IDENTIFICATION OF CYTOTOXIC AND ANTIOXIDANT COMPOUNDS FROM ALLIUM GRAMINEUM FLOWERS

Authors

  • Lasha Mskhiladze Department of Pharmacognosy and Botany, Faculty of Pharmacy, Tbilisi State Medical, University, 33, Vazha Pshavela Ave., Tbilisi, 0177, Georgia
  • David Chincharadze Department of Pharmacognosy and Botany, Faculty of Pharmacy, Tbilisi State Medical, University, 33, Vazha Pshavela Ave., Tbilisi, 0177, Georgia
  • Monique Tits Laboratory of Pharmacognosy, Department of Pharmacy, Centre Interdisciplinaire de, Recherche du Médicament-CIRM, University of Liège, CHU-B36, B-4000 Liège, Belgium
  • Jean- Noël Wauters Laboratory of Pharmacognosy, Department of Pharmacy, Centre Interdisciplinaire de, Recherche du Médicament-CIRM, University of Liège, CHU-B36, B-4000 Liège, Belgium
  • Akeila Bellahcène Metastasis Research Laboratory, University of Liège, GIGA-R, University of Liège, CHU-B36, B-4000 Liège, Belgium
  • Vincent Castronovo Metastasis Research Laboratory, University of Liège, GIGA-R, University of Liège, CHU-B36, B-4000 Liège, Belgium
  • Ange Mouithys- Mickalad Centre for Oxygen Research and Development (CORD), Institute of Chemistry B6a,University of Liège, Sart Tilman, 4000 Liège 1, Belgium
  • Thierry Franck Centre for Oxygen Research and Development (CORD), Institute of Chemistry B6a,University of Liège, Sart Tilman, 4000 Liège 1, Belgium
  • Michel Frédérich Laboratory of Pharmacognosy, Department of Pharmacy, Centre Interdisciplinaire de, Recherche du Médicament-CIRM, University of Liège, CHU-B36, B-4000 Liège, Belgium

Abstract

The present study evaluates the in vitro anticancer, antiplasmodial and antioxidant activity of the ethanolic crude extract from the flowers of Allium gramineum growing in Georgia and of one flavonol and two steroidal glycosides which were isolated from this plant. The flowers were extracted with ethanol and this total extract was subjected to successive bioguided fractionations to provide glycosides 1-3. Their structures were elucidated on the basis of NMR and ESI-MS spectrometric data in comparison with the existing literature and have been identified as: isorhamnetin-3-O-β-D-glucopyranoside (1), diosgenin-3-O-α-rhamnopyranosyl-(1→2)-β-D-glucopyranoside (Prosapogenin A of dioscin) (2), diosgenin-3-O-α-rhamnopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→4)-]-β-D-glucopyranoside (Deltonine) (3). The ethanolic extract has been shown to strongly inhibit the growth of breast adenocarcinoma cell lines, with an IC50 of 4.5 ± 0.7μg/mL for MDAMB-231 and 4.8 ± 0.9μg/mL for MCF-7 cells. The cytotoxic activity was related to 2 and 3 which exhibited potent cytotoxicity, with an IC50 of ± 3μM. Concerning antiplasmodial activities, only weak activities were observed using the ethanolic extract and the two saponins. The flavonoid was almost inactive. Finally, the radical-scavenging activity of the ethanolic extract was tested in presence of ABTS•+ solution. A decrease of the absorbance intensity was observed, with an IC50 value of 22.1 ± 0.6μg/mLwhile trolox, used as Standard drug, showed a pronounced activity (IC50 = 12.7±0.5μM). The glycoside 1 showed the lowest IC50 value of 20.1 ± 0.8μM while both 2 and 3 exhibited very weak radical scavenging activity.

Keywords:

Allium gramineum, Alliaceae, Steroidal saponine, Flavonoid, Structure determination, pharmacological activities

