Natural nitriles and their metabolism
Tóm tắt
The present work reviews the numerous nitrile compounds that have been isolated from plants and animals. Two kinds of potentially toxic molecules are widespread, namely the cyanogenic glycosides and cyanollpids. Many other aromatic and allphatic nitriles are synthesized to a lesser extent. Different studies on the synthesis and degradation of these cyanogenic compounds are also reviewed to emphasize the potential use of different microorganisms for the detoxification of food and foodstuff.
Tài liệu tham khảo
Abrol, Y.P., Conn, E.E. &Strocker, J.I.R. 1966 Studies on the identification, biosynthesis and metabolism of cyanogenic glucosides inNandina domestica Thumb.Phytochemistry 5, 1021–1027.
Ahmad, R., Ahmad, I. &Osman, S.M. 1985 A cyanogenetic lipid fromKoelrenteria apiculata seed oil.Chemistry and Industry 21, 734.
Allen, J. &Strobel, G.A. 1966 The assimilation of H14CN by a variety of fungi.Canadian Journal of Microbiology 12, 414.
Aritomi, M., Kumori, T. &Kawasaki, T. 1985 Cyanogenic glycosides in leaves ofPerrilla frutescens var.acuta.Phytochemistry 24, 2438–2439.
Arnaud, A. 1984 Remarques sur le métabolisme des nitriles et des amides chez une souche deBrevibacterium sp. Thèse de Doctorat d'Etat. Université des Sciences et Techniques du Languedoc, Montpellier, France.
Arnaud, A., Galzy, P. &Jallageas, J.L. 1976 Etude de l'activité nitrilasique de quelques bactéries.Revue des Fermentations et des Industries Alimentaires 31, 39–44.
Asano, Y., Yasuda, T., Tani, Y. &Yamada, H. 1982 A new enzymatic method of acrylamide production.Agricultural and Biological Chemistry 46, 1183–1189.
Bui, K., Fradet, H., Arnaud, A. &Galzy, P. 1984 A nitrile hydratase with a wide substrate spectrum produced by aBrevibacterium sp.Journal of General Microbiology 130, 89–93.
Bunch, A.W. &Knowles, C.J. 1980 Cyanide production and degradation during growth of the snow mold fungus.Journal of General Microbiology 116 9–16.
Butler, G.W. &Butler, B.G. 1960 Biosynthesis of linamarin and lotaustralin in white clover.Nature 187, 780–781.
Butterfield, C.S., Conn, E.E. &Seigler, D.S. 1975 Elucidation of structure and biosynthesis of acacipetalin.Phytochemistry 14, 993–997.
Capron, R.J. &MacLeod, J.K. 1987 Two epimeric dibromonitriles from the Australian spongeAplysina laevis.Australian Journal of Chemistry 40, 341–346.
Castric, P.A. 1977 Glycine metabolism byPseudomonas aeruginosa hydrogen cyanide biosynthesis.Journal of Bacteriology 130, 826–831.
Castric, P.A. &Strobel, G.A. 1969 Cyanide metabolism byBacillus megaterium.Journal of Biological Chemistry 244, 4089–4094.
Chamberlain, K. &Wain, R.L. 1973 Studies on plant growth relating substance—XXXVI. The metabolism of indole 3 acetonitrile and related compounds in wheat and pea tissues.Annals of Applied Biology 75, 409–417.
Ballester, A., Verwey, A. &Overeem, J.C. 1975 2-Hydroxyphenyl acetic acid and 2,4-dihydroxyphenyl acetonitrile fromErica scoparia.Phytochemistry 14, 1667–1668.
Bandyopadhyay, A.K., Nagasawa, T., Asano, Y., Fujishiro, H., Tani, Y. &Yamada, H. 1986 Purification and characterization of benzonitrilases fromArthrobacter sp. strain J-1.Applied and Environmental Microbiology 51, 302–306.
Bell, E.A. 1971 Comparative biochemistry of non-protein amino-acid. InChemotaxonomy of the Leguminosae eds. Harbone, J.B., Boutler, D. & Turner B.L., pp. 179–206. London: Academic Press.
Bennet-Clark, T.A. &Kefford, N.P. 1953 Chromatogrphy of the growth substances in plant extracts.Nature 171, 645–647.
Bove, C. &Conn, E.E. 1961 Metabolism of aromatic compounds in higher plants—II. Purification and properties of the oxynitrilase ofSorghum vulgare.Journal of Biological Chemistry 236, 207–210.
