Phytochemical Constituents and Biological Activities of Salvia suffruticosa

Document Type : Original paper

Authors

1 Department of Pharmacognosy, Faculty of Pharmacy and Medicinal Plants Research Center, Tehran University of Medical Sciences, Tehran, Iran. Persian Medicine and Pharmacy Research Center, Tehran University of Medical Sciences, Tehran, Iran.

2 Department of Pharmacognosy, Faculty of Pharmacy and Medicinal Plants Research Center, Tehran University of Medical Sciences, Tehran, Iran.

3 Persian Medicine and Pharmacy Research Center, Tehran University of Medical Sciences, Tehran, Iran. Department of Medicinal Chemistry, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran.

4 Department of Biotechnology, Iranian Research Organization for Science and Technology, Tehran, Iran.

5 Department of Drug and Food Control, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran.

6 Persian Medicine and Pharmacy Research Center, Tehran University of Medical Sciences, Tehran, Iran.

7 Department of Pharmacognosy, Faculty of Pharmacy and Medicinal Plants Research Center, Tehran University of Medical Sciences, Tehran, Iran. Persian Medicine and Pharmacy Research Center, Tehran University of Medical Sciences, Tehran, Iran. Faculty of Land and Food Systems, University of British Columbia, Vancouver, BC, Canada.

Abstract

Background and objectives: Salvia suffruticosa is a perennial plant from Lamiaceae family. Many Salvia species have been employed as medicinal plants; despite the medicinal potentials of S. suffruticosa, there is limited studies regarding its phytochemical profile or biological properties. The aim of the present study was to investigate the chemical constituents of the essential oil and extract of the plant and evaluate its biological activities. Methods: Essential oil from the aerial parts of the plant was extracted by hydrodistillation and analyzed using gas chromatography/mass spectroscopy. Isolation of compounds from methanol and petroleum ether fractions was achieved by using column chromatography with different stationary phases. The structures of the isolated compounds were elucidated by NMR techniques. Cytotoxicity potentials were evaluated using MTT assay and acridine orange/ethidium bromide staining method. Antioxidant activity was assessed by DPPH method. Results: Hydrocarbon sesquiterpenes were identified as the predominant components of the oil, with β-caryophyllene (27.35%), bicyclogermacrene (22.15%), germacrene-D (9.49%) and β-farnesene (9.08%) as the major constituents. Phytochemical analysis of the extract resulted in isolation of lupeol (1), β-sitosterol (2), stigmasterol (3), caffeic acid (4) and 1-feruloyl-β-D-glucopyranose (5). Among the tested samples, lupeol demonstrated the most potent inhibitory activity toward breast cancer cell lines including MCF-7, T-47D and MDA-MB-231 with IC50 values equal to 33.38±2.6, 36.70±3.1 and 23.66±1.4 μg/mL, respectively; caffeic acid with IC50 value of 12.1±1.2 μg/mL showed the most potent radical scavenging activity. Conclusion: The results of this study suggested S. suffruticosa as a promising source of bioactive compounds useful in prevention and treatment of cancer.

