LC/ESI-MS/MS profiling of Ulmus parvifolia extracts and evaluation of its anti-inflammatory, cytotoxic, and antioxidant activities
-
Suzan A. Mina
,
Farouk R. Melek
Abstract
In this study, a comparative liquid chromatography/mass spectroscopy (LC/ESI-MS/MS) profiling of different fractions of Ulmus parvifolia leaves and stems was performed. Identification of compounds was based on comparing the mass spectrometric information obtained including m/z values and individual compound fragmentation pattern to tandem mass spectral library search and literature data. Eleven compounds were tentatively identified in the different analyzed fractions. One of the major constituents of this plant was isolated and identified as Icariside E4 [dihydro-dehydro-diconiferyl alcohol-4-O-α-L-rhamnopyranoside] (5). The evaluation of anti-inflammatory activity of the total methanolic extract using nitric oxide inhibition on LPS-stimulated RAW 264.7 cells model strong anti-inflammatory activity with 17.5% inhibition of nitric oxide production versus 10% inhibition for dexamethasone. The cytotoxic activity of the methanolic extract and Icariside E4 was evaluated against four types of human cell lines using MTT assay. Icariside E4 showed cytotoxic effect against Hep-G2, MCF-7, and CACO-2 cell lines compared to a negligible activity for the total extract. The same extract showed a moderate antioxidant activity with SC50=362.5 μg/mL.
References
1. Shu Y. ULMUS Linnaeus. Flora China 2003;5:1–10.Search in Google Scholar
2. Wiegree SJ, Sytsma KJ, Guries RP. Phylogeny of elms (Ulmus, Ulmacea). Molecular evidence for sectional classification. Syst Bot 1994;19:590–612.10.2307/2419779Search in Google Scholar
3. Baily LH. The standard cyclopedia of horticulture, revised edition, New York: The Macmillan Company, 1953;2:3408–13.Search in Google Scholar
4. Kwon J, Kim S, Park K, Lee M. Antioxidative and anti-inflammatory effects of phenolic compounds from the roots of Ulmus macrocarpa. Arch Pharm Res 2011;34:1459–66.10.1007/s12272-011-0907-4Search in Google Scholar PubMed
5. Zheng MS, Lee Y, Li Y, Hwangbo K, Lee C, Kim J, et al. Inhibition of DNA topoisomerases I and II and cytotoxicity of compounds from Ulmus davidiana var. japonica. Arch Pharm Res 2010;33:1307–15.10.1007/s12272-010-0903-0Search in Google Scholar PubMed
6. Lee KH, Cho CH, Rhee K. Anti-leukemic and topoisomerase I inhibitory effect of mansonone E isolated from Ulmus davidiana. Med Plant Res 2012;6:4091–95.10.5897/JMPR11.1757Search in Google Scholar
7. Joo T, Sowndhararajan K, Hong S, Lee S, Park S, Kim S, et al. Inhibition of nitric oxide production in LPS-stimulated RAW 264.7 cells by stem bark of Ulmus pumila L. Saudi J Biol Sci 2014;21:427–35.10.1016/j.sjbs.2014.04.003Search in Google Scholar PubMed PubMed Central
8. Wang D, XiA M, Cui Z. New triterpenoids isolated from the root bark of Ulmus pumila L. Chem Pharm Bull 2006;54:775–8.10.1248/cpb.54.775Search in Google Scholar PubMed
9. Kim YO, Seo YC, Lee HY, Oh SM, Lee SW, Kim HD. Anti-wrinkle effect of Ulmus davidiana extracts. Korean J Med Crop Sci 2011;19:508–13.10.7783/KJMCS.2011.19.6.508Search in Google Scholar
10. Lee EB, Kim OK, Jung CS, Jung KH. The influence of methanol extract of Ulmus davidiana var. japonica cortex on gastrice erosion and ulcer and paw edema in rats. J Pharm Soc Korea 1995;39:671–5.Search in Google Scholar
11. Ko JH, Lim KT. Glycoprotein isolated from Ulmus davidiana NAKAI protects against carbon tetrachloride-induced liver injury in the mouse. J Pharmacol Sci 2006;101:205–13.10.1254/jphs.FP0051053Search in Google Scholar
12. Jung H, Kang H, Song YS, Lim C, Park E. Antioxidant and antinociceptive activities of U. davidiana var. japonica. Biomol Ther 2008;16:9–13.10.4062/biomolther.2008.16.1.009Search in Google Scholar
