Chemical composition and biological activities of essential oil and methanol extract of Scrophularia umbrosa

Document Type: Original paper


1 Drug Applied Research Center, Tabriz University of Medical Sciences, Tabriz, Iran.

2 Biotechnology Research Center, Tabriz University of Medical Sciences, Tabriz, Iran.

3 Drug Applied Research Center, Tabriz University of Medical Sciences, Tabriz, Iran. Faculty of Pharmacy, Tabriz University of Medical Sciences, Tabriz, Iran.

4 Drug Applied Research Center, Tabriz University of Medical Sciences, Tabriz, Iran.Faculty of Pharmacy, Tabriz University of Medical Sciences, Tabriz, Iran.


Background and objectives: Scrophularia umbrosa Dumort is used as a traditional herb in China. In this study, chemical profile, free radical suppression capability, general toxicity and cardiovascular activities of the volatile compounds from S. umbrosa were investigated. Moreover, methanol (MeOH) extract of rhizomes were analyzed to purify and identify the constituents.  Methods: GC/MS was used to identify chemical combination of the volatile oil. Suppression of free radicals of the volatile oil was examined by DPPH method. Also, the essential oil was evaluated for its general toxicity and cardiovascular activity using brine shrimp lethality bioassay and organ bath method, respectively. Preparative HPLC and NMR were applied for investigating the MeOH extract composition.  Results: Forty one Ingredients were recognized, displaying about 93.08 % of the total volatile oil constituents Ketones (38.49%) with hexahydrofarnesyl acetone (26.18%), phytol (11.86%), palmitic acid (8.92%), β-damascenone (4.1%) and copaene (3.82%) were the main components. The essential oil showed weak free radical scavenging activity (RC50=13.71±0.75 mg/mL). Relatively high levels of toxicity were observed with the essential oil of S. umbrosa in comparison with podophyllotoxin. Likewise, the essential oil was able to induced vasorelaxantion in isolated rat aortic rings both in presence and absence of endothelium at a similar rate. An iridoid compounds (sesamoside) was isolated from the MeOH extract of S. umbrosa. Conclusion: Chemical diversity is probably responsible for various pharmacological activities. However, the essential oil of this plant showed toxicity in preliminary toxicity test;  so its toxic effect should be more investigated by various cell lines.


[1] Ardeshirylajimi A, Rezaei-Tavirani M, Mortazavi SA, Barzegar M, Moghadamnia SH, Rezaee MB. Study of anti-cancer property of Scrophularia striata extract on the human astrocytoma cell line (1321). Iran J Pharm Res. 2010; 9(4): 403-410.

[2] Lee GJ, Doh EJ, Lee MY, Ko BS, Oh SE. Discrimination of three Scrophularia plants utilizing ‘Scrophularia Radix’ by DNA markers based on internal transcribed spacer (ITS) sequences. Genes Genome. 2010; 32(2): 181-189.

[3] Hajiaghaee R, Monsef-Esfahani HR, Khorramizadeh MR, Saadat F, Shahverdi AR, Attar F. Inhibitory effect of aerial parts of Scrophularia striata on matrix metalloproteinases expression. Phytother Res. 2007; 21(12): 1127-1129.

[4] Attar F. Notes on the genus Scrophularia L. in Iran. Iran J Botany. 2006; 12(2): 136-143.

[5] Mozaffarian V. The dictionary of Iranian plants. Tehran: Farhang Moasser, 1996.

[6] Azadmehr A, Afshari A, Baradaran B, Hajiaghaee R, Rezazadeh S, Monsef-Esfahani H. Suppression of nitric oxide production in activated murine peritoneal macrophages in vitro and ex vivo by Scrophularia striata ethanolic extract. J Ethnopharmacol. 2009; 124(1): 166-169.

[7] Kim SR, Kim YC. Neuroprotective phenylpropanoid esters of rhamnose isolated from roots of Scrophularia buergeriana. Phytochemistry. 2000; 54(5): 503-509.

[8] Mahboubi M, Kazempour N, Boland Nazar AR. Total phenolic, total flavonoids, antioxidant and antimicrobial activities of Scrophularia striata Boiss. extracts. Jundishapur J Nat Pharm Prod. 2013; 8(1): 15-19.

[9] Williamson EM, Wren RC. Potter's herbal cyclopaedia: the authoratative reference work on plants with a known medical use. 6th ed. Essex: C.W. Daniel Co, 2003.

