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Biological Effects and Biosynthesis of Brominated Metabolites

  • Chapter
Organic Bromine and Iodine Compounds

Part of the book series: The Handbook of Environmental Chemistry ((HEC3,volume 3R))

Abstract

On the basis of halogenated metabolites assembled by Gribble, an attempt is made to provide a hypothesis for the biosynthesis of representative groups. Examples of brominated and iodinated metabolites are drawn from the major classes of terpenoids and acetogenins, and related to the biosynthesis of their putative precursors. Brominated and iodinated carbocyclic and heterocyclic aromatic compounds are discussed as well as mechanisms for the oxidative coupling of phenolic substrates. A few chlorinated metabolites are introduced for additional illustration. Halogenation by cationoid (Hal+) reactions catalyzed by haloperoxidases is discussed, and attention drawn to the alternative role of anionoid (Hal-) halogenation. The presentation is extended to the biosynthesis of isonitriles and dichloroimines by anionoid reaction of precursors with cyanide. The range of biota that produce brominated substrates is briefly indicated, and comments made on the ecological significance of metabolites and associations among biota.

In memory of Arthur Lapworth, Robert Robinson, and Christopher Ingold, pioneers of the electronic theory of organic chemistry

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References

  1. Abe I, Rohmer M, Prestwish GD (1993) Enzymatic cyclization of squalene and oxi-dosqualene to sterols and triterpenes. Chem Rev 93:2189–2208

    CAS  Google Scholar 

  2. Alam M, Sanduja R, Wellington GM (1988) Tubastraine: isolation and structure of a novel alkaloid from the stony coral Tubastraea micrantha. Heterocycles 27:719–723

    CAS  Google Scholar 

  3. Allard A-S, Remberger M, Neilson AH (1987) Bacterial O-methylation of halogen-substituted phenols. Appl Environ Microbiol 53:839–845

    CAS  Google Scholar 

  4. Almeida M, Humanes M, Melo R, Silva JA, Fraüsto Da Silva JJR, Vilters H, Wever R (1998) Sacchorhiza polyschides (Phaeophyceae: Phyllariaceae) a new source for vanadium-dependent haloperoxidases Phytochem 48:229–239

    CAS  Google Scholar 

  5. Amachi S, Kamagata Y, Kanagawa T, Muramatsu Y (2001) Bacteria mediate methylation of iodide in marine and terrestrial environments. Appl Environ Microbiol 67:2718–2722

    CAS  Google Scholar 

  6. Asahina Y, Shibata S(1971) Chemistry of lichen substances. Asher, Amsterdam

    Google Scholar 

  7. Assmann M, Lichte E, Pawlik JR, Köck M (2000) Chemical defenses of the Caribbean sponges Agelas wiedenmayri and Agelas conifera. Mar Ecol Prog Ser 207:255–262

    CAS  Google Scholar 

  8. Assmann M, van Soest RWM, Köck M (2001) New antifeedant bromopyrrole alkaloid from the Caribbean sponge Stylissa caribica. J Nat Prod 64:1345–1347

    CAS  Google Scholar 

  9. Baden DG, Corbett MD (1980) Bromoperoxidases from Penicillus capitatus, Penicillus lamourouxii and Rhipocephalus phoenix. Biochem J 187:205–211

    CAS  Google Scholar 

  10. Bali DKL, Kiokas V, Garson MJ, Faulkner DJ (1990) Structural and stereochemical studies on brominated meroterpenoids from the dictyoceratid sponge Cacospongia sp. Aust J Chem 43:2009–2020

    CAS  Google Scholar 

  11. Bantleon R, Altenbuchner J, van Pée K-H (1994) Chloroperoxidase from Streptomyces lividans: isolation and characterization of the enzyme and the corresponding gene J Bacteriol 176:2339–2347

    CAS  Google Scholar 

  12. Blunt JW, Bowman NJ, Munro MHG, Parsons MJ, Wright GJ, Kon YK (1985) Polyhalogenated monoterpenes of the New Zealand marine red alga Plocamium cartilagineum. Aust J Chem 38:519–525

    CAS  Google Scholar 

  13. Boeynaems JM, Reagan D, Hubbard WC (1981) Lactoperoxidase-catalyzed iodination of arachidonic acid: formation of macrolides. Lipids 16:246–249

    CAS  Google Scholar 

  14. Boeynaems JM, Watson JT, Oates JA, Hubbard WC (1981) Iodination of docosahexaenoic acid by lactoperoxidase and thyroid gland in vitro: formation of an iodolactone. Lipids 16:323–327

    CAS  Google Scholar 

  15. Burd W, Yourkeviich O, Voskoboev AJ, van Pée K-H (1995) Purification and properties of a non-heme chloroperoxidase from Serratia marcescens. FEMS Microbiol Lett 129: 255–260

    CAS  Google Scholar 

  16. Butler A (1998) Vanadium peroxidases Curr Opinion Chem Biol 2:279–285

    CAS  Google Scholar 

  17. Byun J, Henderson JP, Mueller DM, Heineke JW (1999) 8-Nitro-2'-deoxyguanosine, a specific marker of oxidation by reactive nitrogen species, is generated by the myeloperoxidase hydrogen peroxide nitrite system of activated human phagocytes. Biochemistry 38:2590–2600

    CAS  Google Scholar 

  18. Cameron GM, Stapleton BL, Simonsen SM, Brecknell DJ, Garson MJ (2000) New sesquiterpene and brominated metabolites from the tropical marine sponge Dysidea sp. Tetrahedron 56:5247–5252

    CAS  Google Scholar 

  19. Carlson DJ, Lubencho J, Sparrow MA, Trowbridge CD (1989) Fine-scale variability of lanosol and its disulfate ester in the temperate red alga Neorhodomela larix. J Chem Ecol 15:1321–1333

    CAS  Google Scholar 

  20. Casella L, Poli S, Gullotti M, Selaggini C, Beringhelli T, Marchesini A (1994) The chloroper-oxidase-catalyzed oxidation of phenols. Mechanism, selectivity, and characterization of enzyme-substrate complexes Biochemistry 33:6377–6386

    CAS  Google Scholar 

  21. Chen TP, Woodin SA, Lincoln DE, Lovell CR (1996) An unusual dehalogenating peroxidase from the marine terebellid polychaete Amphitrite ornata. J Biol Chem 271:-4609–4612

    CAS  Google Scholar 

  22. Chen YP, Lincol DE, Woodin SA, Lovell CR (1991) Purification and properties of a unique flavin-containing chloroperoxidase from the capitellid polychaete Notomastus lobatus. J Biol Chem 266:23,909–23,915

    Google Scholar 

  23. Cheng X-C, Varoglu M, Abrell L, Crews P, Lobkovsky E, Clardy J (1994) Chloriolins A-C, chlorinated sesquiterpenes produced by fungal cultures separated from a Jaspis marine sponge. J Am Chem Soc 59:6344–6348

    CAS  Google Scholar 

  24. Chevolot L, Chevolot A-M, Gajhede M, Larsen C, Anthoni U, Christophersen C (1985) Chartelline A: a pentahalogemated alkaloid from the marine bryozoan Chartella pa-pyracea. J Am Chem Soc 107:4542–4543

    CAS  Google Scholar 

  25. Ciasullo L, Cutignano A, Casapullo A, Puliti R, Mattia CA, Debitus C, Gomez-Paloma L (2002) A new cycloamphilectene metabolite from the Vanuata sponge Axinella sp. J Nat Prod 65:1210–1212

