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Constituents from leaves of Macaranga hemsleyana

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Chinese Herbal Medicines 2024年第3期16卷 481-486页

作者： Joseph Sakah Kaunda Jia Liu Yaojun Xu Yuansi Chen Chenfang Yue Xingjie Zhang Ruihan Zhang Muhammad Amin Weilie Xiao Hongliang Li Xiaoli Li Key laboratory of Medicinal chemistry for natural Resource Ministry of EducationYunnan Characteristic Plant Extraction LaboratoryYunnan Provincial Center for Research&Development of Natural ProductsState Key Laboratory for Conservation and Utilization of Bio-Resources in YunnanSchool of PharmacySchool of MedicineChemical Science and TechnologyYunnan UniversityKunming 650500China Yunnan Key laboratory of Pharmacology for natural products Haiyuan CollegeKunming Medical UniversityKunming 650500China

Objective:To study constituents of the leaves of Macaranga hemsleyana,and evaluate their inhibitory effects against NOD-like receptor thermal protein domain associated protein 3(NLRP3)inflammasome activation,and antiproliferative ***:The constituents were isolated and purified by column chromatography on MCI gel CHP20P/P120,silica gel,Sephadex LH-20,and *** structures of compounds were determined by 1D,2D NMR,and HR-ESI-MS *** inhibitory effect of compounds on inflammasome activation was determined by lactate dehydrogenase(LDH)*** antiproliferative activity was evaluated using MTT ***:The study led to the isolation of 23 compounds,including one new compound,identified as(2Z)-3-[4-(β-D-glucopyranosyloxy)-2′-hydroxy-5′-methoxyphenyl]-2-propenoic acid(1),together with 22 known compounds recognized as 1,4-dihydro-4-oxo-3-pyridinecarbonitrile(2),methyl 4-methoxynicotinate(3),4-methoxynicotinonitrile(4),1-(3-O-β-D-glucopyranosyl-4,5-dihydroxyphenyl)-ethanone(5),neoisoastilbin(6),isoastilbin(7),aromadendrin(8),neoastilbin(9),astilbin(10),quercitrin(11),neoschaftoside(12),apigenin 6,8-bis-C-α-L-arabinoside(13),vitexin(14),bergenin(15),scopoletin(16),glucopyranoside salicyl(17),koaburside(18),benzylβ-D-glucoside(19),icariside B5(20),roseoside(21),loliolide(22),and adenosine(23).The tested compounds did not show LDH inhibition nor antiproliferative ***:Compound 1 was a new *** 2 and 3 were obtained for the first time from natural *** 22 known compounds constituted of alkaloids(2–4,23),phenolics(5,15,17,18),flavonoids(6–14),coumarin(16),benzyl glycoside(19),and norsesquiterpenes(20–22).All the compounds,1–23,were revealed from *** for the first *** is the initial uncovering of molecules 1–10,12,13,17–19,and 23 from the genus *** isolated compounds,11,14–16,and 20–22 established taxonomic classification of *** in Euphorbiaceae *** were outstanding as

关键词： antiproliferative activity chemotaxonomic significance flavonoids glycoside Macaranga hemsleyana Pax et Hoffm NLRP3 inflammasome

Parallelogram 3d-4f-5d heterometallic clusters based on trilacunary tungstoantimonates with excellent proton conductivity

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Chinese Chemical Letters 2024年第3期35卷 528-531页

作者： Haiying Wang Han Xu Chaolong Chen Yingjie Zhu Yikang Zhang Dongdi Zhang Jingyang Niu Henan Key laboratory of Polyoxometalate chemistry College of Chemistry and Molecular SciencesHenan UniversityKaifeng 475004China School of Pharmaceutical Science&Yunnan Key laboratory of Pharmacology for natural products Kunming Medical UniversityKunming 650500China Collaborative Innovation Center of chemistry for Energy Materials State Key Laboratory of Physical Chemistry of Solid Surface and Department of ChemistryCollege of Chemistry and Chemical EngineeringXiamen UniversityXiamen 361005China

