Phytochemistry, pharmacology and traditional uses of different Epilobium species (Onagraceae): A review

Journal of Ethnopharmacology

Volumn 156, Issue , 2014, Pages 316-346

  Granica, Sebastian ^a   Piwowarski, Jakub P ^a   Czerwińska, Monika E ^a   Kiss, Anna K ^a  

^a MEDICAL UNIVERSITY OF WARSAW   (Poland)

Author keywords

Anti inflammatory; Anti proliferative; Benign prostate hyperplasia; Epilobium L. (Onagracae); Flavonoids; Oenothein B

Indexed keywords

FATTY ACID; FLAVONOID; MYCOPHENOLIC ACID; POLYPHENOL; STEROID; TANNIN DERIVATIVE; PLANT EXTRACT;

ANALGESIC ACTIVITY; ANTIFUNGAL ACTIVITY; ANTIINFLAMMATORY ACTIVITY; ANTIMICROBIAL ACTIVITY; ANTIOXIDANT ACTIVITY; ANTIPROLIFERATIVE ACTIVITY; BIOLOGICAL ACTIVITY; CHEMICAL COMPOSITION; CHEMICAL STRUCTURE; DRUG EFFECT; DRUG SAFETY; DRUG USE; EPILOBIUM; ETHNOPHARMACOLOGY; GASTROINTESTINAL TRACT; HUMAN; MEDLINE; MOLECULAR WEIGHT; PHYTOCHEMISTRY; REVIEW; SCOPUS; TRADITIONAL MEDICINE; WEB OF SCIENCE; CHEMISTRY; ONAGRACEAE; PHYTOTHERAPY; PROCEDURES;

EPILOBIUM; ETHNOPHARMACOLOGY; HUMANS; MEDICINE, TRADITIONAL; ONAGRACEAE; PHYTOTHERAPY; PLANT EXTRACTS;

EID: 84908452820     PISSN: 03788741     EISSN: 18727573     Source Type: Journal    
DOI: 10.1016/j.jep.2014.08.036     Document Type: Review

References (154)

1. Adelon, N.F., Mérat de Vaumartoise, F.V., L.J., R., 1819. Dictionaire des sciences médicales par une société de médecins et de chirurgiens. C. L. F. Panckoucke Paris.
2. Aiken, S.G., Dallwitz, M.J., Consaul, L.L., McJannet, C.L., Boles, R.L., Argus, G.W., Gillett, J.M., Scott, P.J., Elven, R., LeBlanc, M.C., Gillespie, L.J., Brysting, A.K., Solstad, H., Harris, J.G. 2012. Flora of the Canadian Arctic Archipelago. 〈http://nature.ca/aaflora/data/index.htm〉. (accessed 13.03.14).
3. Andre, A., Fehr, A., 2002. Gwich'in Ethonobotany: Plants Used by the Gwich'in for Food, Medicine, Shelter and Tools. Gwich'in Social and Cultural Institute and Aurora Research Institute, Inuvik.
4. Aoki, K., Maruta, H., Uchiumi, F., Hatano, T., Yoshida, T., Tanuma, S., 1995. A macrocircular ellagitannin, oenothein B, suppresses mouse mammary tumor gene expression via inhibition of poly(ADP-ribose) glycohydrolase. Biochemical and Biophysical Research Communications 210, 329-337.
5. Arredondo, M.F., Blasina, F., Echeverry, C., Morquio, A., Ferreira, M., Abin-Carriquiry, J.A., Lafon, L., Dajas, F., 2004. Cytoprotection by Achyrocline satureioides (Lam) D. C. and some of its main flavonoids against oxidative stress. Journal of Ethnopharmacology 91, 13-20.
6. Averett, J.E., Kerr, B.J., Raven, P.H., 1978. The flavonoids of Onagraceae, tribe Epilobieae: Epilobium sect. epilobium. American Journal of Botany 65, 567-570.
7. Averett, J.E., Raven, P.H., 1984. Flavonoids of Onagraceae. Annales of the Missouri Botanical Garden 71, 30-34.
8. Averett, J.E., Raven, P.H., Becker, H., 1979. The flavonoids of Onagraceae: tribe Epilobieae. American Journal of Botany 66, 1151-1155.
9. Barakat, H.H., Hussein, S.A.M., Marzouk, M.S., Merfort, I., Linscheid, M., Nawwar, M. A.M., 1997. Polyphenolic metabolites of Epilobium hirsutum. Phytochemistry 46, 935-941.
10. Barrett, S.A., Gifford, E.W., 1933. Indian life of the yosemite region: Miwok material culture. Bulletin of Milwaukee Public Museum 2, 174.
11. Bartfay, W.J., Bartfay, E., Johnson, J.G., 2012. Gram-negative and Gram-positive antibacterial properties of the whole plant extract of willow herb (Epilobium angustifolium). Biological Research for Nursing 14, 85-89.
