Bioactive natural products from marine cyanobacteria for drug discovery

Phytochemistry

Volumn 68, Issue 7, 2007, Pages 954-979

  Tan, Lik Tong ^a  

^a NANYANG TECHNOLOGICAL UNIVERSITY   (Singapore)

Author keywords

Alkaloids; Drug discovery; Marine cyanobacteria; Polyketide nonribosomal polypeptide

Indexed keywords

ALKALOID; ANTINEOPLASTIC AGENT; BIOLOGICAL PRODUCT; LIPID; LIPOPROTEIN;

CHEMICAL STRUCTURE; CHEMISTRY; CYANOBACTERIUM; METABOLISM; REVIEW;

ALKALOIDS; ANTINEOPLASTIC AGENTS; BIOLOGICAL PRODUCTS; CYANOBACTERIA; LIPIDS; LIPOPROTEINS; MOLECULAR STRUCTURE;

CYANOBACTERIA; PROKARYOTA;

EID: 33947104489     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2007.01.012     Document Type: Review

References (96)

1. Ali M.A., Bates R.B., Crane Z.D., Dicus C.W., Gramme M.R., Hamel E., Marcischak J., Martinez D.S., McClure K.J., Nakkiew P., Pettit G.R., Stessman C.C., Sufi B.A., and Yarick G.V. Dolastatin 11 conformations, analogues and pharmacophore. Bioorg. Med. Chem. 13 (2005) 4138-4152
2. Andrianasolo E.H., Gross H., Goeger D., Musafija-Girt M., McPhail K., Leal R.M., Mooberry S.L., and Gerwick W.H. Isolation of swinholide A and related glycosylated derivatives from two field collections of marine cyanobacteria. Org. Lett. 7 (2005) 1375-1378
3. Appleton D.R., Sewell M.A., Berridge M.V., and Copp B.R. A new biologically active malyngamide from a New Zealand collection of the sea hare Bursatella leachii. J. Nat. Prod. 65 (2002) 630-631
4. Arda A., Rodriguez J., Nieto R.M., Bassarello C., Gomez-Paloma L., Bifulco G., and Jimenez C. NMR J-based analysis of nitrogen-containing moieties and application to dysithiazolamide, a new polychlorinated dipeptide from Dysidea sp. Tetrahedron 61 (2005) 10093-10098
5. Bai R., Verdier-Pinard P., Gangwar S., Stessman C.C., McClure K.J., Sausville E.A., Pettit G.R., Bates R.B., and Hamel E. Dolastatin 11, a marine depsipeptide, arrests cells at cytokinesis and induces hyperpolymerization of purified actin. Mol. Pharmacol. 59 (2001) 462-469
6. Beck Z.Q., Aldrich C.C., Magarvey N.A., Georg G.I., and Sherman D.H. Chemoenzymatic synthesis of cryptophycin/arenastatin natural products. Biochemistry 44 (2005) 13457-13466
7. Blumenthal K.M., and Seibert A.L. Voltage-gated sodium channel toxins: poisons, probes, and future promise. Cell Biochem. Biophys. 38 (2003) 215-238
8. Bunyajetpong S., Yoshida W.Y., Sitachitta N., and Kaya K. Trungapeptins A-C, cyclodepsipeptides from the marine cyanobacterium Lyngbya majuscula. J. Nat. Prod. 69 (2006) 1539-1542
9. Burns B.P., Seifert A., Goh F., Pomati F., Jungblut A., Serhat A., and Neilan B.A. Genetic potential for secondary metabolite production in stromatolite communities. FEMS Microbiol. Lett. 243 (2005) 293-301
10. Cetusic J.R., Green III F.R., Graupner P.R., and Oliver M.P. Total synthesis of hectochlorin. Org. Lett. 4 (2002) 1307-1310
11. Chen J.-H., and Forsyth C.J. Total synthesis of apratoxin A. J. Am. Chem. Soc. 125 (2003) 8734-8735
12. Chen J.-H., and Forsyth C.J. Synthesis of the apratoxin 2,4-disubstituted thiazoline via an intramolecular aza-wittig reaction. Org. Lett. 5 (2003) 1281-1283
13. Chen J.-H., and Forsyth C.J. Total synthesis of the marine cyanobacterial cyclodepsipeptide apratoxin A. Proc. Natl. Acad. Sci. USA 101 (2004) 12067-12072
