Marine-derived metabolites of S-adenosylmethionine as templates for new anti-infectives

Marine Drugs

Volumn 7, Issue 3, 2009, Pages 401-434

  Sufrin, Janice R ^a   Finckbeiner, Steven ^a   Oliver, Colin M ^a  

^a ROSWELL PARK CANCER INSTITUTE   (United States)

Author keywords

Adenosylmethionine; Ethylene; Polyamines; Quorum sensing; Radical SAM

Indexed keywords

ACARNIDINE; ANTIINFECTIVE AGENT; BARBAMIDE; BRASSICASTEROL; CRAMBESCIDIN 800; CURACIN A; DECHLOROBARBARAMIDE; DRUG METABOLITE; ETHYLENE; GORGOSTEROL; ILIMAQUINONE; MUTASTEROL; N ACYLHOMOSERINE LACTONE; PENARAMIDE A; PETROBACTIN 1; PHOMOPSIDIN; POLYAMINE DERIVATIVE; PRUGOSENE A1; PSEUDOCERATIDINE; PTILOMYCALIN A; PUTRESCINE; S ADENOSYLMETHIONINE; SINULAMIDE; SORBICILLACTONE A; SORBICILLACTONE B; SPERMATINAMINE; SPERMIDINE; SPERMINE; SQUALAMINE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

BIOSYNTHESIS; DRUG DESIGN; DRUG STRUCTURE; HALOGENATION; MACROMOLECULE; MARINE SPECIES; METHYLATION; NONHUMAN; QUORUM SENSING; REVIEW;

EID: 70349493013     PISSN: None     EISSN: 16603397     Source Type: Journal    
DOI: 10.3390/md7030401     Document Type: Review

References (182)

1. Eustaquio, A.S.; Pojer, F.; Noe, J.P.; Moore, B.S. Discovery and Characterization of a Marine Bacterial SAM-Dependent Chlorinase. Nat. Chem. Biol. 2008, 4, 69-74.
2. Kotb, M.; Geller, A.M. Methionine Adenosyltransferase-Structure and Function. Pharmacol. Ther. 1993, 59, 125-143.
3. Iwig, D.F.; Booker, S.J. Insight into the Polar Reactivity of the Onium Chalcogen Analogues of S-Adenosyl-L-Methionine. Biochemistry 2004, 43, 13496-13509.
4. Fontecave, M.; Atta, M.; Mulliez, E. S-Adenosylmethionine: Nothing Goes to Waste. Trends Biochem. Sci. 2004, 29, 243-249.
5. Kagan, R.M.; Clarke, S. Widespread Occurrence of 3 Sequence Motifs in Diverse S-Adenosylmethionine-Dependent Methyltransferases Suggests a Common Structure for These Enzymes. Arch. Biochem. Biophys. 1994, 310, 417-427. (Pubitemid 24172687)
6. Deng, H.; O'Hagan, D. The Fluorinase, the Chlorinase and the Duf-62 Enzymes. Curr. Opin. Chem. Biol. 2008, 12, 582-592.
7. Hanzelka, B.L.; Greenberg, E.P. Quorum Sensing in Vibrio Fischeri: Evidence That S-Adenosylmethionine Is the Amino Acid Substrate for Autoinducer Synthesis. J. Bacteriol. 1996, 178, 5291-5294.
8. More, M.I.; Finger, L.D.; Stryker, J.L.; Fuqua, C.; Eberhard, A.; Winans, S.C. Enzymatic Synthesis of a Quorum-Sensing Autoinducer through Use of Defined Substrates. Science 1996, 272, 1655-1658.
9. Chen, X.; Schauder, S.; Potier, N.; Van Dorsselaer, A.; Pelczer, I.; Bassler, B.L.; Hughson, F.M. Structural Identification of a Bacterial Quorum-Sensing Signal Containing Boron. Nature 2002, 415, 545-549.
10. Sofia, H.J.; Chen, G.; Hetzler, B.G.; Reyes-Spindola, J.F.; Miller, N.E. Radical SAM, a Novel Protein Superfamily Linking Unresolved Steps in Familiar Biosynthetic Pathways with Radical Mechanisms: Functional Characterization Using New Analysis and Information Visualization Methods. Nucleic Acids Res. 2001, 29, 1097-1106.
11. Frey, P.A.; Hegeman, A.D.; Ruzicka, F.J. The Radical SAM Superfamily. Crit. Rev. Biochem. Mol. Biol. 2008, 43, 63-88.
12. Booker, S.J. Anaerobic Functionalization of Unactivated C-H Bonds. Curr. Opin. Chem. Biol. 2009, 13, 58-73.
13. O'Hagan, D.; Schaffrath, C.; Cobb, S.L.; Hamilton, J.T.G.; Murphy, C.D. Biosynthesis of an Organofluorine Molecule-a Fluorinase Enzyme Has Been Discovered that Catalyses Carbon-Fluorine Bond Formation. Nature 2002, 416, 279-279
14. Dong, C.J.; Huang, F.L.; Deng, H.; Schaffrath, C.; Spencer, J.B.; O'Hagan, D.; Naismith, J.H. Crystal Structure and Mechanism of a Bacterial Fluorinating Enzyme. Nature 2004, 427, 561-565.
15. Eisenberg, MA.; Stoner, G.L. Biosynthesis of 7,8-Diaminopelargonic Acid, a Biotin Intermediate, from 7-Keto-8-Aminoperlargonic Acid and S-Adenosyl-L-Methionine. J. Bacteriol. 1971, 108, 1135-1140.
16. Nishimura, S.; Taya, Y.; Kuchino, Y.; Ohashi, Z. Enzymatic-Synthesis of 3-(3-Amino-3- Carboxypropyl)Uridine in Escherichia-Coli Phenylalanine Transfer-RNA-Transfer of 3-Amino- 3-Carboxypropyl Group from S-Adenosylmethionine. Biochem. Biophys. Res. Commun. 1974, 57, 702-708.
17. Iwata-Reuyl, D. An Embarrassment of Riches: The Enzymology of RNA Modification. Curr. Opin. Chem. Biol. 2008, 12, 126-133.
18. van Lanen, S.G.; Kinzie, S.D.; Matthieu, S.; Link, T.; Culp, J.; Iwata-Reuyl, D. tRNA Modification by S-Adenosylmethionine: tRNA Ribosyltransferase-Isomerase-Assay Development and Characterization of the Recombinant Enzyme. J. Biol. Chem. 2003, 278, 10491-10499.
