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Screening and identifying natural products with SARS-CoV-2 infection inhibitory activity from medicinal fungi

Biosafety and Health 2024年第1期6卷 12-20页

作者： Shuang Zhao Amelia Siqi Huang Weibo Zhang Lili Ren Hexiang Wang Jianbin Wang Xinyang Shao Guanbo Wang Institute of Agri-Food Processing and Nutrition Institute of Plant ProtectionBeijing Academy of Agriculture and Forestry SciencesBejing 100097China Bejing Key Laboratory of Fruits and Vegetable Storage and Processing Key Laboratory of Vegetable Postharvest ProcessingMinistry of AgricultureBejing 100097China Dalton Academy The Affliated High School of Peking UniversityBeijing 100190China NHC Key Laboratory of Systems Biology of Pathogens and Christophe Merieux Laboratory National Institute of Pathogen BiologyBejing 100730China Key Laboratory of Respiratory Disease Pathogenomics Chinese Academy of Medical Sciences and Peking Union Medical CollegeBeijing 100730China College of Biological Sciences China Agricultural UniversityBejing 100193China School of Life Sciences Tsinghua UniversityBeijing 100084China Changping Laboratory Beijing 102206China Institute for Cell Analysis Shenzhen Bay LaboratoryShenzhen 518132China

The coronavirus disease of 2019(COVID‐19),a global pandemic caused by the severe acute respiratory syndrome coronavirus 2(SARS‐CoV‐2),can result in severe health complications.In addition to physical preventative measures,pharmaceutical intervention is also crucial.Numerous natural products from medicinal fungi have shown promise as potential antiviral drugs and may serve as a source of effective components with antiviral activity against SARS‐CoV‐2 and other coronaviruses.In this study,we developed a workflow that integrates viral infection inhibition assays at both cellular and molecular levels,as well as molecular separation and characterization,to screen and identify natural products with antiviral activity.Using this workflow,we screened 167 extracts extracted from 36 medicinal fungi using optimized extraction methods.We assessed the antiviral effects of these extracts by measuring their ability to inhibit SARS‐CoV‐2 infection and receptor binding domain‐human angiotensin‐converting enzyme 2(RBD‐hACE2)binding in vitro.Following charge‐and size‐based characterization of the active compounds through filtration and chromatographic fractionation,mass spectrometry characterization of the fractionated compounds revealed that the active components are polysaccharides and determined their monosaccharide residue composition.Our findings provide new insights into the antiviral potential of natural products and their screening strategies and may contribute to the development of effective antiviral therapeutics against COVID‐19 and other diseases.

关键词： Medicinal fungi Natural products antiviral activity COVID‐19 Polysaccharides

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antiviral activity of mangiferin from the rhizome of Anemarrhena asphodeloides against herpes simplex virus type 1

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Asian Pacific Journal of Tropical Biomedicine 2023年第3期13卷 112-120页

作者： Wen-Da Wang Gang Chen Huzhou Hospital of Traditional Chinese Medicine Affiliated to Zhejiang University of Traditional Chinese Medicine Huzhou 313001China

Objective:To evaluate the antiviral activity of pure compounds against herpes simplex virus type 1(HSV-1)from the rhizome of Anemarrhena asphodeloides.Methods:Bioassay-guided isolation was conducted to separate the active compound and its chemical structure was elucidated by spectral analysis.In vitro antiviral efficacy of active compound was detected by Cell Counting Kit-8 assay,plaque reduction assay,and fluorescence observation.RT-PCR was used to determine the viral load and the cytokine-related gene expression after HSV-1 infection.In vivo study was also conducted to further determine antiviral efficacy of an active compound against HSV-1.Results:An active compound was isolated and elucidated as mangiferin.Mangiferin significantly inhibited the replication of HSV-1 in Vero cells with a half maximal inhibitory concentration(IC_(50))of 64.0 mg/L.Time-of-addition and time-of-removal assays demonstrated that mangiferin could effectively inhibit the replication of HSV-1 in the early stage(8 h).UL12,UL42,and UL54 gene expression levels of HSV-1 in the 64 mg/L mangiferin-treated group were markedly reduced as compared with the HSV-1 group(Pantiviral activity against HSV-1 in vitro and in vivo and could be a potential antiviral agent for HSV-1.

