Indole alkaloid marine natural products: An established source of cancer drug leads with considerable promise for the control of parasitic, neurological and other diseases

Life Sciences

Volumn 78, Issue 5, 2005, Pages 442-453

  Gul, Waseem ^a,b   Hamann, Mark T ^a  

^a UNIVERSITY OF MISSISSIPPI   (United States)

^b ElSohly Laboratories Incorporated   (United States)

Author keywords

Bioactive marine natural products; Indole alkaloids; New drug leads

Indexed keywords

DRAGMACIDIN; DRAGMACIDIN D; EUDISTALBIN A; EUDISTOMIN E; EUDISTOMIN K; GELLIUSINE A; GELLIUSINE B; GROSSULARINE 1; GROSSULARINE 2; HALOCYAMINE A; HALOCYAMINE B; HYRTIOSIN A; HYRTIOSIN B; INDOLE ALKALOID; ISOAPLYSIN A; ISOPHAKELLISTATIN 3; KAPAKAHINE B; KONBAMIDIN; MAKALUVAMINE G; NATURAL PRODUCT; NORTOPSENTIN A; NORTOPSENTIN B; NORTOPSENTIN C; PHAKELLISTATIN 3; STAUROSPORINE; STYELIN D; TOPSENTIN; TOPSENTIN B1; TOPSENTIN B2; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANTIBACTERIAL ACTIVITY; ANTIINFLAMMATORY ACTIVITY; ANTIVIRAL ACTIVITY; ASCIDIACEA; BREAST CANCER; CALCIUM TRANSPORT; CANCER CELL; CANCER RESEARCH; CONFERENCE PAPER; CYTOTOXICITY; DRUG ACTIVITY; DRUG RESEARCH; DRUG SCREENING; DRUG STRUCTURE; HUMAN; IC 50; LIVER CELL CARCINOMA; LUNG CANCER; MARINE ENVIRONMENT; NEUROBLASTOMA; NONHUMAN; SPONGE (PORIFERA); STREPTOMYCES; STRUCTURE ACTIVITY RELATION;

ALKALOIDS; ANIMALS; ANTI-INFECTIVE AGENTS; ANTINEOPLASTIC AGENTS; ANTIPARASITIC AGENTS; BIOLOGICAL PRODUCTS; ENZYME INHIBITORS; HUMANS; INDOLES; NEOPLASMS; NERVOUS SYSTEM DISEASES; NEUROPROTECTIVE AGENTS; PARASITIC DISEASES; SEROTONIN AGENTS;

ASCIDIACEA; PORIFERA; STREPTOMYCES;

EID: 27844463013     PISSN: 00243205     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.lfs.2005.09.007     Document Type: Conference Paper

References (53)

