Isolation of Cinnamic Acid Derivatives from the Bulbs of Allium tripedale

Chehri, Zahra; Zolfaghari, Behzad; Dinani, Masoud Sadeghi

Isolation of Cinnamic Acid Derivatives from the Bulbs of Allium tripedale

Document Type : Original Article

Authors

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

Abstract

Background: Allium genus with 750 species is the most diverse genus in the Amaryllidaceae family. Historically, Allium species have been used as medicinal plants, especially for prevention and treatment of cardiovascular diseases and considered as valuable sources of phytonutrients. Phytochemical investigation of Allium tripedale, locally called “Anashq,” which is an edible plant of the “Zagros” region (west of Iran) was conducted in the present study. Materials and Methods: Air-dried bulbs of the plant were extracted in a four-step extraction method with increasing polarity using hexane, chloroform, chloroform–methanol (9:1), and methanol. Chloroform-methanol (9:1) extract was fractionated by medium-pressure liquid chromatography on a RP-18 column using a linear gradient solvent system of H₂O to MeOH. Phenolic-rich fractions were subjected to the final isolation and purification of the constituents by reversed-phase high-performance liquid chromatography method. Structure elucidation of the compounds was performed through comprehensive methods including 1D-and 2D-NMR and mass spectroscopy. Results: Two cinnamic acid derivatives were isolated from the bulbs of A. tripedale; using spectroscopic methods, their chemical structures were determined as 6,7-dimethoxy N-trans-caffeoyltyramine (1) and N-trans-feruloyltyramine (2). Conclusion: Cinnamic acid derivatives are pharmacologically active phenolic compounds, which have been isolated from different Allium species. Isolation of these compounds from A. tripedale is reported for the first time in this study and could be used as a chemical basis for explanation of the plant biological and pharmacological activities.

Keywords

References

1.	Fattorusso E, Iorizzi M, Lanzotti V, Taglialatela-Scafati O. Chemical composition of shallot (Allium ascalonicum hort.). J Agric Food Chem 2002;50:5686-90. [PUBMED]
2.	Zolfaghari B, Barile E, Capasso R, Izzo AA, Sajjadi SE, Lanzotti V, et al. The sapogenin atroviolacegenin and its diglycoside atroviolaceoside from Allium atroviolaceum. J Nat Prod 2006;69:191-5.
3.	Lanzotti V. The analysis of onion and garlic. J Chromatogr A 2006;1112:3-22. [PUBMED]
4.	Kelkar SM, Kaklij GS, Bapat VA. Determination of antidiabetic activity in Allium cepa (onion) tissue cultures. Indian J Biochem Biophys 2001;38:277-9. [PUBMED]
5.	Thomson M, Al-Amin Z, Al-Qattan K, Shaban L, Ali M. Antidiabetic and hypo-lipidemic properties of garlic (Allium sativum) in steretozotocin induced diabetic rats. Int J Diabetes Metab 2007;15:108-15.
6.	Memariani F, Joharchi MR, Khassanov FO. Allium L. Subgen rhizirideumsensulato in Iran, two new records and a synopsis of taxonomy and phytogeography. J Bot 2007;13:12-20.
7.	Friesen N, Fritsch RM, Blattner FR. Phylogeny and new intrageneric classification of Allium (Alliaceae) based on nuclear ribosomal DNA ITS Sequences. Aliso 2006;22:372-95.
8.	Sadeghi M, Zolfaghari B, Senatore M, Lanzotti V. Antifungal cinnamic acid derivatives from Persian leek (Allium ampeloprasum subsp. persicum). Phytochem Lett 2013;6:360-3.
9.	Foti MC, Daquino C, Geraci C. Electron-transfer reaction of cinnamic acids and their methyl esters with the DPPH radical in alcoholic solutions. J Org Chem 2004;69:2309-14. [PUBMED]
10.	Zhang LP, Ji ZZ. Synthesis, antiinflammatory and anticancer activity of cinnamic acids, their derivatives and analogues. Yao Xue Xue Bao 1992;27:817-23. [PUBMED]
11.	Akao Y, Maruyama H, Matsumoto K, Ohguchi K, Nishizawa K, Sakamoto T, et al. Cell growth inhibitory effect of cinnamic acid derivatives from propolis on human tumor cell lines. Biol Pharm Bull 2003;26:1057-9. [PUBMED]
12.	Kusterer J, Keusgen M. Cysteine sulfoxides and volatile sulfur compounds from allium tripedale. J Agric Food Chem 2010;58:1129-37. [PUBMED]
13.	Paydar S, Jelodar GH, Mohammadi J, Mohammadi N. The effect of hydroalcoholic extract of Nectaroscordum tripedaleon liver and kidney functional parameters in streptozocin-induced diabetic male rats. IJEM 2016;18(2):112-9.
14.	Panahi J, Havasian MR, Gheitasi S, Pakzad I, Jaliliyan A, Hoshmandfar R, et al. The in vitro inhibitory effects of the aqueous extracts of summer onion on Candida albicans. SJIMU 2013;21(1):54-9.
15.	He ZD, Qiao CF, Han QB, Cheng CL, Xu HX, Jiang RW, et al. Authentication and quantitative analysis on the chemical profile of Cassia bark (Cortex cinnamomi) by high-pressure liquid chromatography. J Agric Food Chem 2005;53:2424-8. [PUBMED]
16.	Wen D, Li C, Di H, Liao Y, Liu H. A universal HPLC method for the determination of phenolic acids in compound herbal medicines. J Agric Food Chem 2005;53:6624-9. [PUBMED]
17.	Nishioka T, Watanabe J, Kawabata J, Niki R. Isolation and activity of N-p-coumaroyltyramine, an α-glucosidase inhibitor in welsh onion (Allium fistulosum). Biosci Biotechnol Biochem 1997;61:1138-41.
18.	Park JB. Isolation and characterization of N-feruloyltyramine as the P-selectin expression suppressor from garlic (Allium sativum). J Agric Food Chem 2009;57:8868-72. [PUBMED]
19.	Barile E, Bonanomi G, Antignani V, Zolfaghari B, Sajjadi SE, Scala F, et al. Saponins from Allium minutiflorum with antifungal activity. Phytochemistry 2007;68:596-603. [PUBMED]
20.	Fattorusso E, Lanzotti V, Taglialatela-Scafati, O. Antifungal N-feruloyl amides from roots of Allium species. Plant Biosyst 1999;133:199-203.
21.	Park JB, Schoene N. Clovamide-type phenylpropenoic acid amides, N-coumaroyldopamine and N-caffeoyldopamine, inhibit platelet-leukocyte interactions via suppressing P-selectin expression. J Pharmacol Exp Ther 2006;317:813-9. [PUBMED]
22.	Park JB. Quantitation of clovamide-type phenylpropenoic acid amides in cells and plasma using high-performance liquid chromatography with a colorimetric electrochemical detector. J Agric Food Chem 2005;19:8135-40.
23.	Ko HJ, Ahn EK, Oh JS. N-trans-ρ-caffeoyl tyramine isolated from Tribulus terrestris exerts anti-inflammatory effects in lipopolysaccharide-stimulated RAW 264.7 cells. Int J Mol Med 2015;36:1042-8. [PUBMED]
24.	Park JB, Schoene N. N-caffeoyltyramine arrests growth of U937 and Jurkat cells by inhibiting protein tyrosine phosphorylation and inducing caspase-3. Cancer Lett 2003;202:161-71. [PUBMED]

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