关键词： Anemarrhena asphodeloides Herpes simplex virus antiviral activity Mangiferin

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A bacterial protein Rhp-PSP inhibits plant viral proliferation through endoribonuclease activity

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Journal of Integrative Agriculture 2024年第6期23卷 1967-1978页

作者： Lijie Chen Qianze Peng Xiaohua Du Weixing Zhang Ju’e Cheng Shu’e Sun Deyong Zhang Pin Su Yong Liu Longping Branch College of BiologyHunan UniversityChangsha 410082China State Key Laboratory of Hybrid Rice/Institute of Plant Protection Hunan Academy of Agricultural SciencesChangsha 410125China

Plant virus causes massive crop losses globally.However,there is currently no effective measure to control plant viral disease.Previously,we identify an antiviral protein Rhp-PSP,produced by the bacterial Rhodopseudomonas palustris strain JSC-3b.In this study,we discover that the antiviral activity of Rhp-PSP relies on its endoribonuclease activity.Converting the arginine(R)residue at position 129 onto alanine(A)abolishs its endoribonuclease activity on coat protein(CP)RNA of tobacco mosaic virus(TMV),consequentially,compromises the antiviral activity of Rhp-PSP.Further investigation demonstrates that,the mutant Rhp-PSP^(R129A)is unable to form the homotrimer as the wild type,indicating the importance of quaternary junction for the endoribonuclease activity.Overexpression of Rhp-PSP in Nicotiana benthamiana significantly enhances the resistance against TMV of seedlings,while expression of Rhp-PSP^(R129A)did not,confirming that endoribonuclease activity is responsible for the antiviral activity of Rhp-PSP.In addition,foliar spray of Rhp-PSP solution on tomato and pepper plants significantly reduces the disease index of viral diseases,indicating that Rhp-PSP shows potential to develop antiviral agent in practice.

关键词： Rhodopseudomonas palustris Rhp-PSP tobacco mosaic virus endoribonuclease antiviral activity

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antiviral adsorption activity of porous silicon nanoparticles against different pathogenic human viruses

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Bioactive Materials 2022年第1期7卷 39-46页

作者： Liubov A.Osminkina Svetlana N.Agafilushkina Ekaterina A.Kropotkina Nikolay Yu Saushkin Ivan V.Bozhev Sergei S.Abramchuk Jeanne V.Samsonova Alexandra S.Gambaryan Lomonosov Moscow State University Physics DepartmentLeninskie Gory 1119991MoscowRussian Federation Institute for Biological Instrumentation of Russian Academy of Sciences 142290PushchinoMoscow RegionRussian Federation Chumakov Federal Scientific Center for Research and Development of Immune-and-Biological Products Russian Academy of Sciences108819MoscowRussian Federation Lomonosov Moscow State University Faculty of ChemistryLeninskie Gory 1119991MoscowRussian Federation Quantum Technology Center Lomonosov Moscow State UniversityPhysics DepartmentLeninskie Gory 1119991MoscowRussian Federation A.N.Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences Vavilova 28119991MoscowRussian Federation

New viral infections,due to their rapid spread,lack of effective antiviral drugs and vaccines,kill millions of people every year.The global pandemic SARS-CoV-2 in 2019-2021 has shown that new strains of viruses can widespread very quickly,causing disease and death,with significant socio-economic consequences.Therefore,the search for new methods of combating different pathogenic viruses is an urgent task,and strategies based on nanoparticles are of significant interest.This work demonstrates the antiviral adsorption(virucidal)efficacy of nanoparticles of porous silicon(PSi NPs)against various enveloped and non-enveloped pathogenic human viruses,such as Influenza A virus,Poliovirus,Human immunodeficiency virus,West Nile virus,and Hepatitis virus.PSi NPs sized 60 nm with the average pore diameter of 2 nm and specific surface area of 200 m^(2)/g were obtained by ball-milling of electrochemically-etched microporous silicon films.After interaction with PSi NPs,a strong suppression of the infectious activity of the virus-contaminated fluid was observed,which was manifested in a decrease in the infectious titer of all studied types of viruses by approximately 104 times,and corresponded to an inactivation of 99.99%viruses in vitro.This sorption capacity of PSi NPs is possible due to their microporous structure and huge specific surface area,which ensures efficient capture of virions,as confirmed by ELISA analysis,dynamic light scattering measurements and transmission electron microscopy images.The results obtained indicate the great potential of using PSi NPs as universal viral sorbents and disinfectants for the detection and treatment of viral diseases.