1. S.A. Adesanya, M. Chbani, M. Pais, and C. Debitus Brominated β-carbolines from the marine tunicate Eudistoma album Journal of Natural Products 55 4 1992 525 527
2. K. Azumi, H. Yokosawa, and S. Ishii Halocyamines: novel antimicrobial tetrapeptide-like substances isolated from the hemocytes of the solitary ascidian Halocynthia roretzi Biochemistry 29 1990 159 165
3. D.A. Benson, I. Karsch-Mizrachi, D.J. Lipman, J. Ostell, B.A. Rapp, and D.L. Wheeler Genbank Nucleic Acids Research 28 1 2000 15 18
4. G. Bifulco, I. Bruno, L. Minale, R. Riccio, A. Calignano, and C. Debitus (±)-Gelliusines A and B, two diastereomeric brominated tris-indole alkaloids from a deep water New Caledonian marine sponge (Gellius or Orina sp.) Journal of Natural Products 57 9 1994 1294 1299
5. G. Bifulco, I. Bruno, R. Riccio, J. Lavayre, and G. Bourdy Further brominated bis- and tris-indole alkaloids from the deep-water New Caledonian marine sponge Orina sp. Journal of Natural Products 58 8 1995 1254 1260
6. J.W. Blunt, and M.H.G. Munro University of Canterbury, Marinlit: a Database of the Literature on Marine Natural Product 2001
7. S.C. Bobzin, and D.J. Faulkner Aromatic alkaloids from the marine sponge chelonaplysilla sp. Journal of Organic Chemistry 56 1991 4403 4407
8. H.R. Bokesch, L.K. Pannell, T.C. McKee, and M.R. Boyd Coscinamides A, B and C, three new bis-indole alkaloids from the marine sponge Coscinoderma sp. Tetrahedron Letters 41 2000 6305 6308
9. R.J. Capon Marine bioprospecting - trawling for treasure and pleasure European Journal of Organic Chemistry 4 2001 633 645
10. J.R. Carney, P.J. Scheuer, and M. Kelly-Borges Makaluvamine G, a cytotoxic pigment from an Indonesian sponge Histodermella sp. Tetrahedron 49 38 1993 8483 8486
11. A. Casapullo, G. Bifulco, I. Bruno, and R. Riccio New bisindole alkaloids of the topsentin and hamacanthin classes from the Mediterranean marine sponge Rhaphisia lacazei Journal of Natural Products 63 2000 447 451
12. M. Donia, and M.T. Hamann Marine natural products and their potential applications as anti-infective agents The Lancet Infectious Diseases 3 2003 338 348
13. K.A. El Sayed, P. Bartyzel, X. Shen, T.L. Perry, J.K. Zjawiony, and M.T. Hamann Marine natural products as antituberculosis agents Tetrahedron 56 2000 949 953
14. D.J. Faulkner Marine natural products Natural Product Reports 19 2002 1 48
15. D.J. Gochfeld, K.A. El Sayed, M. Yousaf, J.F. Hu, P. Bartyzel, D.C. Dunbar, S.P. Wilkins, J.K. Zjawiony, R.F. Schinazi, S.S. Wirtz, P.M. Tharnish, and M.T. Hamann Marine natural products as lead anti-HIV agents Mini Reviews in Medicinal Chemistry 3 2003 401 424
16. S.P. Gunasekera, S.A. Pomponi, and P.J. McCarthy Discobahamins A and B, new peptides from the Bahamian deep water marine sponge Discodermia sp. Journal of Natural Products 57 1 1994 79 83
17. M.T. Hamann Enhancing marine natural product structural diversity and bioactivity through semisynthesis and biocatalysis Current Pharmaceutical Design 9 2003 879 889
18. J.F. Hu, J.A. Schetz, M. Kelly, J.N. Peng, K.K.H. Ang, H. Flotow, C.Y. Leong, S.B. Ng, A.D. Buss, S.P. Wilkins, and M.T. Hamann New antiinfective and human 5-HT2 receptor binding natural and semisynthetic compounds from the Jamaican sponge Smenospongia aurea Journal of Natural Products 65 4 2002 476 480
19. J.F. Hu, M.T. Hamann, R. Hill, and M. Kelly The manzamine alkaloids The Alkaloids 60 2003 207 285
