DNA- Binding, Biological Activities, and Chemical Composition of Wild Growing Epilobium angustifolium L. Extracts from Canakkale, Turkey

Aysema Sayık; Ayşe Sergüzel Yusufoğlu; Leyla Açık; Gülen Türker; Betül Aydın; Leyla Arslan

doi:10.18596/jotcsa.319789

Research Article

Year 2017, Volume: 4 Issue: 3, 811 - 840, 03.08.2017

Aysema Sayık Ayşe Sergüzel Yusufoğlu Leyla Açık Gülen Türker Betül Aydın Leyla Arslan

https://doi.org/10.18596/jotcsa.319789

Cited By: 11

Abstract

References

1. Kumar S, Yadav A, Yadav M, Yadav J.P. BMC Research Notes, 2017, 10:60.
2. Hiermann A, Juan H, Sametz W. Influence of Epilobium extracts on prostaglandin biosynthesis and carrageenin induced oedema of the rat paw. Journal of Ethnopharmacology,1986, Aug; 17 (2):161-9.
3. Juan H, Sametz W, Hiermann A. Anti-inflammatory effects of a substance extracted from Epilobium angustifolium. Agents and Actions, 1988, 23: 106-107.
4. Vitali F, Fonte G, Saija A, Tita B. Inhibition of intestinal motility and secretion by extracts of Epilobium spp. in mice. Journal of Ethnopharmacology, 2006, Oct., 11; 107 (3):342-8.
5. Tita B, Abdel-Haq H, Vitalone A, Mazzanti G, Saso L. Analgesic properties of Epilobium angustifolium, evaluated by the hot plate test and the writhing test., Farmaco, 2001, May-Jul; 56(5-7):341-3.
6. Hiermann A, Reidlinger M, Juan H, Sametz W. Isolation of the antiphlogistic principle from Epilobium angustifolium. Planta Med., 1991, Aug; 57(4): 357-60.
7. Hiermann A, Schramm H.W, Laufer S. Anti-inflammatory activity of myricetin-3-O-beta-D-glucronide and related compounds. Inflamm. Res., 1998, 47, 421-427.
8. Stolarczyk M, Naruszewicz M, Kiss A.K. Extracts from Epilobium sp. Herbs induce apoptosis in human hormone-dependent prostate cancer cells by activating the mitochondrial pathway. Extracts from Epilobium sp. Herbs induce apoptosis in human hormone-dependent prostate cancer cells by activating the mitochondrial pathway. J .Pharm Pharmacol, 2013, Jul; 65(7):1044-54.
9. Ducrey B, Marston A, Gohring S, Hartmann R.W, Hostettmann K. Inhibition of 5alpha-reductaseandaromatasebytheellagitanninsoenothein A andoenotheinBfrom Epilobium species. PlantaMedica, 1997, 63,111–114.
10. Kiss A, Kowalski J, Melziq M.F. Phytomedicine, 2006, Induction of neutral endopeptidase activity in PC-3 cells by an aqueous extract of Epilobium angustifolium L. and oenothein B., Mar; 13(4):284-9.
11. Vitalone A, McColl J, Thome D, Costa L.G, Tita B. Characterization of the effect of Epilobium extracts on human cell proliferation. Pharmacology,2003, Oct; 69(2):79-87.
12. Committtee on Herbal Medicinal Products, 10 March 2015 EMA/HMPC/712510/2014, Assessment report on Epilobium angustifolium L. and /or Epilobium parviflorum Schreb. herba. Based on Article 16d(1), Article 16f and Article 16h of Directive 2001/83/EC as amended (traditional use). 13. Oenothein medicaments. Patent publish: US6528490 B2 14. Sakagami H, Jiang Y, Kusama K, Atsumi T, Ueha T, Toguchi M, Iwakura I, Satoh K, Ito H, Hatano T, Yoshida T. Cytotoxic activity of hydolyzable tannins against human oral tumor cell lines—a possible mechanism. Phytomedicine, 2000, Mar; 7(1):39-47. 15. Miyamoto K, Nomura M, Sasakura M, Matsui E, Koshiura R, Murayama T, Furukawa T, Hatano T, Yoshida T, Okuda T. Antitumor activity of oenothein B, a unique macrocycic ellagitannin. Jpn J. Cancer Res., 1993, Jan; 84(1):99-103.
16. Miyamoto Nomura K. M, Murayama T, Furukawa T, Hatano T, Yoshida T, Koshiura R, Okuda T. Antitumor activities of ellagitannins against sarcoma-180 in mice. Biol. Pharm. Bull, 1993, Apr; 16(4):379-87.
17. Rauha J. P, Remes S, Heinonen Hopia M, Kahkönen A, Kujala M, Pihlaja T, Vuorela K, Vuorela H. P. Antimicrobial effects of finnish plant extracts containing flavonoids and other phenolic compounds., Int. J. Food Micobiol., 2000, May 25;56(1):3-12.
