Phytochemistry and antioxidant activity of Lallemantia iberica aerial parts

Authors

1 Department of Pharmacognosy, Faculty of Pharmacy, Alborz University of Medical Sciences, Karaj, Iran.

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

3 Department of Medicinal Chemistry, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran.

4 Institute of Medicinal Plants, Iranian Academic Center for Education, Culture & Research (ACECR),Karaj, Iran.

5 Department of Pharmacognosy, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran.

Abstract

Background and objectives:Lallemantia iberica (Lamiaceae) is a medicinal plant distributed in different parts of Iran. This research, has evaluated the phytochemical constituents and antioxidant activity of the aerial parts of the plant.
Methods: Different chromatographic methods such as column chromatographies using Silica gel (normal and reversed phases), Sephadex LH-20 and HPLC were used for isolation of the compounds from the ethyl acetate and methanol extract of L. iberica aerial parts. The structures of the isolated compounds were elucidated using 1H-NMR, 13C-NMR and EI-MS. Antioxidant activity of the extracts were also evaluated in DPPH and FRAP tests.
Results: Two sterols,β-sitosterol acetate (1), β-sitosterol (2), one triterpenoic acid,ursolic acid (3), one polyphenol, rosmarinic acid (4) and six flavonoides,Luteolin-7-O-glucoside (5), 4'-methoxy-luteolin-7-O-glucoside (6), apigenin-7-O-glucoside (7), Luteolin (8),  diosmetin (9), apigenin (10) were isolated and identified from the ethyl acetate and methanol extracts. The antioxidant activity of the ethyl acetate (IC50 189.95±2.8 μg/mL) and the methanol extracts (IC50 140±1.2 μg/mL) were compared to the standard antioxidant, BHA (IC50 100±1.6 μg/mL) in DPPH method. The reducing power of the ethyl acetate (300.28 μmol Eq FeSO4.7H2O/mg DW), the methanol extract (553.14 μmol Eq FeSO4.7H2O/mg DW) and BHA (558.36 μmol Eq FeSO4.7H2O/mg of standard) were elucidated in FRAP assay.
Conclusion: The results introduce L. iberica as a medicinal plant with valuable constituents which are responsible of different pharmacological activities.

