{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T01:08:55Z","timestamp":1760058535487,"version":"build-2065373602"},"reference-count":81,"publisher":"MDPI AG","issue":"8","license":[{"start":{"date-parts":[[2025,4,10]],"date-time":"2025-04-10T00:00:00Z","timestamp":1744243200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100006769","name":"Russian Science Foundation","doi-asserted-by":"publisher","award":["23-24-00310","23-14-00383"],"award-info":[{"award-number":["23-24-00310","23-14-00383"]}],"id":[{"id":"10.13039\/501100006769","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["IJMS"],"abstract":"<jats:p>The genus Spiraea is well represented in the Russian flora. Several phytochemical and bioactivity studies, completed so far with several individual species of this genus, indicate young Spiraea shoots as a promising source of pharmaceutically and nutraceutically active natural products. Therefore, a broad-scale phytochemical analysis of shoot extracts from multiple Russian Spiraea species (i.e., profiling of secondary metabolites and assignment of their structures), complemented with comprehensive activity screening, might give access to valuable information on the structure\u2013activity relationship (SAR) of their constituents. However, despite a lot of phytochemical and bioactivity information on individual species being available, these data are mostly fragmentary and do not allow for building a general picture, and in-depth comprehensive studies are still missing. Therefore, to fill this gap, here, we present a comprehensive metabolite profiling study accomplished with 15 of the most widely spread Russian Spiraea species, which was complemented with appropriate bioactivity screening of their first-year shoot alcoholic extracts. A chromatography\u2013mass spectrometric (LC-MS) analysis revealed 33 major constituents of the shoot isolates, which were dominated by flavonoids (quercetin and kaempferol derivatives) and hydroxycinnamic acids (caffeic, ferulic, and coumaric acid derivatives). Their relative quantification indicated that most of the identified major components were distributed among all of the studied extracts with minimal overlap in their composition and relative abundance. The antioxidant activity screening revealed the high efficiency of all of the extracts as potential redox protectors, acting at the levels of radical scavenging (DPPH assay) and quenching cation radicals (TEAC assay) and superoxide anion radicals (NBT assay). Screening the antiviral and antimicrobial activity of the same extracts revealed significant antiviral activity at a concentration of 2 \u00b5g\/mL, and high (MIC &lt; 1 mg\/mL) or moderate (1 mg\/mL \u2264 MIC \u2264 4 mg\/mL) antibacterial activity against Gram-positive and Gram-negative strains. The structures responsible for the manifestation of the studied types of activity were tentatively assigned using a bioinformatics-based strategy. This analysis revealed the most bioactive Spiraea species that might be promising for further in-depth phytochemical analysis and evaluations of their structure\u2013activity relationships (SARs). In this context, we consider S. humilis, which simultaneously showed antioxidant, antimicrobial, and antiviral activity; S. media, with marked antioxidant, antimicrobial, and cytotoxic properties; S. ussuriensis, a strong antioxidant and cytotoxic species; and S. trilobata, with a combination of antioxidant and antiviral properties.