    CAS  Google Scholar 

  26. Coll JC (1992) The chemistry and chemical ecology of octocorals (Coelenterata, Anthozoa, Octocorallia). Chem Rev 92:613–631

    CAS  Google Scholar 

  27. Cueto M, Darias J, Rovirosa J, San Martin A (1998) Unusual polyoxygenated monoterpenes from the Antarctic alga Pantoneura plocamioides. J Nat Prod 61:17–21

    CAS  Google Scholar 

  28. Dai MC, Garson MJ, Coll JC (1991) Biosynthetic processe in soft corals. I. A comparison of terpene biosynthesis in Alcyonium molle (Alcyonidea) and Heteroxenia sp. (Xeniidae). Comp Biochem Physiol 99B:775–783

    Google Scholar 

  29. Dairi T, Nakado T, Aisaka K, Katsumata R, Hasegawa M (1995) Cloning and nucleotide sequence of the gene responsible for chlorination of tetracycline. Biosci Biotech Biochem 59:1099–1106

    CAS  Google Scholar 

  30. Darias J, Rovisora J, San Martin A, Diaz A-R, Dorta E, Cueto M (2001) Furaplocamioids A-C, novel polyhalogenated furanoid monoterpenes from Plocamium cartilagineum. J Nat Prod 64:1383–1387

    CAS  Google Scholar 

  31. de Almeida Leone P, Redburn J, Hooper JNA, Quinn RJ (2000) Polyoxygenated Dysidea sterols that inhibit the binding of [1125] IL8 to the human recombinant IL-8 receptor type A. J Nat Prod 63:694–697

    Google Scholar 

  32. de Boer E, Tromp MGM, Plat H, Krenn BE, Wever R (1986) Vanadium (V) as an essential element for haloperoxidase activity in marine brown algae: purification and characterization of a vanadium (V)-containing bromoperoxidase from Laminaria saccharina Biochim Biophys Acta 872:104–115

    Google Scholar 

  33. de Nys R, Steinberg PD, Rogers CN, Charlton TS, Duncan MW (1996) Quantitative variation of secondary metabolites in the sea hare Aplysia parvula and its host plant Delisea pulchra. Mar Ecol Prog Ser 130:135–146

    CAS  Google Scholar 

  34. de Riccardis F, Iorizzi M, Minale L, Riccio R, de Forges BR, Debitus C (1991) The gymnochromes: novel marine phenanthroperylenequinone pigments from the stalked crinoid Gymnocrinus richeri. Org Chem 56:6781–6787

    Google Scholar 

  35. de Schrijver A, Nagy I, Schoofs G, Proost P, Vanderleyden J, van Pée K-H, de Mot R (1997) Thiocarbamate herbicide-indicible nonmheme haloperoxidase of Rhodococcus erythropolis NI86/21. Appl Environ Microbiol 63:1811–1916

    Google Scholar 

  36. de Wit CA (2002) An overview of brominated flame retardants in the environment. Chemosphere 46:583–624

    Google Scholar 

  37. di Blasio B, Fattorusso E, Magno S, Mayol L, Pedone C, Santacroce C, Sica D (1976) Axisonitrile-3, axisothiocyanate-3 and axamide-3. Sesquiterpenes with a novel spiro [4,5] decane skeleton from the sponge Axinella cannabina. Tetrahedron 32:473–478

    Google Scholar 

  38. Diop M, Samb A, Costantino V, Fattorusso E, Mangoni A (1996) A new iodinated metabolite and a new alkyl sulfate from the Senegalese sponge Ptilocaulis spiculifer. J Nat Prod 59:271–272

    CAS  Google Scholar 

  39. Dumdei EJ, Flowers AE, Garson MJ, Moore CJ (1997) The biosynthesis of sesquiterpene isocyanides and isothiocyanates in the marine sponge Acanthella cavernosa (Dendy); evidence for dietary transfer to the dorid nudibranch Phyllidiella pustulosa. Comp Biochem Physiol 118A:1385–1392

    Google Scholar 

  40. Dyrssen D, Fogelqvist E (1981) Bromoform concentrations of the Arctic Ocean in the Svalbard area. Oceanol Acta 4:313

    CAS  Google Scholar 

  41. Eiserich JP, Hristova M, Cross CE, Jones AD, Freeman BA, Halliwell B, van der Vliet A (1998) Formation of nitric oxide-derived inflammatory oxidants by myeloperoxidase in neutrophils. Nature (London) 391:393–397

    CAS  Google Scholar 

  42. Elyakov GB, Kuznetsova T, Mikhailov VV, Maltsev II, Voinov VG, Fedoreyev SA (1991) Brominated diphenyl ethers from a marine bacterium associated with the sponge Dysidea sp. Experientia 47:632–633

    CAS  Google Scholar 

  43. Encarnación RD, Sandoval E, Malmström J, Christophersen C (2000) Calafianin, a bromotrrosine derivative from the marine sponge Aplysina gerardogreeni. J Nat Prod

    Google Scholar 

  44. Estrada DM, Martin JD, Perez R, Rivera P, Rodriguez ML, Ruano JZ (1987) Furocaespitane and related C12 metabolites from Laurencia caespitosa. Tetrahedron Lett 28:687–688

    CAS  Google Scholar 

  45. Falch BS, König GM, Wright AD, Sticher O, Rüegger H, Bernardinelli G (1993) Ambigol A and B: new biologically active polychlorinated aromatic compounds from the terrestrial blue-gree alga Fischeralla ambigua. J Org Chem 58:6570–6575

    CAS  Google Scholar 

  46. Fenical W, Sleeper HW, Paul VJ, Stallard MO, Sun HO (1979) Defensive chemistry of Navanax and related opistobranch molluscs. Pure Appl Chem 51:1865–1874

    CAS  Google Scholar 

  47. Fielman KT, Woodin SA, Walla MD, Lincoln DE (1999) Widespread occurrence of natural halogenated organics among temperate marine infauna. Mar Ecol Prog Ser 181:1–12

    CAS  Google Scholar 

  48. Flodin C, Whitfield FB (1999) 4-Hydroxybenzoic acid: a likely precursor of 2,4,6-tribromophenol in Ulva lactuca Phytochem 51:249–255

    CAS  Google Scholar 

  49. Flodin C, Whitfield FB (1999) Biosynthesis of bromophenols in marine algae. Water Sci Technol 40 (6):53–58

    CAS  Google Scholar 

  50. Flodin C, Helidoniotis F, Whitfield FB (1999) Seasonal variation in bromophenol content and bromoperoxidase activity in Viva lactuca. Phytochem 51:135–138

    CAS  Google Scholar 

  51. Flodin C, Johansson E, Borén H, Grimvall A, Dahlman O, Mörck R (1997) Chlorinated structures in high molecular weight organic matter isolated from fresh and decaying plant material and soil. Environ Sei Technol 31:2464–2468

    CAS  Google Scholar 

  52. Flowers AE Garson MJ, Webb RI, Dumdei EJ, Charan RD (1998) Cellular origin of chlorinated diketopiperazines in the dictyoceratid sponge Dysidea herbacea (Keller). Cell Tissue Res 292:597–607

    CAS  Google Scholar 

  53. Fontana A, Mollo E, Ortea J, Gavagnin M, Cimino G (2000) Scalarane and homolscalarane compounds from the nudibranchs Glossodoris sedna and Glossodoris dalli: chemical and biological structures. J Nat Prod 63:527–530