Keywords


[1] Naghibi F, Mosadegh M, Mohammadi Motamed S,  Ghorbani A. Labiatae family in folk medicine in Iran: from ethnobotany to pharmacology. Iran J Pharm Res. 2005; 4(2): 63-79.
[2] Zargari A. Medicinal plants. Tehran: Tehran University Publications, 1990.
[3] Ghahraman A. Plant systematic. Tehran: Tehran University Publications, 1994.
[4] Mozaffarian V. A dictionary of Iranian plant names. Tehran: Farhange Moaser, 1996.
[5] Amin Gh. Popular medicinal plants of Iran. Tehran: Ministry of Health Publications, 1991.
[6] Amanzadeh Y, Khosravi Dehaghi N, Gohari AR, Monsef-Esfahani  HR, Sadat Ebrahimi SE. Antioxidant activity of essential oil of Lallemantia iberica in flowering stage and post-flowering stage. Res J Biol Sci. 2011; 6(3): 114-117.
[7] Semnani MK. Essential oil composition of Lallemantia iberica Fisch. et CA Mey. J Essent Oil Res. 2006; 18(2): 164-165.
[8] Khosravi Dehaghi N, Daowan L, Amanzadeh Y, Sadat-Ebrahimi SS, Proksch P. A new putrescine bisamide phenolic glycoside from the seeds of Lallemantia iberica (M. Bieb.) Fisch. & C. A. Mey. Phytochem Lett. 2012; 5(3): 643-646.
[9] MacDonald-Wicks LK, Wood LG, Garg ML. Methodology for the determination of biological antioxidant capacity in vitro: a review. J Sci Food Agric. 2006; 86(13): 2046-2056.
[10] Sarker SD, Latif Z, Gray AI. Natural products isolation. New Jersey: Humana Press Inc, 2005.
[11] Tofighi Z, Alipour F, Yassa N, Hadjiakhoondi A, Hadavinia H, Goodarzy S, Golestani R. Chemical composition and antioxidant activity of Otostegia persica essential oil from Iran. Int J Essent Oil Ther. 2009; 3: 45-48.
[12] Benzie IF, Strain J. The ferric reducing ability of plasma (FRAP) as a measure of “antioxidant power”: the FRAP assay. Anal Biochem. 1996; 239(1): 70-76.
[13] Heinonen M, Lehtonen P, Hopia A. Antioxidative activity of berry and fruit wines and liquor. J Agr Food Chem. 1998; 46(1): 25-31.
[14] Huang D, Ou B, Prior RL. The chemistry behind antioxidant capacity assays. J Agr Food   Chem. 2005; 53(6): 1841-1856.
[15] Yassa N, Saeidnia S, Pirouzi R, Akbaripour M, Shafiee A. Three phenolic glycosides and immunological properties of Achillea millefolium from Iran, population of Golestan. Daru J Pharm Sci. 2007; 15(1): 49-52.
[16] Chiruvella KK, Mohammed A, Dampuri G, Gopal Ghanta R, Raghavan SC. Phytochemical and antimicrobial studies of methyl angolensate and luteolin-7-O-glucoside isolated from callus cultures of Soymida febrifuga. Int J Biol Sci. 2007; 3(4): 269-278.
[17] Agrawal PK. Carbon-13 NMR of flavanoids. Amsterdam: Elsevier Science Publishers, 1989.
[18] Hassan Wafaa HB, Al Youssef Hanan M, Al Shammari L, Abdolah Rehab H. New pentacyclic triterpene ester and flavone glycoside from the biologically active extract of Carduus pysnocephalus.  J Pharmacognosy Phytotherapy. 2015; 7(4): 45-55.
[19] Seebacher W, Simic N, Weis R, Saf  R, Kunert O. Complete assignments of 1H and 13C NMR resonances of oleanolic acid, 18 -oleanolic acid, ursolic acid and their 11-oxo derivatives. Magn Reson Chem. 2003; 41(8): 636-638.
[20] Özgen U, Mavi A, Terzi Z, Kazaz C, Asçı A, Kaya Y, Seçen H. Relationship between chemical structure and antioxidant activity of luteolin and its glycosides isolated from Thymus sipyleus subsp sipyleus var sipyleus. Rec Nat Prod. 2011; 5(1): 12-21.
[21] Gu H, Chen R, Sun Y, Liu F. Studies on chemical constituents from herb of Dracocephalum moldavica. Zhongguo Zhong Yao Za Zhi. 2004; 29(3): 232-234.
[22] Saeidnia S, Permeh P, Gohari AR, Mashinchian-Moradi A. Gracilariopsis persica from Persian Gulf contains bioactive sterols. Iran J Pharm Res. 2012; 11(3): 845-849.
[23] Gohari AR, Saeidnia S, Shahverdi AR, Yassa N, Malmir M, Mollazade K, Naghinejad AR. Phytochemistry and antimicrobial compounds of Hymenocrater calycinus. Eurasian J Biosci. 2009; 3(9): 64-68.
[24] Ghannadi A, Movahedian A, Jannesary Z. Hypocholesterolemic effects of Balangu (Lallemantia royleana) seeds in the rabbits fed on a cholesterol-containing diet. Avicenna J Phytomed. 2015; 5(3): 167-173.
[25] Sharifi-Rad J, Hoseini-Alfatemi SM, Sharifi-Rad M, Setzer WN. Chemical composition, antifungal and antibacterial activities of essential oil from Lallemantia Royleana (Benth. in Wall.) Benth. J Food Safety. 2014; 35(1): 19-25.
[26] Golshani Y, Mohammadi S. Evaluation of antinociceptive effect of methanolic extract of Lallemantia iberica in adult male rats. Armaghan Danesh.2015; 19(12): 1058-1068.
[27] Berges  RR, Windeler J, Trampisch  HJ, Senge T. Randomised, placebo-controlled, double-blind clinical trial of beta-sitosterol in patients with benign prostatic hyperplasia. Lancet. 1995; 345(8964): 1529-1532.
[28] Awad A, Barta SL, Fink CS, Bradford PG. β-sitosterol enhances tamoxifen effectiveness on breast cancer cells by affecting ceramide metabolism. Mol Nutr Food Res. 2008; 52(4): 419-426.
[29] Liu J. Pharmacology of oleanolic acid and ursolic acid. J Ethnopharmacol. 1995; 49(2): 57-68.
[30] Novotny L, Vachalkova A, Biggs D. Ursolic acid: an anti-tumorigenic and chemopreventive activity minireview. Neoplasma. 2001; 48(4): 241-246.
[31] Giovana DG, Edna S, Milene B, Joice L, Patrícia P, Patrícia A. Effect of rosmarinic and caffeic acids on inflammatory and nociception process in rats. ISRN Pharmacol. 2011; Article ID 451682.
[32] Cushnie  TPT, Lamb  AJ. Antimicrobial activity of flavonoids. Int J Antimicrob Ag. 2005; 26(5): 343-356.
[33] Hui L, Hong-Bo L, Ming Z, Fang Y, Zhong-Xian Z, Zhi-Lan L. Effect of apigenin on the reproductive system in male mice. Health. 2010; 2(5): 435-440.