Alkaloid profiling of Galanthus woronowii Losinsk. by GC-MS and evaluation of its biological activity

Abstract

The alkaloid profiles of the aerial parts and the bulbs of

Galanthus woronowii Losinsk. were analyzed by means of Gas

Chromatography-Mass Spectrometry (GC-MS). Totally, twentyeight

compounds were detected. Galanthamine and galanthine

were found to be the main alkaloids both in the extracts of the

aerial parts and the bulbs. Most of the identified compounds

were lycorine and galanthamine-type Amaryllidaceae alkaloids.

In addition, the acetylcholinesterase (AChE) inhibitor potentials

of the extracts prepared from the aerial parts and bulbs were

determined by in vitro Ellman’s method and both of the extracts

were found to exhibit significant activity (aerial parts: IC50=

0.027 μg/mL and bulbs: IC50= 0.084 μg/mL).

Keywords

• Galanthus woronowii; Amaryllidaceae; GC-MS; alkaloids.

References

1. 1. Davis AP. The Genus Galanthus. Editor: Mathew B. Timber Pres Inc., Oregon. 1999. 2. Davis AP. The Genus Galanthus-snowdrops in the wild. In: Snowdrops, A Monograph of Cultivated Galanthus. Editors: Bishop M, Davis AP, Grimshaw J. Griffin Press Publishing Ltd, Cheltenham. 2006, pp. 9–63. 3. Ünver N. New skeletons and new concepts in Amaryllidaceae alkaloids. Phytochem Rev 2007; 6: 125-35. 4. Berkov S, Codina C, Bastida J. The Genus Galanthus: A Source of Bioactive Compounds. In: Phytochemicals - A Global Perspective of Their Role in Nutrition and Health. Editor: Rao V. InTech. 2012, pp. 235-254. 5. Yakovleva A. Alkaloids of Galanthus woronovii. VI Isolation of tazettine. Zhurnal Obshchei Khimii 1963; 33: 1691–3. 6. Kintsurashvili L, Vachnadze V. Plants of the Amaryllidaceae family grown and introduced in Georgia: A source of galanthamine. Pharm Chem 2007; 41: 492-4. 7. Bozkurt-Sarıkaya B, Kaya Gİ, Önür MA, Bastida J, Ünver- Somer N. Phytochemical investigation of Galanthus woronowii. Biochem Syst Ecol 2013; 51: 276-9. 8. Ellman L, Courtney KD, Andres VJr, Featherstone RM. New and rapid colorimetric determination of acetylcholinesterase activity. Biochem. Pharmacol 1961; 7: 88–95. 9. Bozkurt-Sarıkaya B, Ünver-Somer N, Kaya Gİ, Önür MA, Bastida J, Berkov S. GC-MS investigation and acetylcholinesterase inhibitory activity Galanthus rizehensis. Z. Naturforsch 2013; 68c: 118-24. 10. Lόpez S, Bastida J, Viladomat F, Codina C. Acetylcholinesterase inhibitory activity of some Amaryllidaceae alkaloids and Narcissus extracts. Life Sci 2002; 71: 2521–9. 11. Bastida J, Lavilla R, Viladomat F. Chemical and biological aspects of Narcissus alkaloids. In: The Alkaloids chemistry and biology. Editor: Cordell GA. Elsevier Inc, San Diago. 2006, 63: pp. 87–179. 12. Çitoğlu G, Acıkara OB, Yılmaz BS, Özbek H. Evaluation of analgesic, anti-inflammatory and hepatoprotective effects of lycorine from Sternbergia fisheriana (Herbert) Rupr. Fitoterapia 2012; 83: 81–7. 13. Şenel G, Özkan M, Kandemir N. A karyological investigation on some rare and endangered species of Amaryllidaceae in Turkey. Pak J Bot 2002; 34: 229-35. 14. Zeybek N. Taxonomical investigations on Turkish snowdrops (Galanthus L.). Turk J Botany 1988;12: 89-103. 15. Zeybek N, Sauer E. Turkish Snowdrops I (Beitrag zur Kenntnis der Türkischen Schneeglöckhen)(Galanthus L.) I. Ornamental Plants. Agriculture and Industry Press, Izmir. 1994. 16. Emir A, Çiçek Polat D, Kaya Gİ, Sarıkaya B, Önür MA, Unver Somer N. Simultaneous Determination of Lycorine and Galanthamine in Galanthus woronowii by HPLC-DAD. Acta Chromatogr 2013;25: 755-64. 17. Berkov S, Bastida J, Nikolova M, Viladomat F, Codina C. Rapid TLC/GC-MS identification of acetylcholinesterase inhibitors in alkaloid extracts. Phytochemistry Anal 2008; 19: 411–9. 18. Berkov S, Bastida J, Sidjimova B, Viladomat F, Codina C. Phytochemical differentiation of Galanthus nivalis and Galanthus elwesii (Amaryllidaceae): A case study. Biochem Syst Ecol 2008; 36: 638–45. 19. Viladomat F, Bastida J, Tribo G, Codina C, Rubiralta M. Alkaloids from Narcissus bicolor. Phytochemistry 1990; 29: 1307-10. 20. Berkov S, Bastida J, Viladomat F. Codina C. Analysis of galanthamine type- alkaloids by capillary gas chromatographymass spectrometry in plants. Phytochemistry Anal 2008; 19: 285–93. 21. Berkov S, Evstatieva L, Popov S. Alkaloids in Bulgarian Pancratium maritimum L. Z. Naturforsch 2004; 59c: 65–9. 22. Berkov S, Pavlov A, Ilieva M, Burrus M, Popov S. Stanilova M. CGC-MS of alkaloids in Leucojum aestivum plants and their in vitro cultures. Phytochemistry Anal 2005; 16: 98–103. 23. Kreh M, Matusch R, Witte L. Acetylated alkaloids from Narcissus pseudonarcissus. Phytochemistry 1995; 40: 1303-6. 24. Berkov S, Bastida J, Tsvetkova R, Viladomat F. Alkaloids from Sternbergia colchiciflora. Z. Naturforsch 2009; 64c: 311-6. 25. Evidente A, Iasiello I, Randazzo G. Isolation of sternbergine, a new alkaloid from bulbs of Sternbergia lutea. J Nat Prod 1984; 47: 1003–8. 26. Cedron JC, Gutiérrez D, Flores N, Ravelo AG, Estevez- Braun A. Synthesis and antiplasmodial activity of lycorine derivatives. Bioorg Med Chem 2010; 18: 4694-4701. 27. Toriizuka Y, Kinoshita E, Kogure N, Kitajima M, Ishiyama A, Otoguro K, Yamada H, Omura S, Takayama H. New lycorine-type alkaloid from Lycoris traubii and evaluation of antitrypanosomal and antimalarial acitivities of lycorine derivatives. Bioorg Med Chem 2008; 16: 10182-9. 28. Berkov S, Viladomat F, Codina C, Suarez S, Ravelo A, Bastida J. GC-MS of Amaryllidaceous galanthamine-type alkaloids. J Mass Spectrom 2012; 47: 1065-73. 29. Berkov S, Cuadrado M, Osorio E, Viladomat F, Codina C, Bastida J. Three new alkaloids from Galanthus nivalis and Galanthus elwesii. Planta Med 2009; 75: 1351-5. 30. Torras-Claveria L, Berkov S, Codina C, Viladomat F, Bastida J. Metabolomic analysis of bioactive Amaryllidaceae alkaloids of ornamental varieties of Narcissus by GC–MS combined with k-means cluster analysis. Ind Crop Prod 2014; 56: 211–22.