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Gentiopicroside targets PAQR3 to activate the PI3K/AKT signaling pathway and ameliorate disordered glucose and lipid metabolism

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Acta Pharmaceutica Sinica B 2022年第6期12卷 2887-2904页

作者： Haiming Xiao Xiaohong Sun Zeyuan Lin Yan Yang Meng Zhang Zhanchi Xu Peiqing liu zhongqiu liu Heqing Huang Laboratory of Pharmacology&Toxicology School of Pharmaceutical SciencesSun Yat-sen UniversityGuangzhou 510006China School of Pharmaceutical Sciences Guangzhou University of Chinese MedicineGuangzhou 510006China National and Local United Engineering Lab of Druggability and New Drugs Evaluation School of Pharmaceutical SciencesSun Yat-sen UniversityGuangzhou 510006China

The obstruction of post-insulin receptor signaling is the main mechanism of insulin-resistant diabetes.Progestin and adipoQ receptor 3(PAQR3),a key regulator of inflammation and metabolism,can negatively regulate the PI3 K/AKT signaling pathway.Here,we report that gentiopicroside(GPS),the main bioactive secoiridoid glycoside of Gentiana manshurica Kitagawa,decreased lipid synthesis and increased glucose utilization in palmitic acid(PA) treated HepG2 cells.Additionally,GPS improved glycolipid metabolism in streptozotocin(STZ) treated high-fat diet(HFD)-induced diabetic mice.Our findings revealed that GPS promoted the activation of the PI3 K/AKT axis by facilitating DNA-binding protein 2(DDB2)-mediated PAQR3 ubiquitinated degradation.Moreover,results of surface plasmon resonance(SPR),microscale thermophoresis(MST) and thermal shift assay(TSA) indicated that GPS directly binds to PAQR3.Results of molecular docking and cellular thermal shift assay(CETSA) revealed that GPS directly bound to the amino acids of the PAQR3 NH2-terminus including Leu40,Asp42,Glu69,Tyr125 and Ser129,and spatially inhibited the interaction between PAQR3 and the PI3 K catalytic subunit(P110α) to restore the PI3 K/AKT signaling pathway.In summary,our study identified GPS,which inhibits PAQR3 expression and directly targets PAQR3 to restore insulin signaling pathway,as a potential drug candidate for the treatment of diabetes.

关键词： Gentiopicroside Insulin resistance PAQR3 PI3K/AKT DDB2 Ubiquitylation Glucose metabolism disorder Lipid metabolism disorder

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Fully synthetic Tn-based three-component cancer vaccine using covalently linked TLR4 ligand MPLA and iNKT cell agonist KRN-7000 as built-in adjuvant effectively protects mice from tumor development

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Acta Pharmaceutica Sinica B 2022年第12期12卷 4432-4445页

作者： Deying Yang Xiang Luo Qinghai Lian Lingqiang Gao Chengxin Wang Xiaoxiao Qi Rong Zhang zhongqiu liu Guochao Liao Joint Laboratory for Translational Cancer Research of Chinese Medicine of the Ministry of Education of the People's Republic of China International Institute for Translational Chinese MedicineGuangzhou University of Chinese MedicineGuangzhou 510006China Guangdong-Hong Kong-Macao Joint Lab on Chinese Medicine and Immune Disease Research Guangzhou 510120China

