Chemical constituents of Geum rivale L. and their biological activity

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The aim of the study is to review the literature data on the chemical constituents of arial and underground parts of Geum rivale L. (Rosaceae) and the pharmacological activity of its extracts and individual compounds.

Materials and methods. The study was carried out using Internet resources (Google Scholar, PubMed) and library databases (e-Library, Scopus, Web of Science). The main research methods were a review and analysis of the literature data on the topic for the period from 1958 up to the present.

Results. For the period from 1958 up to the present more than 80 components in the arial and underground parts of G. rivale have been identified. Among them there were components of the essential oil, phenolic acids and coumarins, aglycones of flavonoids, including luteolin, apigenin, quercetin and kaempferol, as well as a number of their glycosides and glucuronides, ellagitannins (hemin A, B, C, D, pedunculagin, stachiurin/casuarinin, tellimagrandin I). Some aspects of the pharmacological activity of total extracts and individual secondary metabolites of G. rivale have been studied, anti-inflammatory, antioxidant, antimicrobial, antiviral activities have been experimentally confirmed.

Conclusion. The analysis of the literature data showed that a further study of the composition of metabolites of G. rivale and their pharmacological activity is an urgent task, the solution of which will expand the range of use of this plant in medical practice and consider G. rivale as a promising source of pharmaceutical substances for the creation of new drugs and biologically active additives.

作者简介

Anastasia Orlova

Saint Petersburg State Chemical Pharmaceutical University

编辑信件的主要联系方式.
Email: anastasiya.lebedkova@spcpu.ru
ORCID iD: 0000-0002-7836-5785

postgraduate student of the Department of Pharmacognosy, Junior Researcher of the Research Department

俄罗斯联邦, 14 lit. A, Professor Popov St., St. Petersburg,197022

Maria Povydysh

Saint Petersburg State Chemical Pharmaceutical University

Email: maria.povydysh@pharminnotech.com
ORCID iD: 0000-0002-7768-9059

Doctor of Sciences (Biology), Candidate of Sciences (Pharmacy), Associate Professor of the Department of Pharmacognosy, Head of the Research Department