    CAS  Google Scholar 

  54. Fu X, Ferreira MLG, Schmitz FJ, Kelly-Borges M (1998) New diketopiperazines from the sponge Dysidea chlorea. J Nat Prod 61:1226–1231

    CAS  Google Scholar 

  55. Fukuzawa A, Aya M, Murai A (1990) A direct enzymatic synthesis of laurencin from laurediol. Chem Lett 1579–1580

    Google Scholar 

  56. Fukuzawa A, Takasugi Y, Murai A, Nakamura M, Tamura M (1992) Enzymatic single-step formation of laureatin and its key intermediate prelaureatin from 3Z, 6S7S laurediol. Tetrahedron Lett 33:2017–2018

    CAS  Google Scholar 

  57. Furtmüller PG, Burner U, Regelsberger G, Obinger C (2000) Spectral and kinetic studies on the fomation of eosinophil peroxidase compound I and its reaction with halides and thiocyanate. Biochemistry 39:15,578–15,584

    Google Scholar 

  58. Gallard H, van Gunten U (2002) Chlorination of phenols: kinetics and formation of chloroform. Environ Sci Technol 36:884–890

    CAS  Google Scholar 

  59. Garson M J (1986) Biosynthesis of the novel diterpene isonitrile diisocyanoadociane by a marine sponge of the Amphimedon genus: incorporation studies with sodium [14C]cyanide and sodium [2-14C]acetate. J Chem Soc Chem Commun 35–36

    Google Scholar 

  60. Garson M (1993) The biosynthesis of marine products. Chem Rev 93:1699–1733

    CAS  Google Scholar 

  61. Geigert J, Neidleman SL, Dalietos DJ (1983) Novel haloperoxidase substrates. Alkynes and cyclopropanes. J Biol Chem 258:2273–2277

    CAS  Google Scholar 

  62. Geitler L (1932) Cyanophyseae. In: Kolkwitz R (ed) Krytogamenflora von Deutschland, Österreich und der Schweiz, vol. 14. Akademische Verlagsgesellschaft, Leipzig, pp 1–1196

    Google Scholar 

  63. Gerwick WH (1993) Carbocyclic oxylipins of marine origin. Chem Rev 93:1807–1823

    CAS  Google Scholar 

  64. Glombitza, K-W, Gerstberger G (1985) Phlorotannins with dibenzodioxin structural elements from the brown alga Eisenia arborea. Phytochem 254:543–551

    Google Scholar 

  65. Glombitza K-W, Schmidt A (1999) Nonhalogenated and halogenated phlorotannins from the brown alga Carpophyllum angustifolium. J Nat Prod 62:1238–1240

    CAS  Google Scholar 

  66. Glombitza K-W, Zieprath G (1989) Phlorotannins from the brown alga Analipus japoni-cus. Planta Med 55:171–175

    CAS  Google Scholar 

  67. Goetz GH, Harrigan GG, Likos J (2001) Ugibohlln: a new dibromo-seco-isophakellin from Axinella carteru J Nat Prod 64:1581–1582

    CAS  Google Scholar 

  68. Gribble GW (1996) Naturally occurring organohalogen compounds: a comprehensive survey. Prog Chem Org Nat Prod 68:1–498

    CAS  Google Scholar 

  69. Gribble GW (1998) Naturally occurring organohalogen compounds. Acc Chem Res 31:141–152

    CAS  Google Scholar 

  70. Gribble GW (1999) The diversity of naturally occurring organobromine compounds. Chem Soc Rev 28:335–346

    CAS  Google Scholar 

  71. Gribble GW (2002) Naturally occurring organofluorines. Handb Environ Chem 3N:121–136

    CAS  Google Scholar 

  72. Hacisalihoglu A, Jongejan JA, Duine JA (1997) Distribution of amine oxidases and amine dehydrogenases in bacteria grown on primary amines, characterization of the amine oxidase from Klebsiella oxytoca. Microbiology (UK) 143:505–512

    CAS  Google Scholar 

  73. Haglund PS, Zook DR, Buser H-R, Hu J (1997) Identification and quantification of polybrominated diphenyl ethers and methoxy-polybrominated diphenyl ethers in Baltic biota. Environ Sci Technol 31:3281–3287

    CAS  Google Scholar 

  74. Hamann MT, Scheuer PJ (1991) Cyanopuupehenol, an antiviral metabolite of a sponge of the order Verongida. Tetrahedron Lett 32:5671–5672

    CAS  Google Scholar 

  75. Hammer PE, Hill DS, Lam ST, van Pée K-H, Logon JM (1997) Four genes from Pseudomonas fluorescens that encode the biosynthesis of pyrrolnitrin. Appl Environ Microbiol 63:2147–2154

    CAS  Google Scholar 

  76. Hara I, Sakurai T (1998) Isolation and characterization of vanadium bromoperoxidase from a marine macroalga Ecklonia stolonifera. J Inorg Chem 72:23–28

    CAS  Google Scholar 

  77. Hargreaves J, Park J, Ghisalberti EL, Sivasithamparan K, Skelton BW, White AH (2002) New chlorinated diphenyl ethers from an Aspergillus species. J Nat Prod 65:7–10

    CAS  Google Scholar 

  78. Harper DB, Hamilton JTG (1988) Biosynthesis of chloromethane in Phellinus pomaceus J Gen Microbiol 134:2831–2839

    CAS  Google Scholar 

  79. Harrigan GG, Goetz GH, Luesch H, Yang S, Likos J (2001) Dysideaprolines A-F and barbaleucamides A-B, novel polychlorinated compounds from Dysidea sp. J Nat Prod 64:1133–1138

    CAS  Google Scholar 

  80. Härtung J (1999) The biosynthesis of barbamide a radical pathway for “biohalogenation”. Angew Chem Int Ed 38:1209–1211

    Google Scholar 

  81. Hecht HJ, Sobek H, Haag T, Pfeifer O, van Pée K-H (1994) The metal-ion-free oxidore-ductase from Streptomyces aureofaciens has an a/ß hydrolase fold. Struct Biol 1:532–537

    CAS  Google Scholar 

  82. Henderson JP, Byun J, Mueller DM, Heineke JW (2001) The eosinophil peroxidase — hydrogen peroxide — bromide system of human eosinophils generates 5-bromouracil, a mutagenic thymine analogue. Biochemistry 40:2052–2059

    CAS  Google Scholar 

  83. Higa T, Fujiyama T, Scheuer PJ (1980) Halogenated phenol and indole constituents of acorn worms. Comp Biochem Physiol 65B:525–530

    Google Scholar 

  84. Higa T, Okuda RK, Severns RM, Scheuer PJ, He C-H, Changfu X, Clardy J (1987) Un-precendented constituents of a new species of acorn worm. Tetrahedron 43:1063–1070

    CAS  Google Scholar 

  85. Hopper DJ, Cottrell L (2003) Alkylphenol biotransformations catalyzed by 4-ethylphenol methylenehyroxylase. Appl Environ Microbiol 69:3650–3652

    CAS  Google Scholar 

  86. Howard BM, Nomura AM, Fenical W (1980) Chemotaxonomy in marine algae: secondary metabolite synthesis by Laurencia in unialgal culture. Biochem Syst Ecol 8:329–336

    CAS  Google Scholar 

  87. Hu S, Dordick JS (2002) Highly enantioselective oxidation of cis-cyclopropylmethanols to corresponding aldehydes catalyzed by chloroperoxidase. J Org Chem 67:314–317

