Advertisement

The Polyene Antifungal Antibiotics

  • W. Oroshnik
  • A. D. Mebane
Chapter
Part of the Fortschritte Der Chemie Organischer Naturstoffe book series (FORTCHEMIE (closed), volume 21)

Zusammenfassung

During the early 1950’s there appeared reports, from time to time of the presence among the products elaborated by actinomycetes of antifungal antibiotics which exhibited very similar and very characteristic multipeaked ultraviolet absorption spectra. In 1954, with a good number of examples on record, these spectra were analyzed and identified as those of straight-chain conjugated polyenes, comprising tetraenes, pentaenes, hexaenes and heptaenes (85, 130). These antibiotics have since been commonly referred to as the polyene antifungal antibiotics to distinguish them from a host of other miscellaneous antibiotics which also have antifungal properties. Within the next few years, reports of discoveries of new members of this class multiplied rapidly, and almost sixty are now known.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Literaturverzeichnis

  1. 1.
    Ahlers, N. H. E., R. A. Brett and N. G. MCTaggart: An Infra-Red Study of the cis-and trans-Isomers of Some C18 Fatty Acids. J. Appl. Chem.3, 433 (1953).Google Scholar
  2. 2.
    American Cyanamid Co.: Pimaricin, An Antifungal Substance. British Patent 846933 (1960).Google Scholar
  3. 3.
    Ammann, A. and D. Gottlieb: Paper Chromatography of Antifungal Antibiotics. Appl. Microbiol. 3, 181 (1955).Google Scholar
  4. 4.
    Analytical Chemistry, Editors: Spectrometry Nomenclature. Analyt. Chemistry 34, 1852 (1962).Google Scholar
  5. 5.
    Arai, T., Y. Morita and Y. Takamizawa: Studies on Antifungal Substances Extracted from the Mycelia of Streptomyces. V. On Certain Characteristics of Antifungal Substances of Mycelial Origin. J. Antibiotics (Tokyo) 7 A, 169 (1954).Google Scholar
  6. 6.
    Arcamone, F., C. Bertazzoli, G. Canevazzi, A. Di Marco, M. Ghione e A. Grein: La etruscomicina, nuovo antibiotico antifungino prodotto dallo Streptomyces lucensis N. SP. Giorn. Microbiol.4, 119 (1957).Google Scholar
  7. 7.
    Arcamone, F. e M. Perego: Isolamento e caratterizzazione di un nuovo antibiotico, la etruscomicina. Ann. chim.(Roma) 49, 345 (1959).Google Scholar
  8. 8.
    Arima, N., J. Sakamoto and E. Okamoto: Protocidin, an Antibiotic Substance. Japanese Patent 8648 (1960) [Chem. Abstr. 55, 7758 (1961)].Google Scholar
  9. 9.
    Arishima, N. and J. Sakamoto: Moldcidin A, Antibiotic Substance. Japanese Patent 1148 (1961) [Chem. Abstr. 55, 21476 (1961)].Google Scholar
  10. 10.
    Backus, E. J. and M. Dann: Biological Fungicides. German Patent 1056785 (1959).Google Scholar
  11. 11.
    Ball, S., C. J. Bessell and A. Mortimer: The Production of Polyenic Antibiotics by Soil Streptomycetes. J. Gen. Microbiol.17, 96 (1957).Google Scholar
  12. 12.
    Bartner, E., H. Zinnes, R. A. Moe and J. S. Kulesza: Studies on a New Solubilized Preparation of Amphotericin B. Antibiotics Annu.1957–1958, 53.Google Scholar
  13. 13.
    Berkoz, B. and C. Djerassi: Macrolide Antibiotics. IX. Filipin. Proc. Chem. Soc.(London) 1959, 316.Google Scholar
  14. 13a.
    Bessell, C. J., W. K. Anslow, A. M. Mortimer, D. L. Fletcher and A. Rhodes: Antifungal Antibiotic Production. U. S. Patent 3013947 (1961).Google Scholar
  15. 14.
    Bhate, D. S.: Chemistry of Polyene Antibiotics. In: T. S. Gore, B. S. Joshi, S. V. Sunthankar and B. D. Tilak, Recent Progress in the Chemistry of Natural and Synthetic Colouring Matters, p. 341. New York: Academic Press. 1962.Google Scholar
  16. 15.
    Bhate, D. S. and S. P. Acharya: Purification of Hamycin. Hindustan Antibiotics Bull.5, 16 (1962).Google Scholar
  17. 16.
    Bhate, D. S., G. R. Ambekar, K. K. Bhatnagar and R. K. Hulyalkar: Hamycin. II. Isolation and Chemical Properties. Hindustan Antibiotics Bull.3, 139 (1961).Google Scholar
  18. 16a.