19. Iwata-Reuyl, D. Biosynthesis of the 7-Deazaguanosine Hypermodified Nucleosides of Transfer RNA. Bioorg. Chem. 2003, 31, 24-43. (Pubitemid 36416604)
20. Basturea, G.N.; Rudd, K.E.; Deutscher, M.P. Identification and Characterization of RsmE, the Founding Member of a New RNA Base Methyltransferase Family. RNA-Publ. RNA Soc. 2006, 12, 426-434.
21. Poole, A.; Penny, D.; Sjoberg, B.M. Methyl-RNA: An Evolutionary Bridge between RNA and DNA? Chem. Biol. 2000, 7, R207-R216.
22. Kerr, S.J.; Borek, E. Transfer-RNA Methyltransferases. Adv. Enzymol. Relat. Areas Mol. Biol. 1972, 36, 1-27.
23. Colonna, A.; Kerr, S.J. The Nucleus as the Site of Transfer-RNA Methylation. J. Cell. Physiol. 1980, 103, 29-33.
24. Tollervey, D. Small Nucleolar RNAs Guide Ribosomal RNA Methylation. Science 1996, 273, 1056-1057.
25. Maravic, G.; Flogel, M. RNA Methylation and Antibiotic Resistance: An Overview. Period. Biol. 2004, 106, 135-140.
26. Sitachitta, N.; Marquez, B.L.; Williamson, R.T.; Rossi, J.; Roberts, M.A.; Gerwick, W.H.; Nguyen, V.A.; Willis, C.L. Biosynthetic Pathway and Origin of the Chlorinated Methyl Group in Barbamide and Dechlorobarbamide, Metabolites from the Marine Cyanobacterium Lyngbya Majuscula. Tetrahedron 2000, 56, 9103-9113.
27. Flatt, P.M.; O'Connell, S.J.; McPhail, K.L.; Zeller, G.; Willis, C.L.; Sherman, D.H.; Gerwick, W.H. Characterization of the Initial Enzymatic Steps of Barbamide Biosynthesis. J. Nat. Prod. 2006, 69, 938-944. (Pubitemid 44166269)
28. Orjala, J.; Gerwick, W.H. Barbamide, a Chlorinated Metabolite with Molluscicidal Activity from the Caribbean Cyanobacterium Lyngbya Majuscula. J. Nat. Prod. 1996, 59, 427-430.
29. Chang, Z.X.; Sitachitta, N.; Rossi, J.V.; Roberts, M.A.; Flatt, P.M.; Jia, J.Y.; Sherman, D.H.; Gerwick, W.H. Biosynthetic Pathway and Gene Cluster Analysis of Curacin A, an Antitubulin Natural Product from the Tropical Marine Cyanobacterium Lyngbya Majuscula. J. Nat. Prod. 2004, 67, 1356-1367.
30. Kokke, W.; Shoolery, J.N.; Fenical, W.; Djerassi, C. Biosynthetic-Studies of Marine Lipids.4. Mechanism of Side-Chain Alkylation in (E)-24- Propylidenecholesterol by a Chrysophyte Alga. J. Org. Chem. 1984, 49, 3742-3752.
31. Giner, J.L.; Djerassi, C. Biosynthetic-Studies of Marine Lipids. 33. Biosynthesis of Dinosterol, Peridinosterol, and Gorgosterol - Unusual Patterns of Bioalkylation in Dinoflagellate Sterols. J. Org. Chem. 1991, 56, 2357-2363.
32. Kerr, R.G.; Kerr, S.L.; Djerassi, C. Biosynthetic-Studies of Marine Lipids. 26. Elucidation of the Biosynthesis of Mutasterol, a Sponge Sterol with a Quaternary Carbon in Its Side-Chain. J. Org. Chem. 1991, 56, 63-66.
33. Lang, G.; Wiese, J.; Schmaljohann, R.; Imhoff, J.F. New Pentaenes from the Sponge-Derived Marine Fungus Penicillium Rugulosum: Structure Determination and Biosynthetic Studies. Tetrahedron 2007, 63, 11844-11849.
34. Kobayashi, H.; Meguro, S.; Yoshimoto, T.; Namikoshi, M. Absolute Structure, Biosynthesis, and Anti-Microtubule Activity of Phomopsidin, Isolated from a Marine-Derived Fungus Phomopsis Sp. Tetrahedron 2003, 59, 455-459.
35. Bringmann, G.; Lang, G.; Gulder, T.A.M.; Tsuruta, H.; Muhlbacher, J.; Maksimenka, K.; Steffens, S.; Schaumann, K.; Stohr, R.; Wiese, J.; Imhoff, J.F.; Perovic-Ottstadt, S.; Boreiko, O.; Muller, W.E.G. The First Sorbicillinoid Alkaloids, the Antileukemic Sorbicillactones A and B, from a Sponge-Derived Penicillium Chrysogenum Strain. Tetrahedron 2005, 61, 7252-7265.
36. Cacciapuoti, G.; Porcelli, M.; Moretti, M.A.; Sorrentino, F.; Concilio, L.; Zappia, V.; Liu, Z.J.; Tempel, W.; Schubot, F.; Rose, J.P.; Wang, B.C.; Brereton, P.S.; Jenney, F.E.; Adams, M.W.W. The First Agmatine/Cadaverine Aminopropyl Transferase: Biochemical and Structural Characterization of an Enzyme Involved in Polyamine Biosynthesis in the Hyperthermophilic Archaeon Pyrococcus Furiosus. J. Bacteriol. 2007, 189, 6057-6067.
37. Kusano, T.; Berberich, T.; Tateda, C.; Takahashi, Y. Polyamines: Essential Factors for Growth and Survival. Planta 2008, 228, 367-381.
38. Shah, P.; Swlatlo, E. A Multifaceted Role for Polyamines in Bacterial Pathogens. Mol. Microbiol. 2008, 68, 4-16.
39. Kuehn, G.D.; Phillips, G.C. Role of Polyamines in Apoptosis and Other Recent Advances in Plant Polyamines. Crit. Rev. Plant Sci. 2005, 24, 123-130.
40. Williams, K. Modulation and Block of Ion Channels: A New Biology of Polyamines. Cell. Signal. 1997, 9, 1-13. (Pubitemid 27120861)
41. Igarashi, K.; Kashiwagi, K. Polyamines: Mysterious Modulators of Cellular Functions. Biochem. Biophys. Res. Commun. 2000, 271, 559-564.
42. Rhee, H.J.; Kim, E.J.; Lee, J.K. Physiological Polyamines: Simple Primordial Stress Molecules. J. Cell. Mol. Med. 2007, 11, 685-703.
43. Baron, K.; Stasolla, C. The Role of Polyamines During in Vivo and in Vitro Development. In Vitro Cell. Dev. Biol.-Plant 2008, 44, 384-395.