12. Battinelli, L., Tita, B., Evandri, M.G., Mazzanti, G., 2001. Antimicrobial activity of Epilobium spp. extracts. Il Farmaco 56, 345-348.
13. Bejenaru, L.E., Olah, N., Mogosanu, G.D., Bejenaru, C., Neamtu, J., Popescu, H., 2009. Researches upon the free amino acids serine and threonine in five Epilobium species (Onagraceae). Farmacia 57, 485-491.
14. Bocek, B.R., 1984. Ethnobotany of Costanoan Indians, California, based on collections by John P. Harrington. Economic Botany 38, 240-255.
15. Borchardt, J.R., Wyse, D.L., Sheaffer, C.C., Kauppi, K.L., Fulcher, R.G., Ehlke, N.J., Biesboer, D.D., Bey, R.F., 2009. Antioxidant and antimicrobial activity ofseed from plants of the Mississippi river basin. Journal of Medicinal Plants Research 3, 707-718.
16. Bureau-of-American-Ethnology, B.o.A., 1928. Forty-fourth Annual Report of the Bureau of American Ethnlogy to the Secretary of the Smithsonian Institution. US Goverment Printing Office, Washington.
17. Campbell, G., 2004. Traditional Plant Use Study: Bent's Old Fort National Historic Site and Sand Creek Massacre Historic Site. University of Montana Missoula.
18. Celeste, M., 2008. Les effects pharmacologiques d'extraits d'Epilobium. Phytotherapie 6, 150-152.
19. Chen, Y., Yang, L., Lee, T.J., 2000. Oroxylin A inhibition of lipopolysaccharide-induced iNOS and COX-2 gene expression via suppression of nuclear factor-kappaB activation. Biochemical Pharmacology 59, 1445-1457.
20. n identification of chlorogenic acids. Journal of Agricultural and Food Chemistry 51, 2900-2911.
21. Coulson, S., Rao, A., Beck, S.L., Steels, E., Gramotnev, H., Vitetta, L., 2013. A phase II randomised double-blind placebo-controlled clinical trial investigating the efficacy and safety of ProstateEZE Max: a herbal medicine preparation for the management of symptoms of benign prostatic hypertrophy. Complementary Therapies in Medicine 21, 172-179.
22. Dechambre, A., Duval, M., Lereboullet, L., 1892. Dictionnaire usuel des sciences médicales. Libraire de l'Academie de Medicine, Paris.
23. Deschauer, T., 1945. Illustrated Phytotherapy. Thos. Deschauer. Thos. Deschauer Publications, Maywood.
24. Dicu, T., Postescu, I.D., Tatomir, C., Tamas, M., Dinu, A., Cosma, C., 2010. A novelmethod to calculate the antioxidant parameters of the redox reaction between polyphenolic compounds and the stable DPPH radical. Italian Journal of Food Science 22, 330-336.
25. Ducrey, B., Marston, A., Gohring, S., Hartmann, R.W., Hostettmann, K., 1997. Inhibition of 5 alpha-reductase and aromatase by the ellagitannins oenothein A and oenothein B from Epilobium species. Planta Medica 63, 111-114.
26. Ducrey, B., Wolfender, J.L., Marston, A., Hostettmann, K., 1995. Analysis of flavonol glycosides of 13 Epilobium species (Onagraceae) by LC-UV and thermospray LC-MS. Phytochemistry 38, 129-137.
27. Ebrahimzadeh, M.A., Pourmorad, F., Bekhradnia, A.R., 2008. Iron chelating activity, phenol and flavonoid content of some medicinal plants from Iran. African Journal of Biotechnology 7, 3188-3192.
28. Egasse, E., Dujardin-Beaumetz, G., 1889. Les plantes medicinales indigenes et exotiques. O. Doin, Paris.
29. Ellingwood, F., 1909. Miscellaneous. Ellingwood's Therapeutist 3, 57.
30. Ellingwood, F., 1919. American Materia Medica, Therapeutics and Pharmacognosy. Southwest School of Botanical Medicine, Bisbee.
31. Espín, J.C., Larrosa, M., García-Conesa, M.T., Tomás-Barberán, F., 2013. Biological significance of urolithins, the gut microbial ellagic acid-derived metabolites: the evidence so far. Evidence-based Complementary and Alternative Medicine, 2013.
32. Felter, H.W., 1909. A human tongue in specific diagnosis. Ellingwood's Therapeutist 3, 153.
33. Felter, H.W., 1922. The Eclectic Materia Medica, Pharmacology and Therapeutics. John K. Scudder, Cincinnati.
34. Felter, H.W., Lloyd, J.U., 1905. King's American Dispensatory. The Ohio Valley Company, Cincinnati.
35. Funatogawa, K., Hayashi, S., Shimomura, H., Yoshida, T., Hatano, T., Ito, H., Hirai, Y., 2004. Antibacterial activity of hydrolyzable tannins derived from medicinal plants against Helicobacter pylori. Microbiology and Immunology 48, 251-261.
