Secondary metabolites from marine microorganisms

Anais da Academia Brasileira de Ciencias

Volumn 74, Issue 1, 2002, Pages 151-170

  Kelecom, Alphonse ^a  

^a FLUMINENSE FEDERAL UNIVERSITY   (Brazil)

Author keywords

Acetogenins; Alkaloids; Bacteria; Biological activities; Despsipeptides; Fungi; Terpenoids

Indexed keywords

ALGAE; BACTERIA (MICROORGANISMS); COELENTERATA; CRUSTACEA; FUNGI; INVERTEBRATA; MOLLUSCA; UROCHORDATA;

BIOLOGICAL FACTOR; SEA WATER;

ALGA; ANIMAL; BACTERIUM; CHEMISTRY; FISH; FUNGUS; INVERTEBRATE; METABOLISM; MICROBIOLOGY; REVIEW; SEDIMENT;

ALGAE; ANIMALS; BACTERIA; BIOLOGICAL FACTORS; FISHES; FUNGI; GEOLOGIC SEDIMENTS; INVERTEBRATES; SEAWATER;

EID: 0036514501     PISSN: 00013765     EISSN: None     Source Type: Journal    
DOI: 10.1590/S0001-37652002000100012     Document Type: Article

References (80)

1. BERNAN VS, GREENSTEIN, M AND MAISE, WM. 1997. Marine microorganisms as a source of new natural products. Adv Appl Microbiol 43: 57-90.
2. BERQUIST PR AND WELLS RJ. 1983. Chemotaxonomy of the Porifera: the development and current status of the field. In: Marine Natural Products: Chemical and Biological Perspectives, SCHEUER, PJ (editor), Academic Press, vol. V, pp. 17-22.
3. 5. Biochem J 50: 168-174.
4. CARMELY S AND KASHMAN Y. 1985. Structure of swinholide-A, a new macrolide from the marine sponge Theonella swinhoei. Tetrahedron Lett 26: 511-514.
5. CHARLES C, BRAEKMAN JC, DALOZE D, TURSCH B, DECLERCQ JP, GERMAIN G AND VAN MEERSSCHE M. 1978. Chemical studies of marine invertebrates XXXIV. Herba-dysidolide and herbasolide, two unusual sesquiterpenes from the sponge Dysidea herbacea. Bull Soc Chim Belg 87: 481-486.
6. CHEN YS. 1960. Studies of the metabolic products of Rosellinia necatrix I. Isolation and characterization of several physiologically active neutral substances. Bull Agr Chem Soc Jpn 24: 372-381.
7. CRONAN JR JM AND CARDELLINA II JH. 1994. A novel δ-lactam from the sponge Tedania ignis. Nat Prod Letters 5: 85-88.
8. DAVIDSON BS. 1995. New dimensions in natural products research: cultured marine microorganisms. Curr Opin Biotechnol 6: 284-291.
9. ELYAKOV GB. 1998. Horizons in marine bioorganic chemistry, in: IX Int. Symposium on Marine Natural Products, Symposium Proceed., Townsville, Australia, Abstract OR-28.
10. ELYAKOV GB, KUZNETSOVA T, MIKHAILOV VV, MALTSEV II, VOINOV VG AND FEDOREYEV SA. 1991. Brominated diphenyl ethers from a bacterium associated with the sponge Dysidea sp. Experientia 47: 632-633.
11. ERICKSON KL AND WELLS RJ. 1982. New polychlorinated metabolites from a Barrier Reef collection of the sponge Dysidea herbacea. Aust J Chem 35: 31-38.
12. FATTORUSSO E, MINALE L, SODANO G, MOODY K AND THOMSON RH. 1970. Aerothionin a tetrabromo-compound from Aplysina aerophoba and Verongia thiona. Chem Commun 752-753.
13. FAULKNER DJ. 1984-1999. Marine Natural Products, Nat Prod Rep 1: 251-280, 1: 551-598, 3: 1-33, 4: 539-576, 5: 613-663, 7: 269-309, 8: 97-147, 9: 323-364, 10: 497-539, 11: 355-394, 12: 223-269, 13: 75-125, 14: 259-302, 15: 113-158, 16: 155-198.