14. Christiansen G., Dittmann E., Ordorika L.V., Rippka R., Herdman M., and Borner T. Nonribosomal peptide synthetase genes occur in most cyanobacterial genera as evidenced by their distribution in axenic strains of the PCC. Arch. Microbiol. 176 (2001) 452-458
15. Copp J.N., and Neilan B.A. The phosphopantetheinyl transferase superfamily: phylogenetic analysis and functional implications in cyanobacteria. Appl. Environ. Microbiol. 72 (2006) 2298-2305
16. Cruz-Rivera E., and Paul V.J. Chemical deterrence of a cyanobacterial metabolite against generalized and specialized grazers. J. Chem. Ecol. 33 (2007) 213-217
17. Davies-Coleman M., Dzeha T.M., Gray C.A., Hess S., Pannell L.K., Hendricks D.T., and Arendse C.E. Isolation of homodolastatin 16, a new cyclic depsipeptide from a Kenyan collection of Lyngbya majuscula. J. Nat. Prod. 66 (2003) 712-715
18. Davies I.R., Cheeseman M., Niyadurupola D.G., and Bull S.D. An efficient synthesis of semiplenamide C. Tetrahedron Lett. 46 (2005) 5547-5549
19. Dittmann E., Neilan B.A., and Borner T. Molecular biology of peptide and polyketide biosynthesis in cyanobacteria. Appl. Microbiol. Biotechnol. 57 (2001) 467-473
20. Doi T., Numajiri Y., Munakata A., and Takahashi T. Total synthesis of apratoxin A. Org. Lett. 8 (2006) 531-534
21. Donia M.S., Hathaway B.J., Sudek S., Haygood M.G., Rosovitz M.J., Ravel J., and Schmidt E.W. Natural combinatorial peptide libraries in cyanobacterial symbionts of marine ascidians. Nat. Chem. Biol. 2 (2006) 729-735
22. Edwards D.J., Marquez B.L., Nogle L.M., McPhail K., Goeger D.E., Roberts M.A., and Gerwick W.H. Structure and biosynthesis of the jamaicamides, new mixed polyketide-peptide neurotoxins from the marine cyanobacterium Lyngbya majuscula. Chem. Biol. 11 (2004) 817-833
23. Ehrenreich I.M., Waterbury J.B., and Webb E.A. Distribution and diversity of natural product genes in marine and freshwater cyanobacterial cultures and genomes. Appl. Environ. Microbiol. 71 (2005) 7401-7413
24. Flatt P.M., Gautschi J.T., Thacker R.W., Musafija-Girt M., Crews P., and Gerwick W.H. Identification of the cellular site of polychlorinated peptide biosynthesis in the marine sponge Dysidea (Lamellodysidea) herbacea and symbiotic cyanobacterium Oscillatoria spongeliae by CARD-FISH analysis. Mar. Biol. 147 (2005) 761-774
25. Flatt P.M., O'Connell S.J., McPhail K.L., Zeller G., Willis C.L., Sherman D.H., and Gerwick W.H. Characterization of the initial enzymatic steps of barbamide biosynthesis. J. Nat. Prod. 69 (2006) 938-944
26. Galonic D.P., Vaillancourt F.H., and Walsh C.T. Halogenation of unactivated carbon centers in natural product biosynthesis: trichlorination of leucine during barbamide biosynthesis. J. Am. Chem. Soc. 128 (2006) 3900-3901
27. Gerwick W.H., Tan L.T., and Sitachitta N. Nitrogen-containing metabolites from marine cyanobacteria. In: Cordell G.A. (Ed). The Alkaloids: Chemistry and Biology vol. 57 (2001), Academic Press, San Diego 75-184
28. Gu L., Jia J., Liu H., Hakansson K., Gerwick W.H., and Sherman D.H. Metabolic coupling of dehydration and decarboxylation in the curacin A pathway: functional identification of a mechanistically diverse enzyme pair. J. Am. Chem. Soc. 128 (2006) 9014-9015
29. Han B., McPhail K.L., Ligresti A., Di Marzo V., and Gerwick W.H. Semiplenamides A-G, fatty acid amides from a Papua New Guinea collection of the marine cyanobacterium Lyngbya semiplena. J. Nat. Prod. 66 (2003) 1364-1368
