Phytochemical Profiling and Evaluation of Marrubium sivasense Aytaç, Akgül & Ekici for Antioxidant Activity and Inhibition Effects on α-Amylase, Lipoxygenase, Xanthine Oxidase and Tyrosinase Enzymes
Year 2019,
Volume: 6 Issue: 3, 281 - 292, 20.10.2019
Fatih Göğer
,
Gülmira Özek
,
Mehmet Tekin
Süleyman Yur
Temel Özek
Abstract
Methanol extract of Marrubium. sivasense Aytaç, Akgül & Ekici was analyzed with LC-MS/MS technique. Forsythoside B, verbascoside and leucoseptoside were identified as main compounds. Antioxidant properties of the extract was determined by DPPH free radical scavenging activity (IC50 0.34 mg/mL), trolox equivalent antioxidant capacity (TEAC) (2.3 mM±0.04), xanthine-xanthine oxidase(XO) inhibitory effect (16.54 %). and. B-carotene bleaching (Inh. 43±1.26 %) assays. The extract demonstrated hypoglycemic activity (Inh. 49.67±1.09 %.) via inhibition of porcine pancreatic α-amylase, the antiinflammatory effect of the extract tested via inhibition of 5-LOX was found as Inh 18.71±0.74 %, however no antityrosinase activity was found.
Supporting Institution
Anadolu University Scientific Research Department
References
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- 14. Boudjelal A, Henchiri C, Siracusa L, Sari M, Ruberto G. Compositional Analysis And In Vivo Anti-Diabetic Activity Of Wild Algerian Marrubium vulgare L. Infusion. Fitoterapia. 2012;83(2):286-92.
- 15. Namjoyan F, Azemi ME, Abdollahi E, Goudarzi N, Nikan K. Angiotensin I Converting Enzyme Inhibitory Activities Of Hydroalcoholic Extract of Nardostachys jatamansi, Prangos ferulacea and Marrubium vulgare. Jundishapur J Nat Pharm Prod. 2015;10(2):e17255.
- 16. Ettaya A, Dhibi S, Samout N, Elfeki A, Hfaiedh N. Hepatoprotective Activity Of White Horehound (Marrubium Vulgare) Extract Against Cyclophosphamide Toxicity In Male Rats. Can J Physiol Pharmacol. 2015;94(4):441-7.
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- 25. Song H-P, Zhang H, Fu Y, Mo H-y, Zhang M, Chen J, et al. Screening for Selective Inhibitors Of Xanthine Oxidase From Flos Chrysanthemum Using Ultrafiltration LC–MS Combined With Enzyme Channel Blocking. J Chromatogr B. 2014;961:56-61.
- 26. Kaurinovic B, Vlaisavljevic S, Popovic M, Vastag D, Djurendic-Brenesel M. Antioxidant Properties Of Marrubium Peregrinum L.(Lamiaceae) Essential Oil. Molecules. 2010;15(9):5943-55.
- 27. Sahpaz S, Garbacki N, Tits M, Bailleul F. Isolation and Pharmacological Activity Of Phenylpropanoid Esters From Marrubium vulgare. J Ethnopharmacol. 2002;79(3):389-92.
- 28. Essawy SS, Abo-Elmatty DM, Ghazy NM, Badr JM, Sterner O. Antioxidant and Anti-Inflammatory Effects Of Marrubium Alysson Extracts In High Cholesterol-Fed Rabbits. Saudi Pharm J. 2014;22(5):472-82.
- 29. Benkhnigue O, Ben Akka F, Salhi S, Fadli M, Douira A, Zidane L. Catalogue Des Plantes Médicinales Utilisées Dans Le Traitement Du Diabète Dans La Région d’Al Haouz-Rhamna (Maroc). J Anim Plant Sci. 2014;23(1):3539-68.
- 30. Orch H, Douira A, Zidane L. Étude Ethnobotanique Des Plantes Médicinales Utilisées Dans Le Traitement Du Diabète, Et Des Maladies Cardiaques Dans La Région d’Izarène (Nord du Maroc). J Appl Biosci. 2015;86(1):7940-56.
