Isolation and characterization of methylated flavones from Artemisia kermanensis

Yazdiniapour, Zeinab; Yegdaneh, Afsaneh; Akbari, Soudeh

Isolation and characterization of methylated flavones from Artemisia kermanensis

Authors

Department of Pharmacognosy, Isfahan University of Medical Sciences, Isfahan, Iran

Abstract

Background: Artemisia kermanensis Podl. is a green aromatic perennial shrub that belongs to the family Asteraceae and it grows widely in central deserts and south-eastern mountains of Iran such as Taftan Mountain in Sistan and Baluchestan Province. Artemisia species have been used traditionally as a remedy for various feverous diseases, including malaria, treatment of colds, infections, parasites, inflammations of the liver, as well as dyspepsia, diabetes, hypertension, and so many other conditions. Materials and Methods: Air-dried A. kermanensis extraction from all parts of the plant was done using different organic solvents. The methanolic extract was selected for isolation of flavonoids, using thin-layer chromatography. The chemical structures of the isolated compounds were determined based on analysis of mass and nuclear magnetic resonance spectra. Results: Two flavone aglycones were isolated and identified for the first time from this plant's methanolic extract, including 5,7-dihydroxy-3',4',6-trimethoxyflavone (eupatilin) and 5,7,3'-Trihydroxy-6,4',5'-trimethoxyflavone. Conclusions: Eupatilin is known for its anticancer, antioxidant, and anti-inflammatory activities. In future researches on A. kermanensis, as a rich source of these flavone compounds, it is wise to investigate for the proven eupatilin's biological activities that have been mentioned