36. Fyfe, J.F., 1903. Modern Materia Medica and Therapeutics. The Scudder Brothers Company, Cincinnati.
37. Gewali, M.B., 2008. Aspects of Traditional Medicine in Nepal. Institute of Natural Medicine, University of Toyama, Toyama.
38. Glen, A.T., Lawrie, W., Mclean, J., Younes, M.E.G., 1967. Triterpenoid constituents of rose-bay willow-herb. Journal of the Chemical Society C - Organic, 510-515.
39. Granica, S., Bazylko, A., Kiss, A.K., 2012. Determination of macrocyclic ellagitannin oenothein B in plant materials by HPLC-DAD-MS: method development and validation. Phytochemical Analysis 23, 582-587.
40. Gupta, R.K., Alsha., S.M.K., Layden, K., Haslam, E., 1982. The metabolism of gallic acid and hexahydroxydiphenic acid in plants.2. Esters of (S)-hexahydroxydiphenic acid with D-glucopyranose (C-4(1)). Journal of the Chemical Society-Perkin Transactions 1, 2525-2534.
41. Haddock, E.A., Gupta, R.K., Al-Shafi, S.M.K., Haslam, E., 1982. The metabolism of gallic acid and hexahydroxydiphenic acid in plants. Part 1. Introduction. Naturally occuring galloyl esters. Journal of the Chemical Society - Perkin Transactions 1, 2515-2524.
42. Harrison, F.O., 1909. Typhoid fever. Ellingwood's Therapeutist 3, 10-11.
43. Hevesi Toth, B., 2009. Phytochemical and In Vitro Biological Evaluation of Potentially Active in Epilobium Species (Ph.D. thesis). Department of Pharmacognosy, Budapest, Hungary.
44. Hevesi Toth, B., Balazs, A., Vukics, V., Szoke, E., Kery, A., 2006. Identification of Epilobium species and willow-herbs (Onagraceae) by HPLC analysis of flavonoids as chemotaxonomic markers. Chromatographia 63, S119-S123.
45. Hevesi Toth, B., Blazics, B., Kery, A., 2009a. Polyphenol composition and antioxidant capacity of Epilobium species. Journal of Pharmaceutical and Biomedical Analysis 49, 26-31.
46. Hevesi Toth, B., Houghton, P.J., Habtemariam, S., Kéry, Á., 2009b. Antioxidant and antiinflammatory effect of Epilobium parviflorum Schreb. Phytotherapy Research. 23, 719-724.
47. Hiermann, A., 1983. The investigation of active compounds from Epilobium species; 1. Communication: the flavonoid patterns. Scientia Pharmaceutica 51, 158-167.
48. Hiermann, A., 1993a. Concentrations of myricetin 3-O-β-D-glucuronide in Epilobium angustifolium during different vegetation stages and evaluation of its antiphlogistic activity. Planta Medica 59, A631.
49. Hiermann, A., 1993b. Flavonoids of Epilobium dodonaei. Fitoterapia 64, 471.
50. Hiermann, A., 1995. Phytochemical characterization of Epilobium angustifolium L. and its differentiation to other Epilobium species by TLC and HPLC. Scientia Pharmaceutica 63, 135-144.
51. Hiermann, A., Bucar, F., 1997. Studies of Epilobium angustifolium extracts on growth of accessory sexual organs in rats. Journal of Ethnopharmacology 55, 179-183.
52. Hiermann, A., Juan, H., Sametz, W., 1986. Influence of Epilobium extracts on prostaglandin biosynthesis and carrageenin induced oedema of the rat paw. Journal of Ethnopharmacology 17, 161-169.
53. Hiermann, A., Mayr, K., 1985. The investigation of active compounds from Epilobium species. 3rd communication: the occurrence of sitosterol derivatives in Epilobium angustifolium L. and Epilobium parviflorum Schreb. Scientia Pharmaceutica 53, 39-44.
54. Hiermann, A., Radl, B., 1998. Analysis of aromatic plant acids by capillary zone electrophoresis. Journal of Chromatography A 803, 311-314.
55. Hiermann, A., Reidlinger, M., Juan, H., Sametz, W., 1991. Isolation of the antiphlogistic principle from Epilobium angustifolium. Planta Medica 57, 357-360.
56. Hiermann, A., Schramm, H.W., Laufer, S., 1998. Anti-inflammatory activity of myricetin-3-O-beta-D-glucuronide and related compounds. Inflammation Research 47, 421-427.
57. Honegr, J., Pospíšilová, M., 2013. Determination of phenolic acids in plant extracts using CZE with on-line transient isotachophoretic preconcentration. Journal of Separation Science 36, 729-735.
58. Howard, G.Z., Mabry, T.J., 1972. Distribution of flavonoids in twenty-one species of Oenothera. Phytochemistry 11, 289-291.
