Tyrosinase inhibitory properties of phenylpropanoid glycosides and flavonoids from Teucrium polium L. var. gnaphalodes

Document Type: Original Article

Authors

1 Department of Pharmcognosy, School of Pharmacy, Mashhad University of Medical Sciences, Mashhad, Iran

2 Department of Nutrition, School of Medicine, Mashhad University of Medical Sciences, Mashhad, Iran

3 Eskitis Institute, Griffith University, Brisbane, QLD 4111, Australia

4 Department of Pharmacodynamics and Toxicology, School of Pharmacy, Mashhad University of Medical Sciences, Mashhad, Iran

5 Biotechnology Research Center, School of Pharmacy, Mashhad University of Medical Sciences, Mashhad, Iran

Abstract


Objective(s):
In food industry, the inhibition of tyrosinase is very important, because this enzyme catalyzes the oxidation of phenolic compounds found in fruits and vegetables into quinones, which contribute in undesirable color and taste of fruits and vegetables. Teucrium polium L. var. gnaphalodes (Lamiaceae), a wild-growing flowering plant that has many applications in food preparations and traditional medicine. In Persian language, this medicinal herb is called Kalpoureh.

Materials and Methods:
1D- and 2D-NMR experiments were used to determine the chemical structures of the isolated compounds. Antioxidant and tyrosinase inhibitory activities of the isolated compounds were evaluated using DPPH, FRAP and mushroom tyrosinase inhibition assays.

Results:
In this research, we isolated two phenylpropanoid glycosides including verbascoside and poliumoside and two flavonoids including jaranol and isorhoifolin using chromatographic techniques. We found promising antioxidant and anti-tyrosinase compounds from Teucrium polium L. var. gnaphalodes.

Conclusion:
To date, different compounds have been isolated and characterized from T. polium including terpenoids and flavonoids. But no phytochemical study has been reported from T. polium var. gnaphalodes. Poliumoside and jaranol showed promising antioxidant and tyrosinase inhibitory activities, respectively.

Keywords


1. Parvez S, Kang M, Chung HS, Bae H. Naturally occurring tyrosinase inhibitors: mechanism and applications in skin health, cosmetics and agriculture industries. Iran J Pharm Res 2007; 21:805-816.

2. Chang T-S. An updated review of tyrosinase inhibitors. Int J Mol Sci 2009; 10:2440-2475.

3. Bahramikia S, Yazdanparast R. Phytochemistry and medicinal properties of Teucrium polium L.(Lamiaceae). Iran J Pharm Res 2012; 26:1581-1593.

4. Mozaffarian V. A dictionary of Iranian plant names: Latin, English, Persian: Farhang Mo'aser; 1996.

5. Pacifico S, D’Abrosca B, Scognamiglio M, D’Angelo G, Gallicchio M, Galasso S, et al. NMR-based metabolic profiling and in vitro antioxidant and hepatotoxic assessment of partially purified fractions from Golden germander (Teucrium polium L.) methanolic extract. Food Chem 2012;135:1957-1967.

6. Bruno M, Bondì ML, Rosselli S, Maggio A, Piozzi F, Arnold NA. Neoclerodane diterpenoids from Teucrium montbretii Subsp. libanoticum and their absolute configuration. J Nat Prod 2002; 65:142-146.

7. Bruno M, Maria C, Rodríguez B, Omar AA. Guaiane sesquiterpenes from Teucrium leucocladum. Phytochemistry 1993;34:245-247.

8. Rizk A, Hammouda F, Rimpler H, Kamel A. Iridoids and flavonoids of Teucrium polium herb. Planta Med 1986; 52:87-88.

9. Kawashty S, El-Din EG, Saleh N. The flavonoid chemosystematics of two Teucrium species from Southern Sinai, Egypt. Biochem Syst Ecol 1999; 27: 657-660.

10. Wang K-H, Lin R-D, Hsu F-L, Huang Y-H, Chang H-C, Huang C-Y, et al. Cosmetic applications of selected traditional Chinese herbal medicines. J Ethnopharmacol 2006; 106:353-359.

11. Sulaiman SF, Sajak AAB, Ooi KL, Seow EM. Effect of solvents in extracting polyphenols and antioxidants of selected raw vegetables. J Food Comp Anal 2011; 24:506-515.

12. Kokotkiewicz A, Luczkiewicz M, Sowinski P, Glod D, Gorynski K, Bucinski A. Isolation and structure elucidation of phenolic compounds from Cyclopia subternata Vogel (honeybush) intact plant and in vitro cultures. Food Chem 2012;133:1373-1382.

13. Zhang X, Li B, Zhou M, Yuan X, Zhang G. Chemical constituents of Buddleja brachystachya diels. Chin J Appl Environ Biol 2006; 12:338.

14. Shaker KH, Morsy N, Zinecker H, Imhoff JF, Schneider B. Secondary metabolites from Calotropis procera (Aiton). Phytochem Lett 2010; 3:212-216.