Keywords

References

1.	Kazemi M, Dakhili M, Dadkhah A, Yasrebifar Z, Larijani K. J Med Plant Res 2011;5:18:4481-86.
2.	Patil G, Dass S, Chandra RJ. Artemisia afra and modern diseases. J Pharmacogenomics Pharmacoproteomics 2011;2:1-22.
3.	Suresh J, Reddy V, Rajan D, Ihsanullah M, Khan MJ. Antimicrobial activity of Artemisia abrotanum and Artemisia pallens. J Pharmacogn Phytochem Res 2010;3:18-21.
4.	Abad MJ, Bedoya LM, Apaza L, Bermejo P. The Artemisia L. genus: A review of bioactive essential oils. J Mol 2012;17:2542-66.
5.	Mighri H, Hajlaoui H, Akrout A, Najjaa H, Neffati M. Antimicrobial and antioxidant activities of Artemisia herba-alba essential oil cultivated in Tunisian arid zone. J C R Chim 2010;13:380-6.
6.	Grech-Baran M, Pietrosiuk A. Artemisia species in vitro cultures for production of biologically active secondary metabolites. BioTechnologia 2012;93:371-80.
7.	Ferreira JF, Luthria DL, Sasaki T, Heyerick A. Flavonoids from Artemisia annua L. as antioxidants and their potential synergism with artemisinin against malaria and cancer. Molecules 2010;15:3135-70.
8.	Lone SH, Bhat KA, Khuroo MA. Arglabin: From isolation to antitumor evaluation. Chem Biol Interact 2015;240:180-98.
9.	Koul B, Taak P, Kumar A. The Artemisia genus: A review on traditional uses, phytochemical constituents, pharmacological properties and germplasm conservation. J Glycomics Lipidomics 2017;7 (1):142.
10.	Brown GD, Liang GY, Sy LK. Terpenoids from the seeds of Artemisia annua. Phytochemistry 2003;64:303-23.
11.	Lee JY, Chang EJ, Kim HJ, Park JH, Choi SW. Antioxidative flavonoids from leaves of carthamus tinctorius. Arch Pharm Res 2002;25:313.
12.	Kim AR, Ko HJ, Chowdhury MA, Chang YS, Woo ER. Chemical constituents on the aerial parts of Artemisia selengensis and their IL-6 inhibitory activity. Arch Pharm Res 2015;38:1059-65.
13.	Mabry TJ, Markham KR, Thomas MB. The Systematic Identification of Flavonoids. New York etc., Springer. 1970.
14.	Liu YL, Mabry T. Flavonoids from Artemisia ludoviciana var. ludoviciana. Phytochemistry 1982;21:209-14.
15.	Liu YL, Mabry T. Two methylated flavones from Artemisia frigida. Phytochemistry 1981;20:309-11.
16.	Bora KS, Sharma A. The genus Artemisia: A comprehensive review. Pharm Biol 2011;49:101-9.
17.	Son JE, Lee E, Seo SG, Lee J, Kim JE, Kim J, et al. Eupatilin, a major flavonoid of Artemisia, attenuates aortic smooth muscle cell proliferation and migration by inhibiting PI3K, MKK3/6, and MKK4 activities. Planta Med 2013;79:1009-16.
18.	Yuan H, Lu X, Ma Q, Li D, Xu G, Piao G. Flavonoids from Artemisia sacrorum Ledeb. and their cytotoxic activities against human cancer cell lines. Exp Ther Med 2016;12:1873-8.
19.	Naqinezhad A, Nabavi SM, Nabavi SF, Ebrahimzadeh MA. Antioxidant and antihemolytic activities of flavonoid rich fractions of Artemisia tschernieviana Besser. Eur Rev Med Pharmacol Sci 2012;16 Suppl 3:88-94.
20.	Lee SJ, Chung HY, Maier CG, Wood AR, Dixon RA, Mabry TJ. Estrogenic flavonoids from Artemisia vulgaris L. J Agric Food Chem 1998;46:3325-9.
21.	Kim JS, Lee SG, Min K, Kwon TK, Kim HJ, Nam JO. Eupatilin inhibits adipogenesis through suppression of PPARγ activity in 3T3-L1 cells. Biomed Pharmacother 2018;103:135-9.
22.	Lee JY, Bae H, Yang C, Park S, Youn BS, Kim HS, et al. Eupatilin promotes cell death by calcium influx through ER-mitochondria axis with SERPINB11 inhibition in epithelial ovarian cancer. Cancers (Basel) 2020;12 (6):1459.
23.	Zhong WF, Wang XH, Pan B, Li F, Kuang L, Su ZX. Eupatilin induces human renal cancer cell apoptosis via ROS-mediated MAPK and PI3K/AKT signaling pathways. Oncol Lett 2016;12:2894-9.
24.	Wang X, Zhu Y, Zhu L, Chen X, Xu Y, Zhao Y, et al. Eupatilin inhibits the proliferation of human esophageal cancer TE1 cells by targeting the Akt-GSK3 β and MAPK/ERK signaling cascades. Oncol Rep 2018;39:2942-50.
25.	Li YY, Wu H, Dong YG, Lin BO, Xu G, Ma YB. Application of eupatilin in the treatment of osteosarcoma. Oncol Lett 2015;10:2505-10.
26.	Kim J, Kim Y, Yi H, Jung H, Rim YA, Park N, et al. Eupatilin ameliorates collagen induced arthritis. J Korean Med Sci 2015;30:233-9.
27.	Liu H, Hao J, Wu C, Liu G, Wang X, Yu J, et al. Eupatilin Alleviates lipopolysaccharide-induced acute lung injury by inhibiting inflammation and oxidative stress. Med Sci Monit 2019;25:8289-96.
28.	Du L, Chen J, Xing YQ. Eupatilin prevents H₂O₂-induced oxidative stress and apoptosis in human retinal pigment epithelial cells. Biomed Pharmacother 2017;85:136-40.
29.	Nageen B, Sarfraz I, Rasul A, Hussain G, Rukhsar F, Irshad S, et al. Eupatilin: A natural pharmacologically active flavone compound with its wide range applications. J Asian Nat Prod Res 2020;22:1-6.
30.	Song EH, Chung KS, Kang YM, Lee JH, Lee M, An HJ. Eupatilin suppresses the allergic inflammatory response in vitro and in vivo. Phytomedicine 2018;42:1-8.

Advanced Biomedical Research