Brysk, M.M., Corpe, W.A. &Hankes, L.V. 1969 β-Cyanoalanine formation byChromomacterium violaceum.Journal of Bacteriology 97, 322–327.
Brysk, M.M. &Ressler, C. 1970 γ-Cyano-α-l-aminobutyric acid. A new product of cyanide fixation inChromobacterium violaceum.Journal of Biological Chemistry 245, 1156–1160.
Clapp, R.C., Bisset, F.M., Coburn, R.A. &Long, L. 1966 Cyanogenesis in manioc, linamarin and isolinamarin.Phytochemistry 5, 1323–1326.
Coburn, R.A. &Long, L. Jr. 1966 Gynocardin.Journal of Organic Chemistry 31, 4312–4315.
Colotello, N. &Ward, E.W. 1961 β-Glycosidase activity and cyanogenesis in the susceptibility of alfalfa to winter crown rot.Nature 184, 242–243.
Commeyras, A., Arnaus, A., Galzy, P. & Jallageas, J.C. 1973 Procédé de préparation d'acides organiques par hydrolyse biologique.Brevet Fr. no. 73-33613.
Commeyras, A., Arnaus, A., Galzy, P. & Jallageas, J.C. 1973 Procédé de préparation d'acides organiques par hydrolyse biologique.Brevet, Fr. no. 73-41828.
Conn, E.E. 1973 Biosynthesis of cyanogenic glycosides. InNitrogen Metabolism in Plants, eds, Goodwin, T.W. & Smellie, R.M.S. Biochemical Society Symposium, Vol. 38, pp. 277–302. London: The Biochemical Society.
Conn, E.E. 1979a Cyanogenic glycosides. InInternational Review of Biochemistry of Nutrition I.A., eds Neuberger, A., Jukes, T.H., Vol. 27, pp. 21–43. Baltimore: University Park Press.
Conn, E.E. 1979b Biosynthesis of cyanogenic glycosides.Naturwissenschaften 66, 28–34.
Conn, E.E. &Akazawa, T. 1958 Biosynthesis ofp-hydroxybenzaldehyde.Federation Proceedings: Federation of American Societies for Experimental Biology 17, 205.
Davis, R.H. &Nahrstedt, A. 1985 Cyanogenesis in insects. InComprehensive Insect Physiology, Biochemistry and Pharmacology. Vol. 11, eds, Kerkut, G.A. & Gilbert, L.I., pp 635–654. Oxford: Pergamon Press.
Dierickx, P., Wauters, E. &Vendrig, J. 1975 On the requirement of hydroxynitrile lyase in the conversion of orthonil to chloro-tolylacetic acid.Zeitschrift für Pflanzen-physiologie 75, 191–200.
Digeronimo, M.J. &Antoine, A.D. 1976 Metabolism of acetonitrile and propionitrile byNocardia rhodocrous LL 100-21.Applied and Environmental Microbiology 31, 900–906.
Duffey, S.S. 1981 Cyanide and arthropods. InCyanide in Biology, eds Venesland, B., Conn, E.E., Knowles, C.J., Westley, J. & Wissing, F., pp. 385–414. London: Academic Press.
Dunnill, P.M. &Fowden, L. 1965 Enzymic formation of β-cyanoalanine from cyanide byEscherichia coli extracts.Nature 208, 1206–1207.
Emerson, H.W., Cady, H.P. &Bailey, E.H.S. 1913, On the formation of hydrocyanic acid from proteins.Journal of Biological Chemistry 15, 415–417.
Erb, N., Zinstheister, H.D. Lehmann, G. &Nahrstedt, A. 1979 A new cyanogenic glycoside fromHordeum vulgare.Phytochemistry 18, 1515–1517.
Ettlinger, M.G., Jaroszewski, J.W., Jensen, S.R., Nielsen, B.J. & Nartey, F. 1977 Proacacipetalin and acacipetalin.Journal of the Chemical Society. Chemical Communications, 952–953.
Eyjolfson, R. 1970 Isolation and structure determination of triglochinin a new cyanogenic glucoside fromTriglobin maritimum.Phytochemistry 9, 845–851.
Eyjolfson, R. 1971 Constitution and stereochemistry of lucumin a cyanogenic glucoside fromLucuma mammosa.Acta Chemica Scandinavica 25, 1898–1900.
