{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,14]],"date-time":"2025-10-14T00:37:51Z","timestamp":1760402271376,"version":"build-2065373602"},"reference-count":58,"publisher":"MDPI AG","issue":"2","license":[{"start":{"date-parts":[[2022,1,10]],"date-time":"2022-01-10T00:00:00Z","timestamp":1641772800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Plants"],"abstract":"<jats:p>Human African trypanosomiasis is an endemic infectious disease caused by Trypanosoma brucei via the bite of tsetse-fly. Most of the drugs used for the treatment, e.g., Suramin, have shown several problems, including the high level of toxicity. Accordingly, the discovery of anti-trypanosomal drugs from natural sources has become an urgent requirement. In our previous study on the anti-trypanosomal potential of Euphorbia species, Euphorbia abyssinica displayed significant anti-trypanosomal activity. Therefore, a phytochemical investigation of the methanolic extract of E. abyssinica was carried out. Twelve compounds, including two triterpenes (1, 2); one sterol-glucoside (4); three ellagic acid derivatives (3, 9, 11); three gallic acid derivatives (5, 6, 10); and three flavonoids (7, 8, 12), were isolated. The structures of isolated compounds were determined through different spectroscopic techniques. Compound (10) was obtained for the first time from genus Euphorbia while all other compounds except compound (4), were firstly reported in E. abyssinica. Consequently, an in silico study was used to estimate the anti-trypanosomal activity of the isolated compounds. Several compounds displayed interesting activity where 1,6-di-O-galloyl-d-glucose (10) appeared as the most potent inhibitor of trypanosomal phosphofructokinase (PFK). Moreover, molecular dynamics (MD) simulations and ADMET calculations were performed for 1,6-di-O-galloyl-d-glucose. In conclusion, 1,6-di-O-galloyl-d-glucose revealed high binding free energy as well as desirable molecular dynamics and pharmacokinetic properties; therefore, it could be suggested for further in vitro and in vivo studies for trypanosomiasis.<\/jats:p>","DOI":"10.3390\/plants11020173","type":"journal-article","created":{"date-parts":[[2022,1,10]],"date-time":"2022-01-10T22:03:13Z","timestamp":1641852193000},"page":"173","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":5,"title":["Digalloyl Glycoside: A Potential Inhibitor of Trypanosomal PFK from Euphorbia abyssinica J.F. Gmel"],"prefix":"10.3390","volume":"11","author":[{"given":"Seham S.","family":"El-Hawary","sequence":"first","affiliation":[{"name":"Department of Pharmacognosy, Faculty of Pharmacy, Cairo University, Giza 12613, Egypt"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9683-4250","authenticated-orcid":false,"given":"Rabab","family":"Mohammed","sequence":"additional","affiliation":[{"name":"Department of Pharmacognosy, Faculty of Pharmacy, Beni-Suef University, Beni-Suef 62514, Egypt"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3674-5595","authenticated-orcid":false,"given":"Nadia M.","family":"Lithy","sequence":"additional","affiliation":[{"name":"Department of Pharmacognosy, Faculty of Pharmacy, Nahda University Beni-Suef, Beni-Suef 62521, Egypt"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Sameh Fekry","family":"AbouZid","sequence":"additional","affiliation":[{"name":"Department of Pharmacognosy, Faculty of Pharmacy, Beni-Suef University, Beni-Suef 62514, Egypt"},{"name":"Department of Pharmacognosy, Faculty of Pharmacy, Heliopolis University, Cairo 11785, Egypt"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0179-8398","authenticated-orcid":false,"given":"Mostafa A.","family":"Mansour","sequence":"additional","affiliation":[{"name":"Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Nahda University Beni-Suef, Beni-Suef 62521, Egypt"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Suliman A.","family":"Almahmoud","sequence":"additional","affiliation":[{"name":"Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, Qassim University, Buraidah 51452, Saudi Arabia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Bader","family":"Huwaimel","sequence":"additional","affiliation":[{"name":"Department of Pharmaceutical Chemistry, College of Pharmacy, University of Hail, Hail 34464, Saudi