俄罗斯联邦, 14 lit. A, Professor Popov St., St. Petersburg, 197022

参考

  1. Tsvelev NN. Flora vostochnoi Evropi. Tom X. [Flora Europae Orientalis. Volume 10]. SPb.: World and family. Ed. SPHFA. 2001;10:460–466. Russian.
  2. Gubanov IA, Kiseleva KV, Novikov VS, Tikhomirov VS. Illyustrirovannyy opredelitel rasteniy Sredney Rossii. T. 2. [An illustrated guide to plants of Central Russia. T. 2]. M.: KMK Scientific Publishing Partnership, Institute of technological research. 2003:2190. Russian.
  3. Mayevsky PF. Flora sredney polosy evropeyskoy chasti Rossii. 10-e izd [Flora of the middle zone of the European part of Russia. 10th ed.]. M.: KMK Scientific Publishing Partnership. 2006:379–400. Russian.
  4. Elenevsky AG, Radygina VI, Chaadaeva NN. Rasteniya Belgorodskoy oblasti (konspekt flory) [Plants of the Belgorod region (flora synopsis)]. M.: Moscow State Pedagogical University. 2004:120 p. Russian.
  5. Lazarev AV, Burchenko TV. Rod Geum v sovremennykh ekologicheskikh usloviyakh sredney Rossii [Genus Geum in the modern ecological conditions of Central Russia]. Scientific Bulletin. 2009;3(58):34–38. Russian.
  6. Hulten E. The Amphi-Atlantic Plants and their Phytogeographical Connections. Kongl. Svenska Vetens. – Akad. Handl. 1958;7(1):1–340.
  7. Taylor K. Geum rivale L. Journal of Ecology. 1997;85(5):721–731.
  8. Hulden L. The first Finnish malariologist, Johan Haartman, and the discussion about malaria in 18th century Turku, Finland. Malaria Journal. 2011;10:43. doi: 10.1186/1475-2875-10-43.
  9. Thomson Healthcare. Physicians’ desk reference for herbal medicines. Thomson Healthcare (Firm), 4th ed. Montvale, NJ: Thomson. 2007:71–72.
  10. Vollmann C, Scbultze W. Composition of the Root Essential Oils of Several Geum Species and Related Members of the Subtribus Geinae (Rosaceae). Flavour and Fragrance Journal. 1995;10:173–178.
  11. Birnesser H, Stolt P. The Homeopathic antiarthritic preparation Zeel comp. N: Review of Molecular and Clinical Data. Explore. 2007;3(1):16–22. doi: 10.1016/j.explore.2006.10.002.
  12. Egoshina TL, Luginina EA. Medicinal plants in folk medicine of taiga zone of Russia: peculiarities of use and resources. Plant, fungal and habitat diversity investigation and conservation. Proceedings of IV BBC – Sofia, 20-26 June 2006:624-631. doi: 10.13140/2.1.4303.9044.
  13. Vollmann C, Scbultze W. Composition of the Root Essential Oils of Several Geum Species and Related Members of the Subtribus Geinae (Rosaceae). Flavour and Fragrance Journal. 1995;10:173–178.
  14. Owczarek A, Gudej J, Kicel A. Composition of Essential Oil from Aerial and Underground Parts of Geum rivale and G. urbanum Growing in Poland. Natural Product Communications. 2013;8(4):505–508. doi: 10.1177/1934578X1300800425.
  15. Cheng X-R, Jin H-Z, Qin J-J, Fu J-J, Zhang W-D Chemical Constituents of Plants from the Genus Geum. Chemistry and biodiversity. 2011;8(2):203–222. doi: 10.1002/cbdv.200900347.
  16. Panizzi L, Catalano S, Miarelli C, Cioni P. L, Campeol E. In vitro Antimicrobial Activity of Extracts and Isolated Constituents of Geum rivale. Phytotherapy Research. 2000;14(7):561–653. doi: 10.1002/1099-1573(200011)14:7<561::AID-PTR651>3.0.CO;2-H.
  17. Owczarek A, Gudej J. Investigation into biological active constituents of Geum rivale L. Acta Poloniae Pharmaceutica – Drug research. 2013;70(1):111–114.
  18. Morozova EV, Chemesova II, Yakovlev GP. Soderzhaniye i sostav fenolkarbonovykh kislot v Geum rivale, G. urbanum i G. aleppicum (Rosaceae) [Content and composition of phenolcarboxylic acids in Geum rivale, G. urbanum, and G. aleppicum (Rosaceae)]. Plant resources. 2009;45(4):54–55. Russian.
  19. Polukhina TS, Pogudina SF, Inizarova DR. Kolichestvennoye opredeleniye flavonoidov v nadzemnoy chasti gravilata rechnogo (Geum rivale L.) [Quantitative determination of flavonoids in the aboveground part of the water avens (Geum rivale L.)]. Modern scientific research: Actual problems, achievements and innovations. Collection of articles by the winners of the III International Scientific and Practical Conference. Publ.: Science and Education. 2017:225–227. Russian.