We present a new strategy for self-adjuvanting vaccine development that has different types of covalently-linked immunostimulants as the carrier molecule.Using Tn antigen as the model,a three-component vaccine(MPLA-Tn-KRN7000)containing the TLR4 ligand MPLA and the iNKT cell agonist KRN7000 was designed and synthesized.This expands fully synthetic self-adjuvanting vaccine studies that use a single carrier to one with two different types of carriers.The corresponding two-component conjugate vaccines Tn-MPLA,Tn-KRN7000 and Tn-CRM197 were also synthesized,as controls.The immunological evaluation found that MPLA-Tn-KRN7000 elicits robust Tn-specific and T cell-dependent immunity.The antibodies specifically recognized,bound to and exhibited complement-dependent cytotoxicity against Tn-positive cancer cells.In addition,MPLA-Tn-KRN7000 increased the survival rate and survival time of tumor-challenged mice,and surviving mice reject further tumor attacks without any additional treatment.Compared to the glycoprotein vaccine Tn-CRM197,the two-component conjugate vaccines,Tn-MPLA and Tn-KRN7000,and the physical mixture of Tn-MPLA and Tn-KRN7000,MPLA-Tn-KRN7000 showed the most effect at combating tumor cells both in vitro and in vivo.The comparison of immunological studies in wild-type and TLR4 knockout mice,along with the test of binding affinity to CD1d protein suggests that the covalently linked MPLA-KRN7000 immunostimulant induces a synergistic activation of TLR4 and iNKT cell that improves the immunogenicity of Tn.This work demonstrates that MPLA-Tn-KRN7000 has the potential to be a vaccine candidate and provides a new direction for fully synthetic vaccine design.

关键词： Cancer vaccine Tn antigen MPLA KRN7000 Immunotherapy

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IKKβ mediates homeostatic function in inflammation via competitively phosphorylating AMPK and IκBα

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Acta Pharmaceutica Sinica B 2022年第2期12卷 651-664,F0004页

作者： Juan liu Yuxin Zhuang Jianlin Wu Qiang Wu Meixian liu Yue Zhao zhongqiu liu Caiyan Wang Linlin Lu Yingjiao Meng Kawai Lei Xiaojuan Li Qibiao Wu Elaine Lai-Han Leung Zhengyang Guo Liang liu Ting Li State Key Laboratory of Quality Research in Chinese Medicine/Macao Institute for Applied Research in Medicine and Health Macao University of Science and TechnologyMacao SAR 999078China International Institute for Translational Chinese Medicine Guangzhou University of Chinese MedicineGuangzhou 510006China Guangdong Provincial Key Laboratory of New Drug Screening/Laboratory of Anti-inflammatory and Immunomodulatory Pharmacology School of Pharmaceutical SciencesSouthern Medical UniversityGuangzhou 510515China Guangdong-Hong Kong-Macao Joint Laboratory of Respiratory Infectious Disease Macao University of Science and TechnologyMacao SAR 999078China Joint Laboratory for Translational Cancer Research of Chinese Medicine of the Ministry of Education of the People’s Republic of China Macao University of Science and TechnologyMacao SAR 999078China

Inhibitor of nuclear factor kappa-B kinase subunit beta(IKKβ)is one of important kinases in inflammation to phosphorylate inhibitor of nuclear factor kappa-B(IκBα)and then activate nuclear factor kappa-B(NF-κB).Inhibition of IKKβhas been a therapeutic strategy for inflammatory and autoimmune diseases.Here we report that IKKβis constitutively activated in healthy donors and healthy Ikkβ^(C46A)(cysteine 46 mutated to alanine)knock-in mice although they possess intensive IKKβ-IκBα-NF-κB signaling activation.These indicate that IKKβactivation probably plays homeostatic role instead of causing inflammation.Compared to IkkβWTlittermates,lipopolysaccharides(LPS)could induce high mortality rate in Ikkβ^(C46A) mice which is correlated to breaking the homeostasis by intensively activating p-IκBα-NF-κB signaling and inhibiting phosphorylation of 5’adenosine monophosphate-activated protein kinase(p-AMPK)expression.We then demonstrated that IKKβkinase domain(KD)phosphorylates AMPKa1 via interacting with residues Thr183,Ser184,and Thr388,while IKKβhelix-loop-helix motifs is essential to phosphorylate IκBαaccording to the previous reports.Kinase assay further demonstrated that IKKβsimultaneously catalyzes phosphorylation of AMPK and IκBαto mediate homeostasis.Accordingly,activation of AMPK rather than inhibition of IKKβcould substantially rescue LPS-induced mortality in Ikkβ^(C46A) mice by rebuilding the homeostasis.We conclude that IKKβactivates AMPK to restrict inflammation and IKKβmediates homeostatic function in inflammation via competitively phosphorylating AMPK and IκBα.

