Analysis of bioactive amaryllidaceae alkaloid profiles in Lycoris species by GC-MS

Natural Product Communications

Volumn 9, Issue 8, 2014, Pages 1081-1086

  Guo, Ying ^a   Pigni, Natalia B ^a   Zheng, Yuhong ^b   De Andrade, Jean Paulo ^a   Torras Claveria, Laura ^a   De Souza Borges, Warley ^c   Viladomat, Francesc ^a   Codina, Carles ^a   Bastida, Jaume ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

^b Jiangsu Province and Chinese Academy of Scienc es   (China)

^c FEDERAL UNIVERSITY OF ESPÍRITO SANTO   (Brazil)

Author keywords

Amaryllidaceae alkaloids; Galanthamine; GC MS; Lycorine; Lycoris

Indexed keywords

AMARYLLIDACEAE ALKALOID; GALANTAMINE; HAEMANTHAMINE; LYCORINE; NARCICLASINE; TAZETTINE;

AMARYLLIDACEAE; ARTICLE; CHINA; DERIVATIZATION; LYCORIS; LYCORIS ALBIFLORA; LYCORIS AUREA; LYCORIS CHINENSIS; LYCORIS HAYWARDII; LYCORIS INCARNATA; LYCORIS RADIATA; LYCORIS SPRENGERI; LYCORIS SQUAMIGERA; MASS FRAGMENTOGRAPHY; NONHUMAN; OXIDATIVE COUPLING;

ALKALOIDS; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; LILIACEAE; LYCORIS; MOLECULAR STRUCTURE; PLANT EXTRACTS;

EID: 84906685894     PISSN: 1934578X     EISSN: 15559475     Source Type: Journal    
DOI: 10.1177/1934578x1400900806     Document Type: Article

References (40)

