Pancratium canariense as an important source of amaryllidaceae alkaloids

Journal of Natural Products

Volumn 72, Issue 1, 2009, Pages 112-116

  Cedrón, Juan C ^a,b   Oberti, Juan C ^a,b   Estévez Braun, Ana ^a,b   Ravelo, Ángel G ^a,b   Del Arco Aguilar, Marcelino ^c   López, Matías ^a  

^a Instituto Universitario de Bio Organica Antonio Gonzalez   (Spain)

^b UNIVERSIDAD NACIONAL DE CÓRDOBA   (Argentina)

^c UNIVERSIDAD DE LA LAGUNA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

1 O ACETYL 8 NORPLUVIINE; 11 HYDROXYVITTATINE; 6 O METHYLHAEMANTHIDINE; 8 O DEMETHYLMARITIDINE; AMARYLLIDACEAE ALKALOID; HAEMANTHAMINE; HAEMANTHIDINE; HIPPEASTRINE; LYCORINE; PANCRACINE; PANCRATININE A; PANCRATININE B; PANCRATININE C; PANCRATININE D; TAZETTINE; UNCLASSIFIED DRUG; UNGIMINORINE; VITTATINE;

ARTICLE; DRUG STRUCTURE; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PANCRATIUM CANARIENSE; PLANT; PLANT BULB; X RAY DIFFRACTION; ANGIOSPERM; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; ISOLATION AND PURIFICATION; MEDICINAL PLANT; NUCLEAR MAGNETIC RESONANCE; SPAIN; X RAY CRYSTALLOGRAPHY;

AMARYLLIDACEAE; PANCRATIUM CANARIENSE;

AMARYLLIDACEAE ALKALOIDS; CRYSTALLOGRAPHY, X-RAY; LILIACEAE; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PLANTS, MEDICINAL; SPAIN;

EID: 60549104445     PISSN: 01633864     EISSN: None     Source Type: Journal    
DOI: 10.1021/np800459d     Document Type: Article

References (45)