18. Battinelli L, Tita B, Evandri M.G, Mazzanti G. Antimicrobial activity of Epilobium spp extracts. Farmaco,2001, May-Jul;56(5-7):345-8.
19. Kosalec I, Kopjar N, Kremer D. Antimicrobial activity of Willowherb (Epilobium angustifolium L.) leaves and flowers. Curr Drug Targets, 2013, Aug;14(9):986-91.
20. Webster D, Taschereau P, Belland R.J, Sand C, Rennie R.P. Antifungal activity of medicinal plant extracts; preliminary screening studies. Journal of Ethnopharmacology, 2008, Jan 4; 115(1):140-6.
21. Kahkönen M.P, Hopia A.I, Vuorela H.J, Rauha J.P, Pihlaja K, Kujala T.S, Heinonen M. Antioxidant activity of plant extracts containing phenolic compounds. J. Agric. Food Chem., 1999, Oct; 47(10):3954-62.
22. Stajner D, Popovi B.M, Bo_a P. Evaluation of willow herb’s (Epilobium angustifolium L.) antioxidant and radical scavenging capacities.Phytother Res., 2007, Jul 27.
23. Kiss A.K, Bazylko A, Filipek A, Granica S, Jaszewska E, Kiarszys U, Kosmider A, Piwowarski J. Oenothein B’s contribution to the anti-inflammatory and antioxidant activity of Epilobium sp. Phytomedicine, 2011, Volume 18, Issue 7, Pages 557-560.
24. Schepetkin I.A, Kirpotina L.N, Jakiw L, Khlebnikov A.I, Blashkovich C.L, Jutila M.A, Quinn M.T. Immunomodulatory Activity of Oenothein B Isolated from Epilobium angustifolium. 2009, The Journal of Immunology, Nov 15;183(10):6754-66.
25. Myagmar B.E, Aniya Y. Free radical scavenging action of medicinal herbs from Mongolia. Phytomedicine, 2000, Volume 7, Issue 3, Pages 221-229.
26. Miyamoto K, Murayama T, Nomura M, Hatano T, Yoshida T, Furukawa T, Koshiura R, Okuda T. Antitumor activity and interleukin-1 induction by tannins. Anticancer Res., 1993, Jan-Feb;13(1):37-42.
27. http://montana.plant-life.org/species/epilob_angus.html (accessed 10.08.2015)
28. Dzwonko Z, Loster S, Gawronski S. Impact of fire severity on soil properties and the development of tree and shrub species in a Scots pine moist forest site in southern Poland. Foretst Ecology and Management, 2015, Volume 342, 15 April, Pages 56–63.
29. Gurova K.New hopes from old drugs: revisiting DNA-binding small molecules as anticancer agents. Future Oncol. 2009, 5(10), 1685.
30. Cancer Fact Sheet No:297 World Health Organization. February 2014. Retrieved 10 June 2014.
31. National Cancer Institute, Defining Cancer. Retrieved 10 June 2014.
32. Braca A, Tommasi N.D, Bari L.D, Pizza C, Politi M, Morelli I. Antioxidantprinciples from Bauhinia terapotensis. , J. Nat. Prod., 2001, 64, 892–895.
33. Siddhuraju P, Becker K. Antioxidant properties of various solvent extracts of total phenolic constituents from three different agroclimatic regions of Drum- stick tree (Moringa olifera Lam.) leaves. 2003, J. Agric. Food Chem.,51 (), pp. 2144–2155.
34. Dinis T.C.P, Madeira V.M.C, Almeida L.M. Action of phenolic derivatives (acetoaminophen, salycilate and 5-aminosalycilate) as inhibitors of membrane lipid peroxidation and as peroxyl radical scavengers. Arch. Biochem. Biophys., 1994, 315, pp. 161–169.
35. Hertog M.G.L, Hollman P.C.H, Venema D.P. Optimization of a quantitative HPLC determination of potentially anticarcinogenic flavonoids in vegetables and fruits. J. Agric. Food Chem., 1992, 40, 1591.
36. Hossain Z, Huq F. Studies on the interaction between Ag+ and DNA. Journal of Inorganic Biochemistry, 2002, 91, 398-404.
37. Cutter C. Antimicrobial effect of herb extracts against Escherichia coli 0157:h7, Listeria monocytogenes and Salmonella typhimurium associated with beef. Food Prot. 2000, 63:601-607.
38. Hao Y.Y, Brackett R.E, Doyle M.P. Efficacy of plant extracts in inhibiting Aeromonas hydrophilia and Listeria monocytogenes in refrigerated cooked poultry. Food Microbiol. 1998, 15:367-378.