    Birch, A. J.: Aspects of the Biosynthesis and Structures of Some Antibiotics. Lecture, North Jersey Section, Amer. Chem. Soc, March 26, 1963.Google Scholar
  19. 17.
    Birch, A. J., E. Pride, R. W. Rickards, P. J. Thomson, J. D. Dutcher, D. Perlman and C. Djerassi: Biosynthesis of Methymycin. Chem. and Ind.1960, 1245.Google Scholar
  20. 18.
    Borowski, E., C. P. Schaffner and H. Lechevalier: Perimycin, a Novel Type of Heptaene Antifungal Antibiotic. Antimicrobial Agents Annu.1960, 532.Google Scholar
  21. 19.
    Bristol Laboratories, Inc.: Ayfactin. British Patent 796982 (1958).Google Scholar
  22. 20.
    Brown, R. and E. L. Hazen: Capacidin, A New Member of the Polyene Antibiotic Group. Antibiot. & Chemother. 10, 702 (1960).Google Scholar
  23. 20a.
    Bu’lock, J. D., D. C. Allport and W. B. Turner: The Biosynthesis of Poly acetylenes. Part III. Poly acetylenes and Triterpenes in Polyp orus anthracophilus. J. Chem. Soc.(London) 1961, 1654.Google Scholar
  24. 21.
    Burns, J. and D. F. Holtman: Tennecetin: A New Antifungal Antibiotic. General Considerations. Antibiot. & Chemother. 9, 398 (1959).Google Scholar
  25. 22.
    Cope, A. C, R. K. Bly, E. P. Burrows, O. J. Ceder, E. Ciganek, B. T. Gillis, R. F. Porter and H. E. Johnson: Fungichromin: Complete Structure and Absolute Configuration at C26 and C27. J. Amer. Chem. Soc.84, 2170 (1962).Google Scholar
  26. 23.
    Cope, A. C. and H. E. Johnson: Fungichromin. Determination of the Structure of the Pentaene Chromophore. J. Amer. Chem. Soc.80, 1504 (1958).Google Scholar
  27. 24.
    Craveri, R. and G. Giolitti: Isolation and Study of an Antifungal Antibiotic. Ann. Microbiol.7, 81 (1956).Google Scholar
  28. 25.
    Craveri, R., A. M. Lugli, B. Sgarzi and G. Giolitti: Distribution of Antibiotic-Producing Streptomycetes in Italian Soils. Antibiot. & Chemother. 10, 306 (1960).Google Scholar
  29. 26.
    Craveri, R., O. L. Shotwell, R. G. Dworschack, T. G. Pridham and R. W. Jackson: Antibiotics Against Plant Disease. VII. The Antifungal Heptaene Component (F-17-C) Produced by Streptomyces cinnamomeus f. azacoluta. Antibiot. & Chemother. 10, 430 (1960).Google Scholar
  30. 27.
    Craveri, R. and U. Veronesi: Effect on Mitosis in A Ilium cepa of an Antifungal Antibiotic produced by Streptomyces sp. Exptl. Cell Res.11, 560 (1956).Google Scholar
  31. 28.
    Davisson, J. W., F. W. Tanner, JR., A. C. Finlay and J. H. Kane: Rimocidin and Methods for its Recovery. U. S. Patent 2963401 (1960).Google Scholar
  32. 29.
    Davisson, J. W., F. W. Tanner, JR., A. C. Finlay and I. A. Solomons: Rimocidin, A New Antibiotic. Antibiot. & Chemother. 1, 289 (1951).Google Scholar
  33. 30.
    Despois, R., S. Pinnert-Sindico, L. Ninet et J. Preud’homme: Trois antibiotiques de groupes différents produits par une même souche de Streptomyces. Giorn. Microbiol.2, 76 (1956).Google Scholar
  34. 31.
    Dhar, M. L., V. Thaller and M. C. Whiting: A New Type of Macrolide Antibiotic. Proc. Chem. Soc.(London) 1958, 148.Google Scholar
  35. 32.
    The Structures of Lagosin and Filipin. Proc. Chem. Soc.(London) 1960, 310.Google Scholar
  36. 33.
    Dhar, M. L., V. Thaller, M. C. Whiting, R. Ryhage, S. Ställberg-Sten-Hagen and E. Stenhagen: The Carbon Skeleton of Lagosin (Antibiotic A-246). Proc. Chem. Soc.(London) 1959, 154.Google Scholar
  37. 34.
    Divekar, P. V., J. L. Bloomer, J. F. Eastham, D. F. Holtman and D. A. Shirley: The Isolation of Crystalline Tennecetin and the Comparison of this Antibiotic with Pimaricin. Antibiot. & Chemother. 11, 377 (1961).Google Scholar
  38. 55.
