Research Article

Elucidation of Apigenin Derivatives from Ethyl Acetate Fraction of Stachys byzantina with Potent Antioxidant and Anti-Staphylococcus aureus Properties

Abstract

The Stachys genus is a medicinal plant, with 34 different species, from Lamiaceae family that grows in Irano-Anatolian plateau. There are 12 species of Stachys native to Iran. Some species of Stachys have been used in traditional medicine of Iran, Turkey, Italy, Greece, China, and Japan for the treatment of various diseases like inflammation, common cold, and etc. Some researchers have noted many biological effects, such as cytotoxic, antioxidant, immunomodulator, anti-inflammatory and anti-bacterial effects for the members of this genus. There are a few evidences on phytochemical constituents of S. byzanthinaThe aim of this study was phytochemical investigation of various extracts of this plant to obtain the most efficient fractions and compound(s) to study the antimicrobial effects of this plant. Separation and isolation of compounds was performed by various methods of chromatography. The structure of each compound was identified by spectroscopic methods.Antimicrobial studies were performed on different fractions of S. byzantina by microdilution method and to determine the Minimum Inhibitory Concentration (MIC), agar well diffusion was done.Ethyl acetate fraction has the highest total phenol contents (1082.05 mg GAE/g fraction) and antioxidant capacity (IC50= 1.23 mg/ml). Also, ethyl acetate fraction, the most potential fraction of S. byzanthina, was demonstrated the largest inhibition zone (17.5 ± 0.7 mm) with 5 mg/ml in MIC against Staphylococcus auresus.Apigenin and its derivatives were isolated from this fraction and according to literature; they can be responsible for antibacterial activity of this fraction of S. byzanthina.

Zargari A. Medicinal plants. Tehran University of Medical Sciences 1997.

Yamamoto R, Miyade T, Ueno A. Stachyssaponins I-VIII, new oleanane-type triterpene saponins from Stachys riederi Chamisso. Chem Pharm Bull 1994;42:1291-1296.

Adinolfi M, Barone G, Lanzetta R, Laonigro G, Mangoni L, et al. Diterpenes from Stachys recta. J Nat Prod 1984;47:541-543.

Piozzi F, Bruno M. Diterpenoids from roots and aerial parts of the genus Stachys. Rec Nat Prod 2011;5:1-11.

Çalis İ, Başaran AA, Saracogˇlu İ, St O. Iridoid and phenylpropanoid glycosides from Stachys macrantha. Phytochemistry 1992;31:167-169.

Tomou EM, Barda C, Skaltsa H. Genus Stachys: A review of traditional uses, phytochemistry and bioactivity. Medicines 2020;7:63.

El-Ansari M, Abdalla M, Saleh N, Barron D, Le Quéré JL. Flavonoid constituents of Stachys aegyptiaca. Phytochemistry 1991;30:1169-1173.

Nazemiyeh H, Shoeb M, Movahhedin N, Kumarasamy Y, Talebpour AH, et al. Phenolic compounds and their glycosides from Stachys schtschegleevii (Lamiaceae). Biochem Syst Ecol 2006;9:721-723.

Delazar A, Celik S, Göktürk R, Unal O, Nahar L, et al. Two acylated flavonoid glycosides from Stachys bombycina, and their free radical scavenging activity. Die Pharmazie-An Int J Pharm Sci 2005;60:878-880.

Miyase T, Yamamoto R, Ueno A. Phenylethanoid glycosides from Stachys officinalis. Phytochemistry 1996;43:475-459.

Nishimura H, Sasaki H, Inagaki N, Masao C, Chen Z, et al. Nine phenethyl alcohol glycosides from Stachys sieboldii. Phytochemistry 1991;30:965-969.

Ristic N, Lazarevic J, Radulovic N, Palic R. Antimicrobial activity of the essential oils of selected Stachys species. Chem Nat Comp 2008;44:522-525.

Kiashi F, Hadjiakhoondi A, Tofighi Z, Khanavi M, Ajani Y, et al. Compositions of essential oils and some biological properties of Stachys laxa Boiss. & Buhse and S. byzantina K. Koch. Res J Pharmacogn 2021;8:5-15.

Bahadori MB, Zengin G, Dinparast L, Eskandani M. The health benefits of three Hedgenettle herbal teas (Stachys byzantina, Stachys inflata, and Stachys lavandulifolia)-profiling phenolic and antioxidant activities. Euro J Integr Med 2020;36:101134.

Kartsev V, Stepanichenko N, Auelbekov S. Chemical composition and pharmacological properties of plants of the genusStachys. Chem Nat Comp 1994;30:645-654.