20. B. Jiang, J.M. Smallheer, C. Amaral-Ly, and M.A. Wuonola Total synthesis of (±)-Dragmacidin: a cytotoxic bis (indole) alkaloid of marine origin Journal of Organic Chemistry 59 1994 6823 6827
21. B. Jiang, C.G. Yang, and J. Wang Enantioselective synthesis of marine indole alkaloid Hamacanthin B Journal of Organic Chemistry 67 2002 1396 1398
22. C. Jimenez, E. Quinoa, M. Adamczeski, L.M. Hunter, and P. Crews Novel sponge-derived amino acids. 12. Tryptophan-derived pigments and accompanying sesterterpenes from fascaplysinopis reticulata Journal of Organic Chemistry 56 1991 3403 3410
23. Y. Kamano, H.P Zhang, Y. Ichihara, H. Kizu, K. Komiyama, and G.R. Pettit Convolutamydine A, a novel bioactive hydroxyoxindole alkaloid from marine bryozoan Amathia convoluta. Tetrahedron Letters 36 16 1995 2783 2784
24. O. Kayser, A.F. Kiderlen, and S.L. Croft Natural products as antiparasitic drugs Parasitic Res 90 2002 S55 S62
25. J. Kobayashi, H. Nakamura, Y. Ohizumi, and Y. Hirata Eudistomidin-A, a novel calmodulin antagonist from the Okinawan tunicate Eudistoma glaucus Tetrahedron Letters 27 10 1986 1191 1194
26. J. Kobayashi, M. Ishibashi, U. Nagai, and Y. Ohizumi 9-Methyl-7- bromoeudistomin D, a potent inducer of calcium release from sarcoplasmic reticulum of skeletal muscle Experientia 45 1989 782 783
27. J. Kobayashi, T. Murayama, M. Ishibashi, S. Kosuge, M. Takamatsu, Y. Ohizumi, H. Kobayashi, T. Ohta, S. Nozoe, and T. Sasaki Hyrtiosins A and B, new indole alkaloids from the Okinawan marine sponge Hyrtios erecta Tetrahedron 46 23 1990 7699 7702
28. S. Kohmoto, Y. Kashman, O.J. McConnell, K.L. Rinehart, A. Wright, and F. Koehn Dragmacidin, a new cytotoxic bis (indole) Alkaloid from a deep water marine sponge, Dragmacidon sp Journal of Organic Chemistry 53 1988 3116 3118
29. K. Kondo, J. Nishi, M. Ishibashi, and J. Kobayashi Two new tryptophan-derived alkaloids from the Okinawan marine sponge Aplysina sp. Journal of Natural Products 57 7 1994 1008 1011
30. G.M. Konig, A.D. Wright, O. Sticher, C.K. Angerhofer, and J.M. Pezzuto Biological activities of selected marine natural products Planta Medica 60 1994 532 537
31. R.J. Lake, J.W. Blunt, and M.H.G. Munro Eudistomins from the New Zealand Ascidian Ritterella sigillinoides Australian Journal of Chemistry 42 1989 1201 1206
32. M.V. Laycock, J.L.C. Wright, J.A. Findlay, and A.D. Patil New physostigmine related bromoalkaloids from the marine bryozoan Flustra foliacea Canadian Journal of Chemistry 64 1986 1312 1316
33. G. Lidgren, L. Bohlin, and J. Bergman Studies of Swedish marine organisms VII. A novel biologically active indole alkaloid from the sponge Geodia baretti Tetrahedron Letters 27 28 1986 3283 3284
34. T.N. Makarieva, A.S. Dmitrenok, P.S. Dmitrenok, B.B. Grebnev, and V.A. Stonik Pibocin B, the first N-O-Methylindole marine alkaloid, a metabolite from the Far-Eastern ascidian Eudistoma species Journal of Natural Products 64 2001 1559 1561
35. A.M.S. Mayer, and M.T. Hamann Marine pharmacology in 1999: compounds with antibacterial, anticoagulant, antifungal, anthelmintic, antiinflammatory, antiplatelet, antiprotozoal and antiviral activities; affecting the cardiovascular, endocrine, immune and nervous systems and other miscellaneous mechanisms of action Comparative Biochemistry and Physiology, Part C Toxicology and Pharmacology 132C 2002 315 339
36. A.M.S. Mayer, and M.T. Hamann Marine pharmacology in 2000: compounds with antibacterial, anticoagulant, antifungal, anthelmintic, antiinflammatory, antiplatelet, antiprotozoal and antiviral activities; affecting the cardiovascular, endocrine, immune and nervous systems and other miscellaneous mechanisms of action Marine Biotechnology 6 2004 37 52