44. Groppa, M.D.; Benavides, M.P. Polyamines and Abiotic Stress: Recent Advances. Amino Acids 2008, 34, 35-45.
45. Williams, K. Interactions of Polyamines with Ion Channels. Biochem. J. 1997, 325, 289-297.
46. Terui, Y.; Ohnuma, M.; Hiraga, K.; Kawashima, E.; Oshima, T. Stabilization of Nucleic Acids by Unusual Polyamines Produced by an Extreme Thermophile, Thermus Thermophilus. Biochem. J. 2005, 388, 427-433. (Pubitemid 40839919)
47. Matsunaga, S.; Sakai, R.; Jimbo, M.; Kamiya, H. Long-Chain Polyamines (LCPAs) from Marine Sponge: Possible Implication in Spicule Formation. ChemBioChem 2007, 8, 1729-1735.
48. Kroger, N.; Deutzmann, R.; Bergsdorf, C.; Sumper, M. Species-Specific Polyamines from Diatoms Control Silica Morphology. Proc. Natl. Acad. Sci. USA 2000, 97, 14133-14138. (Pubitemid 32016542)
49. Sumper, M.; Lehmann, G. Silica Pattern Formation in Diatoms: Species-Specific Polyamine Biosynthesis. ChemBioChem 2006, 7, 1419-1427. (Pubitemid 44369094)
50. Sumper, M.; Brunner, E. Silica Biomineralisation in Diatoms: The Model Organism Thalassiosira Pseudonana. ChemBioChem 2008, 9, 1187-1194.
51. Foo, C.W.P.; Huang, J.; Kaplan, D.L. Lessons from Seashells: Silica Mineralization via Protein Templating. Trends Biotechnol. 2004, 22, 577-585.
52. Ohnuma, M.; Terui, Y.; Tamakoshi, M.; Mitome, H.; Niitsu, M.; Samejima, K.; Kawashima, E.; Oshima, T. N-1-Aminopropylagmatine, a New Polyamine Produced as a Key Intermediate in Polyamine Biosynthesis of an Extreme Thermophile, Thermus Thermophilus. J. Biol. Chem. 2005, 280, 30073-30082. (Pubitemid 41216183)
53. Palagiano, E.; Demarino, S.; Minale, L.; Riccio, R.; Zollo, F.; Iorizzi, M.; Carre, J.B.; Debitus, C.; Lucarain, L.; Provost, J. Ptilomycalin-A, Crambescidin-800 and Related New Highly Cytotoxic Guanidine Alkaloids from the Starfishes Fromia-Monilis and Celerina-Heffernani. Tetrahedron 1995, 51, 3675-3682.
54. Black, G.P.; Coles, S.J.; Hizi, A.; Howard-Jones, A.G.; Hursthouse, M.B.; McGown, A.T.; Loya, S.; Moore, C.G.; Murphy, P.J.; Smith, N.K.; Walshe, N.D.A. Synthesis and Biological Activity of Analogues of Ptilomycalin A. Tetrahedron Lett. 2001, 42, 3377-3381.
55. Lazaro, J.E.H.; Nitcheu, J.; Mahmoudi, N.; Ibana, J.A.; Mangalindan, G.C.; Black, G.P.; Howard-Jones, A.G.; Moore, C.G.; Thomas, D.A.; Mazier, D.; Ireland, C.M.; Concepcion, G.P.; Murphy, P.J.; Diquet, B. Antimalarial Activity of Crambescidin 800 and Synthetic Analogues against Liver and Blood Stage of Plasmodium Sp. J. Antibiot. 2006, 59, 583-590. (Pubitemid 44787684)
56. Kashman, Y.; Hirsh, S.; McConnell, O.J.; Ohtani, I.; Kusumi, T.; Kakisawa, H. Ptilomycalin-A - a Novel Polycyclic Guanidine Alkaloid of Marine Origin. J. Am. Chem. Soc. 1989, 111, 8925-8926. (Pubitemid 20050095)
57. Gassner, N.C.; Tamble, C.M.; Bock, J.E.; Cotton, N.; White, K.N.; Tenney, K.; St Onge, R.P.; Proctor, M.J.; Giaever, G.; Nislow, C.; Davis, R.W.; Crews, P.; Holman, T.R.; Lokey, R.S. Accelerating the Discovery of Biologically Active Small Molecules Using a High-Throughput Yeast Halo Assay. J. Nat. Prod. 2007, 70, 383-390.
58. Carter, G.T.; Rinehart, K.L. Acarnidines, Novel Anti-Viral and Anti-Microbial Compounds from Sponge Acarnus-Erithacus-(De Laubenfels). J. Am. Chem. Soc. 1978, 100, 4302-4304.
59. Schmitz, F.J.; Hollenbeak, K.H.; Prasad, R.S. Marine Natural-Products - Cytotoxic Spermidine Derivatives from the Soft Coral Sinularia-Brongersmai. Tetrahedron Lett. 1979, 3387-3390.
60. Karigiannis, G.; Papaioannou, D. Structure, Biological Activity and Synthesis of Polyamine Analogues and Conjugates. Eur. J. Org. Chem. 2000, 1841-1863.
61. Ushiosata, N.; Matsunaga, S.; Fusetani, N.; Honda, K.; Yasumuro, K. Penaramides, Which Inhibit Binding of Omega-Conotoxin Gvia to N-Type Ca2+ Channels, from the Marine Sponge Penares Aff Incrustans. Tetrahedron Lett. 1996, 37, 225-228. (Pubitemid 126335300)
62. Coffey, D.S.; McDonald, A.I.; Overman, L.E.; Rabinowitz, M.H.; Renhowe, P.A. A Practical Entry to the Crambescidin Family of Guanidine Alkaloids. Enantioselective Total Syntheses of Ptilomycalin a, Crambescidin 657 and Its Methyl Ester (Neofolitispates 2), and Crambescidin 800. J. Am. Chem. Soc. 2000, 122, 4893-4903.
63. Tsukamoto, S.; Kato, H.; Hirota, H.; Fusetani, N. Pseudoceratidine: A New Antifouling Spermidine Derivative from the Marine Sponge Pseudoceratina Purpurea. Tetrahedron Lett. 1996, 37, 1439-1440. (Pubitemid 26081793)
64. Buchanan, M.S.; Carroll, A.R.; Fechner, G.A.; Boyle, A.; Simpson, M.M.; Addepalli, R.; Avery, V.M.; Hooper, J.N.A.; Su, N.; Chen, H.W.; Quinn, R.J. Spermatinamine, the First Natural Product Inhibitor of Isoprenylcysteine Carboxyl Methyltransferase, a New Cancer Target. Bioorg. Med. Chem. Lett. 2007, 17, 6860-6863.
