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Frontier studies on natural products:moving toward paradigm shifts

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Science China Chemistry 2023年第4期66卷 928-942页

作者： Jin-Xin Zhao Jian-Min Yue State Key laboratory of drug Research Shanghai Institute of Materia MedicaChinese Academy of SciencesShanghai 201203China shandong laboratory of yantai drug discovery Bohai Rim Advanced Research Institute for Drug DiscoveryYantai 264117China

1 Introduction Natural products(NPs)historically serve as a valuable and productive source of bioactive compounds for drug *** discovery of a range of alkaloids in the early1800s,including strychnine,morphine,etc.,her... 详细信息

关键词： alkaloids moving compounds

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Rearranged Dichapetalin-Type Triterpenoids with Cytotoxic Activity from Dichapetalum gelonioides

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Chinese Journal of Chemistry 2022年第21期40卷 2531-2538页

作者： Xin-Hua Gao Xi-Yuan Wang Jun-Su Zhou Yan Zhang Hong-Chun Liu Bin Zhou Jian-Min Yue State Key laboratory of drug Research Shanghai lnstitute of Materia MedicaChinese Academy of SciencesShanghai 201203China Research Units of discovery of New drug Lead Molecules Chinese Academy of Medical SciencesShanghai 201203china shandong laboratory of yantai drug discovery Bohai Rim Advanced Research Institute for Drug DiscoveryYantaiShandong 264117China

Dichagelinoids A—C(1—3),three unusual dichapetalin-type triterpenoids,together with two biogenetically related derivatives dichagelinoids D and E(4 and 5)were isolated and characterized by solid data from Dichapetalum *** 1—3 possess a common rearranged C ring and different C6—C2 modified motifs at the A *** evaluation revealed that compounds 1—3 showed distinct cytotoxic activity against the tested human cancer cell lines.

关键词： Dichapetalum gelonioides Natural products Dichapetalin-type triterpenoids Structural elucidation Cytotoxic activity

Recent advances in developing active targeting and multi-functional drug delivery systems via bioorthogonal chemistry

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Signal Transduction and Targeted Therapy 2023年第1期8卷 13-37页

作者： Wenzhe Yi Ping Xiao Xiaochen Liu Zitong Zhao Xiangshi Sun Jue Wang Lei Zhou Guanru Wang Haiqiang Cao Dangge Wang Yaping Li State Key laboratory of drug Research&Center of Pharmaceutics Shanghai Institute of Materia MedicaChinese Academy of SciencesShanghai 201203China yantai Key laboratory of Nanomedicine&Advanced Preparations Yantai Institute of Materia MedicaYantai 264000China shandong laboratory of yantai drug discovery Bohai Rim Advanced Research Institute for Drug DiscoveryYantai 264000China

Bioorthogonal chemistry reactions occur in physiological conditions without interfering with normal physiological *** metabolic engineering,bioorthogonal groups can be tagged onto cell membranes,which selectively attach to cargos with paired groups via bioorthogonal *** to its simplicity,high efficiency,and specificity,bioorthogonal chemistry has demonstrated great application potential in drug *** the one hand,bioorthogonal reactions improve therapeutic agent delivery to target sites,overcoming off-target *** the other hand,nanoparticles and biomolecules can be linked to cell membranes by bioorthogonal reactions,providing approaches to developing multi-functional drug delivery systems(DDSs).In this review,we first describe the principle of labeling cells or pathogenic microorganisms with bioorthogonal *** then highlight recent breakthroughs in developing active targeting DDSs to tumors,immune systems,or bacteria by bioorthogonal chemistry,as well as applications of bioorthogonal chemistry in developing functional bio-inspired DDSs(biomimetic DDSs,cell-based DDSs,bacteria-based and phage-based DDSs)and ***,we discuss the difficulties and prospective direction of bioorthogonal chemistry in drug *** expect this review will help us understand the latest advances in the development of active targeting and multi-functional DDSs using bioorthogonal chemistry and inspire innovative applications of bioorthogonal chemistry in developing smart DDSs for disease treatment.

关键词： functional orthogonal breakthrough

Suadimins D—J,Monoterpenoid Indole-Quinoline and Bisindole Alkaloids from Melodinus suaveolens

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Chinese Journal of Chemistry 2023年第18期41卷 2296-2304页

作者： Xin-Hua Gao Pei-Qian Wu Yao-Yue Fan Bin Zhou Jian-Min Yue State Key laboratory of drug Research Shanghai Institute of Materia MedicaChinese Academy of Sciences555 Zuchongzhi RoadShanghai201203China shandong laboratory of yantai drug discovery Bohai Rim Advanced Research Institute for Drug DiscoveryYantaiShandong 264117China Research Units of discovery of New drug Lead Molecules Chinese Academy of Medical SciencesShanghai 201203China

Comprehensive Summary,Compounds 1—12,including seven complex monoterpenoid indole-quinoline and bisindole alkaloids,suadimins D—J(1—7)with previously unreported carbon-carbon linkages,were isolated and identified from the twigs and leaves of Melodinus *** structures were elucidated by a combination of diverse methods,especially the extensive spectroscopic data analysis and electric circular dichroism(ECD)*** cytotoxicity of these compounds against three cancer cell lines was evaluated,some of which showed moderate activities with IC50 values ranging from 2.4 to 8.0μM.