14. FAULKNER DJ. 1984-1999. Marine Natural Products, Nat Prod Rep 1: 251-280, 1: 551-598, 3: 1-33, 4: 539-576, 5: 613-663, 7: 269-309, 8: 97-147, 9: 323-364, 10: 497-539, 11: 355-394, 12: 223-269, 13: 75-125, 14: 259-302, 15: 113-158, 16: 155-198.
15. FAULKNER DJ. 1984-1999. Marine Natural Products, Nat Prod Rep 1: 251-280, 1: 551-598, 3: 1-33, 4: 539-576, 5: 613-663, 7: 269-309, 8: 97-147, 9: 323-364, 10: 497-539, 11: 355-394, 12: 223-269, 13: 75-125, 14: 259-302, 15: 113-158, 16: 155-198.
16. FAULKNER DJ. 1984-1999. Marine Natural Products, Nat Prod Rep 1: 251-280, 1: 551-598, 3: 1-33, 4: 539-576, 5: 613-663, 7: 269-309, 8: 97-147, 9: 323-364, 10: 497-539, 11: 355-394, 12: 223-269, 13: 75-125, 14: 259-302, 15: 113-158, 16: 155-198.
17. FAULKNER DJ. 1984-1999. Marine Natural Products, Nat Prod Rep 1: 251-280, 1: 551-598, 3: 1-33, 4: 539-576, 5: 613-663, 7: 269-309, 8: 97-147, 9: 323-364, 10: 497-539, 11: 355-394, 12: 223-269, 13: 75-125, 14: 259-302, 15: 113-158, 16: 155-198.
18. FAULKNER DJ. 1984-1999. Marine Natural Products, Nat Prod Rep 1: 251-280, 1: 551-598, 3: 1-33, 4: 539-576, 5: 613-663, 7: 269-309, 8: 97-147, 9: 323-364, 10: 497-539, 11: 355-394, 12: 223-269, 13: 75-125, 14: 259-302, 15: 113-158, 16: 155-198.
19. FAULKNER DJ. 1984-1999. Marine Natural Products, Nat Prod Rep 1: 251-280, 1: 551-598, 3: 1-33, 4: 539-576, 5: 613-663, 7: 269-309, 8: 97-147, 9: 323-364, 10: 497-539, 11: 355-394, 12: 223-269, 13: 75-125, 14: 259-302, 15: 113-158, 16: 155-198.
20. FAULKNER DJ. 1984-1999. Marine Natural Products, Nat Prod Rep 1: 251-280, 1: 551-598, 3: 1-33, 4: 539-576, 5: 613-663, 7: 269-309, 8: 97-147, 9: 323-364, 10: 497-539, 11: 355-394, 12: 223-269, 13: 75-125, 14: 259-302, 15: 113-158, 16: 155-198.
21. FAULKNER DJ. 1984-1999. Marine Natural Products, Nat Prod Rep 1: 251-280, 1: 551-598, 3: 1-33, 4: 539-576, 5: 613-663, 7: 269-309, 8: 97-147, 9: 323-364, 10: 497-539, 11: 355-394, 12: 223-269, 13: 75-125, 14: 259-302, 15: 113-158, 16: 155-198.
22. FAULKNER DJ. 1984-1999. Marine Natural Products, Nat Prod Rep 1: 251-280, 1: 551-598, 3: 1-33, 4: 539-576, 5: 613-663, 7: 269-309, 8: 97-147, 9: 323-364, 10: 497-539, 11: 355-394, 12: 223-269, 13: 75-125, 14: 259-302, 15: 113-158, 16: 155-198.
23. FAULKNER DJ. 1984-1999. Marine Natural Products, Nat Prod Rep 1: 251-280, 1: 551-598, 3: 1-33, 4: 539-576, 5: 613-663, 7: 269-309, 8: 97-147, 9: 323-364, 10: 497-539, 11: 355-394, 12: 223-269, 13: 75-125, 14: 259-302, 15: 113-158, 16: 155-198.
24. FAULKNER DJ. 1984-1999. Marine Natural Products, Nat Prod Rep 1: 251-280, 1: 551-598, 3: 1-33, 4: 539-576, 5: 613-663, 7: 269-309, 8: 97-147, 9: 323-364, 10: 497-539, 11: 355-394, 12: 223-269, 13: 75-125, 14: 259-302, 15: 113-158, 16: 155-198.
25. FAULKNER DJ. 1984-1999. Marine Natural Products, Nat Prod Rep 1: 251-280, 1: 551-598, 3: 1-33, 4: 539-576, 5: 613-663, 7: 269-309, 8: 97-147, 9: 323-364, 10: 497-539, 11: 355-394, 12: 223-269, 13: 75-125, 14: 259-302, 15: 113-158, 16: 155-198.
26. FAULKNER DJ. 1984-1999. Marine Natural Products, Nat Prod Rep 1: 251-280, 1: 551-598, 3: 1-33, 4: 539-576, 5: 613-663, 7: 269-309, 8: 97-147, 9: 323-364, 10: 497-539, 11: 355-394, 12: 223-269, 13: 75-125, 14: 259-302, 15: 113-158, 16: 155-198.