<\/jats:p>","DOI":"10.3390\/ijms26083587","type":"journal-article","created":{"date-parts":[[2025,4,10]],"date-time":"2025-04-10T10:47:41Z","timestamp":1744282061000},"page":"3587","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Biological Potential of Methanol Extracts from Plants of the Genus Spiraea Spreading in Russia"],"prefix":"10.3390","volume":"26","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-7836-5785","authenticated-orcid":false,"given":"Anastasia","family":"Orlova","sequence":"first","affiliation":[{"name":"Laboratory of Analytical Biochemistry and Biotechnology, K.A. Timiryazev Institute of Plant Physiology Russian Academy of Science, 35 Botanicheskaya Str., 127276 Moscow, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7318-8628","authenticated-orcid":false,"given":"Alena","family":"Soboleva","sequence":"additional","affiliation":[{"name":"Laboratory of Analytical Biochemistry and Biotechnology, K.A. Timiryazev Institute of Plant Physiology Russian Academy of Science, 35 Botanicheskaya Str., 127276 Moscow, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Elena","family":"Tsvetkova","sequence":"additional","affiliation":[{"name":"Department of Biochemistry, St. Petersburg State University, 7-9-11 University Emb., 199034 St. Petersburg, Russia"},{"name":"Department of General Pathology and Pathological Physiology, Institute of Experimental Medicine, 12 Acad. Pavlov Street, 197022 St. Petersburg, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9345-0240","authenticated-orcid":false,"given":"Svetlana","family":"Silinskaia","sequence":"additional","affiliation":[{"name":"Laboratory of Analytical Biochemistry and Biotechnology, K.A. Timiryazev Institute of Plant Physiology Russian Academy of Science, 35 Botanicheskaya Str., 127276 Moscow, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Yana L.","family":"Esaulkova","sequence":"additional","affiliation":[{"name":"The Laboratory of Experimental Virology, St. Petersburg Pasteur Institute, 14 Mira Str., 197101 St. Petersburg, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1880-0108","authenticated-orcid":false,"given":"Tatiana N.","family":"Veklich","sequence":"additional","affiliation":[{"name":"Botany Laboratory, Amur Branch of Botanical Garden-Institute of the Far Eastern Branch Russian Academy of Science (AB BGI FEB RAS), Ignatievskoe Road, 2km, 675000 Blagoveshchensk, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5224-3771","authenticated-orcid":false,"given":"Vladimir V.","family":"Zarubaev","sequence":"additional","affiliation":[{"name":"The Laboratory of Experimental Virology, St. Petersburg Pasteur Institute, 14 Mira Str., 197101 St. Petersburg, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Anna A.","family":"Khakulova","sequence":"additional","affiliation":[{"name":"Chemical Analysis and Materials Research Core Facility Center, Research Park, Saint-Petersburg State University, 199034 St. Petersburg, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0010-8620","authenticated-orcid":false,"given":"Ilya R.","family":"Akberdin","sequence":"additional","affiliation":[{"name":"Department of Computational Biology, Sirius University, 1 Olimpiyskiy Avenue, 354340 Sochi, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Semyon K.","family":"Kolmykov","sequence":"additional","affiliation":[{"name":"Department of Computational Biology, Sirius University, 1 Olimpiyskiy Avenue, 354340 Sochi, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Vera A.","family":"Kostikova","sequence":"additional","affiliation":[{"name":"Laboratory of Phytochemistry, Central Siberian Botanical Garden of Siberian Branch of Russian Academy of Sciences (CSBG SB RAS), 101 Zolotodolinskaya Str., 630090 Novosibirsk, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Andrej","family":"Frolov","sequence":"additional","affiliation":[{"name":"Laboratory of Analytical