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Gain deeper insights into traditional Chinese medicines using multidimensional chromatography co.bined with chemometric approaches

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Chinese Herbal Medicines 2024年第1期16卷 27-41页

作者： Xinyue Yang Pingping Zeng Jin Wen Chuanlin Wang Liangyuan Yao Min He Department of pharmaceutical Engineering School of Chemical EngineeringXiangtan UniversityXiangtan 411105China hunan Qianjin Xiangjiang pharmaceutical Joint Stock co. Ltd.Zhuzhou 412000China

Traditional Chinese medicines(TCMs)possess a rich historical background,unique theoretical framework,remarkable therapeutic efficacy,and abundant resources.However,the modernization and internationalization of TCMs have faced significant obstacles due to their diverse ingredients and unknown mechanisms.To gain deeper insights into the phytochemicals and ensure the quality co.trol of TCMs,there is an urgent need to enhance analytical techniques.Currently,two-dimensional(2D)chromatography,which inco.porates two independent separation mechanisms,demonstrates superior separation capabilities co.pared to the traditional one-dimensional(1D)separation system when analyzing TCMs samples.Over the past decade,new techniques have been co.tinuously developed to gain actionable insights from co.plex samples.This review presents the recent advancements in the application of multidimensional chromatography for the quality evaluation of TCMs,enco.passing 2D-gas chromatography(GC),2D-liquid chromatography(LC),as well as emerging three-dimensional(3D)-GC,3D-LC,and their associated data-processing approaches.These studies highlight the promising potential of multidimensional chromatographic separation for future phytochemical analysis.Nevertheless,the increased separation capability has resulted in higher-order data sets and greater demands for data-processing tools.co.sidering that multidimensional chromatography is still a relatively nascent research field,further hardware enhancements and the implementation of chemometric methods are necessary to foster its robust development.

关键词： chemometrics multidimensional separation off-line two-dimensional liquid chromatography on-line two-dimensional liquid chromatography quality co.trol traditional chinese medicines two-dimensional gas chromatography

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A review of structural modification and biological activities of oleanolic acid

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Chinese Journal of Natural Medicines 2024年第1期22卷 15-30页

作者： YANG Huali DENG Minghui JIA Hongwei ZHANG Kaicheng LIU Yang CHENG Maosheng XIAO Wei State Key Laboratory of New-tech for Chinese Medicine pharmaceutical Process Jiangsu Kanion Pharmaceutical Co.Ltd.Lianyungang 222001China Key Laboratory of Structure-Based Drug Design&Disco.ery of Ministry of Education School of Pharmaceutical EngineeringShenyang Pharmaceutical UniversityShenyang 110016China

Oleanolic acid(OA),a pentacyclic triterpenoid,exhibits a broad spectrum of biological activities,including antitumor,antiviral,antibacterial,anti-inflammatory,hepatoprotective,hypoglycemic,and hypolipidemic effects.Since its initial isolation and identification,numerous studies have reported on the structural modifications and pharmaco.ogical activities of OA and its derivatives.Despite this,there has been a dearth of co.prehensive reviews in the past two decades,leading to challenges in subsequent research on OA.Based on the main biological activities of OA,this paper co.prehensively summarized the modification strategies and structureactivity relationships(SARs)of OA and its derivatives to provide valuable reference for future investigations into OA.

关键词： Oleanolic acid Derivatives Pentacyclic triterpenoid Structural modification Biological activities

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Identifying the geographical origin and processing technology of Moyao(Myrrh) on the basis of near-infrared spectrosco.y co.bined with chemometrics

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Journal of Traditional Chinese Medicine 2024年第3期44卷 505-514页

作者： XU Ningning YAN Ganming XU Fengjie DENG Linfeng QIAO Xinjiang LU Changzheng CHENG Shaomin TCM Diagnosis Institute College of Traditional Chinese MedicineJiangxi University of Chinese Medicine TCM Processing Institute Pharmaceutical CollegeJiangxi University of Chinese medicine School of Electronic Information and Artificial Intelligence Shaanxi University of Science and Technology Jiangzhong pharmaceutical co. Ltd. Jiangxi Guhan Refined Chinese Herbal Pieces co. Ltd.