Fawcett, C.H. Seeley, R.C., Taylor, H.F., Wain, R.L. &Wightman, F. 1955 Alpha-oxydation of omega-(2∶4-dichlorophenoxy) alkanenitriles and 3-indolylacetonitrile within plant tissues.Nature 176, 1026–1028.
Fawcett, C.H., Taylor, H.F., Wain, R.L. &Wightman, F. 1958 The metabolism of certain acids, amides and nitriles within plant tissues.Proceedings of the Royal Society, London 148B, 543–570.
Firmin, J.L. &Gray, D.O. 1976 The biochemical pathway for the breakdown of methyl cyanide (acetonitrile) in bacteria.Biochemical Journal 158, 223–229.
Fry, W.E. &Millar, D. 1972 Cyanide degradation by an enzyme fromStemphylium loti.Archives of Biochemistry and Biophysics 151, 468–474.
Fry, W.E. &Munch, D.C. 1975 Hydrogen cyanide detoxification byGloeocercospora sorghi.Physiological Plant Pathology 7, 23–33.
Fry, W.E. &Myers, D.F. 1981 Hydrogen cyanide metabolism by fungal pathogens of cyanogenic plants. InCyanide in Biology, eds Venesland, B., Conn, E.E., Knowles, C.J., Westley, J. & Wissing, F. pp. 321–334. London: Academic Press.
Fukuda, Y., Fukui, M., Harada, T. &Izumi, Y. 1971 Formation of amino acid from aminonitrile by cell suspensions of a strain ofCorynebacterium.Journal of Fermentation Technology 49, 1011–1016.
Fulmor, W., van Lear, G.E., Morton, G.O. &Mills, R.D. 1970 Isolation and absolute configuration of the aerophlysinin I enantiomorphic pair fromLanthella ardis.Tetrahedron Letters 52, 4551–4552.
Gander, J.E. 1962 Incorporation of14C intop-hydroxymandelonitrile β-glucoside and other phenolic substances inSorghum seedlings.Journal of Biological Chemistry 237, 3329–3332.
Gewitz, H.S., Piefke, J., Langowska, K. &Venesland B. 1980 The formation of hydrogen cyanide from histidine in the presence of amino acid oxidase and peroxidase.Biochimica et Biophysica Acta 611, 11–26.
Gewitz, H.S., Pistorius, E.K., Voss, H. &Venesland B. 1976, Cyanide formation in preparations fromChlorella and New Zealand spinach leaves: effect of added aminoacids.Planta 131, 149–153.
Giza, Y.H., Ratzkin, H. &Ressler, C. 1963 Biosynthesis of asparagine from β-cyano-l-alamine inNeurospora crassa, and species ofLathyrus andVicia.Federation Proceedings: Federation of American Societies for Experimental Biology 22, 651.
Gmelin, R., Schuler, M. &Bordas, E. 1973 Holocalin ein neues cyanogenes glykosid ausHolocalyx balansae.Phytochemistry 12, 457–461.
Grant, D.J.W. 1973 Degradative versatility ofCorynebacterium pseudodiphteriticum N.C.I.B. 10803 which uses amides as carbon source.Antonie van Leeuwenhoek 39, 273–279.
Hardy, R.W.F., Burns, R.C. &Parshall, G.W. 1971 Bio-inorganic chemistry of dinitrogen fixation. InInorganic Biochemistry, ed. Eichkorn Vol. 2, pp. 746–793 Amsterdam: Elsevier.
Harper, D.B. 1976 Purification and properties of an unusual nitrilase fromNorcadia N.C.I.B. 11216.Biochemical Society Transactions 4, 502–504.
Harper, D.B. 1977a Microbial metabolism of aromatic nitriles.Biochemical Journal 165, 309–319.
Harper, D.B. 1977b Fungal degradation of aromatic nitriles.Biochemical Journal 167, 685–692.
Harris, R.E., Bunch, A.W. &Knowles, C.J. 1987 Microbial cyanide and nitrile metabolism.Science Progress (Oxford) 71, 293–304.
Harris, R.E. &Knowles, C.J. 1983 The conversion of cyanide to ammonia by extracts of a strain ofPseudomonas fluorescens that utilizes cyanide as a source of nitrogen for growth.FEMS Microbiology Letters 20, 337–341.