    Djerassi, C., M. Ishikawa, H. Budzikiewicz, J. N. Shoolery and L. F. Johnson: The Structure of the Macrolide Antibiotic Filipin. Tetrahedron Letters 1961, No. 12, 383.Google Scholar
  39. 36.
    Djerassi, C., P. C. Seidel, J. Westley, A. J. Birch, C. W. Holzapfel, R. W. Rickards, J. D. Dutcher and R. Thomas: Biosynthetic Approaches to Structure Determination: Nystatin. Abstr. Papers, 142nd Meeting, Amer. Chem. Soc, Sept. 1962, p. 5 P.Google Scholar
  40. 37.
    Donovick, R., B. A. Steinberg, J. D. Dutcher and J. Vandeputte: Biological and Chemical Characteristics of Amphotericin B. Giorn. Microbiol.2, 147 (1956).Google Scholar
  41. 38.
    Dutcher, J. D.: The Chemistry of Nystatin and Related Antibiotics. Monographs on Therapy, Squibb Inst. Med. Res., New Brunswick, N. J. 2, No. 1, 87 (1957).Google Scholar
  42. 39.
    Dutcher, J. D., G. Boyack and S. Fox: The Preparation and Properties of Crystalline Fungicidin (Nystatin). Antibiotics Annu.1953–1954, 191.Google Scholar
  43. 40.
    Dutcher, J. D., W. Gold, J. F. Pagano and J. Vandeputte: Amphotericin B and its Salts. U. S. Patent 2908611 (1959).Google Scholar
  44. 41.
    Dutcher, J. D., D. R. Walters and O. P. Wintersteiner: Studies of the Chemical Properties and Structure of Nystatin (Mycostatin). In: T. H. Stern-berg and V. D. Newcomer, Therapy of Fungus Diseases, p. 168. Boston: Little, Brown. 1955.Google Scholar
  45. 42.
    Dutcher, J. D., M. B. Young, J. H. Sherman, W. Hibbits and D. R. Walters: Chemical Studies on Amphotericin B. I. Preparation of the Hydrogenation Product and Isolation of Mycosamine, An Acetolysis Product. Antibiotics Annu. 1956-1957, 866.Google Scholar
  46. 43.
    Fujita, H.: Chemical Study of Akitamycin, An Antifungal Antibiotic. J. Antibiotics (Tokyo) 12 B, 297 (1959).Google Scholar
  47. 43a.
    Gardner, J. N., G. Lowe and G. Read: Chemistry of the Higher Fungi. Part XII. The Enzymic Decarboxylation of an αβ-Acetylenic Acid. J. Chem. Soc.(London) 1961, 1532.Google Scholar
  48. 44.
    Gatenbeck, S.: The Biosynthesis of Oxytetracycline. Biochem. Biophys. Res. Commun. 6, 422 (1962).Google Scholar
  49. 45.
    Gilner, D. and P. R. Srinivasan: The Biosynthesis of Magnamycin, a Macrolide Antibiotic. Biochem. Biophys. Res. Commun. 8, 299 (1962).Google Scholar
  50. 46.
    Gold, W., H. A. Stout, J. F. Pagano and R. Donovick: Amphotericins A and B, Antifungal Antibiotics Produced by a Streptomycete. I. In-Vitro Studies. Antibiotics Annu. 1955-1956, 579.Google Scholar
  51. 47.
    Gottlieb, D., A. Ammann and H. E. Carter: A New Antifungal Agent, Filipin. Plant Disease Reporter 39, 219 (1955).Google Scholar
  52. 48.
    Gottlieb, D. and H. L. Pote: Tetrin, an Antifungal Antibiotic. Phytopathology 50, 817 (1960).Google Scholar
  53. 48.
    Grisebach, H. und H. Achenbach: Zur Biogenese der Makrolide. Öber die Herkunft der Aldehydgruppe des Magnamycins. Tetrahedron Letters 13, 569 (1962).Google Scholar
  54. 50.
    Grisebach, H., H. Achenbach und U. C. Grisebach: Zur Biogenese des Erythromycins. Naturwiss. 47, 206 (1960).Google Scholar
  55. 51.
    Hagemann, G., G. Nomine and L. Pénasse: Antifungin 4915. German Patent 1053 738 (1959).Google Scholar
  56. 51a.
    Hattori, K.: Studies on Trichomycin. VIL Structure of C21 Aldehyde. VIII. Chemical Structure of Trichomycin A. J. Antibiotics (Tokyo) 15 B, 37 (1962) [Chem. Abstr. 58, 5532 (1963)].Google Scholar
  57. 52.