39. Puupponen Pimia R, Nohynek L., Meiier C, Kahkonen M, Heinonen M, Hopia A, Oksman Caldentey K.M. Antimicrobial properties of phenolic compounds from berries. J. Appl. Microbiol. 2001, 90:494-507.
40. American Journal of Pathology, news release, Nov. 27, 2012.
41. Yu X, Zhao M, Liu F, Zeng S, Hu J. Identification of 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one as a strong antioxidant in glucose–histidine Maillard reaction products. Food Research International, 2013, Volume 51, Issue 1, Pages 397-403.
42. Who. int /Concise International Chemical Assessment Document 21/2-Furaldehyde, 2000.
43. Petrovic´ V, Car Zˇ, Prugovecˇki B. S, Tomic D, Matkovic´ C. Synthesis of Acylated Methyl 2-Acetamido-2-Deoxy-a-D-Mannopyranosides Journal of Carbohydrate Chemistry, 2006, 25:685–695.
44. Mahadevan A, Hopper W. Degradation of catechin by Bradyrhizobium japonicum Biodegradation 1997, 8 (3): 159–165.
45. Api A.M. Toxicological profile of diethyl phthalate: a vehicle for fragrance and cosmetic ingredients. Food and Chemical Toxicology, 2001, 39 (2): 97–108.
46. Wilt T, Ishani A, MacDonald R, Stark G, Mulrow C, Lau J. Beta-sitosterols for benign prostatic hyperplasia. The Cochrane Library 2000, (2): CD001043.
47. Kim T. H, Lim H. J, Kim M. S, Lee M. S. Dietary supplements for benign prostatic hyperplasia: An overview of systematic reviews. Maturitas 2012, 73 (3): 180–5.
48. Sundararaman P, Djerassi C. A convenient synthesis of progesterone from stigmasterol. J Org Chem. 1977, 42 (22): 3633–3634.
49. Rudkowska I, AbuMweis S.S, Nicolle C, Jones P. J. Cholesterol-lowering efficacy of plant sterols in low-fat yogurt consumed as a snack or with a meal. J Am Coll Nutr 2008, . 27 (5): 588–95.
50. "Ellagic acid". American Cancer Society. November 2008. Retrieved August 2014.
51. U.S. Food and Drug Administration, 187 Fake Cancer 'Cures' Consumers Should Avoid, Accessed June 17, 2008.
52. Shivappurkar M, Galati and Stoner. Inhibition of N-nitrosobenzylmethylamine anda DNA-binding in cultured rat esophagus by ellagic acid. Carcinogenesis , 1988, 9 (7): 1313–1316.
53. Mandal and Stoner, Stoner G.D. Inhibition of N-nitrosobenzymethylamine-induced esophageal tumorigenesis in rats by ellagic acid.Carcinogenesis, 1990, 11 (1): 55–61.
54. Granica S, Piwoworski J.P, Czerwinska M.E, Kiss A. K. Phytochemistry, pharmacologyandtraditionalusesofdifferent Epilobium species (Onagraceae):Areview. Journal of Ethnopharmacology, 2014, 156, 316-346.
55. Noll D. M, Mason T. M, Miller P. S. Formation and Repair of Interstrand Cross-Links in DNA. Chem Rev. 2006, 106(2): 277-301.
56.www.cancer.org(http://www.cancer.org/treatment/treatmentsandsideeffects/treatmenttypes/chemotherapy/chemotherapyprinciplesanin-depthdiscussionofthetechniquesanditsroleintreatment/chemotherapy-principles-types-of-chemo-drugs ( accessed 18.09.2015).
57. Saeed N, Khan M.R, Shabbir M. Antioxidant activity, Total phenolic and Total Flavonoid Contents of Whole Plant Extracts Torilis lepthophylla.BMC Complementary & Alternative Medicine, 2012, 12:221.
58. Grattan Bruce Jr J. Nutrients, Plant Sterols as Anticancer Nutrients: Evidence for Their Role in Breast Cancer. 2013, Feb; 5(2): 359–387.
59. Martins P, Jesus J, Santos S, Raposo L. R, Roma-Rodrigues C, Baptista P. V. Heterocyclic anticancer compounds: Recent advances and the paradigm shift towards the use of nanomedicine’s tool box. Fernandes,A. R. , 2015, Molecules, 2015, 20, 16852-16891; doi:10.3390/molecules200916852.
60. Kosalec I, Zovko M, Sankovic K, Kremer D, Pepeljnjak S. Antioxidant and antimicrobial activity of willow herb (Epilobium angustifolium L.)Planta Med. 2008: 74 PA43 DOI: 10.1055/s-0028-1084041.
61. Rasoanaivo P, Wright C. W, Willcox M.L, Gilbert B. Whole plant extracts versus single compounds fort he treatment of malaria: Synergy and positive interactions. Malaria Journal, 2011, 10(suppl 1):54.

