Natural product-derived phytochemicals as potential agents against coronaviruses: A review

Virus Research - Tập 284 - Trang 197989 - 2020
Janice S. Mani1, Joel B. Johnson1, Jason C. Steel1, Daniel Broszczak2, Paul M. Neilsen1, Kerry B. Walsh1, Mani Naiker3,1
1School of Health, Medical and Applied Sciences, CQUniversity, Bruce Hwy, North Rockhampton, QLD, Australia
2Institute of Health & Biomedical Innovation (Q-Block), Queensland University of Technology, Kelvin Grove Campus, QLD, Australia
3Centre for Indigenous Health Equity Research, CQUniversity, Bruce Hwy, North Rockhampton, QLD, Australia

Tóm tắt

Từ khóa


Tài liệu tham khảo

Aldeghi, 2016, Accurate calculation of the absolute free energy of binding for drug molecules, Chem. Sci., 7, 207, 10.1039/C5SC02678D

Cassidy, 2019, Oxidative stress in alzheimer’s disease: a review on emergent natural polyphenolic therapeutics, Complement. Ther. Med., 102294

Chen, 2008, Toona sinensis Roem tender leaf extract inhibits SARS coronavirus replication, J. Ethnopharmacol., 120, 108, 10.1016/j.jep.2008.07.048

Chen, 2014, Sambucus nigra extracts inhibit infectious bronchitis virus at an early point during replication, BMC Vet. Res., 10, 24, 10.1186/1746-6148-10-24

Chen, 2017, Data resources for the computer-guided discovery of bioactive natural products, J. Chem. Inf. Model., 57, 2099, 10.1021/acs.jcim.7b00341

Cheng, 2006, Antiviral effects of saikosaponins on human coronavirus 229E in vitro, Clin. Exp. Pharmacol. Physiol., 33, 612, 10.1111/j.1440-1681.2006.04415.x

Chiang, 2003, Cytotoxicity and anti-hepatitis B virus activities of saikosaponins from Bupleurum species, Planta Med., 69, 705, 10.1055/s-2003-42797

Cho, 2013, Geranylated flavonoids displaying SARS-CoV papain-like protease inhibition from the fruits of Paulownia tomentosa, Bioorg. Med. Chem., 21, 3051, 10.1016/j.bmc.2013.03.027

Choi, 2009, Antiviral activity of quercetin 7-rhamnoside against porcine epidemic diarrhea virus, Antiviral Research., 81, 77, 10.1016/j.antiviral.2008.10.002

Chu, 2020, Molecular diagnosis of a novel coronavirus (2019-nCoV) causing an outbreak of pneumonia, Clin. Chem., 66, 549, 10.1093/clinchem/hvaa029

ClinicalTrials.gov, 2020

Cortegiani, 2020, A systematic review on the efficacy and safety of chloroquine for the treatment of COVID-19, J. Crit. Care, 10.1016/j.jcrc.2020.03.005

Covés-Datson, 2019, Inhibition of Ebola virus by a molecularly engineered banana lectin, PLoS Negl. Trop. Dis., 13, 10.1371/journal.pntd.0007595

Forli, 2016, Computational protein–ligand docking and virtual drug screening with the AutoDock suite, Nat. Protoc., 11, 905, 10.1038/nprot.2016.051

Ganjhu, 2015, Herbal plants and plant preparations as remedial approach for viral diseases, VirusDisease., 26, 225, 10.1007/s13337-015-0276-6

Gao, 2020, Breakthrough: chloroquine phosphate has shown apparent efficacy in treatment of COVID-19 associated pneumonia in clinical studies, Biosci. Trends, 14, 72, 10.5582/bst.2020.01047

Haiying, 2003, The curative effects of glycyrrhizin on patients with SARS, 18

Häkkinen, 1999, Content of the flavonols quercetin, myricetin, and kaempferol in 25 edible berries, J. Agric. Food Chem., 47, 2274, 10.1021/jf9811065

Han, 2007, Bioactivity-guided fractionation for anti-inflammatory and analgesic properties and constituents of Xanthium strumarium L, Phytomedicine, 14, 825, 10.1016/j.phymed.2007.01.010