    CAS  Google Scholar 

  88. Hu S, Hager LP (1999) Highly enantioselective propargylic hydroxylations catalyzed by chloroperoxidase. J Am Chem Soc 121:872–873

    CAS  Google Scholar 

  89. Ichiba T, Nakao Y, Scheuer PJ, Sata NU, Kelly-Borges M (1995) Kumusine, a chloroadenine riboside from a sponge, Theonella sp. Tetrahedron Lett 36:3977–3980

    CAS  Google Scholar 

  90. Ishihara J, Shimada Y, Kanoh N, Takasugi Y, Fukuzawa A, Murai A (1997) Conversion of prelaureatin into laurallene, a bromo-allene compound by enzymatic and chemical bromo-etherification reactions. Tetrahedron 53:8371–8382

    CAS  Google Scholar 

  91. Itoh N, Shinya M (1994) Seasonal evolution of bromomethanes from corallina algae (Corallinaceae) and its effect on atmospheric ozone. Mar Chem 45:95–103

    CAS  Google Scholar 

  92. Itoh N, Morinaga N, Kouzai T (1994) Purification and characterization of a novel metal-containing nonheme bromoperoxidase from Pseudomonas putida. Biochim Biophys Acta 1207:208–216

    CAS  Google Scholar 

  93. Itoh N, Morinaga N, Nomura A (1992) A variety of catalases and bromoperoxidases in genus Pseudomonas and their characterization. Biochim Biophys Acta 1122:189–195

    CAS  Google Scholar 

  94. Itoh N, Quamrul Hasan AKM, Izumi Y, Yamada H (1988) Substrate specificity, regiospecificity and stereospecificity of halogenation reactions catalyzed by non-hemetype bromoperoxidase of Corallina pilulifera. Eur J Biochem 172:477–484

    CAS  Google Scholar 

  95. Itoh N, Sasaki H, Ohsawa N, Shibata MS, Miura J (1996) Bromoperoxidase in Corallina pilulifera is regulated by its vanadium content. Phytochemistry 42:277–281

    CAS  Google Scholar 

  96. Jenkins CL, Starr MP (1982) The brominated aryl-polyene (Xanthomonadin) pigments of Xanthomonas juglandis protect against photobiological damage. Curr Microbiol 7: 323–326

    CAS  Google Scholar 

  97. Jimenez JI, Scheuer P (2001) New lipopeptides from the Caribbean cyanobacterium Lyngbya majuscula. J Nat Prod 64:200–203

    CAS  Google Scholar 

  98. Jimenez JI, Huber U, Moore RE, Patterson GML (1999) Oxidized welwitindolinones from terrestrial Fischeralla spp. J Nat Prod 62:569–572

    CAS  Google Scholar 

  99. Jonas U, Hammer E, Haupt ETK, Schauer F (2000) Characterization of coupling products formed by biotransformation of biphenyl and diphenyl ether by the white rot fungus Pycnoporus cinnabarinus. Arch Microbiol 174:393–398

    CAS  Google Scholar 

  100. Jordan P, Vilter H (1991) Extraction of proteins from material rich in anionic mucilages: partition and fractionation of vanadate-dependent bromoperoxidases from the brown algae Laminaria digitata and L. saccharina in aqueous polymer two-phase systems. Biochim Biophys Acta 1073:98–106

    CAS  Google Scholar 

  101. Karuso P, Scheuer PJ (1989) Biosynthesis of isocyanoterpenes in sponges. J Org Chem 54:2092–2095

    CAS  Google Scholar 

  102. Kataoka M, Honda K, Shimizu S (2000) 3,4-Dihydrocoumarin hydrolase with haloperoxidase activity from Acinetobacter calcoaceticus. Eur J Biochem 267:3–10

    CAS  Google Scholar 

  103. Kazlauskas R, Murphy PT, Wells RJ (1982) A brominated metabolite from the red alga Vidalia spiralis, Aust J Chem 35:219–220

    CAS  Google Scholar 

  104. Kazunga C, Aitken MD, Gold A (1999) Primary product of the horseradish peroxidase-catalyzed oxidation of pentachlorophenol. Environ Sci Technol 33:1408–1412

    CAS  Google Scholar 

  105. Keller S, Wage T, Hohaus K, Hölzer M, Eichjorn E, van Pée K-H (2000) Purification and partial characterization of tryptophan 7-halogenase (PrnA) from Pseudomonas fluorescens. Angew Chem Int Ed 39:2300–2302

    CAS  Google Scholar 

  106. Khalil MAK (1999) Reactive chlorine compouds in the atmosphere. Handb Environ Chem 4E:45–79

    Google Scholar 

  107. King GM (1988) Dehalogenation in marine sediments containing natural sources of halophenols. Appl Environ Microbiol 54:3079–3085

    CAS  Google Scholar 

  108. Kirner S, Hammer PE, Hill DS, Altmann A, Fischer I, Weislo LJ, Lanahan M, van Pée K-H, Ligon JM (1998) Functions encoded by pyrrolnitrin biosynthetic genes from Pseudomonas fluorescens. J Bacteriol 180:1939–1943

    CAS  Google Scholar 

  109. Knowles RG, Moncada S (1994) Nitric oxide synthases in mammals. Biochem J 298:249–258

    CAS  Google Scholar 

  110. Kraus PFX, Kutchan TM (1995) Molecular cloning and heterologous expression of a cDNA encoding berbamine synthase, a C-0 phenol-coupling cytochrome P450 from the higher plant Berberis stolonifera. Proc Natl Acad Sei USA 92:2071–2075

    CAS  Google Scholar 

  111. Krenn BE, Izumi Y, Yamada H, Wever R (1989) A comparison of different (vanadium) peroxidases:the bromoperoxidase of Corallina pilulifera is also a vanadium enzyme. Biochim Biophys Acta 998:63–68

    CAS  Google Scholar 

  112. Kuniyoshi M, Marma MS, Higa T, Bernardinelli G, Jefford CW (2001) New bromoterpenes from the red alga Laurencia luzonensis. J Nat Prod 64:696–700

    CAS  Google Scholar 

  113. Kurata K, Taniguchi K, Takashima K, Hayashi I, Suzuki M (1997) Feeding-deterrent bromophenols from Odonthalia corymbifera. Phytochemistry 45:485–487

    CAS  Google Scholar 

  114. Kurata K, Taniguchi K, Agatsumas Y, Suzuki M (1998) Diterpenoid feeding-deterrents from Laurencia saitoi. Phytochemistry 47:363–369

    CAS  Google Scholar 

  115. Kurihara H, Mitani T, Kawabata J, Takahashi K (1999) Two new bromophenols from the red alga Odonthalia corymbifera. J Nat Prod 62:882–884

    CAS  Google Scholar 

  116. Kwak JH, Schmitz F J, Wolliams GC (2001) Milolides, new briarane diterpenoids from the Western Pacific octocoral Briareum stechi. J Nat Prod 64:754–760

    CAS  Google Scholar 

  117. Kylin H (1929) Über das Vorkommen von Jodiden, Bromiden und Jodidoxydasen bei den Meeresalgen. Z Physiol Chem 186:50–82

    CAS  Google Scholar 

  118. König GM, Wright AD (1997) Laurencia rigida: chemical investigations of its antifouling dichloromethane extract. J Nat Prod 60:967–970

    Google Scholar 

  119. LaCount MW, Zhang E, Chen YP, Han K, Whitton MM, Lincoln DE, Woodin SA, Lebioda L (2000) The crystal structure and amino acid sequence of dehaloperoxidase from Amphitrite ornata indicate common ancestry with globins. J Biol Chem 275:18,712–18,716