Arabia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7190-3974","authenticated-orcid":false,"given":"Elham","family":"Amin","sequence":"additional","affiliation":[{"name":"Department of Pharmacognosy, Faculty of Pharmacy, Beni-Suef University, Beni-Suef 62514, Egypt"},{"name":"Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, Qassim University, Buraidah 51452, Saudi Arabia"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2022,1,10]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"11280","DOI":"10.1021\/cr500197d","article-title":"Kinases as druggable targets in trypanosomatid protozoan parasites","volume":"114","author":"Merritt","year":"2014","journal-title":"Chem. Rev."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"88","DOI":"10.3389\/fmolb.2020.00088","article-title":"Identification of Alternative Allosteric Sites in Glycolytic Enzymes for Potential Use as Species-Specific Drug Targets","volume":"7","author":"Ayyildiz","year":"2020","journal-title":"Front. Mol. Biosci."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"1052","DOI":"10.1038\/s41467-021-21273-6","article-title":"Fast acting allosteric phosphofructokinase inhibitors block trypanosome glycolysis and cure acute African trypanosomiasis in mice","volume":"12","author":"McNae","year":"2021","journal-title":"Nat. Commun."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"75","DOI":"10.1007\/BF00230589","article-title":"A review of animal phosphofructokinase isozymes with an emphasis on their physiological role","volume":"52","author":"Dunaway","year":"1983","journal-title":"Mol. Cell. Biochem."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"1519","DOI":"10.1016\/j.jmb.2008.11.047","article-title":"The crystal structure of ATP-bound phosphofructokinase from Trypanosoma brucei reveals conformational transitions different from those of other phosphofructokinases","volume":"385","author":"McNae","year":"2009","journal-title":"J. Mol. Biol."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"28306","DOI":"10.1074\/jbc.M502403200","article-title":"Experimental and in silico analyses of glycolytic flux control in bloodstream form Trypanosoma brucei","volume":"280","author":"Albert","year":"2005","journal-title":"J. Biol. Chem."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"127","DOI":"10.1146\/annurev.mi.41.100187.001015","article-title":"Compartmentation of carbohydrate metabolism in trypanosomes","volume":"41","author":"Opperdoes","year":"1987","journal-title":"Annu. Rev. Microbiol."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"1185","DOI":"10.1016\/j.jmb.2006.10.019","article-title":"The first crystal structure of phosphofructokinase from a eukaryote: Trypanosoma brucei","volume":"366","author":"McNae","year":"2007","journal-title":"J. Mol. Biol."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"1255","DOI":"10.2174\/156802611795429167","article-title":"State of the art in African trypanosome drug discovery","volume":"11","author":"Nare","year":"2011","journal-title":"Curr. Top. Med. Chem."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"12","DOI":"10.1021\/ml400259d","article-title":"Identification of ML251, a potent inhibitor of T. brucei and T. cruzi phosphofructokinase","volume":"5","author":"Brimacombe","year":"2014","journal-title":"ACS Med. Chem. Lett."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"200","DOI":"10.1007\/s40506-017-0120-1","article-title":"Novel therapeutic targets for human African trypanosomiasis","volume":"9","author":"Girdhar","year":"2017","journal-title":"Curr. Treat. Options Infect. Dis."},{"key":"ref_12","doi-asserted-by":"crossref","unstructured":"Luisi, G., and Carradori, S. (2021). New Compounds for the Management of Trypanosoma brucei Infection. Topics in Medicinal Chemistry, Springer.","DOI":"10.1007\/7355_2021_126"},{"key":"ref_13","first-page":"1505","article-title":"Phytochemical and Antimicrobial Investigation of Latex from Euphorbia abyssinica Gmel","volume":"3","author":"Asres","year":"2008","journal-title":"Nat. Prod. Commun."