Maleki N, Garjani A, Nazemiyeh H, Nilfouroushan N, Sadat AE, et al. Potent anti-inflammatory activities of hydroalcoholic extract from aerial parts of Stachys inflata on rats. J Ethnopharmacol 2001;75:213-218.

Khanavi M, Safavi M, Siavoshi F, Fallah Tafti A, Hajimahmoodi M, et al. Evaluation of anti-Helicobacter pylori activity of methanol extracts of some species of Stachys and Melia. J Med Plants 2008;7:74-80.

Tundis R, Peruzzi L, Menichini F. Phytochemical and biological studies of Stachys species in relation to chemotaxonomy: a review. Phytochemistry 2014;102:7-39.

Duarte MCT, Figueira GM, Sartoratto A, Rehder VLG, Delarmelina C. Anti-Candida activity of Brazilian medicinal plants. J Ethnopharmacol 2005;97:305-311.

Skaltsa HD, Lazari DM, Chinou IB, Loukis AE. Composition and antibacterial activity of the essential oils of Stachys candida and S. chrysantha from southern Greece. Planta Medica 1999;65:255-256.

Lazarević JS, Ðorđević AS, Kitić DV, Zlatković BK, Stojanović GS. Chemical composition and antimicrobial activity of the essential oil of Stachys officinalis (L.) Trevis.(Lamiaceae). Chem Biodivers 2013;10:1335-1349.

Saeedi M, Morteza-Semnani K, Mahdavi M, Rahimi F. Antimicrobial studies on extracts of four species of Stachys. Indian J Pharm Sci 2008;70:403-406.

Mahboubi A, Mojab F, Kamalinejad M, Moghadam ziabbary S. Evaluation of antimicrobial effect of ethanol and chloroform extracts of Stachys byzantina. Res Pharm Sci 2012;7:750.

Háznagy-Radnai E, Czigle S, Zupkó I, Falkay G, Mathe I. Comparison of antioxidant activity in enzyme-independent system of six Stachys species. Fitoterapia 2006;77:521-524.

Morteza-Semnani K, Saeedi M, Shahani S. Antioxidant activity of the methanolic extracts of some species of Phlomis and Stachys on sunflower oil. Afr J Biotechnol 2006;5:2428-2432.

Jassbi AR, Miri R, Asadollahi M, Javanmardi N, Firuzi O. Cytotoxic, antioxidant and antimicrobial effects of nine species of woundwort (Stachys) plants. Pharm Biol 2014;52:62-67.

Vundać VB, Brantner AH, Plazibat M. Content of polyphenolic constituents and antioxidant activity of some Stachys taxa. Food Chem 2007;104:1277-1281.

Tofighi Z, Ghazi SN, Hadjiakhoondi A, Yassa N. Determination of cardiac glycosides and total phenols in different generations of Securigera securidaca suspension culture. Res J Pharmacogn 2016:2:25-31.

Tofighi Z, Alipour F, Yassa N, Hadjiakhoondi A, Hadavinia H, et al. Chemical composition and antioxidant activity of Otostegia persica essential oil from Iran. Int J Essen Oil Ther 2009;3:45-48.

Goodarzi S, Hadjiakhoondi A, Yassa N, Khanavi M, Tofighi Z. Essential oils chemical composition, antioxidant activities and total phenols of Astrodaucus persicus. Iran J Basic Med Sci 2016;19:159-165.

Lazarević JS, Palić RM, Radulović NS, Ristić NR, Stojanović GS. Chemical composition and screening of the antimicrobial and anti-oxidative activity of extracts of Stachys species. J Serb Chem Soc 2010;75:1347-1359.

Mükemre M, Behçet L, Çakılcıoğlu U. Ethnobotanical study on medicinal plants in villages of Çatak (Van-Turkey). J Ethnopharmacol 2015;166:361-374.

Pritsas A, Tomou EM, Tsitsigianni E, Papaemmanouil CD, Diamantis DA, et al. Valorisation of stachysetin from cultivated Stachys iva Griseb. as anti-diabetic agent: A multi-spectroscopic and molecular docking approach. J Biomol Struct Dy 2021;39:6452-6466.

Lucchetti L, Zitti S, Taffetani F. Ethnobotanical uses in the Ancona district (Marche region, Central Italy). J Ethnobiol Ethnomed 2019;15:1-33.

Lee J, Wu W, Lim S. Effect of extracts from Stachys sieboldii Miq. on cellular reactive oxygen species and glutathione production and genomic DNA oxidation. Asian Pac J Trop Biomed 2018;8:485-489.