DNA- Binding, Biological Activities, and Chemical Composition of Wild Growing Epilobium angustifolium L. Extracts from Canakkale, Turkey

Year 2017, Volume: 4 Issue: 3, 811 - 840, 03.08.2017

Aysema Sayık Ayşe Sergüzel Yusufoğlu Leyla Açık Gülen Türker Betül Aydın Leyla Arslan

https://doi.org/10.18596/jotcsa.319789

Cited By: 11

Abstract

The usage of Epilobium
angustifolium L. in folk medicine against prostate and skin diseases encouraged
us to investigate pBR322 DNA-binding ability, biological activities and
chemical composition of wild growing Epilobium
angustifolium L.’s methanolic, ethanolic and aqueous extracts from
Canakkale, Turkey. DNA-binding activity was studied by agarose gel
electrophoresis and chemical composition via GC, GC-MS, HPLC, LC-MS, ICP-MS and
AAS. Literature survey indicates no data on pBR322 plasmid DNA interaction of Epilobium species which is an important
criteria for being a potential anticancer agent. Antibacterial and antifungal
effects were tested against 11 bacterias and 3 fungis and compared with
ampicillin, chloramphenicol and ketokanozol by agar well diffusion techniques. Total
phenolic content was found by Folin-Ciocalteu method and antioxidant activity
was obtained by DPPH and Fe (II)-FZ (ferric-ferrozine) methods. This plant is rich of flavonoids, hormones,
fatty and phenolic acids. Si, K,
Mg, P and Mn were the main inorganic elements. Epilobium angustifolium L. with its high DNA-binding activity and
rich chemical composition can be a good potential anticancer, antimicrobial and
antioxidant prodrug.

Keywords

DNA-Binding activity, pBR322 plasmid DNA-Binding, , Epilobium angustifolium L. extracts, cancer therapeutic, chemical analysis¬¬¬