65. Koppisch, A.T.; Browder, C.C.; Moe, A.L.; Shelley, J.T.; Kinke, B.A.; Hersman, L.E.; Iyer, S.; Ruggiero, C.E. Petrobactin is the Primary Siderophore Synthesized by Bacillus Anthracis Str. Sterne under Conditions of Iron Starvation. BioMetals 2005, 18, 577-585.
66. Sata, N.U.; Sugano, M.; Matsunaga, S.; Fusetani, N. Bioactive Marine Metabolites - Part 88 - Sinulamide: An H,K-ATPase Inhibitor from a Soft Coral Sinularia sp. Tetrahedron Lett. 1999, 40, 719-722.
67. Wright, L.P.; Philips, M.R. Caax Modification and Membrane Targeting of Ras. J. Lipid Res. 2006, 47, 883-891.
68. Barbeau, K.; Zhang, G.P.; Live, D.H.; Butler, A. Petrobactin, a Photoreactive Siderophore Produced by the Oil-Degrading Marine Bacterium Marinobacter Hydrocarbonoclasticus. J. Am. Chem. Soc. 2002, 124, 378-379.
69. Koppisch, A.T.; Dhungana, S.; Hill, K.K.; Boukhalfa, H.; Heine, H.S.; Colip, L.A.; Romero, R.B.; Shou, Y.L.; Ticknor, L.O.; Marrone, B.L.; Hersman, L.E.; Iyer, S.; Ruggiero, C.E. Petrobactin is Produced by Both Pathogenic and Non-Pathogenic Isolates of the Bacillus Cereus Group of Bacteria. BioMetals 2008, 21, 581-589.
70. Bergeron, R.J.; Huang, G.F.; Smith, R.E.; Bharti, N.; McManis, J.S.; Butler, A. Total Synthesis and Structure Revision of Petrobactin. Tetrahedron 2003, 59, 2007-2014. (Pubitemid 36255684)
71. Gardner, R.A.; Kinkade, R.; Wang, C.J.; Phanstiel, O. Total Synthesis of Petrobactin and Its Homologues as Potential Growth Stimuli for Marinobacter Hydrocarbonoclasticus, an Oil- Degrading Bacteria. J. Org. Chem. 2004, 69, 3530-3537.
72. Abergel, R.J.; Wilson, M.K.; Arceneaux, J.E.L.; Hoette, T.M.; Strong, R.K.; Byers, B.R.; Raymond, K.N. Anthrax Pathogen Evades the Mammalian Immune System through Stealth Siderophore Production. Proc. Natl. Acad. Sci. USA 2006, 103, 18499-18503.
73. Gardner, R.A.; Kinkade, R.; Wang, C.J.; Phanstiel, O. Total Synthesis of Petrobactin and Its Homologues as Potential Growth Stimuli for Marinobacter Hydrocarbonoclasticus, an Oil- Degrading Bacteria. (Correction). J. Org. Chem. 2007, 72, 3158-3158
74. Lee, J.Y.; Janes, B.K.; Passalacqua, K.D.; Pfleger, B.F.; Bergman, N.H.; Liu, H.C.; Hakansson, K.; Somu, R.V.; Aldrich, C.C.; Cendrowski, S.; Hanna, P.C.; Sherman, D.H. Biosynthetic Analysis of the Petrobactin Siderophore Pathway from Bacillus Anthracis. J. Bacteriol. 2007, 189, 1698-1710. (Pubitemid 46446132)
75. Oves-Costales, D.; Kadi, N.; Fogg, M.J.; Song, L.; Wilson, K.S.; Challis, G.L. Enzymatic Logic of Anthrax Stealth Siderophore Biosynthesis: AsbA Catalyzes ATP-Dependent Condensation of Citric Acid and Spermidine. J. Am. Chem. Soc. 2007, 129, 8416-8417.
76. Pfleger, B.F.; Lee, J.Y.; Somu, R.V.; Aldrich, C.C.; Hanna, P.C.; Sherman, D.H. Characterization and Analysis of Early Enzymes for Petrobactin Biosynthesis in Bacillus Anthracis. Biochemistry (Mosc). 2007, 46, 4147-4157. (Pubitemid 46536076)
77. Fox, D.T.; Hotta, K.; Kim, C.Y.; Koppisch, A.T. The Missing Link in Petrobactin Biosynthesis: AsbF Encodes a (-)-3-Dehydroshikimate Dehydratase. Biochemistry (Mosc). 2008, 47, 12251-12253.
78. Koppisch, A.T.; Hotta, K.; Fox, D.T.; Ruggiero, C.E.; Kim, C.Y.; Sanchez, T.; Iyer, S.; Browder, C.C.; Unkefer, P.J.; Unkefer, C.J. Biosynthesis of the 3,4-Dihydroxybenzoate Moieties of Petrobactin by Bacillus Anthracis. J. Org. Chem. 2008, 73, 5759-5765.
79. Pfleger, B.F.; Kim, Y.C.; Nusca, T.D.; Maltseva, N.; Lee, J.Y.; Rath, C.M.; Scaglione, J.B.; Janes, B.K.; Anderson, E.C.; Bergman, N.H.; Hanna, P.C.; Joachimiak, A.; Sherman, D.H. Structural and Functional Analysis of AsbF: Origin of the Stealth 3,4-Dihydroxybenzoic Acid Subunit for Petrobactin Biosynthesis. Proc. Natl. Acad. Sci. U. S. A. 2008, 105, 17133-17138.
80. Lee, J.; Sperandio, V.; Frantz, D.E.; Longgood, J.; Camilli, A.; Phillips, M.A.; Michael, A.J. An Alternative Polyamine Biosynthetic Pathway Is Widespread in Bacteria and Essential for Biofilm Formation in Vibrio Cholerae. J. Biol. Chem. 2009, 284, 9899-9907.
81. Oves-Costales, D.; Song, L.; Challis, G.L. Enantioselective Desymmetrisation of Citric Acid Catalysed by the Substrate-Tolerant Petrobactin Biosynthetic Enzyme AsbA. Chem. Commun. 2009, 1389-1391.
82. Ponasik, J.A.; Kassab, D.J.; Ganem, B. Synthesis of the Antifouling Polyamine Pseudoceratidine and Its Analogs: Factors Influencing Biocidal Activity. Tetrahedron Lett. 1996, 37, 6041-6044. (Pubitemid 26259509)
83. Ponasik, J.A.; Conova, S.; Kinghorn, D.; Kinney, W.A.; Rittschof, D.; Ganem, B. Pseudoceratidine, a Marine Natural Product with Antifouling Activity: Synthetic and Biological Studies. Tetrahedron 1998, 54, 6977-6986.
84. Katz, J.E.; Dlakic, M.; Clarke, S. Automated Identification of Putative Methyltransferases from Genomic Open Reading Frames. Mol. Cell. Proteomics 2003, 2, 525-540.