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"291","DOI":"10.12705\/622.1","article-title":"Phylogenetics, morphological evolution, and classification of Euphorbia subgenus Euphorbia","volume":"62","author":"Dorsey","year":"2013","journal-title":"Taxon"},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"8579","DOI":"10.1021\/cr400541j","article-title":"Euphorbia Diterpenes: Isolation, Structure, Biological Activity, and Synthesis (2008\u20132012)","volume":"114","author":"Vasas","year":"2014","journal-title":"Chem. Rev."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"1095","DOI":"10.1016\/S0031-9422(97)01065-0","article-title":"Ingenane and lathyrane diterpenes from the latex of Euphorbia acrurensis","volume":"49","author":"Marco","year":"1998","journal-title":"Phytochemistry"},{"key":"ref_17","doi-asserted-by":"crossref","unstructured":"El-Hawary, S.S., Mohammed, R., Tawfike, A.F., Lithy, N.M., AbouZid, S.F., Amin, M.N., Abdelmohsen, U.R., and Amin, E. (2021). Cytotoxic activity and metabolic profiling of fifteen Euphorbia Species. Metabolites, 11.","DOI":"10.1038\/s41598-021-87695-w"},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"261","DOI":"10.1186\/s12936-019-2887-7","article-title":"Anti-malarial activity of the root extract of Euphorbia abyssinica (Euphorbiaceae) against Plasmodium berghei infection in mice","volume":"18","author":"Muluye","year":"2019","journal-title":"Malar. J."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"1295","DOI":"10.2174\/1389450120666190618114857","article-title":"Flavonoid-derived privileged scaffolds in anti-trypanosoma brucei drug discovery","volume":"20","author":"Boniface","year":"2019","journal-title":"Curr. Drug Targets"},{"key":"ref_20","doi-asserted-by":"crossref","unstructured":"Jabalia, N., Kumar, A., Kumar, V., and Rani, R. (2021). In Silico Approach in Drug Design and Drug Discovery: An Update. Innovations and Implementations of Computer Aided Drug Discovery Strategies in Rational Drug Design, Springer.","DOI":"10.1007\/978-981-15-8936-2_10"},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"106593","DOI":"10.1016\/j.bpc.2021.106593","article-title":"In silico drug discovery for a complex immunotherapeutic target-human c-Rel protein","volume":"276","author":"Beaurivage","year":"2021","journal-title":"Biophys. Chem."},{"key":"ref_22","unstructured":"Silakari, O., and Singh, P.K. (2020). Concepts and Experimental Protocols of Modelling and Informatics in Drug Design, Academic Press."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"54","DOI":"10.1186\/s43088-021-00140-9","article-title":"Anti-trypanosomal activity and DNA fingerprinting of fifteen Euphorbia species using ISSR and SCoT markers","volume":"10","author":"Lithy","year":"2021","journal-title":"Beni-Suef Univ. J. Basic Appl. Sci."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"170","DOI":"10.1016\/j.compbiolchem.2017.11.006","article-title":"Structure based virtual screening of the Ebola virus trimeric glycoprotein using consensus scoring","volume":"72","author":"Onawole","year":"2018","journal-title":"Comput. Biol. Chem."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"789","DOI":"10.1248\/cpb.40.789","article-title":"Triterpenoid Ketones from Lingnania chungii MoClure: Arborinone, friedelin and glutinone","volume":"40","author":"Akihisa","year":"1992","journal-title":"Chem. Pharm. Bull."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"378","DOI":"10.1002\/mrc.1260320615","article-title":"13C NMR spectroscopic data for glutinol and derivatives","volume":"32","author":"Olea","year":"1994","journal-title":"Magn. Reson. Chem."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"498","DOI":"10.1248\/cpb.47.498","article-title":"Five new taraxastane-type triterpenes from the aerial roots of Ficus microcarpa","volume":"47","author":"Kuo","year":"1999","journal-title":"Chem. Pharm. Bull."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"3419","DOI":"10.1016\/S0040-4020(01)87309-9","article-title":"Total assignment of 13C and 1H spectra of three isomeric triterpenol derivatives by 2D NMR: An investigation of the potential utility of 1H chemical shifts in structural investigations of complex natural products","volume":"42","author":"Reynolds","year":"1986","journal-title":"Tetrahedron"},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"251","DOI":"10.1111\/j.1744-7909.2005.00038.x","article-title":"Two new triterpenoids from the roots of Sanguisorba officinalis L.","volume":"47","author":"Zhang","year":"2005","journal-title":"J. Integr. Plant Biol."