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2019 | 88 | 1 |

Tytuł artykułu

Phytochemical screening of Pulsatilla species and investigation of their biological activities

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EN

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EN
The present study aimed to identify biologically active secondary metabolites from the rare plant species, Pulsatilla patens subsp. patens and the cultivated P. vulgaris subsp. vulgaris. Chromatographic fractionation of the ethanolic extract of the roots of P. patens subsp. patens resulted in the isolation of two oleanane-type glycosides identified as hederagenin 3-O-β-d-glucopyranoside (2.7 mg) and hederagenin 3-O-β-d-galactopyranosyl-(1→2)-β-d-glucopyranoside (3.3 mg, patensin). HPLC analysis of the methanolic extract of the crude root of P. patens subsp. patens and P. vulgaris subsp. vulgaris revealed the presence of Pulsatilla saponin D (hederagenin 3-O-α-l-rhamnopyranosyl(1→2)-[β-d-glucopyranosyl(1→4)]-α-l-arabinopyranoside). Chromatographic analysis using GC-MS of the silylated methanolic extracts from the leaves and roots of these species identified the presence of carboxylic acids, such as benzoic, caffeic, malic, and succinic acids. The extracts from Pulsatilla species were tested for their antifungal, antimicrobial, and antimalarial activities, and cytotoxicity to mammalian cell lines. Both P. patens subsp. patens and P. vulgaris subsp. vulgaris were active against the fungus Candida glabrata with the half-maximal inhibitory concentration (IC₅₀) values of 9.37 μg/mL and 11 μg/mL, respectively. The IC₅₀ values for cytotoxicity evaluation were in the range of 32–38 μg/mL for P. patens subsp. patens and 35–57 μg/mL for P. vulgaris subsp. vulgaris for each cell line, indicating general cytotoxic activity throughout the panel of evaluated cancer and noncancer cells.

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Opis fizyczny

Article 3613 [17p.],fig.,ref.

Twórcy

autor
  • Department of Agri-Food Engineering and Environmental Management, Bialystok University of Technology, Wiejska 45A, 15-351 Bialystok, Poland
  • Department of Agri-Food Engineering and Environmental Management, Bialystok University of Technology, Wiejska 45A, 15-351 Bialystok, Poland
autor
  • Department of Forestry in Hajnówka, Bialystok University of Technology, Wiejska 45A, 15-351 Bialystok, Poland
  • Department of BioMolecular Sciences, School of Pharmacy, University of Mississippi, MS 38677, United States
autor
  • Department of BioMolecular Sciences, School of Pharmacy, University of Mississippi, MS 38677, United States
autor
  • Department of Plant Biochemistry and Toxicology, University of Bialystok, Ciolkowskiego 1J, 15-245 Bialystok, Poland
  • Department of Plant Biochemistry and Toxicology, University of Bialystok, Ciolkowskiego 1J, 15-245 Bialystok, Poland
autor
  • National Center for Natural Products Research, University of Mississippi, University, MS 38677, United States
autor
  • National Center for Natural Products Research, University of Mississippi, University, MS 38677, United States