27. FAULKNER DJ. 1984-1999. Marine Natural Products, Nat Prod Rep 1: 251-280, 1: 551-598, 3: 1-33, 4: 539-576, 5: 613-663, 7: 269-309, 8: 97-147, 9: 323-364, 10: 497-539, 11: 355-394, 12: 223-269, 13: 75-125, 14: 259-302, 15: 113-158, 16: 155-198.
28. FAULKNER DJ, HARPER MK, HAYGOOD MG, SALOMON CE AND SCHMIDT EW. 2000. Symbiotic bacteria in sponges: sources of bioactive substances. In: FUSETANI N (Ed.), Drugs from the Sea, Basel: Karger, p. 107-119.
29. FENICAL W. 1993. Chemical studies of marine bacteria: developing a new resource. Chem Rev 93: 1673-1683.
30. FENICAL W, JENSEN P, TAPIOLAS D, GUSTAFSON K, ROMAN M AND PATHIRANA C. 1989. Natural products chemistry of sediment-derived marine bacteria. Proceed. VI Int. Symp. Marine Natural Products, Dakar, Senegal.
31. FRINCKE JM AND FAULKNER DJ. 1982. Antimicrobial metabolites of the sponge Reniera sp. J Am Chem Soc 104: 265-269.
32. FUJIKI H AND SUGANUMA M. 1993. Tumor promotion by inhibitors of protein phosphatases 1 and 2A: the okadaic class of compounds. Adv Cancer Res 61: 143-194.
33. FUKUMI H, KURIHARA H, HATA T, TAMURA C, MISHIMA H, KUBO A AND ARAI T. 1977. Mimosamycin, a novel antibiotic produced by Streptomyces lavendulae n 314: structure and synthesis. Tetrahedron Lett, 3825-3828.
34. FUSETANI N. 2000. Introduction. In: FUSETANI N (Ed.), Drugs from the Sea, Basel: Karger, p. 1-5.
35. GIL-TURNES MS, HAY ME AND FENICAL W. 1989. Symbiotic marine bacteria chemically defend crustacean embryos from a pathogenic fungus. Science 246: 116-118.
36. HALSTEAD BW. 1965. Poisonous and Venomous Marine Animals of the World, vol. I, chap. 1, pp. 1-155, US Government Printing Office, Washington DC.
37. JENSEN PR AND FENICAL W. 1994. Strategies for the discovery of secondary metabolites from marine bacteria. Ann Rev Microbiol 48: 559-584.
38. JENSEN PR AND FENICAL W. 1996. Marine bacterial diversity as a resource for novel microbial products. J Ind Microbiol 17: 346-351.
39. JENSEN PR AND FENICAL W. 2000. Marine microorganisms and drug discovery: current status and future potential. In: FUSETANI N (Ed.), Drugs from the Sea, Basel: Karger, p. 6-29.
40. KAZLAUSKAS R, MURPHY PT AND WELLS RJ. 1978a. A diketopiperazine derived from trichloro-leucine from the sponge Dysidea herbacea. Tetrahedron Lett, 4945-4948.
41. KAZLAUSKAS R, MURPHY PT AND WELLS RJ. 1978b. A new sesquiterpene from the sponge Dysidea herbacea. Tetrahedron Lett, 4949-4950.
42. KELECOM A. 1997. Marine natural products in Brazil. Part 1. Isolation and structure determination. Ciên Cult - J Braz Ass Adv Sci 49: 321-330.
43. KELECOM A. 1999. Chemistry of Marine Natural Products: Yesterday, Today and Tomorrow. An Acad Bras Cienc 71: 249-263.
44. KELECOM A AND KANNENGIESSER GJ. 1979. Chemical Constituents of Verongia Sponges I - A Comparison Between Brazilian and Mediterranean Species. An Acad Bras Cienc 51: 633-637.
45. KIKUCHI T, MORI Y, YOKOI T, NAKAZAWA S, KURODA H, MASADA Y, KITAMURA K AND KURIYAMA K. 1983. Structure and absolute configuration of sargatriol, a new isoprenoid chromenol from a brown alga, Sargassum tortile C. Agardh. Chem Pharm Bull 31: 106-113.
46. KITAGAWA I, KOBAYASHI M, LEE NK, SHIBUYA H, KAWATA Y AND SAKIYAMA F. 1986. Structure of theonellapeptolide Id, anew bioactive peptolide from an Okinawan marine sponge, Theonella sp (Theonelliae). Chem Pharm Bull 34: 2664-2667.