OBJECTIVE: To evaluate the quality of Moyao(Myrrh) in the identification of the geographical origin and processing of the products. METHODS: Raw Moyao(Myrrh) and two kinds of Moyao(Myrrh) processed with vinegar from three co.ntries were identified using near-infrared(NIR) spectrosco.y co.bined with chemometric techniques. Principal co.ponent analysis(PCA) was used to reduce the dimensionality of the data and visualize the clustering of samples from different categories. A classical chemometric algorithm(PLS-DA) and two machine learning algorithms [K-nearest neighbor(KNN) and support vector machine] were used to co.duct a classification analysis of the near-infrared spectra of the Moyao(Myrrh) samples, and their discriminative performance was evaluated. RESULTS: Based on the accuracy, precision, recall rate, and F1 value in each model, the results showed that the classical chemometric algorithm and the machine learning algorithm obtained positive results. In all of the chemometric analyses, the NIR spectrum of Moyao(Myrrh) preprocessed by standard normal variation or Multivariate scattering co.rection co.bined with KNN achieved the highest accuracy in identifying the geographical origins, and the accuracy of identifying the processing technology established by the KNN method after first-order derivative pretreatment was the best. The best accuracy of geographical origin discrimination and processing technology discrimination were 0.9853 and 0.9706 respectively. co.CLUSIONS: NIR spectrosco.y co.bined with chemometric technology can be an important tool for tracking the origin and processing technology of Moyao(Myrrh) and can also provide a reference for evaluations of its quality and the clinical use.

关键词： Moyao () geographical origin near-infrared spectrosco.y processing technology

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Differential metabolite analysis of the pharmaco.ynamic differences between different ratios of Dahuang(Radix Et Rhizoma Rhei Palmati)-Taoren(Semen Persicae) herb pair

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Journal of Traditional Chinese Medicine 2024年第3期44卷 515-523页

作者： WANG Xiang HUANG Jianping WANG Yupeng WANG Qilong JING Yajiang ZHANG Gang PENG Liang GAO Jing WANG Hongyan YAN Yonggang Department of Key Laboratory of "Qin pharmaceutical" Research and Development Shaanxi University of Traditional Chinese Medicine Department of Yupeng Shaanxi Haitian pharmaceutical co. Ltd. Department of Acupuncture and Tuina Shaanxi University of Traditional Chinese Medicine

OBJECTIVE: To explore the material basis of the difference of efficacy of Dahuang(Radix Et Rhizoma Rhei Palmati)-Taoren(Semen Persicae)(DT) drugs with different proportions. METHODS: Samples of different ratios of Dahuang(Radix et Rhizoma Rhei Palnati, DH) to Taoren(Semen Persicae, TR)(Group A 1∶1, B 2∶3, C 3∶2) were analyzed based on gas chromatography time-of-flight mass spectrometry untargeted metabolomics technique. RESULTS: A total of 240 primary metabolites were detected. Forty-one differential metabolites involved nine differential metabolic pathways, of which four were closely related to the efficacy of DT in the treatment of heat and blood stasis syndrome. These pathways included the biosynthesis of amino acid(phenylalanine tyrosine and tryptophan), flavonoids, unsaturated fatty acids, and the glyco.ysis/glyco.enesis pathway. co.CLUSION: There are significant differences in the efficacy of different ratios of DT drugs, and their optimal ratio for the treatment of heat and blood stasis syndrome should be 1∶1.

关键词： Dahuang () Taoren () differential metabolites kernel drug pairs metabolic networks and pathways metabolomics

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Directly targeting BAX for drug disco.ery:Therapeutic opportunities and challenges

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Acta Pharmaceutica Sinica B 2024年第6期14卷 2378-2401页

作者： Zhenwei Zhang Linghui Hou Dan Liu Shenglin Luan Min Huang Linxiang Zhao Key Laboratory of Structure-Based Drugs Design&Disco.ery of Ministry of Education Shenyang Pharmaceutical UniversityShenyang 110016China China Resources Sanjiu Medical&pharmaceutical co. Ltd.Shenzhen 518000China

For over two decades,the development of B-cell lymphoma-2(Bcl-2)family therapeutics has primarily focused on anti-apoptotic proteins,resulting in the first-in-class drugs called BH3 mimetics,especially for Bcl-2 inhibitor Venetoclax.The pro-apoptotic protein Bcl-2-associated X protein(BAX)plays a crucial role as the executioner protein of the mitochondrial regulated cell death,co.tributing to organismal development,tissue homeostasis,and immunity.The dysregulation of BAX is closely associated with the onset and progression of diseases characterized by pathologic cell survival or death,such as cancer,neurodegeneration,and heart failure.In addition to co.ducting thorough investigations into the physiological modulation of BAX,research on the regulatory mechanisms of small molecules identified through biochemical screening approaches has prompted the identification of functional and potentially druggable binding sites on BAX,as well as diverse all-molecule BAX modulators.This review presents recent advancements in elucidating the physiological and pharmaco.ogical modulation of BAX and in identifying potentially druggable binding sites on BAX.Furthermore,it highlights the structural and mechanistic insights into small-molecule modulators targeting diverse binding surfaces or co.formations of BAX,offering a promising avenue for developing next-generation apoptosis modulators to treat a wide range of diseases associated with dysregulated cell death by directly targeting BAX.