    Hattori, K., H. Nakano, M. Seki and Y. Hirata: Studies on Trichomycin. IV. J. Antibiotics (Tokyo) 9 A, 176 (1956).Google Scholar
  58. 53.
    Hausser, K. W., R. Kuhn und G. Seitz: Lichtabsorption und Doppelbindung. V. Über die Absorption von Verbindungen mit konjugierten Kohlenstoff doppelbindungen bei tiefer Temperatur. Z. physik. Chem.29 B, 391 (1935).Google Scholar
  59. 54.
    Hazen, E. L. and R. Brown: TWO Antifungal Agents Produced by a Soil Actinomycete. Science (Washington) 112, 423 (1950).Google Scholar
  60. 55.
    Henis, Y., N. Grossowicz and M. Aschner: Heptamycin, an Antifungal and Antiprotozoal Antibiotic. Bull. Res.Council Israel 6 E, VII (1957).Google Scholar
  61. 56.
    Hickey, R. J.: The Antagonism Between the Antifungal Antibiotic, Ascosin, and Some Long-Chain, Unsaturated Fatty Acids. Arch. Biochem. Biophys. 46, 331 (1953).Google Scholar
  62. 57.
    Hickey, R. J., C. J. Corum, P. H. Hidy, I. R. Cohen, U. F. B. Nager and E. Kropp: Ascosin, An Antifungal Antibiotic Produced by a Streptomycete. Antibiot. & Chemother.2, 472 (1952).Google Scholar
  63. 58.
    Hosoya, S. and N. Hamamura: A New Solvent for the Purification of the Antifungal Antibiotics Belonging to the Trichomycin Group. J. Antibiotics (Tokyo) 9 A, 129 (1956).Google Scholar
  64. 59.
    Hosoya, S., N. Komatsu, M. Soeda and Y. Sonoda: Trichomycin, a New Antibiotic Produced by Streptomyces hachijoensis with Trichomonadicidal and Antifungal Activity. Japan J. Exp. Med. 22, 595 (1952) [Cftem. Abstr. 48, 3444 (1952)].Google Scholar
  65. 60.
    Hosoya, S., N. Komatsu, M. Soeda, T. Yunaguchi and Y. Sonoda: Trichomycin, A New Antibiotic With Trichomonicidal and Antifungal Activities. J. Antibiotics (Tokyo) 5 A, 564 (1952).Google Scholar
  66. 61.
    Igarashi, M., K. Ogata and A. Miyake: An Antifungal Substance Produced by Streptomyces aureofaciens. J. Antibiotics (Tokyo) 9 B, 79 (1956) [Chem. Abstr. 53, 20 251 (1959)].Google Scholar
  67. 62.
    Igarashi, M., K. Ogata and A. Miyake Streptomyces Pentaene Group Substances. I. An Antifungal Antibiotic Produced by Streptomyces acidomyceticus. J. Antibiotics (Tokyo) 9 B, 101 (1956) [Chem. Abstr. 53, 22224 (1959)].Google Scholar
  68. 62 a.
    Jones, E. R. H.: Pedler Lecture: Polyacetylenes. Proc. Chem. Soc.(London) 1960, 199.Google Scholar
  69. 63.
    Kaplan, M. A., B. Heinemann, I. Mydlinski, F. H. Buckwalter, J. Lein and I. R. Hooper: An Antifungal Antibiotic (AYF) Produced by a Strain of Streptomyces aureofaciens. Antibiot. & Chemother. 8, 491 (1958).Google Scholar
  70. 64.
    Katz, E. and H. Lechevalier: Nutritional Control of Antibiotic Synthesis as Applied to Actinomycin and the Polyene Antifungal Antibiotics. In: Recent Advances in Botany, p. 657. Toronto: Univ. of Toronto Press. 1961.Google Scholar
  71. 65.
    Kaufmann, H. P. und R. K. Sud: Zur Stereochemie der vierfach konjugiert-ungesättigten Parinärsäuren. Chem. Ber.92, 2797 (19Google Scholar
  72. 66.
    Koe, B. K., F. W. Tanner, JR., K. V. Rao, B. A. Sobin and W. D. Celmer: PA 150, PA 153, and PA 166: New Polyene Antifungal Antibiotics. Antibiotics Annu. 1957-1958, 897.Google Scholar
  73. 67.
    Kuroya, M.: Antibiotic Substance, Flavacid. Japanese Patent 8547 (1954) [Chem. Abstr.50, 9696 (1956)].Google Scholar
  74. 68.
    Lechevalier, H., R. F. Acker, C. T. Corke, C. M. Haenseler and S. A. Waksman: Candicidin, A New Antifungal Antibiotic. Mycologia 45, 155 (1953).Google Scholar
  75. 69.