Ho, 2007, Emodin blocks the SARS coronavirus spike protein and angiotensin-converting enzyme 2 interaction, Antiviral Res., 74, 92, 10.1016/j.antiviral.2006.04.014

Hoever, 2005, Antiviral activity of glycyrrhizic acid derivatives against SARS-coronavirus, J. Med. Chem., 48, 1256, 10.1021/jm0493008

Holshue, 2020, First case of 2019 novel coronavirus in the United States, N. Engl. J. Med., 382, 929, 10.1056/NEJMoa2001191

Hsieh, 2010, Synergistic antiviral effect of Galanthus nivalis agglutinin and nelfinavir against feline coronavirus, Antiviral Res., 88, 25, 10.1016/j.antiviral.2010.06.010

Huang, 2006, SARS coronavirus, but not human coronavirus NL63, utilizes cathepsin L to infect ACE2-expressing cells, J. Biol. Chem., 281, 3198, 10.1074/jbc.M508381200

Hui, 2020, The continuing 2019-nCoV epidemic threat of novel coronaviruses to global health — the latest 2019 novel coronavirus outbreak in Wuhan, China, Int. J. Infect. Dis., 91, 264, 10.1016/j.ijid.2020.01.009

Hwang, 2020, Characterization of a novel mannose-binding lectin with antiviral activities from red alga, Grateloupia chiangii, Biomolecules, 10, 333, 10.3390/biom10020333

Jackwood, 2010, Avian coronavirus infectious bronchitis virus susceptibility to botanical oleoresins and essential oils in vitro and in vivo, Virus Res., 149, 86, 10.1016/j.virusres.2010.01.006

Justesen, 2001, Composition of flavonoids in fresh herbs and calculation of flavonoid intake by use of herbs in traditional Danish dishes, Food Chem., 73, 245, 10.1016/S0308-8146(01)00114-5

Kaack, 1998, Interaction of vitamin C and flavonoids in elderberry (Sambucus nigra L.) during juice processing, Plant Foods Hum. Nutr., 52, 187, 10.1023/A:1008069422202

Kang, 2015, Jubanines F-J, cyclopeptide alkaloids from the roots of Ziziphus jujuba, Phytochemistry., 119, 90, 10.1016/j.phytochem.2015.09.001

Kaur, 2017, Recent synthetic and medicinal perspectives of tryptanthrin, Bioorg. Med. Chem., 25, 4533, 10.1016/j.bmc.2017.07.003

Keyaerts, 2007, Plant lectins are potent inhibitors of coronaviruses by interfering with two targets in the viral replication cycle, Antiviral Res., 75, 179, 10.1016/j.antiviral.2007.03.003

Khamitov, 2008, Antiviral activity of arbidol and its derivatives against the pathogen of severe acute respiratory syndrome in the cell cultures, Vopr. Virusol., 53, 9

Khan, 2019, Polyphenols in the treatment of autoimmune diseases, Autoimmun. Rev., 18, 647, 10.1016/j.autrev.2019.05.001

Kim, 2008, In vitro inhibition of coronavirus replications by the traditionally used medicinal herbal extracts, Cimicifuga rhizoma, Meliae cortex, Coptidis rhizoma, and Phellodendron cortex, J. Clin. Virol., 41, 122, 10.1016/j.jcv.2007.10.011

Kim, 2010, Medicinal herbal extracts of Sophorae radix, Acanthopanacis cortex, Sanguisorbae radix and Torilis fructus inhibit coronavirus replication in vitro, Antivir. Ther. (Lond.), 15, 697, 10.3851/IMP1615

Kim, 2014, Phenolic phytochemical displaying SARS-CoV papain-like protease inhibition from the seeds of Psoralea corylifolia, J. Enzyme Inhib. Med. Chem., 29, 59, 10.3109/14756366.2012.753591

Kim, 2019, Natural Bis-Benzylisoquinoline Alkaloids-Tetrandrine, Fangchinoline, and Cepharanthine, inhibit human coronavirus OC43 infection of MRC-5 human lung cells, Biomolecules, 9, 696, 10.3390/biom9110696