Bibliografia

  • 1. Kim Y, Bang SC, Lee JH, Ahn BZ. Pulsatilla saponin D: the antitumor principle from Pulsatilla koreana. Arch Pharm Res. 2004;27(9):915–918. https://doi.org/10.1007/BF02975843
  • 2. Bang SC, Kim Y, Lee JH, Ahn BZ. Triterpenoid saponins from the roots of Pulsatilla koreana. J Nat Prod. 2005;68(2):268–272. https://doi.org/10.1021/np049813h
  • 3. Seo KH, Jung JW, Thi NN, Lee YH, Baek NI. Flavonoid glycosides from the flowers of Pulsatilla koreana Nakai. Natural Product Sciences. 2016;22(1):41–45. https://doi.org/10.20307/nps.2016.22.1.41
  • 4. Shumova GS, Savelieva EV, Vladymyrova IN, Tishakova TS. Phenolic compound composition of herb of Pulsatilla pratensis (L.) Mill. World Science. 2017;12(28):35–38.
  • 5. Shu Z, Chen Z, Liu YL, Zhu WF, Feng YL, Xu QM, et al. A new oleanane-type triterpenoidal saponin from Pulsatilla chinensis. Nat Prod Res. 2013;27(23):2196–2201. https://doi.org/10.1080/14786419.2013.814052
  • 6. Yang H, Cho YW, Kim SH, Kim YC, Sung SH. Triterpenoidal saponins of Pulsatilla koreana roots. Phytochemistry. 2010;71(16):1892–1899. https://doi.org/10.1016/j.phytochem.2010.07.013
  • 7. Fan W, Liu J, Gong Y, Ma J, Zhou N, Xu Y. A new triterpenoid saponin from Pulsatilla cernua. Natural Product Sciences. 2013;19(2):150–154.
  • 8. Sun H, Wang Y, Zhang XQ, Zhao SX, Ye WC. Chemical constituents of Pulsatilla dahurica. Chem Nat Compd. 2009;45(5):764–765. https://doi.org/10.1007/s10600-009-9454-3
  • 9. Xu HJ, Shi XW, Ji X, Du YF, Zhu H, Zhang LT. A rapid method for simultaneous determination of triterpenoid saponins in Pulsatilla turczaninovii using microwave-assisted extraction and high performance liquid chromatography-tandem mass spectrometry. Food Chem. 2012;135(1):251–258. https://doi.org/10.1016/j.foodchem.2012.04.081
  • 10. Samadder A, Das J, Das S, Khuda-Bukhsh AR. Dihydroxy-isosteviol-methyl-ester, an active biological component of Pulsatilla nigricans, reduces arsenic induced cellular dysfunction in testis of male mice. Environ Toxicol Pharmacol. 2012;34(3):743–752. https://doi.org/10.1016/j.etap.2012.09.013
  • 11. Rolski S, Przyborowski L. Dissertationes Pharmaceuticae. 1961;13:349–355.
  • 12. Ye WC, Ji NN, Zhao SX, Che CT. A new cytotoxic saponin from Pulsatilla patens var. multifida. Pharm Biol. 2001;39(1):7–10. https://doi.org/10.1076/phbi.39.1.7.5951
  • 13. Danova K, Bertoli A, Pistelli L, Dimitrow D, Pistelli L. In vitro culture of Balkan endemic and rare Pulsatilla species for conservational purposes and secondary metabolites production. Bot Serb. 2009;33(2):157–162.
  • 14. Xu QM, Shu Z, He WJ, Chen LY, Yang SL, Yang G, et al. Antitumor activity of Pulsatilla chinensis (Bunge) Regel saponins in human liver tumor 7402 cells in vitro and in vivo. Phytomedicine. 2012;19(3–4):293–300. https://doi.org/10.1016/j.phymed.2011.08.066
  • 15. Yoo HH, Lee SK, Lim SY, Kim Y, Kang MJ, Kim EJ, et al. LC-MS/MS method for determination of hederacolchiside E, a neuroactive saponin from Pulsatilla koreana extract in rat plasma for pharmacokinetic study. J Pharm Biomed Anal. 2008;48(5):1425– 1429. https://doi.org/10.1016/j.jpba.2008.09.012
  • 16. Liu JY, Guan YL, Zou LB, Gong YX, Hua HM, Xu YN, et al. Saponins with neuroprotective effects from the roots of Pulsatilla cernua. Molecules. 2012;17:5520– 5531. https://doi.org/10.3390/molecules17055520
  • 17. Dai L, Wang H, Chen Y. The immune-enhancing effect of PcG-A-a glycoprotein isolated from dried root of Pulsatilla chinensis (Bunge) Regel. Chinese Journal of Biochemical Pharmaceutics. 2000;21:230–231.