    Lindner, F., J. Schmidt-Thomé, K. Kühn, G. Nesemann, A. Steigler and K. H. Wallhäusser: Antifungal Antibiotic. German Pat. 1017329 (1957) [Chem. Abstr.55, 898 (1961)].Google Scholar
  76. 70.
    Lindner, F., J. Schmidt-Thomé, K. H. Wallhäusser and H. Weidenmüller: Fungicidal Antibiotic. German. Pat. 1012 430 (1957) [Chem. Abstr. 54, 6045 (196Google Scholar
  77. 71.
    Loeb, J. N., P. K. Brown and G. Wald: Cis-trans Isomerism and Steric Hindrance. Nature (London) 184, 617 (1959).Google Scholar
  78. 72.
    Maeda, K., K. Oi, H. Kosaka, E. Lin Wang and H. Umezawa: Simultaneous Production of an Actinomycin and a Eurocidin-Group Antibiotic. J. Antibiotics (Tokyo) 9 A, 125 (1956).Google Scholar
  79. 73.
    Matsuoka, M. and H. Umezawa: Unamycin, An Antifungal Substance Produced by Streptomyces fungicidicus. J. Antibiotics (Tokyo) 13 A, 114 (1960).Google Scholar
  80. 74.
    Mebane, A. D.: 1,3,5,7,9-Decapentaene and 1,3,5,7,9,11,13-Tetradeca-heptaene. J. Amer. Chem. Soc, 74, 5227 (1952).Google Scholar
  81. 75.
    Mebane, A. D. and W. Oroshnik: Unpublished observations.Google Scholar
  82. 76.
    Nakano, H.: Studies on Trichomycin. V. J. Antibiotics (Tokyo) 14 A, 68 (1961).Google Scholar
  83. 77.
    Nakano, H.: Studies on Trichomycin. VI.J. Antibiotics (Tokyo) 14 A, 72 (1961).Google Scholar
  84. 78.
    Nakano, H., K. Hattori, M. Seki and Y. Hirata: Trichomycin. III. J. Antibiotics (Tokyo) 9 A, 172 (1956).Google Scholar
  85. 79.
    Nakazawa, K.: Streptomycetes. III. Eurocidin, An Antibiotic Produced by 5. albireticuli. J. Agr. Chem. Soc.Japan 29, 650 (1955) [Chem. Abstr. 50, 5830 (1956)].Google Scholar
  86. 80.
    Nayler, P. and M. C. Whiting: Researches on Polyenes. Part III. The Synthesis and Light Absorption of Dimethylpolyenes. J. Chem. Soc.(London) 1955, 3037.Google Scholar
  87. 81.
    Nefelova, M. V. and I. N. Pozmogova: Culturing Actinomycetes Producing Antibiotics Toxic to Fungi. Mikrobiologiya 29, 856 (1960) [Chem. Abstr. 55, 14586 (1961)].Google Scholar
  88. 82.
    Ogata, K., S. Igarashi and Y. Nakao: Culture Medium for Separation of Bacteria from Mixtures of Bacteria, Yeasts, and Molds. Japanese Patent 9245 (1958) [Chem. Abstr.53, 6545 (1959)].Google Scholar
  89. 83.
    Ogawa, H., T. Ito, S. Inoue and M. Nishio: Chemical Study on Moldcidin B and its identification with Pentamycin. J. Antibiotics (Tokyo) 13 A, 353 (1960).Google Scholar
  90. 84.
    Okami, Y., R. Utahara, S. Nakamura and H. Umezawa: Studies on Antibiotics from Actinomycetes. IX. J. Antibiotics (Tokyo) 7 A, 98 (1954).Google Scholar
  91. 85.
    Oroshnik, W., L. C. Vining, A. D. Mebane and W. A. Taber: Polyene Antibiotics. Science (Washington) 121, 147 (1955).Google Scholar
  92. 86.
    Oswald, E. J., R. J. REEDY and W. A. Randall: An Antifungal Agent, 1968, Produced by a New Streptomyces Species. Antibiotics Annu. 1955-1956, 236.Google Scholar
  93. 87.
    Pao, scch’in-chu, P.-Y. Kung and J.-S. Ts’ai: Fungicidin A-94. II. Preparation and Chemical Characteristics. K’O Hsüeh T’UNG Pao 24, 825 (1959) [Chem. Abstr.54, 20054 (1960)].Google Scholar
  94. 88.
    Parke, Davis & Co.: Sistomycosin. British Patent 712547 (1954).Google Scholar
  95. 89.