Biochemistry and Biotechnology, K.A. Timiryazev Institute of Plant Physiology Russian Academy of Science, 35 Botanicheskaya Str., 127276 Moscow, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2025,4,10]]},"reference":[{"doi-asserted-by":"crossref","unstructured":"Godlewska-\u017by\u0142kiewicz, B., \u015awis\u0142ocka, R., Kalinowska, M., Golonko, A., \u015awiderski, G., Arciszewska, \u017b., Nalewajko-Sieliwoniuk, E., Naumowicz, M., and Lewandowski, W. (2020). Biologically Active Compounds of Plants: Structure-Related Antioxidant, Microbiological and Cytotoxic Activity of Selected Carboxylic Acids. Materials, 13.","key":"ref_1","DOI":"10.3390\/ma13194454"},{"doi-asserted-by":"crossref","unstructured":"Olender, D., \u017bwawiak, J., and Zaprutko, L. (2018). Multidirectional Efficacy of Biologically Active Nitro Compounds Included in Medicines. Pharmaceuticals, 11.","key":"ref_2","DOI":"10.3390\/ph11020054"},{"doi-asserted-by":"crossref","unstructured":"Sinha, D., Odoh, U.E., Ganguly, S., Muhammad, M., Chatterjee, M., Chikeokwu, I., and Egbuna, C. (2023). Phytochemistry, History, and Progress in Drug Discovery. Phytochemistry, Computational Tools and Databases in Drug Discovery, Elsevier.","key":"ref_3","DOI":"10.1016\/B978-0-323-90593-0.00001-0"},{"doi-asserted-by":"crossref","unstructured":"Bender, O., Llorent-Mart\u00ednez, E.J., Zengin, G., Mollica, A., Ceylan, R., Molina-Garcia, L., Fern\u00e1ndez-de C\u00f3rdova, M.L., and Atalay, A. (2018). Integration of in vitro and in silico perspectives to explain chemical characterization, biological potential and anticancer effects of Hypericum salsugineum: A pharmacologically active source for functional drug formulations. PLoS ONE, 13.","key":"ref_4","DOI":"10.1371\/journal.pone.0197815"},{"unstructured":"(2021, May 01). The Plant List. Version 1.1. Available online: https:\/\/www.theplantlist.org.","key":"ref_5"},{"unstructured":"Komarov, V.L., and Yuzepchuk, S.V. (1971). Sorbaria. A.Br. Flora of the U.S.S.R., Vol. 4, Department of Commerce, U.S. Virginia.","key":"ref_6"},{"unstructured":"Vstovskaya, T.N., and Koropachinsky, I.Y. (2005). Woody Plants of the Central Siberian Botanical Garden, SB RAS Publishing House, Geo Branch. (In Russian).","key":"ref_7"},{"unstructured":"Baikov, K.S. (2012). Conspectus Florae Rossiae Asiaticae: Plantae Vasculares, Publishing House of the Siberian Branch of the Russian Academy of Sciences. (In Russian).","key":"ref_8"},{"unstructured":"Mayevsky, P.F. (2006). Flora of the Middle Zone of the European Part of Russia, Association of Scientific Publications KMK. [10th ed.].","key":"ref_9"},{"unstructured":"Sokolov, S.Y. (1954). Trees and Shrubs of the USSR\u2014Native, Cultivated or Promising for Introduction, Akademija Nauk SSSR. (In Russian).","key":"ref_10"},{"key":"ref_11","first-page":"47","article-title":"Spiraea Linnaeus","volume":"Volume 9","author":"Wu","year":"2003","journal-title":"Flora of China"},{"unstructured":"Zhang, X.S., and Wang, B.D. (1986). Chinese Medicine Dictionary, Shanghai Science and Technology Publishing House.","key":"ref_12"},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"1227","DOI":"10.1248\/cpb.52.1227","article-title":"New neolignans from Spiraea formosana","volume":"52","author":"Wu","year":"2004","journal-title":"Chem. Pharm. Bull."},{"key":"ref_14","first-page":"699","article-title":"Ethanobotanical studies on useful trees and shrubs of Haramosh and Bugrote valleys, in Gilgit northern area of Pakistan","volume":"39","author":"Khan","year":"2007","journal-title":"Pak. J. Bot."