  • 18. Seo JS, Yun JH, Baek IS, Leem YH, Kang HW, Cho HK, et al. Oriental medicine Jangwonhwan reduces Aβ(1–42) level and β-amyloid deposition in the brain of Tg- APPswe/PS1dE9 mouse model of Alzheimer disease. J Ethnopharmacol. 2010;128:206– 212. https://doi.org/10.1016/j.jep.2010.01.014
  • 19. Li HB, Wong CC, Cheng KW, Chen F. Antioxidant properties in vitro and total phenolic contents in methanol extracts from medicinal plants. LWT – Food Science and Technology. 2008;41:385–390. https://doi.org/10.1016/j.lwt.2007.03.011
  • 20. Lee HS, Beon MS, Kim MK. Selective growth inhibitor toward human intestinal bacteria derived from Pulsatilla cernua root. J Agric Food Chem. 2001;49:4656–4661. https://doi.org/10.1021/jf010609z
  • 21. Xu K, Shu Z, Xu QM, Liu YL, Li XR, Wang YL, et al. Cytotoxic activity of Pulsatilla chinensis saponins and their structure-activity relationship. J Asian Nat Prod Res. 2013;15(6):680–686. https://doi.org/10.1080/10286020.2013.790901
  • 22. Nelson LS, Shih RD, Balick MJ. Handbook of poisonous and injurious plant. New York, NY: The New York Botanical Garden; 2007.
  • 23. Wink M, van Wyk BE. Mind-altering and poisonous plants of the world. A scientifically accurate guide to 1,200 toxic and intoxicating plants. Portland, OR: Timber Press; 2008.
  • 24. Vance JC. Toxic plants of Minnesota: skin toxicity of the Prairie Crocus (Anemone patens L.). Minn Med. 1982;65:149–151.
  • 25. Turner NJ. Counter-irritant and other medicinal uses of plants in Ranunculaceae by native peoples in British Columbia and neighbouring areas. J Ethnopharmacol. 1984;11:181–200. https://doi.org/10.1016/0378-8741(84)90038-2
  • 26. Encyclopedia of Chinese materia medica. Shanghai: Shanghai Science and Technology Press; 1977.
  • 27. Szczecińska M, Sramko G, Wołosz K, Sawicki J. Genetic diversity and population structure of the rare and endangered plant species Pulsatilla patens (L.) Mill. in east Central Europe. PLoS One. 2016;11(3):e0151730. https://doi.org/10.1371/journal.pone.0151730
  • 28. Piqueray J, Saad L, Bizoux JP, Mahy G. Why some species cannot colonise restored habitats? The effects of seed and microsite availability. J Nat Conserv. 2013;21:189–197. https://doi.org/10.1016/j.jnc.2012.12.005
  • 29. Kricsfalusy V. Variations in the life cycle of Anemone patens L. (Ranunculaceae) in wild populations of Canada. Plants (Basel). 2016;5(3):E29. https://doi.org/10.3390/plants5030029
  • 30. Meusel H, Jäger E, Weinert E. Vergleichende Chorologie der Zentraleuropäischen Flora. 1. Karten. Jena: G. Fischer Verl.; 1965.
  • 31. Den virtuella floran – Naturhistoriska riksmuseet [Internet]. 1996 [cited 2017 Aug 1]. Available from: http://linnaeus.nrm.se/flora/di
  • 32. Holub J, Procházka F. Red list of vascular plants of the Czech Republic – 2000. Preslia. 2000;72:187–230.
  • 33. Röder D, Kiehl K. Population structure and population dynamic of Pulsatilla patens (L.) Mill. in relation to vegetation characteristics. Flora. 2006;201:499–507. https://doi.org/10.1016/j.flora.2005.11.001
  • 34. Gärdenfors U. Population viability analysis in the classification of threatened species: problems and potentials. Ecol Bull. 2000;48:181–190.
  • 35. Носков [Noskov] ГА [GA], editor. Красная книга природы Ленинградской области. Растения и грибы [Krasnaja kniga prirody Leningradskoj oblasti. Rastenija i griby]. Vol. 2. Санкт-Петербург [Sankt-Peterbúrg]: Мир [Mir]; 2000.