Hegnauer, R. 1973 Die cyanogenen Verbindungen der Liliatae und Magnoliatae-Magnoliidae: zur systematischen bedeutung des Merkmals der Cyanogenese.Biochemical Systematics 1, 191–197.
Hegnauer, R. 1977 Cyanogenic compounds as systematic markers inTracheophyta.Plant Systematics Evolution Suppl.1, 191–209.
Henbest, H.B., Jones, E.R.H., Smith, G.F. 1953 Isolation of a new plant growth hormone, 3-indoylacetonitrile.Journal of the Chemical Society 75, 3796–3801.
Hofmann, A.W. 1874 Uber das aetherische Oel vonTropäolum majus.Berichte 7, 518–519.
Hook, R.H. &Robinson, W.G. 1964 Ricinine nitrilase—II. Purification and properties.Journal of Biological Chemistry 239, 4263–4267.
Hubel, W. &Nahrstedt, A. 1979 Cardiospermin sulfate. A sulfur-containing cyanogenic glycoside fromCardiospermum grandiflorum.Tetrahedron Letters 45, 4395–4396.
Hubel, W., Nahrstedt, A., Fikenscher, L.H. &Hegbauer, R. 1982 Zierinxyloside a new cyanogenic glycoside fromXeranthemum cylindraceum.Planta Medica 44, 4395–4396.
Hubel, W., Nahrstedt, A., Fikenscher, L.H. &Hegbauer, R. 1982 Zierinxyloside a new cyanogenic glycoside fromXeranthemum cylindraceum.Planta Medica 44, 178–180.
Jackson, R.C. &Handschumacher, R.E. 1970Escherichia coli L-asparaginase. Catalytic activity and subunit nature.Biochemistry 9, 3585–3590.
Jallegeas, J.C., Arnaud, A. &Galzy, P. 1980 Bioconversions of nitriles and their applications.Advances in Biochemical Engineering 14, 1–31.
Jaroszewski, J.W., Anderson, J.J. &Billeskov, I. 1987 Natural cyclopentenoid cyanohydrin glycosides—4. Plants as a source of Chiral.Tetrahedron 43, 2349–2354.
Jaroszewski, J.W. &Olafsdottir E.S. 1987 Monohydroxylated cyclopentenone cyanohydrin glucosides of Flacourtiaceae.Phytochemistry 26, 3348–3349.
Jones, D.A. 1979 Chemical defense: primary or secondary functions?The American Naturalist 113, 445–451.
Jones, E.R.H., Henbest, H.B., Smith, G.F. &Bentley, J.A. 1952 3-Indolylacetonitrile: a naturally occurring plant growth hormone.Nature 169, 485–487.
Kikuchi, K. 1955 Antibiotics fromStreptomyces sp. no. E-212. Studies on Streptomyces antibiotics—XXIV.Journal of Antibiotics (Tokyo) Series A 8, 145–147.
Knowles, C.J. &Bunch, A.W. 1986 Microbial cyanide metabolism.Advances in Microbial Physiology 27, 73–111.
Kofod, H. &Eyjolfson, R. 1966 The isolation of the cyanogenic glucoside prunasin fromPteridium aquilinum (L.) Kuhn.Tetrahedron Letters 12, 1289–1290.
Kofod, H. &Eyjolfson, R. 1969 Cyanogenesis in species of the fern generaCystopteris andDavallia.Phytochemistry 8, 1509–1511.
Koj, A., Michalik, M. &Krasperczyk, H. 1977 Mitochondrial and cytosolic activities of three sulfur transferase in some rat tissues and Morris hepatomas.Bulletin de l' Académie Polonaise des Sciences, Série des Sciences Biologiques 25, 1–6.
Kojima, M., Poulton, J.E., Thayer, S.S. &Conn, E.E. 1979 Tissue distribution of dhurrin and of enzymes involved in its metabolism in leaves ofSorghom bicolor.Plant Physiology 63, 1022–1028.
Kutacek, V. &Kefeli, V.I. 1968 The present knowledge of indole compounds in plants of the Brassicaceae family. InBiochemistry and Physiology of Plant Growth Substances, eds Wigtman, F. & Setterfield, G., pp. 127–152. Ottawa: The Ring Press.
Lang, K. 1933 Die Rhodanbildung in Tierkörpier.Biochemische Zeitschrift 259, 243–256.
