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The Natural Functions of Secondary Metabolites

  • Arnold L. Demain
  • Aiqi Fang
Part of the Advances in Biochemical Engineering/Biotechnology book series (ABE, volume 69)

Abstract

Secondary metabolites, including antibiotics, are produced in nature and serve survival functions for the organisms producing them. The antibiotics are a heterogeneous group, the functions of some being related to and others being unrelated to their antimicrobial activities. Secondary metabolites serve: (i) as competitive weapons used against other bacteria, fungi, amoebae, plants, insects, and large animals; (ii) as metal transporting agents; (iii) as agents of symbiosis between microbes and plants, nematodes, insects, and higher animals; (iv) as sexual hormones; and (v) as differentiation effectors. Although antibiotics are not obligatory for sporulation, some secondary metabolites (including antibiotics) stimulate spore formation and inhibit or stimulate germination. Formation of secondary metabolites and spores are regulated by similar factors. This similarity could insure secondary metabolite production during sporulation. Thus the secondary metabolite can: (i) slow down germination of spores until a less competitive environment and more favorable conditions for growth exist; (ii) protect the dormant or initiated spore from consumption by amoebae; or (iii) cleanse the immediate environment of competing microorganisms during germination.

Keywords

Secondary metabolite functions Antibiosis Differentiation Metal transport Sex hormones 

