PHYTOCHEMICAL STUDY OF BIOACTIVE CONSTITUENTS FROM SATUREJA MONTANA L. GROWING IN EGYPT AND THEIR ANTIMICROBIAL AND ANTIOXIDANT ACTIVITIES
Â Objective: This work aimed to investigate the lipid constituents and flavonoidal compounds of Satureja montana, in addition to evaluation of different extracts and/or isolated compounds as antimicrobials and antioxidants.
Methods: The volatile and lipid constituents were extracted with n-hexane by partition from hydroalcoholic extract of S. montana L. aerial parts, after then were fractionated to unsaponifiable matters and fatty acid methyl esters which were identified by gasâ€“liquid chromatography and/or gas chromatographyâ€“mass spectrometry. The phenolic constituents were isolated from the ethyl acetate fraction of the aqueous methanolic extract of the aerial parts of the plant. The antimicrobial activity of different extracts and the isolated compounds was evaluated against Gram-positive, Gram-negative bacteria, yeast, and fungus using a modified Kirby-Bauer disc diffusion method.
Results: The identified compounds are luteolin-7-rhamnoside-4â€™-O-Î²-glucopyranoside (1), quercetin-3-O-Î±-L-rhamnopyranoside (2), quercetin- 7-O-glucopyranoside (3), luteolin-7-O-glucopyranoside (4), 5-hydroxy-6,7,8,4â€™-tetramethoxy flavone (5), gallic acid (6), 2,3-hexahydroxydiphenoyl 1-galloyl glucopyranoside (7), and quercetin (8). The structure of all isolated compounds was established using different chromatographic and spectroscopic measurements (PC, thin-layer chromatography, ultraviolet [UV], 1D, 2D-nuclear magnetic resonance, and MS). Compound-2 showed the highest antibacterial activity against all the tested microorganisms. Hydroalcoholic extract exhibited high antioxidant activity (87.7%). On the other hand, hexane fraction showed a low antioxidant activity (46.4%), in addition to the compound-8 showed the highest antioxidant activity (96.27%) in 2,2-diphenyl-1-picrylhydrazyl assay.
Conclusion: It can be concluded that the hydroalcoholic extract of S. montana showed significant antimicrobial and antioxidant activity.
2. Leporatti ML, Ivancheva S. Preliminary comparative analysis of medicinal plants used in the traditional medicine of Bulgaria and Italy. J Ethnopharmacol 2003;87:123-42.
3. Radonic A, Milos M. Chemical composition and in vitro evaluation of antioxidant effect of free volatile compounds from Satureja montana L. Free Radic Res 2003;37:673-9.
4. SkoÄibuÅ¡iÄ‡ M, BeÅ¾iÄ‡ N. Chemical composition and antidiarrhoeal activities of winter savory (Satureja montana L.) essential oil. Pharm Biol 2003;41:622-6.
5. SkoÄibuÅ¡iÄ‡ M, BeÅ¾iÄ‡ N. Chemical composition and antimicrobial variability of Satureja montana L. Essential oils produced during ontogenesis. J Essent Oil Res 2004;16:387-391.
6. Oussalah M, Caillet S, Saucier L, Lacroix M. Inhibitory effects of selected plant essential oils on the growth of four pathogenic bacteria: E. Coli O157:H7, Salmonella typhimurium, St. aureus and Listeria monocytogenes. Food Control 2007;18:414-20.
7. Ä†avar S, MaksimoviÄ‡ M, Å oliÄ‡ M, JerkoviÄ‡-MujkiÄ‡ E, BeÅ¡ta R. Chemical composition and antioxidant and antimicrobial activity of two Satureja essential oils. Food Chem 2008;111:648-53.
8. Zavatti M, Zanoli P, Benelli A, Rivasi M, Baraldi C, Baraldi M, et al. Experimental study on Satureja montana as a treatment for premature ejaculation. J Ethnopharmacol 2011;133:629-33.
9. Haloc EI, Toska V, Baldisserotto A, Goci E, Vertuani S, Manfredini S. Evaluation of antifungal activity of Satureja montana essential oil before and after inclusion in beta-cyclodextrin. Int J Pharm Pharm Sci 2016;6(7):189-91.
10. Gohari AR, Hadjiakhoondi A, Sadat-Ebrahimi SE, Saeidnia S, Shafiee A. Cytotoxic terpenoids from Satureja macrantha CA Mey. DARU 2005;13:177-81.
11. Moghaddam FM, Farimani MM, Salahvarzi S, Amin G. Chemical constituents of dichloromethane extract of cultivated Satureja khuzistanica. Evid Based Complement Alternat Med 2007;4:95-8.
12. Gohari AR, Saeidnia S, Gohari MR, Moradi-Afrapoli F, Malmir M, Hadjiakhoondi A, et al. Bioactive flavonoids from Satureja atropatana bonge. Nat Prod Res 2009;23:1609-14.
13. Saeidnia S, Nourbakhsh MS, Gohari AR, Davood A. Isolation and identification of the main compounds of Satureja sahendica Bornm. Aust J Basic Appl Sci 2011;5:1450-3.
14. Gohari AR, Ostad SN, Moradi-Afrapoli F, Malmir M, Tavajohi S, Akbari H. Evaluation of the cytotoxicity of Satureja spicigera and itâ€™s main compounds. Sci World J 2012;2012:203861.