},{"unstructured":"Wu, Z.Y. (1984). Index Florae Yunnannensis (Tomus I), The People\u2019s Publishing House.","key":"ref_15"},{"unstructured":"Xie, Z.W. (1996). Quanguo Zhongcaoyao Huibian (A Collection of Chinese Herbal Drugs), People\u2019s Hygenic Publishing House. [2nd ed.].","key":"ref_16"},{"unstructured":"Lavrenov, V.K., and Lavrenova, G.V. (1999). Complete Encyclopedia of Medicinal Plants, Olma-Press. (In Russian).","key":"ref_17"},{"unstructured":"Batorova, S.M. (2013). Guide to Traditional Tibetan Medicinal Plants, Nauka. (In Russian).","key":"ref_18"},{"doi-asserted-by":"crossref","unstructured":"Lee, B.W., Ha, J.H., Shin, H.G., Jeong, S.H., Jeon, D.B., Kim, J.H., Park, J.Y., Kwon, H.J., Jung, K., and Lee, W.S. (2020). Spiraea prunifolia var. simpliciflora attenuates oxidative stress and inflammatory responses in a murine model of lipopolysaccharide-induced acute lung injury and TNF-stimulated NCI-H292 cells. Antioxidants, 9.","key":"ref_19","DOI":"10.3390\/antiox9030198"},{"doi-asserted-by":"crossref","unstructured":"Kostikova, V.A., Petrova, N.V., Shaldaeva, T.M., Koval, V.V., and Chernonosov, A.A. (2023). Non-Targeted Screening of Metabolites in Aqueous-Ethanol Extract from Spiraea hypericifolia (Rosaceae) Using LC-HRMS. Int. J. Mol. Sci., 24.","key":"ref_20","DOI":"10.3390\/ijms241813872"},{"key":"ref_21","first-page":"81","article-title":"Antioxidant and antimicrobial activity of seed from plants of the Mississippi river basin","volume":"2","author":"Borchardt","year":"2008","journal-title":"J. Med. Plants Res."},{"key":"ref_22","first-page":"59","article-title":"Antibacterial effects of S-(-)-tulipalin B isolated from Spiraea thunbergii Sieb. on Escherichia coli, major food borne pathogenic microorganism","volume":"2","author":"Lee","year":"2008","journal-title":"J. Med. Plants Res."},{"unstructured":"Kong, Q. (2014). Application of Spiraea alpina Extract in Preparing Anticancer Drugs. (103585310 (CN)), Chinese Patent, (In Chinese).","key":"ref_23"},{"doi-asserted-by":"crossref","unstructured":"Kaidash, O.A., Kostikova, V.A., Udut, E.V., Shaykin, V.V., and Kashapov, D.R. (2022). Extracts of Spiraea hypericifolia L. and Spiraea crenata L.: The phenolic profile and biological activities. Plants, 11.","key":"ref_24","DOI":"10.3390\/plants11202728"},{"unstructured":"Mirovich, V.M., Krivosheev, I.M., Gordeeva, V.V., and Tsyrenzhapov, A.V. (2013). Method for Producing Agent Possessing Anti-Inflammatory, Diuretic and Antioxidant Activity. (RU 2542493C1), Russian Patent, (In Russian).","key":"ref_25"},{"key":"ref_26","first-page":"335","article-title":"Anti-inflammatory and antioxidant effects of Spiraea prunifolia Sieb. et Zucc. var. simpliciflora Nakai in RAW 264.7 cells","volume":"30","author":"Sim","year":"2017","journal-title":"Korean J. Plant Resour."},{"key":"ref_27","first-page":"69","article-title":"Isolation, absolute configuration and bioactivities of megastigmanes or C13 isonorterpinoides","volume":"3","author":"Rao","year":"2017","journal-title":"Chem. Int."},{"doi-asserted-by":"crossref","unstructured":"Kostikova, V.A., and Petrova, N.V. (2021). Phytoconstituents and bioactivity of plants of the genus Spiraea L. (Rosaceae): A review. Int. J. Mol. Sci., 22.","key":"ref_28","DOI":"10.3390\/ijms222011163"},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"107772","DOI":"10.1016\/j.ympev.2023.107772","article-title":"A clue to the evolutionary history of modern East Asian flora: Insights from phylogeography and diterpenoid alkaloid distribution pattern of the Spiraea japonica complex","volume":"184","author":"Luo","year":"2023","journal-title":"Mol. Phylogenet. Evol."