30. Han B., Goeger D., Maier C.S., and Gerwick W.H. The wewakpeptins, cyclic depsipeptides from a Papua New Guinea collection of the marine cyanobacterium Lyngbya semiplena. J. Org. Chem. 70 (2005) 3133-3139
31. Han B., McPhail K.L., Gross H., Goeger D.E., Mooberry S.L., and Gerwick W.H. Isolation and structure of five lyngbyabellin derivatives from a Papua New Guinea collection of the marine cyanoabacterium Lyngbya majuscula. Tetrahedron 61 (2005) 11723-11729
32. Han B., Gross H., Goeger D.E., Mooberry S.L., and Gerwick W.H. Aurilides B and C, cancer cell toxins from a Papua New Guinea collection of the marine cyanobacterium Lyngbya majuscula. J. Nat. Prod. 69 (2006) 572-575
33. Harrigan G.G., Goetz G.H., Luesch H., Yang S., and Likos J. Dysideaprolines A-F and barbaleucamides A-B, novel polychlorinated compounds from a Dysidea species. J. Nat. Prod. 64 (2001) 1133-1138
34. Horgen F.D., Kazmierski E.B., Westenburg H.E., Yoshida W.Y., and Scheuer P.J. Malevamide D: isolation and structure determination of an isodolastatin H analogue from the marine cyanobacterium Symploca hydnoides. J. Nat. Prod. 65 (2002) 487-491
35. Jordan M.A., and Wilson L. Microtubules and actin filaments: dynamic targets for cancer chemotherapy. Curr. Opin. Cell Biol. 10 (1998) 123-130
36. Kimura J., Takada Y., Inayoshi T., Nakao Y., Goetz G., Yoshida W.Y., and Scheuer P.J. Kulokekahilide-1, a cytotoxic depsipeptide from the cephalaspidean mollusk Philinopsis speciosa. J. Org. Chem. 67 (2002) 1760-1767
37. Li W.I., Berman F.W., Okino T., Yokokawa F., Shioiri T., Gerwick W.H., and Murray T.F. Antillatoxin is a marine cyanobacterial toxin that potently activates voltage-gated sodium channels. Proc. Natl. Acad. Sci. USA 98 (2001) 7599-7604
38. Luesch H., Pangilinan R., Yoshida W.Y., Moore R.E., and Paul V.J. Pitipeptolides A and B, new cyclodepsipeptides from the marine cyanobacterium Lyngbya majuscula. J. Nat. Prod. 64 (2001) 304-307
39. Luesch H., Yoshida W.Y., Moore R.E., Paul V.J., and Corbett T.H. Total structure determination of apratoxin A, a potent novel cytotoxin from the marine cyanobacterium Lyngbya majuscula. J. Am. Chem. Soc. 123 (2001) 5418-5423
40. Luesch H., Yoshida W.Y., Moore R.E., Paul V.J., Mooberry S.L., and Corbett T.H. Symplostatin 3, a new dolastatin 10 analogue from the marine cyanobacterium Symploca sp. VP452. J. Nat. Prod. 65 (2002) 16-20
41. Luesch H., Yoshida W.Y., Moore R.E., and Paul V.J. Structurally diverse new alkaloids from Palauan collections of the apratoxin-producing marine cyanobacterium Lyngbya sp. Tetrahedron 58 (2002) 7959-7966
42. Luesch H., Harrigan G.G., Goetz G., and Horgen F.D. The cyanobacterial origin of potent anticancer agents originally isolated from sea hares. Curr. Med. Chem. 9 (2002) 1791-1806
43. Luesch H., Williams P.G., Yoshida W.Y., Moore R.E., and Paul V.J. Ulongamides A-F, new β-amino acid-containing cyclodepsipeptides from Palauan collections of the marine cyanobacterium Lyngbya sp. J. Nat. Prod. 65 (2002) 996-1000
44. Luesch H., Yoshida W.Y., Moore R.E., and Paul V.J. New apratoxins of marine cyanobacterial origin from Guam and Palau. Bioorg. Med. Chem. 10 (2002) 1973-1978
45. Luesch H., Chanda S.K., Raya R.M., DeJesus P.D., Orth A.P., Walker J.R., Belmonte J.C.I., and Schultz P.G. A functional genomic approach to the mode of action of apratoxin A. Nat. Chem. Biol. 2 (2006) 158-167