47. KITAGAWA I, KOBAYASHI M, KATORI T, YAMASHITA M, TANAKA J, DOI M AND ISHIDA T. 1990. Absolute stereostructure of swinholide A, a potent cytotoxic macrolide from the Okinawan marine sponge Theonella swinhoei. J Am Chem Soc 112: 3710-3712.
48. KOBAYASHI J AND ISHIBASHI M. 1993. Bioactive metabolites of symbiotic marine micro-organisms. Chem Rev 93: 1753-1769.
49. KOBAYASHI M, AOKI S, SAKAI H, KIHARA N, SASAKI T AND KITAGAWA I. 1993. Altohyrtins B and C and 5-desacetylaltohyrtin A, potent cytotoxic macrolide congeners of altohyrtin A, from the Okinawan marine sponge Hvrtios altum. Chem Pharm Bull 41: 989-991.
50. KOBAYASHI M, OKAMOTO T, HAYASHI K, YOKOYAMA N, SASAKI T AND KITAGAWA I. 1994. Absolute configuration of C-4 of the manoalide family, biologically active sesterterpenes from the marine sponge Hyrtios erecta. Chem Pharm Bull 42: 265-270.
51. KODAIRA Y. 1961. Toxic substances to insects, produced by Aspergillus ochraceus and Oospora destructor. Agr Biol Chem 25: 261-262.
52. LIAAEN-JENSEN S. 1967. Recent advances in the chemistry of natural carotenoids. Pure Appl Chem 14: 227-244.
53. LIBERRA K AND LINDQUIST U. 1995. Marine fungi: aprolific source of biologically active natural products? Pharmazie 50: 583-588.
54. MACLEOD RA. 1965, The question of the existence of specific marine bacteria. Bacteriol Rev 29: 9-23.
55. MCKEE TC AND IRELAND CM. 1987. Cytotoxic and antimicrobial alkaloids from the Fijan sponge Xestospongia caycedoi. J Nat Prod 50: 754-756.
56. MIKI W, OTAKI N, YOKOVAMA A, IZUMIDA H AND SHIMIDZU N. 1994. Okadaxanthin, a novel C50-carotenoid from a bacterium, Pseudomonas sp. KK 10206C associated with a marine sponge, Halichondria okadai. Experientia 50: 684-686.
57. MINALE L, CIMINO G, DE STEFANO S AND SODANO G. 1976. Natural products from Porifera. Fort Chem Org Naturstoffe 33: 1-72.
58. MOODY K, THOMSON RH, FATTORUSSO E, MINALE L AND SODANO G. 1972. Aerothionin and homoaerothionin: two tetrabromo spirohexadienylisoxazoles from Verongia sponges. J Chem Soc Perkin I: 18-24.
59. MURAKAMI Y, OSHIMA Y AND YASUMOTO T. 1982. Identification of okadaic acid as a toxic component of a marine dinofiagellate Prorocentrum lima. Bull Jap Soc Sci Fish 48: 69-72.
60. NAKAMURA H, KOBAYASHI J'I, NAKAMURA Y, OHIZUMI Y, KONDO T AND HIRATA Y. 1986. Theonellamine B, a novel peptidal Na,K-ATPase inhibitor from an Okinawan marine sponge of the genus Theonella. Tetrahedron Lett 27: 4319-4322.
61. 13C spin-lattice relaxation measurements to determine the structure of a tetrabromo diphenyl ether from the sponge Dysidea herbacea. Tetrahedron Lett 21: 3801-3804.
62. NUMATA A, KANBARA S, TAKAHASHI C, FUJIKI R, YONEDA M, FUJITA E AND NABESHIMA Y. 1991. Cytotoxic activity of marine brown algae and cytotoxic principle of the brown alga Sargassum tortile. Chem Pharm Bull 39: 2129-2131.
63. PARAMESWARAN PS, NAIK CG AND HEGDE VR. 1997. Secondary metabolites from the sponge Tedania anhelans: isolation and characterization of twonovel pyrazole acids and other metabolites. J Nat Prod 60: 802-803.