85. Fujioka, M. Mammalian Small Molecule Methyltransferases - Their Structural and Functional Features. Int. J. Biochem. 1992, 24, 1917-1924.
86. Cheng, X.D.; Roberts, R.J. AdoMet-Dependent Methylation, DNA Methyltransferases and Base Flipping. Nucleic Acids Res. 2001, 29, 3784-3795.
87. Yeates, T.O. Structures of Set Domain Proteins: Protein Lysine Methyltransferases Make Their Mark. Cell 2002, 111, 5-7.
88. Romano, J.D.; Michaelis, S. Topological and Mutational Analysis of Saccharomyces Cerevisiae Ste14p, Founding Member of the Isoprenylcysteine Carboxyl Methyltransferase Family. Mol. Biol. Cell 2001, 12, 1957-1971.
89. Farooqi, A.H.A.; Shukla, Y.N.; Shukla, A.; Bhakuni, D.S. Cytokinins from Marine Organisms. Phytochemistry 1990, 29, 2061-2063.
90. Ashour, M.; Edrada-Ebel, R.; Ebel, R.; Wray, V.; Van Soest, R.W.M.; Proksch, P. New Purine Derivatives from the Marine Sponge Petrosia Nigricans. Nat. Prod. Commun. 2008, 3, 1889-1894.
91. Lindsay, B.S.; Battershill, C.N.; Copp, B.R. 1,3-Dimethylguanine, a New Purine from the New Zealand Ascidian Botrylloides Leachi. J. Nat. Prod. 1999, 62, 638-639.
92. Tasdemir, D.; Mangalindan, G.C.; Concepcion, G.P.; Harper, M.K.; Irelanda, C.M. 3,7- Dimethylguanine, a New Purine from a Philippine Sponge Zyzzya Fuliginosa. Chem. Pharm. Bull. (Tokyo) 2001, 49, 1628-1630.
93. Perry, N.B.; Blunt, J.W.; Munro, M.H.G. 1,3,7-Trimethylguanine from the Sponge Latrunculia- Brevis. J. Nat. Prod. 1987, 50, 307-308.
94. Berry, Y.; Bremner, J.B.; Davis, A.; Samosorn, S. Isolation and NMR Spectroscopic Clarification of the Alkaloid 1,3,7-Trimethylguanine from the Ascidian Eudistoma Maculosum. Nat. Prod. Res. 2006, 20, 479-483.
95. Pearce, A.N.; Babcock, R.C.; Lambert, G.; Copp, B.R. N-2,N-2,7- Trimethylguanine, a New Trimethylated Guanine Natural Product from the New Zealand Ascidian, Lissoclinum Notti. Nat. Prod. Lett. 2001, 15, 237-241.
96. Lindsay, B.S.; Almeida, A.M.P.; Smith, C.J.; Berlinck, R.G.S.; Da Rocha, R.M.; Ireland, C.M. 6- Methoxy-7-Methyl-8-Oxoguanine, an Unusual Purine from the Ascidian Symplegma Rubra. J. Nat. Prod. 1999, 62, 1573-1575.
97. Chehade, C.C.; Dias, R.L.A.; Berlinck, R.G.S.; Ferreira, A.G.; Costa, L.V.; Rangel, M.; Malpezzi, E.L.A.; Defreitas, J.C.; Hajdu, E. 1,3-Dimethylisoguanine, a New Purine from the Marine Sponge Amphimedon Viridis. J. Nat. Prod. 1997, 60, 729-731. (Pubitemid 27318426)
98. Cafieri, F.; Fattorusso, E.; Mangoni, A.; Taglialatelascafati, O. Longamide and 3,7- Dimethylisoguanine, 2 Novel Alkaloids from the Marine Sponge Agelas-Longissima. Tetrahedron Lett. 1995, 36, 7893-7896.
99. Copp, B.R.; Wassvik, C.M.; Lambert, G.; Page, M.J. Isolation and Characterization of the New Purine 1,3,7-Trimethylisoguanine from the New Zealand Ascidian Pseudodistoma Cereum. J. Nat. Prod. 2000, 63, 1168-1169.
100. Appleton, D.R.; Page, M.J.; Lambert, G.; Copp, B.R. 1,3-Dimethyl-8- Oxoisoguanine, a New Purine from the New Zealand Ascidian Pseudodistoma Cereum. Nat. Prod. Res. 2004, 18, 39-42.
101. Derosa, S.; Destefano, S.; Puliti, R.; Mattia, C.A.; Mazzarella, L. Isolation and X-Ray Crystal- Structure of a Derivative of 2,6-Diaminopurine from a Sea-Anemone. J. Nat. Prod. 1987, 50, 876-880. (Pubitemid 17158672)
102. Cimino, G.; Degiulio, A.; Derosa, S.; Destefano, S.; Puliti, R.; Mattia, C.A.; Mazzarella, L. Isolation and X-Ray Crystal-Structure of a Novel 8-Oxopurine Compound from a Marine Sponge. J. Nat. Prod. 1985, 48, 523-528.
103. Cooper, R.A.; Defreitas, J.C.; Porreca, F.; Eisenhour, C.M.; Lukas, R.; Huxtable, R.J. The Sea- Anemone Purine, Caissarone - Adenosine Receptor Antagonism. Toxicon 1995, 33, 1025-1031.
104. Yagi, H.; Matsunaga, S.; Fusetani, N. Isolation of 1-Methylherbipoline, a Purine Base, from a Marine Sponge, Jaspis Sp. J. Nat. Prod. 1994, 57, 837-838. (Pubitemid 24249329)
105. Bourguet-Kondracki, M.L.; Martin, M.T.; Vacelet, J.; Guyot, M. Mucronatine, a New N-Methyl Purine from the French Mediterranean Marine Sponge Stryphnus Mucronatus. Tetrahedron Lett. 2001, 42, 7257-7259.
106. Rosemeyer, H. The Chemodiversity of Purine as a Constituent of Natural Products. Chem. Biodivers. 2004, 1, 361-401.
107. Kerr, R.G.; Baker, B.J. Marine Sterols. Nat. Prod. Rep. 1991, 8, 465-497.
108. Giner, J.L.; Faraldos, J.A.; Boyer, G.L. Novel Sterols of the Toxic Dinoflagellate Karenia Brevis (Dinophyceae): A Defensive Function for Unusual Marine Sterols? J. Phycol. 2003, 39, 315-319.
109. Nechev, J.; Christie, W.W.; Robaina, R.; De Diego, F.; Popov, S.; Stefanov, K. Chemical Composition of the Sponge Hymeniacidon Sanguinea from the Canary Islands. Comp. Biochem. Physiol. A: Mol. Integr. Physiol. 2004, 137, 365-374. (Pubitemid 38186602)
110. Djerassi, C.; Lam, W.K. Phospholipid Studies of Marine Organisms .25. Sponge Phospholipids. Acc. Chem. Res. 1991, 24, 69-75.
