Metabolomic analysis of bioactive Amaryllidaceae alkaloids of ornamental varieties of Narcissus by GC-MS combined with k-means cluster analysis

Industrial Crops and Products

Volumn 56, Issue , 2014, Pages 211-222

  Torras Claveria, Laura ^a   Berkov, Strahil ^b   Codina, Carles ^a   Viladomat, Francesc ^a   Bastida, Jaume ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

^b AGROBIOINSTITUTE   (Bulgaria)

Author keywords

Amaryllidaceae alkaloids; GC MS; Metabolomics; Multivariate statistical analysis; Narcissus cultivars

Indexed keywords

ALKALOIDS; CLUSTER ANALYSIS; NITROGEN COMPOUNDS; PLANTS (BOTANY);

AMARYLLIDACEAE ALKALOIDS; GC-MS; METABOLOMICS; MULTIVARIATE STATISTICAL ANALYSIS; NARCISSUS CULTIVARS;

METABOLITES;

ALKALOID; BIOACTIVITY; CHEMICAL COMPOSITION; CLUSTER ANALYSIS; HERB; HORTICULTURE; METABOLISM;

EID: 84897472008     PISSN: 09266690     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.indcrop.2014.03.008     Document Type: Article

References (45)

1. Bartel J., Krumsiek J., Theis F.J. Statistical methods for the analysis of high-throughput metabolomics data. Comput. Struct. Biotechnol. J. 2013, 5. 10.5936/csbj.201301009.
2. Bastida J., Lavilla R., Viladomat F. Chemical and biological aspects of Narcissus alkaloids. The Alkaloids 2006, vol. 63:87-179. Elsevier, Chicago.
3. Bastida J., Berkov S., Torras L., Pigni N.B., de Andrade J.P., Martínez V., Codina C., Viladomat F. Chemical and biological aspects of Amaryllidaceae alkaloids. Recent Advances in Pharmaceutical Sciences 2011, 65-100. Transword Research Network, Kerala. D. Muñoz-Torrero (Ed.).
4. Ben El Hadj Ali I., Guetat A., Boussaid M. A combined approach using allozimes and volatiles for the characterization of Tunisian Thymbra capitata (L.) Cav (Lamiaceae). Ind. Crop. Prod. 2013, 43:477-483.
5. Berkov S., Bastida J., Viladomat F., Codina C. Analysis of galanthamine-type alkaloids by capillary gas chromatography-mass spectrometry in plants. Phytochem. Anal. 2008, 19:285-293.
6. Berkov S., Georgieva L., Kondakova V., Atanassov A., Viladomat F., Bastida J., Codina C. Plant sources of galanthamine: phytochemical and biotechnological aspects. Biotechnol. Biotechnol. Equip. 2009, 23:1170-1176.
7. Berkov S., Bastida J., Sidjimova B., Viladomat F., Codina C. Alkaloid diversity in Galanthus elwesii and Galanthus nivalis. Chem. Biodivers. 2011, 8:115-130.
8. Berkov S., Bastida J., Viladomat F., Codina C. Development and validation of a GC-MS method for rapid determination of galanthamine in Leucojum aestivum and Narcissus ssp.: a metabolomic approach. Talanta 2011, 83:1455-1465.
9. Ceriotti G. Narciclasine: an antimitotic substance from Narcissus bulbs. Nature 1967, 213:595-596.
10. Cherkasov O.A., Tolkachev O.N. Narcissus and other Amaryllidaceae as sources of galanthamine. Narcissus and Daffodil. The Genus Narcissus 2002, 242-255. Taylor & Francis, London. G.R. Hanks (Ed.).
11. Cuthbertson D., Andrews P.K., Reganold J.P., Davies N.M., Lange B.M. Utility of metabolomics toward assessing the metabolic basis of quality traits in apple fruit with an emphasis on antioxidants. J. Agric. Food Chem. 2012, 60:8552-8560.