1. Willis, J. C. A Dictionary of the Flowering Plants & Ferns, 8th ed.; Cambridge University Press: Cambridge, 1988.
2. Unver, N. Phytochem. Rev. 2007, 6, 125-135.
3. Zhong, J. Nat. Prod. Rep. 2005, 22, 111-126.
4. Jokhadze, M.; Eristavi, L.; Kutchukhidze, J.; Chariot, A.; Angenot, L.; Tits, M.; Jansen, O.; Frédérich, M. Phytoter. Res. 2007, 21, 622-624.
5. McNulty, J.; Nair, J.; Codina, C.; Bastida, J.; Pandey, S.; Gerasimoff, J.; Griffin, C. Phytochemistry 2007, 68, 1068-1074.
6. Elgorashi, E.; Stafford, G.; Van Staden, J. Planta Med. 2004, 70, 260-262.
7. Sener, B.; Orhan, I.; Satayavivad, J. Phytother. Res. 2003, 17, 1220-1223.
8. López, S.; Bastida, J.; Viladomat, F.; Codina, C. Life Sci. 2002, 71, 2521-2529.
9. Pettit, G.; Gaddamidi, V.; Cragg, G.; Herald, D.; Sagawa, Y. J. Chem. Soc., Chem. Commun. 1984, 24, 1693-1694.
10. Kekre, N.; Griffin, C.; McNulty, J.; Pandey, S. Cancer Chemother. Pharmacol. 2005, 56, 29-38.
11. Dewick, P. Medicinal Natural Products: A Biosynthetic Approach, 2nd ed.; John Wiley & Sons: England, 2002.
12. Amaryllidaceae website www.amaryllidaceae.org.
13. Izquierdo, I.; Martin, J.; Zurita, N.; Arechavaleta, M. Lista de especies silvestres de Canarias (hongos, plantas y animales terrestres); Consejería de Medio Ambiente y Ordenación Territorial, Gobierno de Canarias, Spain, 2004.
14. Evidente, A.; Andolfi, A.; Abou-Donia, A.; Touema, S.; Hammoda, H.; Shawky, E.; Motta, A. Phytochemistry 2004, 65, 2113-2118.
15. Labraña, J.; King'Ori, A.; Kricsfalusy, V.; Brun, R.; Codina, C.; Viladomat, F.; Bastida, J. Phytochemistry 2002, 60, 847-852.
16. Overman, L.; Shim, J. J. Org. Chem. 1993, 58, 4662-4672.
17. Vásquez-Tito, M.; Castedo, L.; Riguera, R. Heterocycles 1988, 27, 2833-2838.
18. Bohno, M.; Sugie, K.; Imase, H.; Yusof, Y.; Oishi, T.; Chida, N. Tetrahedron 2007, 63, 6977-6989.
19. Kihara, M.; Koike, T.; Imakura, Y.; Kida, K.; Shingu, T.; Kobayashi, S. Chem. Pharm. Bull. 1987, 35, 1070-1075.
20. Bastida, J.; Viladomat, F.; Llabres, J.; Codina, C.; Feliz, M.; Rubiralta, M. Phytochemistry 1987, 26, 1519-1524.
21. Antoun, M.; Mendoza, N.; Rios, Y.; Proctor, G.; Wickramaratne, D.; Pezzuto, J.; Kinghorn, D. J. Nat. Prod. 1993, 56, 1423-1425.
22. Nishimata, T.; Sato, Y.; Mori, M. J. Org. Chem. 2004, 69, 1837-1843.
23. Evidente, A. J. Nat. Prod. 1986, 49, 168-169.
24. Pham, L.; Gründemann, E.; Wagner, J.; Bartoszek, M.; Döpke, W. Phytochemistry 1999, 51, 327-332.
25. Baldwin, S.; Debenham, J. Org. Lett. 2000, 2, 99-102.
26. Jeffs, P.; Abou-Donia, A.; Campau, D. J. Org. Chem. 1985, 50, 1732-1737.
27. Wagner, J.; Pham, H.; Döpke, W. Tetrahedron 1996, 52, 6591-6600.
28. Latvala, A.; Önür, M.; Gözler, T.; Linden, A.; Kivcak, B.; Hesse, M. Phytochemistry 1995, 39, 1229-1240.
29. García, R.; Seco, J.; Vázquez, S.; Quínoa, E.; Riguera, R. J. Org. Chem. 2002, 67, 4579-4589.
30. Seco, J.; Quiñoá, E.; Riguera, R. Chem. Rev. 2004, 104, 17-117.
31. Ali, A.; Mesbah, M.; Frahm, A. Planta Med. 1984, 50, 188-189.
32. Quirion, J.; Husson, H.; Weniger, B.; Jiménez, F.; Zanoni, T. J. Nat. Prod. 1991, 54, 1112-1114.
33. Campbell, W.; Nair, J.; Gammon, D.; Codina, C.; Bastida, J.; Viladomat, F.; Smith, P.; Albrecht, C. Phytochemistry 2000, 53, 587-591.
34. Campbell, W.; Nair, J.; Gammon, D.; Bastida, J.; Codina, C.; Viladomat, F.; Smith, P.; Albrecht, C. Planta Med. 1998, 64, 91-93.
35. Herrera, M.; Machucho, A.; Fair, J.; Campbell, W.; Brun, R.; Viladomat, F.; Codina, C.; Bastida, J. Fitoterapia 2001, 72, 444-448.
36. Theoretical calculations were realized in Gaussian 03, version 6.0, employing the 6-31G basis. Energy calculations for α-N-oxide:-655838.3 kcal/mol. β-N-oxide:-655843.7 kcal/mol.
37. Kihara, M.; Konishi, K.; Xu, L.; Kobayashi, S. Chem. Pharm. Bull. 1991, 39, 1849-1853.
38. Kobayashi, S.; Satoh, K.; Numata, A.; Shingu, T.; Kihara, M. Phytochemistry 1991, 30, 675-677.
39. Suau, R.; Gómez, A.; Rico, R.; Vásquez-Tato, M.; Castedo, L.; Riguera, R. Phytochemistry 1988, 27, 3285-3287.
40. Suau, R.; Rico, R.; García, A.; Gómez, A. Heterocycles 1990, 31, 517-522.
41. Nonius, R. Nonius Kappa CCD Server Software; Delft, The Netherlands, 1998.
42. Otinowski, Z.; Minor, W. Methods in Enzymology, Vol. 276, Macromolecular Crystallography Part A; Carter, C., Sweet, R., Eds.; Academic Press: New York, 1997.
43. Altomare, A.; Burla, M.; Camalli, M.; Cascarazo, G.; Giacovazzo, C.; Guagliardi, A.; Moliterni, A.; Polidori, G.; Spagna, R. J. Appl. Crystallogr. 1999, 32, 115-119.
44. Sheldrick, G. SHELXL-97: Program for the Refinement of Crystal Structures; University of Göttingen: Germany, 1997.
45. Farrugia, L. J. Appl. Crystallogr. 1999, 32, 837-838.