111. Giner, J.L. Biosynthesis of Marine Sterol Side-Chains. Chem. Rev. 1993, 93, 1735-1752.
112. Aoki, S.; Watanabe, Y.; Tanabe, D.; Arai, M.; Suna, H.; Miyamoto, K.; Tsujibo, H.; Tsujikawa, K.; Yamamoto, H.; Kobayashi, M. Structure-Activity Relationship and Biological Property of Cortistatins, Anti-Angiogenic Spongean Steroidal Alkaloids. Bioorg. Med. Chem. 2007, 15, 6758-6762.
113. Guo, H.W.; Ecker, J.R. The Ethylene Signaling Pathway: New Insights. Curr. Opin. Plant Biol. 2004, 7, 40-49.
114. Pandey, S.; Ranade, S.A.; Nagar, P.K.; Kumar, N. Role of Polyamines and Ethylene as Modulators of Plant Senescence. J. Biosci. (Bangalore) 2000, 25, 291-299.
115. Alonso, J.M.; Stepanova, A.N. The Ethylene Signaling Pathway. Science 2004, 306, 1513-1515.
116. Bleecker, A.B.; Kende, H. Ethylene: A Gaseous Signal Molecule in Plants. Ann. Rev. Cell. Dev. Biol. 2000, 16, 1-18.
117. Roje, S. S-Adenosyl-L-Methionine: Beyond the Universal Methyl Group Donor. Phytochem. 2006, 67, 1686-1698. (Pubitemid 44233619)
118. Wang, K.L.C.; Li, H.; Ecker, J.R. Ethylene Biosynthesis and Signaling Networks. Plant Cell 2002, 14, S131-S151.
119. Plettner, I.; Steinke, M.; Malin, G. Ethene (Ethylene) Production in the Marine Macroalga Ulva (Enteromorpha) Intestinalis L. (Chlorophyta, Ulvophyceae): Effect of Light-Stress and Co-Production with Dimethyl Sulphide. Plant Cell Environ. 2005, 28, 1136-1145.
120. Watanabe, T.; Kondo, N. Ethylene Evolution in Marine-Algae and a Proteinaceous Inhibitor of Ethylene Biosynthesis from Red Alga. Plant Cell Physiol. 1976, 17, 1159-1166.
121. Watanabe, T.; Kondo, N.; Fujii, T.; Noguchi, T. Affinity Chromatography of an Ethylene- Synthesizing Enzyme from Red Alga Porphyra-Tenera on an Immobilized Inhibitor of Ethylene Evolution. Plant Cell Physiol. 1977, 18, 387-392.
122. Krasko, A.; Schroder, H.C.; Perovic, S.; Steffen, R.; Kruse, M.; Reichert, W.; Muller, I.M.; Muller, W.E.G. Ethylene Modulates Gene Expression in Cells of the Marine Sponge Suberites Domuncula and Reduces the Degree of Apoptosis. J. Biol. Chem. 1999, 274, 31524-31530. (Pubitemid 129501608)
123. O'Hagan, D. Recent Developments on the Fluorinase from Streptomyces Cattleya. J. Fluorine Chem. 2006, 127, 1479-1483.
124. Fujimori, D.G.; Walsh, C.T. What's New in Enzymatic Halogenations. Curr. Opin. Chem. Biol. 2007, 11, 553-560.
125. Blasiak, L.C.; Drennan, C.L. Structural Perspective on Enzymatic Halogenation. Acc. Chem. Res. 2009, 42, 147-155.
126. Deng, H.; Cobb, S.L.; McEwan, A.R.; McGlinchey, R.P.; Naismith, J.H.; O'Hagan, D.; Robinson, D.A.; Spencer, J.B. The Fluorinase from Streptomyces Cattleya is also a Chlorinase. Angew. Chem. Int. Ed. (Engl) 2006, 45, 759-762.
127. Layer, G.; Heinz, D.W.; Jahn, D.; Schubert, W.D. Structure and Function of Radical SAM Enzymes. Curr. Opin. Chem. Biol. 2004, 8, 468-476.
128. Wang, S.C.; Frey, P.A. S-Adenosylmethionine as an Oxidant: The Radical SAM Superfamily. Trends Biochem. Sci. 2007, 32, 101-110.
129. Booker, S.J.; Cicchillo, R.M.; Grove, T.L. Self-Sacrifice in Radical S-Adenosylmethionine Proteins. Curr. Opin. Chem. Biol. 2007, 11, 543-552.
130. Duschene, K.S.; Veneziano, S.E.; Silver, S.C.; Broderick, J.B. Control of Radical Chemistry in the AdoMet Radical Enzymes. Curr. Opin. Chem. Biol. 2009, 13, 74-83.
131. Chew, A.G.M.; Frigaard, N.U.; Bryant, D.A. Bacteriochlorophyllide c C-8(2) and C-12(1) Methyltransferases Are Essential for Adaptation to Low Light in Chlorobaculum Tepidum. J. Bacteriol. 2007, 189, 6176-6184.
132. Huster, M.S.; Smith, K.M. Biosynthetic Studies of Substituent Homologation in Bacteriochlorophylls c and d. Biochemistry (Mosc). 1990, 29, 4348-4355.
133. Swingley, W.D.; Chen, M.; Cheung, P.C.; Conrad, A.L.; Dejesa, L.C.; Hao, J.; Honchak, B.M.; Karbach, L.E.; Kurdoglu, A.; Lahiri, S.; Mastrian, S.D.; Miyashita, H.; Page, L.; Ramakrishna, P.; Satoh, S.; Sattley, W.M.; Shimada, Y.; Taylor, H.L.; Tomo, T.; Tsuchiya, T.; Wang, Z.T.; Raymond, J.; Mimuro, M.; Blankenship, R.E.; Touchman, J.W. Niche Adaptation and Genome Expansion in the Chlorophyll d-Producing Cyanobacterium Acarylochloris Marina. Proc. Natl. Acad. Sci. USA 2008, 105, 2005-2010.
134. Fuqua, W.C.; Winans, S.C.; Greenberg, E.P. Quorum Sensing in Bacteria - the LuxR-LuxI Family of Cell Density-Responsive Transcriptional Regulators. J.Bacteriol. 1994, 176, 269-275.
135. Hastings, J.W.; Greenberg, E.P. Quorum Sensing: The Explanation of a Curious Phenomenon Reveals a Common Characteristic of Bacteria. J. Bacteriol. 1999, 181, 2667-2668.