    Google Scholar 

  120. Lakner FJ, Hager LP (1996) Chloroperoxidase as enantioselective epoxidation catalyst:an efficient synthesis of (R)-(-) mevalonolactone. J Org Chem 61:3923–3925

    CAS  Google Scholar 

  121. Lawton LA, Morris LA, Jaspars M (1999) A bioactive modified peptide, aeruginosamide, isolated from the cyanobacterium Microcystis aeruginosa. J Org Chem 64:5329–5332

    CAS  Google Scholar 

  122. Li MKW, Scheuer PJ (1984) Halogenated blue pigments of a deep sea gorgonian Tetrahedron Lett 25:587–590

    CAS  Google Scholar 

  123. Libby RD, Thomas JA, Kaiser LW, Hager LP (1982) Chloroperoxidase halogenation reactions. Chemical versus enzymatic halogenation intermediates. J Biol Chem 257:5030–5037

    CAS  Google Scholar 

  124. Lim YJ, Park HS, Im KS, Lee C-O, Hong J, Lee M-Y, Kim D, Jung JE (2001) Additional cytotoxic polyacetylenes from the marine sponge Petrosia species. J Nat Prod 64:46–53

    CAS  Google Scholar 

  125. Lindel T, Hochgürtel M, Assmann M, Köck M (2000) Synthesis of the marine natural product N-a-(4-bromopyrrolyl-2-carbonyl)-L-homoarginine, a putative biogenic precursor of the pyrrole-imidazole alkaloids. J Nat Prod 63:1566–1569

    CAS  Google Scholar 

  126. Liu S, Fu X, Schmitz F J, Kelly-Borges M (1997) Psammaplysin F, a new bromotyrosine from a sponge, Aplysinella sp. J Nat Prod 60:614–615

    CAS  Google Scholar 

  127. Loo TL, Burger JW, Adamson RH (1964) Bromination of phthalein dyes by the uterus of the dogfish, Squalus acanthias. Proc Soc Exp Biol Med 114:60–63

    Google Scholar 

  128. Luesch H, Moore RE, Paul VJ, Mooberty SL, Corbett TH (2001) Isolation of dolastatin 10 from the marine cyanobacterium Symploca species VP642 and total stereochemistry and biological evaluation of its analogue symplostatin 1. J Nat Prod 64:907–910

    CAS  Google Scholar 

  129. Lukat GS, Goff HM (1990) A nuclear magnetic resonance study of axial ligation for the reduced states of chloroperoxidase, cytochrome P-450cam, and porphinatoiron(II) thiolate complexes. Biochim Biophys Acta 1037:351–359

    CAS  Google Scholar 

  130. Maia LF, de A Epifanio R, Eve T, Fenical W (1999) New fish deterrents, including a novel sequiterpenoid heterogorgiolide, from the Brazilian gorgonian Heterogorgia uatumani (Octocorallia, Gorgonacea). J Nat Prod 62:1322–1324

    CAS  Google Scholar 

  131. MacMillan JB, Molinski TF (2000) Herbacic acid, a simple prototype of 5,5,5-trichloroleucine metabolites from the sponge Dysidea herbacea. J Nat Prod 63:155–157

    CAS  Google Scholar 

  132. Manley SL, Dastoor MN (1987) Methyl halide (CH3X) production from the giant kelp Macrocystis, and estimates of global CH3X production by kelp. Limnol Oceanogr 32:709–715

    CAS  Google Scholar 

  133. Mann J (1987) Secondary metabolism, 2nd edn. Clarendon Press, Oxford

    Google Scholar 

  134. Manthey JA, Hager LP (1981) Purification and properties of bromoperoxidase from Penicillus capitatus. J Biol Chem 256:11,232–11,238

    Google Scholar 

  135. Martinez JS, Carroll GL, Tsirret-Guth RA, Altenhoff G, Little RD, Butler A (2001) On the regiospecificity of vanadium bromoperoxidase. J Am Chem Soc 123:3289–3294

    CAS  Google Scholar 

  136. Masuda M, Abe T, Sato S, Suzuki T, Suzuki M (1997) Diversity of halogenated secondary metabolites in the red alga Laurencia nipponica (Rhodomelaceae, Ceramiales). J Phycol 33:196–208

    CAS  Google Scholar 

  137. McConnell OJ, Fenical W (1980) Halogen chemistry of the red alga Bonnemaisonia. Phytochemistry 19:233–247

    CAS  Google Scholar 

  138. McPhail KL, Davies-Coleman MT, Copley RCB, Eggleston DS (1999) New halogenated sesquiterpenes from South African specimens of the circumtropical sea hare Aplysia dactylomela. J Nat Prod 62:1618–1623

    CAS  Google Scholar 

  139. Messerschmidt A, Prade L, Wever R (1997) Implications for the catalytic mechanism of the vanadium-containing enzyme chloroperoxodase from the fungus Curvularia inaequalis by X-ray structures of the native and peroxide form. Biol Chem 378:309–315

    CAS  Google Scholar 

  140. Milligan KE, Marquez BL, Williamson T, Gerwick W (2000) Lyngbyabellin B, a toxic and antifungal metabolites from the marine cyanonacterium Lyngbya majuscula. J Nat Prod 63:1440–1443

    CAS  Google Scholar 

  141. Mitchell SS, Pomerantz SC, Concepción GP, Ireland CM (1996) Tubercidin analogs from the acsidian Didemnum voelzkowi. J Nat Prod 59:1000–1001

    CAS  Google Scholar 

  142. Molinski TF, Faulkner DJ, van Duyne GD, Clardy J (1987) Three new diterpene isonitriles from a Palauan sponge of the genus Halichondria. J Org Chem 52:3334–3337

    CAS  Google Scholar 

  143. Moore CA, Okuda RK (1996) Bromoperoxidase activity in 94 species of marine algae. J Nat Toxins 5:295–305

    Google Scholar 

  144. Morris DR, Hager LP (1966) Chloroperoxidase. I. Isolation and properties of the crystalline protein J Biol Chem 241:1763–1768

    CAS  Google Scholar 

  145. Morris BD, Prinsep MR (1999) Amathaspiramides A-F, novel brominated alkaloids from the marine bryozoan Amathia wilsoni. J Nat Prod 62:688–693

    CAS  Google Scholar 

  146. Mtolera MS, Collen J, Pedersén M, Ekdahl A, Abrahamsson K, Semesi AK (1996) Stress-induced production of volatile halogenated organic compounds in Eucheuma denticulatum (Rhodophyta) caused by elevated pH and high light intensities. Eur J Phycol 31:89–95

    Google Scholar 

  147. Musman M, Tanaka J, Higa T (2001) New sesquiterpene carbonimidic dichlorides and related compounds from the sponge Stylotella aurantium. J Nat Prod 64:111–113

    CAS  Google Scholar 

  148. Myneni SCB (2002) Formation of stable chlorinated hydrocarbons in weathering plant material. Science 295:1039–1041

    CAS  Google Scholar 

  149. Neidleman SL, Geigert J (1986) Biohalogenation: principles, basic roles and applications. Ellis Horwood, Chichester, England

    Google Scholar 

  150. Neidleman SL, Levine SD (1968) Enzymatic bromohydrin formation. Tetrahedron Lett 4057–4059

    Google Scholar 

  151. Neilson AH (1980) Isolation and characterization of bacteria from the Baltic Sea. J Appl Bacteriol 49:199–213

    CAS  Google Scholar 

  152. Neilson AH, Hynning P-Â (1998) PAHs: products of chemical and biochemical transformation of alicyclic precursors. Handb Environ Chem 31:223–269