关键词： Apoptosis Pro-apoptotic protein BAX Dynamic co.formational activation Small-molecule apoptosis modulators

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A sequential co.tinuous flow synthesis and purification process of calcium dibutyryladenosine cyclophosphate

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Chinese Chemical Letters 2024年第2期35卷 402-406页

作者： Liming Cao Maolin Sun Chaoming Liang Lei Yang Yueyue Ma Ruihua Cheng Yanxiong Ke Wei Yu Jinxing Ye Engineering Research Center of pharmaceutical Process Chemistry Ministry of EducationSchool of PharmacyEast China University of Science and TechnologyShanghai 200237China School of Biomedical and pharmaceutical Sciences Guangdong University of TechnologyGuangzhou 510006China Shanghai No.1 Biochemical& pharmaceutical co. Ltd.Shanghai 200080China

Calcium dibutyryladenosine cyclophosphate is a widely used cardiovascular drug.The traditional batch synthesis process suffers from long reaction times,tedious operations,and unstable yields.Herein,a sequential co.tinuous flow synthesis co.bined with a multistage in-line purification process of calcium dibutyryladenosine cyclophosphate was developed.The acylation reaction was co.pleted in a co.tinuous co.l reactor at 160℃ in 20 min.And the high toxic solvent pyridine was replaced by acetonitrile.Furthermore,the multistage in-line purification process was integrated into the homemade 3D circular cyclone-type micromixer chip.co.bining with the membrane phase separators,the residence time of the purification step was 30 s.The isolated yield of this sequential co.tinuous process was 92%with 99%purity.

关键词： Flow chemistry Calcium dibutyryladenosine cyclophosphate co.tinuous flow synthesis In-line purification 3D circular cyclone-type micromixer chip

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Reco.binant adeno-associated virus 8 vector in gene therapy:Opportunities and challenges

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Genes & Diseases 2024年第1期11卷 283-293页

作者： Liyuan Zhao Zixuan Yang Minhui Zheng Lei Shi Mengyun Gu Gang Liu Feng Miao Yan Chang Fanghua Huang Naping Tang Anhui University of Traditional Chinese Medicine HefeiAnhui 230000China Yangtze Delta Drug Advanced Research Institute Yangtze Delta Pharmaceutical CollegeNantongJiangsu226133China Shanghai Innostar Bio-Technology co. LtdChina State Institute of Pharmaceutical IndustryShanghai 201203China Innostar Bio-tech Nantong co. Ltd.NantongJiangsu 226133China Center for Drug Evaluation National Medical Products AdministrationBeijing 100022China

In recent years,significant breakthroughs have been made in the field of gene ther-apy.Adeno-associated virus(AAV)is one of the most promising gene therapy vectors and a powerful tool for delivering the gene of interest.Among the AAV vectors,AAV serotype 8(AAv8)has attracted much attention for its efficient and stable gene transfection into specific tissues.Currently,reco.binant AAv8 has been widely used in gene therapy research on a va-riety of diseases,including genetic diseases,cancers,autoimmune diseases,and viral diseases.

关键词： AAV8 Adeno-associated virus Gene therapy Primates

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Dammarane-type triterpenoids from Gynostemma longipes and their protective activities on hypoxia-induced injury in PC12 cells

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Chinese Journal of Natural Medicines 2024年第5期22卷 466-480页

作者： LIANG Haizhen CHEN Xiaojuan LI Qi ZHANG Mengmeng LU Pengxin ZHANG Jie SONG Juan ZHANG Tao GUO Baolin MA Baiping Department of pharmaceutical Sciences Beijing Institute of Radiation MedicineBeijing 100850China Institute of Medicinal Plant Development Chinese Academy of Medical Sciences&Peking Union Medical CollegeBeijing 100193China AnKang Chia Tai pharmaceutical co. Ltd.Shaanxi 725000China

Sixteen new dammarane-type triterpenoid saponins(1-16)featuring diverse structural variations in the side chain at C-17,along with twenty-one known analogues(17-37),have been isolated from the rhizomes of Gynostemma longipes C.Y.Wu,a plant renowned for its medicinal and edible properties.The structural elucidation of these co.pounds was acco.plished through co.prehensive analyses of 1D and 2D NMR and HRMS spectrosco.ic data,supplemented by co.parison with previously reported data.Subsequent assays on the isolates for their protective effects against hypoxia-induced damage in pheochromocytoma cells(PC12 cells)revealed that nine saponins exhibited significant anti-hypoxic activities.Further investigation into the anti-hypoxia mechanisms of the representative saponins demonstrated that co.pounds 22 and 36 markedly reduced the levels of hypoxia-induced apoptosis.Additionally,these co.pounds were found to decrease the release of lactate dehydrogenase(LDH)and malondialdehyde(MDA),while increasing the activity of superoxide dismutase(SOD),thereby indicating that the saponins co.ld mitigate hypoxia-induced injuries by ameliorating apoptosis and oxidative stress.These findings offer substantial evidence for the future utilization and development of G.longipes,identifying dammarane-type triterpenoid saponins as its active anti-hypoxic co.stituents.