- 31. Tsukamoto K, Jackson IJ, Urabe K, Montague PM, Hearing V. A Second Tyrosinase-Related Protein, TRP-2, Is A Melanogenic Enzyme Termed Dopachrome Tautomerase. EMBO J. 1992;11(2):519-26.
- 32. Xu Y, Stokes AH, Freeman WM, Kumer SC, Vogt BA, Vrana KE. Tyrosine mRNA is Expressed In Human Substantia Nigra. Mol Brain Res. 1997;45(1):159-62.
- 33. Namjoyan F, Jahangiri A, Azemi ME, Arkian E, Mousavi H. Inhibitory Effects of Physalis alkekengi L., Alcea rosea L., Bunium persicum B. Fedtsch. and Marrubium vulgare L. on Mushroom Tyrosinase. Jundishapur J Nat Pharm Prod. 2015;10(1):1-6.
- 34. Brand-Williams W, Cuvelier M-E, Berset C. Use Of A Free Radical Method To Evaluate Antioxidant Activity. LWT-Food Sci Technol. 1995;28(1):25-30.
- 35. Re R, Pellegrini N, Proteggente A, Pannala A, Yang M, Rice-Evans C. Antioxidant Activity Applying An Improved ABTS Radical Cation Decolorization Assay. Free Rad Biol Med. 1999;26(9-10):1231-7.
- 36. Prior RL, Wu X, Schaich K. Standardized Methods For The Determination Of Antioxidant Capacity And Phenolics In Foods And Dietary Supplements. J Agric Food Chem. 2005;53(10):4290-302.
- 37. Marco GJ. A Rapid Method For Evaluation Of Antioxidants. J Am Oil Chem Soc. 1968;45(9):594-8.
- 38. Chen C-H, Chan H-C, Chu Y-T, Ho H-Y, Chen P-Y, Lee T-H, et al. Antioxidant Activity Of Some Plant Extracts Towards Xanthine Oxidase, Lipoxygenase And Tyrosinase. Molecules. 2009;14(8):2947-58.
- 39. Masuda T, Yamashita D, Takeda Y, Yonemori S. Screening For Tyrosinase Inhibitors Among Extracts Of Seashore Plants And Identification Of Potent Inhibitors From Garcinia subelliptica. Biosci Biotech Biochem. 2005;69(1):197-201.
- 40. Yang X-W, Huang M-Z, Jin Y-S, Sun L-N, Song Y, Chen H-S. Phenolics from Bidens bipinnata And Their Amylase Inhibitory Properties. Fitoterapia. 2012;83(7):1169-75.
- 41. Albano SM, Lima AS, Pedro MGMLG, Barroso JG, Figueiredo AC. Antioxidant, Anti-5-Lipoxygenase And Antiacetylcholinesterase Activities Of Essential Oils And Decoction Waters Of Some Aromatic Plants. Rec Nat Prod. 2012;6(1):35.
- 42. Michelis F, Tiligada E, Skaltsa H, Lazari D, Skaltsounis A-L, Delitheos A. Effects of the Flavonoid Pilloin Isolated From Marrubium Cylleneum On Mitogen-Induced Lymphocyte Transformation. Pharm Biol. 2002;40(4):245-8.
- 43. Çalis I, Hosny M, Khalifa T, Rüedi P. Phenylpropanoid Glycosides From Marrubium alysson. Phytochem. 1992;31(10):3624-6.
- 44. Hussain A, Perveen S, Malik A, Afza N, Iqbal L, Tareen RB. Urease Inhibitiory Flavone Glucosides from Marrubium anisodon. Pol J Chem. 2009;83(7):1329-35.
- 45. Mitreski I, Stanoeva JP, Stefova M, Stefkov G, Kulevanova S. Polyphenols in Representative Teucrium Species in the Flora of R. Macedonia: LC/DAD/ESI-MS (n) profile and content. Nat Prod Commun. 2014;9(2):175-80.