},{"doi-asserted-by":"crossref","unstructured":"Orlova, A., Kysil, E., Tsvetkova, E., Meshalkina, D., Whaley, A., Whaley, A.O., Laub, A., Francioso, A., Babich, O., and Wessjohann, L.A. (2022). Phytochemical Characterization of Water Avens (Geum rivale L.) Extracts: Structure Assignment and Biological Activity of the Major Phenolic Constituents. Plants, 11.","key":"ref_30","DOI":"10.3390\/plants11212859"},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"100","DOI":"10.1002\/hlca.201100214","article-title":"Flavonoid constituents from Spiraea brahuica","volume":"95","author":"Mughal","year":"2012","journal-title":"Helv. Chim. Acta"},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"1123","DOI":"10.1002\/hlca.201300402","article-title":"A new megastigmane glucoside and three new flavonoid glycosides from Spiraea prunifolia var","volume":"97","author":"Yean","year":"2014","journal-title":"simpliciflora. Helv. Chim. Acta"},{"key":"ref_33","first-page":"2806","article-title":"Chemical constituents from Spiraea salicifolia","volume":"47","author":"Yan","year":"2016","journal-title":"Chin. Tradit. Herb. Drugs"},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"195","DOI":"10.1002\/jccs.197700032","article-title":"Triterpenoids and some other constituents from Spiraeae formosana","volume":"24","author":"Chou","year":"1977","journal-title":"J. Chin. Chem. Soc."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"841","DOI":"10.1016\/S0040-4020(01)92480-9","article-title":"Studies in sesquiterpenes\u2014XLVII: Cis- and trans-atlantones from Cedrus deodara loud","volume":"27","author":"Pande","year":"1971","journal-title":"Tetrahedron"},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"440","DOI":"10.1007\/BF00571237","article-title":"Flavones and their 5-glycosides from Spiraea hypericifolia","volume":"11","author":"Chumbalov","year":"1975","journal-title":"Chem. Nat. Compd."},{"key":"ref_37","first-page":"138","article-title":"Polyhenolic compounds of Spiraea crenata","volume":"4","author":"Paris","year":"1970","journal-title":"Plant Med. Phytother."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"133","DOI":"10.1002\/ardp.19562890305","article-title":"\u00dcber die flavonglykoside der gattungen Filipendula und Spiraea","volume":"289","author":"Endres","year":"1956","journal-title":"Arch. Pharm."},{"key":"ref_39","first-page":"15","article-title":"Chemotaxonomic study of Spiraea aemiliana compared to the closely species S. betulifolia and S. beauverdiana","volume":"5","author":"Kostikova","year":"2019","journal-title":"Acta Biol. Sib."},{"unstructured":"Krivosheev, I.M. (2014). Pharmacognostic Study of Spiraea salicifolia L. Growing in Eastern Siberia. [Ph.D. Thesis, Irkutsk State Medical University]. (In Russian).","key":"ref_40"},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"108","DOI":"10.14258\/turczaninowia.18.4.14","article-title":"Phenolic compounds of representatives of sect. Glomerati of genus Spiraea L. of the flora of Siberia","volume":"18","author":"Karpova","year":"2015","journal-title":"Turczaninowia"},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"1467","DOI":"10.1016\/j.phytochem.2009.07.013","article-title":"Hemiterpene glucosides and other constituents from Spiraea canescens","volume":"70","author":"Choudhary","year":"2009","journal-title":"Phytochemistry"},{"key":"ref_43","first-page":"104","article-title":"The study of chemical composition of Spiraea salicifolia L. overground organs by Highly Effective Liquid Chromatography method","volume":"2","author":"Krivosheev","year":"2012","journal-title":"Sib. Med. J."},{"key":"ref_44","first-page":"87","article-title":"Phenolic composition and antioxidant properties of Spiraea nipponica","volume":"5","author":"Keskin","year":"2019","journal-title":"Int. J. Sci. Technol. Res."