Lebeau, J.B., Cormack, M.W. &Mofatt, J.E. 1959 Measuring pathogenesis by the amount of toxic substances produced in alfalfa by a snow mold fungus.Phytopathology 49, 303–305.
Li, J., Burgess, B.K. &Corbin, J.L. 1982 Nitrogenase reactivity: cyanide as a substrate and inhibitor.Biochemistry 21, 4393–4402.
Mahadevan, S. &Thimann, K.V. 1964 Nitrilase—II. Substrate specificity and possible mode of action.Archives of Biochemistry and Biophysics 107, 62–68.
Mao, C.H., Blocher, J.P., Anderson, L. &Smith, A.C. 1965, Cyanogenesis inSorghom vulgare—I. An improved method for the isolation of dhurrin; physical properties of dhurrin.Phytochemistry 4, 297–303.
Marion, L. 1950 The ricinus alkaloid-Ricinine. InThe Alcaloids: Chemistry and Physiology, Vol. 1, pp. 206–209. New York: Academic Press.
Maslin, B.R., Conn, E.E. &Dunn, J.E. 1985 Cyanogenesis inAcacia pachyphloia.Phytochemistry 24, 961–963.
Matthews, C.D., Nagasawa, T., Kobayashi, M. &Yamada, H. 1988 Nitrilase catalysed production of nicotinic acid from 3-cyanopyridine inRhodococcus rhodocrous J1.Applied and Environmental Microbiology 54, 1030–1032.
Mentzer, C. &Favre-Bonvin, J. 1962 Sur la biogénèse du glucoside cyanogénétique des feuilles de laurier-cerise(Prunus lauro-cerasus).Comptes Rendus de l'Académie des Sciences 253, 1072–1074.
Michaels, R. &Corpe, W.A. 1965 Cyanide formation byChromobacterium violaceum.Journal of Bacteriology 89, 106–112.
Michaels, R., Hankes, L.V. &Corpe, W.A. 1965 Cyanide formation from glycine by non-proliferating cells ofChromobacterium violaceum.Archives of Biochemistry and Biophysics 111, 121–125.
Mikolajczak, K.L. 1977 Cyanolipids.Progress in the Chemistry of Fats and Other Lipids 15, 97–130.
Miller, J.M. &Gray, D.O. 1982 The utilization of nitriles and amides by aRbodococcus species.Journal of General Microbiology 128, 1803–1809.
Mimura, A., Kawano, T. &Yamada, K. 1969 Applications of microorganisms to petrochemical industry—I. Assimilation of nitrile compounds by organisms.Journal of Fermentation Technology 47, 631–638.
Mukherjee, R. & Chatterjee, A. 1964 Structure of nudiflorine, a naturally occurring isomer of ricinidine.Chemistry and Industry, 1524–1525.
Mukherjee, R. &Chatterjee, A. 1966 Structure and synthesis of nudiflorine, a new pyridone alkaloid.Tetrabedron 22, 1461–1466.
Mustafa, J., Gupta, A., Agarwal, R. &Osman, S.M. 1986, Cupiana anacardioides: a rich source of cyanolipids.Journal of the American Oil Chemistry Society 63, 671–672.
Nagasawa, T., Kobayashi, M. &Yamada, H. 1988 Optimum culture conditions for the production of benzonitrilase byRhodococcus rbodocrous J1.Archives of Microbiology 150, 89–94.
Nahrstedt, A. 1976 A new cyanogenic glycoside fromSorbaria arborea (Rosaceae).Zeitschrift für Naturforschung 31, 397–400.
Nahrstedt, A. 1985 Cyanogenic compounds as protecting agents for organisms.Plant Systematics and Evolution 150, 35–47.
Nahrstedt, A. &Davis, R.H. 1983 Occurrence, variation and biosynthesis of the cyanogenic glucosides linamarin and lotaustralin in species of theHeliconiini (Insecta: Lepidoptera).Comparative Biochemistry and Physiology 75B, 65–73.
Nahrstedt, A., Hubel, W., Wray, N., Fickenscher, L.H. &Hegnauer, R. 1982b Neue cyanglykoside aus Compositen.Planta Medica 45, 142.
Nahrstedt, A., Kant, J.D. &Wray, V. 1982c Acallyphin, a new cyanogenic glucoside fromAcalypha indica.Phytochemistry 21, 101–105.