12. de Andrade J.P., Pigni N.B., Torras-Claveria L., Berkov S., Codina C., Viladomat F., Bastida J. Bioactive alkaloid extracts from Narcissus broussonetii: mass spectral studies. J. Pharm. Biomed. Anal. 2012, 70:13-25.
13. Dumont P., Ingrassia L., Rouzeau S., Ribaucour F., Thomas S., Roland I., Darro F., Lefranc F., Kiss R. The Amaryllidaceae isocarbostyril narciclasine induces apoptosis by activation of the death receptor and/or mitochondrial pathways in cancer cells but not in normal fibroblasts. Neoplasia 2007, 9:766-776.
14. Eichhorn J., Takada T., Kita Y., Zenk M.H. Biosynthesis of the Amaryllidaceae alkaloid galanthamine. Phytochemistry 1998, 49:1037-1047.
15. Fennell C.W., van Staden J. Crinum species in traditional and modern medicine. J. Ethnopharmacol. 2001, 78:15-26.
16. Giordani R.B., Vieira P.deB., Weizenmann M., Rosemberg D.B., Souza A.P., Bonorino C., de Carli G.A., Bogo M.R., Zuanazzi J.A., Tasca T. Lycorine induces cell death in the amitochondriate parasite, Trichomonas vaginalis, via an alternative non-apoptotic death pathway. Phytochemistry 2011, 72:645-650.
17. Goietsenoven G.V., Andolfi A., Lallemand B., Cimmino A., Lamoral-Theys D., Gras T., Abou-Donia A., Dubois J., Lefranc F., Mathieu V., Kornienko A., Kiss R., Evidente A. Amaryllidaceae alkaloids belonging to different structural subgroups display activity against apoptosis-resistant cancer cells. J. Nat. Prod. 2010, 73:1223-1227.
18. Iqbal Z., Nasir H., Hiradate S., Fujii Y. Plant growth inhibitory activity of Lycoris radiata Herb. and the possible involvement of lycorine as an allelochemical. Weed Biol. Manag. 2006, 6:221-227.
19. Issaq H.J., Van Q.N., Waybright T.J., Muschik G.M., Veenstra T.D. Analytical and statistical approaches to metabolomics research. J. Sep. Sci. 2009, 32:2183-2199.
20. Jain A.K., Murty M.N., Flynn P.J. Data clustering: a review. ACM Comput. Surv. 1999, 31:264-323.
21. Jain A.K. Data clustering: 50 years beyond k-means. Pattern Recognit. Lett. 2010, 31:651-666.
22. Jin Z. Amaryllidaceae and Sceletium alkaloids. Nat. Prod. Rep. 2007, 24:886-905.
23. Kang J., Zhang Y., Cao X., Fan J., Li G., Wang Q., Diao Y., Zhao Z., Luo L., Yin Z. Lycorine inhibits lipopolysaccharide-induced iNOS and COX-2 up-regulation in RAW264.7 cells through suppressing P38 and STATs activation and increases the survival rate of mice after LPS challenge. Int. Immunopharmacol. 2012, 12:249-256.
24. Kaya G.I., Sarikaya B., Onur M.A., Somer N.U., Viladomat F., Codina C., Bastida J., Lauinger I.L., Kaiser M., Tasdemir D. Antiprotozoal alkaloids from Galanthus trojanus. Phytochem. Lett. 2011, 4:301-305.
25. Kreh M. Studies on galanthamine extraction from Narcissus and other Amaryllidaceae. Narcissus and Daffodil. The Genus Narcissus 2002, 257-272. Taylor & Francis, London/New York. G.R. Hanks (Ed.).
26. Li Y., Liu J., Tang L., Shi Y., Ren W., Hu W. Apoptosis induced by lycorine in KM3 cells is associated with the G0/G1 cell cycle arrest. Oncol. Rep. 2007, 17:377-384.
27. Liland K.H. Multivariate methods in metabolomics-from pre-processing to dimension reduction and statistical analysis. Trends Anal. Chem. 2011, 30:827-841.