64. PIETRA F. 1997. Secondary metabolites from marine microorganisms - bacteria, protozoa, algae and fungi - achievements and prospectives. Nat Prod Rep 14: 453-464.
65. SAKEMI S, ICHIBA T, KOHMOTO S, SAUCY G AND HIGA T. 1988. Isolation and structure elucidation of onnamide A, a new bioactive metabolite of a marine sponge, Theonella sp. J Am Chem Soc 110: 4851-4853.
66. SCHEUER PJ. 1973. Marine Natural Products, p. 38, Academic Press, NY and London.
67. SCHMITZ FJ, VANDERAH DJ, HOLLENBEAK KH, ENWALL CEL, GOPICHAND Y, SENGUPTA PK, HOSSAIN MB AND VAN DER HELM D. 1983. Metabolites from the marine sponge Tedania ignis. A new atisanediol and several known diketopiperazines. J Org Chem 48: 3941-3945.
68. SHIGEMORI H, BAE MA, YAZAWA K, SASAKI T AND KOBAYASHI J. 1992. Alteramida A, a new tetracyclic alkaloid from a bacterium Alteromonas sp associated with the marine sponge Halichondria okadai. J Org Chem 57: 4317-4320.
69. SILVA ED DE AND SCHEUER PJ. 1980. Manoalide, an antibiotic sesterterpenoid from the marine sponge Luffariella variabilis. Tetrahedron Lett 21: 1611-1614.
70. STIERLE AC, CARDELLINA II JH AND SINGLETON FL. 1988. A marine Micrococcus produces metabolites ascribed to the sponge Tedania ignis. Experientia 44: 1021.
71. TACHIBANA K, SCHEUER PJ, TSUKITANI Y, KIKUCHI H, VAN ENGEN D, CLARDY J, GOPICHAND Y AND SCHMITZ FJ. 1981. Okadaic acid, a cytotoxic polyether from two marine sponges of the genus Halichondria. J Am Chem Soc 103: 2469-2471.
72. TAKAHASHI C, NUMATA A, ITO Y, MATSUMURA E, MINOURA K, ETO H, SHINGU T, ITO T AND HASEGAWA T. 1994. Leptosins I and J, cytotoxic substances produced bt a Leptosphaerias sp. Physido-chemical properties and structures. J Antibiot 47: 1242-1249.
73. THOMPSON JE, BARROW KD AND FAULKNER DJ. 1983. Localization of two brominated metabolites, aerothionin and homoaerothionin, in spherulous cells of the marine sponge Aplysina fistularis (= Verongia thiona). Acta Zool 64: 199-210.
74. UEMURA D, TAKAHASHI K, YAMAMOTO T, KATAYAMA C, TANAKA J, OKUMURA Y AND HIRATA Y. 1985. Norhalichondrin A: an antitumor polyether macrolide from a marine sponge. J Am Chem Soc 107: 4796-4798.
75. UNSON MD AND FAULKNER DJ. 1993. Cyanobacterial symbiont biosynthesis of chlorinated metabolites from Dysidea herbacea (Porifera). Experientia 49: 349-353.
76. UTKINA NK, KAZANTSEVA MV AND DENISENKO VA. 1988. Brominated diphenyl ethers from the marine sponge Dysidea fragilis. Chem Nat Prod 23: 508-509 [translation of the paper published in Khim Prirod Soed (1987) no. 4, 603-605.
77. UTKINA NK, KAZANTSEVA MV AND DENISENKO VA. 1988. Brominated diphenyl ethers from the marine sponge Dysidea fragilis. Chem Nat Prod 23: 508-509 [translation of the paper published in Khim Prirod Soed (1987) no. 4, 603-605.
78. VAROGLU M, CORBETT TH, VALERIOTE FA AND CREWS P. 1997. Asperazine, a selective cytotoxic alkaloid from a sponge-derived culture of Aspergillus niger. J Org Chem 62: 7078-7079.
79. WALKER RP, THOMPSON JE AND FAULKNER DJ. 1985. Exudation of biologically active metabolites in the sponge Aplysina fistularis. II. Chemical evidences. Mar Biol 88: 27-32.
80. 2 and its acetate, methyl ester) in the gorgonian Plexaura homomalla. Tetrahedron Lett, 5185-5188.