References

1. Kumar S, Yadav A, Yadav M, Yadav J.P. BMC Research Notes, 2017, 10:60.
2. Hiermann A, Juan H, Sametz W. Influence of Epilobium extracts on prostaglandin biosynthesis and carrageenin induced oedema of the rat paw. Journal of Ethnopharmacology,1986, Aug; 17 (2):161-9.
3. Juan H, Sametz W, Hiermann A. Anti-inflammatory effects of a substance extracted from Epilobium angustifolium. Agents and Actions, 1988, 23: 106-107.
4. Vitali F, Fonte G, Saija A, Tita B. Inhibition of intestinal motility and secretion by extracts of Epilobium spp. in mice. Journal of Ethnopharmacology, 2006, Oct., 11; 107 (3):342-8.
5. Tita B, Abdel-Haq H, Vitalone A, Mazzanti G, Saso L. Analgesic properties of Epilobium angustifolium, evaluated by the hot plate test and the writhing test., Farmaco, 2001, May-Jul; 56(5-7):341-3.
6. Hiermann A, Reidlinger M, Juan H, Sametz W. Isolation of the antiphlogistic principle from Epilobium angustifolium. Planta Med., 1991, Aug; 57(4): 357-60.
7. Hiermann A, Schramm H.W, Laufer S. Anti-inflammatory activity of myricetin-3-O-beta-D-glucronide and related compounds. Inflamm. Res., 1998, 47, 421-427.
8. Stolarczyk M, Naruszewicz M, Kiss A.K. Extracts from Epilobium sp. Herbs induce apoptosis in human hormone-dependent prostate cancer cells by activating the mitochondrial pathway. Extracts from Epilobium sp. Herbs induce apoptosis in human hormone-dependent prostate cancer cells by activating the mitochondrial pathway. J .Pharm Pharmacol, 2013, Jul; 65(7):1044-54.
9. Ducrey B, Marston A, Gohring S, Hartmann R.W, Hostettmann K. Inhibition of 5alpha-reductaseandaromatasebytheellagitanninsoenothein A andoenotheinBfrom Epilobium species. PlantaMedica, 1997, 63,111–114.
10. Kiss A, Kowalski J, Melziq M.F. Phytomedicine, 2006, Induction of neutral endopeptidase activity in PC-3 cells by an aqueous extract of Epilobium angustifolium L. and oenothein B., Mar; 13(4):284-9.
11. Vitalone A, McColl J, Thome D, Costa L.G, Tita B. Characterization of the effect of Epilobium extracts on human cell proliferation. Pharmacology,2003, Oct; 69(2):79-87.
12. Committtee on Herbal Medicinal Products, 10 March 2015 EMA/HMPC/712510/2014, Assessment report on Epilobium angustifolium L. and /or Epilobium parviflorum Schreb. herba. Based on Article 16d(1), Article 16f and Article 16h of Directive 2001/83/EC as amended (traditional use). 13. Oenothein medicaments. Patent publish: US6528490 B2 14. Sakagami H, Jiang Y, Kusama K, Atsumi T, Ueha T, Toguchi M, Iwakura I, Satoh K, Ito H, Hatano T, Yoshida T. Cytotoxic activity of hydolyzable tannins against human oral tumor cell lines—a possible mechanism. Phytomedicine, 2000, Mar; 7(1):39-47. 15. Miyamoto K, Nomura M, Sasakura M, Matsui E, Koshiura R, Murayama T, Furukawa T, Hatano T, Yoshida T, Okuda T. Antitumor activity of oenothein B, a unique macrocycic ellagitannin. Jpn J. Cancer Res., 1993, Jan; 84(1):99-103.
16. Miyamoto Nomura K. M, Murayama T, Furukawa T, Hatano T, Yoshida T, Koshiura R, Okuda T. Antitumor activities of ellagitannins against sarcoma-180 in mice. Biol. Pharm. Bull, 1993, Apr; 16(4):379-87.
17. Rauha J. P, Remes S, Heinonen Hopia M, Kahkönen A, Kujala M, Pihlaja T, Vuorela K, Vuorela H. P. Antimicrobial effects of finnish plant extracts containing flavonoids and other phenolic compounds., Int. J. Food Micobiol., 2000, May 25;56(1):3-12.
18. Battinelli L, Tita B, Evandri M.G, Mazzanti G. Antimicrobial activity of Epilobium spp extracts. Farmaco,2001, May-Jul;56(5-7):345-8.
19. Kosalec I, Kopjar N, Kremer D. Antimicrobial activity of Willowherb (Epilobium angustifolium L.) leaves and flowers. Curr Drug Targets, 2013, Aug;14(9):986-91.
20. Webster D, Taschereau P, Belland R.J, Sand C, Rennie R.P. Antifungal activity of medicinal plant extracts; preliminary screening studies. Journal of Ethnopharmacology, 2008, Jan 4; 115(1):140-6.
