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Isolation of chemical compositions as dietary antioxidant supplements and neuroprotectants from Chaga mushroom (Inonotus obliquus)

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Food Bioscience 2022年第3期47卷 211-220页

作者： Ye Chang Ming Bai Xiao-Bian Xue Chun-Xin Zou Xiao-Xiao Huang Shao-Jiang Song key laboratory of Computational Chemistry-Based Natural Antitumor drug Research & development Liaoning ProvinceChina Engineering Research Center of Natural Medicine active Molecule Research & development Liaoning ProvinceChina key laboratory of Natural Bioactive Compounds Discovery & Modification ShenyangChina School of Traditional Chinese Materia Medica Shenyang Pharmaceutical UniversityShenyangLiaoning110016China

Excessive free radicals can cause oxidative stress (OS),which lead to neurodegenerative diseases (ND) are harmful to the human ***,it is necessary to explore dietary antioxidants and neuroprotectants from nutrient *** mushroom (Inonotus obliquus ) has been used as an important functional food in many countries for *** present study was carried out to discover active compounds from *** and investigate the in vitro antioxidant activity and neuroprotective *** natural products including two new isocoumarins (1 –2 ),a new 8-O -4′-neolignan (3 ),a new cyclic diarylheptanoid (4 ),and twelve known compounds (5 –16 ) were separated from *** .Their structures were elucidated by extensive spectroscopic analyses of high resolution electrospray mass spectrometry (HRESIMS),ultra violet (UV),and nuclear magnetic resonance (NMR).Among them,compounds 1 and 2 revealed remarkable antioxidant activities through the comprehensive analysis of DPPH,ABTS,and ferric reducing antioxidant power (FRAP) ***,compound 1 demonstrated significant neuroprotective activity by increasing SH-SY5Y cells viability and preventing mitochondrial *** from that,electronic analyses were performed using the highest occupied molecular orbital (HOMO),and the lowest unoccupied molecular orbital (LUMO) to analyze compound 1 .These results indicated that compound 1 had a significant implication for the search of natural raw material to prevent OS and nerve damage in the field of functional foods,and the isocoumarin fragment as well as an oxygenated cis double-bond might be the active sites to play prominent parts in antioxidant and neuroprotective activities of compound 1 .

关键词： Inonotus obliquus Chaga mushroom Functional food Neuroprotective activity Antioxidant activity

Peptide nanotube loaded with a STING agonist,c-di-GMP,enhance cancer immunotherapy against melanoma

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Nano Research 2023年第4期16卷 5206-5215页

作者： Ziyuan Zhang Juan Liu Min Xiao Quanfeng Zhang Zhonghua Liu Meiyan Liu Peng Zhang Youlin Zeng key laboratory of the Assembly and Application of Organic Functional molecules of Hunan Province Hunan Normal UniversityChangsha 410081China laboratory of Chemical Biology and Traditional Chinese Medicine Research(Ministry of Education of China) Hunan Normal UniversityChangsha 410081China The National&Local Joint Engineering laboratory of Animal Peptide drug development College of Life SciencesHunan Normal UniversityChangsha 410081China

The activation of the stimulating factor of the interferon gene(STING)pathway can enhance the immune response within the *** diguanylate monophosphate(c-di-GMP)is a negatively charged,hydrophilic STING agonist,however,its effectiveness is limited due to the poor membrane permeability and low ***,we introduced KL-7 peptide derived from Aβamyloid fibrils that can self-assemble to form nanotubes to load and deliver c-di-GMP,which significantly enhanced c-di-GMP’s effectiveness and then exhibited a robust“in situ immunity”to kill melanoma ***-7 peptide nanotube,also called PNT,was loaded with negatively charged c-di-GMP via electrostatic interaction,which prepared a nanocomposite named *** of RAW 264.7 cells(leukemia cells in mouse macrophage)with c-di-GMP-PNT markedly stimulated the secretion of IL-6 and INF-βalong with phospho-STING(Ser365)protein expression,indicating the activation of the STING *** the unilateral flank B16-F10(murine melanoma cells)tumor-bearing mouse model,compared to PNT and cdi-GMP,c-di-GMP-PNT can promote the expression of INF-β,TNF-α,IL-6,and IL-1β.At the same time,up-regulated CD4 and CD8 active T cells kill tumors and enhance the immune response in tumor tissues,resulting in significant inhibition of tumor growth in tumor-bearing *** importantly,in a bilateral flank B16-F10 tumor model,both primary and distant tumor growth can also be significantly inhibited by ***,c-di-GMP-PNT demonstrated no obvious biological toxicity on the main organs(heart,liver,spleen,lung,and kidney)and biochemical indexes of *** summary,our study provides a strategy to overcome the barriers of free c-di-GMP in the tumor microenvironment and c-di-GMP-PNT may be an attractive nanomaterial for anti-tumor immunity.