  20. Оwczarek А, Olszewska MA, Gudej J. Quantitative determination of ellagic acid and gallic acid in Geum rivale L. and G. urbanum L. Acta Biologica Cracoviensia Sertes Botanica. 2014;56/2:74–78. doi: 10.2478/abcsb-2014-0021.
  21. Orlova A, Povydysh M. Obzor metodov kachestvennogo i kolichestvennogo analiza taninov v rastitelnom syrye [Review of methods of qualitative and quantitative analysis of tannins in raw plant materials]. Chemistry of plant raw materials. 2019;4:29–45. Russian. DOI: 10.14258 / jcprm.2019045459.
  22. Moilanen J, Salminen J-P. Ecologically neglected tannins and their biologically relevant activity: chemical structures of plant ellagitannins reveal their in vitro oxidative activity at high pH. Chemoecology. 2008;18:73–83. doi: 10.1007/s00049-007-0395-7.
  23. Moilanen J, Koskinen Р, Salminen J-P. Distribution and content of ellagitannins in Finnish plant species. Phytochemistry. 2015;116:188–197. doi: 10.1016/j.phytochem.2015.03.002.
  24. Ming D-Sh, Jiang R-W, But P P-H, Towers GH N, Yu D-Q. A new compound from Geum rivale L. Journal of Asian Natural Products Research. 2002;4(3):217–220. doi: 10.1080/10286020290024022.
  25. Owczarek A, Ró˙zalski M, Krajewska U, Olszewska MA. Rare Ellagic Acid Sulphate Derivatives from the Rhizome of Geum rivale L. – Structure, Cytotoxicity, and Validated HPLC-PDA Assay. Applied Science. 2017;7(4):400. doi: 10.3390/app7040400.
  26. Budantsev AL. Rastitelnyye resursy Rossii. Tom 2. Semeystva Actinidiaceae – Malvaceae. Euphorbiaceae – Haloragaceae [Plant resources of Russia. Volume 2. Families Actinidiaceae – Malvaceae, Euphorbiaceae – Haloragaceae]. Ed. AL Budantsev. SPb: KMK Scientific Publishing Partnership. 2009:513. Russian.
  27. Tunon H, Olavsdotter C, Bohlin L. Evaluation of anti-inflammatory activity of some Swedish medicinal plants. Inhibition of prostaglandin biosynthesis and PAF-induced exocytosis. Journal of Ethnopharmacology. 1995;48:61–76. doi: 10.1016/0378-8741(95)01285-l.
  28. Birnesser H, Stolt P. The Homeopathic Antiarthitic Preparation Zeel comp. N: A Review of Molecular and Clinical Data. Explore. 2007;3(1):16–22. doi: 10.1016/j.explore.2006.10.002.
  29. Parimala Devi B, Tamilchelvan N, Ramasubramaniaraja R. Inflammation and Medicinal Plants – An Ethnomedicinal Approach. 2010;2(2):49–56.
  30. Owczarek A, Gudej J, Olszewska MA. Antioxidant activity of Geum rivale L. and Geum urbanum L. Acta Poloniae Pharmaceutica – Drug research. 2015;72(6):1239–1244.
  31. Brand-Williams W, Cuvelier ME, Berset C. Use of a free radical method to evaluate antioxidant activity. LWT – Food Science and Technology. 1995;28(1):25–30. doi: 10.1016/S0023-6438(95)80008-5.
  32. Olszewska MA, Presler A, Michel P. Profiling of Phenolic Compounds and Antioxidant Activity of Dry Extracts from the Selected Sorbus Species. Molecules. 2012;17(3):3093–3113. doi: 10.3390/molecules17033093.
  33. Pulido R, Bravo L, Saura-Calixto F. Antioxidant Activity of Dietary Polyphenols as Determined by a Modified Ferric Reducing/Antioxidant Power Assay. Journal of Agricultural and Food Chemistry. 2000;48(8):3396–3402. doi: 10.1021/jf9913458.
  34. Olszewska MA, Michel P. Antioxidant activity of inflorescences, leaves and fruits of three Sorbus species in relation to their polyphenolic composition. Natural Product Research. 2009; 23(16): 1507–1521. doi: 10.1021/jf9913458.
  35. Azuma K, Nakayama M, Koshioka M, Ippoushi K, Yamaguchi Y, Kohata K, Yamauchi Y, Ito H, Higashio H. Phenolic Antioxidants from the Leaves of Corchorus olitorius L. Journal of Agricultural and Food Chemistry. 1999;47(10):3963–3966. doi: 10.1021/jf990347p.
  36. Oszmianski J, Wojdylo A, Lamer-Zarawska E, Swiader K. Antioxidant tannins from Rosaceae plant roots. Food chemistry. 2007;100:579–583. doi: 10.1016/j.foodchem.2005.09.086.
  37. Guyot S, Marnet N, Sanoner P, Drilleau JF. Direct thiolysis on crude apple materials for HPLC characterization and quantification of polyphenols in cider apple tissues and juices. Methods in Enzymology. 2001;335:57–70. doi: 10.1016/S0076-6879(01)35231-X.