    Google Scholar 

  153. Nightingale PD, Malin G, Liss PS (1995) Production of chloroform and other low-molecular-weight halocarbons by some species of macroalgae. Limnol Oceanogr 40:680–689

    CAS  Google Scholar 

  154. Ohsawa N, Ogata Y, Okada N, Itoh N (2001) Physiological function of bromoperoxidase in the red marine alga, Corallina pilulifera: production of bromoform as an allelochemical and the simultaneous elimination of hydrogen peroxide. Phytochemistry 58:683–692

    CAS  Google Scholar 

  155. Ohshiro T, Nakano S, Takahashi Y, Suzuki M, Izumi Y (1999) Occurrence of bromoperoxidase in the marine green macro-alga, Ulvella lens, and emission of volatile brominated methane by the enzyme. Phytochem 52:1211–1215

    CAS  Google Scholar 

  156. Ohta T, Fujishoro K, Yamaguchi K, Tamura Y, Aisaka K, Uwajima T, Hasegawa M (1991) Sequence of gene choB encoding cholesterol oxidase of Brevibacterium sterolicum: comparison with choA of Streptomyces sp. SA-COO. Gene 103:93–96

    CAS  Google Scholar 

  157. Ohta T, Takahashi A, Matsuda M, Kamo S, Agatasuma T, Endo T, Nozoe S (1995) Russuphelol, a novel optically active chlorohydroquinone tetramer from the mushroom Russula subnigrificans. Tetrahedron Lett 5223–5226

    Google Scholar 

  158. Orjala J, Gerwick WH (1996) Barbamide, a chlorinated metabolite with molluscicidal activity from the Caribbean cyanobacterium Lyngbya majuscula. J Nat Prod 59:427–430

    CAS  Google Scholar 

  159. Ortiz de Montellano PR, Choe YS, DePillis G, Catalano CE (1987) Structure-mechanism relationships in hemoproteins. J Biol Chem 262:11,641–11,646

    Google Scholar 

  160. Pawlik JR, Chanas B, Toonen RJ, Fenical W (1995) Defenses of Caribbean sponges against predatory reef fish. I. Chemical deterrency. Mar Ecol Prog Ser 127:183–194

    CAS  Google Scholar 

  161. Pedersén M (1976) A brominating and hydroxylating peroxidase from the red alga Cystoclonium purpureum. Physiol Plant 37:6–11

    Google Scholar 

  162. Pedersén M, Fries N (1977) Bromophenols identified in a marine ascomycete and its culture medium Z Pflanzenphysiol 83:363–366

    Google Scholar 

  163. Pedersén M, Da Silva EJ (1973) Simple brominated phenols in the bluegreen alga Calothrix brevissima. Plant 115:83–86

    Google Scholar 

  164. Pedersén M, Saenger P, Fries L (1974) Simple brominated phenols in red algae. Phytochemistry 13:2273

    Google Scholar 

  165. Pelletier I, Altenbuchner J (1995) A bacterial esterase is homologous with non-haem haloperoxidases and displays brominating activity. Microbiology (UK) 141:459–468

    CAS  Google Scholar 

  166. Pew JC, Connors WJ (1969) New structures from enzymatic dehydrogenation of lignin model p-hydroxypropiophenones J Org Chem 34:585–589

    CAS  Google Scholar 

  167. Phillips MA, Towers GHN (1982) Chemical ecology of red algal bromophenols. I. Temporal, interpopulational, and within-thallus measuremenmts of lanosol levels in Rhodomela larix (Turner) C. Agardh. J Exp Mar Biol Ecol 58:285–293

    CAS  Google Scholar 

  168. Picard M, Gross J, Lubbert E, Tolzer S, Krauss S, van Pée K-H (1997) Metal-free haloperoxidases as ususual hydrolases: activation of H2O2 by the formation of peracetic acid. Angew Chem Int Ed 36:1196–1199

    CAS  Google Scholar 

  169. Poiner A, Paul VJ, Scheuner PJ (1989) Kumepaloxane. A rearranged trisnor sesquiterpene from the bubble shell Hamioea cymbalum. Tetrahedron 45:617–622

    CAS  Google Scholar 

  170. Poplawsky AR, Urban SC, Chun W (2000) Biological role of xanthomonadin pigments in Xanthomonas campestris pv. campestris. Appl Environ Microbiol 66:5123–5127

    CAS  Google Scholar 

  171. Ramakrishnan K, Oppenhuizen ME, Saunders S, Fischer J (1983) Stereoselectivity of chloroperoxidase-dependent halogenation. Biochemistry 22:3271–3277

    CAS  Google Scholar 

  172. Renganathan V, Miki K, Gold MH (1987) Haloperoxidase reactions catalyzed by lignin peroxidase, an extracellular enzyme from the basidiomycete Phanerochaete chrysosporium. Biochemistry 26:5127–5132

    CAS  Google Scholar 

  173. Renner MK, Jensen PR, Fenical W (1999) Neomangicols: structures and absolute stereochemistries of unprecendented halogenated sesterterpenes from a marine fungus of the genus Fusarium. J Org Chem 63:8346–8354

    Google Scholar 

  174. Renner MK, Jensen PR, Fenical W (2000) Mangicols: structures and biosynthesis of a new class of sesterterpene polyols from a marine fungus of the genus Fusarium. J Org Chem 65:4843–4852

    CAS  Google Scholar 

  175. Rezanka T, Dembitsky VM (1999) Brominated fatty acids from lichen Acorospora gobien-sis. Phytochemistry 50:97–99

    CAS  Google Scholar 

  176. Rezanka T, Dembitsky VM (2001) Bromoallenic lipid compounds from lichens of Central Asia. Phytochemistry 56:869–874

    CAS  Google Scholar 

  177. Rezanka T, Guschina IA (1999) Brominated depsidones from Acarospora gobiensis, a lichen of Central Asia. J Nat Prod 62:1675–1677

    CAS  Google Scholar 

  178. Rodriguez AD, Rodriguez C (2001) Serrulatane diterpenes with antimycobacterial activity isolated from the West Indian sea whip Pseudopterogorgonia elisabethae. J Nat Prod 64:100–102

    CAS  Google Scholar 

  179. Rogers CN, Steinberg PD, de Nys R (1995) Factors associated with oligophagy in two species of sea hares (Mollusca: Anaspidea). J Exp Mar Biol Ecol 192:47–73

    Google Scholar 

  180. Rudi A, Evan T, Aknin M, Kashman Y (2000) Polycitone B and prepolycitrin A: two novel alkaloids from the marine ascidian Polycitor africanus. J Nat Prod 63:832–833

    CAS  Google Scholar 

  181. Sampson JB, Ye YZ, Rosen H, Beckman JS (1998) Myeloperoxidase and horseradish peroxidase catalyze tyrosine nitration in proteins from nitrite and hydrogen peroxide. Arch Biochem Biophys 356:207–213

    CAS  Google Scholar 

  182. Sanduja R, Alam M, Wellimgton GM (1986) Secondary metabolites on the non-symbiotic coral Tubastraea micantha (Ehrenberg): isolation and structure of novel anthraquinoid derivatives. J Chem Res (S) 450–451