Keywords

Main Subjects


[1] Harley R, Atkins S, Budantsev A, Kadereit J. The families and genera of vascular plants, Lamiales. Berlin: Springer, 2004.
[2] Ulubelen A, Topçu G. Chemical and biological investigations of Salvia species growing in Turkey. Stud Nat Prod Chem. 1997; 20: 659-718.
[3] Imanshahidi M, Hosseinzadeh H. The pharmacological effects of Salvia species on the central nervous system. Phytother Res. 2006; 20(6): 427-437.
[4] Kintzios SE. Sage: the genus Salvia. Amsterdam: CRC Press, 2003.
[5] Jamzad Z. Flora of Iran: Lamiaceae. Tehran:  Research Institute of Forests & Rangelands Press, 2012.
[6] Tuncturk M, Eryigit T, Sekeroglu N, Ozgokce F. Chemical characterization of some wild edible plants of eastern region of Anatolia, Turkey. Am J Essent Oil Nat Prod. 2015; 2(5): 38-41.
[7] Norouzi-Arasi H, Yavari I, Chalabian F, Baghaii P, Kiarostami V, Nasrabadi M, Aminkhani A. Volatile constituents and antimicrobial activities of Salvia suffruticosa Montbr. & Auch. ex Benth. from Iran. Flavour frag J. 2005; 20(6): 633-636.
[8] Şenol FS, Orhan I, Celep F, Kahraman A, Doğan M, Yilmaz G, Şener B. Survey of 55 Turkish Salvia taxa for their acetylcholinesterase inhibitory and antioxidant activities. Food Chem. 2010; 120(1): 34-43.
[9] Delnavazi MR, Soleimani M, Hadjiakhoondi A, Yassa N. Isolation of phenolic derivatives and essential oil analysis of Prangos ferulacea (L.) Lindl. aerial parts. Iran J Pharm Res. 2017; 16(S): 207-215.
[10] Adams RP. Identification of essential oil components by gas chromatography/mass spectroscopy. Carol Stream: Allured Publishing Corporation, 1995.
[11] Khosravi Dehaghi N, Ostad S, Maafi N, Pedram S, Ajani Y, Hadjiakhoondi A, Khanavi M. Cytotoxic activity of the essential oil of Salvia verticillata L. Res J Pharmacogn. 2014; 1(3): 27-33.
[12] Mohammadi-Khanaposhtani M, Safavi M, Sabourian R, Mahdavi M, Pordeli M, Saeedi M, Ardestani S, Foroumadi A, Shafiee A, Akbarzadeh T. Design, synthesis, in vitro cytotoxic activity evaluation, and apoptosis-induction study of new 9 (10H)-acridinone-1, 2, 3-triazoles. Molec Divers. 2015; 19(4): 787-795.
[13] Delnavazi M, Tavakoli S, Rustaie A, Batooli H, Yassa N. Antioxidant and antibacterial activities of the essential oils and extracts of Dorema ammoniacum roots and aerial parts. Res J Pharmacogn. 2014; 1(4): 11-18.
[14] Sholichin M, Yamasaki K, Kasai R, Tanaka O. 13C Nuclear magnetic resonance of lupane-type triterpenes, lupeol, betulin and betulinic acid. Chem Pharm Bull. 1980; 28(3): 1006-1008.
[15] Goad J, Akihisa T. Analysis of sterols. London: Chapman & Hall, 1997.
[16] Jeong CH, Jeong HR, Choi GN, Kim DO, Lee U, Heo HJ. Neuroprotective and anti-oxidant effects of caffeic acid isolated from Erigeron annuus leaf. Chin Med. 2011; 6(1): 25.
[17] Miyake Y, Mochizuki M, Okada M, Hiramitsu M, Morimitsu Y, Osawa T. Isolation of antioxidative phenolic glucosides from lemon juice and their suppressive effect on the expression of blood adhesion molecules. Biosci Biotechnol Biochem. 2007; 71(8): 1911-1919.
[18] Wallaart TE, Pras N, Beekman AC, Quax WJ. Seasonal variation of artemisinin and its biosynthetic precursors in plants of Artemisia annua of different geographical origin: proof for the existence of chemotypes. Planta Med. 2000; 66(1): 57-62.
[19] Keefover-Ring K, Thompson JD, Linhart YB. Beyond six scents: defining a seventh Thymus vulgaris chemotype new to southern France by ethanol extraction. Flav Frag J. 2009; 24(3): 117-122.