37. 13C-NMR assignments Journal of Natural Products 51 5 1988 884 892
38. C. Moquin-Pattey, and M. Guyot Grossularine-1 and grossularine-2, cytotoxic α-carbolines from the tunicate: Dendrodoa grossularia Tetrahedron 45 11 1989 3445 3450
39. M.S. Morales-Rios, O.R. Suarez-Castillo, J.J. Trujillo-Serrato, and P. Joseph-Nathan Total syntheses of five indole alkaloids from the marine bryozoan Flustra foliacea Journal of Organic Chemistry 66 2001 1186 1192
40. Y. Nakao, B.K.S. Yeung, W.Y. Yoshida, P.J. Scheuer, and M. Kelly-Borges Kapakahine B: a cyclic hexapeptide with an α-carboline ring system from the marine sponge Cribrochalina olemda Journal of American Chemical Society 117 1995 8271 8272
41. D.J. Newman, G.M. Cragg, and K.M. Snader The influence of natural products upon drug discovery Natural Products Reports 17 2000 215 234
42. S.W. Pelletier Alkaloids: chemical and biological perspectives 4 1986 275 330
43. G.R. Pettit, R. Tan, D.L. Herald, R.L. Cerny, and M.D. Williams Antineoplastic agents.277. Isolation and structure of phakellistatin 3 and isophakellistatin 3 from a republic of Comoros marine sponge Journal of Organic Chemistry 59 7 1994 1593 1595
44. K.L. Rinehart, J. Kobayashi, G.C. Harbour, R.G. Hughes, S.A. Mizsak, and T.A. Scahill Eudistomins C, E, K and L, potent antiviral compounds containing a novel oxathiazepine ring from Caribbean tunicate Eudistoma olivaceum Journal of American Chemical Society 106 1984 1524 1526
45. K.L. Rinehart, J. Kobayashi, G.C. Harbour, J. Gilmore, M. Mascal, T.G. Holt, L.S. Shield, and F. Lafargue Eudistomins A-Q, β-carbolines from the antiviral Caribbean tunicate Eudistoma olivaceum Journal of American Chemical Society 109 1987 3378 3387
46. D.M. Roll, C.M. Ireland, H.S.M. Lu, and J. Clardy Fascaplysin, an unusual antimicrobial pigment from the marine sponge Fascaplysinopsis sp. Journal of Organic Chemistry 53 1988 3276 3278
47. S. Sakemi, and H.H. Sun Nortopsentins A, B, and C. Cytotoxic and antifungal imidazolediylbis [indoles] from the sponge Spongosorites ruetzleri Journal of Organic Chemistry 56 1991 4304 4307
48. H. Sato, M. Tsuda, K. Watanabe, and J. Kobayashi Rhopaladins A∼D, new indole alkaloids from marine tunicate Rhopalaea sp. Tetrahedron 54 1998 8687 8690
49. H. Shinonaga, H. Shigemori, and J. Kobayashi Konbamidin, a new indole alkaloid from the Okinawan marine sponge Ircinia sp. Journal of Natural Products 57 11 1994 1603 1605
50. S.W. Taylor, A.G. Craig, W.H. Fischer, M. Park, and R.I. Lehrer Styelin D, an extensively modified antimicrobial peptide from ascidian hemocytes Journal of Biological Chemistry 275 49 2000 38417 38426
51. S. Tsujii, K.L. Rinehart, S.P. Gunasekera, Y. Kashman, S.S. Cross, M.S. Lui, S.A. Pomponi, and M.C. Diaz Topsentin, bromotopsentin, and dihydrodeoxybromo-topsentin: antiviral and antitumor bis-(indolyl) imidazoles from Caribbean deep-sea sponges of the family halichondriidae Journal of Organic Chemistry 53 1988 5446 5453
52. A.E. Wright, S.A. Pomponi, S.S. Cross, and P. McCarthy A new bis (indole) alkaloid from a deep-water marine sponge of the genus Spongosorites Journal of Organic Chemistry 57 1992 4772 4775
53. C.G. Yang, G. Liu, and B. Jiang Preparing functional bis (indole) pyrazine by stepwise cross-coupling reactions: an efficient method to construct the skeleton of dragmacidin D Journal of Organic Chemistry 67 2002 9392 9396