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Elucidation of biological properties of some commercial anthraquinones: Mutagenic / antimutagenic and antimicrobial activity approaches

Yıl 2019, Cilt: 23 Sayı: 2, 208 - 216, 27.06.2025

Ahmet Uysal , Erdoğan Güneş , Yusuf Durak

Öz

Anthraquinones (AQ) are the most common group of naturally occurring quinones. Both natural and synthetic AQs have been used as colorants in food, drugs and cosmetic industries. The aim of this study was to evaluate the mutagenic/antimutagenic potentials of some AQs (Alizarin, quinizarin, purpurin, and 1,8-dihydroxy anthraquinone) with Salmonella typhimurium TA98 and TA100 strains by Ames test and antimicrobial activity by broth microdilution method. So, AQs were tested for their toxicity and nontoxic doses of the chemicals were used. The results manifested that none of the chemicals were mutagenic for TA98 and TA100 strains both with and without metabolic activation enzymes (S9 mix). Purpurin and alizarin exhibited strong antimutagenic effects against 4- nitrophenylendiameine and 2-aminoflourene at all test doses (1000, 500 and 250 µg/plate) for TA98; and against sodium azide and 2-aminoanthracene for TA100. Alizarin showed the highest inhibition rate (93%) against sodium azide at a concentration of 1000 µg/plate. While 1,8-dihydroxy anthraquinone and quinizarin revealed strong antimutagenicity at 10000 µg/plate without S9 mix, they exhibited excellent antimutagenic action after addition of S9 enzymes for TA98 strain at all test doses. Similarly, 1,8-dihydroxy anthraquinone and quinizarin were moderate antimutagenic against sodium azide at all test doses without S9 mix, their antimutagenicity increased and they ameliorated the mutagenic action of 2-aminoanthracene by the addition of S9 for TA100. These two chemicals were strong antimutagenic against promutagens activated by S9 mix. Also it was defined that purpurin and alizarin have antimicrobial capacity against MRSA strains.