1. Berkov S, Codina C, Bastida J. (2007) The genus Galanthus: a source of bioactive compounds. In Phytochemicals - A Global Perspective of Their Role in Nutrition and Health. Rao V. (Ed.), InTech, Rijeka, 235-254.
2. Wang L, Yin ZQ, Cai Y, Zhang XQ, Yao XS, Ye WC. (2010) Amaryllidaceae alkaloids from the bulbs of Lycoris radiata. Biochemical Systematics and Ecology, 38, 444-446.
3. Bastida J, Lavilla R, Viladomat F. (2006) Chemical and biological aspects of Narcissus alkaloids. In Alkaloids. Cordell GA. (Ed.), Elsevier Scientific Publishing, Amsterdam, 87-179. (Pubitemid 44507281)
4. Jin Z. (2009) Amaryllidaceae and Sceletium alkaloids. Natural Product Reports, 26, 363-381.
5. Schmeda-Hirschmann G, Rodriguez JA, Loyola JI, Astudillo L, Bastida J, Viladomat F, Codina C. (2000) Activity of amaryllidaceae alkaloids on the blood pressure of normotensive rats. Pharmacy and Pharmacology Communications, 6, 309-312. (Pubitemid 30470049)
6. McNulty J, Nair JJ, Singh M, Crankshaw DJ, Holloway AC, Bastida J. (2010) Cytochrome P450 3A4 inhibitory activity studies within the lycorine series of alkaloids. Natural Product Communications, 5, 1195-1200.
7. de Andrade JP, Pigni NB, Torras-Claveria L, Guo Y, Berkov S, Reyes-Chilpa R, El AA, Zuanazzi JAS, Codina C, Viladomat F, Bastida J. (2012) Alkaloids from the Hippeastrum genus: chemistry and biological activity. Revista Latinoamericana de Química, 40, 83-98.
8. Sarikaya BB, Berkov S, Bastida J, Kaya GI, Onur MA, Somer NU. (2013) GC-MS investigation of Amaryllidaceae alkaloids in Galanthus xvalentinei nothosubsp. subplicatus. Natural Product Communications, 8, 327-328.
9. Cahlikova L, Macakova K, Zavadil S, Jiros P, Opletal L, Urbanova K, Jahodar L. (2011) Analysis of Amaryllidaceae alkaloids from Chlidanthus fragrans by GC-MS and their cholinesterase activity. Natural Product Communications, 6, 603-606.
10. de Andrade JP, Pigni NB, Torras-Claveria L, Berkov S, Codina C, Viladomat F, Bastida J. (2012) Bioactive alkaloid extracts from Narcissus broussonetii: mass spectral studies. Journal of Pharmaceutical and Biomedical Analysis, 70, 13-25.
11. da Silva AF, de Andrade JP, Bevilaqua LR, de Souza MM, Izquierdo I, Henriques AT, Zuanazzi JA. (2006) Anxiolytic-, antidepressant- and anticonvulsant-like effects of the alkaloid montanine isolated from Hippeastrum vittatum. Pharmacology Biochemistry and Behavior, 85, 148-154. (Pubitemid 44802739)
12. Pagliosa LB, Monteiro SC, Silva KB, de Andrade JP, Dutilh J, Bastida J, Cammarota M, Zuanazzi JA. (2010) Effect of isoquinoline alkaloids from two Hippeastrum species on in vitro acetylcholinesterase activity. Phytomedicine, 17, 698-701.
13. Silva AF, de Andrade JP, Machado KR, Rocha AB, Apel MA, Sobral ME, Henriques AT, Zuanazzi JA. (2008) Screening for cytotoxic activity of extracts and isolated alkaloids from bulbs of Hippeastrum vittatum. Phytomedicine, 15, 882-885.
14. Castilhos TS, Giordani RB, Henriques AT, Menezes FS, Zuanazzi JAS. (2007) In vitro evaluation of the antiinflammatory, antioxidant and antimicrobial activities of the montanine alkaloid. Revista Brasileira de Farmacognosia, 17, 209-214.
15. Morishima K. (1899) Alkaloids contained in Lycoris radiata herb. Archiv fur Experimentelle Pathologie und Pharmakologie, 40, 221-240.
16. Kondo H, Tomimura K, Ishiwata S. (1932) Alkaloids of Lycoris radiata herb. V and VI. Journal of the Pharmaceutical Society of Japan, 52, 433-458 (in German 451-434).
17. Kondo H, Ikeda T. (1940) Lycoris alkaloids. XVI. Constitution of lycorenine. 3. Berichte der Deutschen Chemischen Gesellschaft, B: Abhandlungen, 73B, 867-874.
18. Kondo H, Katura H. (1940) Lycoris alkaloids. XV. Constitution of lycorine. 7. Journal of the Pharmaceutical Society of Japan, 60, 101-105.
19. Kondo H, Ikeda T, Tagal J. (1954) Lycoris alkaloids. XXVII. Structure of tazettine. The Annual Report of ITSUU Laboratory, No. 5, 72-79.