},{"key":"ref_45","first-page":"145","article-title":"Seasonal dynamics of the composition of phenolic compounds of the leaves of Spiraea media var","volume":"3","author":"Karpova","year":"2014","journal-title":"sericea (Turcz.) Regel. Chem. Plant Raw Mater."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"95","DOI":"10.1111\/j.1095-8339.1962.tb00890.x","article-title":"The phenolic constituents of plants and their taxonomic significance","volume":"58","year":"1962","journal-title":"Bot. J. Linn. Soc."},{"key":"ref_47","first-page":"178","article-title":"Phenolic compounds from leaves of Spiraea salicifolia","volume":"27","author":"Ahn","year":"1996","journal-title":"Korean J. Pharmacogn."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"1144","DOI":"10.1515\/CCLM.2003.177","article-title":"Oxidative Stress in Diabetes","volume":"41","author":"Piconi","year":"2003","journal-title":"Clin. Chem. Lab. Med."},{"doi-asserted-by":"crossref","unstructured":"Teleanu, D.M., Niculescu, A.-G., Lungu, I.I., Radu, C.I., Vlad\u00e2cenco, O., Roza, E., Cost\u0103chescu, B., Grumezescu, A.M., and Teleanu, R.I. (2022). An Overview of Oxidative Stress, Neuroinflammation, and Neurodegenerative Diseases. Int. J. Mol. Sci., 23.","key":"ref_49","DOI":"10.3390\/ijms23115938"},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"648","DOI":"10.1038\/nm0610-648","article-title":"Sudden Cardio Arrest: Oxidative stress irritates the heart","volume":"16","author":"Tomaselli","year":"2010","journal-title":"Nat. Med."},{"doi-asserted-by":"crossref","unstructured":"Frecska, E., Bokor, P., and Winkelman, M. (2016). The Therapeutic Potentials of Ayahuasca: Possible Effects against Various Diseases of Civilization. Front. Pharmacol., 7.","key":"ref_51","DOI":"10.3389\/fphar.2016.00035"},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"155","DOI":"10.1016\/S0378-8741(02)00034-X","article-title":"Anti-diabetic activity of medicinal plants and its relationship with their antioxidant property","volume":"81","author":"Sabu","year":"2002","journal-title":"J. Ethnopharmacol."},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"865","DOI":"10.4103\/1673-5374.184447","article-title":"Neuroprotection and antioxidants","volume":"11","year":"2016","journal-title":"Neural Regen. Res."},{"doi-asserted-by":"crossref","unstructured":"Rusu, M.E., Fize\u0219an, I., Vlase, L., and Popa, D.S. (2022). Antioxidants in Age-Related Diseases and Anti-Aging Strategies. Antioxidants, 11.","key":"ref_54","DOI":"10.3390\/antiox11101868"},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"63","DOI":"10.3233\/JBR-2012-028","article-title":"Polyphenols and health: Moving beyond antioxidants","volume":"2","author":"Visioli","year":"2012","journal-title":"J. Berry Res."},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"215S","DOI":"10.1093\/ajcn\/81.1.215S","article-title":"Polyphenols: Antioxidants and beyond","volume":"81","author":"Scalbert","year":"2005","journal-title":"Am. J. Clin. Nutr."},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"618","DOI":"10.1016\/j.stem.2010.08.012","article-title":"Highly efficient reprogramming to pluripotency and directed differentiation of human cells with synthetic modified mRNA","volume":"7","author":"Warren","year":"2010","journal-title":"Cell Stem Cell"},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"790","DOI":"10.1134\/S1068162017070081","article-title":"The antioxidant activity of the Russian Far East representatives of the Spiraea L. genus (Rosaceae Juss.)","volume":"43","author":"Kostikova","year":"2017","journal-title":"Russ. J. Bioorg. Chem."