- 46. Kırmızıbekmez H, Montoro P, Piacente S, Pizza C, Dönmez A, Çalış İ. Identification by HPLC‐PAD‐MS and Quantification by HPLC‐PAD of Phenylethanoid Glycosides of Five Phlomis Species. Phytochem Anal. 2005;16(1):1-6.
- 47. Ulubelen A, Topcu G, Kolak U. Labiatae flavonoids and their bioactivity. In: Atta ur R, editor. Studies in Natural Products Chemistry. Vol. 30: Elsevier; 2005. p. 233-302.
- 48. Buckingham J, Munasinghe VRN. Dictionary of Flavonoids with CD-ROM: CRC Press; 2015.
- 49. Tsvetkov D, Dmitrenok A, Tsvetkov YE, Menshov V, Yashunsky D, Yashin AY, et al. Phenylethanoid Glycosides From Teak Wood Knots And Their Antioxidant Activity. J Biol Active Prod Nat. 2016;6(4):272-81.
- 50. Zhang H, Tsao R. Dietary Polyphenols, Oxidative Stress And Antioxidant And Anti-Inflammatory Effects. Curr Opin Food Sci. 2016;8:33-42.
- 51. Herrera-Arellano A, Aguilar-Santamaria L, Garcia-Hernandez B, Nicasio-Torres P, Tortoriello J. Clinical trial of Cecropia obtusifolia and Marrubium vulgare Leaf Extracts On Blood Glucose And Serum Lipids In Type 2 Diabetics. Phytomed. 2004;11(7-8):561-6.
- 52. Loizzo MR, Saab AM, Tundis R, Menichini F, Bonesi M, Piccolo V, et al. In vitro Inhibitory Activities Of Plants Used In Lebanon Traditional Medicine Against Angiotensin Converting Enzyme (ACE) And Digestive Enzymes Related To Diabetes. J Ethnopharmacol. 2008;119(1):109-16.
Year 2019,
Volume: 6 Issue: 3, 281 - 292, 20.10.2019
Fatih Göğer
,
Gülmira Özek
,
Mehmet Tekin
Süleyman Yur
Temel Özek
References
- 1. Aytaç Z, Akgul G, Ekici M. A New Species of Marrubium (Lamiaceae) from Central Anatolia, Turkey. Turk J Bot. 2012;36:443-9.
- 2. Akgül G, Ketenoglu O. The new subspecies for the Flora of Turkey: Marrubium cephalanthum Boiss. & Noë subsp. akdağhicum (Lamiaceae). In: Ürgüp, Turkey: IXth National Conference on Ecology; 7-10 October;, Nevşehir: Nevşehir University Faculty of Science; 2009.
- 3. Tuylu M, Büyükkartal HN, Akgül G, Kalyoncu H. Marrubium lutescens Boiss. ve M. cephalanthum Boiss. & Noë subsp. akdaghicum (Lamiaceae)'un gövde ve yaprak özelliklerinin anatomik olarak karşılaştırılması. Süleyman Demirel Univ. J Nat Appl Sci. 2017;21(1):113‐7.
- 4. Firat M. Marrubium eriocephalum (Lamiaceae); a Species New to the Flora of Turkey, with Contributions to its Taxonomy. PhytoKeys. 2016(58):9-20.
- 5. Davis PH, Mill RR, Kit T. Flora of Turkey and the East Aegean Islands (Suppl. 1). Edinburgh: Edinburgh University Press; 1988. p. 202-3.
- 6. Meyre-Silva C, Cechinel-Filho V. A Review Of The Chemical And Pharmacological Aspects of the Genus Marrubium. Curr Pharm Des. 2010;16(31):3503-18.
- 7. Karioti A, Protopappa A, Megoulas N, Skaltsa H. Identification of Tyrosinase Inhibitors from Marrubium velutinum and Marrubium cylleneum. Bioorg Med Chem. 2007;15(7):2708-14.
- 8. Golmakani H, Rabbani Nasab H, Sharifan M, Kamali H, Yadollahi A. The Essential Oil Composition and Antibacterial Activity of Marrubium duabense Murata from North Khorassan Province, Iran. J Essent Oil Bear Plants. 2016;19(4):963-71.