关键词： cyclic diguanylate monophosphate stimulating factor of the interferon gene(STING) peptide nanotubes in situ immunity tumor immunotherapy

Synthesis of 7-Triazole-substituted Camptothecin via Click Chemistry and Evaluation of in vitro Antitumor Activity

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Chinese Journal of Chemistry 2014年第2期32卷 157-162页

作者： Lei Wang Wei Yuan Jie Zhang Linjiang Tong Yu Luo Yi Chen Wei Lu Qingqing Huang Institute of drug Discovery and development Shanghai Engineering Research Center of Molecular Therapeutics and New Drug DevelopmentEast China Normal UniversityShanghai 200062China State key laboratory of drug Research Shanghai Institute of Materia MedicaSIBSChinese Academy of SciencesShanghai 201203China

Camptothecin(CPT)is a natural topoisomerase I inhibitor with powerful antineoplastic activity against colorectal,breast,lung and ovarian *** discover more potent antitumor agents,a series of new CPT derivatives were synthesized utilizing click *** compounds were assessed for cytotoxicity against A549,HCT-116,HT-29,LoVo,MDA-MB-231 cell lines,and some compounds exhibited good in vitro ***,all compounds kept or enhanced Topo I inhibition.

关键词： camptothecin 7-triazole-substituted camptothecin click chemistry antitumor

Rapid discovery of two unprecedented meroterpenoids from Daphne altaica *** molecular networking integrated with MolNetEnhancer and Network Annotation Propagation

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Chinese Chemical Letters 2024年第8期35卷 294-298页

作者： Wei-Yu Zhou Zi-Han Xi Ning-Ning Du Li Ye Ming-Hao Jiang Jin-Le Hao Bin Lin Guo-Dong Yao Xiao-Xiao Huang Shao-Jiang Song key laboratory of Computational Chemistry-Based Natural Antitumor drug Research&development Liaoning ProvinceEngineering Research Center of Natural Medicine Active Molecule Research&DevelopmentLiaoning ProvinceKey Laboratory of Natural Bioactive Compounds Discovery&ModificationShenyangSchool of Traditional Chinese Materia Medic1Shenyang Pharmaceutical UniversityShenyang 110016China key laboratory of Structure-Based drug Design and Discovery of Ministry of Education Shenyang Pharmaceutical UniversityShenyang 110016China Wuya College of Innovation Shenyang Pharmaceutical UniversityShenyang 110016China

Under the guidance of the approach which integrates molecular networking,MolNetEnhancer and Net-work Annotation Propagation(NAP),daphnaltaicanoids A and B(1 and 2)with unprecedented 9-oxa-tetracyclo[6.***.1.0^(2,6).0^(8,13)]pentadecane and tetracyclo[5.***.0.1^(2,5).2^(4,11)]tridecane central frameworks were iso-lated from Daphne altaica Pall.,representing two types of unparalleled meroterpenoid *** struc-tures were elucidated by extensive spectroscopic analysis,nuclear magnetic resonance(NMR)calcula-tions,DP4+analysis and electronic circular dichroism(ECD)*** plausible biosynthetic path-ways for 1 and 2 were ***,2 exerted potent neuroprotective activities which were su-perior to trolox at 12.5 and 25μmol/***,1 and 2 exhibited more noticeable acetylcholinesterase inhibitory activities than *** docking simulations were performed to explore the inter-molecular interaction of compounds 1 and 2 with *** bioactivity evaluation results highlight the prospects of 1 and 2 as a novel category of neurological agents.