Nahrstedt, A., Walther, A. &Wray, V. 1982a Sarmentosin epoxyde: a new cyanogenic compound fromSedum cepaea.Phytochemistry 21, 107–110.
Nartey, F. 1981 Cyanogenesis in tropical feeds and foodstuffs. InCyanide in Biology, eds Venesland, B., Conn, E.E., Knowles, C.J., Westley, J. & Wissing, F., pp. 115–132. London: Academic Press.
Nishizawa, M., Adachi, K., Sastrapradja, S. &Hayashi, Y. 1983 Isolation of individual type II cyanolipids fromNephelium lappacium.Phytochemistry 22, 2853–2855.
Nitsch, J.P., Nitsch, C. &Wetmore, R.H. 1955 Native growth substances in various plant tissues as separated by paper chromatography.Proceedings of the Plant Physiology Meetings 30, 55.
Nitto Chemical Industry Co. Ltd. 1979 Procédé de préparation de l'acrylamide et du méthacrylamide à l'aide de microorganismes. French Patent, no. 79 079 35.
Pallares, E.S. 1946 Note on the poison produced byPolydesmus (Fontaria) vicinus.Archives of Biochemistry and Biophysics 9, 105–108.
Pistorius, E.K. &Voss, H. 1977 AD-amino acid oxidase fromChorella vulgaris.Biochemica et Biophysica Acta 481, 395–406.
Ressler, C., Abe, O., Kondo, Y., Cottrell, B. &Abe, K. 1973 Purification and characterization fromChromobacterium violaceum of an enzyme catalyzing the synthesis of γ-cyano α-aminobutyric acid and thiocyanate.Biochemistry 12, 5369–5377.
Robinson, W.C. &Hook, R.H. 1974 Ricinine nitrilase—I. Reaction product and substrate specificity.Journal of Biological Chemistry 239, 4257–4262.
Robiquet, F. &Boutron-charlard, A.F. 1830 Nouvelles expériences sur les amandes amères et sur l'huile volatile qu'elles fournissent.Annales de Chimie et Physique 44, 352–382.
Rollinson, G., Meadows, M.P., Harris, R.E. &Knowles, C.J. 1987 The growth of a cyanide utilising strain ofPseudomonas fluorescens in a liquid culture on nickel cyanide as a source of nitrogen.FEMS Microbiology Letters 40, 199–205.
Russel, G.B. &Reay, R.F. 1971 The structures of tetraphyllin A and B two new cyanoglucosides. FromTetrapathazea tetranda.Phytochemistry 10, 1373–1377.
Sakai, T., Yanase, H., Sawada, M. &Tonomura, K. 1981 Formation of β-cyanoalanine by a cyanide-resistant strain:Enterobacter sp. 101.Agricultural and Biological Chemistry 45, 2053–2062.
Saunders, J.A., Conn, E.E., Holin, C. &Stocking, C.R. 1977 Subcellular localization of the cyanogenic glycoside ofSorghom by autoradiography.Plant Physiology 59, 647–652.
Saupe, S.G. 1981 Cyanogenic compounds and angiosperm phylogeny. InPhytochemistry and Angiosperm Phylogeny, eds. Young, D.A. & Seigler, D.S. pp. 80–116. New York: Praeger.
Schilling, E.D. &Strong, F.M. 1954 Isolation structure and synthesis ofLathyrus factor fromL. odoratus.Journal of the American Chemical Society 76, 2848.
Schilling, E.D. &Strong, F.M. 1955 Isolation, structure and synthesis ofLathyrus factor fromL. odoratus.Journal of the American Chemical Society 77, 2843–2445.
Secor, J.B., Conn, E.E., Dunn, J.E. &Seigler, D.S. 1976 Detection and identification of cyanogenic glucosides in six species ofAcacia.Phytochemistry 15, 1703–1706.
Selly, M.K. &Conn, E.E. 1971 Hydroxynitriles lyase (Sorghum vulgare). InMethods in Enzymology, Vol. XVII, Part B, ed. Tabor, N.I.H., pp. 239–244. New York: Academic Press.
Seigler, D.S. 1975 Isolation and characterization of naturally occurring cyanogenic compounds.Phytochemistry 14, 9–29.
Seigler, D.S. 1981 Cyanogenic glycosides and lipids: structural types and distribution. InCyanide in Biology, eds Venesland, B., Conn, E.E., Knowles, C.J., Westley, J. & Wissing, F., pp. 133–143. London: Academic Press.