    Patrick, J. B., R. P. Williams, C. F. Wolf and J. S. Webb: Pimaricin. I. Oxidation and Hydrolysis Products. II. The Structure of Pimaricin. J. Amer. Chem. Soc.80, 6688, 6689 (1958).Google Scholar
  96. 90.
    Pledger, R. A. and H. Lechevalier: Survey of the Production of Polyenic Substances by Soil Streptomycetes. Antibiotics Annu. 1955-1956, 249.Google Scholar
  97. 91.
    Rabinowitch, E. and L. F. Epstein: Polymerization of Dyestuffs in Solution. Thionine and Methylène Blue. J. Amer. Chem. Soc.63, 69 (19Google Scholar
  98. 92.
    Rao, K. V., W. S. MARSH and A. L. Garretson: Biologically Active Substances. German Patent 1052065 (1959) [Chem. Abstr.55, 18009 (1961)].Google Scholar
  99. 93.
    Raubitscheck, F., R. F. Acker and S. A. Waksman: Production of an Antifungal Agent of the Fungicidin Type by 5. aureus. Antibiot. & Chemother. 2, 179 (1952).Google Scholar
  100. 93a.
    Richardson, A. C.: The Synthesis and Stereochemistry of Mycaminose. Proc. Chem. Soc.(London) 1961, 430.Google Scholar
  101. 94.
    Ross, W. C. J.: The Reactions of Certain Epoxides in Aqueous Solution. J. Chem. Soc.(London) 1950, 2257.Google Scholar
  102. 95.
    Sakamoto, J. M. J.: Étude sur antibiotique antifongique. I. La protocidine, un nouvel antibiotique produit par les Streptomycete. J. Antibiotics (Tokyo) 10 A, 128 (1957).Google Scholar
  103. 96.
    Sakamoto, J. M. J.: Étude sur antibiotique antifongique. II. La cryptocidine, un nouvel antibiotique produit par les Streptomycete. J. Antibiotics (Tokyo) 12 A, 21 (1959).Google Scholar
  104. 97.
    Sakamoto, J. M. J.: Étude sur antibiotique antifongique. III. La moldci-dine A, un nouvel antibiotique produit par les Streptomycete. J. Antibiotics (Tokyo) 12 A, 169 (1959).Google Scholar
  105. 98.
    Schaffner, C. P.: Personal communication.Google Scholar
  106. 99.
    Schaffner, C. P. and E. Borowski: Biologically Active N-Acyl Derivatives of Polyene Macrolide Antifungal Antibiotics. Antibiot. & Chemother. 11, 724 (1961).Google Scholar
  107. 100.
    Schaffner, C. P., I. D. Steinman, R. S. Safferman and H. Lechevalier: Role of Inorganic Salts and Mevalonic Acid in the Production of a Tetraenic Antifungal Antibiotic. Antibiotics Annu. 1957-1958, 869.Google Scholar
  108. 101.
    Schnabel, E., H. NöTHER and H. Kuhn: Monomers, Dimers, and Tetramers in Solutions of Phthalocyanine Sulphonates. In: T. S. Gore et al., Recent Progress in the Chemistry of Natural and Synthetic Colouring Matters, p. 561. New York: Academic Press. 1962.Google Scholar
  109. 102.
    Shibata, M., M. Honjo, Y. Tokui and K. Nakazawa: On a New Antifungal and Antiyeast Substance, Candimycin, Produced by a Streptomyces. J. Antibiotics (Tokyo) 7 B, 168 (1954).Google Scholar
  110. 103.
    Shibata, Y., K. Tanabe, A. Miyake, Y. Tokui, S. Yoshishiro, J. Kaneko, S. Fujii, K. Oki, I. Tadokoro and K. Nakazawa: Enteromycin, a New Antibiotic. Japanese Patent 4995 (1956) [Chem. Abstr.52, 9529 (1958)].Google Scholar
  111. 103a.
    Smakula, A.: Über physikalische Methoden im chemischen Laboratorium. XXII. Lichtabsorption und chemische Konstitution. Angew. Chem.47, 657 (1934).Google Scholar
  112. 104.
    Smakula, A.: Società Farmaceutici Italia: The Fermentative Production of the Antibiotics Distamycine and Distacyne. British Patent 872734 (1961).Google Scholar
  113. 105.
    Soeda, M. and H. Fujita: Akitamycin, An Antifungal Antibiotic. J. Antibiotics (Tokyo) 12 B, 293 (1959) [Chem. Abstr. 54, 14359 (1960)].Google Scholar
  114. 106.
    Soeda, M. and H. Fujita: An Antifungal Antibiotic, Eurotin A. J. Antibiotics (Tokyo) 12 B, 368 (1959) [Chem. Abstr. 54, 16644 (1960)].Google Scholar
  115. 107.
