Natural halogenated fatty acids: their analogues and derivatives.

A comprehensive survey has been made of all fatty acids containing halogen atoms covalently bonded to carbon and which are deemed as naturally occurring. Generally thought to be minor components produced by many different organisms, these interesting compounds now number more than 300. Recent research, especially in the marine area, indicates this number will increase in the future. Sources of halogenated fatty acids include microorganisms, algae, marine invertebrates, and higher plants and some animals. Their possible biological significance has also been discussed

[1]  G. Guella,et al.  Raspailynes, Novel Long‐Chain Acetylenic Enol Ethers of Glycerol from the Marine Sponges Raspailia pumila and Raspailia ramosa , 1987 .

[2]  C. L. Davies,et al.  Distribution of chlorosulpholipids in algae , 1979 .

[3]  H. Schmid,et al.  N-acylated glycerophospholipids and their derivatives. , 1990, Progress in lipid research.

[4]  J. Hutchinson,et al.  Flora of West Tropical Africa , 1931, Nature.

[5]  K. van Pée,et al.  Purification and partial characterization of multiple bromoperoxidases from Streptomyces griseus. , 1988, Journal of general microbiology.

[6]  W. Gerwick,et al.  Lyngbyabellin B, a toxic and antifungal secondary metabolite from the marine cyanobacterium Lyngbya majuscula. , 2000, Journal of natural products.

[7]  K. van Pée,et al.  Purification and properties of bromoperoxidase from Pseudomonas pyrrocinia. , 1985, Biological chemistry Hoppe-Seyler.

[8]  A. Mattocks Chemistry and Toxicology of Pyrrolizidine Alkaloids , 1986 .

[9]  C. Walsh,et al.  Stereochemical outcome of processing of fluorinated substrates by ATP citrate lyase and malate synthase. , 1981, Biochemistry.

[10]  J. Braekman,et al.  Chemical defence in sponges , 1986 .

[11]  Tsuyoshi Fukuhara,et al.  Stereo- and regioselective synthesis of (E,E)-δ-fluoro-α,β,γ,δ-unsaturated carbonyl compounds by Heck-type reaction of fluoroalkenyliodonium salts , 2000 .

[12]  Richard E. Moore,et al.  Volatile halogen compounds in the alga Asparagopsis taxiformis (Rhodophyta) , 1976 .

[13]  H. Hirota,et al.  Aurantosides A and B: cytotoxic tetramic acid glycosides from the marine sponge Theonella sp , 1991 .

[14]  W. Mendelson,et al.  Characterization of the hypnotic properties of oleamide. , 1999, Neuroreport.

[15]  M. Kelly-Borges,et al.  Sponge‐Derived Polyunsaturated C16 Di‐ and Tribromocarboxylic Acids , 1993 .

[16]  M. Franssen,et al.  The chlorination of barbituric acid and some of its derivatives by chloroperoxidase. , 1987 .

[17]  C. Culvenor,et al.  The Alkaloids of Senecio jacobaea L. , 1954 .

[18]  D. O'Hagan,et al.  The fluorinated natural products. , 1994, Natural product reports.

[19]  K. Iguchi,et al.  Chlorovulones, new halogenated marine prostanoids with an antitumor activity from the stolonifer clavularia viridis Quoy and Gaimard , 1985 .

[20]  Dr. Siegfried Huneck,et al.  Identification of Lichen Substances , 1996, Springer Berlin Heidelberg.

[21]  T. Ohta,et al.  A chlorohydrin amino acid from Amanita abrupta , 1987 .

[22]  E. Kun,et al.  Studies with specific enzyme inhibitors. XII. Resolution of DL-erythro-fluorocitric acid into optically active isomers. , 1969, The Journal of biological chemistry.

[23]  K. van Pée,et al.  Purification and properties of a nonheme bromoperoxidase from Streptomyces aureofaciens. , 1987, Biological chemistry Hoppe-Seyler.

[24]  S. D. Rosa,et al.  Further High Molecular Weight Polyacetylenes from the Sponge Petrosia ficiformis , 1985 .

[25]  W. Chilton,et al.  A chloro amino acid from Amanita solitaria , 1972 .

[26]  Chien-Kuang Chen,et al.  Total synthesis of 7,7-, 10-10-, and 13,13-difluoroarachidonic acids , 1987 .

[27]  Richard E. Moore,et al.  Volatile compounds from marine algae , 1977 .

[28]  A. Bermond,et al.  Characterization of Chlorination By-products in Cooling Effluents of Coastal Nuclear Power Stations , 1999 .

[29]  J. Elovson,et al.  A new class of lipids: chlorosulfolipids. , 1969, Proceedings of the National Academy of Sciences of the United States of America.

[30]  B. Alvarado,et al.  Two malyngamides from the Caribbean cyanobacterium Lyngbya majuscula , 1987 .

[31]  R. Sheldon,et al.  Improving the catalytic performance of peroxidases in organic synthesis. , 2001, Trends in biotechnology.

[32]  G. Sandberg,et al.  Identification of 4-chloroindole-3-acetic acid and indole-3-aldehyde in seeds of Pinus sylvestris. , 1986 .