[10] Pasdaran A, Nahar L, Asnaashari S, Sarker SD, Delazar A. GC-MS Analysis, free radical scavenging and insecticidal activities of essential oil of Scrophularia oxysepala Boiss. Pharm Sci. 2013; 19(1): 1-5.

[11] Mahesh B, Satish S. Antimicrobial activity of some important medicinal plants against plant and human pathogens. World J Agric Sci. 2008; 3(4): 839-843.

[12] Ardeshiry lajimi A, Rezaei Tavirani M, Barzegar M, Moghadamnia SH. Effects of Scrophularia striata extract on human fibroblast cells. Med Sci J Islamic Azad Univ. 2009; 19(3): 168-172.

[13] Zamanian Azodi M, Ardeshiry AR, Ahmadi NA, Rezaee MB, Azizi Jalilian F, Khodarahmi R. Antibacterial effects of Scrophularia striata seed aqueous extract on Staphylococcus aureus. J Paramed Sci. 2013; 4(1): 58-63.

[14] Boros CA, Stermitz FR. Iridoids- An updated review, Part I. J Nat Prod. 1990; 53(5): 1055-1147.

[15] Bhandari SP, Roy A, Agrawal PK. Scrokoelziside A, a triterpene glycoside from Scrophularia koelzii. Phytochemistry. 1996; 41(3): 879-882.

[16] Tasdemir D, Guner ND, Perozzo R, Brun R, Donmez AA. Anti-protozoal and plasmodial FabI enzyme inhibiting metabolites of Scrophularia lepidota roots. Phytochemistry. 2005; 66(3): 355-362.

[17] Monsef-Esfahani HR, Hajiaghaee R, Shahverdi AR. Flavnoids, cininamic acid and phenyl propanoid from aerial parts of Scrophula riastriata. Pharm Biol. 2010; 48(3): 333-336.

[18] Pasdaran A, Delazar A, Nazemiyeh H, Nahar L, Sarker SD. Chemical composition, and antibacterial (aginest Staphylococcus aureus) and free radical scavenging activities of essential oil of Scrophularia amplexicaulis Benth. Rec Nat Prod. 2012; 6(4): 350-355.

[19] Amiri H, Lari Y, Esmaeili A, Samsamnia F, Eghbali D, Viskarami Gh, Dosti B, Noormohamadi E. Essential oil composition and anatomical study of Scrophularia striata Boiss. Iran J Med Aromat Plants. 2011; 27(2): 271-278.

[20] Miyazawa M, Okuno Y. Volatile components from the roots of Scrophularia ningpoensis Hemsl. Flavour Frag J. 2003; 18(5): 398-400.

[21] Adams RP. Identification of essential oil components by gas chromatography/mass spectroscopy. 4rd ed. Carol Stream: Allured Publishing Co, 2007.

[22] NIST 08. Mass spectral library (NIST/EPA/NIH). Gaithersburg: National Institute of Standards and Technology, 2008.

[23] Heshmati Afshar F, Delazar A, Nazemiyeh H, Esnaashari S, Bamdad Moghadam S. Comparison of the total phenol, flavonoid contents and antioxidant activity of methanolic extracts of Artemisia spicigera and A. splendens growing in Iran. Pharm Sci. 2012; 18(3): 165-170.

[24] Takao T, Watanabe N, Yagi I, Sakata K. A simple screening method for antioxidants and isolation of several antioxidants produced by marine bacteria from fish and shellfish. Biosci Biotechnol Biochem. 1994; 58(10): 1780-1783.

[25] Kumarasamy Y, Byres M, Cox PJ, Jaspars M, Nahar L, Sarker SD. Screening seeds of some Scottish plants for free radical scavenging activity. Phytother Res. 2007; 21(7): 615-621.

[26] Meyer BN, Ferringi RN, Putnam JE, Jacobson LB, Nichols DE, McLaughlin JL. Brine shrimp: a convenient bioassay for active plant constituents. Planta Med. 1982; 45(5): 31-34.

[27] Babaei H, Azarmi Y. 17beta-estradiol inhibits calcium-dependent and independent contractions in isolated human saphenous vein. Steroids. 2008; 73(8): 844-850.

[28] Babaei H, Ebrahimi F, Shahbazi Mojarrad J, Azarmi Y, Gharebagheri A. Vasorelaxant effect of a newly synthesized dihydropyridine ethyl ester (DHPEE) on rat thoracic aorta: dual mechanism of action. Adv Pharm Bull. 2011; 1(1): 10-17.