关键词： Daphne altaica Pall. Molecular networking MolNetEnhancer NAP Unprecedented meroterpenoid frameworks Neuroprotective activities Acetylcholinesterase inhibitors

Diverse sesquiterpenoids from Litsea lancilimba *** potential neuroprotective effects against H_(2)O_(2)-induced SH-SY5Y cell injury

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Chinese Journal of Natural Medicines 2022年第9期20卷 701-711页

作者： ZHANG Yi-Jie BAI Ming LI Jia-Yi QIN Shu-Yan LIU Yu-Yang HUANG Xiao-Xiao ZHENG Jiang SONG Shao-Jiang key laboratory of Computational Chemistry-Based Natural Antitumor drug Research&development Liaoning ProvinceEngineering Research Center of Natural Medicine Active Molecule Research&DevelopmentLiaoning ProvinceKey Laboratory of Natural Bioactive Compounds Discovery&ModificationShenyangSchool of Traditional Chinese Materia MedicaShenyang Pharmaceutical UniversityShenyang 110016China Wuya College of Innovation Shenyang Pharmaceutical UniversityShenyang 110016China State key laboratory of Functions and Applications of Medicinal Plants Guizhou Provincial Key Laboratory of PharmaceuticsGuizhou Medical UniversityGuiyang 550004China

Five undescribed sesquiterpenoids(1–5),and nine known sesquiterpenoids(6–14)were obtained from the fruits of Litsea lancilimba *** LC-MS/MS molecular networking *** A(1)possessed a unique 8-member ring through unexpected cyclization of the methyl group on C-10 of *** structures were elucidated by spectroscopic techniques including IR,UV,NMR,HR-ESI-MS,and their absolute configurations were assigned by ECD *** isolated sesquiterpenoids were analyzed by bioinformatics and evaluated for their neuroprotective effects against H_(2)O_(2)-induced injury in human neuroblastoma SH-SY5Y cells.

关键词： Litsea lancilimba Lauraceae Sesquiterpenoids Neuroprotective effect

Small molecule-based immunomodulators for cancer therapy

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Acta Pharmaceutica Sinica B 2022年第12期12卷 4287-4308页

作者： Yinrong Wu Zichao Yang Kui Cheng Huichang Bi Jianjun Chen Guangdong Provincial key laboratory of New drug Screening NMPA Key Laboratory for Research and Evaluation of Drug MetabolismSchool of Pharmaceutical SciencesSouthern Medical UniversityGuangzhou 510515China

Immunotherapy has led to a paradigm shift in the treatment of *** cancer immunotherapies are mostly antibody-based,thus possessing advantages in regard to pharmacodynamics(e.g.,specificity and efficacy).However,they have limitations in terms of pharmacokinetics including long half-lives,poor tissue/tumor penetration,and little/no oral *** addition,therapeutic antibodies are immunogenic,thus may cause unwanted adverse ***,researchers have shifted their efforts towards the development of small molecule-based cancer immunotherapy,as small molecules may overcome the above disadvantages associated with ***,small molecule-based immunomodulators and therapeutic antibodies are complementary modalities for cancer treatment,and may be combined to elicit synergistic *** years have witnessed the rapid development of small molecule-based cancer *** this review,we describe the current progress in small molecule-based immunomodulators(inhibitors/agonists/degraders)for cancer therapy,including those targeting PD-1/PD-L1,chemokine receptors,stimulator of interferon genes(STING),Toll-like receptor(TLR),*** tumorigenesis mechanism of various targets and their respective modulators that have entered clinical trials are also summarized.

关键词： Cancer immunotherapy Small molecules Immunomodulators Inhibitors Agonists

Research progress on natural products against hepatocellular carcinoma

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BIOCELL 2024年第6期48卷 905-922页

作者： LINGLI ZHANG YAN LI JINGXIN MAO Chongqing key laboratory of High active Traditional Chinese drug Delivery System Chongqing Medical and Pharmaceutical CollegeChongqing400030China Provincial key laboratory of Pharmaceutical Bioactive Substances School of Life Sciences and BiopharmaceuticalsGuangdong Pharmaceutical UniversityGuangzhou510006China

Hepatocellular carcinoma(HCC)remains a prevalent and challenging malignancy globally,characterized by its numerous causal factors and generally unfavorable *** the relentless pursuit of effective treatment modalities,natural products have emerged as a promising and relatively non-toxic alternative,garnering signiﬁcant *** integration of natural products with contemporary medical research has yielded encouraging therapeutic outcomes in the management of *** review offers a comprehensive overview of the causal factors underlying HCC,and the diverse treatment options available,and highlights the advancements made by natural products in anti-HCC ***,we provide an outline of the various types of natural products,their corresponding nomenclature,target molecules,and mechanisms of action that exhibit anti-HCC *** products are anticipated to play a pivotal role in future comprehensive treatment plans for liver cancer,potentially offering patients improved survival rates and an enhanced quality of life.