[33]  M. Stuart,et al.  13-Hydroxyoctadeca-9,11-dienoic acid (13-HODE) inhibits thromboxane A2 synthesis, and stimulates 12-HETE production in human platelets. , 1987, Biochemical and biophysical research communications.

[34]  M. Lagarde,et al.  13-Hydroxyoctadecadienoic acid is the vessel wall chemorepellant factor, LOX. , 1985, Journal of Biological Chemistry.

[35]  G. Ewald Chlorinated fatty acids - Environmental pollutants with intriguing properties , 1998 .

[36]  K. van Pée,et al.  Purification, characterization and comparison of two non-haem bromoperoxidases from Streptomyces aureofaciens ATCC 10762. , 1991, Journal of general microbiology.

[37]  W. Fenical,et al.  Halogen chemistry of the red alga Asparagopsis , 1977 .

[38]  C. L. Davies,et al.  Chlorosulpholipids of Tribonema aequale , 1974 .

[39]  W. D. Hewson,et al.  BROMOPEROXIDASES AND HALOGENATED LIPIDS IN MARINE ALGAE 1 , 1980 .

[40]  C. Bewley,et al.  Theopalauamide, a Bicyclic Glycopeptide from Filamentous Bacterial Symbionts of the Lithistid Sponge Theonella swinhoei from Palau and Mozambique , 1998 .

[41]  C. L. Davies,et al.  Chlorosulpholipids in algae , 1975 .

[42]  C. Litchfield,et al.  Unusual C24, C25, C26 and C27 polyunsaturated fatty acids of the marine sponge Microciona prolifera. , 1976, Biochimica et biophysica acta.

[43]  T. Řezanka,et al.  Brominated fatty acids from lichen Acorospora gobiensis , 1999 .

[44]  R. Grée,et al.  Synthesis of Fluorinated Analogs of Polyunsaturated Fatty Acid Metabolites (4 HNE, 13 HODE) , 1997 .

[45]  J. Nakayama,et al.  Structure and stereochemistry of three phytotoxins, syringomycin, syringotoxin and syringostatin, produced by Pseudomonas syringae pv. syringae , 1992 .

[46]  K. van Pée,et al.  Purification and molecular and catalytic properties of bromoperoxidase from Streptomyces phaeochromogenes. , 1985, Journal of general microbiology.

[47]  J. Hamilton,et al.  Mechanisms for ion formation during the electron impact-mass spectrometry of picolinyl ester and 4,4-dimethyloxazoline derivatives of fatty acids. , 2000, Chemistry and physics of lipids.

[48]  C. Chidester,et al.  The isolation, structure, and absolute configuration of U-43,795, a new antitumor agent. , 1975, The Journal of antibiotics.

[49]  J. R. Medina,et al.  New delta 5,9 fatty acids in the phospholipids of the sea anemone Stoichactis helianthus. , 1994, Journal of natural products.

[50]  Woolley,et al.  The uptake of fluoride by Acacia georginae F.M. Bailey , 1968 .

[51]  W. Fenical,et al.  Halogen chemistry of the red alga Bonnemaisonia , 1980 .

[52]  K. Iguchi,et al.  New halogenated marine prostanoids with cytotoxic activity from the Okinawan soft coral Clavularia viridis. , 2001, Journal of natural products.

[53]  M. Henze Zur Kenntnis der jodbindenden Gruppe der natürlich vorkommenden Jodeiweißkörper. Die Konstitution der Jodgorgosäure. , 1907 .

[54]  G. Odham,et al.  Chlorinated fatty acids in membrane lipids of fish , 1998, Naturwissenschaften.

[55]  R. L. Fletcher Epiphytism and fouling in Gracilaria cultivation: an overview , 1995, Journal of Applied Phycology.

[56]  S. H. Wollman,et al.  Control of the Thyroid Gland , 1989, Advances in Experimental Medicine and Biology.

[57]  F. Gunstone,et al.  Fatty Acid and Lipid Chemistry , 1996, Springer US.

[58]  A. Zheleva,et al.  Four new coumarins from the roots of Peucedanum arenarium , 1976 .

[59]  T. Morikawa,et al.  Studies on organic fluorine compounds. LIV: Synthesis of 2,2-difluoroarachidonic acid , 1989 .

[60]  J. Wolff Excess iodide inhibits the thyroid by multiple mechanisms. , 1989, Advances in experimental medicine and biology.

[61]  N. Carballeira,et al.  Identification of a new 6-bromo-5,9-eicosadienoic acid from the anemone Condylactis gigantea and the zoanthid Palythoa caribaeorum. , 1995, Journal of natural products.

[62]  Johnson Ae,et al.  Toxicity of Riddell's groundsel (Senecio riddellii) to cattle. , 1985 .

[63]  H. Kawai,et al.  Thiazohalostatin, a new cytoprotective substance produced by Actinomadura. II. Physico-chemical properties and structure determination. , 1993, The Journal of antibiotics.

[64]  D. G. Daniels Changes in the lipids of flour induced by treatment with chlorine dioxide or chlorine, and on storage , 1960 .

[65]  K. Ballschmiter,et al.  Biohalogenation as a source of halogenated anisoles in air , 1991 .

[66]  P. Aisen,et al.  Circulating hydroxy fatty acids in familial Mediterranean fever. , 1985, Proceedings of the National Academy of Sciences of the United States of America.