15. Sanja Ä†, Marija EÅ , Milka M. Chemical composition and antioxidant activity of two Satureja species from Mt. Biokovo. Bot Serbia 2013;37:159-16.
16. Malmir M, Gohari AR, Saeidnia S, Silva O. A new bioactive monoterpene-flavonoid from Satureja khuzistanica. Fitoterapia 2015;105:107-12.
17. Ahamad RG, Abbas H, Seyed E, Sadat E, Soodabeh S, Abbas S. Cytoxic terpenoids from S. Macrantha. DARU 2005;13:4.
18. Melpomeni S, Renee JG, Geoffrey C.K. Surface flavonoids in S. thymbra and S. spinosa (Lamiaceae). Biochem Syst Ecol 2005;33:541-4.
19. GÃ¶ren AC, Bilsel G, Altun M, Satil F, Dirmenci T. Fatty acid composition of seeds of Satureja thymbra and S. cuneifolia. Z Naturforsch C 2003;58:502-4.
20. Bauer AW, Kirby WM, Sherris C, Turck M. Antibiotic susceptibility testing by a standardized single disk method. Am J Clin Pathol 1966;45:493-6.
21. National Committee for Clinical Laboratory Standards. Reference Method for Broth Dilution Antifungal Susceptibility Testing of Conidium-Forming Filamentous Fungi: Proposed Standard M 38-A. Wayne, PA, USA: NCCLS; 2002.
22. National Committee for Clinical Laboratory Standards. Method for antifungal disk Diffusion Susceptibility Testing of Yeast: Proposed Guideline M44-P. Wayne, PA, USA: NCCLS; 2003.
23. Mohammed RS, El Souda SS, Taie HA, Moharam ME, Shaker KH. Antioxidant, antimicrobial activities of flavonoids glycoside from Leucaena leucocephala leaves. J Appl Pharm Sci 2015;5:138-47.
24. Braca A, De Tommasi N, Di Bari L, Pizza C, Politi M, Morelli I. Antioxidant principles from Bauhinia tarapotensis. J Nat Prod 2001;64:892-5.
25. Hanene M, Rihab BS, Donia M, Sami Z, Amina B, Emna A. Chemical composition and cytotoxic and antioxidant activities of Satureja montana L. Essential oil and Its antibacterial potential against Salmonella Spp. Strains J Chem 2013;2013:9.
26. Harbone JB. Phytochemical Methods. London: Chapman and Hall; 1984.
27. Mabry TJ, Markham KR, Thomas MB. The Systematic Identification of Flavonoids. New York: Springer-Verlag; 1970.
28. Nawwar MA, Hussein SA, Merfort I. NMR spectral analysis of polyphenenolics from Punica granatum. Phytochemistry 1994;36:793- 8.
29. Luger P, Weber M, Kashino S, Amakura Y, Yoshida T, Okuda T, et al. Structure of the tannin geraniin based on conventional X-ray data at 295 K and on synchrotron data at 293 and 120 K. Acta Cryst 1998;B54:687- 94.
30. Ito H, Iguchi A, Hatano T. Identification of urinary and intestinal bacterial metabolites of ellagitannin geraniin in rats. J Agric Food Chem 2008;56:393-400.
31. Ayaz F, Haylrlloglu AS, Alpay KS, Gruz J, Valentovaâ€™ K, Ulrichovaâ€™ J, et al. Phenolic acid contents of kale (Brassica oleraceae L. Var. Acephala DC.) extracts and their antioxidant and antimicrobial activities. Food Chem 2008;107:19-25.
32. Rahman AA, Moon SS. Antimicrobial phenolic derivatives from Dendranthema zawadskii var. Latilobum kitamura (Asteraceae). Arch Pharm Res 2007;30:1374-9.
33. Kelly EH, Anthony RT, Dennis JB. The B-ring hydroxyl flavonoid antioxidants: Chemistry, metabolism and structure-activity relationships. J Nutr Biochem 2002;13:572-84.
34. Kamsala RV, Lepakshi BMD, Padma Y, Venkata RR. Studies on antimicrobial and antioxidant properties of leaf extracts of Syzygium alternifolium. Int J Pharm Pharm Sci 2015;7:139-43.
35. Sekher Pannala A, Chan TS, Oâ€™Brien PJ, Rice-Evans CA. Flavonoid B-ring chemistry and antioxidant activity: Fast reaction kinetics. Biochem Biophys Res Commun 2001;282:1161-8.
36. Burda S, Oleszek W. Antioxidant and antiradical activities of flavonoids. J Agric Food Chem 2001;49:2774-9.
37. Hu JP, Calomme M, Lasure A, De Bruyne T, Pieters L, Vlietinck A, et al. Structure-activity relationship of flavonoids with superoxide scavenging activity. Biol Trace Elem Res 1995;47:327-31.
38. Van Acker SA, De Groot MJ, van den Berg DJ, Tromp MN, den Kelder GD, van der Vijgh WJ, et al. A quantum chemical explanation of the antioxidant activity of flavonoid. Chem Res Toxicol 1996;9:1305-12.
39. Arora A, Nair MG, Strasburg GM. Structure-activity relationships for antioxidant activities of a series of flavonoids in a liposomal system. Free Radic Biol Med 1998;24:1355-63.
The publication is licensed under CC By and is open access. Copyright is with author and allowed to retain publishing rights without restrictions.