Kretzing, 2011, Dose-dependent emetic effects of the Amaryllidaceous alkaloid lycorine in beagle dogs, Toxicon., 57, 117, 10.1016/j.toxicon.2010.10.012

Kumaki, 2011, Inhibition of severe acute respiratory syndrome coronavirus replication in a lethal SARS-CoV BALB/c mouse model by stinging nettle lectin, Urtica dioica agglutinin, Antiviral Res., 90, 22, 10.1016/j.antiviral.2011.02.003

Lau, 2008, Immunomodulatory and anti-SARS activities of Houttuynia cordata, J. Ethnopharmacol., 118, 79, 10.1016/j.jep.2008.03.018

Lee, 2015, Porcine epidemic diarrhea virus infection: inhibition by polysaccharide from Ginkgo biloba exocarp and mode of its action, Virus Res., 195, 148, 10.1016/j.virusres.2014.09.013

Lelesius, 2019, In vitro antiviral activity of fifteen plant extracts against avian infectious bronchitis virus, BMC Vet. Res., 15, 178, 10.1186/s12917-019-1925-6

Letko, 2020, Functional assessment of cell entry and receptor usage for SARS-CoV-2 and other lineage B betacoronaviruses, Nat. Microbiol., 5, 562, 10.1038/s41564-020-0688-y

Li, 2005, Identification of natural compounds with antiviral activities against SARS-associated coronavirus, Antiviral Res., 67, 18, 10.1016/j.antiviral.2005.02.007

Li, 2011, Forsythoside a inhibits the avian infectious bronchitis virus in cell culture, Phytother. Res., 25, 338, 10.1002/ptr.4727

Li, 2019, In vitro antiviral activity of Griffithsin against porcine epidemic diarrhea virus, Virus Genes, 55, 174, 10.1007/s11262-019-01633-7

Lin, 2005, Anti-SARS coronavirus 3C-like protease effects of Isatis indigotica root and plant-derived phenolic compounds, Antiviral Res., 68, 36, 10.1016/j.antiviral.2005.07.002

Lin, 2014, Antiviral natural products and herbal medicines, J. Tradit. Complement. Med., 4, 24, 10.4103/2225-4110.124335

Lin, 2015, Saikosaponin b2 is a naturally occurring terpenoid that efficiently inhibits hepatitis C virus entry, J. Hepatol., 62, 541, 10.1016/j.jhep.2014.10.040

Ling, 2020, Traditional Chinese medicine is a resource for drug discovery against 2019 novel coronavirus (SARS-CoV-2), J. Integr. Med., 18, 87, 10.1016/j.joim.2020.02.004

Liu, 2005, SARS-CoV protease inhibitors design using virtual screening method from natural products libraries, J. Comput. Chem., 26, 484, 10.1002/jcc.20186

Loizzo, 2008, Phytochemical analysis and in vitro antiviral activities of the essential oils of seven Lebanon species, Chem. Biodivers., 5, 461, 10.1002/cbdv.200890045

Lu, 2020, Drug treatment options for the 2019-new coronavirus (2019-nCoV), Biosci. Trends, 14, 69, 10.5582/bst.2020.01020

Lu, 2015, Bat-to-human: spike features determining ‘host jump’of coronaviruses SARS-CoV, MERS-CoV, and beyond, Trends Microbiol., 23, 468, 10.1016/j.tim.2015.06.003

Lung, 2020, The potential chemical structure of anti-SARS-CoV-2 RNA-dependent RNA polymerase, J. Med. Virol., 92, 693, 10.1002/jmv.25761

Luo, 2009, Anti-SARS coronavirus 3C-like protease effects ofRheum palmatum L. extracts, Biosci. Trends, 3, 124

Luo, 2020, Can Chinese medicine be used for prevention of corona virus disease 2019 (COVID-19)? A review of historical classics, research evidence and current prevention programs, Chin. J. Integr. Med., 26, 243, 10.1007/s11655-020-3192-6

McCutcheon, 1995, Antiviral screening of British Columbian medicinal plants, J. Ethnopharmacol., 49, 101, 10.1016/0378-8741(95)90037-3