关键词： IKKβ Homeostasis Kinase domain AMPK Inflammation IκBα Anti-inflammatory drug Phosphorylation

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Functional characterization of triterpene synthases in Cibotium barometz

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Synthetic and Systems Biotechnology 2023年第3期8卷 437-444页

作者： Zhongju Ji Baolian Fan Yidu Chen Jingyang Yue Jiabo Chen Rongrong Zhang Yi Tong zhongqiu liu Jincai Liang Lixin Duan Guangdong Provincial Key Laboratory of Translational Cancer Research of Chinese Medicines Joint International Research Laboratory of Translational Cancer Research of Chinese MedicinesInternational Institute for Translational Chinese MedicineSchool of Pharmaceutical SciencesGuangzhou University of Chinese MedicineGuangzhouChina

Cibotium barometz(Linn.)J.Sm.,a tree fern in the Dicksoniaceae family,is an economically important industrial exported plant in China and widely used in Traditional Chinese Medicine.C.barometz produces a range of bioactive triterpenes and their metabolites.However,the biosynthetic pathway of triterpenes in C.barometz remains unknown.To clarify the origin of diverse triterpenes in C.barometz,we conducted de novo transcriptome sequencing and analysis of C.barometz rhizomes and leaves to identify the candidate genes involved in C.barometz triterpene biosynthesis.Three C.barometz triterpene synthases(CbTSs)candidate genes were obtained.All of them were highly expressed in C.barometz rhizomes,consisting of the accumulation pattern of triterpenes in C.barometz.To characterize the function of these CbTSs,we constructed a squalene-and oxidosqualene-overproducing yeast chassis by overexpressing all the enzymes in the MVA pathway under the control of GAL-regulated promoter and disrupted the GAL80 gene in Saccharomyces cerevisiae simultaneously.Heterologous expressing CbTS1,CbTS2,and CbTS3 in engineering yeast strain produced cycloartenol,dammaradiene,and diploptene,respectively.Phylogenetic analysis revealed that CbTS1 belongs to oxidosqualene cyclase,while CbTS2 and CbTS3 belong to squalene cyclase.These results decipher enzymatic mechanisms underlying the origin of diverse triterpene in C.barometz.

关键词： 2,3-oxidosqualene cyclase Squalene cyclase Cibotium barometz Triterpene biosynthesis

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Tanshinone IIA Suppresses Non-Small Cell Lung Cancer Through Beclin-1-Mediated Autophagic Apoptosis

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Engineering 2022年第12期19卷 128-138页

作者： Shasha Bai Sainan Cui Wenhao Wen Elaine Lai-Han Leung Jing Bai Huiyuan Lin Yongfei Cui Lei Yang zhongqiu liu Yuan Zheng Rong Zhang School of Pharmaceutical Sciences Guangzhou University of Chinese MedicineGuangzhou 510006China State Key Laboratory of Quality Research in Chinese Medicine/Macao Institute for Applied Research in Medicine and Health Macao University of Science and TechnologyMacao 999078China Cardiothoracic Surgery Department The Second Clinical College of Guangzhou University of Chinese MedicineGuangdong Provincial Hospital of Chinese MedicineGuangzhou 510006China