46. MacMillan J., Ernst-Russell M.A., de Ropp J.S., and Molinski T.F. Lobocyclamides A-C, lipopeptides from a cryptic cyanobacterial mat containing Lyngbya confervoides. J. Org. Chem. 67 (2002) 8210-8215
47. Ma D.-W., Zou B., Cai G.-R., Hu X.-Y., and Liu J.O. Total synthesis of the cyclodepsipeptide apratoxin A and its analogues and assessment of their biological activities. Chemistry 12 (2006) 7615-7626
48. Marquez B.L., Watts K.S., Yokochi A., Roberts M.A., Verdier-Pinard P., Jimenez J.I., Hamel E., Scheuer P.J., and Gerwick W.H. Structure and absolute stereochemistry of hectochlorin, a potent stimulator of actin assembly. J. Nat. Prod. 65 (2002) 866-871
49. McPhail K.L., and Gerwick W.H. Three new malyngamides from a Pupua New Guinea collection of the marine cyanobacterium Lyngbya majuscula. J. Nat. Prod. 66 (2003) 132-135
50. Mita A.C., Hammond L.A., Bonate P.L., Weiss G., McCreery H., Syed S., Garrison M., Chu Q.S., DeBono J.S., Jones C.B., Weitman S., and Rowinsky E.K. Phase I and pharmacokinetic study of tasidotin hydrochloride (ILX651), a third-generation dolastatin-15 analogues, administered weekly for 3 weeks every 28 days in patients with advanced solid tumors. Clin. Cancer Res. 12 (2006) 5207-5215
51. Nakao Y., Yoshida W.Y., Takada Y., Kimura J., Yang L., Mooberry S.L., and Scheuer P.J. Kulokekahilide-2, a cytotoxic depsipeptide from a cephalaspidean mollusk Philinopsis speciosa. J. Nat. Prod. 67 (2004) 1332-1340
52. Nogle L.M., and Gerwick W.H. Somocystinamide A, a novel cytotoxic disulfide dimer from a Fijian marine cyanobacterial mixed assemblage. Org. Lett. 4 (2002) 1095-1098
53. Nogle L.M., and Gerwick W.H. Isolation of four new cyclic depsipeptides, antanapeptins A-D, and dolastatin 16 from a Madagascan collection of Lyngbya majuscula. J. Nat. Prod. 65 (2002) 21-24
54. Nogle L., and Gerwick W.H. Diverse secondary metabolites from a Puerto Rican collection of Lyngbya majuscula. J. Nat. Prod. 66 (2003) 217-220
55. Nogle L.M., Okino T., and Gerwick W.H. Antillatoxin B, a neurotoxic lipopeptide from the marine cyanobacterium Lyngbya majuscula. J. Nat. Prod. 64 (2001) 983-985
56. Nogle L.M., Williamson R.T., and Gerwick W.H. Somamides A and B, two new depsipeptide analogues of dolastatin 13 from a Fijian cyanobacterial assemblage of Lyngbya majuscula and Schizothrix species. J. Nat. Prod. 64 (2001) 716-719
57. Nogle L.M., Marquez B.L., and Gerwick W.H. Wewakazole, a novel cyclic dodecapeptide from a Papua New Guinea Lyngbya majuscula. Org. Lett. 5 (2003) 3-6
58. Olaizola M. Commercial development of microalgal biotechnology: from the test tube to the marketplace. Biomol. Eng. 20 (2003) 459-466
59. Orsini M.A., Pannell L.K., and Erickson K.L. Polychorinated acetamides from the cyanobacterium Microcoleus lyngbyaceus. J. Nat. Prod. 64 (2001) 572-577
60. Plaza A., and Bewley C.A. Largamides A-H, unusual cyclic peptides from the marine cyanobacterium Oscillatoria sp. J. Org. Chem. 71 (2006) 6898-6907
61. Ramaswamy A.V., Flatt P.M., Edwards D.J., Simmons T.L., Han B., and Gerwick W.H. The secondary metabolites and biosynthetic gene clusters of marine cyanobacteria. Applications in biotechnology. In: Proksch P., and Muller W.E.G. (Eds). Frontiers in Marine Biotechnology (2006), Horizon Bioscience 175-224
62. Ridley C.P., Bergquist P.R., Harper M.K., Faulkner D.J., Hooper J.N.A., and Haygood M.G. Speciation and biosynthetic variation in four dictyoceratid sponges and their cyanobacterial symbiont, Oscillatoria spongeliae. Chem. Biol. 12 (2005) 397-406