28. López S., Bastida J., Viladomat F., Codina C. Galanthamine pattern in Narcissus confusus plants. Planta Med. 2003, 69:1166-1168.
29. 1H NMR. Phytochem. Anal. 2010, 21:66-72.
30. 1H NMR. J. Agric. Food Chem. 2011, 59:3155-3161.
31. Lubbe A., Gude H., Verpoorte R., Choi Y.H. Seasonal accumulation of major alkaloids in organs of pharmaceutical crop Narcissus Carlton. Phytochemistry 2013, 88:43-53.
32. Martindale The Complete Drug Reference 2013, Pharmaceutical Press, London, United Kingdom, (online, accessed July 2013). http://www.medicinescomplete.com/mc/martindale/current/index.htm.
33. Mc Nulty J., Nair J.J., Codina C., Bastida J., Pandey S., Gerasimoff J., Griffin C. Selective apoptosis-inducing activity of Crinum-type Amaryllidaceae alkaloids. Phytochemistry 2007, 68:1068-1074.
34. Moraes R.M. Galanthamine production from Narcissus: agronomic and related considerations. Narcissus and Daffodil. The Genus Narcissus 2002, 273-285. Taylor & Francis, London/New York. G.R. Hanks (Ed.).
35. Moraes-Cerdeira R.M., Burandt C.L., Bastos J.K., Nanayakkara N.P.D., Mikell J., Thurn J., McChesney J.D. Evaluation of four Narcissus cultivars as potential sources for galanthamine production. Planta Med. 1997, 63:472-474.
36. Pettit G.R., Tan R., Bao G., Melody N., Doubeck D.L., Gao S., Chapuis J., Williams L. Antineoplastic agents, 587. Isolation and structure of 3-epipancratistatin from Narcissus cv. Ice Follies. J. Nat. Prod. 2012, 75:771-773.
37. Rønsted N., Savolainen V., Mølgaard P., Jäger A.K. Phylogenetic selection of Narcissus species for drug discovery. Biochem. Syst. Ecol. 2008, 36:417-422.
38. Şener B., Orhan I., Satayavivad J. Antimalarial activity screening of some alkaloids and the plant extracts from Amaryllidaceae. Phytother. Res. 2003, 17:1220-1223.
39. Shukla S., Yadav H.K., Rastogi A., Mishra B.K., Singh S.P. Alkaloid diversity in relation to breeding for specific alkaloids in opium poppy (Papaver somniferum L.). Czech J. Genet. Plant Breed. 2010, 4:164-169.
40. Stranska I., Skalicky M., Novak J., Matyasova E., Hejnak V. Analysis of selected poppy (Papaver somniferum L.) cultivars: pharmaceutically important alkaloids. Ind. Crop. Prod. 2013, 41:120-126.
41. Takos A.M., Rook F. Towards a molecular understanding of the biosynthesis of Amaryllidaceae alkaloids in support of their expanding medical use. Int. J. Mol. Sci. 2013, 14:11713-11741.
42. Torras-Claveria L., Berkov S., Jáuregui O., Caujapé J., Viladomat F., Codina C., Bastida J. Metabolic profiling of bioactive Pancratium canariense extracts by GC-MS. Phytochem. Anal. 2010, 21:80-88.
43. Torras-Claveria L., Berkov S., Codina C., Viladomat F., Bastida J. Daffodils as potential crops of galanthamine. Assessment of more than 100 ornamental varieties for their alkaloid content and acetylcholinesterase inhibitory activity. Ind. Crop. Prod. 2013, 43:237-244.
44. Viladomat F., Llabrés J.M., Bastida J., Cusidó R.M., Codina C. Ontogenic variations in the alkaloids of Narcissus assoanus. Physiol. Plant. 1986, 68:657-661.
45. Worley B., Powers R. Multivariate analysis in metabolomics. Curr. Metabolomics 2013, 1:91-106.