关键词： Pathogenic human viruses Porous silicon nanoparticles Virus antiviral activity Virucide

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Inhibition of hepatitis B virus via selective apoptosis modulation by Chinese patent medicine Liuweiwuling Tablet

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World Journal of Gastroenterology 2024年第13期30卷 1911-1925页

作者： Fei-Lin Ge Yan Yang Lan-Lan Si Yuan-Hua Li Meng-Zhen Cao Jun Wang Zhao-Fang Bai Zhi-Gang Ren Xiao-He Xiao Yan Liu Department of Chinese Medicine State Key Laboratory of Antiviral DrugsThe First Affiliated Hospital of Zhengzhou UniversityZhengzhou 450052Henan ProvinceChina The Fifth Medical Center of Chinese PLA General Hospital Beijing 100039China College of Traditional Chinese Medicine Chongqing Medical UniversityChongqing 400010China Beijing Key Laboratory of Emerging Infectious Diseases Peking University Ditan Teaching HospitalBeijing 100015China Department of Infectious Diseases State Key Laboratory of Antiviral Drugsthe First Affiliated Hospital of Zhengzhou UniversityZhengzhou 450052Henan ProvinceChina

BACKGROUND Liuweiwuling Tablet(LWWL)is a Chinese patent medicine approved for the treatment of chronic inflammation caused by hepatitis B virus(HBV)infection.Previous studies have indicated an anti-HBV effect of LWWL,specifically in terms of antigen inhibition,but the underlying mechanism remains unclear.AIM To investigate the potential mechanism of action of LWWL against HBV.METHODS In vitro experiments utilized three HBV-replicating and three non-HBV-replicating cell lines.The in vivo experiment involved a hydrodynamic injectionmediated mouse model with HBV replication.Transcriptomics and metabolomics were used to investigate the underlying mechanisms of action of LWWL.RESULTS In HepG2.1403F cells,LWWL(0.8 mg/mL)exhibited inhibitory effects on HBV DNA,hepatitis B surface antigen and pregenomic RNA(pgRNA)at rates of 51.36%,24.74%and 50.74%,respectively.The inhibition rates of LWWL(0.8mg/mL)on pgRNA/covalently closed circular DNA in HepG2.1403F,HepG2.2.15 and HepG2.A64 cells were 47.78%,39.51%and 46.74%,respectively.Integration of transcriptomics and metabolomics showed that the anti-HBV effect of LWWL was primarily linked to pathways related to apoptosis(PI3K-AKT,CASP8-CASP3 and P53 pathways).Apoptosis flow analysis revealed that the apoptosis rate in the LWWL-treated group was significantly higher than in the control group(CG)among HBV-replicating cell lines,including HepG2.2.15(2.92%±1.01%vs 6.68%±2.04%,P0.05),L02 cells(5.49%±0.80%vs 5.48%±1.01%,P>0.05)and LX2 cells(6.29%±1.54%vs 6.29%±0.88%,P>0.05).TUNEL staining revealed a significantly higher apoptosis rate in the LWWL-treated group than in the CG in the HBVreplicating mouse model,while no noticeable difference in apoptosis rates between the two groups was observed in the non-HBV-replicating mouse m

关键词： Hepatitis B virus Chinese patent medicine antiviral activity antiviral mechanism Selective apoptosis

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antiviral activity of Dual-acting Hydrocarbon-stapled Peptides against HIV-1 Predominantly Circulating in China

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Biomedical and Environmental Sciences 2017年第6期30卷 398-406页

作者： WANG Yan CURRELI Francesca XU Wei Si LI Zhen Peng KONG De Sheng REN Li HONG Kun Xue JIANG Shi Bo SHAO Yi Ming DEBNATH Asim K MA Li Ying State Key Laboratory of Infectious Disease Prevention and Control National Center for AIDS/STD Control and PreventionCollaborative Innovation Center for Diagnosis and Treatment of Infectious DiseasesChinese Center for Disease Control and PreventionBeijing 102206China State Key Laboratory of Infectious Disease Prevention and Control National Institute for Communicable Disease Control and PreventionCollaborative Innovation Center for Diagnosis and Treatment of Infectious DiseasesChinese Center for Disease Control and PreventionBeuhing 102206China Laboratory of Molecular Modeling and Drug Design Lindsley F.Kimball Research Institute of the New York Blood CenterNew York 10065USA Key Laboratory of Medical Molecular Virology of Ministries of Education and Health Shanghai Medical College and Institute of Medical MicrobiologyFudan UniversityShanghai 200032China