136. Fuqua, C.; Greenberg, E.P. Self Perception in Bacteria: Quorum Sensing with Acylated Homoserine Lactones. Curr. Opin. Microbiol. 1998, 1, 183-189.
137. Fuqua, C.; Greenberg, E.P. Listening in on Bacteria: Acyl-Homoserine Lactone Signalling. Nat. Rev. Mol. Cell Biol. 2002, 3, 685-695.
138. Schaefer, A.L.; Val, D.L.; Hanzelka, B.L.; Cronan, J.E.; Greenberg, E.P. Generation of Cell-to- Cell Signals in Quorum Sensing: Acyl Homoserine Lactone Synthase Activity of a Purified Vibrio Fescheri LuxI Protein. Proc. Natl. Acad. Sci. USA 1996, 93, 9505-9509.
139. Milton, D.L. Quorum Sensing in Vibrios: Complexity for Diversification. Int. J. Med. Microbiol. 2006, 296, 61-71.
140. Krick, A.; Kehraus, S.; Eberl, L.; Riedel, K.; Anke, H.; Kaesler, I.; Graeber, I.; Szewzyk, U.; Konig, G.M. A Marine Mesorhizobium Sp Produces Structurally Novel Long-Chain N-Acyl-LHomoserine Lactones. Appl. Environ. Microbiol. 2007, 73, 3587-3594.
141. Brinkhoff, T.; Giebel, H.A.; Simon, M. Diversity, Ecology, and Genomics of the Roseobacter Clade: A Short Overview. Arch. Microbiol. 2008, 189, 531-539.
142. Wagner-Dobler, I.; Biebl, H. Environmental Biology of the Marine Roseobacter Lineage. Annu. Rev. Microbiol. 2006, 60, 255-280. (Pubitemid 44627949)
143. Wagner-Dobler, I.; Thiel, V.; Eberl, L.; Allgaier, M.; Bodor, A.; Meyer, S.; Ebner, S.; Hennig, A.; Pukall, R.; Schulz, S. Discovery of Complex Mixtures of Novel Long-Chain Quorum Sensing Signals in Free-Living and Host-Associated Marine Alphaproteobacteria. ChemBioChem 2005, 6, 2195-2206. (Pubitemid 46259995)
144. Buchan, A.; Gonzalez, J.M.; Moran, M.A. Overview of the Marine Roseobacter Lineage. Appl. Environ. Microbiol. 2005, 71, 5665-5677.
145. Rickard, A.H.; Palmer, R.J.; Blehert, D.S.; Campagna, S.R.; Semmelhack, M.F.; Egland, P.G.; Bassler, B.L.; Kolenbrander, P.E. Autoinducer 2: A Concentration-Dependent Signal for Mutualistic Bacterial Biofilm Growth. Mol. Microbiol. 2006, 60, 1446-1456.
146. Sturme, M.H.J.; Kleerebezem, M.; Nakayama, J.; Akkermans, A.D.L.; Vaughan, E.E.; de Vos, W.M. Cell to Cell Communication by Autoinducing Peptides in Gram-Positive Bacteria. Anton Leeuw Int. J. G. Mol. Microbiol. 2002, 81, 233-243.
147. Federle, M.J.; Bassler, B.L. Interspecies Communication in Bacteria. J. Clin. Invest. 2003, 112, 1291-1299.
148. Uroz, S.; Dessaux, Y.; Oger, P. Quorum Sensing and Quorum Quenching: The Yin and Yang of Bacterial Communication. ChemBioChem 2009, 10, 205-216.
149. Kaufmann, G.F.; Sartorio, R.; Lee, S.H.; Rogers, C.J.; Meijler, M.M.; Moss, J.A.; Clapham, B.; Brogan, A.P.; Dickerson, T.J.; Janda, K.D. Revisiting Quorum Sensing: Discovery of Additional Chemical and Biological Functions for 3-Oxo-N-Acylhomoserine Lactones. Proc. Natl. Acad. Sci. USA 2005, 102, 309-314.
150. Roggo, B.E.; Petersen, F.; Delmendo, R.; Jenny, H.B.; Peter, H.H.; Roesel, J. 3-Alkanoyl-5- Hydroxymethyl Tetronic Acid Homologs and Resistomycin - New Inhibitors of HIV-1 Protease. 1. Fermentation, Isolation and Biological-Activity. J. Antibiot. 1994, 47, 136-142. (Pubitemid 24075567)
151. Schobert, R. Domino Syntheses of Bioactive Tetronic and Tetramic Acids. Naturwissenschaften 2007, 94, 1-11. (Pubitemid 44973668)
152. Roggo, B.E.; Hug, P.; Moss, S.; Raschdorf, F.; Peter, H.H. 3-Alkanoyl-5-Hydroxymethyl- Tetronic Acid Homologs - New Inhibitors of HIV-1 Protease. 2. Structure Determination. J. Antibiot. 1994, 47, 143-147.
153. Denys, R.; Wright, A.D.; Konig, G.M.; Sticher, O. New Halogenated Furanones from the Marine Alga Delisea-Pulchra (cf. Fimbriata). Tetrahedron 1993, 49, 11213-11220. (Pubitemid 23361320)
154. Persson, T.; Givskov, M.; Nielsen, J. Quorum Sensing Inhibition: Targeting Chemical Communication in Gram-Negative Bacteria. Curr. Med. Chem. 2005, 12, 3103-3115.
155. Givskov, M.; Denys, R.; Manefield, M.; Gram, L.; Maximilien, R.; Eberl, L.; Molin, S.; Steinberg, P.D.; Kjelleberg, S. Eukaryotic Interference with Homoserine Lactone-Mediated Prokaryotic Signaling. J. Bacteriol 1996, 178, 6618-6622. (Pubitemid 26374731)
156. Manefield, M.; De Nys, R.; Kumar, N.; Read, R.; Givskov, M.; Steinberg, P.; Kjelleberg, S.A. Evidence that Halogenated Furanones from Delisea Pulchra Inhibit Acylated Homoserine Lactone (AHL)-Mediated Gene Expression by Displacing the AHL Signal from Its Receptor Protein. Microbiol.-UK 1999, 145, 283-291.
157. Williams, D.E.; Lassota, P.; Andersen, R.J. Motuporamines A-C, Cytotoxic Alkaloids Isolated from the Marine Sponge Xestospongia Exigua (Kirkpatrick). J. Org. Chem. 1998, 63, 4838-4841. (Pubitemid 28342981)
158. Williams, D.E.; Craig, K.S.; Patrick, B.; McHardy, L.M.; Van Soest, R.; Roberge, M.; Andersen, R.J. Motuporamines, Anti-Invasion and Anti-Angiogenic Alkaloids from the Marine Sponge Xestospongia Exigua (Kirkpatrick): Isolation, Structure Elucidation, Analogue Synthesis, and Conformational Analysis. J. Org. Chem. 2002, 67, 245-258.