15. El-Mawla A, Ahmed A, Ibraheim Z, Ernst L. Phenylethanoid glycosides from Barleria cristata L. callus cultures. Bull Pharm Sci, Assiut University. 2005; 28:199.

16. Andary C, Wylde R, Heitz A, Rascol J, Roussel J, Laffite C. Poliumoside, a caffeic glycoside ester from Teucrium belion. Phytochemistry 1985; 24:362-364.

17. De Marino S, Festa C, Zollo F, Incollingo F, Raimo G, Evangelista G, et al. Antioxidant activity of phenolic and phenylethanoid glycosides from Teucrium polium L. Food Chem 2012; 133:21-28.

18. Singh N, Shukla N, Singh P, Sharma R, Rajendran S, Maurya R, et al. Verbascoside isolated from Tectona grandis mediates gastric protection in rats via inhibiting proton pump activity. Fitoterapia 2010; 81:755-761.

19. Korkina L. Phenylpropanoids as naturally occurring antioxidants: from plant defense to human health. Cell Mol Biol 2007; 53:15-25.

20. Fu G, Pang H, Wong YH. Naturally occurring phenylethanoid glycosides: potential leads for new therapeutics. Curr Med Chem 2008; 15:2592-2613.

21. Shi L, Cao Y, Chen H. and JP Dong. Isolation and identification of two new secoiridoids of water-soluble chemical constituents from the fruits of Ligustrum lucidum Ait. Acta Pharm Sin B 1997; 32:442-446.

22. Chen Z-Y, Wong IYF, Leung MWS, He Z-D, Huang Y. Characterization of antioxidants present in bitter tea (Ligustrum pedunculare). J Agric Food Chem 2002; 50:7530-7535.

23. Okawa M, Kinjo J, Yang C-R, NONAKA G, NOHARA T. Antioxidative substances in the leaves of Ligustrum purpurascens. Nat Med 2001;55:209-212.

24. Chang L-W, Juang L-J, Wang B-S, Wang M-Y, Tai H-M, Hung W-J, et al. Antioxidant and antityrosinase activity of mulberry (Morus alba L.) twigs and root bark. Food Chem Toxicol 2011; 49:785-790.

25. Jimenez C, Riguera R. Phenylethanoid glycosides in plants: structure and biological activity. Nat Prod Rep 1994;11:591-606.

26. Nazemiyeh H, Rahman MM, Gibbons S, Nahar L, Delazar A, Ghahramani M-A, et al. Assessment of the antibacterial activity of phenylethanoid glycosides from Phlomis lanceolata against multiple-drug-resistant strains of Staphylococcus aureus. J Nat Med 2008; 62:91-95.

27. Koo KA, Sung SH, Park JH, Kim SH, Lee KY, Kim YC. In vitro neuroprotective activities of phenylethanoid glycosides from Callicarpa dichotoma. Planta Med 2005; 71:778.

28. Mapunya MB, Nikolova RV, Lall N. Melanogenesis and antityrosinase activity of selected South African plants. J Evid Based Complementary Altern Med 2012; 2012.

29. Karioti A, Protopappa A, Megoulas N, Skaltsa H. Identification of tyrosinase inhibitors from Marrubium velutinum and Marrubium cylleneum. Bioorg Med Chem Lett 2007; 15:2708-2714.

30. Iranshahi M, Rezaee R, Parhiz H, Roohbakhsh A, Soltani F. Protective effects of flavonoids against microbes and toxins: The cases of hesperidin and hesperetin. Life Sci 2015; 137: 125-132.

31. Roohbakhsh A, Parhiz H, Soltani F, Rezaee R, Iranshahi M. Neuropharmacological properties and pharmacokinetics of the citrus flavonoids hesperidin and hesperetin – A mini-review. Life Sci 2014; 113: 1-6.

32. Roohbakhsh A, Parhiz F, Soltani F, Rezaee R, Iranshahi M. Molecular mechanisms behind the biological effects of hesperidin and hesperetin for the prevention of cancer and cardiovascular diseases. Life Sci 2015; 124: 64-74.

33. Parhiz H, Roohbakhsh A, Soltani F, Rezaee R, Iranshahi M. Antioxidant and antiÔÇÉinflammatory properties of the citrus flavonoids hesperidin and hesperetin: an updated review of their molecular mechanisms and experimental models. Phytother Res 2015; 29: 323-331.

34. Saeidi I, Hadjmohammadi MR, Peyrovi M, Iranshahi M, Barfi B, Babaei AB,  Mohammaddoost A. HPLC determination of hesperidin, diosmin and eriocitrin in Iranian lime juice using polyamide as an adsorbent for solid phase extraction. J Pharm Biomed Anal 2011; 56:419-422.

35. Saewan N, Koysomboon S, Chantrapromma K. Anti-tyrosinase and anti-cancer activities of flavonoids from Blumea balsamifera DC. J Med Plants Res 2011; 5:1018-1025.