McDonagh, 2014, Identification and characterisation of small molecule inhibitors of feline coronavirus replication, Vet. Microbiol., 174, 438, 10.1016/j.vetmic.2014.10.030

Michaelis, 2011, Investigation of the influence of EPs(R) 7630, a herbal drug preparation from Pelargonium sidoides, on replication of a broad panel of respiratory viruses, Phytomedicine., 18, 384, 10.1016/j.phymed.2010.09.008

Michelow, 2011, High-dose mannose-binding lectin therapy for Ebola virus infection, J. Infect. Dis., 203, 175, 10.1093/infdis/jiq025

Miean, 2001, Flavonoid (myricetin, quercetin, kaempferol, luteolin, and apigenin) content of edible tropical plants, J. Agric. Food Chem., 49, 3106, 10.1021/jf000892m

Millet, 2016, Middle East respiratory syndrome coronavirus infection is inhibited by griffithsin, Antiviral Res., 133, 1, 10.1016/j.antiviral.2016.07.011

Mitchell, 2017, Antiviral lectins: selective inhibitors of viral entry, Antiviral Res., 142, 37, 10.1016/j.antiviral.2017.03.007

Müller, 2018, Broad-spectrum antiviral activity of the eIF4A inhibitor silvestrol against corona- and picornaviruses, Antiviral Res., 150, 123, 10.1016/j.antiviral.2017.12.010

Müller, 2020, Comparison of broad-spectrum antiviral activities of the synthetic rocaglate CR-31-B (−) and the eIF4A-inhibitor silvestrol, Antiviral Res., 175, 10.1016/j.antiviral.2020.104706

Newman, 2016, Natural products as sources of new drugs from 1981 to 2014, J. Nat. Prod., 79, 629, 10.1021/acs.jnatprod.5b01055

Nguyen, 2015, Antiviral cystine knot alpha-amylase inhibitors from Alstonia scholaris, J. Biol. Chem., 290, 31138, 10.1074/jbc.M115.654855

O’Keefe, 2010, Broad-spectrum in vitro activity and in vivo efficacy of the antiviral protein griffithsin against emerging viruses of the family Coronaviridae, J. Virol., 84, 2511, 10.1128/JVI.02322-09

Pang, 2020, Potential rapid diagnostics, vaccine and therapeutics for 2019 novel Coronavirus (2019-ncoV): a systematic review, J. Clin. Med., 9, 623, 10.3390/jcm9030623

Paraskevis, 2020, Full-genome evolutionary analysis of the novel corona virus (2019-nCoV) rejects the hypothesis of emergence as a result of a recent recombination event, Infect. Genet. Evol., 79, 10.1016/j.meegid.2020.104212

Park, 2012, Tanshinones as selective and slow-binding inhibitors for SARS-CoV cysteine proteases, Bioorg. Med. Chem., 20, 5928, 10.1016/j.bmc.2012.07.038

Park, 2017, Evaluation of polyphenols from Broussonetia papyrifera as coronavirus protease inhibitors, J. Enzyme Inhib. Med. Chem., 32, 504, 10.1080/14756366.2016.1265519

Pawlotsky, 2014, New hepatitis C virus (HCV) drugs and the hope for a cure: concepts in anti-HCV drug development, Semin. Liver Dis., 34, 022, 10.1055/s-0034-1371007

Petersen, 2006, Phase I safety, tolerability, and pharmacokinetic study of recombinant human mannan-binding lectin, J. Clin. Immunol., 26, 465, 10.1007/s10875-006-9037-z

Runfeng, 2020, Lianhuaqingwen exerts anti-viral and anti-inflammatory activity against novel coronavirus (SARS-CoV-2), Pharmacol. Res., 156, 10.1016/j.phrs.2020.104761

Ryu, 2010, Biflavonoids from Torreya nucifera displaying SARS-CoV 3CLpro inhibition, Bioorg. Med. Chem., 18, 7940, 10.1016/j.bmc.2010.09.035