[29] Babaei H, Gharehbagheri A, Eteraf Oskouei T, Delazar A, Asnaashari S, Bamdad Moghadam S. Role of endothelium on vasorelaxant effect of Ribes biebersteinii fruit total extract on rat aorta. Pharm Sci. 2009; 15(2): 159-168.

[30] Chamy MC, Piovano M, Garbarino JA, Gambaro V. Stemodanediterpenoids from Stemodia chilensis. Phytochemistry. 1991; 30(5): 1719-1721.

[31] Hufford CD, Oguntimein BO, Muhammad I. New stemodanediterpenes from Stemodia maritima. J Nat Prod. 1992; 55(1): 48-52.

[32] Allen JG, Colegate SM, Mitchell AA, Mulder RJ, Raisbeck MF. The bioactivity guided isolation and structural identification of toxic cucurbitacin steroidal glucosides from Stemodia kingie. Phytochem Anal. 2006; 17(4): 226-235.

[33] Dantas da Silva LL, Nascimento M, Siqueira Silva DH, Furlan M, da Silva Bolzani V. Antibacterial activity of a stearic acid derivative from Stemodia foliosa. Planta Med. 2002; 68(12): 1137-1139.

[34] Xiao duo J, Quan long P. Studies on the components of the essential oil from Adenosma indianum (Lour.) Merr. Acta Bot Sin. 1985; 27(1): 80-83.

[35] Rastogi RP, Mehrotra BN. Compendium of Indian medicinal plants. New Delhi: Central Drug Research Institute and Publications & Information Directorate, 1998.

[36] Stanner SA, Hughes J, Kelly CN, Buttriss J. A review of the epidemiological evidence for the 'antioxidant hypothesis'. Public Health Nutr. 2004; 7(3): 407-422.

[37] Hennekens CH. Increasing global burden of cardiovascular disease in general populations and patients with schizophrenia. J Clin Psychiatry. 2007; 68(4): 4-7.

[38] Hadi HA, Carr CS, Suwaid AIJ. Endothelial dysfunction: cardiovascular risk factors, therapy, and outcome. Vasc Health Risk Manag. 2005; 1(3): 183-198.

[39] Li W, Sachidanandam K, Ergul A. Comparison of selective versus dual endothelin receptor antagonism on cerebrovascular dysfunction in diabetes. Neurol Res. 2011; 33(2): 185-191.

[40] de Bittencourt Pasquali MA, Roberto de Oliveira M, de Bastiani MA, da Rocha RF, Schnorr CE, Gasparotto J, Gelain DP, Moreira JC. L-NAME cotreatment prevent oxidative damage in the lung of adult Wistar rats treated with vitamin A supplementation. Cell Biochem Funct. 2012; 30(3): 256-263.

[41] Torok J. Histamine-induced relaxation in pulmonary artery of normotensive and hypertensive rats: relative contribution of prostanoids, nitric oxide and hyperpolarization. Physiol Res. 2000; 49(1): 107-114.

[42] Luksha L, Agewall S, Kublickiene K. Endothelium-derived hyperpolarizing factor in vascular physiology and cardiovascular disease. Atherosclerosis. 2009; 202(2): 330-344.

[43] Cao YX, Zhang W, He JY, He LC, Xu CB. Ligustilide induces vasodilatation via inhibiting voltage dependent calcium channel and receptor-mediated Ca2+ influx and release. Vascul Pharmacol.  2006; 45(3): 171-176.

[44] Mauban JR, Remillard CV, Yuan JX. Hypoxic pulmonary vasoconstriction: role of ion channels. J Appl Physiol. 2005; 98(1): 415-420.

[45] Zhang QX, Meng ZQ. The vasodilator mechanism of sulfur dioxide on isolated aortic rings of rats: involvement of the K2+ and Ca2+ channels. Eur J Pharmacol. 2009; 602(1): 117-123.

[46] Kasai R, Katagiri M, Ohtani K, Yamasaki K, Chong Ren Y, Tanaka O. Iridoid glycosides from Phlomis younghusbandii roots. Phytochemistry. 1994; 36(4): 967-970.

[47] Ersoz T, Kaya D, Yalcin FN, Kazaz C, Palaska E, Gotfredsen CH, Jensen SR, Çaliş İ. Iridoid glucosides from Lamium garganicum subsp. laevigatum. Turk J Chem. 2007; 31(2): 155-162.