20. Boit HG, Ehmke H. (1957) Amaryllidaceae alkaloids. XVI. Alkaloids of Nerine corusca, N. flexuosa, Pancratium illyricum, Lycoris aurea, and L. incarnata. Chemische Berichte, 90, 369-373.
21. Uyeo S, Yanaihara N. (1959) Phenolic alkaloids occurring in Lycoris radiata. Journal of the Chemical Society (Resumed), 172-177.
22. Hung SH, Ma KE. (1964) The alkaloids of Amaryllidaceae. III. The alkaloids of Lycoris squamigera and two other Lycoris species, and a new alkaloid, squamigerine. Acta Pharmaceutica Sinica, 11, 1-14.
23. Kobayashi S, Takeda S, Ishikawa H, Matsumoto H, Kihara M, Shingu T, Numata A, Uyeo S. (1976) Alkaloids of amaryllidaceae. A new alkaloid, sanguinine, from Lycoris sanguinea Maxim. var. kiushiana Makino, and pretazettine from Lycoris radiata herb. Chemical and Pharmaceutical Bulletin, 24, 1537-1543.
24. Takagi S, Yamaki M. (1974) Constituents of the bulbs of Lycoris sanguinea. Journal of the Pharmaceutical Society of Japan, 94, 617-622.
25. Kobayashi S, Yuasa K, Imakura Y, Kihara M, Shingu T. (1980) Isolation of O-demethyllycoramine from bulbs of Lycoris radiata Herb. Chemical and Pharmaceutical Bulletin, 28, 3433-3436. (Pubitemid 11169101)
26. Li HY, Ma GE, Xu Y, Hong SH. (1987) Studies on the alkaloids of Amaryllidaceae. Part X. Alkaloids of Lycoris guangxiensis. Planta Medica, 53, 259-261.
27. Ma GE, Li HY, Huang HZ, Yan LY, Hong SH. (1987) Alkaloids of Lycoris. XI. Antitumor principles and the alkaloids of Lycoris chinensis. Chinese Traditional and Herbal Drugs, 18, 342-345.
28. Kihara M, Xu L, Konishi K, Kida K, Nagao Y, Kobayashi S, Shingu T. (1994) Isolation and structure elucidation of a novel alkaloid, incartine, a supposed biosynthetic intermediate, from flowers of Lycoris incarnata. Chemical and Pharmaceutical Bulletin, 42, 289-292. (Pubitemid 24119646)
29. Abdallah OM. (1995) Minor alkaloids from Lycoris sanguinea. Phytochemistry, 39, 477-478.
30. Yang Y, Huang SX, Zhao YM, Zhao QS, Sun HD. (2005) Alkaloids from the bulbs of Lycoris aurea. Helvetica Chimica Acta, 88, 2550-2553. (Pubitemid 41391631)
31. Wang L, Zhang XQ, Yin ZQ, Wang Y, Ye WC. (2009) Two new Amaryllidaceae alkaloids from the bulbs of Lycoris radiata. Chemical and Pharmaceutical Bulletin, 57, 610-611.
32. Pi HF, Zhang P, Ruan HL, Zhang YH, Sun HD, Wu JZ. (2009) A new alkaloid from Lycoris aurea. Chinese Chemical Letters, 20, 1319-1320.
33. Takayama H, Kinoshita E, Kitajima M, Kogure N. (2009) Two new alkaloids from bulbs of Lycoris squamigera. Heterocycles, 77, 1389.
34. Hao B, Shen SF, Zhao QJ. (2013) Cytotoxic and antimalarial amaryllidaceae alkaloids from the bulbs of Lycoris radiata. Molecules, 18, 2458-2468.
35. Huang SD, Zhang Y, He HP, Li SF, Tang GH, Chen DZ, Cao MM, Di YT, Hao XJ. (2013) A new Amaryllidaceae alkaloid from the bulbs of Lycoris radiata. Chinese Journal of Natural Medicines, 11, 406-410.
36. Feng T, Wang YY, Su J, Li Y, Cai XH and Luo XD. (2011) Amaryllidaceae alkaloids from Lycoris radiata. Helvetica Chimica Acta, 94, 178-183.
37. Berkov S, Pavlov A, Ilieva M, Burrus M, Popov S, Stanilova M. (2005) CGC-MS of alkaloids in Leucojum aestivum plants and their in vitro cultures. Phytochemical Analysis, 16, 98-103. (Pubitemid 40533157)
38. Torras-Claveria L, Berkov S, Codina C, Viladomat F, Bastida J. (2014) Metabolomic analysis of bioactive Amaryllidaceae alkaloids of ornamental varieties of Narcissus by GC-MS combined with k-means cluster analysis. Industrial Crops and Products, 56, 211-222.
39. Sun ZF, Mu SZ, Ge YH, Hao XJ. (2012) Alkaloid type analysis of Lycoris radiata and Lycoris aurea using GC-MS method. Journal of Mountain Agriculture and Biology, 89-91.
40. Wang XY, Huang MR, Han ZM, Zhou J. (2007) GC-MS analysis of chemical components from the bulbs of Lycoris aurea. Chinese Traditional and Herbal Drugs, 38, 188-217.