    Sondheimer, F., D. A. Ben-efraim and R. Wolovsky: Unsaturated Macro-cyclic Compounds. XVII. The Prototropic Rearrangement of Linear 1,5-Enynes to Conjugated Polyenes. The Synthesis of a Series of Vinylogs of Butadiene. J. Amer. Chem. Soc.83, 1675 (1961).Google Scholar
  116. 108.
    Staron, T. et A. Faivre-amiot: Isolement et propriétés physicochimiques d’un nouvel antibiotique antifongale. C. R. hebd. Séances Acad. Sci.250, 1730 (1960).Google Scholar
  117. 109.
    Struyk, A. P., I. Hoette, G. Drost, J. M. Waisvisz, T. Van eek and J. C. Hoogerheide: Pimaricin, A New Antifungal Antibiotic. Antibiotics Annu. 1957–1958, 878.Google Scholar
  118. 110.
    Taber, W. A. and L. C. Vining: A Comparison of the Antifungal Antibiotics Candidin, Ascosin, Candicidin, and Trichomycin. Bacteriol. Proc. (Soc. Amer. Bacteriologists) 54, 86 (1954).Google Scholar
  119. 111.
    Taber, W. A., L. C. VINING and S. A. Waksman: Candidin, A New Antifungal Antibiotic Produced by Streptomyces viridoflavus. Antibiot. & Chemother. 4, 455 (1954).Google Scholar
  120. 112.
    Takahashi, L: Studies on Antibiotic Substances from Actinomycetes. XXVII. A New Antifungal Substance, Flavacid. J. Antibiotics (Tokyo) 6 A, 117 (1953).Google Scholar
  121. 113.
    Thrum, H.: Eine neue, von einer Spezies der Streptomyces reticuli-Gruppe gebildete Antibiotikakombination. Naturwiss. 46, 87 (1959).Google Scholar
  122. 114.
    Thrum, H.:Stoffwechselprodukte und Antibiotika von Streptomyces I A 2814, einem Streptomyces-Netropsis-Stamm. Planta Med.8, 376 (1960).Google Scholar
  123. 115.
    Tsyganov, V. A., P. N. Golyakov, A. M. Bezborodov, U. P. Namestnikova, G. V. Khopko, S. N. Solov’ev, M. A. Malyshkina and L. O. Bol’shakova: Antifungal Antibiotic 26/1. Antibiotiki 4, 21 (1959) [Chem. Abstr. 53, 19167 (1959)].Google Scholar
  124. 116.
    Tsyganov, V. A., P. N. Golyakov, S. N. Solov’ev, B. G. Belen’kii and A. I. Filippova: Antibiotic Substances of the Polyene Type. I. The Biological Properties of Actinomycetes Producing Polyene Antibiotics. II. Physico-chemical Properties of Polyene Antibiotics. Sbornik Nauch. Trudov Leningrad. Nauch-Issledovatel.Inst. Antibiotikov 2, 6, 13 (1960) [Chem. Abstr. 55, 17751, 22703 (1961)].Google Scholar
  125. 117.
    Tsyganov, V. A., P. N. Golyakov, S. N. Solov’ev, B. G. Belen’kii and A. I. Filippova: Antibiotic Properties and Systematic Position of Some Actinomycetes of the Globisporus Group. II. Trudy Inst. Mikrobiol., Akad.Nauk S. S. S. R. 1960, 182 [Chem. Abstr. 55, 10585 (1961)].Google Scholar
  126. 118.
    Tytell, A. A., F. J. Mccarthy, W. P. Fisher, W. A. Bolhofer and J. Charney: Fungichromin and Fungichromatin: New Polyene Antifungal Agents. Antibiotics Annu. 1954–1955, 716.Google Scholar
  127. 119.
    Mezawa, H. and M. Nagase: Unamycin, A New Antifungal Substance. Japanese Patent 3392 (1959) [Chem. Abstr.53, 20708 (1959)].Google Scholar
  128. 120.
    Umezawa, H., Y. Okami and R. Kihara: New Antibiotic Substance Obtained from Streptomyces abikoensis. Japanese Patent 9346 (1955) [Chem. Abstr.51, 18495 (1957)].Google Scholar
  129. 121.
    Umezawa, S., S. Nakada and H. Onuma: Isolation of 2-Methyl-2, 4,6,8,10-dodecapentaenedial from the Oxidative Degradation of Pentamycin. J. Antibiotics (Tokyo) 11 A, 273 (1958).Google Scholar
  130. 122.
    Umezawa, S., M. Ooka and S. Shiozu: Pentamycin, A New Antibiotic. Japanese Patent 6000 (1959) [Chem. Abstr.53, 22764 (195Google Scholar
  131. 123.