Objective New rationally designed i,i＋7-hydrocarbon-stapled peptides that target both HIV-1 assembly and entry have been shown to have antiviral activity against HIV-1 subtypes circulating in Europe and North America. Here, we aimed to evaluate the antiviral activity of these peptides against HIV-1 subtypes predominantly circulating in China. Methods The antiviral activity of three i,i＋7-hydrocarbon-stapled peptides, NYAD-36, NYAD-67, and NYAD-66, against primary HIV-1 CRF07_BC and CRFOI_AE isolates was evaluated in peripheral blood mononuclear cells （PI3MCs）. The activity against the CRF07_BC and CRF01_AE Env-pseudotyped viruses was analyzed in TZM-bl cells. Results We found that all the stapled peptides were effective in inhibiting infection by all the primary HIV-1 isolates tested, with 50% inhibitory concentration toward viral replication （ICso） in the low micromolar range. NYAD-36 and NYAD-67 showed better antiviral activity than NYAD-66 did. We further evaluated the sensitivity of CRF01_AE and CRF07_BC Env-pseudotyped viruses to these stapled peptides in a single-cycle virus infectivity assay. As observed with the primary isolates, the ICs0s were in the low micromolar range, and NYAD-66 was less effective than NYAD-36 and NYAD-67. Conclusion Hydrocarbon-stapled peptides appear to have broad antiviral activity against the predominant HIV-1 viruses in China. This finding may provide the impetus to the rational design of peptides for future antiviral therapy.

关键词： Hydrocarbon-stapled peptide HIV-1 CRF07 BC CRFOI_AE antiviral activity

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Design of Biologically Active Macromolecular Ligands and Their Luminescent Complexes with Terbium Ions

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Chinese Journal of Polymer Science 2024年第5期42卷 604-611,I0007页

作者： Tatiana N.Nekrasova Andrei I.Fischer Natalia A.Nesterova Anatoliy V.Dobrodumov Anzhelika V.Garshinina Olga D.Shuvaeva Natalya V.Zakharova Evgenii F.Panarin Institute of Macromolecular Compounds Russian Academy of Sciences31 Bolshoy pr.St Petersburg199004Russia Smorodintsev Research Institute of Influenza Russian Ministry of Health15/17 ul.prof.PopovaSt Petersburg197376Russia

Water-soluble copolymers of p-methacrylamidobenzoic acid(MABA)with neutral comonomers(N-vinylpyrrolidone(VP),N-methyl-N-vinylacetamide(MVAA),N-methacryloyl glucosamine(MAG))and anionic comononer sodium styrene sulfonate(NaSS)were synthesized by radical copolymerization.The interactions between the prepared copolymers and Tb^(3+)ions in aqueous solutions were studied;the significant influence of chemical structure of a comonomer on luminescence intensity of Tb^(3+)complexes with the copolymers was revealed.The luminescence intensity of Tb^(3+)complexes with the copolymers containing N-vinylamide units(VP,MVAA)is three times more intense than that observed for the complexes between Tb^(3+)and MAG-containing copolymers.In the case of NaSS-containing copolymers,the luminescence intensity is controlled by the values of binding constants between Tb^(3+)and MABA and the content of MABA units in a copolymer.The studied copolymers and their complexes with Tb^(3+)have low cytotoxicity and a pronounced antiviral activity against human respiratory syncytial virus.

关键词： Luminescence Water-soluble copolymers Lanthanide complexes antiviral activity Cytotoxicity

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Discovery of unusual phloroglucinol-triterpenoid adducts from Leptospermum scoparium and Xanthostemon chrysanthus by building blocks-based molecular networking

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Chinese Chemical Letters 2024年第6期35卷 353-357页

作者： Jinyan Zhang Fen Liu Qian Jin Xueyi Li Qiong Zhan Mu Chen Sisi Wang Zhenlong Wu Wencai Ye Lei Wang State Key Laboratory of Bioactive Molecules and Druggability Assessment Jinan UniversityGuangzhou 510632China Center for Bioactive Natural Molecules and Innovative Drugs and Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs ResearchJinan UniversityGuangzhou 510632China College of Pharmacy Jinan UniversityGuangzhou 510632China

The first phloroglucinol-triterpenoid hybrids,myrtphlotritins A-E(1-5),were rapidly recognized and isolated from two species of Myrtaceae by employing the building blocks-based molecular network(BBMN)strategy.Compounds 1-5 featured new carbon skeletons in which phloroglucinol derivatives were coupled with lupane-and dammarane-type triterpenoids through different linkage patterns.Their structures and absolute configurations were elucidated by comprehensive analysis of spectroscopic data and quantum chemical calculations.Biosynthetic pathways for compounds 1-5 were proposed on the basis of the coexisting precursors.Guided by the biogenetic pathways,the biomimetic synthesis of compound 1 was also achieved.Additionally,compounds 2,3,and 5 exhibited potent antiviral activities against herpes simplex virus type-1(HSV-1)infection,and compounds 2 and 5 displayed significant anti-inflammatory activities on RAW264.7 cells.