    Google Scholar 

  183. Schultz A, Jonas U, Hammer E, Schauer F (2001) Dehalogenation of chlorinated hydroxy-biphenyls by fungal laccase. Appl Environ Microbiol 67:4377–4381

    CAS  Google Scholar 

  184. Schupp P, Prokash P, Wray V (2002) Further new staurosporine derivatives from the ascidian Audistoma toealensis and its predatory flatworm Pseudoceros sp. J Nat Prod 65:295–298

    CAS  Google Scholar 

  185. Searle PA, Molinski TF (1995) Trachycladines A and B: 2'-C-methyl-5'deoxyribofurano-sylnucleosides from the marine sponge Trachycladus laevispirulifer. J Org Chem 60:4296–4298

    CAS  Google Scholar 

  186. Setchell WA, Gardner NL (1920) The marine algae of the pacific coast of North America. Part II. Chlorophyceae. University of California Publications in Botany, vol 8, no 2. University of California Press, Berkeley, p 295

    Google Scholar 

  187. Shen Z, Mitra SN, Wu W, Chen Y, Yang Y, Qin J, Hazen SL (2001) Eosinophil peroxidase catalyzes bromination of free nucleosides and double-stranded DNA. Biochemistry 40:2041–2051

    CAS  Google Scholar 

  188. Shimizu Y (1993) Microalgal metabolites. Chem Rev 93:1685–1698

    CAS  Google Scholar 

  189. Shimonishi M, Kuwamoto S, Inoue H, Wever R, Ohshiro T, Izumi Y, Tanabe T (1998) Cloning and expression of the gene for a vanadium-dependent bromoperoxidase from a marine macro-alga, Corallina pilulifera. FEBS Lett 428:105–110

    CAS  Google Scholar 

  190. Simons BH, Barnett P, Vollenbroek EGM, Dekker HL, Muijsers AO, Messerschmidt A, Wever R (1995) Primary structure and characterization of the vanadium chloroperoxidase from the fungus Curvularia inaequalis. Eur J Biochem 229:566–574

    CAS  Google Scholar 

  191. Simpson JS, Garson MJ (1998) Thiocyanate biosynthesis in the tropical marine sponge Axinyssa n. sp. Tetrahedron Lett 39:5819–5822

    CAS  Google Scholar 

  192. Simpson JS, Raniga P, Garson MJ (1997) Biosynthesis of dichloroimines in the tropical marine sponge Stylotella aurantium. Tetrahedron Lett 38:7947–7950

    CAS  Google Scholar 

  193. Singh ON, Fabian P (1999) Reactive bromine compounds. Handb Environ Chem 4E:1–43

    Google Scholar 

  194. Soedjak HS, Butler A (1990) Charactarization of vanadium bromoperoxidase from Macrocystis and Fucus: reactivity of bromoperoxidase towards acyl and alkyl peroxides and bromnation of amines. Biochemistry 29:7974–7981

    CAS  Google Scholar 

  195. Stallard MO, Faulkner DJ (1974) Chemical constituents of the digestive gland of the sea hare Aplysia californica. I. Importance of diet. Comp Biochem Physiol 49B:25–35

    CAS  Google Scholar 

  196. Stierle AC, Cardellina JH, Singleton FL (1988) A marine Micrococcus produces metabolites ascribed to the sponge Tedania ignis. Experientia 44:1021

    CAS  Google Scholar 

  197. Stratmann K, Moore RE, Bonjouklian R, Deeter JB, Patterson GML, Shaffer S, Smithmk CD, Smitka TA (1994) Welwitindolinones, unusual alkaloids from the blue-green algae Halalosiphon welwitschii and Westiella intricata. Relationship to fischerindoles and hapalindoles. J Am Chem Soc 116:9935–9942

    CAS  Google Scholar 

  198. Stubbe J, van der Donk WA (1998) Protein radicals in enzyme catalysis. Chem Revs 98:705–762

    CAS  Google Scholar 

  199. Sturges WT, Sullivan CW, Schnell RC, Heidt LE, Pollock WH (1993) Bromoalkane production by Antarctic ice algae Tellus 45B:120–126

    Google Scholar 

  200. Suenaga K, Shibata T, Takada N, Kigoshi H, Yamada K (1998) Aurilol, a cytotoxic bro-motriterpene isolated from the sea hare Dolabella auricularia. J Nat Prod 61:515–518

    CAS  Google Scholar 

  201. Sun HH, Paul VJ, Fenical W (1983) Avrainvilleol, a brominated diphenylmethane derivative with feeding deterrent properties from the tropical green alga Avrainvillea logicaulis. Phytochem 22:743

    CAS  Google Scholar 

  202. Sundaramoorthy M, Terner J, Poulos TL (1998) The crystal structure of chloroperoxidase: a heme peroxidase-cytochrome P450 functional hybrid. Structure 3:1367–1377

    Google Scholar 

  203. Sundaramoorthy M, Terner J, Poulos TL (1998) Stereochemistry of the chloroperoxidase active site: crystallographic and molecular-modeling studies. Chem Biol 5:461–473

    CAS  Google Scholar 

  204. Sundström J, Collen J, Abrahamsson K, Pedersén M (1996) Halocarbon production and in vivo brominating activity of Eucheuma denticulatum. Phytochemistry 42:1527–1530

    Google Scholar 

  205. Suzuki M, Matsuo Y, Takashi Y, Masuda M (1995) Callicladol, a novel cytoxic bromotriterpene polyether from a Vietnamese species of the red alga genus Laurencia. Chem Lett 1045–1046

    Google Scholar 

  206. Suzuki M, Daitoh M, Vairappan CS, Abe T, Masuda M (2001) Novel halogenated metabolites from the Malaysian Laurencia pannosa. J Nat Prod 64:597–602

    CAS  Google Scholar 

  207. Suzuki M, Yamada H, Kurata K (2002) Dictyterpenoids A and B, two novel diterpenoids with feeding deterrent activity from the brown alga Dilophus okamurae. J Nat Prod 65:121–125

    CAS  Google Scholar 

  208. Svenson A, Kjeller L-O, Rappe C (1989) Enzyme-mediated formation of 2,3,7,8-tetrasubstituted chlorinated dibenzodioxins and dibenzofurans. Environ Sei Technol 23: 900–902

    CAS  Google Scholar 

  209. Takahashi Y, Daitoh M, Suzuki M, Abe T, Masuda M (2002) Halogenated metabolites from the new Okinawan red alga Laurencia yonaguniensis. J Nat Prod 65:395–398

    CAS  Google Scholar 

  210. Tanaka J, Higa T (1999) Two new cytotoxic carbonimidic dichlorides from the nudibranch Reticulidiafungia. J Nat Prod 62:1339–1340

    CAS  Google Scholar 

  211. Thoma H, Rist S, Hauschulz G, Hutzinger O (1986) Polybrominated dibenzodioxins and -furans from the pyrolysis of some flame retardants. Chemosphere 15:649–652

    CAS  Google Scholar 

  212. Tilden J (1910) The Myxophyceae of North America and adjacent regions. Minneapolis, Minnesota

    Google Scholar 

  213. Tsukamoto S, Tane K, Ohta T, Matsunaga S, Fusetani N, van Soest RWM (2001) Four new bioactive pyrrole-derived alkaloids from the marine sponge Axinella brevistyla. J Nat Prod 64:1576–1578

    CAS  Google Scholar 

  214. Unson MD, Holland ND, Faulkner DJ (1994) A brominated secondary metabolite synthesized by the cyanobacterial symbiont of a marine sponge and accumulation of the crystalline metabolite in the sponge tissue. Mar Biol 119:1–11