Two 3d-4f-5d heterometallic cluster-containing polyoxometalates,formulated as Na_(22){(SbW_(9)O_(33))_(4)[La_(3)W_(6)MO_(18)(H_(2)O)_(8)(CH_(3)COO)_(4)]_(2)}·nH_(2)O(abbreviated as La_(6)M_(2),M=Co/Mn)were synthesized and structurally ***-crystal X-ray diffraction analyses reveal that the polyanions of La_(6)Co_(2)and La_(6)Mn_(2)consist of the uncommon 3d-4f-5d clusters{La_(6)W_(12)Co_(2)}and{La_(6)W_(12)Mn_(2)},which are encapsulated by four trilacunary Keggin tungstoantimonates to form the parallelogram-shaped title ***,the polyanions can be extended into a two-dimensional(2D)frame by the linkage of peripheral Na+*** inner space of the 2D layer was filled with water molecules and thus an H-bonded network was formed,which is expected to exhibit a fascinating proton *** study of water-assisted proton conduction demonstrated that La_(6)Co_(2)and La_(6)Mn_(2)were temperature-and humiditydependent proton conductors,respectively,and the proton conductivities could reach 1.3×10^(-2)and 2.3×10^(-2)S/cm at 65℃and 90%RH conditions.

关键词： Polyoxometalate Parallelogram Heterometallic 3d-4f-5d cluster Proton conductivity

Rearranged 19-nor-7,8-seco-labdane diterpenoids and Diels-Alder cycloadducts from the Chinese liverwort Pallavicinia ambigua:Structural elucidation,photoinduced rearrangement,and cytotoxic activity

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Chinese Chemical Letters 2024年第3期35卷 415-418页

作者： Chunyang Zhang Yuelan Li Zhaojun Chu Shuangzhi Yuan Yanan Qiao Jiaozhen Zhang Lin Li Yueqing Zhang Ruifeng Tian Yajie Tang Hongxiang Lou Department of natural products chemistry Key Lab of Chemical Biology(MOE)School of Pharmaceutical SciencesShandong UniversityJi'nan 250012China State Key laboratory of Microbial Technology Shandong UniversityQingdao 266237China

Two distinctive rearranged 19-nor-7,8-seco-labdane diterpenoids(1 and 2)with a novel tetracyclo[5.***.1.0^(2,5.)0^(4,10)]decane skeleton,a derivative of the open tetrahydrofuran ring(7),three dimeric compounds(8-10),and four revised homologs(3-6)were obtained from Chinese liverwort Pallavicinia *** structures were identified via combined analysis of their spectroscopic data,single-crystal X-ray diffraction patterns,and ECD *** light-driven conversion of compound 5 to compounds 1-4 demonstrated that photochemically induced postmodification involved in biosynthesis is an important way to diversify natural structures.A preliminary cytotoxicity assay revealed that compound 5 showed significant inhibition in the human prostate cancer(PC-3)cell line via an apoptotic pathway.

关键词： Liverwort Pallavicinia ambigua 19-nor-7 8-seco-Labdan diterpenoid Photoinduced rearrangement Cytotoxic activity

Uncovering the dominant contribution of intermediate volatility compounds in secondary organic aerosol formation from biomass-burning emissions

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National Science Review 2024年第3期11卷 150-158页

作者： Kun Li Jun Zhang David M.Bell Tiantian Wang Houssni Lamkaddam Tianqu Cui Lu Qi Mihnea Surdu Dongyu Wang Lin Du Imad El Haddad Jay G.Slowik Andre S.H.Prevot Environment research Institute Shandong University laboratory of Atmospheric chemistry Paul Scherrer Institute