Anahtar Kelimeler

Alizarin quinizarin purpurin 1 8-dihydroxy anthraquinone Ames test antimicrobial

Kaynakça

  • [1] Fiehn O. Metabolomics - the link between genotypes and phenotypes. Plant Mol Biol. 2002;48(1-2):155-171. [CrossRef]
  • [2] Hamilton AC. Medicinal plants, conservation and livelihoods. Biodivers Conserv. 2004;13(8):1477-1517. [CrossRef]
  • [3] Hattenschwiler S, Vitousek PM. The role of polyphenols in terrestrial ecosystem nutrient cycling. Trends Ecol Evol. 2000;15(6):238-243. [CrossRef]
  • [4] Kutchan TM. Ecological arsenal and developmental dispatcher. The paradigm of secondary metabolism. Plant Physiol. 2001;125(1):58-60. [CrossRef]
  • [5] Lattanzio V, Kroon PA, Quideau S, Treutter D. Plant phenolics - Secondary metabolites with diverse functions. Rec Adv Polyphen Res. 2008;1:1-35.
  • [6] Lattanzio V. Phenolic Compounds: Introduction. In: Ramawat K, Mérillon JM. (Eds). Natural Products. Springer, Berlin, Heidelberg 2013, pp. 1543-1580.
  • [7] Carocho M, Ferreira ICFR. A review on antioxidants, prooxidants and related controversy: Natural and synthetic compounds, screening and analysis methodologies and future perspectives. Food Chem Toxicol. 2013;51:15-25. [CrossRef]
  • [8] Birosova L, Mikulasova M, Vaverkova S. Antimutagenic effect of phenolic acids. Biomed Pap Med Fac Univ Palacky Olomouc Czech Repub. 2005;149(2):489-491.
  • [9] Orhan I, Kartal M, Tosun F, Sener B. Screening of various phenolic acids and flavonoid derivatives for their anticholinesterase potential. Z Naturforsch C. 2007;62(11-12):829-832.
  • [10] Zengin G, Locatelli M, Ceylan R, Aktumsek A. Anthraquinone profile, antioxidant and enzyme inhibitory effect of root extracts of eight Asphodeline taxa from Turkey: can Asphodeline roots be considered as a new source of natural compounds? J Enzyme Inhib Med Chem. 2016;31(5):754-759. [CrossRef]
  • [11] Monks TJ, Hanzlik RP, Cohen GM, Ross D, Graham DG. Quinone chemistry and toxicity. Toxicol Appl Pharm. 1992;112(1):2-16. [CrossRef]
  • [12] Malik EM, Muller CE. Anthraquinones as pharmacological tools and drugs. Med Res Rev. 2016;36(4):705-748. [CrossRef]
  • [13] Van Gorkom BAP, De Vries EGE, Karrenbeld A, Kleibeuker JH. Review article: anthranoid laxatives and their potential carcinogenic effects. Aliment Pharm Therap. 1999;13(4):443-452.
  • [14] Shrestha JP, Subedi YP, Chen LH, Chang CWT. A mode of action study of cationic anthraquinone analogs: a new class of highly potent anticancer agents. MedChemComm. 2015;6(11):2012-2022. [CrossRef]
  • [15] Khan K, Karodi R, Siddiqui A, Thube S, Rub R. Development of anti-acne gel formulation of anthraquinones rich fraction from Rubia cordifolia (Rubiaceae). Int J Appl Res in Nat Prod. 2012;4(4):28-36.
  • [16] Davis RH, Agnew PS, Shapiro E. Antiarthritic activity of anthraquinones found in Aloe for podiatric medicine. J Am Podiat Med Assn. 1986;76(2):61-66. [CrossRef]
  • [17] Wuthiudomlert M, Kupittayanant P, Gritsanapan W. In vitro evaluation of antifungal activity of anthraquinone derivatives of Senna alata. J Health Res. 2010;24(3):117-122.
  • [18] Fosso MY, Chan KY, Gregory R, Chang CWT. Library synthesis and antibacterial investigation of cationic anthraquinone analogs. Acs Comb Sci. 2012;14(3):231-235. [CrossRef]
  • [19] Barnard DL, Fairbairn DW, ONeill KL, Gage TL, Sidwell RW. Anti-human cytomegalovirus activity and toxicity of sulfonated anthraquinones and anthraquinone derivatives. Antivir Res. 1995;28(4):317-329. [CrossRef]
  • [20] Seo EJ, Ngoc TM, Lee SM, Kim YS, Jung YS. Chrysophanol-8-O-glucoside, an anthraquinone derivative in Rhubarb, has antiplatelet and anticoagulant activities. J Pharmacol Sci. 2012;118(2):245-254. [CrossRef]
  • [21] Jackson TC, Verrier JD, Kochanek PM. Anthraquinone-2-sulfonic acid (AQ2S) is a novel neurotherapeutic agent. Cell Death Dis. 2013;4:1-12. [CrossRef]
  • [22] Winter RW, Cornell KA, Johnson LL, Ignatushchenko M, Hinrichs DJ, Riscoe MR. Potentiation of the antimalarial agent rufigallol. Antimicrob Agents Chemother. 1996;40(6):1408-1411.
  • [23] Chesis PL, Levin DE, Smith MT, Ernster L, Ames BN. Mutagenicity of quinones - Pathways of metabolic-activation and detoxification. P Natl Acad Sci-Biol. 1984;81(6):1696-1700. [CrossRef]
  • [24] Sendelbach LE. A review of the toxicity and carcinogenicity of anthraquinone derivatives. Toxicology. 1989;57(3):227-240. [CrossRef]