  • 36. European Nature Information System. Species factsheet for Pulsatilla patens. 2005; Available from: https://eunis.eea.europa.eu/
  • 37. Průša D, Eliáš MLP, Dítě D, Čačko L, Krása P, Podešva Z, et al. Chránené rastliny Českej a Slovenskej republiky. Brno: Computer Press; 2005.
  • 38. Rassi P, Alanen A, Kanerva T, Mannerkoski I, editors. The 2000 red list of Finnish species. Helsinki: The II Committee for the Monitoring of Threatened Species in Finland, the Ministry of the Environment; 2001.
  • 39. Rozporządzenie Ministra Środowiska z dnia 9 października 2014 r. w sprawie ochrony gatunkowej roślin. Journal of Laws of the Republic of Poland (Dziennik Ustaw), 2014 Oct 9, Item 1409.
  • 40. Zając A, Zając M, editors. Distribution atlas of vascular plants in Poland. Cracow: Laboratory of Computer Chorology, Institute of Botany, Jagiellonian University; 2001.
  • 41. IUCN. The IUCN Red List of Threatened Species. Version 2014.1 [Internet]. 2014 [cited 2014 Jun 12]. Available from: http://www.iucnredlist.org/
  • 42. Witkowski ZJ, Król W, Solarz W, editors. Carpathian list of endangered species. Vienna: WWF and Institute of Nature Conservation, Polish Academy of Sciences; 2003.
  • 43. Gärdenfors U. The 2010 red list of Swedish species. Uppsala: ArtDatabanken, SLU; 2010.
  • 44. Cheffings C, Farrell L, editors. The vascular plant red data list for Great Britain. Peterborough: Joint Nature Conservation Committee; 2005.
  • 45. Ludwig G, Schnittler M. Red list of threatened plants in Germany. Bonn: Bundesamt für Naturschutz; 1996.
  • 46. Moser D, Gygax A, Bäumler B, Wyler N, Palese R. Red list of the threatened ferns and flowering plants of Switzerland. Bern: Bundesamt für Umwelt, Wald und Landschaft, Zentrum des Datenverbundnetzes der Schweizer Flora; 2002.
  • 47. Niklfeld H, Schratt-Ehrendorfer L, editors. Red list of threatened plants of Austria. Vienna: Grüne Reihe, Bundesministerium für Umwelt, Jugend und Familie; 1999.
  • 48. Kaźmierczakowa R, Zarzycki K, Mirek Z. Polish red data book of plants. Cracow: W. Szafer Institute of Botany, Polish Academy of Sciences; 2016.
  • 49. Mirek Z, Piękoś-Mirkowa H, Zając A, Zając M. Flowering plants and pteridophytes of Poland. A checklist. Cracow: W. Szafer Institute of Botany, Polish Academy of Sciences; 2002.
  • 50. Li H, Li H, Hao N, Xu Y, Piao Z. Study on HPLC fingerprint characteristics and chemotaxonomy of Pulsatilla medicinal plants. China Journal of Chinese Materia Medica. 2011;36(11):1478–1482.
  • 51. National Committee for Clinical Laboratory Standards. Reference method for broth dilution antifungal susceptibility testing of yeasts: approved standard. Wayne, PA: National Committee for Clinical Laboratory Standards; 2002. [NCCLS; vol 22(15)].
  • 52. National Committee for Clinical Laboratory Standards. Reference method for broth dilution antifungal susceptibility testing of yeasts: approved standard. Wayne, PA: National Committee for Clinical Laboratory Standards; 2002. [NCCLS; vol 22(16)].
  • 53. National Committee for Clinical Laboratory Standards. Performance standards for antimicrobial disk susceptibility tests: approved standard. Wayne, PA: National Committee for Clinical Laboratory Standards; 2003. [NCCLS; vol 23(18)].
  • 54. National Committee for Clinical Laboratory Standards. Performance standards for antimicrobial disk susceptibility tests: approved standard. Wayne, PA: National Committee for Clinical Laboratory Standards; 2006. [NCCLS; vol 26(2)].