Organic vapors from biomass burning are a major source of secondary organic aerosols(SOAs). Previous smog chamber studies found that the SOA contributors in biomass-burning emissions are mainly volatile organic compounds(VOCs). While intermediate volatility organic compounds(IVOCs) are efficient SOA precursors and contribute a considerable fraction of biomass-burning emissions, their contribution to SOA formation has not been directly observed. Here, by deploying a newly-developed oxidation flow reactor to study SOA formation from wood burning, we find that IVOCs can contribute ～70% of the formed SOA, i.e.>2 times more than VOCs. This previously missing SOA fraction is interpreted to be due to the high wall losses of semi-volatile oxidation products of IVOCs in smog chambers. The finding in this study reveals that SOA production from biomass burning is much higher than previously thought, and highlights the urgent need for more research on the IVOCs from biomass burning and potentially other emission sources.

关键词： atmospheric chemistry biomass burning secondary organic aerosol intermediate volatility organic compounds

Mechanism of action of the bile acid receptor TGR5 in obesity

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Acta Pharmaceutica Sinica B 2024年第2期14卷 468-491页

作者： Weijun Lun Qihao Yan Xinghua Guo Minchuan Zhou Yan Bai Jincan He Hua Cao Qishi Che Jiao Guo Zhengquan Su Guangdong Engineering research Center of natural products and New Drugs Guangdong Provincial University Engineering Technology Research Center of Natural Products and DrugsGuangdong Pharmaceutical UniversityGuangzhou 510006China Guangdong Metabolic Disease research Center of Integrated Chinese and Western Medicine Key Laboratory of Glucolipid Metabolic DisorderMinistry of Education of ChinaGuangdong TCM Key Laboratory for Metabolic DiseasesGuangdong Pharmaceutical UniversityGuangzhou 510006China School of Public Health Guangdong Pharmaceutical UniversityGuangzhou 510310China School of chemistry and Chemical Engineering Guangdong Pharmaceutical UniversityZhongshan 528458China Guangzhou Rainhome Pharm&Tech Co. Ltd.Science CityGuangzhou 510663China

G protein-coupled receptors(GPCRs)are a large family of membrane protein receptors,and Takeda G protein-coupled receptor 5(TGR5)is a member of this *** a membrane receptor,TGR5 is widely distributed in different parts of the human body and plays a vital role in regulating metabolism,including the processes of energy consumption,weight loss and blood glucose *** studies have shown that TGR5 plays an important role in glucose and lipid metabolism disorders such as fatty liver,obesity and *** the global obesity situation becoming more and more serious,a comprehensive explanation of the mechanism of TGR5 and filling the gaps in knowledge concerning clinical ligand drugs are urgently *** this review,we mainly explain the anti-obesity mechanism of TGR5 to promote the further study of this target,and show the electron microscope structure of TGR5 and review recent studies on TGR5 ligands to illustrate the specific binding between TGR5 receptor binding sites and ligands,which can effectively provide new ideas for ligand research and promote drug research.

关键词： Obesity TGR5 Bile acids Ligand Appetite Metabolism GLP-1 Inflammation

DNA G-Quadruplexes as Targets for natural Product Drug Discovery

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Engineering 2024年第7期38卷 39-51页

作者： Kai-Bo Wang Yingying Wang Jonathan Dickerhoff Danzhou Yang Borch Department of Medicinal chemistry and Molecular Pharmacology College of PharmacyPurdue UniversityWest LafayetteIN 47907USA Purdue Center for Cancer research Purdue UniversityWest LafayetteIN 47907USA Department of chemistry Purdue UniversityWest LafayetteIN 47907USA Purdue Institute for Drug Discovery Purdue UniversityWest LafayetteIN 47907USA Jiangsu Key laboratory of Bioactive natural Product research&State Key laboratory of natural Medicines China Pharmaceutical UniversityNanjing 210009China