  • [25] Brown JP. A review of the genetic effects of naturally occurring flavonoids, anthraquinones and related compounds. Mutat Res. 1980;75(3):243-277.
  • [26] Muller SO, Eckert I, Lutz WK, Stopper H. Genotoxicity of the laxative drug components emodin, aloe-emodin and danthron in mammalian cells: Topoisomerase II mediated? Mutat Res. 1996;371(3-4):165-173.
  • [27] Mueller SO, Stopper H, Dekant W. Biotransformation of the anthraquinones emodin and chrysophanol by cytochrome P450 enzymes - Bioactivation to genotoxic metabolites. Drug Metab Dispos. 1998;26(6):540-546.
  • [28] Venturini S, Tamaro M. Mutagenicity of anthraquinone and azo dyes in Ames' Salmonella typhimurium test. Mutat Res. 1979;68(4):307-312.
  • [29] Leme DM, de Oliveira GAR, Meireles G, dos Santos TC, Zanoni MVB, de Oliveira DP. Genotoxicological assessment of two reactive dyes extracted from cotton fibres using artificial sweat. Toxicol in Vitro. 2014;28(1):31-38. [CrossRef]
  • [30] Brown JP, Brown RJ. Mutagenesis by 9,10-anthraquinone derivatives and related compounds in Salmonella typhimurium. Mutat Res. 1976;40(3):203-224.
  • [31] Laham S, Grice H, Sinclair J. Studies in chemical carcinogenesis, III. Alpha-aminoanthraquinone. Toxicol Appl Pharmacol. 1966.
  • [32] Hsu S-C, Chung J-G. Anticancer potential of emodin. Biomedicine. 2012;2(3):108-116.
  • [33] Jelassi B, Anchelin M, Chamouton J, et al. Anthraquinone emodin inhibits human cancer cell invasiveness by antagonizing P2X7 receptors. Carcinogenesis. 2013;34(7):1487-1496. [CrossRef]
  • [34] Lin SZ, Wei WT, Chen H, et al. Antitumor activity of emodin against pancreatic cancer depends on its dual role: Promotion of apoptosis and suppression of angiogenesis. Plos One. 2012;7(8). [CrossRef]
  • [35] Chiu TH, Lai WW, Hsia TC, et al. Aloe-emodin induces cell death through s-phase arrest and caspase-dependent pathways in human tongue squamous cancer SCC4 cells. Anticancer Res. 2009;29(11):4503-4511.
  • [36] Guo JM, Xiao BX, Liu Q, et al. Anticancer effect of aloe-emodin on cervical cancer cells involves G2/M arrest and induction of differentiation. Acta Pharmacol Sin. 2007;28(12):1991-1995. [CrossRef]
  • [37] Kuo PL, Lin TC, Lin CC. The antiproliferative activity of aloe-emodin is through p53-dependent and p21-dependent apoptotic pathway in human hepatoma cell lines. Life Sci. 2002;71(16):1879-1892. [CrossRef]
  • [38] Pecere T, Gazzola MV, Mucignat C, et al. Aloe-emodin is a new type of anticancer agent with selective activity against neuroectodermal tumors. Cancer Res. 2000;60(11):57-77. [CrossRef]
  • [39] Edenharder Rv, Von Petersdorff I, Rauscher R. Antimutagenic effects of flavoniods, chalcones and structurally related compounds on the activity of 2-amino-3-methylinidazo [4, 5-ƒ] quinoline (IQ) and other heterocyclic amine mutagens from cooked food. Mutat Res Fund Mol Mech Mut. 1993;287(2):261-274.
  • [40] Takahashi E, Fujita K, Kamataki T, et al. Inhibition of human cytochrome P450 1B1, 1A1 and 1A2 by antigenotoxic compounds, purpurin and alizarin. Mutat Res. 2002;508(1-2):147-156.
  • [41] Charehsaz M, Sipahi H, Giri AK, Aydin A. Antimutagenic and anticlastogenic effects of Turkish Black Tea on TA98 and TA100 strains of Salmonella typhimurium (in vitro) and mice (in vivo). Pharm Biol. 2017;55(1):1202-1206. [CrossRef]
  • [42] Mocan A, Zengin G, Mollica A, et al. Biological effects and chemical characterization of Iris schachtii Markgr. extracts: A new source of bioactive constituents. Food Chem Toxicol. 2018;112:448-457. [CrossRef]
  • [43] Dean BJ, Brooks TM, Hodsonwalker G, Hutson DH. Genetic toxicology testing of 41 industrial-chemicals. Mutat Res. 1985;153(1-2):57-77.
  • [44] Maron DM, Ames BN. Revised methods for the Salmonella mutagenicity test. Mutat Res. 1983;113(3-4):173-215.
  • [45] Mortelmans K, Zeiger E. The Ames Salmonella/microsome mutagenicity assay. Mutat Res-Fund Mol Mech Mut. 2000;455(1-2):29-60.
  • [46] Zengin G, Uysal A, Gunes E, Aktumsek A. Survey of phytochemical composition and biological effects of three extracts from a wild plant (Cotoneaster nummularia Fisch et Mey.): A potential source for functional food ingredients and drug formulations. Plos One. 2014;9(11). [CrossRef]
  • [47] Negi PS, Jayaprakasha GK, Jena BS. Antioxidant and antimutagenic activities of pomegranate peel extracts. Food Chem. 2003;80(3):393-397.