    CAS  Google Scholar 

  215. Utkina NK, Denisenko VA, Scholokova OV, Virovaya MV, Gerasimenko AV, Popov DY, Krasokhin VB, Popov AM (2001) Spongiadioxins A and B, two new polybrominated dibenzo-p-dioxins from an Australian marine sponge Dysidea dendyi. J Nat Prod 64:151–153

    CAS  Google Scholar 

  216. Utkina NK, Denisenko VA, Scholokova OV, Virovaya MV, Scholokova OV, Prokof’eva NG (2002) New minor polybrominated dibenzo-p-dioxins from the marine sponge Dysidea dendyi. J Nat Prod 65:1213–1215

    CAS  Google Scholar 

  217. van der Vliet A, Eiserich JP, Halliwell B, Cross CE (1997) Formation of reactive nitrogen species during peroxidase-catalyzed oxidation of nitrite. J Biol Chem 272:7617–7625

    Google Scholar 

  218. van Pée K-H, Lingens F (1985) Purification and molecular catalytic properties of bromoperoxidase from Streptomyces phaeochromogenes J Gen Microbiol 131:1911–1916

    Google Scholar 

  219. van Pée K-H, Lingens F (1985) Purification of bromoperoxidase from Pseudomonas aureofaciens. J Bacteriol 161:1171

    Google Scholar 

  220. von Sydow LM, Nielsen AT, Grimvall AB, Borén HB (2000) Chloro- and bromacetates in natural archives of firn from Antarctica. Environ Sei Technol 34:239–245

    Google Scholar 

  221. Vetter W (2001) A GC/ECNI-MS method for the identification of lipophilic anthropogenic and natural brominated compounds in marine samples. Anal Chem 73:4951–495

    CAS  Google Scholar 

  222. Vetter W, Scholz E, Gaus C, Miller JF, Haynes D (2001) Anthropogenic and natural organohalogen compounds in blubber of dolphins and dugongs (Dugong dugong) from Northeastern Australia. Arch Environ Contam Toxicol 41:221–233

    CAS  Google Scholar 

  223. Vilter H (1984) Peroxidase from Phaeophyceae: a vanadium (V)-dependent peroxidase from Ascophyllum nodosum. Phytochem 23:1387–1390

    CAS  Google Scholar 

  224. Vogt R (1999) Iodine compounds in the atmosphere. Handb Environ Chem 4E:113–128

    Google Scholar 

  225. Watanabe K, Sekine M, Takahashi H, Iguchi K (2001) New halogenated marine prostanoids with cytotoxic activity from the Okinawan soft coral Clavularia viridis. J Nat Prod 64:1421–1425

    CAS  Google Scholar 

  226. Watling R, Harper DB (1998) Chloromethane production by wood-rotting fungi and an estimate of the global flux to the atmosphere. Mycol Res 102:769–787

    CAS  Google Scholar 

  227. Weng M, Pfeifer O, Kraus S, Lingens F, van Pée K-H (1991) Purification, characterization and comparison of two non-heme bromoperoxidases from Streptomyces aureofaciens. J Gen Microbiol 137:2539–2546

    CAS  Google Scholar 

  228. Wessels M, König GM, Wright AD (2000) New natural product isolation and comparison of the secondary metabolite content of three distinct samples of the sea hare Aplysia dactylomela from Tenerife. J Nat Prod 63:920–928

    CAS  Google Scholar 

  229. Wever R, Tramp MGM, Krenn BE, Marjani A, Van Toi M (1991) Brominating activity of the seaweed Ascophyllum nodosum: impact on the biosphere. Environ Sci Technol 25:446–449

    CAS  Google Scholar 

  230. Whitfield FB, Drew M, Helidoniotis F, Svoronos D (1999) Distribution of bromophenols in species of marine algae from Eastern Australia. J Agric Food Chem 47:2367–2373

    CAS  Google Scholar 

  231. Whitfield FB, Drew M, Helidoniotis F, Svoronos D (1999) Distribution of bromophenols in species of ocean fish from Eastern Australia. J Agric Food Chem 47:3750–3757

    Google Scholar 

  232. Whitfield FB, Drew M, Helidoniotis F, Svoronos D (1999) Distribution of bromophenols in species of marine polychaetes and bryozoans from Eastern Australia and the role of such animals in the flavor of edible ocean fish and prawns (shrimp). J Agric Food Chem 47:4756–4862

    CAS  Google Scholar 

  233. Wiemer DF, Idler DD, Fenical W (1991) Vidalols A and B, new anti-inflammatory bromophenols from the Carribean marine red alga Vidalia obtusaloba. Experientia 47:851

    CAS  Google Scholar 

  234. Wiesner W, van Pée K-H, Lingens F (1988) Purification and characterization of a novel non-heme chloroperoxoidase from Pseudomonas pyrrocinia. J Biol Chem 263:13,725–13,732

    Google Scholar 

  235. Wilson DM, Puyana M, Fenical W, Pawlik JR (1999) Chemical defense of the Caribbean reef sponge Axinella corrugata against predatory fishes. J Chem Ecol 25:2811–2823

    CAS  Google Scholar 

  236. Wolf D, Schmitz FJ (1998) New diterpene isonitriles from the sponge Phakellia pulcherrima. J Nat Prod 61:1524–1527

    CAS  Google Scholar 

  237. Wolf D, Schmitz FJ, Hossain MB, van der Helm D (1999) Aplidioxins A and B two new dibenzo-p-dioxins from the ascidian Aplidiopsis ocellata. J Nat Prod 62:167–169

    CAS  Google Scholar 

  238. Woodin SA, Marinelli RL, Lincoln DE (1993) Allelochemical inhibition of recruitment in a sedimentary assemblage. J Chem Ecol 19:517–530

    CAS  Google Scholar 

  239. Wratten SJ, Faulkner JD (1977) Carbonimidic dichlorides from the marine sponge Pseudaxinyssa pitys. J Am Chem Soc 99:7367–7368

    CAS  Google Scholar 

  240. Wu W, Chen Y, d’Avignon A, Hazen SL (1999) 3-Bromotyrosine and 3,5-dibromotyrosine are major products of protein oxidation by eosinophil peroxidase: potential markers for eosinophil-dependent tissue injury in vivo. Biochemistry 38:3538–3548

    CAS  Google Scholar 

  241. Wuosmaa AM, Hager LP (1990) Methyl chloride transferases carbocation route for biosynthesis of halometabolites Science 249:160–163

    CAS  Google Scholar 

  242. Yoshikawa K, Kanekuni S, Hanahusa M, Arihara S, Ohta T (2000) Polyhydroxylated sterols from the octocoral Dendronephthya gigantea. J Nat Prod 63:670–672

    CAS  Google Scholar 

  243. Zeiner R, van Pée K-H, Lingens F (1988) Purification and partial characterization of multiple bromoperoxidases from Streptomycesgriseus. J Gen Microbiol 134:3141–3149

    CAS  Google Scholar 

  244. Zjawiony JK, Bartyzel P, Hamann MT (1998) Chemistry of puupehenone: 1,6-conjugate addition to its quinone-methide system. J Nat Prod 61:1502–1508

    CAS  Google Scholar 

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Neilson, A.H. (2003). Biological Effects and Biosynthesis of Brominated Metabolites. In: Neilson, A.H. (eds) Organic Bromine and Iodine Compounds. The Handbook of Environmental Chemistry, vol 3R. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-540-37055-0_2

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