63. Schmidt E.W., Sudek S., and Haygood M.G. Genetic evidence supports secondary metabolic diversity in Prochloron spp., the cyanobacterial symbiont of a tropical ascidian. J. Nat. Prod. 67 (2004) 1341-1345
64. Schmidt E.W., Nelson J.T., Rasko D.A., Sudek S., Eisen J.A., Haygood M.G., and Ravel J. Patellamide A and C biosynthesis by a microcin-like pathway in Prochloron didemni, the cyanobacterial symbiont of Lissoclinum patella. Proc. Natl. Acad. Sci. USA 102 (2005) 7315-7320
65. Schwarzer D., Finking R., and Marahiel M.A. Nonribosomal peptides: from genes to products. Nat. Prod. Rep. 20 (2003) 275-287
66. Seng, A.W.P., Ong, Y.Z., Lee, W.Y., Lee, P.P.F., Lim, S.C., Tan, K.S., Tan, L.T., 2007. Biomedical potential of intertidal marine organisms from Singapore. Mar. Biotechnol. (submitted).
67. Simmons T.L., McPhail K.L., Ortega-Barria E., Mooberry S.L., and Gerwick W.H. Belamide A, a new antimitotic tetrapeptide from a Panamanian cyanobacterium. Tetrahedron Lett. 47 (2006) 3387-3390
68. Stapleton B.L., Cameron G.M., and Garson M.J. New chlorinated peptides from the tropical marine sponge Dysidea sp. Tetrahedron 57 (2001) 4603-4607
69. Steer D.L., Lew R.A., Perlmutter P., Smith A.I., and Aguilar M.-I. β-Amino acids: versatile peptidomimetics. Curr. Med. Chem. 9 (2002) 811-822
70. Sudek S., Haygood M.G., Youssef D.T.A., and Schmidt E.W. Structure of trichamide, a cyclic peptide from the bloom-forming cyanobacterium Trichodesmium erythraeum, predicted from the genome sequence. Appl. Environ. Microbiol. 72 (2006) 4382-4387
71. Suenaga K., Mutou T., Shibata T., Itoh T., Fujita T., Takada N., Hayamizu K., Takagi M., Irifune T., Kigoshi H., and Yamada K. Aurilide, a cytotoxic depsipeptide from the sea hare Dolabella auricularia: isolation, structure determination, synthesis, and biological activity. Tetrahedron 60 (2004) 8509-8527
72. Suntornchashwej S., Chaichit N., Isobe M., and Suwanborirux K. Hectochlorin and morpholine derivatives from the Thai sea hare Bursatella leachii. J. Nat. Prod. 68 (2005) 951-955
73. Takahashi T., Nagamiya H., Doi T., Griffiths P.G., and Bray A.M. Solid phase library synthesis of cyclic depsipeptides: aurilide and aurilide analogues. J. Comb. Chem. 5 (2003) 414-428
74. Tan L.T., Marquez B.L., and Gerwick W.H. Lyngbouilloside, a novel glycosidic macrolide from the marine cyanobacterium Lyngbya bouillonii. J. Nat. Prod. 65 (2002) 925-928
75. Tan L.T., Sitachitta N., and Gerwick W.H. The guineamides, novel cyclic depsipeptides from a Papua New Guinea collection of the marine cyanobacterium Lyngbya majuscula. J. Nat. Prod. 66 (2003) 764-771
76. Teruya T., Kobayashi K., Suenaga K., and Kigoshi H. Phormidinines A and B, novel 2-alkylpyridine alkaloids from the cyanobacterium Phormidium sp. Tetrahedron Lett. 46 (2005) 4001-4003
77. Thacker R.W., and Paul V.J. Morphological, chemical, and genetic diversity of tropical marine cyanobacteria Lyngbya spp. and Symploca spp. (Oscillatoriales). Appl. Environ. Microbiol. 70 (2004) 3305-3312
78. Vaillancourt F.H., Yeh E., Vosburg D.A., O'Connor S.E., and Walsh C.T. Cryptic chlorination by a non-haem iron enzyme during cyclopropyl amino acid biosynthesis. Nature 436 (2005) 1191-1194
79. 2-dependent halogenase. Proc. Natl. Acad. Sci. USA 102 (2005) 10111-10116
80. Vaillancourt F.H., Yeh E., Vosburg D.A., Garneau-Tsodikova S., and Walsh C.T. Nature's inventory of halogenation catalysis: oxidative strategies predominate. Chem. Rev. 106 (2006) 3364-3378