[20] Viljoen AM, Petkar S, Van Vuuren SF, Figueiredo AC, Pedro LG, Barroso JG. The Chemo-geographical variation in essential oil composition and the antimicrobial properties of "wild mint" Mentha longifolia subsp. polyadena (Lamiaceae) in Southern Africa. J Essent Oil Res. 2006; 18(1):  60-65.
[21] Singh S, Tewari G, Pande C, Singh C. Variation in essential oil composition of Ocimum americanum L. from north-western Himalayan region. J Essent Oil Res. 2013; 25(4): 278-290.
[22] Marcial G, de Lampasona MP, Vega MI, Lizarraga E, Viturro CI, Slanis A, Juárez MA, Elechosa MA, Catalán CAN. Intraspecific variation in essential oil composition of the medicinal plant Lippia integrifolia (Verbenaceae). Evidence for five chemotypes. Phytochemistry. 2016; 122: 203-212.
[23] Sefidkon F, Mirza M. Chemical composition of the essential oils of two Salvia species from Iran, Salvia virgata Jacq. and Salvia syriaca L. Flavour Frag J. 1999; 14(1): 45-46.
[24] Torres ME, Velasco-Negueruela A, Pérez-Alonso MJ, Pinilla MG. Volatile constituents of two Salvia species grown wild in Spain. J Essent Oil Res. 1997; 9(1): 27-33.
[25] Liang Q, Liang ZS, Wang JR, Xu WH. Essential oil composition of Salvia miltiorrhiza flower. Food Chem. 2009; 113(2): 592-594.
[26] Rustaiyan A, Masoudi S, Monfared A, Komeilizadeh H. Volatile constituents of three Salvia species grown wild in Iran. Flavour Frag J. 1999; 14(5): 276-278.
[27] Asgarpanah J, Oveyli E, Alidoust S. Volatile components of the endemic species Salvia sharifii Rech. f. & Esfand. J Essent Oil Bear Plants. 2017; 20(2): 578-582.
[28] Haznedaroglu MZ, Karabay NU, Zeybek U. Antibacterial activity of Salvia tomentosa essential oil. Fitoterapia. 2001; 72(7): 829-831.
[29] Delamare AP, Moschen-Pistorello IT, Artico L, Atti-Serafini L, Echeverrigaray S. Antibacterial activity of the essential oils of Salvia officinalis L. and Salvia triloba L. cultivated in South Brazil. Food Chem. 2007; 100(2): 603-608.
[30] Valko M, Leibfritz D, Moncol J, Cronin MT, Mazur M, Telser J. Free radicals and antioxidants in normal physiological functions and human disease. ‎Int J Biochem Cell Biol. 2007; 39(1): 44-84.
[31] Rahimi R, Nikfar S, Larijani B, Abdollahi M. A review on the role of antioxidants in the management of diabetes and its complications. Biomed Pharmacother. 2005; 59(7): 365-373.
[32] Stocker R, Keaney JF. Role of oxidative modifications in atherosclerosis. Physiol Rev. 2004; 84(4): 1381-1478.
[33] Chung TW, Moon SK, Chang YC, Ko JH, Lee YC, Cho G, Kim SH, Kim JG, Kim CH. Novel and therapeutic effect of caffeic acid and caffeic acid phenyl ester on hepatocarcinoma cells: complete regression of hepatoma growth and metastasis by dual mechanism. FASEB J. 2004; 18(14): 1670-1681.
[34] Moriarty DM, Huang J, Yancey CA, Zhang P, Setzer WN, Lawton RO, Bates RB, Caldera S. Lupeol is the cytotoxic principle in the leaf extract of Dendropanax cf. querceti. Planta Med. 1998; 64(4): 370-372.
[35] Saleem M, Kweon MH, Yun JM, Adhami VM, Khan N, Syed DN, Mukhtar H. A novel dietary triterpene lupeol induces fas-mediated apoptotic death of androgen-sensitive prostate cancer cells and inhibits tumor growth in a xenograft model. Cancer Res. 2005; 65(23): 11203-11213.
[36] Gallo MBC, Sarachine MJ. Biological activities of lupeol. Int J Biomed Pharm Sci. 2009; 3(1): 46-66.
[37] Saleem M. Lupeol, a novel anti-inflammatory and anti-cancer dietary triterpene. Cancer Lett. 2009; 285(2): 109-115.