},{"key":"ref_30","doi-asserted-by":"crossref","unstructured":"Vo, T.K., Ta, Q.T.H., Chu, Q.T., Nguyen, T.T., and Vo, V.G. (2020). Anti-Hepatocellular-Cancer Activity Exerted by \u03b2-Sitosterol and \u03b2-Sitosterol-Glucoside from Indigofera zollingeriana Miq. Molecules, 25.","DOI":"10.3390\/molecules25133021"},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"1307","DOI":"10.1111\/jam.12328","article-title":"Isolation, characterization and mode of antimicrobial action against Vibrio cholerae of methyl gallate isolated from Acacia farnesiana","volume":"115","author":"Heredia","year":"2013","journal-title":"J. Appl. Microbiol."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"255","DOI":"10.1016\/j.dib.2018.12.008","article-title":"Nuclear magnetic resonance spectroscopy data of isolated compounds from Acacia farnesiana (L) Willd fruits and two esterified derivatives","volume":"22","year":"2019","journal-title":"Data Br."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"955","DOI":"10.1002\/cbdv.201400194","article-title":"Structure Activity Relationships of Antimicrobial Gallic Acid Derivatives from Pomegranate and Acacia Fruit Extracts against Potato Bacterial Wilt Pathogen","volume":"12","author":"Farag","year":"2015","journal-title":"Chem. Biodivers."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"3173","DOI":"10.3390\/molecules19033173","article-title":"Antibacterial effects of afzelin isolated from Cornus macrophylla on Pseudomonas aeruginosa, a leading cause of illness in immunocompromised individuals","volume":"19","author":"Lee","year":"2014","journal-title":"Molecules"},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"19","DOI":"10.1016\/j.sajb.2014.03.009","article-title":"Antimicrobial, antioxidant, anti-inflammatory activities and phytoconstituents of extracts from the roots of Dissotis thollonii Cogn. (Melastomataceae)","volume":"93","author":"Nono","year":"2014","journal-title":"S. Afr. J. Bot."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"1652","DOI":"10.1248\/cpb.31.1652","article-title":"Tannins and related compounds. X. Rhubarb (2): Isolation and structures of a glycerol gallate, gallic acid glucoside gallates, galloylglucoses and isolindleyin","volume":"31","author":"Nonaka","year":"1983","journal-title":"Chem. Pharm. Bull."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"2034","DOI":"10.3390\/molecules20022034","article-title":"Bin The synthesis and antitumor activity of twelve galloyl glucosides","volume":"20","author":"Li","year":"2015","journal-title":"Molecules"},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"105","DOI":"10.1002\/jccs.200100019","article-title":"Phenolic compounds from Formosan Euphorbia tirucalli","volume":"48","author":"Lin","year":"2001","journal-title":"J. Chin. Chem. Soc."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"4869","DOI":"10.1021\/jf980614b","article-title":"Antioxidative phenolic compounds from sage (Salvia officinalis)","volume":"46","author":"Wang","year":"1998","journal-title":"J. Agric. Food Chem."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"851","DOI":"10.1271\/bbb.90783","article-title":"Agrobacterium-Mediated Transformation of Euphorbia tirucalli Callus","volume":"74","author":"Uchida","year":"2010","journal-title":"Biosci. Biotechnol. Biochem."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"577","DOI":"10.1055\/s-2006-962820","article-title":"Further triterpenes from the stem bark of Euphorbia tirucalli","volume":"53","author":"Khan","year":"1987","journal-title":"Planta Med."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"650","DOI":"10.1080\/14786419.2014.980256","article-title":"A new phenylpropanoid from the roots of Euphorbia nematocypha","volume":"29","author":"Jia","year":"2015","journal-title":"Nat. Prod. Res."},{"key":"ref_43","first-page":"3969","article-title":"Chemical constituents of Euphorbia dracunculoides","volume":"39","author":"Wang","year":"2014","journal-title":"Zhongguo Zhong Yao Za Zhi= Zhongguo Zhongyao Zazhi= China J. Chin. Mater. Med."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"76","DOI":"10.32508\/stdjns.v2i5.781","article-title":"Chemical constituents of Euphorbia tirucalli L.","volume":"2","author":"Le","year":"2018","journal-title":"Sci. Technol. Dev. J. Sci."