[67]  K. van Pée,et al.  Purification of bromoperoxidase from Pseudomonas aureofaciens , 1985, Journal of bacteriology.

[68]  C. Djerassi,et al.  Phospholipid studies of marine organisms. 22. Structure and biosynthesis of a novel brominated fatty acid from a hymeniacidonid sponge , 1989 .

[69]  D. Morris,et al.  Chloroperoxidase. I. Isolation and properties of the crystalline glycoprotein. , 1966, The Journal of biological chemistry.

[70]  J. L. Smith,et al.  [R-(Z)]-4-amino-3-chloro-2-pentenedioic acid, a new antibiotic. Fermentation, isolation and characterization. , 1984, The Journal of antibiotics.

[71]  H. Abé,et al.  Isolation of a Novel Auxin, Methyl 4-Chloroindoleacetate from Immature Seeds of Pisum sativum , 1968 .

[72]  I. Tinsley,et al.  Bromine content of lipids of marine organisms , 1980 .

[73]  V. Macko,et al.  Structure of the host-specific toxins produced by the fungal pathogen Periconia circinata. , 1992, Proceedings of the National Academy of Sciences of the United States of America.

[74]  S. Matsunaga,et al.  Isolation of Four New Calyculins from the Marine Sponge Discodermia calyx , 1997 .

[75]  W. Fenical HALOGENATION IN THE RHODOPHYTA 1, 2 A REVIEW , 1975 .

[76]  R. Peters,et al.  Further observations upon the toxic principle of Dichapetalum toxicarium , 1959 .

[77]  V. Dembitsky,et al.  Lipids of lichens. , 1992, Progress in lipid research.

[78]  B. Verdcourt,et al.  Common poisonous plants of East Africa , 1970 .

[79]  J. Casida,et al.  Iodine metabolism in insects. I. In vivo metabolism of radio-iodide. , 1957, The Journal of experimental zoology.

[80]  M. Okuhara,et al.  FR-900148, A NEW ANTIBIOTIC , 1980 .

[81]  G. Odham,et al.  Occurrence of halogenated fatty acids in bivalve lipids , 1995 .

[82]  E. Mercer,et al.  Occurrence of a 3′-phosphoadenosine 5′-Phosphosulphate synthesizing system In two Ochromonas species , 1974 .

[83]  C. Wesén,et al.  Halogenated fatty acids: I. Formation and occurrence in lipids , 1997 .

[84]  E. Allain,et al.  Highly Enantioselective Epoxidation of Disubstituted Alkenes with Hydrogen Peroxide Catalyzed by Chloroperoxidase. , 1993 .

[85]  G. Sassaki,et al.  Fatty acid composition of lipids present in selected lichenized fungi: A chemotyping study , 2001, Lipids.

[86]  J. Westley,et al.  Brominated polyacetylenic acids from the marine sponge Xestospongia muta: inhibitors of HIV protease. , 1992, Journal of natural products.

[87]  D. Tucker,et al.  Further Acetylenic Acids from the Marine Sponge Xestospongia testudinaria , 1991 .

[88]  D. Tucker,et al.  A brominated bisacetylenic acid from the marine sponge Xestospongia testudinaria , 1985 .

[89]  Richard E. Moore,et al.  Haloforms in the essential oil of the alga asparagopsis taxiformis (rhodophyta) , 1975 .

[90]  K. E. Everse,et al.  Peroxidases in chemistry and biology , 1990 .

[91]  R. Keck,et al.  Synthesis of stereospecifically deuterated fluoroacetic acid and its behaviour in enzymic aldol‐type condensations , 1980, FEBS letters.

[92]  M. Jägerstad,et al.  Inhibitory effect of threo-9,10-dichlorostearic acid on the mutagenic activity of MeIQx, 2-AF and B[a]P in the Ames/Salmonella test. , 1998, Mutation research.

[93]  R. Wever,et al.  The chloroperoxidase from the fungus Curvularia inaequalis; a novel vanadium enzyme. , 1993, Biochimica et biophysica acta.

[94]  F. Bossa,et al.  The structure of syringomycins A1, E and G , 1989, FEBS letters.

[95]  R. Barrow,et al.  Carduusynes (A-E) - Acetylenic Acids From a Great-Australian-Bight Marine Sponge Phakellia-Carduus , 1994 .

[96]  P. C. Kearney,et al.  Degradation of herbicides , 1969 .

[97]  J. Kirk,et al.  Reactions of Aqueous Chlorine and Chlorine Dioxide with Lipids: Chlorine Incorporation , 1982 .

[98]  J. Clark,et al.  On oxyhalogenation, acids, and non-mimics ofbromoperoxidase enzymes , 2000 .

[99]  K. van Pée,et al.  Detection of a new chloroperoxidase in Pseudomonas pyrrocinia , 1986, FEBS letters.

[100]  N. Carballeira,et al.  Novel brominated phospholipid fatty acids from the Caribbean sponge Petrosia sp. , 1993, Journal of natural products.

[101]  J. Baker Some Metabolites from Australian Marine Organisms , 1976 .

[102]  J. Fried,et al.  Enzymatic conversions of 10,10-difluoroarachidonic acid with PGH synthase and soybean lipoxygenase , 1987 .