It is necessary to develop a new strategy for treatment of lung cancer since it is the main cause of cancer death.Tanshinone IIA(Tan IIA),an active ingredient of a commonly used traditional Chinese herb Salvia miltiorrhiza,provides a new direction to develop a new strategy for the treatment.It has been found that Tan IIA could inhibit lung cancer in vitro and in vivo by inducing autophagic apoptosis.Tan IIA increased apoptotic cells and the expression of cleaved caspase 3 and cleaved caspase 9,decreased B-cell lymphoma-2(Bcl-2)/Bcl-2 associated X protein(Bax)ratio in human non-small cell lung cancer(NSCLC)cell lines,which was promoted by an autophagy activator Rapamycin,and weaken by autophagy inhibitor 3-methyladenine(3-MA).In addition,Tan IIA induced more autophagosomes,up-regulated light chain 3b(LC-3B)I and LC-3B II conversion and less sequestosome 1(SQSTM1/p62)expression,which cannot be weakened by the caspase 3 antagonist.Moreover,overexpression of LC-3B gene(LC3B)and downregulation of autophagic gene 5(ATG5)further confirmed that Tan IIA induced autophagic apoptosis in NSCLC cell lines.Beclin-1 gene(BECN1)overexpression and silence attenuated the effects of Tan IIA,suggesting autophagic apoptosis that Tan IIA induced was dependent on Beclin-1.Overall,our study demonstrated a new treatment mechanism of Tan IIA and suggested that Tan IIA is a potential new anti-cancer therapeutic option.

关键词： Tan IIA Autophagy Apoptosis Beclin-1

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miR-7/TGF-β2 axis sustains acidic tumor microenvironment-induced lung cancer metastasis

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Acta Pharmaceutica Sinica B 2022年第2期12卷 821-837页

作者： Tao Su Suchao Huang Yanmin Zhang Yajuan Guo Shuwei Zhang Jiaji Guan Mingjing Meng Linxin liu Caiyan Wang Dihua Yu Hiu-Yee Kwan Zhiying Huang Qiuju Huang Elaine Lai-Han Leung Ming Hu Ying Wang zhongqiu liu Linlin Lu Joint Laboratory for Translational Cancer Research of Chinese Medicine of the Ministry of Education of the People’s Republic of China Guangzhou University of Chinese MedicineGuangzhou 510006China Department of Molecular and Cellular Oncology the University of Texas MD Anderson Cancer CenterHoustonTX 77030USA School of Chinese Medicine Hong Kong Baptist UniversityHong Kong 999077China State Key Laboratory of Quality Research in Chinese Medicine/Macao Institute for Applied Research in Medicine and Health Macao University of Science and TechnologyMacao(SAR)999078China Department of Pharmacological and Pharmaceutical Sciences University of HoustonHoustonTX 77204USA

Acidosis,regardless of hypoxia involvement,is recognized as a chronic and harsh tumor microenvironment(TME)that educates malignant cells to thrive and metastasize.Although overwhelming evidence supports an acidic environment as a driver or ubiquitous hallmark of cancer progression,the unrevealed core mechanisms underlying the direct effect of acidification on tumorigenesis have hindered the discovery of novel therapeutic targets and clinical therapy.Here,chemical-induced and transgenic mouse models for colon,liver and lung cancer were established,respectively.miR-7 and TGF-β2 expressions were examined in clinical tissues(n=184).RNA-seq,miRNA-seq,proteomics,biosynthesis analyses and functional studies were performed to validate the mechanisms involved in the acidic TME-induced lung cancer metastasis.Our data show that lung cancer is sensitive to the increased acidification of TME,and acidic TME-induced lung cancer metastasis via inhibition of miR-7-5 p.TGF-β2 is a direct target of miR-7-5 p.The reduced expression of miR-7-5 p subsequently increases the expression of TGF-β2 which enhances the metastatic potential of the lung cancer.Indeed,overexpression of miR-7-5 p reduces the acidic p H-enhanced lung cancer metastasis.Furthermore,the human lung tumor samples also show a reduced miR-7-5 p expression but an elevated level of activated TGF-β2;the expressions of both miR-7-5 p and TGF-β2 are correlated with patients’survival.We are the first to identify the role of the miR-7/TGF-β2 axis in acidic p H-enhanced lung cancer metastasis.Our study not only delineates how acidification directly affects tumorigenesis,but also suggests miR-7 is a novel reliable biomarker for acidic TME and a novel therapeutic target for non-small cell lung cancer(NSCLC)treatment.Our study opens an avenue to explore the p H-sensitive subcellular components as novel therapeutic targets for cancer treatment.