Ryu, 2010, SARS-CoV 3CLpro inhibitory effects of quinone-methide triterpenes from Tripterygium regelii, Bioorg. Med. Chem. Lett., 20, 1873, 10.1016/j.bmcl.2010.01.152

Schoeman, 2019, Coronavirus envelope protein: current knowledge, Virol. J., 16, 69, 10.1186/s12985-019-1182-0

Shen, 2005, Bioactive pyranoxanthones from the roots of Calophyllum blancoi, Chem Pharm Bull (Tokyo)., 53, 244, 10.1248/cpb.53.244

Simmons, 2005, Inhibitors of cathepsin L prevent severe acute respiratory syndrome coronavirus entry, Proc. Natl. Acad. Sci., 102, 11876, 10.1073/pnas.0505577102

Sohrabi, 2020, World Health Organization declares global emergency: a review of the 2019 novel coronavirus (COVID-19), Int. J. Surg., 76, 71, 10.1016/j.ijsu.2020.02.034

Song, 2011, Quercetin 7-rhamnoside reduces porcine epidemic diarrhea virus replication via independent pathway of viral induced reactive oxygen species, Virol. J., 8, 460, 10.1186/1743-422X-8-460

Sudhan, 2015, Cathepsin L targeting in cancer treatment, Pharmacol. Ther., 155, 105, 10.1016/j.pharmthera.2015.08.007

Sundararajan, 2010, Influenza virus variation in susceptibility to inactivation by pomegranate polyphenols is determined by envelope glycoproteins, Antiviral Res., 88, 1, 10.1016/j.antiviral.2010.06.014

Theerawatanasirikul, 2020, In silico and in vitro analysis of small molecules and natural compounds targeting the 3CL protease of feline infectious peritonitis virus, Antiviral Res., 174, 10.1016/j.antiviral.2019.104697

Tian, 2009, Antioxidant and antimicrobial activities of consecutive extracts from Galla chinensis:the polarity affects the bioactivities, Food Chem., 113, 173, 10.1016/j.foodchem.2008.07.062

Tome-Carneiro, 2016, Polyphenol-based nutraceuticals for the prevention and treatment of cardiovascular disease: review of human evidence, Phytomedicine, 23, 1145, 10.1016/j.phymed.2015.10.018

Toney, 2004, Sabadinine: a potential non-peptide anti-severe acute-respiratory-syndrome agent identified using structure-aided design, J. Med. Chem., 47, 1079, 10.1021/jm034137m

Tsai, 2020, Antiviral action of tryptanthrin isolated from Strobilanthes cusia leaf against human coronavirus NL63, Biomolecules, 10, 10.3390/biom10030366

Ulasli, 2014, The effects of Nigella sativa (Ns), Anthemis hyalina (Ah) and Citrus sinensis (Cs) extracts on the replication of coronavirus and the expression of TRP genes family, Mol. Biol. Rep., 41, 1703, 10.1007/s11033-014-3019-7

Ushio, 1992, Inactivation of measles virus and herpes simplex virus by saikosaponin d, Planta Med., 58, 171, 10.1055/s-2006-961422

Wan, 2020, Clinical features and treatment of COVID-19 patients in Northeast Chongqing, J. Med. Virol., 10.1002/jmv.25783

Wang, 2003, Screening of traditional Chinese remedies for SARS treatment, Zhongguo Zhong Yao Za Zhi, 28, 484

Wang, 2007, Virtual screening for finding natural inhibitor against cathepsin-L for SARS therapy, Amino Acids, 33, 129, 10.1007/s00726-006-0403-1

Wang, 2009, Anti-hepatitis B virus activity of chlorogenic acid, quinic acid and caffeic acid in vivo and in vitro, Antiviral Res., 83, 186, 10.1016/j.antiviral.2009.05.002

Wang, 2020, Remdesivir and chloroquine effectively inhibit the recently emerged novel coronavirus (2019-nCoV) in vitro, Cell Res., 30, 269, 10.1038/s41422-020-0282-0

Wen, 2011, Traditional Chinese medicine herbal extracts of Cibotium barometz, Gentiana scabra, Dioscorea batatas, Cassia tora, and Taxillus chinensis inhibit SARS-CoV replication, J. Tradit. Complement. Med., 1, 41, 10.1016/S2225-4110(16)30055-4