Sarikurkcu C, Kocak MS, Uren MC, Calapoglu M, Tepe AS. Potential sources for the management global health problems and oxidative stress: Stachys byzantina and S. iberica subsp. iberica var. densipilosa. Eur J Integr Med 2016;8:631-637.

Asnaashari S, Delazar A, Alipour SS, Nahar L, Williams AS, et al. Chemical composition, free-radical-scavenging and insecticidal activities of the aerial parts of Stachys byzantina. Arch Biol Sci 2010;62:653-662.

Stamatis G, Kyriazopoulos P, Golegou S, Basayiannis A, Skaltsas S, et al. In vitro anti-Helicobacter pylori activity of Greek herbal medicines. J Ethnopharmacol 2003;88:175-179.

Abichandani M, Nahar L, Singh P, Chitnis R, Nazemiyeh H, et al. Antibacterial and free-radical-scavenging properties of Stachys schtschegleevii (Lamiaceae). Arch Biol Sci 2010;62:941-945.

Toplan GG, TAŞKIN T, Kara EM, Genç GE. Antioxidant and antimicrobial activities of various extracts from Stachys cretica subsp. bulgarica Rech. f., Stachys byzantina K. Koch and Stachys thirkei K. Koch. İstanbul J Pharm 2021;51:341-347.

Noshad M. The antibacterial effect of Stachys byzantina extract on a number of pathogenic bacteria using agar dilution and Cylinder-plate methods. J Food Sci Technol 2021;17:33-42.

Hirano R, Sasamoto W, Matsumoto A, Itakura H, Igarashi O, et al. Antioxidant ability of various flavonoids against DPPH radicals and LDL oxidation. J Nutr Sci Vitaminol 2001;47:357-362.

Sharififar F, Dehghn-Nudeh G, Mirtajaldini M. Major flavonoids with antioxidant activity from Teucrium polium L. Food Chem 2009;112:885-888.

Sghaier MB, Skandrani I, Nasr N, Franca MGD, Chekir-Ghedira L, et al. Flavonoids and sesquiterpenes from Tecurium ramosissimum promote antiproliferation of human cancer cells and enhance antioxidant activity: A structure–activity relationship study. Environ Toxicol Pharmacol 2011;32:336-348.

Morimoto Y, Baba T, Sasaki T, Hiramatsu K. Apigenin as an anti-quinolone-resistance antibiotic. Inter J Antimicrob Agents 2015;46:666-673.

Liu R, Zhang H, Yuan M, Zhou J, Tu Q, et al. Synthesis and biological evaluation of apigenin derivatives as antibacterial and antiproliferative agents. Molecules 2013;18:11496-114511.

Sato Y, Suzaki S, Nishikawa T, Kihara M, Shibata H, et al. Phytochemical flavones isolated from Scutellaria barbata and antibacterial activity against methicillin-resistant Staphylococcus aureus. J Ethnopharmacol 2000;72:483-488.

Cha S, Kim G, Cha J. Synergistic antimicrobial activity of apigenin against oral pathogens. Inter J Eng Res Sci 2016;2:27-37.

Eumkeb G, Chukrathok S. Synergistic activity and mechanism of action of ceftazidime and apigenin combination against ceftazidime-resistant Enterobacter cloacae. Phytomedicine 2013;20:262-269.

Nayaka HB, Londonkar RL, Umesh MK, Tukappa A. Antibacterial attributes of apigenin, isolated from Portulaca oleracea L. Inter J Bacteriol 2014;2014:175851.

Demirtas I, Gecibesler IH, Yaglioglu AS. Antiproliferative activities of isolated flavone glycosides and fatty acids from Stachys byzantina. Phytochem Lett 2013;6:209-214.

Files
IssueVol 8, No 2, 2023 QRcode
SectionResearch Article(s)
DOI https://doi.org/10.18502/tim.v8i2.13082
Keywords
Stachys byzantine Antibacterial agents Ethyl acetate fraction Staphylococcus aureus Minimum Inhibitory Concentration (MIC) Apigenin

Rights and permissions
Creative Commons License This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.
How to Cite
1.
Pirali Hamedani M, Aram F, Hadjiakhoondi A, Samadi N, Tavakoli S, Kiashi F, Goodarzi S, Tofighi Z. Elucidation of Apigenin Derivatives from Ethyl Acetate Fraction of Stachys byzantina with Potent Antioxidant and Anti-Staphylococcus aureus Properties. Trad Integr Med. 2023;8(2):156-163.