159. Roskelley, C.D.; Williams, D.E.; McHardy, L.M.; Leong, K.G.; Troussard, A.; Karsan, A.; Andersen, R.J.; Dedhar, S.; Roberge, M. Inhibition of Tumor Cell Invasion and Angiogenesis by Motuporamines. Cancer Res. 2001, 61, 6788-6794. (Pubitemid 32896502)
160. To, K.C.W.; Loh, K.T.; Roskelley, C.D.; Andersen, R.J.; O'Connor, T.P. The Anti-Invasive Compound Motuporamine C is a Robust Stimulator of Neuronal Growth Cone Collapse. Neurosci. 2006, 139, 1263-1274.
161. To, K.C.W.; Church, J.; O'Connor, T.P. Growth Cone Collapse Stimulated by both Calpain- and Rho-Mediated Pathways. Neurosci. 2008, 153, 645-653.
162. Luibrand, R.T.; Erdman, T.R.; Vollmer, J.J.; Scheuer, P.J.; Finer, J.; Clardy, J. Ilimaquinone, a Sesquiterpenoid Quinone from a Marine Sponge. Tetrahedron 1979, 35, 609-612.
163. Takizawa, P.A.; Yucel, J.K.; Veit, B.; Faulkner, D.J.; Deerinck, T.; Soto, G.; Ellisman, M.; Malhotra, V. Complete Vesiculation of Golgi Membranes and Inhibition of Protein-Transport by a Novel Sea Sponge Metabolite, Ilimaquinone. Cell 1993, 73, 1079-1090. (Pubitemid 23180483)
164. Dinter, A.; Berger, E.G. Golgi-Disturbing Agents. Histochem. Cell Biol. 1998, 109, 571-590.
165. Mayer, T.U. Chemical Genetics: Tailoring Tools for Cell Biology. Trends Cell Biol. 2003, 13, 270-277.
166. Radeke, H.S.; Digits, C.A.; Casaubon, R.L.; Snapper, M.L. Interactions of (-)-Ilimaquinone with Methylation Enzymes: Implications for Vesicular-Mediated
167. Moore, K.S.; Wehrli, S.; Roder, H.; Rogers, M.; Forrest, J.N.; McCrimmon, D.; Zasloff, M. Squalamine - an Aminosterol Antibiotic from the Shark. Proc. Natl. Acad. Sci. USA 1993, 90, 1354-1358.
168. Rao, M.N.; Shinnar, A.E.; Noecker, L.A.; Chao, T.L.; Feibush, B.; Snyder, B.; Sharkansky, I.; Sarkahian, A.; Zhang, X.H.; Jones, S.R.; Kinney, W.A.; Zasloff, M. Aminosterols from the Dogfish Shark Squalus-Acanthias. J. Nat. Prod. 2000, 63, 631-635.
169. Singh, R.; Sharma, M.; Joshi, P.; Rawat, D.S. Clinical Status of Anti-Cancer Agents Derived from Marine Sources. Anti-Cancer Agents Med. Chem. 2008, 8, 603-617.
170. Pontius, A.; Krick, A.; Mesry, R.; Kehraus, S.; Foegen, S.E.; Muller, M.; Klimo, K.; Gerhauser, C.; Konig, G.M. Monodictyochromes A and B, Dimeric Xanthone Derivatives from the Marine Algicolous Fungus Monodictys Putredinis. J. Nat. Prod. 2008, 71, 1793-1799.
171. Marquez, B.L.; Watts, K.S.; Yokochi, A.; Roberts, M.A.; Verdier-Pinard, P.; Jimenez, J.I.; Hamel, E.; Scheuer, P.J.; Gerwick, W.H. Structure and Absolute Stereochemistry of Hectochlorin, a Potent Stimulator of Actin Assembly. J. Nat. Prod. 2002, 65, 866-871.
172. Suntornchashwej, S.; Chaichit, N.; Isobe, M.; Suwanborirux, K. Hectochlorin and Morpholine Derivatives from the Thai Sea Hare, Bursatella Leachii. J. Nat. Prod. 2005, 68, 951-955.
173. Ramaswamy, A.V.; Sorrels, C.M.; Gerwick, W.H. Cloning and Biochemical Characterization of the Hectochlorin Biosynthetic Gene Cluster from the Marine Cyanobacterium Lyngbya Majuscula. J. Nat. Prod. 2007, 70, 1977-1986.
174. Edwards, D.J.; Marquez, B.L.; Nogle, L.M.; McPhail, K.; Goeger, D.E.; Roberts, M.A.; Gerwick, W.H. Structure and Biosynthesis of the Jamaicamides, New Mixed Polyketide-Peptide Neurotoxins from the Marine Cyanobacterium Lyngbya Majuscula. Chem. Biol. 2004, 11, 817-833.
175. Kehraus, S.; Gorzalka, S.; Hallmen, C.; Iqbal, J.; Muller, C.E.; Wright, A.D.; Wiese, M.; Konig, G.M. Novel Amino Acid Derived Natural Products from the Ascidian Atriolum Robustum: Identification and Pharmacological Characterization of a Unique Adenosine Derivative. J. Med. Chem. 2004, 47, 2243-2255.
176. Schlenk, F. Methylthioadenosine. Adv. Enzymol. Relat. Areas Mol. Biol. 1983, 54, 195-265.
177. Grillo, M.A.; Colombatto, S. S-Adenosylmethionine and Its Products. Amino Acids 2008, 34, 187-193.
178. Kamatani, N.; Kubota, M.; Willis, E.H.; Frincke, L.A.; Carson, D.A. 5′-Methylthioadenosine Is the Major Source of Adenine in Human-Cells. Adv. Exp. Med. Biol. 1984, 165, 83-88.
179. Walker, J.; Barrett, J. Parasite Sulphur Amino Acid Metabolism. Int. J. Parasitol. 1997, 27, 883-897. (Pubitemid 27368586)
180. Sekowska, A.; Kung, H.F.; Danchin, A. Sulfur Metabolism in Escherichia coli and Related Bacteria: Facts and Fiction. J. Mol. Microbiol. Biotechnol. 2000, 2, 145-177. (Pubitemid 30218817)
181. Pirkov, I.; Norbeck, J.; Gustafsson, L.; Albers, E. A Complete Inventory of All Enzymes in the Eukaryotic Methionine Salvage Pathway. FEBS J. 2008, 275, 4111-4120.
182. Gibbs, N.K.; Tye, J.; Norval, M. Recent Advances in Urocanic Acid Photochemistry, Photobiology and Photoimmunology. Photochem. Photobiol. Sci. 2008, 7, 655-667. (Pubitemid 351798454)