[103]  C. Djerassi,et al.  Phospholipid studies of marine organisms 9. New brominateddemospongic acids from the phospholipids of two species , 1984 .

[104]  N. Harada,et al.  UNSATURATED HYDROXY FATTY ACIDS, THE SELF DEFENSIVE SUBSTANCES IN RICE PLANT AGAINST RICE BLAST DISEASE , 1984 .

[105]  N. Sheppard,et al.  The chemical nature of the toxic compounds containing fluorine in the seeds of Dichapetalum toxicarium. , 1960, The Biochemical journal.

[106]  B. Brunström,et al.  In vivo and in vitro toxicity of fractionated fish lipids, with particular regard to their content of chlorinated organic compounds. , 1991, Pharmacology & toxicology.

[107]  T. Řezanka,et al.  Bromoallenic lipid compounds from lichens of central Asia. , 2001, Phytochemistry.

[108]  J. Paasiv́irta,et al.  Chlorinated acetic and propionic acids in pine needles from industrial areas , 1998 .

[109]  Richard E. Moore,et al.  Mirabimide E, an Unusual N-Acylpyrrolinone from the Blue-Green Alga Scytonema mirabile: Structure Determination and Synthesis , 1994 .

[110]  H. Scholl,et al.  Trichloroacetic acid in conifer needles in Finland , 1992 .

[111]  S. Ohta,et al.  Clathrynamides A, B, and C: Novel amides from a marine sponge Clathria sp. That inhibit cell division of fertilized starfish eggs , 1993 .

[112]  V. Dembitsky Betaine ether-linked glycerolipids: chemistry and biology. , 1996, Progress in lipid research.

[113]  Siuda Jf,et al.  Naturally occurring halogenated organic compounds. , 1973 .

[114]  R. Voss,et al.  An improved solvent-extraction based procedure for the gas chromatographic analysis of resin and fatty acids in pulp mill effluents , 1985 .

[115]  S. Neidleman,et al.  Biohalogenation : principles, basic roles, and applications , 1986 .

[116]  P. Scheuer Marine Natural Products , 1996 .

[117]  K. van Pée,et al.  Purification and characterization of a novel bacterial non-heme chloroperoxidase from Pseudomonas pyrrocinia. , 1988, The Journal of biological chemistry.

[118]  G. Blondin ISOLATION, PROPERTIES, AND STRUCTURAL FEATURES OF DIVALENT CATION IONOPHORES DERIVED FROM BEEF HEART MITOCHONDRIA fn1 , 1975, Annals of the New York Academy of Sciences.

[119]  Y. Ohizumi,et al.  Penaresin, a new sarcoplasmic reticulum Ca-inducer from the Okinawan marine sponge Penares sp. , 1990 .

[120]  B. Griffin,et al.  Chlorination of NADH: similarities of the HOCl-supported and chloroperoxidase-catalyzed reactions. , 1985, Archives of biochemistry and biophysics.

[121]  A. Holmes Arsenic content of American cod liver oil. , 1934 .

[122]  Richard E. Moore,et al.  Halogenated acetamides, but-3-en-2-ols, and isopropanols from asparagopsis taxiformis (delile) trev , 1976 .

[123]  G. Gribble The Diversity of Natural Organochlorines in Living Organisms , 1996 .

[124]  H. Sobek,et al.  The metal-ion-free oxidoreductase from Streptomyces aureofaciens has an α/β hydrolase fold , 1994, Nature Structural Biology.

[125]  S. Forenza,et al.  New bromo-pyrrole derivatives from the sponge Agelas oroides , 1971 .

[126]  M. Henze Zur Geschichte der Jodgorgosäure. , 1911 .

[127]  H. Abé,et al.  Isolation of 4-Chloroindolyl-3-acetic Acid from Immature Seeds of Pisum sativum , 1968, Nature.

[128]  M. Remberger,et al.  Gas chromatographic analysis and gas chromatographic—mass spectrometric identification of components in the cyclohexane-extractable fraction from contaminated sediment samples , 1990 .

[129]  T. Allen,et al.  Biologically active metabolites from Agelas mauritiana , 1988 .

[130]  S. Pan,et al.  The enzymatic halogenation of steroids. , 1966, Tetrahedron letters.

[131]  T. Řezanka,et al.  Fatty acids and phospholipids from lichens of the order lecanorales , 1992 .

[132]  J. Hunter-Cevera,et al.  Isolation and characterization of a novel nonheme chloroperoxidase. , 1987, Biochemical and biophysical research communications.

[133]  H. Scholl,et al.  Trichloroacetic acid in the foliage of forest trees. , 1990 .

[134]  M. Ishibashi,et al.  MANZACIDINS A-C, NOVEL TETRAHYDROPYRIMIDINE ALKALOIDS FROM THE OKINAWAN MARINE SPONGE HYMENIACIDON SP. , 1991 .

[135]  M. Okuhara,et al.  FR-900148, a new antibiotic. II. Structure determination of FR-900148. , 1980, The Journal of antibiotics.

[136]  Tomáš Dvořáčková Blanka Novák,et al.  Enrichment of chlorinated fatty acids in fish lipids prior to analysis by capillary gas chromatography with electrolytic conductivity detection and mass spectrometry , 1996 .