81. Watanabe J., Minami M., and Kobayashi M. Antitumor activity of TZT-1027 (soblidotin). Anticancer Res. 26 (2006) 1973-1981
82. Williams P.G., Luesch H., Yoshida W.Y., Moore R.E., and Paul V.J. Tasiamide, a cytotoxic peptide from the marine cyanobacterium Symploca sp. J. Nat. Prod. 65 (2002) 1336-1339
83. Williams P.G., Yoshida W.Y., Moore R.E., and Paul V.J. Isolation and structure determination of obyanamide, a novel cytotoxic cyclic depsipeptides from the marine cyanobacterium Lyngbya confervoides. J. Nat. Prod. 65 (2002) 29-31
84. Williams P.G., Luesch H., Yoshida W.Y., Moore R.E., and Paul V.J. Continuing studies on the cyanobacterium Lyngbya sp.: isolation and structure determination of 15-norlyngbyapeptin A and lyngbyabellin D. J. Nat. Prod. 66 (2003) 595-598
85. Williams P.G., Yoshida W.Y., Moore R.E., and Paul V.J. The isolation and structure elucidation of tasiamide B, a 4-amino-3-hydroxy-5-phenylpentanoic acid containing peptide from the marine cyanobacterium Symploca sp. J. Nat. Prod. 66 (2003) 1006-1009
86. Williams P.G., Yoshida W.Y., Quon M.K., Moore R.E., and Paul V.J. Ulongapeptin, a cytotoxic cyclic depsipeptide from a Palauan marine cyanobacterium Lyngbya species. J. Nat. Prod. 66 (2003) 651-654
87. Williams P.G., Moore R.E., and Paul V.J. Isolation and structure determination of lyngbyastatin 3, a lynbyastatin1 homologue from the marine cyanobacterium Lyngbya majuscula. Determination of the configuration of the 4-amino-2,2-dimethyl-3-oxopentanoic acid unit in majusculamide C, dolastatin 12, lyngbyastatin 1, and lyngbyastatin 3 from cyanobacteria. J. Nat. Prod. 66 (2003) 1356-1363
88. Williams P.G., Yoshida W.Y., Quon M.K., Moore R.E., and Paul V.J. The structure of palau'amide, a potent cytotoxin from a species of the marine cyanobacterium Lyngbya. J. Nat. Prod. 66 (2003) 1545-1549
89. Williams P.G., Yoshida W.Y., Moore R.E., and Paul V.J. Tasipeptins A and B: new cytotoxic depsipeptides from the marine cyanobacterium Symploca sp. J. Nat. Prod. 66 (2003) 620-624
90. Williams P.G., Yoshida W.Y., Moore R.E., and Paul V.J. Micromide and guamamide: cytotoxic alkaloids from a species of the marine cyanobacterium Symploca. J. Nat. Prod. 67 (2004) 49-53
91. Williamson R.T., Singh I.P., and Gerwick W.H. Taveuniamides: new chlorinated toxins from a mixed assemblage of marine cyanobacteria. Tetrahedron 60 (2004) 7025-7033
92. Wipf P., Reeves J.T., Balachandran R., and Day B.W. Synthesis and biological evaluation of structurally highly modified analogues of the antimitotic natural product curacin A. J. Med. Chem. 45 (2002) 1901-1917
93. Yokokawa F., and Shioiri T. Total synthesis of somamide A, an Ahp (3-amino-6-hydroxy-2-piperidone)-containing cyclic depsipeptide. Tetrahedron Lett. 43 (2002) 8673-8677
94. Yokokawa F., Sameshima H., and Shioiri T. Total synthesis of lyngbyabellin A, a potent cytotoxic metabolite from the marine cyanobacterium Lyngbya majuscula. Tetrehedron Lett. 42 (2001) 4171-4174
95. Yokokawa F., Sameshima H., Katagiri D., Aoyama T., and Shioiri T. Total synthesis of lyngbyabellins A and B, potent cytotoxic lipopeptides from the marine cyanobacterium Lyngbya majuscula. Tetrahedron 58 (2002) 9445-9458
96. Zou B., Wei J.-J., Cai G.-R., and Ma D.-W. Synthesis of an oxazoline analogue of apratoxin A. Org. Lett. 5 (2003) 3503-3506