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References

  1. 1.
    Demain AL, Solomon NA (1981) Scientific American 245:67Google Scholar
  2. 2.
    Fleming A (1929) J Exp Pathol 10:226Google Scholar
  3. 3.
    Florey HW, Chain EB, Heatley NG, Jennings MA, Sanders AG, Abraham EP, Florey ME (1949) Antibiotics, Vol II. Oxford University Press, LondonGoogle Scholar
  4. 4.
    Backus MP, Stauffer JF (1955) Mycologia 47:429CrossRefGoogle Scholar
  5. 5.
    Bu’Lock JD (1975) In: Smith JE, Berry R (eds) The filamentous fungi, vol 1. Wiley, New York, p 33Google Scholar
  6. 6.
    Demain AL (1995) In: Kuhn W, Fiedler H-P (eds) Sekundärmetabolismus bei Mikroorganismes; Beiträge zur Forschung, Attempto Verlag, Tübingen, p11Google Scholar
  7. 7.
    Kato K (1953) J Antibiot Ser (Tokyo) 6:130Google Scholar
  8. 8.
    Batchelor FR, Doyle FP, Nayler JHC, Rolinson GN (1959) Nature 183:257CrossRefGoogle Scholar
  9. 9.
    Gottshall RY, Roberts JM, Portwood LM, Jennings JC (1951) Proc Soc Exptl Biol Med 76:307Google Scholar
  10. 10.
    Crawford K, Heatley NG, Boyd PF, Hale CW, Kelly BK, Miller GA, Smith N (1952) J Gen Microbio l6:47Google Scholar
  11. 11.
    Newton GGF, Abraham EP (1955) Nature, 175:548CrossRefGoogle Scholar
  12. 12.
    Berdy J (1996) In: Debabov VG, Dudnik YV, Danilenko VN (eds) The biology of actinomycetes, part I. Allerton Press, New York, p 3Google Scholar
  13. 13.
    Strohl WR (1997) Biotechnology of antibiotics, 2nd edn. Marcel Dekker, New YorkGoogle Scholar
  14. 14.
    Demain AL (1975) Chem Technol 5:287Google Scholar
  15. 15.
    Demain AL (1983) Science 219:709CrossRefGoogle Scholar
  16. 16.
    Umezawa H (1972) Enzyme inhibitors of microbial origin. University of Tokyo Press, TokyoGoogle Scholar
  17. 17.
    Omura S (1992) J Indust Microbiol 10:135CrossRefGoogle Scholar
  18. 18.
    Skatrud PL, Tietz AJ, Ingolia TD, Cantwell CA, Fisher DL, Chapman JL, Queener SW (1989) Bio/Technology 7:477CrossRefGoogle Scholar
  19. 19.
    Khosla C, Caren R, Kao CM, McDaniel R, Wang S-W (1996) Biotechnol Bioeng 52:122CrossRefGoogle Scholar
  20. 20.
    Verdine GL (1996) Nature 384[Suppl]: 11Google Scholar
  21. 21.
    Cragg GM, Newman DJ, Snader KM (1997) J Nat Prod 60:52CrossRefGoogle Scholar
  22. 22.
    Clark AM (1996) Pharmaceut Res 13:1133CrossRefGoogle Scholar
  23. 23.
    Gloer JB (1993) Devel Ind Microbiol 33:1Google Scholar
  24. 24.
    Foster HA, Yasouri FN, Daoud NN (1992) FEMS Microbiol Ecol 101:27CrossRefGoogle Scholar
  25. 25.
    Reichenbach H, Gerth K, Irschik H, Kunze B, Hofle G (1988) Trends Biotechnol 6:115CrossRefGoogle Scholar
  26. 26.
    Reichenbach H, Hofle G (1993) Biotechnol Adv 11:219CrossRefGoogle Scholar
  27. 27.
    Miyadoh S (1993) Actinomycetologia 7:100CrossRefGoogle Scholar
  28. 28.
    Zedan H (1993) SIM News 43:178Google Scholar
  29. 29.
    Fenical W, Jensen PR (1993) In: Attaway DH, Zaborsky OR (eds) Marine biotechnology I. Pharmaceutical and bioactive natural products. Plenum, New York, p 419Google Scholar
  30. 30.
    Berdy J (1994) Abstract C2, Internat Conf Sec Metab, InterlakenGoogle Scholar
  31. 31.
    Zähner H (1987) In: Chmiel H, Hammes WP, Bailey JE (eds) Biochemical engineering. Fischer, Stuttgart, p 136Google Scholar
  32. 32.
    Connolly JD, Hill RA (1991) Dictionary of terpenoids. Chapman & Hall, LondonGoogle Scholar
  33. 33.
    Vining LC, Taber WA (1979) In: Rose AH (ed) Economic microbiology, vol. 3. Secondary products of metabolism. Academic Press, London, p 389Google Scholar
  34. 34.
    Norstadt FA, McCalla TM (1969) Soil Sci 107:188CrossRefGoogle Scholar
  35. 35.
    Hesseltine CW, Rogers RF, Shotwell OL (1981) Mycologia 73:216CrossRefGoogle Scholar
  36. 36.
    Trail F, Mahanti N, Linz J (1995) Microbiology 141:755Google Scholar
  37. 37.
    Hesseltine CW (1986) In: Steyn PS, Vleggaar R (eds) Mycotoxins and phycotoxins. Elsevier Science, Amsterdam, p 1Google Scholar
  38. 38.
    Sydenham E, Gelderblom WCA, Thiel PG, Marasas WFO (1990) J Agric Food Chem 38:285CrossRefGoogle Scholar
  39. 39.
    Ishii K, Kobayashi J, Ueno Y, Ichinoe M (1986) Appl Environ Microbiol 52:331Google Scholar
  40. 40.