  38. Yen GC, Chen HY. Antioxidant activity of various tea extracts in relation to their antimutagenicity. Journal of Agricultural and Food Chemistry. 1995;43:27–32. doi: 10.1021/jf00049a007.
  39. Re R, Pellegrini N, Proteggente A, Pannala A, Yang M, Rice-Evans C. Antioxidant activity applying an improved ABTS radical cation decolorization assay. Free Radical Biology & Medicine. 1999;26(9/10):1231–1237. doi: 10.1016/S0891-5849(98)00315-3.
  40. Clark AM, El-Feraly FS, Li WS. Antimicrobial activity of phenolic constituents of Magnolia grandiflora L. Journal of Pharmaceutical Science. 1981;70:951–952. doi: 10.1002/jps.2600700833.
  41. Varaprasad B. A Search for Antibacterial Agents Edited by Varaprasad Bobbarala. Published by InTech Janeza Trdine 9, 51000 Rijeka, Croatia. 2012:8.
  42. Levina AS, Repkova MN, Mazurkova NA, Makarevich EV, Ismagilov ZR, Zarytova VF. Knockdown of different influenza A virus subtypes in cell culture by a single antisense oligodeoxyribonucleotide. International Journal of Antimicrobial Agents. 2015;46(1):125–128. doi: 10.1016/j.ijantimicag.2015.03.004.
  43. Lobanova IE, Filippova EI, Vysochina GI, Mazurkova NA. Protivovirusnyye svoystva dikorastushchikh i kultiviruyemykh rasteniy yugo-zapadnoy Sibiri. Rastitelnyy mir aziatskoy Rossii. 2016;2(22):64–72. Russian.
  44. Kostina NE, Ibragimova ZhB, Protsenko MA, Makarevich EV, Skarnovich MA, Filippova EI, Gorbunova IA, Vlasenko VA, Troshkova GP, Mazurkova NA, Shishkina LN. Vydeleniye, kharakteristika i protivovirusnyye svoystva biologicheski aktivnykh veshchestv iz vysshikh gribov Zapadnoy Sibiri [Isolation, characterization and antiviral properties of biologically active substances from higher fungi of Western Siberia]. Rational nutrition, food additives and biostimulants. 2014;2:25–26. Russian.
  45. Zaks L. Statisticheskoye otsenivaniye. Seriya: Zarubezhnyye statisticheskiye issledovaniya. Perevod s nemetskogo [Statistical estimation. Series: Foreign Statistical Studies. Translated from German] M.: Statistics. 1976: 598. Russian.
  46. Kozira SA, Kulagina MA, Serbin AG. Khimichniy sklad ta vikoristannya v meditsini roslin rodu Geum L. (Obzor literaturi) [Chemistry warehouse and vikorystannya in the medical plant of the genus Geum L. (Literature review)]. Zaporozhye medical journal. 2008;2(47):80–82.
  47. Garcia-Nino WR, Zazueta C. Ellagic acid: Pharmacological activities and molecular mechanisms involved in liver protection. Pharmacological Research. 2015; 97: 84–103. DOI: http://dx.doi.org/10.1016/j.phrs.2015.04.008.
  48. Zahin M, Ahmad I, Gupta RC, Aqil F. Punicalagin and ellagic acid demonstrate antimutagenic activity and inhibition of benzo[a]pyrene induced DNA adducts. BioMed Research International. 2014:467465. doi: 10.1155/2014/467465,467465.
  49. Rehman MU, Tahir M, Ali F. Cyclophosphamide-induced nephrotoxicity, genotoxicity, and damage in kidney genomic DNA of Swiss albino mice: the protective effect of ellagic acid. Molecular and Cellular Biochemistry. 2012;365(1–2):119–127. doi: 10.1007/s11010-012-1250-x.
  50. Abraham SK. Anti-genotoxic effects in mice after the interaction between coffee and dietary constituents. Food Chemical Toxicology. 1996;34:15–20. doi: 10.1016/0278-6915(95)00085-2.
  51. Khanduja KL, Avti PK, Kumar S, Mittal N, Sohi KK, Pathak CM. Anti-apoptotic activity of caffeic acid, ellagic acid and ferulic acid in normal human peripheral blood mononuclearcells: a Bcl-2 independent mechanism. Biochimica et Biophysica Acta (BBA) – General Subjects. 2006;1760(2):283–289. doi: 10.1016/j.bbagen.2005.12.017.
  52. Li T, Chen G, Su C, Lin J-G, Yen C, Cheng K., Chung J. Ellagic acid induced p53/p21 expression, G1 arrestand apoptosis in human bladder cancer T24 cells. Anticancer Research. 2005;25(2A):971–979.
  53. Abuelsaad AS, Mohamed I, Allam G, Al-solumani AA. Antimicrobial andimmunomodulating activities of hesperidin and ellagic acid against diarrheic Aeromonas hydrophila in a murine model. Life Science. 2013;93(20):714–722. doi: 10.1016/j.lfs.2013.09.019.