[137]  R. Sheldon,et al.  Selective oxygen transfer catalysed by heme peroxidases: synthetic and mechanistic aspects. , 2000, Current opinion in biotechnology.

[138]  D. Schomburg,et al.  Crystallization and preliminary X-ray data of bromoperoxidase from Streptomyces aureofaciens ATCC 10762. , 1991, Journal of molecular biology.

[139]  C. Watts,et al.  Chlorination of fatty acids during water treatment disinfection: Reactivity and product identification , 1986 .

[140]  Ronald R. Cowden,et al.  Aspects of Sponge Biology , 1976 .

[141]  J. Littlechild Haloperoxidases and their role in biotransformation reactions. , 1999, Current opinion in chemical biology.

[142]  K. Gibson,et al.  Identification of novel hydroxy fatty acids in the barnacle Balanus balanoides. , 1990, Biochimica et biophysica acta.

[143]  S. Neidleman,et al.  Novel haloperoxidase substrates. Alkynes and cyclopropanes. , 1983, The Journal of biological chemistry.

[144]  B. Vickery,et al.  Analysis of plants for fluoroacetic acids , 1973 .

[145]  Richard E. Moore,et al.  Halogenated acetic and acrylic acids from the red alga Asparagopsis taxiformis , 1979 .

[146]  G. Lunde Analysis of arsenic and bromine in marine and terrestrial oils , 1972, Journal of the American Oil Chemists' Society.

[147]  K. Shindo,et al.  Thiazohalostatin, a new cytoprotective substance produced by Actinomadura. I. Taxonomy, production, isolation and biological activities. , 1993, Journal of antibiotics (Tokyo. 1968).

[148]  R. White,et al.  Occurrence of fatty acid chlorohydrins in jellyfish lipids. , 1977, Biochemistry.

[149]  T. Řezanka,et al.  Polyhalogenated homosesquiterpenic fatty acids from Plocamium cartilagineum. , 2001, Phytochemistry.

[150]  J. Beckwith,et al.  BIOLOGICAL CHLORINATION. VIII. LATE INTERMEDIATES IN THE BIOSYNTHESIS OF CALDARIOMYCIN. , 1963, The Journal of biological chemistry.

[151]  S. Matsunaga,et al.  Antifungal Brominated C18 Acetylenic Acids from the Marine Sponge, Petrosia volcano Hoshino , 1993 .

[152]  M. D. Sutherland,et al.  Pigments of marine animals , 1968 .

[153]  R. Andersen,et al.  Geodiamolides C to F, new cytotoxic cyclodepsipeptides from the marine sponge Pseudaxinyssa sp. , 1990 .

[154]  A. Isogai,et al.  Structures of syringostatins A and B, novel phytotoxins produced by pseudomonas syringae pv. syringae isolated from lilac blights , 1990 .

[155]  M. Garson,et al.  New chlorinated peptides from the tropical marine sponge Dysidea sp. , 2001 .

[156]  David J. Williams,et al.  The X-ray structure and absolute configuration of insect antifeedant clerodane diterpenoids from Teucrium africanum , 1982 .

[157]  J. Shima,et al.  The Structure of Enacyloxin II, a Novel Linear Polyenic Antibiotic Produced by Gluconobacter sp. W-315 , 1990 .

[158]  J. Ruuskanen,et al.  Trichloroacetic acid in pine needles in the vicinity of a pulp mill , 1993 .

[159]  John T. Welch,et al.  Fluorine in bioorganic chemistry , 1991 .

[160]  Anne Praud,et al.  Malyngamide G : Proposition de structure pour un nouvel amide chloré d'une algue bleu-verte epiphyte de Cystoseira crinita. , 1993 .

[161]  G. Gribble The diversity of naturally occurring organobromine compounds , 1999 .

[162]  J. Barchi,et al.  Structure of malyngamide C , 1985 .

[163]  W. Gerwick,et al.  Egregiachlorides A-C: New chlorinated oxylipins from the marine brown alga Egregia menziesii , 1993 .

[164]  V. Marzo ‘Endocannabinoids’ and other fatty acid derivatives with cannabimimetic properties: biochemistry and possible physiopathological relevance , 1998 .

[165]  K. Engvild Chlorine-containing natural compounds in higher plants , 1986 .

[166]  T. Řezanka,et al.  Fatty acid composition of Parmelia lichens , 1992 .

[167]  P. Scheuer,et al.  Malyngamides O and P from the sea hare Stylocheilus longicauda. , 2000, Journal of natural products.

[168]  N. Itoh,et al.  A variety of catalases and bromoperoxidases in genus Pseudomonas and their characterization. , 1992, Biochimica et biophysica acta.

[169]  Butler,et al.  Isolation of xestosterol esters of brominated acetylenic fatty acids from the marine sponge xestospongia testudinaria , 1999, Journal of natural products.

[170]  W. Clark,et al.  A novel chlorinated ketide amino acid, herbamide A, from the marine sponge Dysidea herbacea , 1995 .

[171]  Y. Sakagami,et al.  S-4-chlorotryptophan: Its synthesis via resolution, determination of the absolute stereochemistry and identification in the crude seed protein of the pea, pisum sativum , 1988 .