59. Huneck, S., 1967. Triterpene 17. Uber die unverseifbaren neutralanteile aus Chamaenerion angustifolium (L.) Scop und Epilobium obscurum Schreb. Phytochemistry 6, 1149-1150.
60. Huttunen, S., Riihinen, K., Kauhanen, J., Tikkanen-Kaukanen, C., 2013. Antimicrobial activity of different Finnish monofloral honeys against human pathogenic bacteria. APMIS 121, 827-834.
61. Ivancheva, S., Manolova, N., Serkedjieva, J., Dimov, V., Ivanovska, N., 1992. Polyphenols from bulgarian medicinal plants with anti-infectious activity. In: Hemingway, P.E., Laks, P.E. (Eds.), Plant Polyphenols. Springer, New York, pp. 717-728.
62. Juan, H., Sametz, W., Hiermann, A., 1988. Anti-inflammatory effects of a substance extracted from Epilobium angustifolium. Agents and Actions 23, 106-107.
63. Kähkönen, M.P., Hopia, A.I., Vuorela, H.J., Rauha, J.P., Pihlaja, K., Kujala, T.S., Heinonen, M., 1999. Antioxidant activity of plant extracts containing phenolic compounds. Journal of Agricultural and Food Chemistry 47, 3954-3962.
64. Karakurt, S., Semiz, A., Celik, G., Gencler-Ozkan, A.M., Sen, A., Adali, O., 2013. Epilobium hirsutum alters xenobiotic metabolizing CYP1A1, CYP2E1, NQO1 and GPx activities, mRNA and protein levels in rats. Pharmaceutical Biology 51, 650-658.
65. Katalinic, V., Milos, M., Kulisic, T., Jukic, M., 2006. Screening of 70 medicinal plant extracts for antioxidant capacity and total phenols. Food Chemistry 94, 550-557.
66. King, J., 1856. American Eclectic Dispensatory. Moore, Wilstach, Keys, & Co, Cincinnati.
67. Kiss, A., Kowalski, J., Melzig, M.F., 2004. Compounds from Epilobium angustifolium inhibit the specific metallopeptidases ACE, NEP and APN. Planta Medica 70, 919-923.
68. Kiss, A., Kowalski, J., Melzig, M.F., 2006a. Effect of Epilobium angustifolium L. extracts and polyphenols on cell proliferation and neutral endopeptidase activity in selected cell lines. Pharmazie 61, 66-69.
69. Kiss, A., Kowalski, J., Melzig, M.F., 2006b. Induction of neutral endopeptidase activity in PC-3 cells by an aqueous extract of Epilobium angustifolium L. and oenothein B. Phytomedicine 13, 284-289.
70. Kiss, A.K., Bazylko, A., Filipek, A., Granica, S., Jaszewska, E., Kiarszys, U., Kos̈mider, A., Piwowarski, J., 2011. Oenothein B's contribution to the anti-inflammatory and antioxidant activity of Epilobium sp. Phytomedicine 18, 557-560.
71. Kiss, A.K., Granica, S., Stolarczyk, M., Melzig, M.F., 2012. Epigenetic modulation of mechanisms involved in inflammation: influence of selected polyphenolic substances on histone acetylation state. Food Chemistry 131, 1015-1020.
72. Kosalec, I., Kopjar, N., Kremer, D., 2013. Antimicrobial activity of willowherb (Epilobium angustifolium L.) leaves and flowers. Current Drug Targets 14, 986-991.
73. Kosalec, I., Zovko, M., Sankovic, K., Kremer, D., Pepeljnjak, S., 2008. Antioxidant and antimicrobial activity of willow herb (Epilobium angustifolium L.). Planta Medica 74, PA43.
74. Kosman, V.M., Shikov, A.N., Pozharitskaya, O.N., Makarov, V.G., Galambosi, B., Kauppinen, S., 2013. Variation of chemical composition of Epilobium angustifolium during fermentation. Planta Medica 79, PJ42.
75. Koziorowski, M., Mrozikiewicz, P.M., Ms̈cisz, A., Otta, H., Mikołajczak, P.Ł., Król, D., 2006. Czy Epilobium anigustifolium moẓe wspomagać leczenie i zapobiegać hormonozaleẓnym przerostom prostaty. Herba Polonica 52, 74.
76. Krajsek, S.S., Dermastia, M., Jogan, N., 2006. Determination key for central european Epilobium species based on trichome morphology. Botanica Helvetica 116, 169-178.
77. Kujawski, R., Derebecka-Hołysz, N., Mikołajczak, P.Ł., Mrozikiewicz, P.M., Bobkiewicz-Kozłowska, T., 2007. Investigation of the molecular mechanisms of action of natural herbal drugs in benign prostate hyperplesia. Acta Biochimica Polonica 54, 145.
78. Kujawski, R., Mrozikiewicz, P.M., Bogacz, A., Cichocka, J., Mikołajczak, P.Ł., Czerny, B., Bobkiewicz-Kozłowska, T., Grzes̈kowiak, E., 2010a. Influence of standardized extract of Epilobium angustifolium on estrogen receptor α and β expression in in vivo model. Ginekologia Polska 81, 600-605.