Yıl 2019, Cilt: 23 Sayı: 2, 208 - 216, 27.06.2025

Ahmet Uysal , Erdoğan Güneş , Yusuf Durak

Öz

Kaynakça

  • [1] Fiehn O. Metabolomics - the link between genotypes and phenotypes. Plant Mol Biol. 2002;48(1-2):155-171. [CrossRef]
  • [2] Hamilton AC. Medicinal plants, conservation and livelihoods. Biodivers Conserv. 2004;13(8):1477-1517. [CrossRef]
  • [3] Hattenschwiler S, Vitousek PM. The role of polyphenols in terrestrial ecosystem nutrient cycling. Trends Ecol Evol. 2000;15(6):238-243. [CrossRef]
  • [4] Kutchan TM. Ecological arsenal and developmental dispatcher. The paradigm of secondary metabolism. Plant Physiol. 2001;125(1):58-60. [CrossRef]
  • [5] Lattanzio V, Kroon PA, Quideau S, Treutter D. Plant phenolics - Secondary metabolites with diverse functions. Rec Adv Polyphen Res. 2008;1:1-35.
  • [6] Lattanzio V. Phenolic Compounds: Introduction. In: Ramawat K, Mérillon JM. (Eds). Natural Products. Springer, Berlin, Heidelberg 2013, pp. 1543-1580.
  • [7] Carocho M, Ferreira ICFR. A review on antioxidants, prooxidants and related controversy: Natural and synthetic compounds, screening and analysis methodologies and future perspectives. Food Chem Toxicol. 2013;51:15-25. [CrossRef]
  • [8] Birosova L, Mikulasova M, Vaverkova S. Antimutagenic effect of phenolic acids. Biomed Pap Med Fac Univ Palacky Olomouc Czech Repub. 2005;149(2):489-491.
  • [9] Orhan I, Kartal M, Tosun F, Sener B. Screening of various phenolic acids and flavonoid derivatives for their anticholinesterase potential. Z Naturforsch C. 2007;62(11-12):829-832.
  • [10] Zengin G, Locatelli M, Ceylan R, Aktumsek A. Anthraquinone profile, antioxidant and enzyme inhibitory effect of root extracts of eight Asphodeline taxa from Turkey: can Asphodeline roots be considered as a new source of natural compounds? J Enzyme Inhib Med Chem. 2016;31(5):754-759. [CrossRef]
  • [11] Monks TJ, Hanzlik RP, Cohen GM, Ross D, Graham DG. Quinone chemistry and toxicity. Toxicol Appl Pharm. 1992;112(1):2-16. [CrossRef]
  • [12] Malik EM, Muller CE. Anthraquinones as pharmacological tools and drugs. Med Res Rev. 2016;36(4):705-748. [CrossRef]
  • [13] Van Gorkom BAP, De Vries EGE, Karrenbeld A, Kleibeuker JH. Review article: anthranoid laxatives and their potential carcinogenic effects. Aliment Pharm Therap. 1999;13(4):443-452.
  • [14] Shrestha JP, Subedi YP, Chen LH, Chang CWT. A mode of action study of cationic anthraquinone analogs: a new class of highly potent anticancer agents. MedChemComm. 2015;6(11):2012-2022. [CrossRef]
  • [15] Khan K, Karodi R, Siddiqui A, Thube S, Rub R. Development of anti-acne gel formulation of anthraquinones rich fraction from Rubia cordifolia (Rubiaceae). Int J Appl Res in Nat Prod. 2012;4(4):28-36.
  • [16] Davis RH, Agnew PS, Shapiro E. Antiarthritic activity of anthraquinones found in Aloe for podiatric medicine. J Am Podiat Med Assn. 1986;76(2):61-66. [CrossRef]
  • [17] Wuthiudomlert M, Kupittayanant P, Gritsanapan W. In vitro evaluation of antifungal activity of anthraquinone derivatives of Senna alata. J Health Res. 2010;24(3):117-122.
  • [18] Fosso MY, Chan KY, Gregory R, Chang CWT. Library synthesis and antibacterial investigation of cationic anthraquinone analogs. Acs Comb Sci. 2012;14(3):231-235. [CrossRef]
  • [19] Barnard DL, Fairbairn DW, ONeill KL, Gage TL, Sidwell RW. Anti-human cytomegalovirus activity and toxicity of sulfonated anthraquinones and anthraquinone derivatives. Antivir Res. 1995;28(4):317-329. [CrossRef]
  • [20] Seo EJ, Ngoc TM, Lee SM, Kim YS, Jung YS. Chrysophanol-8-O-glucoside, an anthraquinone derivative in Rhubarb, has antiplatelet and anticoagulant activities. J Pharmacol Sci. 2012;118(2):245-254. [CrossRef]
  • [21] Jackson TC, Verrier JD, Kochanek PM. Anthraquinone-2-sulfonic acid (AQ2S) is a novel neurotherapeutic agent. Cell Death Dis. 2013;4:1-12. [CrossRef]
  • [22] Winter RW, Cornell KA, Johnson LL, Ignatushchenko M, Hinrichs DJ, Riscoe MR. Potentiation of the antimalarial agent rufigallol. Antimicrob Agents Chemother. 1996;40(6):1408-1411.
  • [23] Chesis PL, Levin DE, Smith MT, Ernster L, Ames BN. Mutagenicity of quinones - Pathways of metabolic-activation and detoxification. P Natl Acad Sci-Biol. 1984;81(6):1696-1700. [CrossRef]
  • [24] Sendelbach LE. A review of the toxicity and carcinogenicity of anthraquinone derivatives. Toxicology. 1989;57(3):227-240. [CrossRef]