    Kim J-C, Lee Y-W, Yu S-H (1995) Appl Environ Microbiol 61:3750Google Scholar
  41. 41.
    Castignetti D, Smarrelli J Jr (1986) FEBS Lett 209:147CrossRefGoogle Scholar
  42. 42.
    Baquero F, Asensio C (1979) In: van der Waaij D, Verhoef J (eds) New criteria for antimicrobial therapy: maintenance of digestive tract colonization resistance. Exerpta Medica, Amsterdam, p 90Google Scholar
  43. 43.
    Rinehart KL, Namikoshi M, Choi BW (1994) J Appl Phycol 6:159CrossRefGoogle Scholar
  44. 44.
    Demain AL (1980) Search 11:148Google Scholar
  45. 45.
    Howell CR, Stipanovic RD (1983) Can J Microbiol 29:321CrossRefGoogle Scholar
  46. 46.
    Gray TR (1976) Symp Soc Gen Microbiol 26:327Google Scholar
  47. 47.
    Bennett JW (1983) In: Bennett JW, Ciegler A (eds) Secondary metabolism and differentiation in fungi. Marcel Dekker, New York, p 1Google Scholar
  48. 48.
    Campbell IM (1984) Adv Microb Physiol 25:1CrossRefGoogle Scholar
  49. 49.
    Campbell IM, Doerfler DL, Bird BA, Remaley AT, Rosato LM, Davis BN (1982) In: Krumphanzl V, Sikyta B, Vanek Z (eds) Overproduction of microbial products. Academic Press, London, p 141Google Scholar
  50. 50.
    Jensen PR, Fenical W (1994) Annu Rev Microbiol 48:559CrossRefGoogle Scholar
  51. 51.
    Williams DH, Stone MJ, Hauck PR, Rahman SK (1989) J Nat Prod 52:1189CrossRefGoogle Scholar
  52. 52.
    Stone MJ, Williams DH (1992) Mol Microbiol 6:29CrossRefGoogle Scholar
  53. 53.
    Katz E, Demain AL (1977) Bacteriol Rev 41:449Google Scholar
  54. 54.
    Demain AL (1989) In: Hershberger CL, Queener SW, Hegeman G (eds) Genetics and molecular biology of industrial microorganisms. American Society for Microbiology, Washington DC, p 1Google Scholar
  55. 55.
    Hopwood DA (1988) Proc R Soc Lond B235:121Google Scholar
  56. 56.
    Davies J (1990) Mol Microbiol 4:1227CrossRefGoogle Scholar
  57. 57.
    Cavalier-Smith T (1992) In: Chadwick DJ, Whelan J (eds) Secondary metabolites: their function and evolution. Wiley, Chichester, p 64CrossRefGoogle Scholar
  58. 58.
    Bruehl GW, Millar RL, Cunfer B (1969) Can J Plant Sci 49:235Google Scholar
  59. 59.
    Gloer JB (1995) Can J Bot 73:1265CrossRefGoogle Scholar
  60. 60.
    Schirmböck M, Lorito M, Wang Y-L, Hayes CK, Arisan-Atac I, Scala F, Harman GE, Kubicek CP (1994) Appl Environ Microbiol 60:4364Google Scholar
  61. 61.
    Ayer WA, Lee SP, Tsuneda A, Hiratsuka Y (1980) Can J Microbiol 26:766CrossRefGoogle Scholar
  62. 62.
    Kerr A, Tate ME (1984) Microbiol Sci 1:1Google Scholar
  63. 63.
    Rosenberg E, Varon M (1984) In: Rosenberg E (ed) Myxobacteria. development and cell interactions. Springer, Berlin Heidelberg New York, p 104Google Scholar
  64. 64.
    Lampson BC (1988) Bio/Technology 6:878CrossRefGoogle Scholar
  65. 65.
    Smith DR, Dworkin M (1994) J Bacteriol 176:1201Google Scholar
  66. 66.
    Lemos ML, Dopazo CP, Toranzo AE, Barja JL (1991) J Appl Bacteriol 71:228Google Scholar
  67. 67.
    Ruiz-Barba JL, Cathcart DP, Warner PJ, Jiménez-Diaz (1994) Appl Environ Microbiol 60:2059Google Scholar
  68. 68.
    Axelrod PE, Rella M, Schroth MN (1988) Appl Environ Microbiol 54:1222Google Scholar
  69. 69.
    Messenger AJM, Turner JM (1981) Soc Gen Microbiol Quart 8:263Google Scholar
  70. 70.
    Habte M, Alexander M (1977) Arch Microbiol 113:181CrossRefGoogle Scholar
  71. 71.
    Singh BN (1942) Nature 149:168CrossRefGoogle Scholar
  72. 72.
    Groscop JA, Brent MM (1964) Can J Microbiol 10:579Google Scholar
  73. 73.
    Imshenetskii AA (1974) Mikrobiologiya 43:185Google Scholar
  74. 74.
    Singh BN (1945) Br J Exp Pathol 26:316Google Scholar
  75. 75.
    Bird DF, Kalff J (1986) Science 231:493CrossRefGoogle Scholar
  76. 76.
    Fischer HP, Bellus D (1983) Pestic Sci 14:334CrossRefGoogle Scholar
  77. 77.
    Gasson MJ (1980) Appl Environ Microbiol 39:25Google Scholar
  78. 78.
    Staskawicz BJ, Panopoulos NJ (1979) Phytopathology 69:663CrossRefGoogle Scholar
  79. 79.
    Patil SS (1974) Annu Rev Phytopathol 12:259CrossRefGoogle Scholar
  80. 80.
    Strobel GA (1977) Annu Rev Microbiol 31:205CrossRefGoogle Scholar
  81. 81.
    Xu G-W, Gross DC (1988) J Bacteriol 170:5680Google Scholar
  82. 82.
    Mo Y-Y, Gross DC (1991) J Bacteriol 173:5784Google Scholar