},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"622","DOI":"10.1007\/s11094-020-02246-3","article-title":"Antioxidant Properties of Extracts of Leaves and Inflorescences of Spiraea Media Franz Schmidt from the Flora of Komi Republic","volume":"54","author":"Shirshova","year":"2020","journal-title":"Pharm. Chem. J."},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"128","DOI":"10.26577\/ijbch-2019-1-i17","article-title":"Investigation of Chemical Constituents of Medicinal Plant Spiraea Hypericifolia L","volume":"12","author":"Kudaibergen","year":"2019","journal-title":"Int. J. Biol. Chem."},{"doi-asserted-by":"crossref","unstructured":"Kradin, R.L., and Fishman, J.A. (2014). Influenza Virus. Viruses and the Lung, Springer.","key":"ref_61","DOI":"10.1007\/978-3-642-40605-8_9"},{"key":"ref_62","doi-asserted-by":"crossref","first-page":"S82","DOI":"10.1086\/507558","article-title":"Epidemiology of seasonal influenza: Use of surveillance data and statistical models to estimate the burden of disease","volume":"194","author":"Thompson","year":"2006","journal-title":"J. Infect. Dis."},{"doi-asserted-by":"crossref","unstructured":"De Angelis, M., Della-Morte, D., Buttinelli, G., Di Martino, A., Pacifici, F., Checconi, P., Ambrosio, L., Stefanelli, P., Palamara, A.T., and Garaci, E. (2021). Protective Role of Combined Polyphenols and Micronutrients against Influenza A Virus and SARS-CoV-2 Infection In Vitro. Biomedicines, 9.","key":"ref_63","DOI":"10.3390\/biomedicines9111721"},{"key":"ref_64","doi-asserted-by":"crossref","first-page":"3730","DOI":"10.1021\/jf104982y","article-title":"Protective effect of apple polyphenols against stress-provoked influenza viral infection in restraint mice","volume":"59","author":"He","year":"2011","journal-title":"J. Agric. Food Chem."},{"key":"ref_65","doi-asserted-by":"crossref","first-page":"289","DOI":"10.1016\/0166-3542(93)90008-7","article-title":"Inhibition of the infectivity of influenza virus by tea polyphenols","volume":"21","author":"Nakayama","year":"1993","journal-title":"Antivir. Res."},{"unstructured":"Kostikova, V.A., Filippova, E.I., Vysochina, G.I., and Mazurkova, N.A. (2016, January 1\u20138). Antiviral activity of plants of the genus Spiraea (Rosaceae) growing in the Asian part of Russia. Proceedings of the International Conference Dedicated to the 70th Anniversary of Central Siberian Botanical Garden \u201cPreserving the Diversity of Flora in the Botanical Gardens: Tradition, Modernity and Perspectives\u201d, CSBG SB RAS, Novosibirsk, Russia. (In Russian).","key":"ref_66"},{"key":"ref_67","doi-asserted-by":"crossref","first-page":"57","DOI":"10.1586\/14787210.2016.1120670","article-title":"The preventive and therapeutic potential of natural polyphenols on influenza","volume":"14","author":"Bahramsoltani","year":"2016","journal-title":"Expert Rev. Anti-Infect. Ther."},{"key":"ref_68","doi-asserted-by":"crossref","first-page":"217","DOI":"10.1007\/s11418-011-0563-5","article-title":"New \u03b1-glucosides of caffeoyl quinic acid from the leaves of Moringa oleifera Lam","volume":"66","author":"Kashiwada","year":"2012","journal-title":"J. Nat. Med."},{"key":"ref_69","doi-asserted-by":"crossref","first-page":"8493","DOI":"10.1021\/jm3009844","article-title":"Enhanced anti-influenza agents conjugated with anti-inflammatory activity","volume":"55","author":"Liu","year":"2012","journal-title":"J. Med. Chem."},{"key":"ref_70","doi-asserted-by":"crossref","first-page":"3556","DOI":"10.1016\/j.bmcl.2013.04.033","article-title":"Caffeic acid derivatives: A new type of influenza neuraminidase inhibitors","volume":"23","author":"Xie","year":"2013","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_71","doi-asserted-by":"crossref","first-page":"1106","DOI":"10.2174\/138955708785909943","article-title":"Antiviral activity of phytochemicals: A comprehensive review","volume":"8","author":"Naithani","year":"2008","journal-title":"Mini Rev. Med. Chem."