[172]  Jb Willis,et al.  The Alkaloids of Senecio jacobaea L. II. The structures of the acids, and the relationship between Jacobine and Jaconine , 1956 .

[173]  C. Harington Chemistry of Thyroxine: Isolation of Thyroxine from the Thyroid Gland. , 1926, The Biochemical journal.

[174]  F. Schmitz,et al.  (7E, 13ξ, 15Z)-14,16-dibromo-7,13,15-hexadecatrien-5-ynoic acid. A novel dibromo acetylenic acid from the marine sponge Xestospongia muta , 1978 .

[175]  J. Nakayama,et al.  Isolation and structural elucidation of syringostatins, phytotoxins produced by Pseudomonas syringae pv. syringae lilac isolate , 1992 .

[176]  J. Palermo,et al.  Celenamide E, a Tripeptide Alkaloid from the Patagonian Sponge Cliona chilensis , 1998 .

[177]  K. van Pée,et al.  Detection of a bromoperoxidase in Streptomyces phaeochromogenes , 1984, FEBS Letters.

[178]  K. van Pée,et al.  Chloroperoxidase-encoding gene from Pseudomonas pyrrocinia: sequence, expression in heterologous hosts, and purification of the enzyme. , 1993, Gene.

[179]  Y. Sakagami,et al.  l-4-chlorotryptophan from immatum of Pisum sativum and reassignment of the absolute stereochemistry of N-malonyl-4-chlorotryptophan , 1993 .

[180]  H. Yamada,et al.  Haloperoxidase-catalyzed halogenation of nitrogen-containing aromatic heterocycles represented by nucleic bases , 1987 .

[181]  V. Dembitsky,et al.  Diacylglyceryltrimethylhomoserines and phospholipids of some lichen species , 1993 .

[182]  S. Masamune,et al.  The Alkaloids of Senecio jacobaea L. IV. The Structures of Jacobine, Jaconine, Jacoline and their Constituent Acids , 1959 .

[183]  V. Paul,et al.  Kumepaloxane, a rearranged trisnor sesquiterpene from the bubble shell Haminoeacymbalum , 1989 .

[184]  F. S. Brown,et al.  Chloroperoxidase. II. Utilization of halogen anions. , 1966, The Journal of biological chemistry.

[185]  E. Kendall The Isolation in Crystalline Form of the Compound Containing Iodin, Which Occurs in the Thyroid: Its Chemical Nature and Physiologic Activity , 1915 .

[186]  C. Djerassi,et al.  Biosynthetic studies of marine lipids. 5. The biosynthesis of long-chain branched fatty acids in marine sponges , 1986 .

[187]  F. Stermitz,et al.  Pyrrolizidine alkaloids from Cryptantha species , 1993 .

[188]  M. Walsh,et al.  The short chain condensing enzyme has a widespread occurrence in the fatty acid synthetases from higher plants , 1990 .

[189]  R. Andersen,et al.  Cytotoxic peptides from the marine sponge Cymbastela sp. , 1995 .

[190]  T. Haines The chemistry of the sulfolipids , 1971 .

[191]  T. Řezanka,et al.  Lipid composition of some lichens , 1992 .

[192]  G. Barger,et al.  131. Alkaloids of senecio. Part III. Jacobine, jacodine, and jaconine , 1937 .

[193]  T. Geissman The alkaloids of Senecio jacobaea L: The structures of the Alkaloids and the Necic Acids , 1959 .

[194]  L. Vining,et al.  Purification, properties and immunological detection of a bromoperoxidase-catalase from Streptomyces venezuelae and from a chloramphenicol-nonproducing mutant. , 1989, Journal of general microbiology.

[195]  V. Marzo,et al.  High molecular weight polyacetylenes from Petrosia ficiformis: Further structural analysis and biological activity , 1989 .

[196]  R. Wever,et al.  Purification and some characteristics of a non-haem bromoperoxidase from Streptomyces aureofaciens. , 1988, Biochimica et biophysica acta.

[197]  T. Řezanka,et al.  Novel brominated lipidic compounds from lichens of central Asia. , 1999, Phytochemistry.

[198]  Y. Kan,et al.  New malyngamides from the Hawaiian cyanobacterium Lyngbya majuscula. , 2000, Journal of natural products.

[199]  Y. Ohizumi,et al.  Keramadine, a novel antagonist of serotonergic receptors isolated from the okinawan sea sponge Agelas sp.☆ , 1984 .

[200]  S. Marumo,et al.  Identification of 4-Chloroindole-3-acetic Acid and Its Methyl Ester in Immature Seeds of Vicia amurensis (the Tribe Vicieae), and Their Absence from Three Species of Phaseoleae , 1987 .

[201]  V. Dembitsky,et al.  Phospholipid and fatty acid composition of some lichen species , 1991 .

[202]  J. Takemoto,et al.  Structure of phytotoxin syringomycin produced by a sugar cane isolate of pseudomonas syringae pv. syringae , 1990 .

[203]  M. Böttger,et al.  Identification by gc-ms of 4-chloroindolylacetic acid and its methyl ester in immature Vicia faba seeds , 1979 .

[204]  P. Crews,et al.  Melynes, polyacetylene constituents from a vanuatu marine sponge , 1988 .