  54. Park SW, Kwon MJ, Yoo JY, Choi HJ, Ahn YJ. Antiviral activity and possible mode ofaction of ellagic acid identified in Lagerstroemia speciosa leaves toward human rhinoviruses. BMC Complementary and Alternative Medicine. 2014;14:171. doi: 10.1186/1472-6882-14-171.
  55. Soh PN, Witkowski B, Olagnier D, Nicolau M-L, Garcia-Alvares M-C, Benoit-Vical F. In vitro and in vivo properties ofellagic acid in malaria treatment. Antimicrobial Agents and Chemotherapy. 2009;53(3):1100–1106. doi: 10.1128/AAC.01175-08.
  56. Choi YH, Yan GH. Ellagic Acid attenuates immunoglobulin E-mediated allergic response in mast cells. Biological and Pharmaceutical Bulletin. 2009;32(6):1118–1121. doi: 10.1248/bpb.32.1118.
  57. Promsong A. Wo C, Satthakarn S, Nittayananta W. Ellagic acid modulates the expression of oral innate immune mediators: potential role in mucosal protection. Journal of Oral Pathology Medicine. 2014;44(3):214–221. doi: 10.1111/jop.12223.
  58. Kuo M-Y, Ou H-C, Lee W-J, Kuo W-W, Hwang L-L, Song T-Y, Huang C-Y, Chiu T-H, Tsai K-L, Tsai C-S, Sheu WH-H. Ellagic acid inhibits oxidized low-density lipoprotein (OxLDL)-induced metalloproteinase (MMP) expression by modulating the protein kinase C-α/extracellular signal-regulated kinase/peroxisome proliferator-activated receptor γ/nuclear factor-κB (PKC-α/ERK/ PPAR-γ/NF-κB) Signaling Pathway in Endothelial Cells. Journal of Agricultural and Food Chemistry. 2011;59(9):5100–5108. doi: 10.1021/jf1041867.
  59. Pinto M da S, de Carvalho JE, Lajolo FM, Genovece MI, Shetty K. Evaluation of antiproliferative, anti-type 2 diabetes, and antihypertension potentials of ellagitannins from strawberries (Fragaria × ananassa Duch.) using in vitro models. Journal of Medicinal Food. 2010;13(5):1027–1035. doi: 10.1089/jmf.2009.0257.
  60. Dhingra D, Jangra A. Antiepileptic activity of ellagic acid, a naturally occurring polyphenolic compound, in mice. Journal of Functional Foods. 2014;10:364–369. doi: 10.1016/j.jff.2014.07.011.
  61. Dhingra D, Chhillar R. Antidepressant-like activity of ellagic acid in unstressed and acute immobilization-induced stressed mice. Pharmacological Reports. 2012;64(4):796–807. doi: 10.1016/S1734-1140(12)70875-7.
  62. Girish C, Raj V, Arya J, Balakrishnan S. Involvement of the GABAergic sys-tem in the anxiolytic-like effect of the flavonoid ellagic acid in mice. European Journal of Pharmacology. 2013;710(1–3):49–58. doi: 10.1016/j.ejphar.2013.04.003.
  63. Kwak H, Jeon S, Sohng B, Kim J, Lee J, Lee K, Jeong H, Hur J, Kang Y, Song K. β-Secretase (BACE1) inhibitors from pomegranate (Punica granatum) husk. Archives of Pharmacal Research. 2005;28(12):1328–1332. doi: 10.1007/BF02977896.
  64. El-Garhy AM, Abd El-Raouf OM, El-Sayeh BM, Fawzy HM, Abdallah DM. Ellagic acid antiinflammatory and antiapoptotic potential mediate renoprotection in cisplatin nephrotoxic rats. Journal of Biochemical and Molecular Toxicology. 2014;28(10):472–479. doi: 10.1002/jbt.21587.
  65. Kannan MM, Quine SD. Ellagic acid inhibits cardiac arrhythmias, hypertrophy and hyperlipidaemia during myocardial infarction in rats. Metabolism. 2013;62(1):52–61. doi: 10.1016/j.metabol.2012.06.003.
  66. Lee JH, Won JH, Choi JM, Cha HH, Jang YJ, Park S, Kim HG, Kim HC, Kim DK. Protective effect of ellagic acid on concanavalin A-induced hepatitis via Toll-like receptor and mitogen-activated protein kinase/nuclear factor κB signaling pathways. Journal of Agricultural and Food Chemistry. 2014;62(41):10110–10117. doi: 10.1021/jf503188c.

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2. Figure 1 – Triterpenoids of the arial part of G. rivale (Panizzi, L. et al., 2000)

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3. Figure 2 – Phenolic acids and coumarins of G. rivale (Panizzi et al.,2000; Owczarek et al., 2013)

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4. Figure 3 – Flavonoids of G. rivale (Panizzi et al., 2000)

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5. Figure 4 – Ellagitannins of G. rivale (Moilanen et al.,2008, 2015; Owczarek et al., 2017)

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