Weng, 2019, Antiviral activity of Sambucus formosana Nakai ethanol extract and related phenolic acid constituents against human coronavirus NL63, Virus Res., 273, 10.1016/j.virusres.2019.197767

Wigmore, 2016, Antimicrobial activity of extracts from native plants of temperate Australia, Pharmacogn. Commun., 6, 80, 10.5530/pc.2016.2.5

Wittemer, 2005, Bioavailability and pharmacokinetics of caffeoylquinic acids and flavonoids after oral administration of Artichoke leaf extracts in humans, Phytomedicine., 12, 28, 10.1016/j.phymed.2003.11.002

World Health Organization, 2019

Wu, 2020, Genome composition and divergence of the novel coronavirus (2019-nCoV) originating in China, Cell Host Microbe, 27, 325, 10.1016/j.chom.2020.02.001

Wu, 2020, Analysis of therapeutic targets for SARS-CoV-2 and discovery of potential drugs by computational methods, Acta Pharm. Sin. B, 10.1016/j.apsb.2020.02.008

Yang, 2007, Bioactive coumarins from Boenninghausenia sessilicarpa, J. Asian Nat. Prod. Res., 9, 59, 10.1080/10286020500382397

Yang, 2010, Anti-infectious bronchitis virus (IBV) activity of 1,8-cineole: effect on nucleocapsid (N) protein, J. Biomol. Struct. Dyn., 28, 323, 10.1080/07391102.2010.10507362

Yang, 2011, Comparative anti-infectious bronchitis virus (IBV) activity of (-)-pinene: effect on nucleocapsid (N) protein, Molecules, 16, 1044, 10.3390/molecules16021044

Yang, 2020, Traditional chinese medicine in the treatment of patients infected with 2019-New coronavirus (SARS-CoV-2): a review and perspective, Int. J. Biol. Sci., 16, 1708, 10.7150/ijbs.45538

Yang, 2020, The deadly coronaviruses: the 2003 SARS pandemic and the 2020 novel coronavirus epidemic in China, J. Autoimmun., 109, 10.1016/j.jaut.2020.102434

Yao, 2020, A systematic review of lopinavir therapy for SARS coronavirus and MERS coronavirus–A possible reference for coronavirus Disease‐19 treatment option, J. Med. Virol., 92, 556, 10.1002/jmv.25729

Yi, 2004, Small molecules blocking the entry of severe acute respiratory syndrome coronavirus into host cells, J. Virol., 78, 11334, 10.1128/JVI.78.20.11334-11339.2004

Yin, 2011, In vitro and in vivo effects of Houttuynia cordata on infectious bronchitis virus, Avian Pathol., 40, 491, 10.1080/03079457.2011.605107

Yook, 2010, Antioxidative and antiviral properties of flowering cherry fruits (Prunus serrulata L. Var, spontanea). Am J Chin Med., 38, 937, 10.1142/S0192415X10008366

Yu, 2012, Identification of myricetin and scutellarein as novel chemical inhibitors of the SARS coronavirus helicase, nsP13, Bioorg. Med. Chem. Lett., 22, 4049, 10.1016/j.bmcl.2012.04.081

Zhang, 2020, In silico screening of Chinese herbal medicines with the potential to directly inhibit 2019 novel coronavirus, J. Integr. Med., 18, 152, 10.1016/j.joim.2020.02.005

Zhao, 2016, Scutellaria baicalensis, the golden herb from the garden of Chinese medicinal plants, Sci. Bull. (Beijing), 61, 1391, 10.1007/s11434-016-1136-5

Zhao, 2019, Saikosaponin b2 enhances the hepatotargeting effect of anticancer drugs through inhibition of multidrug resistance-associated drug transporters, Life Sci., 231, 10.1016/j.lfs.2019.116557

Zhuang, 2009, Procyanidins and butanol extract of Cinnamomi Cortex inhibit SARS-CoV infection, Antiviral Res., 82, 73, 10.1016/j.antiviral.2009.02.001