关键词： Acidic tumor microenvironment miR-7-5p TGF-β2 Metastasis Lung cancer pH Invasion

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Exploring the catalytic function and active sites of a novel C-glycosyltransferase from Anemarrhena asphodeloides

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Synthetic and Systems Biotechnology 2022年第1期7卷 621-630页

作者： Jia Huang Yaru She Jingyang Yue Yidu Chen Yu Li Jing Li Yonger Hu Deying Yang Jiabo Chen Lu Yang zhongqiu liu Ruibo Wu Pengfei Jin Lixin Duan Joint Laboratory for Translational Cancer Research of Chinese Medicine of the Ministry of Education of the People’s Republic of China International Institute for Translational Chinese MedicineGuangzhou University of Chinese MedicineGuangzhou510006PR China Guangdong Provincial Key Laboratory of New Drug Design and Evaluation School of Pharmaceutical SciencesSun Yat-sen UniversityGuangzhou510006PR China Department of Pharmacy Beijing HospitalNational Center of GerontologyInstitute of Geriatric MedicineChinese Academy of Medical SciencesBeijing Key Laboratory of Assessment of Clinical Drugs Risk and Individual Application(Beijing Hospital)Beijing100730PR China

Anemarrhena asphodeloides is an immensely popular medicinal herb in China,which contains an abundant of mangiferin.As an important bioactive xanthone C-glycoside,mangiferin possesses a variety of pharmacological activities and is derived from the cyclization reaction of a benzophenone C-glycoside(maclurin).Biosyntheti-cally,C-glycosyltransferases are critical for the formation of benzophenone C-glycosides.However,the benzo-phenone C-glycosyltransferases from Anemarrhena asphodeloides have not been discovered.Herein,a promiscuous C-glycosyltransferase(AaCGT)was identified from Anemarrhena asphodeloides.It was able to catalyze efficiently mono-C-glycosylation of benzophenone,together with di-C-glycosylation of dihydrochalcone.It also exhibited the weak O-glycosylation or potent S-glycosylation capacities toward 12 other types of flavonoid scaffolds and a simple aromatic compound with–SH group.Homology modeling and mutagenesis experiments revealed that the glycosylation reaction of AaCGT was initiated by the conserved residue H23 as the catalytic base.Three critical residues H356,W359 and D380 were involved in the recognition of sugar donor through hydrogen-bonding interactions.In particular,the double mutant of F94W/L378M led to an unexpected enzy-matic conversion of mono-C-to di-C-glycosylation.This study highlights the important value of AaCGT as a potential biocatalyst for efficiently synthesizing high-value C-glycosides.

关键词： C-glycosides Anemarrhena asphodeloides C-glycosyltransferases Benzophenone Active sites

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Deciphering the pharmacological mechanism of Guan-Jie-Kang in treating rat adjuvant-induced arthritis using omics analysis

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Frontiers of Medicine 2019年第5期13卷 564-574页

作者： Hudan Pan Yanfang Zheng zhongqiu liu Zhongwen Yuan Rutong Ren Hua Zhou Ying Xie Liang liu tate Key Laboratory of Quality Research in Chinese Medicine/Macao Institute for Applied Research in Medicine and Health Macao University of Science and TechnologyMacaoChina Fujian University of Traditional Chinese Medicine Fuzhou 350122China International Institute for Translational Research of Traditional Chinese Medicine of Guangzhou University of Chinese Medicine Guangzhou 510006China