},{"doi-asserted-by":"crossref","unstructured":"Manso, T., Lores, M., and de Miguel, T. (2021). Antimicrobial Activity of Polyphenols and Natural Polyphenolic Extracts on Clinical Isolates. Antibiotics, 11.","key":"ref_72","DOI":"10.3390\/antibiotics11010046"},{"key":"ref_73","doi-asserted-by":"crossref","first-page":"174","DOI":"10.1016\/j.copbio.2011.08.007","article-title":"Polyphenols as antimicrobial agents","volume":"23","author":"Daglia","year":"2012","journal-title":"Curr. Opin. Biotechnol."},{"key":"ref_74","doi-asserted-by":"crossref","first-page":"715","DOI":"10.1016\/j.foodchem.2009.07.019","article-title":"Polyphenolic profile, antioxidant properties and antimicrobial activity of grape skin extracts of 14 Vitis vinifera varieties grown in Dalmatia (Croatia)","volume":"119","author":"Katalinic","year":"2010","journal-title":"Food Chem."},{"key":"ref_75","first-page":"813","article-title":"Antioxidant and Antimicrobial Activity of Polyphenol Extracts from Wild Berry Fruits Grown in Southeast Serbia","volume":"12","author":"Andjelkovic","year":"2013","journal-title":"Trop. J. Pharm. Res."},{"doi-asserted-by":"crossref","unstructured":"Othman, L., Sleiman, A., and Abdel-Massih, R.M. (2019). Antimicrobial Activity of Polyphenols and Alkaloids in Middle Eastern Plants. Front. Microbiol., 10.","key":"ref_76","DOI":"10.3389\/fmicb.2019.00911"},{"key":"ref_77","doi-asserted-by":"crossref","first-page":"762","DOI":"10.1186\/s13104-017-3013-y","article-title":"Phytochemical and pharmacological investigation of Spiraea chamaedryfolia: A contribution to the chemotaxonomy of Spiraea genus","volume":"10","author":"Kiss","year":"2017","journal-title":"BMC Res. Notes"},{"unstructured":"Kiss, T. (2017). Phytochemical, Pharmacological and Toxicological Studies of Alkaloid-and Sesquiterpene Lactone-Containing Medicinal Plants. [Ph.D. Thesis, University of Szeged].","key":"ref_78"},{"key":"ref_79","doi-asserted-by":"crossref","first-page":"48","DOI":"10.1055\/a-0750-6907","article-title":"Pharmacological Properties of Geraniol\u2014A Review","volume":"85","author":"Lei","year":"2019","journal-title":"Planta Med."},{"key":"ref_80","doi-asserted-by":"crossref","first-page":"187","DOI":"10.1080\/10412905.2020.1745697","article-title":"Antimicrobial activity of geraniol: An integrative review","volume":"32","author":"Moraes","year":"2020","journal-title":"J. Essent. Oil Res."},{"doi-asserted-by":"crossref","unstructured":"Leonova, T., Popova, V., Tsarev, A., Henning, C., Antonova, K., Rogovskaya, N., Vikhnina, M., Baldensperger, T., Soboleva, A., and Dinastia, E. (2020). Does Protein Glycation Impact on the Drought-Related Changes in Metabolism and Nutritional Properties of Mature Pea (Pisum sativum L.) Seeds?. Int. J. Mol. Sci., 21.","key":"ref_81","DOI":"10.3390\/ijms21020567"}],"container-title":["International Journal of Molecular Sciences"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1422-0067\/26\/8\/3587\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,9]],"date-time":"2025-10-09T17:12:28Z","timestamp":1760029948000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1422-0067\/26\/8\/3587"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2025,4,10]]},"references-count":81,"journal-issue":{"issue":"8","published-online":{"date-parts":[[2025,4]]}},"alternative-id":["ijms26083587"],"URL":"https:\/\/doi.org\/10.3390\/ijms26083587","relation":{},"ISSN":["1422-0067"],"issn-type":[{"type":"electronic","value":"1422-0067"}],"subject":[],"published":{"date-parts":[[2025,4,10]]}}}