  • 55. Franzblau SG, Witzig RS, Mclaughlin JC, Torres P, Madico G, Hernandez A, et al. Rapid, low-technology MIC determination with clinical Mycobacterium tuberculosis isolates by using the microplate Alamar Blue assay. J Clin Microbiol. 1998;36(2):362–366.
  • 56. Makler MT, Hinrichs DJ. Measurement of the lactate dehydrogenase activity of Plasmodium falciparum as an assessment of parasitemia. Am J Trop Med Hyg. 1993;48:205. https://doi.org/10.4269/ajtmh.1993.48.205
  • 57. Borenfreund E, Babich H, Martin-Alguacil N. Rapid chemosensitivity assay with human normal and tumor cells in vitro. In Vitro Cell Dev Biol. 1990;26:1030. https://doi.org/10.1007/BF02624436
  • 58. Fidel PL, Vazquez JA, Sobel JD. Candida glabrata: review of epidemiology, pathogenesis, and clinical disease with comparison to C. albicans. Clin Microbiol Rev. 1999;12(1):80–96. https://doi.org/10.1128/CMR.12.1.80
  • 59. Kim J, Sudbery P. Candida albicans, a major human fungal pathogen. J Microbiol. 2011;49(2):171–177. https://doi.org/10.1007/s12275-011-1064-7
  • 60. Latgé JP. Aspergillus fumigatus and aspergillosis. Clin Microbiol Rev. 1999;12(2):310–350. https://doi.org/10.1128/9781555815523
  • 61. Nataro JP, Kaper JB. Diarrheagenic Escherichia coli. Clin Microbiol Rev. 1998;11(1):142– 201. https://doi.org/10.1128/CMR.11.1.142
  • 62. Streeter K, Katouli M. Pseudomonas aeruginosa: a review of their pathogenesis and prevalence in clinical settings and the environment. Infect Epidemiol Med. 2016;2(1):25– 32. https://doi.org/10.18869/modares.iem.2.1.25
  • 63. Ye WC, Ou BX, Ji NN, Zhao SX, Ye T, Mc Kervey MA, et al. Patensin, a saponin from Pulsatilla patens var. multifida. Phytochemistry. 1995;39(4):937–939. https://doi.org/10.1016/0031-9422(95)00021-X
  • 64. Ye W, Pan G, Zhang Q, Che CT, Wu H, Zhao S. Five new triterpene saponins from Pulsatilla patens var. multifida. J Nat Prod. 1999;62(2):233–237. https://doi.org/10.1021/np9802668
  • 65. Ye WC, Zhang QW, Hsiao WLW, Zhao SX, Che CT. Novel cytotoxic lupane-type glycosides from Pulsatilla chinensis. Planta Med. 2002;68:183–186. https://doi.org/10.1055/s-2002-20254
  • 66. Chen Z, Guan Y, Zhou L, Xu Y, Yang M, Liu H. Preparation and characterization of colon-targeted particles of Pulsatilla chinensis saponins. Nat Prod Commun. 2015;10(2):237–238.
  • 67. Li LD, Li WC, Liu CW, Shi WJ, Gong PT, Li JH, et al. Giardia intestinalis: effects of Pulsatilla chinensis extracts on trophozoites. Parasitol Res. 2012;111(5):1929–1935. https://doi.org/10.1007/s00436-012-3035-2
  • 68. Li WC, Shi WJ, Gu YF, Chen HL, Chen W, Zhang Y. Antibacterial effect of different extract of Pulsatilla chinensis (Bunge) Regel in vitro. Journal of Traditional Chinese Veterinary Medicine. 2011;2:38–40.
  • 69. Ma C. Treatment methods of traditional Chinese medicines against intestinal protozoan infections. In: Mehlhorn H, Zhongdao W, Ye B, editors. Treatment of human parasitosis in traditional Chinese medicine. Berlin: Springer; 2014. p. 11–21. (Parasitology Research Monographs; vol 6). https://doi.org/10.1007/978-3-642-39824-7_2
  • 70. Bi YL, Wang B, Huang BH, Zhang WT, Zhang YH. Antifungal activity of botanical extracts against Botrytis cinerea and Alternaria solani. Agricultural Science and Technology. 2011;12(6):862–864.
  • 71. Chen YQ, Xu QM, Liu YL, Li XR, Yang SL, Zhuge HX. Laboratory evaluation of the molluscicidal activity of Pulsatilla chinensis (Bunge) Regel saponins against the snail Oncomelania hupensis. Biomed Environ Sci. 2012;25(2):224–229. https://doi.org/10.3967/0895-3988.2012.02.015