    Umezawa, S., Y. Tanaka, M. Ooka and S. Shiotzu: A New Antifungal Antibiotic, Pentamycin. J. Antibiotics (Tokyo) 11 A, 26 (1958).Google Scholar
  132. 124.
    Utahara, R., Y. Okami, S. Nakamura and H. Umezawa: A New Antifungal Substance, Mediocidin, and Other Antifungal Substances of Streptomyces with Three Characteristic Absorption Maxima. J. Antibiotics (Tokyo) 7 A, 120 (1954).Google Scholar
  133. 125.
    Vandeputte, J., J. L. Wachtel and E. T. Stiller: Amphotericins A and B, Antifungal Antibiotics Produced by a Streptomycete. II. The Isolation and Properties of the Crystalline Amphotericins. Antibiotics Annu. 1955-1956, 587.Google Scholar
  134. 126.
    Vaněk, Z., L. Doležilová and Z. scřehácěk: Formation of a Mixture of Antibiotic Substances Including Antibiotics of a Polyene Character, by Strains of Actinomycetes Freshly Isolated from Soil Samples. J. Gen. Microbiol. 18, 649 (19Google Scholar
  135. 127.
    Vining, L. C.: The Polyene Antifungal Antibiotics. Hindustan Antibiot. Bull.3, 37 (1960).Google Scholar
  136. 128.
    Vining, L. C. and W. A. Taber: Preparation and Properties of Crystalline Candidin. Canad. J. Chem. 34, 1163 (1956).Google Scholar
  137. 129.
    Vining, L. C. and W. A. Taber:Separation of Endomycins A and B, and their identification as Members of the Polyene Group of Antifungal Antibiotics. Canad. J. Chem.35, 1461 (1957).Google Scholar
  138. 130.
    Vining, L. C, W. A. Taber and F. J. Gregory: The Candidin-Candicidin Group of Antifungal Antibiotics. Antibiotics Annu.1954–1955, 980.Google Scholar
  139. 130a.
    VON Saltza, M. H., J. Reid, J. D. Dutcher and O. Wintersteiner: Nystatin. II. Stereochemistry of Mycosamine. J. Amer. Chem. Soc.83, 2785 (1961).Google Scholar
  140. 131.
    Wakaki, S., S. Akanabe, K. Hamada and T. Asahina: Antifungal Substances Produced by Actinomycetes. Antibiotic from Strain C-6. J. Antibiotics (Tokyo) 5, 677 (1952).Google Scholar
  141. 132.
    Wakaki, S., K. Hamada, S. Akanabe and T. Asahina: Studies of an Antifungal Antibiotic from Streptomyces, IV. On the Physico-Chemical Properties of Chromin. J. Antibiotics (Tokyo) 6 A, 145 (1953); 6 B, 247 (1953).Google Scholar
  142. 133.
    Walters, D. R., J. D. Dutcher and O. Wintersteiner: Structure of Mycosamine. J. Amer. Chem. Soc.79, 5076 (1957).Google Scholar
  143. 134.
    Whitfield, G. B., T. D. Brock, A. Ammann, D. Gottlieb and H. E. Carter: Filipin, an Antifungal Antibiotic: Isolation and Properties. J. Amer. Chem. Soc.77, 4799 (1955).Google Scholar
  144. 135.
    Woods, G. F. and L. H. Schwartzman: 1,3,5,7-Octatetraene. J. Amer. Chem. Soc.71, 1396 (1949).Google Scholar
  145. 136.
    Woodward, R. B.: The Structure and Biogenesis of the Macrolides, a New Class of Natural Products. In: Festschrift Arthur Stoll, p. 524. Basel: Birk-häuser. 1957.Google Scholar
  146. 137.
    Wooldridge, W. E.: Fungicidal and Antibiotic Substances from Streptomyces aminophilus. German Patent 1000966 (1957) [Chem. Abstr.54, 23177 (1960)].Google Scholar
  147. 138.
    Wooldridge, W. E.: Antifungal Antibiotic. British Patent 828792 (1960).Google Scholar
  148. 139.
    Yajima, T.: On the Classification of Antifungal Antibiotics. J. Antibiotics (Tokyo) 8 A, 189 (1955).Google Scholar
  149. 140.
    Zechmeister, L.: Cis-trans Isomeric Carotenoids, Vitamins A, and Aryl-polyenes, pp. 30–44. Vienna: Springer-Verlag, and New York: Academic Press. 1962.Google Scholar

Copyright information

© Springer-Verlag/Wien 1963

Authors and Affiliations

  • W. Oroshnik
    • 1
  • A. D. Mebane
    • 2
  1. 1.CliftonUSA
  2. 2.RaritanUSA

Personalised recommendations