Selgler, D.S., Butterfield, C.S., Dunn, J.E. &Conn, E.E. 1975 Dihydroacacipetalin—a new cyanogenic glucoside fromAcacia sieberiana var.woodii.Phytochemistry 14, 1419–1420.
Seigler, D.S., Dunn, J.E., Conn, E.E. &Pereira, J.F. 1983 Cyanogenic glycosides from four Latin American species ofAcacia.Biochemical Systematics and Ecology 11, 15–16.
Seigler, D.S., Eggerding, C. &Butterfield, C. 1974 A new cyanogenic glucoside fromCardiospermum hirsutum.Physochemistry 13, 2330–2332.
Seigler, D.S., Spencer, K.C., Statler, W.S., Conn, E.E. &Dunn, J.E. 1982 Tetraphyllin B and epitetraphyllin B sulphates: novel cyanogenic glucosides fromPassiflora caerulea andP. Alatocaerulea.Phytochemistry 21, 2277–2285.
Smith, A.E. &Cullimore, D.R. 1974 Thein vitro degradation of the herbicide bromoxynil.Canadian Journal of Microbiology 20, 773–776.
Smith, C.R. Jr, Weisleder, D., Miller, R.W., Palmer, I.S. &Olson, O.O.E. 1980 Linustatin and neolinustatin cyanogenic glycosides of linseed meal that protect animal against selenium toxicity.Journal of Organic Chemistry 45, 507–510.
Solomonson, L.P. 1978 Algal reduction of nitrate. InMicrobiology-1978, ed. Schlessinger, D., pp. 315–319. Washington: American Society for Microbiology.
Spencer, K.C. 1984 Cyclopentenoid cyanogens: their chemistry, in plant systematics, and their role in the coevolution of plants and insects Ph.D. Thesis, Univrsity of Illinois, Urbana.
Spencer, K.C. &Seigler, D.S. 1983 Cyanogenesis ofPassiflora edulis.Journal of Agricultural and Food Chemistry 31, 794–796.
Stam, H., Stouthamer, A.H. &Van Verseveld, H.W. 1985 Cyanide assimilation in Rhizobium ORS 571: Influence of the nitrogenase catalyzed hydrogen production on the efficiency of growth.Archives of Microbiology 143, 196–202.
Stevens, D.L. &Strobel, G.A. 1968 Origin of cyanide in cultures of a psychrophilic basidiomycete.Journal of Bacteriology 95, 1094–1102.
Strobel, G.A. 1964 Hydrocyanic acid assimilation by a psychrophilic basidiomycete.Canadian Journal of Biochemistry 42, 1637–1639.
Strobel, G.A. 1966 The fixation of hydrocyanic acid by a psychrophilic basidiomycete.Journal of Biological Chemistry 241, 2618–1621.
Strobel, G.A. 1967 4-Amino-4-cyanobutyric acid as an intermediate in glutamate biosynthesis.Journal of Biological Chemistry 242, 3265–3269.
Sykes, A.H. 1981 Early studies on the toxicology of cyanide. InCyanide in Biology, eds Venesland, B., Conn, E.E., Knowles, C.J., Westley, J. & Wissing, F. pp. 1–10. London: Academic Press.
Tapper, B.A. &MacDonald, M.A. 1974 Cyanogenic compounds in culture of a psychrophylic basidiomycete (snow mold).Canadian Journal of Microbiology 20, 563–566.
Taylor, H.F. &Wain, R.L. 1959 α-Oxidation of indole acetonitrile.Nature 184, 1142.
Thimann, K.V. &Mahadevan, S. 1958 Enzymatic hydrolysis of indoleacetonitrile.Nature 181, 1466–1467.
Thimann, K.V. &Mahadevan, S. 1963 Nitrilase—I. Occurence, preparation and general properties of the enzyme.Archives of Biochemistry and Biophysics 105, 133–141.
Towers, G.H.N., MacInnes, A.G. &Neish, A.C. 1964 The absolute configurations of the phenolic cyanogenetic glucosides taxiphyllin and dhurrin.Tetrahedron 20, 71–77.
Tschiersch, B. 1966 Toxische Aminosäuren.Pharmazie 21, 445–457.