  • [25] Brown JP. A review of the genetic effects of naturally occurring flavonoids, anthraquinones and related compounds. Mutat Res. 1980;75(3):243-277.
  • [26] Muller SO, Eckert I, Lutz WK, Stopper H. Genotoxicity of the laxative drug components emodin, aloe-emodin and danthron in mammalian cells: Topoisomerase II mediated? Mutat Res. 1996;371(3-4):165-173.
  • [27] Mueller SO, Stopper H, Dekant W. Biotransformation of the anthraquinones emodin and chrysophanol by cytochrome P450 enzymes - Bioactivation to genotoxic metabolites. Drug Metab Dispos. 1998;26(6):540-546.
  • [28] Venturini S, Tamaro M. Mutagenicity of anthraquinone and azo dyes in Ames' Salmonella typhimurium test. Mutat Res. 1979;68(4):307-312.
  • [29] Leme DM, de Oliveira GAR, Meireles G, dos Santos TC, Zanoni MVB, de Oliveira DP. Genotoxicological assessment of two reactive dyes extracted from cotton fibres using artificial sweat. Toxicol in Vitro. 2014;28(1):31-38. [CrossRef]
  • [30] Brown JP, Brown RJ. Mutagenesis by 9,10-anthraquinone derivatives and related compounds in Salmonella typhimurium. Mutat Res. 1976;40(3):203-224.
  • [31] Laham S, Grice H, Sinclair J. Studies in chemical carcinogenesis, III. Alpha-aminoanthraquinone. Toxicol Appl Pharmacol. 1966.
  • [32] Hsu S-C, Chung J-G. Anticancer potential of emodin. Biomedicine. 2012;2(3):108-116.
  • [33] Jelassi B, Anchelin M, Chamouton J, et al. Anthraquinone emodin inhibits human cancer cell invasiveness by antagonizing P2X7 receptors. Carcinogenesis. 2013;34(7):1487-1496. [CrossRef]
  • [34] Lin SZ, Wei WT, Chen H, et al. Antitumor activity of emodin against pancreatic cancer depends on its dual role: Promotion of apoptosis and suppression of angiogenesis. Plos One. 2012;7(8). [CrossRef]
  • [35] Chiu TH, Lai WW, Hsia TC, et al. Aloe-emodin induces cell death through s-phase arrest and caspase-dependent pathways in human tongue squamous cancer SCC4 cells. Anticancer Res. 2009;29(11):4503-4511.
  • [36] Guo JM, Xiao BX, Liu Q, et al. Anticancer effect of aloe-emodin on cervical cancer cells involves G2/M arrest and induction of differentiation. Acta Pharmacol Sin. 2007;28(12):1991-1995. [CrossRef]
  • [37] Kuo PL, Lin TC, Lin CC. The antiproliferative activity of aloe-emodin is through p53-dependent and p21-dependent apoptotic pathway in human hepatoma cell lines. Life Sci. 2002;71(16):1879-1892. [CrossRef]
  • [38] Pecere T, Gazzola MV, Mucignat C, et al. Aloe-emodin is a new type of anticancer agent with selective activity against neuroectodermal tumors. Cancer Res. 2000;60(11):57-77. [CrossRef]
  • [39] Edenharder Rv, Von Petersdorff I, Rauscher R. Antimutagenic effects of flavoniods, chalcones and structurally related compounds on the activity of 2-amino-3-methylinidazo [4, 5-ƒ] quinoline (IQ) and other heterocyclic amine mutagens from cooked food. Mutat Res Fund Mol Mech Mut. 1993;287(2):261-274.
  • [40] Takahashi E, Fujita K, Kamataki T, et al. Inhibition of human cytochrome P450 1B1, 1A1 and 1A2 by antigenotoxic compounds, purpurin and alizarin. Mutat Res. 2002;508(1-2):147-156.
  • [41] Charehsaz M, Sipahi H, Giri AK, Aydin A. Antimutagenic and anticlastogenic effects of Turkish Black Tea on TA98 and TA100 strains of Salmonella typhimurium (in vitro) and mice (in vivo). Pharm Biol. 2017;55(1):1202-1206. [CrossRef]
  • [42] Mocan A, Zengin G, Mollica A, et al. Biological effects and chemical characterization of Iris schachtii Markgr. extracts: A new source of bioactive constituents. Food Chem Toxicol. 2018;112:448-457. [CrossRef]
  • [43] Dean BJ, Brooks TM, Hodsonwalker G, Hutson DH. Genetic toxicology testing of 41 industrial-chemicals. Mutat Res. 1985;153(1-2):57-77.
  • [44] Maron DM, Ames BN. Revised methods for the Salmonella mutagenicity test. Mutat Res. 1983;113(3-4):173-215.
  • [45] Mortelmans K, Zeiger E. The Ames Salmonella/microsome mutagenicity assay. Mutat Res-Fund Mol Mech Mut. 2000;455(1-2):29-60.
  • [46] Zengin G, Uysal A, Gunes E, Aktumsek A. Survey of phytochemical composition and biological effects of three extracts from a wild plant (Cotoneaster nummularia Fisch et Mey.): A potential source for functional food ingredients and drug formulations. Plos One. 2014;9(11). [CrossRef]
  • [47] Negi PS, Jayaprakasha GK, Jena BS. Antioxidant and antimutagenic activities of pomegranate peel extracts. Food Chem. 2003;80(3):393-397.
Toplam 47 adet kaynakça vardır.