- 9. Masoodi M, Ali Z, Liang S, Yin H, Wang W, Khan IA. Labdane Diterpenoids from Marrubium vulgare. Phytochem Lett. 2015;13:275-9.
- 10. Piozzi F, Bruno M, Rosselli S, Maggio A. The Diterpenoids of The Genus Marrubium (Lamiaceae). Nat Prod Commun. 2006;7:585-92.
- 11. Dehbashi Z, Mazaheri M, Saeedi S, Sabbagh SK. Antibacterial Activity of Marrubium vulgare L. Against Antibiotic Resistance Klebsiella pneumoniae Strains. Adv Herb Med. 2015;1(3):9-14.
- 12. Hamedeyazdan S, Sharifi S, Nazemiyeh H, Fathiazad F. Evaluating Antiproliferative And Antioxidant Activity of Marrubium crassidens. Adv Pharm Bull. 2014;4(Supp1):459-64.
- 13. De Jesus R, Cechinel-Filho V, Oliveira A, Schlemper V. Analysis of the Antinociceptive Properties of Marrubiin Isolated From Marrubium vulgare. Phytomed. 2000;7(2):111-5.
- 14. Boudjelal A, Henchiri C, Siracusa L, Sari M, Ruberto G. Compositional Analysis And In Vivo Anti-Diabetic Activity Of Wild Algerian Marrubium vulgare L. Infusion. Fitoterapia. 2012;83(2):286-92.
- 15. Namjoyan F, Azemi ME, Abdollahi E, Goudarzi N, Nikan K. Angiotensin I Converting Enzyme Inhibitory Activities Of Hydroalcoholic Extract of Nardostachys jatamansi, Prangos ferulacea and Marrubium vulgare. Jundishapur J Nat Pharm Prod. 2015;10(2):e17255.
- 16. Ettaya A, Dhibi S, Samout N, Elfeki A, Hfaiedh N. Hepatoprotective Activity Of White Horehound (Marrubium Vulgare) Extract Against Cyclophosphamide Toxicity In Male Rats. Can J Physiol Pharmacol. 2015;94(4):441-7.
- 17. Saad S, Ouafi S, Chabane D. Anti-Inflammatory And Acute Toxicity Evaluation Of Aqueous Infusion Extract Obtained From Aerial Parts of Marrubium deserti de Noé growing in Algeria. Afr J Tradit, Complement Altern Med. 2016;13(1):71-5.
- 18. Yousefi K, Soraya H, Fathiazad F, Khorrami A, Hamedeyazdan S, Maleki-Dizaji N, et al. Cardioprotective Effect Of Methanolic Extract Of Marrubium vulgare L. on Isoproterenol-Induced Acute Myocardial Infarction In Rats. Ind J Exp Biol. 2013;51(8):653-60.
- 19. Argyropoulou A, Samara P, Tsitsilonis O, Skaltsa H. Polar Constituents Of Marrubium Thessalum Boiss. & Heldr.(Lamiaceae) And Their Cytotoxic/Cytostatic Activity. Phytother Res. 2012;26(12):1800-6.
- 20. Pukalskas A, Venskutonis PR, Salido S, de Waard P, van Beek TA. Isolation, Identification And Activity Of Natural Antioxidants From Horehound (Marrubium Vulgare L.) Cultivated in Lithuania. Food Chem. 2012;130(3):695-701.
- 21. Letchamo W, Mukhopadhyay S. Variability in Chromosomes, Herb Yield, Essential Oil Content And Potentials Of Horehound For North American Commercial Production. J Horticult Sci. 1997;72(5):741-8.
- 22. Weel KG, Venskutonis PR, Pukalskas A, Gruzdiene D, Linssen JP. Antioxidant Activity Of Horehound (Marrubium vulgare L) Grown in Lithuania. Eur J Lipid Sci Tech. 1999;101(10):395-9.