DOI

https://doi.org/10.25004/IJPSDR.2015.070114

References

1. Gagnidze R. Vascular Plants of Georgia a Nomenclatural Checklist. Tbilisi, Republic of Georgia: Ketskhoveli, N. Ed. Institute of Botany, 2005.
2. Lanzotti V, Scala F, Bonanomi G. Compounds from Allium species with cytotoxic and antimicrobial activity. Phytochem Reviews. 2014; 13: 769-791.
3. Lanzotti V. The analysis of onion and garlic. J. Chromatogr. A. 2006; 1112, 3-22.
4. Amin M, Kapadnis B. Heat stable antimicrobial activity of Allium ascalonicum against bacteria and fungi. Indian J. Exp. Biol. 2005; 43, 751-754.
5. Barile E, Bonanomi G, Antignani V, Zolfaghari B, Sajjadi S, Scala F, Lanzotti, V. Saponins from Allium minutiflorum with antifungal activity. Phytochemistry 2007; 68, 596-603.
6. Demirtas I, Erenler R, Elmastas M, Goktasoglu A. Studies on the antioxidant potential of flavones of Allium vineale isolated from its water-soluble fraction. Food Chemistry 2013; 136: 34–40.
7. Zolfaghari B, Sadegui M, Troiano R, Lanzotti V. Vavilosides A1/A2-B1/B2, new furostane glycosides from the bulbs of Allium vavilovii with cytotoxic activity. Bioorganic & Medicinal Chemistry 2013; 21: 1905-1910.
8. Nyanhanda T, Gould EM, Hurst RD. Plant-derived foods for the attenuation of allergic airway inflammation. Curr Pharm Des. 2014; 20 (6): 869-78.
9. Madhu C, Upendra S, Neeraj K, Bikram S, Satwinderjeek K. Antioxidant activity and identification of bioactive compounds from leaves of Anthocephalus cadamba by ultra-performance liquid chromatography/electrospray ionization quadrupole time of flight mass spectrometry. Asian Pacific Journal of Tropical Medicine 2012; 5: 997-985
10. Bagrationi, D. Iadigar Daudi. Edition of Tbilisi University: Republic of Georgia, 1993.
11. Mskhiladze L, Legault J, Lavoie S, Mshvildadze V, Kuchukhidze J, Elias R, Pichette A. Cytotoxic steroidal saponins from the flowers of Allium leucanthum. J. Molecules 2008; 13: 2925-2934.
12. Mskhiladze L, Kutchukhidze J, Chincharadze D, Delmas F, Elias R, Favel A. In vitro antifungal and antileishmanial activities of steroidal saponins from Allium leucanthum C. Koch a Caucasian endemic species. Georgian Medical News 2008; 1(154): 39-43.
13. D’Agostino M, De Simone F, Dini A, Ramundo E, Zollo F. Flavonol glycosides from Eupatorium tinifolium. Phytochemistry 1990; 29: 353-354.
14. Jianming J, Xikui L, Rongwei T, Chongren Y. Enzymatic degradation of Parvifloside. Acta botanica sinica. 2002; 44: 1243-1249.
15. Agrawal K, Jain C, Gupta K, Thakur S. Carbon-13 NMR spectroscopy of steroidal sapogenins and steroidal saponins. Phytochemistry 1985; 24: 2479-2496.
16. Frederich M, De Pauw MC, Prosperi C, Tits M, Brandt V, Penelle J, Hayette MP, DeMol P, Angenot L. Strychnogucines A and B, two new antiplasmodial bisindole alkaloids from Strychnos icaja. J. Nat. Prod. 2001; 64: 12-16.
17. Jonville C, Kodja H, Humeau L, Fournel J, De Mol P, Cao M, Angenot L, Frederich M. Screening of medicinal plants from Reunion Island for antimalarial and cytotoxic activity. J Ethnopharmacol. 2008; 120: 382-386.
18. Re R, Pellegrini N, Proteggente A, Pannala A, Yang M, Rice-Evans C. Antioxidant activity applying an improved ABTS radical cation decolorization assay. Free Radical Biology & Medicine 1999; 26: 1231-1237.
19. Timité G, Mitaine-Offer C, Miyamoto T, Tanaka C, Mirjolet F, Duchamp O, Lacaille-Dubois A. Structure and cytotoxicity of steroidal glycosides from Allium shoenoprasum. Phytochemistry 2013; 88: 61-66.
20. Sautour M, Mitaine-Offer A, Lacaille-Dubois M. The Dioscorea genus: areview of bioactive steroid sponins. J Nat Med. 2007; 61: 91-101.
21. Rezgui A, Mitain-Offer AC, Paululat T, Delemasure S, Dutartre P, Lacaille-Dubois MA. Cytotoxic steroidal glycosides from Allium flavum. Fitoterapia 2014; 93: 121-125.

Published

01-01-2015
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How to Cite

“IDENTIFICATION OF CYTOTOXIC AND ANTIOXIDANT COMPOUNDS FROM ALLIUM GRAMINEUM FLOWERS”. International Journal of Pharmaceutical Sciences and Drug Research, vol. 7, no. 1, Jan. 2015, pp. 78-82, https://doi.org/10.25004/IJPSDR.2015.070114.

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Research Article

How to Cite

“IDENTIFICATION OF CYTOTOXIC AND ANTIOXIDANT COMPOUNDS FROM ALLIUM GRAMINEUM FLOWERS”. International Journal of Pharmaceutical Sciences and Drug Research, vol. 7, no. 1, Jan. 2015, pp. 78-82, https://doi.org/10.25004/IJPSDR.2015.070114.

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