关键词： Hepatocellular carcinoma Natural products Targets Research progress drug

Mimotope peptide modified pompon mum-like magnetic microparticles for precise recognition,capture and biotransformation analysis of rituximab in biological fluids

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Acta Pharmaceutica Sinica B 2024年第3期14卷 1317-1328页

作者： Jiawen Yang Aixuan Zhou Minyi Li Qiaoxian He Jingwei Zhou Jacques Crommen Wentao Wang Zhengjin Jiang Qiqin Wang Institute of Pharmaceutical Analysis College of Pharmacy/State Key Laboratory of Bioactive Molecules and Druggability Assessment/International Cooperative Laboratory of Traditional Chinese Medicine Modernization and Innovative Drug Development of Ministry of Education(MOE)of ChinaJinan UniversityGuangzhou 510632China laboratory for the Analysis of Medicines Department of Pharmaceutical SciencesCIRMUniversity of LiegeLiege B-4000Belgium SCIEX Shanghai 200050China

Due to low immobilized ligand density,limited binding capacity,and severe interference from serum proteins,developing ideal peptide-based biomaterials for precise recognition and in vivo analysis of biopharmaceuticals remains a huge *** this study,mimotope peptide modified pompon mum-like biomimetic magnetic microparticles(MMPs,3.8μm)that mimic the specific functionalities of CD20 on malignant B cells were developed for the first *** from the numerous ligand binding sites(Ni^(2+))on the pompon mum-like MMPs,these novel materials achieved≥10 times higher peptide ligand densities(>2300 mg/g)and antibody binding capacities(1380 mg/g)compared to previous reported *** the high specificity of the mimotope peptide,rituximab can be precisely recognized and enriched from cell culture media or serum *** also established an LC-MS/MS method using the MMPs for tracking rituximab biotransformation in patient ***,deamidation of Asn55 and Asn33,as well as oxidation of Met81 and Met34 were observed at the key complementarity determining regions of rituximab,which could potentially influence antibody function and require careful ***,these versatile biomimetic MMPs demonstrate superior recognition and enrichment capabilities for target antibodies,offering interesting possibilities for biotransformation analysis of biopharmaceuticals in patient serum.

关键词： Therapeutic monoclonal antibody Mimotope peptide Precise recognition Peptide-based biomaterials Biotransformation Patient serum

Collaborative assembly-mediated siRNA delivery for relieving inflammation-induced insulin resistance

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Nano Research 2020年第11期13卷 2958-2966页

作者： Shiyang Shen Li Zhang Mengru Li Zhizi Feng Huixia Li Xiao Xu Shiqi Lin Ping Li Can Zhang Xiaojun Xu Ran Mo State key laboratory of Natural Medicines Jiangsu Key Laboratory of Drug Discovery for Metabolic DiseasesCenter of Advanced Pharmaceuticals and BiomaterialsChina Pharmaceutical UniversityNanjing210009China

Obesity plays a primary causative role in insulin resistance and hyperglycemia that contributes to type 2 *** lipid storage in the liver renders activation of the resident macrophages and chronic secretion of inflammatory mediators,therefore causing or aggravating insulin ***,we develop collaborative assemblies using a“one-pot”synthesis method for macrophage-specific delivery of small interfering RNAs(siRNAs)that target the inflammatory *** nanocomplex(NC)composed of the siRNA molecule,a synthetic thiol-bearing methacrylated hyaluronic acid(sm-HA)and protamine forms through an electrostatic-driven physical assembly,which is chemically crosslinked to acquire the collaboratively assembled nanocapsule(cNC)*** obtained cNC displays significantly higher stability than *** moieties as flexible assembly units can be easily equipped on cNC for long circulation,active targeting,or controlled siRNA ***-F decorated with folic acid,a macrophage-targeting ligand promotes the siRNA accumulation in the activated macrophages in the liver of the obese mouse ***-F loaded with siRNA targeting inflammatory indicators efficiently control the macrophage inflammatory response by reducing the expression of the inflammatory proteins(>40%reduction)and ameliorating the insulin resistance symptoms of the obese mice.

关键词： small interfering RNA(siRNA)delivery collaborative assembly nanomedicine insulin resistance diabetes