79. Kujawski, R., Mrozikiewicz, P.M., Mikołajczak, P.Ł., Kuzio, G., Bogacz, A., Cichocka, J., Bartkowiak-Wieczorek, J., Grzes̈kowiak, E., Uzar, I., Bobkiewicz-Kozłowska, T., Czerny, B., 2010b. Infuence of Epilobium angustifolium and Serenoa repens extracts on cytochrome 2D2 and 3A1 expression level in rats. Herba Polonica 56, 39-49.
80. Kujawski, R., Oẓarowski, M., Derebecka-Hołysz, N., Bartkowiak-Wieczorek, J., Bogacz, A., Karasiewicz, M., Mikołajczak, P.Ł., Bobkiewicz-Kozłowska, T., Mrozikiewicz, P.M., 2009. Effect of willow herb (Epilobium angustifolium L.) extract on gene expression of selected P450 cytochromes in rat liver - preliminary study. Herba Polonica 55, 52-64.
81. Kunduhoglu, B., Pilatin, S., Caliskan, F., 2011. Antimicrobial screening of some medicinal plants collected from Eskisehir, Turkey. Fresenius Environmental Bulletin 20, 945-952.
82. Larrosa, M., González-Sarrías, A., García-Conesa, M.T., Tomás-Barberán, F.A., Espín, J. C., 2006. Urolithins, ellagic acid-derived metabolites produced by human colonic microflora, exhibit estrogenic and antiestrogenic activities. Journal of Agricultural and Food Chemistry 54, 1611-1620.
83. Lee, M.H., Chiou, J.F., Yen, K.Y., Yang, L.L., 2000. EBV DNA polymerase inhibition of tannins from Eugenia uniflora. Cancer Letters 154, 131-136.
84. Lesuisse, D., Berjonneau, J., Ciot, C., Devaux, P., Doucet, B., Gourvest, J.F., Khemis, B., Lang, C., Legrand, R., Lowinski, M., Maquin, P., Parent, A., Schoot, B., Teutsch, G., Chodounska, H., Kasal, A., 1996. Determination of oenothein B as the active 5-alpha-reductase-inhibiting principle of the folk medicine Epilobium parvi-florum. Journal of Natural Products 59, 490-492.
85. Maruta, H., Matsumura, N., Tanuma, S., 1997. Role of (ADP-ribose)n catabolism in DNA repair. Biochemical and Biophysical Research Communications 236, 265-269.
86. Maruta, H., Okita, N., Takasawa, R., Uchiumi, F., Hatano, T., Tanuma, S., 2007. The involvement of ATP produced via (ADP-Ribose)n in the maintenance of DNA replication apparatus during DNA repair. Biological and Pharmaceutical Bulletin 30, 447-450.
87. Miyamoto, K., Kishi, N., Koshiura, R., Yoshida, T., Hatano, T., Okuda, T., 1987. Relationship between the structures and the antitumor activities of tannins. Chemical and Pharmaceutical Bulletin 35, 814-822.
88. Miyamoto, K., Koshiura, R., Hatano, T., Yoshida, T., Okuda, T., 1992. Structures and activities of tannins in crude drugs - host-mediated antitumor activity. Journal of Pharmacobiodynamics 15, S6.
89. Miyamoto, K., Nomura, M., Murayama, T., Furukawa, T., Hatano, T., Yoshida, T., Koshiura, R., Okuda, T., 1993a. Antitumor activities of ellagitannins against sarcoma-180 in mice. Biological and Pharmaceutical Bulletin 16, 379-387.
90. Miyamoto, K., Nomura, M., Sasakura, M., Matsui, E., Koshiura, R., Murayama, T., Furukawa, T., Hatano, T., Yoshida, T., Okuda, T., 1993b. Antitumor activity of oenothein B, a unique macrocyclic ellagitannin. Japanese Journal of Cancer Research 84, 99-103.
91. Moore, M., 1994. Herbal Repertory in Clinical Practice. Southwest School of Botanical Medicine, Bisbee.
92. Moore, M., 1997. Specific Indications for Herbs in General Use. Southwest School of Botanical Medicine, Bisbee.
93. Morquio, A., Rivera-Megret, F., Dajas, F., 2005. Photoprotection by topical application of Achyrocline satureioides ('Marcela'). Phytotherapy Research 19, 486-490.
94. Nawwar, M.A.M., Marzouk, M.S., Nigge, W., Linscheid, M., 1997. High-performance liquid chromatographic electrospray ionization mass spectrometric screening for polyphenolic compounds of Epilobium hirsutum - the structure of the unique ellagitannin epilobamide A. Journal of Mass Spectrometry 32, 645-654.
95. Nomura, M., Tsukada, H., Ichimatsu, D., Ito, H., Yoshida, T., Miyamoto, K., 2005. Inhibition of epidermal growth factor-induced cell transformation by tannins. Phytochemistry 66, 2038-2046.