- 23. Orhan IE, Belhattab R, Şenol F, Gülpinar A, Hoşbaş S, Kartal M. Profiling of cholinesterase inhibitory and antioxidant activities of Artemisia absinthium, A. herba-alba, A. fragrans, Marrubium vulgare, M. astranicum, Origanum vulgare subsp. glandulossum and Essential Oil Analysis Of Two Artemisia Species. Ind Crops Prod. 2010;32(3):566-71.
- 24. Tuzlaci E. A Dictionary of Turkish Plants. Melisa Matbaacilik: ALFA Press; 2006.
- 25. Song H-P, Zhang H, Fu Y, Mo H-y, Zhang M, Chen J, et al. Screening for Selective Inhibitors Of Xanthine Oxidase From Flos Chrysanthemum Using Ultrafiltration LC–MS Combined With Enzyme Channel Blocking. J Chromatogr B. 2014;961:56-61.
- 26. Kaurinovic B, Vlaisavljevic S, Popovic M, Vastag D, Djurendic-Brenesel M. Antioxidant Properties Of Marrubium Peregrinum L.(Lamiaceae) Essential Oil. Molecules. 2010;15(9):5943-55.
- 27. Sahpaz S, Garbacki N, Tits M, Bailleul F. Isolation and Pharmacological Activity Of Phenylpropanoid Esters From Marrubium vulgare. J Ethnopharmacol. 2002;79(3):389-92.
- 28. Essawy SS, Abo-Elmatty DM, Ghazy NM, Badr JM, Sterner O. Antioxidant and Anti-Inflammatory Effects Of Marrubium Alysson Extracts In High Cholesterol-Fed Rabbits. Saudi Pharm J. 2014;22(5):472-82.
- 29. Benkhnigue O, Ben Akka F, Salhi S, Fadli M, Douira A, Zidane L. Catalogue Des Plantes Médicinales Utilisées Dans Le Traitement Du Diabète Dans La Région d’Al Haouz-Rhamna (Maroc). J Anim Plant Sci. 2014;23(1):3539-68.
- 30. Orch H, Douira A, Zidane L. Étude Ethnobotanique Des Plantes Médicinales Utilisées Dans Le Traitement Du Diabète, Et Des Maladies Cardiaques Dans La Région d’Izarène (Nord du Maroc). J Appl Biosci. 2015;86(1):7940-56.
- 31. Tsukamoto K, Jackson IJ, Urabe K, Montague PM, Hearing V. A Second Tyrosinase-Related Protein, TRP-2, Is A Melanogenic Enzyme Termed Dopachrome Tautomerase. EMBO J. 1992;11(2):519-26.
- 32. Xu Y, Stokes AH, Freeman WM, Kumer SC, Vogt BA, Vrana KE. Tyrosine mRNA is Expressed In Human Substantia Nigra. Mol Brain Res. 1997;45(1):159-62.
- 33. Namjoyan F, Jahangiri A, Azemi ME, Arkian E, Mousavi H. Inhibitory Effects of Physalis alkekengi L., Alcea rosea L., Bunium persicum B. Fedtsch. and Marrubium vulgare L. on Mushroom Tyrosinase. Jundishapur J Nat Pharm Prod. 2015;10(1):1-6.
- 34. Brand-Williams W, Cuvelier M-E, Berset C. Use Of A Free Radical Method To Evaluate Antioxidant Activity. LWT-Food Sci Technol. 1995;28(1):25-30.
- 35. Re R, Pellegrini N, Proteggente A, Pannala A, Yang M, Rice-Evans C. Antioxidant Activity Applying An Improved ABTS Radical Cation Decolorization Assay. Free Rad Biol Med. 1999;26(9-10):1231-7.
- 36. Prior RL, Wu X, Schaich K. Standardized Methods For The Determination Of Antioxidant Capacity And Phenolics In Foods And Dietary Supplements. J Agric Food Chem. 2005;53(10):4290-302.
- 37. Marco GJ. A Rapid Method For Evaluation Of Antioxidants. J Am Oil Chem Soc. 1968;45(9):594-8.