[205]  S. Matsunaga,et al.  Bioactive marine metabolites XX. Petrosynol and petrosynone, antimicrobial C30 polyacetylenes from the marine sponge Petrosia sp.: Determination of the absolute configuration☆ , 1987 .

[206]  M. Lagarde,et al.  Further studies on the anti-thromboxane A2 activity of monohydroxylated fatty acids. , 1989, Biochemical pharmacology.

[207]  W. Hubbard,et al.  Transformation of arachidonic acid into an iodolactone by the rat thyroid. , 1980, The Journal of biological chemistry.

[208]  H. Fouquet,et al.  Biological Precursors and Genesis of Tyrian‐Purple , 1971 .

[209]  G. Towers,et al.  Chlorination of anthraquinones by lichen and fungal enzymes , 1997 .

[210]  Y. Kashman,et al.  Brominated unsaturated acids from the marine sponge xestospongia sp. , 1987 .

[211]  W. Gerwick,et al.  Grenadadiene and grenadamide, cyclopropyl-containing fatty acid metabolites from the marine cyanobacterium Lyngbya majuscula. , 1998, Journal of natural products.

[212]  K. Ohta,et al.  Antimicrobial compounds of the marine red alga Marginisporum aberrans , 1977 .

[213]  G. Haufe,et al.  A facile two-step synthesis of (ω-1)-fluoroalkan-ω-olides influence of a vicinal fluorine substituent in nucleophilic substitutions , 1996 .

[214]  A. Wright,et al.  Tropical Marine Algae, VII. The Chemical Composition of Marine Algae from North Queensland Waters , 1990 .

[215]  H. Hecht,et al.  Structural investigation of the cofactor-free chloroperoxidases. , 1998, Journal of molecular biology.

[216]  D. Rotella,et al.  Chloroperoxidase mediated halogenation of phenols , 1990, Bulletin of environmental contamination and toxicology.

[217]  M. Bourguet-Kondracki,et al.  Bioactive bromopolyacetylenes from the marine sponge Xestospongia testudinaria , 1992 .

[218]  J. Hamilton,et al.  Identification of threo-ig-fluoro.9,10-Dihydroxystearic acid:a novel cofluorinated fatty acid from dichapetalum toxicarium seeds. , 1990 .

[219]  D. Faulkner,et al.  A chemical defense mechanism for the nudibranch cadlina luteomarginata , 1982 .

[220]  M. Moriguchi,et al.  Antibacterial activity of L-2-amino-4-chloro-4-pentenoic acid isolated from Amanita pseudoporphyria Hongo. , 1987, The Journal of antibiotics.

[221]  A. Numata,et al.  Absolute stereostructures of novel cytotoxic metabolites, gymnastatins A–E, from a Gymnascella species separated from a Halichondria sponge , 1998 .

[222]  H. Egsgaard,et al.  Determination of 4-chloroindole-3-acetic acid methyl ester in Lathyrus, Vicia and Pisum by gas chromatography – mass spectrometry , 1980 .

[223]  P. Manchand,et al.  Stereostructures of geodiamolides A and B, novel cyclodepsipeptides from the marine sponge Geodia sp , 1987 .

[224]  C. Debitus,et al.  Pteridines, sterols, and indole derivatives from the lithistid sponge Corallistes undulatus of the Coral Sea , 1993 .

[225]  M. Pisarev,et al.  Biosynthesis and regulation of iodolipids in calf thyroid. , 1985, Acta endocrinologica.

[226]  D. Mebs Chemical defense of a dorid nudibranch,Glossodoris quadricolor, from the red sea , 1985, Journal of Chemical Ecology.

[227]  A. Argoudelis,et al.  New amino acids from Streptomyces. , 1967, Biochemistry.

[228]  J. Hamilton,et al.  Mass spectrometry of fluorinated fatty acids in the seed oil of Dichapetalum toxicarium , 1998 .

[229]  W. Fenical Molecular Aspects of Halogen-Based Biosynthesis of Marine Natural Products , 1979 .

[230]  T. Řezanka,et al.  Identification of fatty acids from Cladonia lichens , 1991 .

[231]  E. Johansson,et al.  Chlorination and biodegradation of lignin , 2000 .

[232]  C. Wesén,et al.  Identification of chlorinated fatty acids in fish lipids by partitioning studies and by gas chromatography with Hall electrolytic conductivity detection , 1992 .

[233]  P. Mazliak LIPID METABOLISM IN PLANTS , 1973 .

[234]  R. Peters,et al.  Fluorine Compounds in Nature; The Distribution of Carbon-Fluorine Compounds in Some Species of Dichapetalum , 1960, Nature.

[235]  K. Soga,et al.  α-Amino acids from a mushroom, Amanita castanopsidis Hongo, with growth-inhibiting activity , 1999 .

[236]  J. Springer,et al.  Stylocheilamide, an unusual constituent of the sea hare Stylocheilus longicauda , 1978 .

[237]  P. Oelrichs,et al.  Isolation of the Toxic Principle in Acacia georginae , 1961, Nature.

[238]  M. Ishibashi,et al.  Two new tryptophan-derived alkaloids from the Okinawan marine sponge Aplysina sp. , 1994, Journal of natural products.