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"1137","DOI":"10.1248\/cpb.39.1137","article-title":"Tannins and Related Polyphenols of Euphorbiaceous Plants. VII. Tirucallins A, B and Euphorbin F, Monomeric and Dimeric Ellagitannins from Euphorbia tirucalli L.","volume":"39","author":"Yoshida","year":"1991","journal-title":"Chem. Pharm. Bull."},{"key":"ref_46","first-page":"2039","article-title":"Chemical constituents of Euphorbia royleana","volume":"44","author":"Yang","year":"2013","journal-title":"Chin. Tradit. Herb. Drugs"},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"799","DOI":"10.1016\/j.fitote.2010.04.012","article-title":"Anti-HBV active flavone glucosides from Euphorbia humifusa Willd","volume":"81","author":"Tian","year":"2010","journal-title":"Fitoterapia"},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"2229","DOI":"10.1590\/S0100-40422012001100025","article-title":"Anti-trypanosomal activity of 1, 2, 3, 4, 6-penta-O-galloyl-\u03b2-D-glucose isolated from Plectranthus barbatus Andrews (Lamiaceae)","volume":"35","author":"Santos","year":"2012","journal-title":"Quim. Nova"},{"key":"ref_49","doi-asserted-by":"crossref","unstructured":"Amisigo, C.M., Antwi, C.A., Adjimani, J.P., and Gwira, T.M. (2019). In vitro anti-trypanosomal effects of selected phenolic acids on Trypanosoma brucei. PLoS ONE, 14.","DOI":"10.1371\/journal.pone.0216078"},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"2066","DOI":"10.1007\/s11095-009-9932-0","article-title":"Anti-cancer, anti-diabetic and other pharmacologic and biological activities of penta-galloyl-glucose","volume":"26","author":"Zhang","year":"2009","journal-title":"Pharm. Res."},{"key":"ref_51","first-page":"108","article-title":"Anti-trypanosomal evaluation of Ximenia americana root bark and chromatographic-mass spectrometric profile","volume":"7","year":"2019","journal-title":"GSC Biol. Pharm. Sci."},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"2189","DOI":"10.1021\/acs.jcim.0c00057","article-title":"Improving protein-ligand docking results with high-throughput molecular dynamics simulations","volume":"60","author":"Guterres","year":"2020","journal-title":"J. Chem. Inf. Model."},{"key":"ref_53","first-page":"2338","article-title":"Cocarcinogenic Principles from the Seed Oil of Croton tiglium and from Other Euphorbiaceae","volume":"28","author":"Hecker","year":"1968","journal-title":"Cancer Res."},{"key":"ref_54","unstructured":"Markham, K.R. (1982). Techniques of Flavonoid Identification, Academic press."},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"1781","DOI":"10.1002\/jcc.20289","article-title":"Scalable molecular dynamics with NAMD","volume":"26","author":"Phillips","year":"2005","journal-title":"J. Comput. Chem."},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"3586","DOI":"10.1021\/jp973084f","article-title":"All-atom empirical potential for molecular modeling and dynamics studies of proteins","volume":"102","author":"Bashford","year":"1998","journal-title":"J. Phys. Chem. B"},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"1859","DOI":"10.1002\/jcc.20945","article-title":"CHARMM-GUI: A web-based graphical user interface for CHARMM","volume":"29","author":"Jo","year":"2008","journal-title":"J. Comput. Chem."},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"267","DOI":"10.1021\/ci300505n","article-title":"CHARMM-GUI Ligand Binder for absolute binding free energy calculations and its application","volume":"53","author":"Jo","year":"2013","journal-title":"J. Chem. Inf. Model."}],"container-title":["Plants"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/2223-7747\/11\/2\/173\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,13]],"date-time":"2025-10-13T13:27:12Z","timestamp":1760362032000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/2223-7747\/11\/2\/173"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2022,1,10]]},"references-count":58,"journal-issue":{"issue":"2","published-online":{"date-parts":[[2022,1]]}},"alternative-id":["plants11020173"],"URL":"https:\/\/doi.org\/10.3390\/plants11020173","relation":{},"ISSN":["2223-7747"],"issn-type":[{"type":"electronic","value":"2223-7747"}],"subject":[],"published":{"date-parts":[[2022,1,10]]}}}