关键词： Melodinus suaveolens Alkaloids Dimerization Structure elucidation ECD calculations Cytotoxic activity

The biologically and ecologically important natural products from the Chinese sea hare Bursatella leachii:structures,stereochemistry and beyond

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Chinese Journal of Natural Medicines 2024年第11期22卷 1030-1039页

作者： ZHANG Xinyuan SU Mingzhi ZHU Mingxin CHEN Sha GAO Zhen GUO Yuewei LI Xuwen School of Chinese Materia Medica Nanjing University of Chinese MedicineNanjing 210023China State Key laboratory of Chemical Biology Shanghai Institute of Materia MedicaChinese Academy of SciencesShanghai 201203China shandong laboratory of yantai drug discovery Bohai Rim Advanced Research Institute for Drug DiscoveryYantai 264117China

A novel amide alkaloid,bursatamide A(1),featuring an unprecedented propyl-hexahydronaphthalene carbon frame-work,was isolated from the infrequently studied sea hare Bursatella leachi,alongside a new 3-phenoxypropanenitrile alkaloid,bursatellin B(2),and twelve known *** structures of 1 and 2 were elucidated through comprehensive spectroscopic data analyses,while their relative and absolute configurations(ACs)were established through total synthesis and a series of quantum chem-ical calculations,including calculated electronic circular dichroism(ECD)spectra,optical rotatory dispersion(ORD)methods,and DP4^(+) probability *** A(1)demonstrated inhibitory effects against the human pathogenic bacteria Listeria monocyt-ogenes and Vibrio ***-bursatellin B(21),a diastereoisomer of 2,exhibited notable antibacterial activity against the fish pathogenic bacterium Streptococcus parauberis FP KSP28,with an MIC90 value of 0.0472 μg·mL^(-1).

关键词： Bursatella leachii Marine natural product Alkaloid Sea hare Antibacterial activity

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Smart drug delivery systems to overcome drug resistance in cancer immunotherapy

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Cancer Biology & Medicine 2023年第4期20卷 248-267页

作者： Wenzhe Yi Dan Yan Dangge Wang Yaping Li State Key laboratory of drug Research&Center of Pharmaceutics Shanghai Institute of Materia MedicaChinese Academy of SciencesShanghai 201203China University of Chinese Academy of Sciences Beijing 100049China Department of Pharmaceutics School of PharmacyNanjing Medical UniversityNanjing 211116China yantai Key laboratory of Nanomedicine&Advanced Preparations Yantai Institute of Materia MedicaYantai 264000China shandong laboratory of yantai drug discovery Bohai Rim Advanced Research Institute for Drug DiscoveryYantai 264000China

Cancer immunotherapy,a therapeutic approach that inhibits tumors by activating or strengthening anti-tumor immunity,is currently an important clinical strategy for cancer treatment;however,tumors can develop drug resistance to immune surveillance,resulting in poor response rates and low therapeutic *** addition,changes in genes and signaling pathways in tumor cells prevent susceptibility to immunotherapeutic ***,tumors create an immunosuppressive microenvironment via immunosuppressive cells and secrete molecules that hinder immune cell and immune modulator infiltration or induce immune cell *** address these challenges,smart drug delivery systems(SDDSs)have been developed to overcome tumor cell resistance to immunomodulators,restore or boost immune cell activity,and magnify immune *** combat resistance to small molecules and monoclonal antibodies,SDDSs are used to co-deliver numerous therapeutic agents to tumor cells or immunosuppressive cells,thus increasing the drug concentration at the target site and improving ***,we discuss how SDDSs overcome drug resistance during cancer immunotherapy,with a focus on recent SDDS advances in thwarting drug resistance in immunotherapy by combining immunogenic cell death with immunotherapy and reversing the tumor immunosuppressive *** that modulate the interferon signaling pathway and improve the efficacy of cell therapies are also ***,we discuss potential future SDDS perspectives in overcoming drug resistance in cancer *** believe that this review will contribute to the rational design of SDDSs and development of novel techniques to overcome immunotherapy resistance.