21. Kahkönen M.P, Hopia A.I, Vuorela H.J, Rauha J.P, Pihlaja K, Kujala T.S, Heinonen M. Antioxidant activity of plant extracts containing phenolic compounds. J. Agric. Food Chem., 1999, Oct; 47(10):3954-62.
22. Stajner D, Popovi B.M, Bo_a P. Evaluation of willow herb’s (Epilobium angustifolium L.) antioxidant and radical scavenging capacities.Phytother Res., 2007, Jul 27.
23. Kiss A.K, Bazylko A, Filipek A, Granica S, Jaszewska E, Kiarszys U, Kosmider A, Piwowarski J. Oenothein B’s contribution to the anti-inflammatory and antioxidant activity of Epilobium sp. Phytomedicine, 2011, Volume 18, Issue 7, Pages 557-560.
24. Schepetkin I.A, Kirpotina L.N, Jakiw L, Khlebnikov A.I, Blashkovich C.L, Jutila M.A, Quinn M.T. Immunomodulatory Activity of Oenothein B Isolated from Epilobium angustifolium. 2009, The Journal of Immunology, Nov 15;183(10):6754-66.
25. Myagmar B.E, Aniya Y. Free radical scavenging action of medicinal herbs from Mongolia. Phytomedicine, 2000, Volume 7, Issue 3, Pages 221-229.
26. Miyamoto K, Murayama T, Nomura M, Hatano T, Yoshida T, Furukawa T, Koshiura R, Okuda T. Antitumor activity and interleukin-1 induction by tannins. Anticancer Res., 1993, Jan-Feb;13(1):37-42.
27. http://montana.plant-life.org/species/epilob_angus.html (accessed 10.08.2015)
28. Dzwonko Z, Loster S, Gawronski S. Impact of fire severity on soil properties and the development of tree and shrub species in a Scots pine moist forest site in southern Poland. Foretst Ecology and Management, 2015, Volume 342, 15 April, Pages 56–63.
29. Gurova K.New hopes from old drugs: revisiting DNA-binding small molecules as anticancer agents. Future Oncol. 2009, 5(10), 1685.
30. Cancer Fact Sheet No:297 World Health Organization. February 2014. Retrieved 10 June 2014.
31. National Cancer Institute, Defining Cancer. Retrieved 10 June 2014.
32. Braca A, Tommasi N.D, Bari L.D, Pizza C, Politi M, Morelli I. Antioxidantprinciples from Bauhinia terapotensis. , J. Nat. Prod., 2001, 64, 892–895.
33. Siddhuraju P, Becker K. Antioxidant properties of various solvent extracts of total phenolic constituents from three different agroclimatic regions of Drum- stick tree (Moringa olifera Lam.) leaves. 2003, J. Agric. Food Chem.,51 (), pp. 2144–2155.
34. Dinis T.C.P, Madeira V.M.C, Almeida L.M. Action of phenolic derivatives (acetoaminophen, salycilate and 5-aminosalycilate) as inhibitors of membrane lipid peroxidation and as peroxyl radical scavengers. Arch. Biochem. Biophys., 1994, 315, pp. 161–169.
35. Hertog M.G.L, Hollman P.C.H, Venema D.P. Optimization of a quantitative HPLC determination of potentially anticarcinogenic flavonoids in vegetables and fruits. J. Agric. Food Chem., 1992, 40, 1591.
36. Hossain Z, Huq F. Studies on the interaction between Ag+ and DNA. Journal of Inorganic Biochemistry, 2002, 91, 398-404.
37. Cutter C. Antimicrobial effect of herb extracts against Escherichia coli 0157:h7, Listeria monocytogenes and Salmonella typhimurium associated with beef. Food Prot. 2000, 63:601-607.
38. Hao Y.Y, Brackett R.E, Doyle M.P. Efficacy of plant extracts in inhibiting Aeromonas hydrophilia and Listeria monocytogenes in refrigerated cooked poultry. Food Microbiol. 1998, 15:367-378.
39. Puupponen Pimia R, Nohynek L., Meiier C, Kahkonen M, Heinonen M, Hopia A, Oksman Caldentey K.M. Antimicrobial properties of phenolic compounds from berries. J. Appl. Microbiol. 2001, 90:494-507.
40. American Journal of Pathology, news release, Nov. 27, 2012.
41. Yu X, Zhao M, Liu F, Zeng S, Hu J. Identification of 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one as a strong antioxidant in glucose–histidine Maillard reaction products. Food Research International, 2013, Volume 51, Issue 1, Pages 397-403.
42. Who. int /Concise International Chemical Assessment Document 21/2-Furaldehyde, 2000.