Traditional Chinese medicine (TCM) formulas have attracted increasing attention worldwide in the past few years for treating complex disease including rheumatoid arthritis. However, their mechanisms are complex and remain unclear. Guan-Jie-Kang (GJK), a prescription modified from “Wu Tou Decoction,” was found to significantly relieve arthritis symptoms in rats with adjuvant-induced arthritis after 30-day treatment, especially in the 24 g/kg/day group. By analyzing 1749 targets related to 358 compounds in the five herbs of GJK, we identified the possible anti-arthritis pathways of GJK, including the calcium signaling and metabolic pathways. Bone damage levels were assessed by micro-computed tomography, and greater bone protective effect was observed with GJK treatment than with methotrexate. Receptor activator of nuclear factor kB ligand (RANKL)-RANK signaling, which is related to calcium signaling, was significantly regulated by GJK. Moreover, a target metabolomics assay of serum was conducted;17 metabolic biomarkers showed significant correlations with treatment. An integrated pathway analysis revealed that pyruvate metabolism, purine metabolism, and glycolysis metabolism were significantly associated with the effects of GJK in arthritis treatment. Thus, this study establishes a new omics analytical method integrated with bioinformatics analysis for elucidating the multi-pathway mechanisms of TCM.

关键词： rheumatoid arthritis traditional Chinese medicine pharmacological mechanism metabolism adjuvant-induced arthritis omics analysis

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Isolation and purification of carbazole contained in anthracene slag by extraction combined with medium pressure liquid chromatography

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Chinese Journal of Chemical Engineering 2019年第12期27卷 2925-2929页

作者： Zhihao Ma XianyongWei Mingyao Zhou Guanghui liu Fangjing liu zhongqiu liu Xinyue Yu Zhimin Zong Key Laboratory of Coal Processing and Efficient Utilization Ministry of EducationChina University of Mining&TechnologyXuzhou 221116China State Key Laboratory of High-efficiency Coal Utilization and Green Chemical Engineering Ningxia UniversityYinchuan 750021China

Ultrasonic-assisted extraction(UAE)combined with medium pressure liquid chromatography(MPLC)was designed for carbazole separation from anthracene slag(AS).The effects of liquid/solid ratio,temperature,and extraction times on carbazole separation were investigated.When using CC14 and ethyl acetate as extraction solvents and combining with MPLC,carbazole recovery and purity are 75.1%and 95.4%,respectively.The mechanism for carbazole separation were presumed by examining intermolecular interactions such as N-H…π,π-π,and C-Cl…πinteractions.These results demonstrate that UAE/MPLC has a considerable potential as a green and promising strategy for separating and purifying carbazole and other chemicals from AS.

关键词： Anthracene slag Ultrasonic-assisted extraction Medium pressure liquid chromatography Intermolecular interactions

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Non-covalent glycosylated gold nanoparticles/peptides nanovaccine as potential cancer vaccines

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Chinese Chemical Letters 2020年第5期31卷 1162-1164页

作者： Liming Zeng Zonglang Liao Wenwei Li Qijuan Yuan Peng Wu Zhipeng Gu zhongqiu liu Guochao Liao Joint Laboratory for Translational Cancer Research of Chinese Medicine of the Ministry of Education of the People's Republic of China International Institute for Translational Chinese MedicineGuangzhou University of Chinese MedicineGuangzhou 510006China School of Biomedical Engineering Sun Yat-sen UniversityGuangzhou 510006.China

Herein,we firstly developed a non-covalent glycosylated gold nanoparticles/peptides nanovaccine which is assembled byβ-cyclodextrin(β-CD)based host-guest recognitions.This nanovaccine can generate significant titers of antibodies and improve the therapeutic effect against melanoma,suggesting the immunogenicity of peptide antigens can be improved by loading with this carrier.The novel vaccine carrier provides a platform for the transport of various antigens especially T cell-independent antigens.

关键词： Non-covalent Glycosylation Nanoparticles/peptides nanovaccine β-Cyclodextrin Host-guest recognitions Cancer vaccines

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