DNA guanine(G)-quadruplexes(G4s)are unique secondary structures formed by two or more stacked Gtetrads in G-rich DNA *** structures have been found to play a crucial role in highly transcribed genes,especially in cancer-related oncogenes,making them attractive targets for cancer ***,targeting oncogene promoter G4 structures has emerged as a promising strategy to address the challenge of undruggable and drug-resistant proteins,such as MYC,BCL2,KRAS,and *** products have long been an important source of drug discovery,particularly in the fields of cancer and infectious *** progress has recently been made in the discovery of naturally occurring DNA G4-targeting *** DNA G4s,such as MYC-G4,BCL2-G4,KRAS-G4,PDGFR-b-G4,VEGF-G4,and telomeric-G4,have been identified as potential targets of natural products,including berberine,telomestatin,quindoline,sanguinarine,isaindigotone,and many ***,we summarize and evaluate recent advancements in natural and nature-derived DNA G4 binders,focusing on understanding the structural recognition of DNA G4s by small molecules derived from *** also discuss the challenges and opportunities associated with developing drugs that target DNA G4s.

关键词： G-quadruplex natural products Alkaloids Cancer Promoter

Semisynthesis of homogeneous spike RBD glycoforms from SARS-CoV-2 for profiling the correlations between glycan composition and function

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National Science Review 2024年第2期11卷 145-154页

作者： Farong Ye Cheng Li Feng-Liang Liu Xinliang Liu Peng Xu Rong-Hua Luo Wenping Song Yong-Tang Zheng Tianlei Ying Biao Yu Ping Wang Center for Chemical Glycobiology Frontiers Science Center for Transformative Molecules Zhangjiang Institute for Advanced Study School of Chemistry and Chemical Engineering Shanghai Jiao Tong University MOE/NHC/CAMS Key laboratory of Medical Molecular Virology Shanghai Frontiers Science Center of Pathogenic Microorganisms and Infection Shanghai Institute of Infectious Disease and BiosecurityShanghai Engineering Research Center for Synthetic ImmunologySchool of Basic Medical Sciences Shanghai Medical College Fudan University Key laboratory of Animal Models and Human Disease Mechanisms of Chinese Academy of Sciences/Key laboratory of Bioactive Peptides of Yunnan Province Center for Biosafety Mega-Science Kunming Institute of ZoologyChinese Academy of Sciences State Key laboratory of Bioorganic and natural products chemistry Center for Excellence in Molecular Synthesis Shanghai Institute of Organic Chemistry Chinese Academy of Sciences Shenzhen research Institute of Shanghai Jiao Tong University

Vaccines have been the primary remedy in the global fight against coronavirus disease 2019（COVID-19）.The receptor-binding domain（RBD） of the spike protein, a critical viral immunogen, is affected by the heterogeneity of its glycan structures and relatively low immunogenicity. Here, we describe a scalable synthetic platform that enables the precise synthesis of homogeneously glycosylated RBD, facilitating the elucidation of carbohydrate structure–function relationships. Five homogeneously glycosylated RBDs bearing biantennary glycans were prepared, three of which were conjugated to T-helper epitope(Tpep) from tetanus toxoid to improve their weak immune response. Relative to natural HEK293-derived RBD, synthetic RBDs with biantennary N-glycan elicited a higher level of neutralising antibodies against SARS-CoV-2 in mice. Furthermore, RBDs containing Tpepelicited significant immune responses in transgenic mice expressing human angiotensin-converting enzyme 2. Our collective data suggest that trimming the N-glycans and Tpepconjugation of RBD could potentially serve as an effective strategy for developing subunit vaccines providing efficient protection.