43. Petrovic´ V, Car Zˇ, Prugovecˇki B. S, Tomic D, Matkovic´ C. Synthesis of Acylated Methyl 2-Acetamido-2-Deoxy-a-D-Mannopyranosides Journal of Carbohydrate Chemistry, 2006, 25:685–695.
44. Mahadevan A, Hopper W. Degradation of catechin by Bradyrhizobium japonicum Biodegradation 1997, 8 (3): 159–165.
45. Api A.M. Toxicological profile of diethyl phthalate: a vehicle for fragrance and cosmetic ingredients. Food and Chemical Toxicology, 2001, 39 (2): 97–108.
46. Wilt T, Ishani A, MacDonald R, Stark G, Mulrow C, Lau J. Beta-sitosterols for benign prostatic hyperplasia. The Cochrane Library 2000, (2): CD001043.
47. Kim T. H, Lim H. J, Kim M. S, Lee M. S. Dietary supplements for benign prostatic hyperplasia: An overview of systematic reviews. Maturitas 2012, 73 (3): 180–5.
48. Sundararaman P, Djerassi C. A convenient synthesis of progesterone from stigmasterol. J Org Chem. 1977, 42 (22): 3633–3634.
49. Rudkowska I, AbuMweis S.S, Nicolle C, Jones P. J. Cholesterol-lowering efficacy of plant sterols in low-fat yogurt consumed as a snack or with a meal. J Am Coll Nutr 2008, . 27 (5): 588–95.
50. "Ellagic acid". American Cancer Society. November 2008. Retrieved August 2014.
51. U.S. Food and Drug Administration, 187 Fake Cancer 'Cures' Consumers Should Avoid, Accessed June 17, 2008.
52. Shivappurkar M, Galati and Stoner. Inhibition of N-nitrosobenzylmethylamine anda DNA-binding in cultured rat esophagus by ellagic acid. Carcinogenesis , 1988, 9 (7): 1313–1316.
53. Mandal and Stoner, Stoner G.D. Inhibition of N-nitrosobenzymethylamine-induced esophageal tumorigenesis in rats by ellagic acid.Carcinogenesis, 1990, 11 (1): 55–61.
54. Granica S, Piwoworski J.P, Czerwinska M.E, Kiss A. K. Phytochemistry, pharmacologyandtraditionalusesofdifferent Epilobium species (Onagraceae):Areview. Journal of Ethnopharmacology, 2014, 156, 316-346.
55. Noll D. M, Mason T. M, Miller P. S. Formation and Repair of Interstrand Cross-Links in DNA. Chem Rev. 2006, 106(2): 277-301.
56.www.cancer.org(http://www.cancer.org/treatment/treatmentsandsideeffects/treatmenttypes/chemotherapy/chemotherapyprinciplesanin-depthdiscussionofthetechniquesanditsroleintreatment/chemotherapy-principles-types-of-chemo-drugs ( accessed 18.09.2015).
57. Saeed N, Khan M.R, Shabbir M. Antioxidant activity, Total phenolic and Total Flavonoid Contents of Whole Plant Extracts Torilis lepthophylla.BMC Complementary & Alternative Medicine, 2012, 12:221.
58. Grattan Bruce Jr J. Nutrients, Plant Sterols as Anticancer Nutrients: Evidence for Their Role in Breast Cancer. 2013, Feb; 5(2): 359–387.
59. Martins P, Jesus J, Santos S, Raposo L. R, Roma-Rodrigues C, Baptista P. V. Heterocyclic anticancer compounds: Recent advances and the paradigm shift towards the use of nanomedicine’s tool box. Fernandes,A. R. , 2015, Molecules, 2015, 20, 16852-16891; doi:10.3390/molecules200916852.
60. Kosalec I, Zovko M, Sankovic K, Kremer D, Pepeljnjak S. Antioxidant and antimicrobial activity of willow herb (Epilobium angustifolium L.)Planta Med. 2008: 74 PA43 DOI: 10.1055/s-0028-1084041.
61. Rasoanaivo P, Wright C. W, Willcox M.L, Gilbert B. Whole plant extracts versus single compounds fort he treatment of malaria: Synergy and positive interactions. Malaria Journal, 2011, 10(suppl 1):54.

There are 58 citations in total.

Details

Primary Language	English
Subjects	Engineering, Chemical Engineering
Journal Section	Articles
Authors	Aysema Sayık This is me Ayşe Sergüzel Yusufoğlu Leyla Açık Gülen Türker Betül Aydın Leyla Arslan This is me
Publication Date	August 3, 2017
Submission Date	June 7, 2017
Acceptance Date	August 2, 2017
Published in Issue	Year 2017 Volume: 4 Issue: 3

Cite

Vancouver	Sayık A, Yusufoğlu AS, Açık L, Türker G, Aydın B, Arslan L. DNA- Binding, Biological Activities, and Chemical Composition of Wild Growing Epilobium angustifolium L. Extracts from Canakkale, Turkey. JOTCSA. 2017;4(3):811-40.