Uematsu, T. &Suhadolnik, 1974In vivo and enzymatic conversion of Toyoramycin to sangivamycin byStreptomyces rimosus.Archives of Biochemistry and Biophysic 162, 614–626.
van der Wal, B., Sipma, G., Kettenes, O.K. &Semper, A.T.H.J. 1968 Some new constituents of roasted cocoa.Recuil des Travaux Chimiques des Pays-Bas 87, 238–240.
van Rompuy, L., Lambein, F., De Gussen, R. &Van Parijs, R. 1974, The isolation and structure analysis of 2-(2-cyanoethyl)-3-isoxazolin-5-one, 2-(β-D-glucopyranosyl)-3-isoxazolin-5-one and 2-carboxymethyl-3-isoxazolin-5-one fromLathyrus odoratus.Biochemical and Biophysical Research Communications 56, 199–205.
Venesland, B., Pistorius, E.K. &Gewitz, H.S. 1981 HCN production by microalgae. InCyanide in Biology, eds Venesland, B., Conn, E.E., Knowles, C.J., Westley, J. & Wissing, F., pp. 349–361. London: Academic Press.
von Denffer, D., Behrens, M. &Fischer, A. 1952 Papierchromatographischer und papierelektrophoretischer Nachweis des β-Indolacetonitrils und des β-Indolaldehyds in Extrakten aus Kohlpflanzen.Naturwissenschaften 39, 550–551.
Ward, E.W.B. &Thorn, G.D. 1965 Evidence for the formation of HCN from glycine by a snow mold fungus.Canadian Journal of Botany 4, 95–104.
Ward, E.W.B., Thorn, G.D. &Staratt, A.N. 1971 Amino acid source of a hydrogen cyanide in cultures of psychrophilic basidiomycete.Canadian Journal of Microbiology 17, 1061–1066.
Watanabe, I., Satoh, Y. &Enomoto, K. 1987 Sereening, isolation and taxonomical properties of microorganisms having acrylonitrile-hydrating activity.Agricultural and Biological Chemistry 51, 3193–3199.
Weigiang, S., Dengxi, W. &Guanglin, Y. 1988 Metabolism of propionitrile byPseudomonas putida Jp1 and induced formation of nitrile hydratase. InAbstract book of the 8th International Biotechnology Symposium. Paris, ed Société Française de Microbiologie (SFP), p. 316. Paris: SFP.
Wells, W.W., Yang, M.G., Bolzer, W. &Mickelsen, O. 1968, Gas-liquidchromatographic analysis of cycaxin in cycad flour.Analytical Biochemistry 25, 325–329.
Westley, J. 1981 Cyanide and sulfane sulfur. In:Cyanide in Biology, eds. Venesland, B., Conn, E.E., Knowles, C.J., Westley, J. & Wissing, F., pp. 61–76. London: Academic Press.
Wissing, F. 1974 Cyanide formation from oxidation of glycine by aPseudomonas species.Journal of Bacteriology 117, 1289–1294.
Wray, V., Davis, R.H. &Nahrstedt, A. 1983 Biosynthesis of cyanogenic glycosides in butterflies and moths: incorporation of valine and isoleucine into linamarin and lotaustralin byZygaena andHeliconius species.Zeitschrift für Naturforschung 38C, 583–588.
Wu, J., Fairchild, E.D., Beal, J.L., Tomimatsu, T. &Dokoth, R.W. 1979 Lithospermoside and dasycarponin: cyanoglucosides fromThalictrum.Journal of Natural Products 42, 500–511.
Yamada, H., Asano, Y., Hino, T. &Tani, Y. 1979 Microbial utilization of acrylonitrile.Journal of Fermentation Technology 57, 8–14.
Yamada, H., Asano, Y. &Tani, Y. 1980 Microbial utilization of glutaronitrile.Journal of Fermentation Technology 58, 495–500.
Yanase, H., Sakai, T. &Tonomura, K. 1982a Purification and crystallization of a β-cyanoalanine forming enzyme fromEnterobacter sp. 10-1.Agricultural and Biological Chemistry 46, 355–361.
Yanase, H., Sakai, T. &Tonomura, K. 1982b Some properties of a β-cyanoalanine forming enzyme ofEnterobacter sp. 10-1.Agricultural and Biological Chemistry 46, 363–369.
Yanase, H., Sakai, T. &Tonomura, K. 1983 Purification, crystallization and properties of β-cyanoalanine degrading enzyme inPseudomonas sp. 13.Agricultural and Biological Chemistry 47, 473–482.