关键词： Cancer immunotherapy drug resistance smart drug delivery system immunosuppressive microenvironment immune cell

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Two Terpenoid Derivatives with Different 3/5/6/6/5-Fused Pentacyclic Skeletons from Hedyosmum orientale

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Chinese Journal of Chemistry 2023年第4期41卷 392-398页

作者： Yao-Yue Fan Cheng-Yu Zheng Bin Zhou Flavia M.Zimbres Maria B.Cassera Jian-Min Yue State Key laboratory of drug Research Shanghai Institute of Materia MedicaChinese Academy of Sciences555 Zuchongzhi RoadShanghai201203 China shandong laboratory of yantai drug discovery Bohai Rim Advanced Research Institute for Drug DiscoveryYantaiShandong264117 China Research Units of discovery of New drug Lead Molecules Chinese Academy of Medical SciencesShanghai201203 China Department of Biochemistry and Molecular Biology Center for Tropical and Emerging Global Diseases(CTEGD)University of GeorgiaAthensGeorgia30602 United States

Chemical investigation of Hedyosmum orientale led to the identification of two terpenoid derivatives,dyosmunoids A and B(1 and 2)featuring two different 3/5/6/6/5-fused pentacyclic ring systems,*** 1 is the second natural product of this C_(25) terpenoid compound class,and compound 2 is a rare dinor-C25 terpenoid with a peroxide *** structural elucidation was achieved by the comprehensive analysis of spectroscopic data,single-crystal X-ray diffraction,and ECD *** biosynthetic pathways for compounds 1 and 2 are *** 2 exhibited strong antimalarial activity with an IC_(50) value of 0.42μmol·L^(-1).

关键词： Natural products C_(25)Terpenoids Structure elucidation Biosynthetic pathway hypothesis Antimalarial activity

STING agonist-boosted mRNA immunization via intelligent design of nanovaccines for enhancing cancer immunotherapy

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National Science Review 2023年第10期10卷 123-138页

作者： Lei Zhou Wenzhe Yi Zehong Zhang Xiaoting Shan Zitong Zhao Xiangshi Sun Jue Wang Hao Wang Hualiang Jiang Mingyue Zheng Dangge Wang Yaping Li State Key laboratory of drug Research & Center of Pharmaceutics Shanghai Institute of Materia MedicaChinese Academy of Sciences China State Institute of Pharmaceutical Industry Univerisity of Chinese Academy of Sciences drug discovery and Design Center State Key Laboratory of Drug Research Shanghai Institute of Materia Medica Chinese Academy of Sciences Precision Research Center for Refractory Diseases Shanghai General HospitalShanghai Jiao Tong University School of Medicine shandong laboratory of yantai drug discovery Bohai Rim Advanced Research Institute for Drug Discovery

Messenger RNA(mRNA) vaccine is revolutionizing the methodology of immunization in ***,mRNA immunization is drastically limited by multistage biological barriers including poor lymphatic transport,rapid clearance,catalytic hydrolysis,insufficient cellular entry and endosome ***,we design a mRNA nanovaccine based on intelligent design to overcome these *** efficient nanovaccines are carried out with machine learning techniques from datasets of various nanocarriers,ensuring successful delivery of mRNA antigen and cyclic guanosine monophosphate-adenosine monophosphate(cGAMP) to *** activates stimulator of interferon genes(STING),promotes mRNA-encoded antigen presentation and boosts antitumour immunity in vivo,thus inhibiting tumour growth and ensuring long-term survival of tumour-bearing *** work provides a feasible and safe strategy to facilitate STING agonist-synergized mRNA immunization,with great translational potential for enhancing cancer immunotherapy.

关键词： vaccine mRNA STING cancer immunotherapy nanoparticles

pH- and near-infrared light-responsive,biomimetic hydrogels from aqueous dispersions of carbon nanotubes

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Nano Research 2024年第4期17卷 3120-3129页

作者： Lulin Hu Xinxin Yu Jingcheng Hao Lu Xu shandong laboratory of yantai Advanced Materials and Green Manufacturing Yantai 264000China State Key laboratory of Solid Lubrication Lanzhou Institute of Chemical PhysicsChinese Academy of SciencesLanzhou 730000China yantai Center for Food and drug Control Yantai 264000China Key laboratory of Colloid and Interface Chemistry&Key laboratory of Special Aggregated Materials Shandong UniversityJinan 250100China

Owing to their low flexibility,poor processability and a lack of responsiveness,inorganic materials are usually non-ideal for constructing a living ***,to date,lifelike materials with structural hierarchies and adaptive properties usually rely on light and soft organic molecules,although few exceptions have been acquired using two-dimensional(2D)inorganic ***,with a systematic study on the gelation behavior of carbon-based 0D quantum dots,1D nanotubes,and 3D fullerenes,we find that acidified 1D carbon nanotubes(CNTs)can serve as an alternative building block for fabricating purely inorganic biomimetic soft *** as-prepared CNT gels exhibit not only a pH-or photothermal-triggered mechanical and tribological adaptivity,which allows them to simulate the behavior of sea cucumbers,peacock mantis shrimps,and mammalian muscles or cortical bones,but also a unique damping property that is similar to spider’s cuticular *** high elasticity,effective lubrication,excellent biocompatibility,and controllable friction and wear also allow them to function as a new type of smart lubricants,whose tribological properties can be regulated either by its internal pH changes or spatiotemporally by near-infrared(NIR)light irradiations,free of any toxic and flammable base oils or additives.

关键词： biomimetic hydrogels carbon nanotubes(CNTs) mechanical and tribological adaptivity pH-and near-infrared(NIR)light responsiveness switchable lubrication