关键词： Phloroglucinol-triterpenoid adduct Myrtaceae Building blocks-based molecular network Biomimetic synthesis antiviral activity Anti-inflammatory activity

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antiviral activity of cepharanthine against severe acute respiratory syndrome coronavirus in vitro

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Chinese Medical Journal 2005年第6期118卷 493-496页

作者： ZHANGChuan-hai WANGYi-fei LIUXin-jian LUJia-hai QIANChui-wen WANZhuo-yue YANXin-ge ZHENGHuan-ying ZHANGMei-ying XIONGSheng LIJiu-xiang QIShu-yuan BiomedicalResearch＆DevelopmentCenter Ji-nanUniversityGuangzhou510630China DepartmentofChemistryandBiology WestAnhuiUniversityLu＇an237012China DepartmentofMedicalStatisticsandEpidemiology SchoolofPublicHealthSunYat-senUniversityGuangzhou510080China CenterforDiseaseControlandPreventionofGuangdongProvince Guangzhou510300China SouthChinaInstituteofBotany GraduateSchooloftheChineseAcademyofSciencesGuangzhou510650China

Severe acute respiratory syndrome(SARS) is the first severe viral epidemic we encountered his century,which once spread in more than thirty countriesin2003.1 The etiological agent of SARS has beenc onfirmed to be a novel coronavirus,namely SARS coronavirus(SARS-CoV),2,3 and the first outbreak of SARS has been successfully controlled world wide,but the identification of SARS-CoV isolated from wildanimals,the emergence of some sporadic SARS cases laterafter that outbreak,all suggest that the recurrence of such an epidemic is not unlikely in the future.In this case,development of SARS vaccines and specific drugs is undoubtedlyessential to the control and prevention from the possible outbreak.4,5

关键词： cepharanthine severe acute respiratory syndrome coronavirus antiviral activity

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High-Value-Added Utilization of Turpentine:Screening of Anti-Influenza Virus Agents fromβ-Pinene Derivatives

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Journal of Renewable Materials 2024年第1期12卷 45-56页

作者： Yiwen Li Hongyan Si Peng Wang Hai Luo Minggui Shen Xiaoping Rao Zhanqian Song Shibin Shang Zongde Wang Shengliang Liao East China Woody Fragrance and Flavor Engineering Research Center of National Forestry and Grassland Administration Camphor Engineering Research Center of National Forestry and Grassland AdministrationCollege of ForestryJiangxi Agricultural UniversityNanchang330045China Institute of Chemical Industry of Forestry Products China Academy of ForestryNational Engineering Laboratory for Biomass Chemical UtilizationKey and Open Laboratory of Forest Chemical EngineeringState Forestry AdministrationKey Laboratory of Biomass Energy and MaterialJiangsu ProvinceNanjing210042China College of Chemical Engineering Huaqiao UniversityXiamen361021China

Turpentine is a renewable and resourceful forest product.The deep processing and utilization of turpentine,particularly its primary componentβ-pinene,has garnered widespread attention.This study aimed to synthesize 40 derivatives ofβ-pinene,including nopinone,3-cyanopyridines of nopinone,myrtanyl acid,myrtanyl acylthioureas,and myrtanyl amides.We assessed the antiviral activities of theseβ-pinene derivatives against influenza virus A/Puerto Rico/8/34(H1N1)using the 3-(4,5-dimetylthiazol-2-yl)-2,5-diphenyltetrazolium bromide method.Theβ-pinene derivatives were used before and after cellular infection with the influenza virus to evaluate their preventive and therapeutic effects against the H1N1 virus.The results showed that only compound 10o exhibited a preventive effect against the H1N1 virus with a half-maximal inhibitory concentration(IC50)value of 47.6μmol/L.Among the compounds,4e,4i,and 4l demonstrated therapeutic effects against cellular infection,with compound 4e displaying the most potent therapeutic effect(IC50=17.5μmol/L),comparable to the positive control ribavirin.These findings indicated that certainβ-pinene derivatives exhibited in vitro antiviral activity against the H1N1 influenza A virus,warranting further investigation as potential anti-influenza agents.

关键词： antiviral activity β-pinene derivative 3-cyanopyridine influenza virus

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