Ayrıntılar

Birincil Dil İngilizce
Konular Farmasotik Mikrobiyoloji, Tıbbi Farmakoloji
Bölüm Articles
Yazarlar

Ahmet Uysal

Erdoğan Güneş

Yusuf Durak

Yayımlanma Tarihi 27 Haziran 2025
Yayımlandığı Sayı Yıl 2019 Cilt: 23 Sayı: 2

Kaynak Göster

APA Uysal, A., Güneş, E., & Durak, Y. (2025). Elucidation of biological properties of some commercial anthraquinones: Mutagenic / antimutagenic and antimicrobial activity approaches. Journal of Research in Pharmacy, 23(2), 208-216.
AMA Uysal A, Güneş E, Durak Y. Elucidation of biological properties of some commercial anthraquinones: Mutagenic / antimutagenic and antimicrobial activity approaches. J. Res. Pharm. Haziran 2025;23(2):208-216.
Chicago Uysal, Ahmet, Erdoğan Güneş, ve Yusuf Durak. “Elucidation of Biological Properties of Some Commercial Anthraquinones: Mutagenic / Antimutagenic and Antimicrobial Activity Approaches”. Journal of Research in Pharmacy 23, sy. 2 (Haziran 2025): 208-16.
EndNote Uysal A, Güneş E, Durak Y (01 Haziran 2025) Elucidation of biological properties of some commercial anthraquinones: Mutagenic / antimutagenic and antimicrobial activity approaches. Journal of Research in Pharmacy 23 2 208–216.
IEEE A. Uysal, E. Güneş, ve Y. Durak, “Elucidation of biological properties of some commercial anthraquinones: Mutagenic / antimutagenic and antimicrobial activity approaches”, J. Res. Pharm., c. 23, sy. 2, ss. 208–216, 2025.
ISNAD Uysal, Ahmet vd. “Elucidation of Biological Properties of Some Commercial Anthraquinones: Mutagenic / Antimutagenic and Antimicrobial Activity Approaches”. Journal of Research in Pharmacy 23/2 (Haziran 2025), 208-216.
JAMA Uysal A, Güneş E, Durak Y. Elucidation of biological properties of some commercial anthraquinones: Mutagenic / antimutagenic and antimicrobial activity approaches. J. Res. Pharm. 2025;23:208–216.
MLA Uysal, Ahmet vd. “Elucidation of Biological Properties of Some Commercial Anthraquinones: Mutagenic / Antimutagenic and Antimicrobial Activity Approaches”. Journal of Research in Pharmacy, c. 23, sy. 2, 2025, ss. 208-16.
Vancouver Uysal A, Güneş E, Durak Y. Elucidation of biological properties of some commercial anthraquinones: Mutagenic / antimutagenic and antimicrobial activity approaches. J. Res. Pharm. 2025;23(2):208-16.