Two New Alkaloids of the Crinane Series from Pancratium sickenbergeri

Abstract

Two new alkaloids; ent-6α/6β-hydroxybuphanisine, (-)-8-demethylmaritidine and seven known alkaloids were isolated from Pancratium sickenbergeri grown in Egypt. Three of the known alkaloids were tested in the NCI cytotoxicity screen, but were found to be inactive.

References

• 1 Lewis J R. Miscellaneous Alkaloids: Amaryllidaceae, Sceletium, muscarine, imidazole, oxazole, peptide and other miscellaneous alkaloids.  Nat. Prod. Rep.. 1999;  16 389-416
• 2 Lewis J R. Amaryllidaceae, muscarine, imidazole, oxazole, thiazole, and peptide alkaloids, and other miscellaneous alkaloids.  Nat. Prod. Rep.. 2000;  17 57-84
• 3 Martin S F. Amaryllidaceae alkaloids. In: Brossi A, ed The alkaloids. Academic Press, New York 1987 30: 251-376
• 4 Abbassy M A, El-Gougary O A, El-Hamady S, Sholo M A. Insecticidal, acaricidal and synergistic effects of soosan, Pancratium maritimum extracts and constituents.  J. Egypt. Soc. Parasitol.. 1998;  28 197-205
• 5 Ahmed Z F, Rizk A M, Hamouda F M. Phytochemical studies on Egyptian Pancratium species.  J. Nat. Prod.. 1964;  27 115-34
• 6 El Moghazy S A, Khalifa A A, Ramadan M A, Mesbah M K. Alkaloids and flavans from Pancratium sickenbergeri Asch. Proceedings of the First National Symbosium on Herbal Medicine, Assiut. Egypt 1992, 7 - 9 December
• 7 Ghosal S, Saini K S, Razdan S. Chemical constituents of the Amaryllidaceae. Crinum alkaloids: Their chemistry and biology.  Phytochemistry. 1985;  24 2141-56
• 8 DeAngelis G G, Wildman W C. Circular dichroism studies I. A quadrant rule for the optically active aromatic chromophore in rigid polycyclic systems.  Tetrahedron. 1969;  25 5099-112
• 9 Frahm A W, Ali A A, Kating H. Alkaloids of Crinum augustum. Part 3. Relative configuration of the alkaloid augustine.  Phytochemistry. 1981;  20 1735-8
• 10 Pabuccuoglu V, Richomme P, Gozler T, Kivcak B, Freyer A J, Shamma M. Four new crinine-type alkaloids from Sternbergia species.  J. Nat. Prod.. 1989;  52 785-91
• 11 Bastida J, Viladomat F, Llabres J M, Codina C, Feliz M. Rubiralta M. Narcissus alkaloids. Part 4. Alkaloids from Narcissus confusus .  Phytochemistry. 1987;  26 1519-24
• 12 King R W, Murphy C F, Wildman W C. 6-Hydroxycrinamine and haemanthidine.  J. Amer. Chem. Soc.. 1965;  87 4912-7
• 13 Ali A A, Kating H, Frahm A W. Alkaloids of Crinum augustum. Part 2. Four 6-hydroxylated alkaloids in the crinine series from Crinum augustum .  Phytochemistry. 1981;  20 1731-33
• 14 Bastida J, Codina C, Viladomat F, Rubiralta M, Quirion J C, Husson H P, Ma G E. Narcissus alkaloids, XIII. Complete assignment of the NMR spectra of papyramine and 6-epi-papyramine by two-dimensional NMR spectroscopy.  J. Nat. Prod.. 1990;  53 1456-62
• 15 Duffield A M, Aplin R T, Budzikiewicz H, Djerassi C, Murphy C F, Wildman W C. Mass specrometry in structural and stereochemical problems LXXXII A study of the fragmentation of some Amaryllidaceae alkaloids.  J. Amer. Chem. Soc.. 1965;  87 4902-12
• 16 Kihara M, Koike T, Imakura Y, Kida K, Shingu T, Kobayashi S. Alkaloidal constituents of Hymenocallis rotata Herb. (Amaryllidaceae).  Chem. Pharm. Bull.. 1987;  35 1070-5
• 17 Antoun M D, Mendoza N T, Rios Y R, Proctor G R, Wickramaratne D BM, Pezzuto J M, Kinghorn A D. Cytotoxicity of Hymenocallis expansa alkaloids.  J. Nat. Prod.. 1993;  56 1423-5
• 18 Mugge C, Schablinski B, Obst K, Dopke W. Alkaloids from Hippeastrum Hybrids.  Pharmazie. 1994;  49 444-7
• 19 Ali A A, Mesbah M K, Frahm A W. Phytochemical investigation of Hippeastrum vittatum. Part IV: Stereochemistry of pancracine, the first 5, 11-methanomorphanthridine alkaloid from Hippeastrum. Structure of hippagine.  Planta Med.. 1984;  50 1
• 20 Abdel-Kader M S, Wisse J, Evans R, Werff H, Kingston D GI. Bioactive iridoids and a new lignan from Allamanda cathartica and Himatanthus fallax from the Suriname rain forest.  J. Nat. Prod.. 1997;  60 1294-7