- 38. Chen C-H, Chan H-C, Chu Y-T, Ho H-Y, Chen P-Y, Lee T-H, et al. Antioxidant Activity Of Some Plant Extracts Towards Xanthine Oxidase, Lipoxygenase And Tyrosinase. Molecules. 2009;14(8):2947-58.
- 39. Masuda T, Yamashita D, Takeda Y, Yonemori S. Screening For Tyrosinase Inhibitors Among Extracts Of Seashore Plants And Identification Of Potent Inhibitors From Garcinia subelliptica. Biosci Biotech Biochem. 2005;69(1):197-201.
- 40. Yang X-W, Huang M-Z, Jin Y-S, Sun L-N, Song Y, Chen H-S. Phenolics from Bidens bipinnata And Their Amylase Inhibitory Properties. Fitoterapia. 2012;83(7):1169-75.
- 41. Albano SM, Lima AS, Pedro MGMLG, Barroso JG, Figueiredo AC. Antioxidant, Anti-5-Lipoxygenase And Antiacetylcholinesterase Activities Of Essential Oils And Decoction Waters Of Some Aromatic Plants. Rec Nat Prod. 2012;6(1):35.
- 42. Michelis F, Tiligada E, Skaltsa H, Lazari D, Skaltsounis A-L, Delitheos A. Effects of the Flavonoid Pilloin Isolated From Marrubium Cylleneum On Mitogen-Induced Lymphocyte Transformation. Pharm Biol. 2002;40(4):245-8.
- 43. Çalis I, Hosny M, Khalifa T, Rüedi P. Phenylpropanoid Glycosides From Marrubium alysson. Phytochem. 1992;31(10):3624-6.
- 44. Hussain A, Perveen S, Malik A, Afza N, Iqbal L, Tareen RB. Urease Inhibitiory Flavone Glucosides from Marrubium anisodon. Pol J Chem. 2009;83(7):1329-35.
- 45. Mitreski I, Stanoeva JP, Stefova M, Stefkov G, Kulevanova S. Polyphenols in Representative Teucrium Species in the Flora of R. Macedonia: LC/DAD/ESI-MS (n) profile and content. Nat Prod Commun. 2014;9(2):175-80.
- 46. Kırmızıbekmez H, Montoro P, Piacente S, Pizza C, Dönmez A, Çalış İ. Identification by HPLC‐PAD‐MS and Quantification by HPLC‐PAD of Phenylethanoid Glycosides of Five Phlomis Species. Phytochem Anal. 2005;16(1):1-6.
- 47. Ulubelen A, Topcu G, Kolak U. Labiatae flavonoids and their bioactivity. In: Atta ur R, editor. Studies in Natural Products Chemistry. Vol. 30: Elsevier; 2005. p. 233-302.
- 48. Buckingham J, Munasinghe VRN. Dictionary of Flavonoids with CD-ROM: CRC Press; 2015.
- 49. Tsvetkov D, Dmitrenok A, Tsvetkov YE, Menshov V, Yashunsky D, Yashin AY, et al. Phenylethanoid Glycosides From Teak Wood Knots And Their Antioxidant Activity. J Biol Active Prod Nat. 2016;6(4):272-81.
- 50. Zhang H, Tsao R. Dietary Polyphenols, Oxidative Stress And Antioxidant And Anti-Inflammatory Effects. Curr Opin Food Sci. 2016;8:33-42.
- 51. Herrera-Arellano A, Aguilar-Santamaria L, Garcia-Hernandez B, Nicasio-Torres P, Tortoriello J. Clinical trial of Cecropia obtusifolia and Marrubium vulgare Leaf Extracts On Blood Glucose And Serum Lipids In Type 2 Diabetics. Phytomed. 2004;11(7-8):561-6.
- 52. Loizzo MR, Saab AM, Tundis R, Menichini F, Bonesi M, Piccolo V, et al. In vitro Inhibitory Activities Of Plants Used In Lebanon Traditional Medicine Against Angiotensin Converting Enzyme (ACE) And Digestive Enzymes Related To Diabetes. J Ethnopharmacol. 2008;119(1):109-16.