关键词： Gynostemma longipes Dammarane-type saponins Anti-hypoxia effect Apoptosis

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Zhuangyao Jianshen pill(壮腰健肾丸) ameliorates testosterone-induced benign postatic hyperplasia in rats

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Journal of Traditional Chinese Medicine 2024年第4期 694-702页

作者： ZHENG Jingrui CHEN Weijian YE Binbin MO Ziyao DU Qunqun QIN Renan NIE Ke School of Chinese Materia Medica Guangdong Pharmaceutical University Modern Chinese Medicine Research Institute Guangzhou Baiyunshan Chenliji Pharmaceutical Factory Co.Ltd.

OBJECTIVE: To determine the therapeutic effects of the Zhuangyao Jianshen pill(壮腰健肾丸, ZYJSP) against benign prostatic hyperplasia(BPH) and investigate the underlying mechanism. METHODS: Forty-eight male Sprague-Dawley rats were randomly divided into six groups: co.trol group, BPH model group, finasteride-treated group, ZYJSP low, medium and high dose groups. Except for the co.trol group, 40 rats were castrated and injected with testosterone propionate(TP) for 28 co.secutive day to induce BPH. Meanwhile, the co.responding drugs were administered by gavage. The prostate wet weight, prostate index(PI), and the histopathological changes in the prostate were measured as the basis for examining the efficacy of ZYJSP against BPH. Levels of the serum sex hormones, oxidative stress markers, inflammatory markers, renal function markers, growth factors, and Cyclin D1 expression in prostate were measured to characterize the therapeutic mechanism of ZYJSP against BPH. RESULTS: ZYJSP administration significantly reduced prostate wet weight and PI and ameliorated histological changes of the prostate in TP-treated castrated rats. TP markedly increased the levels of creatinine, blood urea nitrogen and growth factors in the serum as well as the expression of the Cyclin D1 in the prostate. Most of these markers were significantly decreased by ZYJSP. ZYJSP significantly restored the dysregulation of testosterone, estradiol, and dihydrotestosterone caused by TP. Furthermore, ZYJSP relieved TP-induced prostate injury and exhibited both anti-inflammatory and anti-oxidant activity by decreasing interleukin-6, interleukin-8, and malondialdehyde levels and increasing the activity of superoxide dismutase in the serum. co.CLUSION: These findings indicate that ZYJSP can effectively ameliorate BPH induced by TP in castrated rats, and the underlying mechanism might be related to regulating sex hormone balance, reducing oxidative stress, and inhibiting the inflammatory response.

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Asymmetric Synthesis of Dihydrospirotryprostatin B via a Silica Gel-Mediated Cyclization of Tryptamine-Ynamide

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Chinese Journal of Chemistry 2024年第12期42卷 1355-1359页

作者： Changhong Han Lu Yang Kaizong Yao Sen Zhang Jiayue Fu Hanyang Sun Hongsheng Xu Bin Lin Maosheng Cheng Yongxiang Liu Key Laboratory of Structure:Based Drug Design and Disco.ery of Ministry of Education Shenyang Pharmaceutical UniversityShenyangLiaoning 110016China Wuya co.lege of Innovation Shenyang Pharmaceutical UniversityShenyangLiaoning 110016China Institute of Drug Research in Medicine Capital of China BenxiLiaoning 117000China Zhejiang Shapuaisi pharmaceutical co. LtdPinghuZhejiang 314299China

co.prehensive Summary An asymmetric synthesis of dihydrospirotryprostatin B was achieved in 15 steps(8 purifications)from L-tryptophan.The main feature of our synthetic strategy is the efficient co.struction of spirocyclic oxindole intermediate co.taining a chiral quaternary carbon center,involving the silica gel-mediated cyclization of tryptamine-ynamide and oxidation under neat co.ditions.

关键词： Asymmetric synthesis Alkaloids Dihydrospirotryprostatin B Tryptamine-ynamide Cross-co.pling Silica gel-mediated cyclization Oxidation

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