[239]  M. Masaoud,et al.  A chlorinated amide and piperidine alkaloids from Aloe sabaea. , 2000, Phytochemistry.

[240]  J. M. Gregson,et al.  Puwainaphycin C, a cardioactive cyclic peptide from the blue-green alga Anabaena BQ-16-1. Use of two-dimensional carbon-13-carbon-13 and carbon-13-nitrogen-15 correlation spectroscopy in sequencing the amino acid units , 1989 .

[241]  K. Park Occurrence of Castasterone, Brassinolide and Methyl 4-Chloroindole-3-acetate in Immature Vicia faba Seeds , 1987 .

[242]  J. Hamilton,et al.  High levels of monofluoroacetate in Dichapetalum braunii , 1993 .

[243]  A. Butler Mechanistic considerations of the vanadium haloperoxidases , 1999 .

[244]  G. Soma,et al.  L-2-amino-4-chloro-4-pentenoic acid, a new natural amino acid from Amanita pseudoporphyria hongo , 1974 .

[245]  H. Yamada,et al.  Chloroperoxidase-catalyzed halogenation of trans-cinnamic acid and its derivatives. , 1985, The Journal of biological chemistry.

[246]  I. Odenbrand,et al.  New halogen-specific detector applied to the analysis of chlorinated fatty acids. , 2001, Journal of chromatography. A.

[247]  A. Numata,et al.  GYMNASTERONES, NOVEL CYTOTOXIC METABOLITES PRODUCED BY A FUNGAL STRAIN FROM A SPONGE , 1997 .

[248]  F. S. Brown,et al.  Chloroperoxidase. IV. Evidence for an ionic electrophilic substitution mechanism. , 1967, Journal of the American Chemical Society.

[249]  C. R. Lovell,et al.  Purification and properties of a unique flavin-containing chloroperoxidase from the capitellid polychaete Notomastus lobatus. , 1991, The Journal of biological chemistry.

[250]  D. Hanahan Handbook of lipid research , 1978 .

[251]  T. J. Ahern,et al.  New bromoperoxidase of marine origin. Partial purification and characterization , 1980 .

[252]  Gordon W. Gribble,et al.  Naturally Occurring Organohalogen Compounds , 1998 .

[253]  J. Braekman,et al.  Identification of a major iodolipid from the horse thyroid gland as 2-iodohexadecanal. , 1990, The Journal of biological chemistry.

[254]  A. Adaudi,et al.  Acute toxicity of the leaves and extracts of Dichapetalum barteri (Engl.) in mice, rabbits and goats. , 1977, Toxicology.

[255]  W. Steglich,et al.  Antibiotika aus Basidiomyceten, III. Strobilurin A und B, antifungische Stoffwechselprodukte aus Strobilurus tenacellus , 1978 .

[256]  Sakamoto,et al.  Malyngamides M and N from the Hawaiian Red Alga Gracilaria coronopifolia , 1998, Journal of natural products.

[257]  H. Egsgaard,et al.  Determination of 4-chloroindoleacetic acid methyl ester in Vicieae species by gas chromatography-mass spectrometry , 1981 .

[258]  A. Grimvall,et al.  Naturally-produced organohalogens , 1995 .

[259]  W. Gerwick,et al.  Two new malyngamides from a Madagascan Lyngbya majuscula. , 2000, Journal of natural products.

[260]  R. Wever,et al.  The bromoperoxidase from the lichen Xanthoria parietina is a novel vanadium enzyme. , 1987, The Biochemical journal.

[261]  K. Honn,et al.  Bidirectional control of membrane expression and/or activation of the tumor cell IRGpIIb/IIIa receptor and tumor cell adhesion by lipoxygenase products of arachidonic acid and linoleic acid. , 1989, Cancer research.

[262]  Joseph R. Pawlik Marine invertebrate chemical defenses , 1993 .

[263]  D. Gibson,et al.  Isolation and structure of a brain constituent that binds to the cannabinoid receptor. , 1992, Science.

[264]  W. Gerwick,et al.  Hermitamides A and B, toxic malyngamide-type natural products from the marine cyanobacterium Lyngbya majuscula. , 2000, Journal of natural products.

[265]  J. Hamilton,et al.  Fluoro fatty acids in seed oil of Dichapetalum toxicarium , 1997 .

[266]  T. Haines,et al.  Microbial sulpholipids: (R)-13-choro-1-(R)-14-docosanediol disulphate and polychlorosulpholipids in Ochromonas danica. , 1969, The Biochemical journal.

[267]  C. Ireland,et al.  Iodinated phenethylamine products from a didemnid tunicate , 1984 .

[268]  D. O'Hagan,et al.  Fluorine-containing natural products , 1999 .

[269]  P. Crews,et al.  Mauritamide A and accompanying oroidin alkaloids from the sponge agelas mauritiana , 1994 .

[270]  Y. Sasaki,et al.  [Lipid metabolism in plants: fatty acid synthesis]. , 2003, Tanpakushitsu kakusan koso. Protein, nucleic acid, enzyme.

[271]  C. Eggert,et al.  Degradation of chlorinated lignin compounds in a bleach plant effluent by the white-rot fungus Trametes versicolor , 1991, Applied Microbiology and Biotechnology.