96. Nowak, R., Krzaczek, T., 1998a. Farmakognostyczne badania ziela Epilobium angustifolium L. and Epilobium parviflorum L Schreb. Herba Polonica 44, 5-9.
97. Nowak, R., Krzaczek, T., 1998b. Sterole w zielu Epilobium angustifolium L. Herba Polonica 44, 297-299.
98. Okuda, T., Yoshida, T., Hatano, T., 1989. Ellagitannins as active constituents of medicinal plants. Planta Medica 55, 117-122.
99. Okuyama, S., Makihata, N., Yoshimura, M., Amakura, Y., Yoshida, T., Nakajima, M., Furukawa, Y., 2013. Oenothein B suppresses lipopolysaccharide (LPS)-induced inflammation in the mouse brain. International Journal of Molecular Sciences 14, 9767-9778.
100. Petrova, M.F., Pukhalskaya, E.C., Gotinskaya, L.G., 1974. Problems of Chemotherapy of Tumors. Russian Academy of Sciences, Moscow-Kiev.
101. Pourmorad, F., Ebrahimzadeh, M.A., Mahmoudi, M., Yasini, S., 2007. Antinociceptive activity of methanolic extract of Epilobium hirsutum. Pakistan Journal of Biological Sciences 10, 2764-2767.
102. Pukhalskaya, E.C., Chernyakhovskaya, I.Y., Petrova, M.F., Denisova, S.I., Alieva, T.A., 1975. Macromolecular antitumor agents from Chamaenerium angustifolium. Neoplasma 22, 29-37.
103. Pukhalskaya, E.C., Petrova, M.F., Kibalchin, P.N., Denisova, S.I., Alieva, T.A., Perepelkina, L.D., 1970. Isolation of a polymer from Chamaenerium angustifolium and studies on its antitumor activity. Antibiotics 9, 782-785.
104. Puringer, K., 1923. Beitrage zur vergleichenden pflanzenchemie VIII. Uber Chamaenerium angustifolium Scop. Monatschefte fur Chemie 44, 256-260.
105. Rakhmadieva, S.B., Bikbulatova, T.N., Chumbalov, T.K., 1979. Isovalone acid - is a new acid from tanning matter of Epilobium hirsutum. Chemistry of Natural Compounds 15, 647.
106. Ramstead, A.G., Schepetkin, I.A., Quinn, M.T., Jutila, M.A., 2012. Oenothein B, a cyclic dimeric ellagitannin isolated from Epilobium angustifolium, enhances IFNγ production by lymphocytes. PLoS One 7, e50546.
107. Rauha, J.P., Remes, S., Heinonen, M., Hopia, A., Kähkönen, M., Kujala, T., Pihlaja, K., Vuorela, H., Vuorela, P., 2000. Antimicrobial effects of Finnish plant extracts containing flavonoids and other phenolic compounds. International Journal of Food Microbiology 56, 3-12.
108. Raven, P.H., 1976a. Flora Europea. Cambridge University Press, London.
109. Raven, P.H., 1976b. Generic and sectional delimitation in Onagraceae, Tribe Epilobieae. Annals of the Missouri Botanical Garden 63, 326-340.
110. Raymond, M., 1945. Notes ethnobotaniques sur les tete-de-boule de manouan. Contributions de l'Institut botanique l'Universite de Montreal 55, 113-134.
111. Reutter de Rosemont, L., 1923. Traite de mariere medicale, drogues vegetales, drogues animales, et de chimie vegetale, Librairie J.-B. Bailliere et Fils.
112. Reynaud, J., Becchi, M., Carrier, M., Raynaud, J., 1982. Les aglycones flavoniques d'Epilobium angustifolium L. (Onagracees). Plantes Medicinales et Phytotherapie 24, 120-121.
113. Rolla, L.T., 1907. The Eclectic Practice of Medicine. The Scudder Brothers Company, Cincinnati.
114. Roman, I., Rusu, M.A., Puicə, C., Borşa, M., 2010. Citotoxic effects of three species of Epilobium (Onagraceae) herbal extracts in rats. Studia Universitatis Vasile Goldis Arad, Seria Stiintele Vietii 20, 19-23.
115. Rousseau, J., 1947. Ethnobotanique abenakise. Archives de Folklore 11, 164.
116. Ruszová, E., Cheel, J., Pávek, S., Moravcová, M., Hermannová, M., Matějková, I., Spilková, J., Velebný, V., Kubala, L., 2013. Epilobium angustifolium extract demonstrates multiple effects on dermal fibroblasts in vitro and skin photoprotection in vivo. General Physiology and Biophysics 32, 347-359.
117. Rza¸dkowska-Bodalska, H., Żuk, J., Olechnowicz-Ste¸pień, W., 1987. Badanie ziela wierzbownicy drobnokwiatowej (Epilobium parviflorum Schreb.). Herba Polonica 23, 179-184.