关键词： peptide ligation glycosylation glycoprotein

Bovine and Goat Milk Fat Globule Membrane Supplementation Alleviates Autism-like Behavior by Modulating Lipid Metabolism and Gut Microbiota

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Food Science and Human Wellness 2024年

作者： Rui Guo Xiao Xiao Chuanchuan Wang Tian Yuan Qianhui Zou Tian Zhang Jiarui Liang Ying He Zhuo Liu Xuebo Liu Shan Wu Zhigang Liu Northwest A&F University Shenzhen research Institute Shaanxi Precision Nutrition and Health research Institute research and Development Center Xi'an Yinqiao Dairy (Group) Co. Ltd laboratory of Functional chemistry and Nutrition of Food College of Food Science and Engineering Northwest A&F University Shaanxi Key laboratory of natural products & Chemical Biology College of chemistry & Pharmacy Northwest A&F University

ASD (autism spectrum disorder) is a neurodevelopmental disorder influenced by genes and the environment. This study investigated the protective effects of bovine MFGM (BMFGM) and goat MFGM (GMFGM) supplementation on ASD model mice. Analysis of phospholipid composition showed higher levels of phosphatidylcholine in BMFGM and phosphatidylethanolamine in GMFGM. Behavioral results indicated MFGMs ameliorated social deficits， with GMFGM being more effective. MFGMs mitigated neuroinflammation by suppressing microglial overactivation and proinflammatory cytokines expression， meanwhile GMFGM increased the anti-inflammatory factor IL-10. MFGMs also altered gut microbiota composition and maintained gut barrier integrity. Uniquely， GMFGM increased butyrate production. Correlation analysis revealed positive associations between social behavior， levels of phosphatidylcholine， sphingomyelin， and the abundance of Allobaculum， Clostridium＿sensu＿stricto， and Turicibacter. Overall， these findings revealed the protective effects of MFGMs on neurodevelopment in ASD animal models and the underlying mechanism could be partly explained by their regulation of gut microbiota by the phospholipid components in MFGMs.

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Chiral transfer amidst one-dimensional linear polymers and twodimensional network covalent organic frameworks:Striking a fine balance between helicity and crystallinity

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Nano research 2024年第6期17卷 5726-5734页

作者： Xinlin Zha Mengjuan Zuo Guilin Xu Zhong Yan Haining You Yi Xiong Ying Liu Yingying Li Liyan Yang Ke Liu Mufang Li Tao Zhao Dong Wang College of chemistry and Chemical Engineering Donghua UniversityShanghai 201620China Key laboratory of Textile Fiber and products Ministry of EducationWuhan Textile UniversityWuhan 430200China

The current landscape of chiral covalent organic frameworks(COFs)predominantly centered on constructing asymmetric molecular-scale chirality,often introducing an inherent contradiction to the COF symmetry and limiting ***,we overcome these challenges by achieving chiral transfer between one-dimensional(1D)imine linear polymers(LPs)and two-dimensional(2D)networkβ-ketoenamine COFs composed of achiral *** successfully synthesize several 1D imine LPs with mesoscopic helical chirality,comprising achiral C2-symmetric terephthalaldehyde and diamine linkers in a chiral supramolecular transcription *** the irreversible tautomerism mechanism within the linker replacement approach,terephthalaldehyde(TPA)units in these helical 1D LPs are substituted with C3-symmetric 1,3,5-triformylphloroglucinol(TP),yielding the corresponding 2D networkβ-ketoenamine *** and helicity of the resultantβ-ketoenamine COFs intimately hinge on reaction conditions,including the aldehyde stoichiometry of Tp and TPA,as well as the quantity and concentration of the catalyst *** optimized conditions,the nucleation and growth were precisely governed,achieving a harmonious equilibrium of crystallinity and helicity within the generated 2D networkβ-ketoenamine COFs,even with covalent bond rupture,recombination,and topological transition(from[C2+C2]to[C3+C2]).Impressively,the ground state chirality inherent to helical 1D LPs seamlessly transfers to helical 2D networkβ-ketoenamine *** study not only offers new perspectives on the development of chiral functional COFs,but also provides fresh insights into the precise control of COFs'microscopic morphology.

关键词： chiral covalent organic frameworks chiral transfer dimensional transformation helicity