13. Oberacher H, Arnhard K. Compound identification in forensic toxicological analysis with untargeted LC/MS-based techniques. Bioanalysis 2015;7:2825–40.10.4155/bio.15.193Search in Google Scholar PubMed
14. Carmona M, Sánchez AM, Ferreres F, Zalacain A, Barberán FT, Alonso GL. Identification of the flavonoid fraction in saffron spice by LC/DAD/MS/MS: comparative study of samples from different geographical origins. Food Chem 2007;100:445–50.10.1016/j.foodchem.2005.09.065Search in Google Scholar
15. Kim SH, Hwang KT, Park JC. Isolation of flavonoids and determination of rutin from the leaves of Ulums parvifolia. Korean J Pharmacog 1993;23:229–34.Search in Google Scholar
16. Menezes JC, Cavaleiro JA, Kamat SP, Barros CM, Domingues MR. Electrospray tandem mass spectrometry analysis of methylenedioxy chalcones, flavanones and flavones. Rapid Commun Mass Spectrom 2013;27:1303–10.10.1002/rcm.6577Search in Google Scholar
17. Wang B, Liu X, Zhou A, Meng M, Li Q. Simultaneous analysis of coumarin derivatives in extracts of Radix Angelicaepubescentis (Duhuo) by HPLC-DAD-ESI-MSn technique. Anal Meth 2014;6:79–96.10.1039/C4AY01468ESearch in Google Scholar
18. Turetek F, Hanus V. Retro-Diels-Alder reaction in mass spectrometry. Mass Spectrom Rev 1984;3:85–152.10.1002/mas.1280030104Search in Google Scholar
19. Ayatollahia AM, Ghanadianb M, Afsharypourb S, Abdellac OM, Mirzaid M, Askarie G. Pentacyclic triterpenes in Euphorbia microsciadia with their T-cell proliferation activity. Iran J Pharm Res 2011;10:287–94.Search in Google Scholar
20. Hamed MM, El-amine SM, Refahy LA, Soliman EA, Mansour WA, Abu Taleb HM, et al. Anticancer and antiviral estimation of three Ulmus pravifolia extracts and their chemical constituents. Orient J Chem 2015;31:1621–34.10.13005/ojc/310341Search in Google Scholar
21. Mamadalieva NZ, Sharopov F, Girault JP, Wink M, Lafont R. Phytochemical analysis and bioactivity of the aerial parts of Abutilon theophrasti (Malvaceae), a medicinal weed. Nat Prod Res 2014;28:1777–9.10.1080/14786419.2014.939080Search in Google Scholar
22. Takeda Y, Mima C, Masuda T, Hirata E, Takushi A, Otsuka H. Glochidioboside, a glucoside of (7S,8R)-dihydrodehydrodiconiferyl alcohol from leaves of Glochidion obovatum. Phytochemistry 1998;49:2137–39.10.1016/S0031-9422(98)00362-8Search in Google Scholar
23. Baderschneider B, Winterhalter P. Isolation and characterization of novel benzoates, cinnamates, flavonoids, and lignans from Riesling wine and screening for antioxidant activity. J Agr Food Chem 2001;49:2788–98.10.1021/jf010396dSearch in Google Scholar
24. Green LC, Wagner DA, Glogowski J, Skipper PL, Wishnok JK, Tannenbaum SR. Analysis of nitrate, nitrite and 15N in biological fluids. Anal Biochem 1982;126:131–6.10.1016/0003-2697(82)90118-XSearch in Google Scholar
25. Al-Harbi MM, Qureshi S, Ahmed MM, Raza M, Miana GA, Shah AH. Studies on the anti-inflammatory, antipyretic and analgesic activities of santonin. Jpn J Pharmacol 1994;64:135–9.10.1254/jjp.64.135Search in Google Scholar
26. Frémont L. Biological effects of resveratrol. Life Sci 2000;66:663–73.10.1016/S0024-3205(99)00410-5Search in Google Scholar
27. Mosmann T. Rapid colorimetric assays for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Meth 1983;65:55–63.10.1016/0022-1759(83)90303-4Search in Google Scholar
28. Hansen MB, Nielsen SE, Berg K. Re-examination and further development of a precise and rapid dye method for measuring cell growth/cell kill. J Immunol Meth 1989;119:203–10.10.1016/0022-1759(89)90397-9Search in Google Scholar
29. Ratty AK, Sunamoto J, Das NP. Interaction of flavonoids with 1,1-diphenyl-2-picrylhydrazyl free radical, liposomal membranes and soybean lipoxygenase-1. Biochem Pharmacol 1988;37:989–95.10.1016/0006-2952(88)90499-6Search in Google Scholar
Supplemental Material:
The online version of this article (DOI: 10.1515/znc-2016-0057) offers supplementary material, available to authorized users.