118. Sakagami, H., Jiang, Y., Kusama, K., Atsumi, T., Ueha, T., Toguchi, M., Iwakura, I., Satoh, K., Ito, H., Hatano, T., Yoshida, T., 2000. Cytotoxic activity of hydrolyzable tannins against human oral tumor cell lines-a possible mechanism. Phytomedicine 7, 39-47.
119. Schepetkin, I.A., Kirpotina, L.N., Jakiw, L., Khlebnikov, A.I., Blaskovich, C.L., Jutila, M. A., Quinn, M.T., 2009. Immunomodulatory activity of oenothein B isolated from Epilobium angustifolium. Journal of Immunology 183, 6754-6766.
120. Schmid, D., Gruber, M., Piskaty, C., Woehs, F., Renner, A., Nagy, Z., Kaltenboeck, A., Wasserscheid, T., Bazylko, A., Kiss, A.K., Moeslinger, T., 2012. Inhibition of NF-kappaB-dependent cytokine and inducible nitric oxide synthesis by the macrocyclic ellagitannin oenothein B in TLR-stimulated RAW 264.7 macrophages. Journal of Natural Products 75, 870-875.
121. Seeram, N.P., Aronson, W.J., Zhang, Y., Henning, S.M., Moro, A., Lee, R.P., Sartippour, N., Harris, D.M., Rettig, M., Suchard, M.A., Pantuck, A.J., Belldegrun, A., Heber, D., 2007. Pomegranate ellagitannin-derived metabolites inhibit prostate cancer growth and localize to the mouse prostate gland. Journal of Agricultural and Food Chemistry 55, 7732-7737.
122. Seeram, N.P., Henning, S.M., Zhang, Y.J., Suchard, M., Li, Z.P., Heber, D., 2006. Pomegranate juice ellagitannin metabolites are present in human plasma and some persist in urine for up to 48 hours. Journal of Nutrition 136, 2481-2485.
123. Sennikov, A.N., 2011. Chamerion or Chamaenerion (Onagraceae)? The old story in new words. Taxon 60, 1485-1488.
124. Shikov, A.N., Poltanov, E.A., Dorman, H.J.D., Makarov, V.G., Tikhonov, V.P., Hiltunen, R., 2006. Chemical composition and in vitro antioxidant evaluation of commercial water-soluble willow herb (Epilobium angustifolium L.) extracts. Journal of Agricultural and Food Chemistry 54, 3617-3624.
125. Shikov, A.N., Pozharitskaya, O.N., Ivanova, S.A., Makarov, V.G., Tikhonov, V.P., Galambosi, B., 2010. Improved and validated HPTLC method for quantification of oenothein B and its use for analysis of Epilobium angustifolium L. Journal of Planar Chromatography - Modern TLC 23, 70-74.
126. Slacanin, I., Marston, A., Hostettmann, K., Delabays, N., Darbellay, C., 1991. Isolation and determination of flavonol glycosides from Epilobium species. Journal of Chromatography 557, 391-398.
127. Smith, D., 1855. Indian Physician: A Complete Guide to Health. Curtiss & White, Printers, Utica.
128. Smith, H.H., 1923. Ethnobotany of the Menomini Indians. Bulletin of the Public Museum of the City of Milwaukee 4, 40.
129. Smith, H.H., 1933. Ethnobotany of the forest Potawatomi indians. Bulletin of the Public Museum of the City of Milwaukee 7, 63-64.
130. Štajner, D., Popović, B.M., Boža, P., 2007. Evaluation of willow herb's (Epilobium angustofolium L.) antioxidant and radical scavenging capacities. Phytotherapy Research 21, 1242-1245.
131. Steenkamp, V., Gouws, M.C., Gulumian, M., Elgorashi, E.E., Van Staden, J., 2006. Studies on antibacterial, anti-inflammatory and antioxidant activity of herbal remedies used in the treatment of benign prostatic hyperplasia and prostatitis. Journal of Ethnopharmacology 103, 71-75.
132. Stef, D.S., Gergen, I., Traşcə, T.I., Hərmənescu, M., Lavinia, Ş., Ramona, B., Hegheduş, M.G., 2009. Total antioxidant and radical scavenging capacities for different medicinal herbs. Romanian Biotechnological Letters 14, 4704-4709.
133. Stef, D.S., Iosif, G., Ioan-Trasca, T., Stef, L., Pop, C., Harmanescu, M., Biron, R., Pet, E., 2010. Evaluation of 33 medicinal plant extracts for the antioxidant capacity and total phenols. Journal of Food, Agriculture and Environment 8, 207-210.
134. Stolarczyk, M., 2013. Wpływ standaryzowanych wycia¸gów z ziela róẓnych gatunków rodzaju Epilobium na proliferacje¸ komórek raka prostaty hormonozaleẓnego (LNCaP) i wydzielanie antygenu gruczołu krokowego (PSA). Poszukiwanie zwia¸zów czynnych (Ph.D. thesis). Department of Pharmacognosy and Molecular Basis of Phytotherapy, Warsaw, Poland.