  • 72. Chinese Pharmacopoeia Commission. Pharmacopoeia of the People’s Republic of China. Beijing: People’s Medical Publishing House; 2005.
  • 73. Kim Y, Kim SB, You YJ, Ahn BZ. Deoxypodophyllotoxin; the cytotoxic and antiangiogenic komponent from Pulsatilla koreana. Planta Med. 2002;68:268–271. https://doi.org/10.1055/s-2002-23140
  • 74. Cheon SA, Choi BK, Jeong CS, Li DW, Lee EB. The anti-inflammatory and analgesic actions of the fractions from Pulsatilla koreana root extract. Korean Journal of Clinical Pharmacy. 2000;31(2):174–184.
  • 75. Li W, Sun YN, Yan XY, Yang SY, Lee SJ, Byun HJ, et al. Isolation of nematicidal triterpenoid saponins from Pulsatilla koreana root and their activities against Meloidogyne incognita. Molecules. 2013;18:5306–5316. https://doi.org/10.3390/molecules18055306
  • 76. Chung SW, Chung CH, Lim SB, Kim JK, So EH. The antimicrobial effect of Pulsatilla koreana extracts to oral micro-organism. Journal of the Korean Academy of Periodontology. 2000;30(3):661. https://doi.org/10.5051/jkape.2000.30.3.661
  • 77. Ling Y, Lin Z, Zha W, Lian T, You S. Rapid detection and characterisation of triterpene saponins from the root of Pulsatilla chinensis (Bunge) Regel by HPLC-ESI-QTOF-MS/ MS. Phytochem Anal. 2016;27(3–4):174–183. https://doi.org/10.1002/pca.2613
  • 78. Lee KY, Cho YW, Park J, Lee DY, Kim SH, Kim YC, et al. Quality control of Pulsatilla koreana based on the simultaneous determination of triterpenoidal saponins by HPLC-ELSD and principal component analysis. Phytochem Anal. 2010;21:314–321. https://doi.org/10.1002/pca.1201
  • 79. Zhang Y, Bao J, Wang K, Jia X, Zhang C, Huang B, et al. Pulsatilla saponin D inhibits autophagic flux and synergistically enhances the anticancer activity of chemotherapeutic agents against HeLa cells. Am J Chin Med. 2015;43(8):1657–1670. https://doi.org/10.1142/S0192415X15500949
  • 80. Zhang QW, Ye WC, Che CT, Zhao SX. Triterpene saponins from Pulsatilla cernua. Acta Pharmaceutica Sinica. 2000;35(10):756–759.
  • 81. Jin ZL, Gao N, Zhou D, Chi MG, Yang XM, Xu JP. The extracts of Fructus Akebiae, a preparation containing 90% of the active ingredient hederagenin: serotonin, norepinephrine and dopamine reuptake inhibitor. Pharmacol Biochem Behav. 2012;100(3):431–439. https://doi.org/10.1016/j.pbb.2011.10.001
  • 82. Xu HJ, Shi XW, Ji X, Du YF, Zhu H, Zhang LT. Qualitative and quantitative determination of nine main active constituents in Pulsatilla cernua by high-performance liquid chromatography coupled to electrospray ionization tandem mass spectrometry. J Sep Sci. 2011;34:308–316. https://doi.org/10.1002/jssc.201000660
  • 83. Goyal S, Kumar S. Anti-anxiety activity studies of various extracts of Pulsatilla nigricans Stoerck. International Journal of Pharmaceutical Sciences and Drug Research. 2010;2(4):291–293.
  • 84. Nikolova M, Asenov A. Surface flavonoid aglycones in newly studied plant species. Nat Prod Res. 2006;20:103–106. https://doi.org/10.1080/14786410500046463
  • 85. Arcus M, Lilios G, Schröder V, Taralunga GH, Stoicescu RM, Dumitru IM. Natural compounds with benefits regarding the cardiovascular diseases. Journal of Environmental Protection and Ecology. 2015;16(1):333–339.
  • 86. Hegnauer R. Chemotaxonomie der Pflanzen. Stuttgart: Birkhäuser Verlag Basel; 1969.

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