5r)-3,4-bis[[(e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-1,5-dihydroxycyclohexane-1-carboxylic Acid](http://img.cochemist.com/ccimg/14600/14534-61-3_b.png)
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![Cyclopenta[c]pyran-4-carboxylicacid, 1-(b-D-glucopyranosyloxy)-1,4a,5,7a-tetrahydro-5-hydroxy-7-(hydroxymethyl)-,(1S,4aS,5S,7aS)-](http://img.cochemist.com/ccimg/14300/14259-55-3_b.png)
![Didymin with HPLC [14259-47-3]](http://img.cochemist.com/ccimg/14300/14259-47-3.png)
![Didymin with HPLC [14259-47-3]](http://img.cochemist.com/ccimg/14300/14259-47-3_b.png)
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![(1S,3S,4S,5S)-1,3,4-trihydroxy-5-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}cyclohexanecarboxylic acid](http://img.cochemist.com/ccimg/1900/1899-29-2.png)
![(1S,3S,4S,5S)-1,3,4-trihydroxy-5-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}cyclohexanecarboxylic acid](http://img.cochemist.com/ccimg/1900/1899-29-2_b.png)
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![(E)-3-(4-hydroxyphenyl)-1-[2-hydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-phenyl]prop-2-en-1-one](http://img.cochemist.com/ccimg/59200/59122-93-9.png)
![(E)-3-(4-hydroxyphenyl)-1-[2-hydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-phenyl]prop-2-en-1-one](http://img.cochemist.com/ccimg/59200/59122-93-9_b.png)
![4H-1-Benzopyran-4-one,7-[[2-O-(6-deoxy-a-L-mannopyranosyl)-b-D-glucopyranosyl]oxy]-2-(3,4-dihydroxyphenyl)-2,3-dihydro-5-hydroxy-,(2S)-](http://img.cochemist.com/ccimg/13300/13241-32-2.png)
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![4H-1-Benzopyran-4-one,2-[4-(b-D-glucopyranosyloxy)phenyl]-2,3-dihydro-5,7-dihydroxy-,(2S)-](http://img.cochemist.com/ccimg/81300/81202-36-0_b.png)
![3-O-[beta-D-glucuronopyranosyl-(1->2)-beta-D-glucuronopyranosyl]liquiritic acid](http://img.cochemist.com/ccimg/118500/118441-85-3.png)
![3-O-[beta-D-glucuronopyranosyl-(1->2)-beta-D-glucuronopyranosyl]liquiritic acid](http://img.cochemist.com/ccimg/118500/118441-85-3_b.png)
![5,7-dihydroxy-2-(4-hydroxyphenyl)-6-[(2s,3r,4r,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-8-[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]chromen-4-one](http://img.cochemist.com/ccimg/52000/51938-32-0.png)
![5,7-dihydroxy-2-(4-hydroxyphenyl)-6-[(2s,3r,4r,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-8-[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]chromen-4-one](http://img.cochemist.com/ccimg/52000/51938-32-0_b.png)
![(e)-1-(2,4-dihydroxyphenyl)-3-[4-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]prop-2-en-1-one](http://img.cochemist.com/ccimg/5100/5041-81-6.png)
![(e)-1-(2,4-dihydroxyphenyl)-3-[4-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]prop-2-en-1-one](http://img.cochemist.com/ccimg/5100/5041-81-6_b.png)
![(2s)-7-hydroxy-2-[4-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-2,3-dihydrochromen-4-one](http://img.cochemist.com/ccimg/600/551-15-5.png)
![(2s)-7-hydroxy-2-[4-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-2,3-dihydrochromen-4-one](http://img.cochemist.com/ccimg/600/551-15-5_b.png)