135. Stolarczyk, M., Naruszewicz, M., Kiss, A.K., 2013a. Extracts from Epilobium sp. herbs induce apoptosis in human hormone-dependent prostate cancer cells by activating the mitochondrial pathway. Journal of Pharmacy and Pharmacology 65, 1044-1054.
136. Stolarczyk, M., Piwowarski, J.P., Granica, S., Stefanska, J., Naruszewicz, M., Kiss, A.K., 2013b. Extracts from Epilobium sp. herbs, their components and gut microbiota metabolites of Epilobium ellagitannins, urolithins, inhibit hormone-dependent prostate cancer cells-(LNCaP) proliferation and PSA secretion. Phytotherapy Research 27, 1842-1848.
137. Tita, B., Abdel-Haq, H., Vitalone, A., Mazzanti, G., Saso, L., 2001. Analgesic properties of Epilobium angustifolium, evaluated by the hot plate test and the writhing test. Il Farmaco 56, 341-343.
138. Treben, M., 1984. Health through God's pharmacy, Steyr. Wilhem Ennsthaler.
139. Turner, N.J., Bouchard, R., Kennedy, D.I.D., 1980. Ethnobotany of the Okanagan-Colville Indians of British Columbia and Washington, British Columbia Provincial Museum.
140. van Wyk, B.E., Wink, M., 2004. Ros̈liny lecznicze s̈wiata. Ilustorwany przewodnik. MedPharmPOLSKA, Wrocław, Polska.
141. Velasco, L., Goffman, F.D., 1999. Tocopherol and fatty acid composition of twenty-five species of Onagraceae Juss. Botanical Journal of the Linnean Society 129, 359-366.
142. Villa, S., Prahoveanu, E., Esanu, V., Mihaila, V., Pintilie, M., Niculescu, M., Teoteoi, N., Colceru, S., 1989. L'action d'un extrait de Chamenerion angustifolium sur l'infection experimentale a virus de la grippe chez la souris. Revue Roumaine de Medecine - Virology 40, 120-132.
143. Vitali, F., Fonte, G., Saija, A., Tita, B., 2006. Inhibition of intestinal motility and secretion by extracts of Epilobium spp. in mice. Journal of Ethnopharmacology 107, 342-348.
144. Vitalone, A., Bordi, F., Baldazzi, C., Mazzanti, G., Saso, L., Tita, B., 2001. Antiproliferative effect on a prostatic epithelial cell line (PZ-HPV-7) by Epilobium angustifolium L. Il Farmaco 56, 483-489.
145. Vitalone, A., McCroll, J., Thome, D., Costa, L.G., Tita, B., 2003. Characterization of the effect of Epilobium extracts on human cell proliferation. Pharmacology 69, 79-87.
146. Vogl, S., Picker, P., Mihaly-Bison, J., Fakhrudin, N., Atanasov, A.G., Heiss, E.H., Wawrosch, B., Reznicek, G., Dirsch, V.M., Saukel, J., Kopp, B., 2013. Ethnopharmacological in vitro studies on Austria's folk medicine - an unexplored lore in vitro anti-inflammatory activities of 71 Austrian traditional herbal drugs. Journal of Ethnopharmacology 149, 750-771.
147. Voynova, E., Dimitrova, S., Naydenova, E., Karadjov, P., 1991. Inhibitory action of extracts of Maclura aurantiaca and Epilobium hirsutum on tumour models in mice. Acta Physiologica et Pharmacologica Bulgarica 17, 50-52.
148. Wagner, W.L., Hoch, P.C. 2005. Onagraceae, the evening primrose family website. 〈http://botany.si.edu/onagraceae/index.cfm〉 (accessed 31.10.13).
149. Wagner, W.L., Hoch, P.C., Raven, P.H., 2007. Revised classification of the Onagraceae. Systematic Botany Monographs 83, 1-243.
150. Wang, C.C., Chen, L.G., Yang, L.L., 1999. Antitumor activity of four macrocyclic ellagitannins from Cuphea hyssopifolia. Cancer Letters 140, 195-200.
151. Whiting, A.F., 1939. Ethnobotany of the Hopi. Museum of Northern Arizona Bulletin 15, 33.
152. Wichtl, M., 2004. Herbal Drugs and Phytopharmaceuticals. Medpharm Scientific Publishers, Wurzburg.
153. Wojdyło, A., Oszmiański, J., Czemerys, R., 2007. Antioxidant activity and phenolic compounds in 32 selected herbs. Food Chemistry 105, 940-949.
154. Yoshimura, M., Akiyama, H., Kondo, K., Sakata, K., Matsuoka, H., Amakura, Y., Teshima, R., Yoshida, T., 2013. Immunological effects of oenothein B, an ellagitannin dimer, on dendritic cells. International Journal of Molecular Sciences 14, 46-56.