©2016 Walter de Gruyter GmbH, Berlin/Boston
Articles in the same Issue
- Frontmatter
- Research Articles
- Seasonal variation of gastroprotective terpenoids in Maytenus robusta (Celastraceae) quantified by gas chromatography-flame ionization detection (GC-FID)
- Plicosepalin A, a new antioxidant catechin–gallic acid derivative of inositol from the mistletoe Plicosepalus curviflorus
- New lupan-type triterpenoids
- Penicilloitins A and B, new antimicrobial fatty acid esters from a marine endophytic Penicillium species
- Anti-acetylcholinesterase activity of essential oils and their major constituents from four Ocimum species
- The chemical composition, antimicrobial, and antioxidant activities of Pycnocycla spinosa and Pycnocyla flabellifolia essential oils
- Biological evaluation and docking studies of some benzoxazole derivatives as inhibitors of acetylcholinesterase and butyrylcholinesterase
- LC/ESI-MS/MS profiling of Ulmus parvifolia extracts and evaluation of its anti-inflammatory, cytotoxic, and antioxidant activities
- Antiproliferative effect of synthetic cyclic imides (methylphtalimides, carboxylic acid phtalimides and itaconimides) against human cancer cell lines
- Anti-inflammatory activity of highly oxygenated terpenoids from Achillea biebersteinii Afan
- Annual Reviewer Acknowledgement
- Reviewer acknowledgement Biosciences – Zeitschrift für Naturforschung C, volume 71 (2016)
Articles in the same Issue
- Frontmatter
- Research Articles
- Seasonal variation of gastroprotective terpenoids in Maytenus robusta (Celastraceae) quantified by gas chromatography-flame ionization detection (GC-FID)
- Plicosepalin A, a new antioxidant catechin–gallic acid derivative of inositol from the mistletoe Plicosepalus curviflorus
- New lupan-type triterpenoids
- Penicilloitins A and B, new antimicrobial fatty acid esters from a marine endophytic Penicillium species
- Anti-acetylcholinesterase activity of essential oils and their major constituents from four Ocimum species
- The chemical composition, antimicrobial, and antioxidant activities of Pycnocycla spinosa and Pycnocyla flabellifolia essential oils
- Biological evaluation and docking studies of some benzoxazole derivatives as inhibitors of acetylcholinesterase and butyrylcholinesterase
- LC/ESI-MS/MS profiling of Ulmus parvifolia extracts and evaluation of its anti-inflammatory, cytotoxic, and antioxidant activities
- Antiproliferative effect of synthetic cyclic imides (methylphtalimides, carboxylic acid phtalimides and itaconimides) against human cancer cell lines
- Anti-inflammatory activity of highly oxygenated terpenoids from Achillea biebersteinii Afan
- Annual Reviewer Acknowledgement
- Reviewer acknowledgement Biosciences – Zeitschrift für Naturforschung C, volume 71 (2016)