  83. 83.
    Mitchell RE (1991) Experientia47:791CrossRefGoogle Scholar
  84. 84.
    Knight TJ, Durbin RD, Langston-Unkefer PJ (1986) J Bacteriol 166:224Google Scholar
  85. 85.
    Rott PC, Costet L, Davis MJ, Frutos R, Gabriel DW (1996) J Bacteriol 178:4590Google Scholar
  86. 86.
    Birch PG, Patil SS (1987) Physiol Mol Plant Pathol 30:199,207Google Scholar
  87. 87.
    Miller-Wideman M, Makkar N, Tran M, Isaac B, Biest N, Stonard R (1992) J Antibiot 45:914Google Scholar
  88. 88.
    Scheffer RP (1991) Experientia 47:804CrossRefGoogle Scholar
  89. 89.
    Strobel G, Kenfield D, Bunkers G, Sugawara F, Clardy J (1991) Experientia 47:819CrossRefGoogle Scholar
  90. 90.
    Desjardins AE, Proctor RH, Bai G, McCormick SP, Shaner G, Buechley G, Hohn TM (1996) Mol Plant-Microbe Interact 9:775Google Scholar
  91. 91.
    Lee S, Aoyagi H, Shimohigashi Y, Izumiya N, Ueno T, Fukami H (1976) Tetrahedron Lett 843Google Scholar
  92. 92.
    Robeson DJ, Strobel GA (1982) Phytochemistry 21:1821CrossRefGoogle Scholar
  93. 93.
    Stierle AC, Cardellina JH II, Strobel GA (1988) Proc Natl Acad Sci USA 85:8008CrossRefGoogle Scholar
  94. 94.
    Iwasaki S, Kobayashi H, Furukawa J, Namikoshi M, Okuda S, Sato Z, Matsuda I, Noda T (1984) J Antibiot 37:354Google Scholar
  95. 95.
    Sparace SA, Reeleder RD, Khanizadeh S (1987) Can J Microbiol 33:327CrossRefGoogle Scholar
  96. 96.
    Peipp H, Sonnenbichler J (1992) Bio Chem Hoppe-Seyler 373:675Google Scholar
  97. 97.
    Sonnenbichler J, Bliestle IM, Peipp H, Holdenrieder O (1989) Biol Chem Hoppe-Seyler 370:1295Google Scholar
  98. 98.
    Darvill AG, Albersheim P (1984) Annu Rev Plant Physiol 35:243CrossRefGoogle Scholar
  99. 99.
    Mitsher LA (1975) Recent Adv Phytochem 9:243Google Scholar
  100. 100.
    Bennett JW (1981) In: Vezina C, Singh K (eds) Advances in biotechnology, vol 3, fermentation Products. Pergamon, Toronto, p 409Google Scholar
  101. 101.
    Swain T (1977) Annu Rev Plant Pathol 28:479CrossRefGoogle Scholar
  102. 102.
    Kanaoka M, Isogai A, Suzuki A (1979) Agric Biol Chem 43:1079Google Scholar
  103. 103.
    Lee S, Izumiya N, Suzuki A, Tamura S (1975) Tetrahedron Lett 883Google Scholar
  104. 104.
    Wang H-J, Gloer JB, Wicklow DT, Dowd PF (1995) Appl Environ Microbiol 61:4429Google Scholar
  105. 105.
    Kimbrell DA (1991) BioEssays 13:657CrossRefGoogle Scholar
  106. 106.
    Dixon B (1992) Bio/Technology 10:607CrossRefGoogle Scholar
  107. 107.
    Molan PC (1992) The Beekeepers Quarterly 25:24Google Scholar
  108. 108.
    Trimble JE, Veal DA, Beattie AJ (1992) J Appl Bacteriol 72:188Google Scholar
  109. 109.
    Janzen DH (1977) Amer Naturalist 111:691CrossRefGoogle Scholar
  110. 110.
    Kendrick B (1986) Pure Appl Chem 58:211CrossRefGoogle Scholar
  111. 111.
    Edgar JA, Frahn JL, Cokrum PA, Anderton N, Jago MV, Culvenor CCJ, Jones AJ, Murray K, Shaw KJ (1982) J Chem Soc Chem Commun 222Google Scholar
  112. 112.
    Jalal MAF, Hossain MB, van der Helm D, Sanders-Loehr J, Actis LA, Crosa JH (1989) J Am Chem Society 111:292CrossRefGoogle Scholar
  113. 113.
    Nissen-Meyer J, Nes IF (1997) Arch Microbiol 167:67CrossRefGoogle Scholar
  114. 114.
    Bevins CL, Zasloff M (1990) Annu Rev Biochem 59:395CrossRefGoogle Scholar
  115. 115.
    Anonymous (1993) Sci Watch 42(7 Feb):3Google Scholar
  116. 116.
    Glick BR (1995) CJM 41:109Google Scholar
  117. 117.
    Neilands JB (1984) Microbiol Sci 1:9Google Scholar
  118. 118.
    Zähner H, Drautz H, Weber W (1982) In: Bu’Lock JD, Nisbet LJ, Winstanley DJ (eds) Bioactive microbial products: search and discovery. Academic Press, London, p 51Google Scholar
  119. 119.
    Keller-Schierlein W, Prelog V (1961) Helv Chim Acta 44:1981CrossRefGoogle Scholar
  120. 120.
    Anke H (1977) JAntibiot 30:125Google Scholar
  121. 121.
    Payne SM, Finkelstein RA (1975) Infect Immun 12:1313Google Scholar
  122. 122.
    Kochan I (1977) In: Weinberg ED (ed) Microorganisms and minerals. Marcel Dekker, New York, p 251Google Scholar
  123. 123.
    Kanne R, Zähner H (1976) Z Naturforsch 31c: 115Google Scholar
  124. 124.
    Gianinazzi S, Gianinazzi-Pearson V (October, 1988) Chimica oggi p 56Google Scholar
  125. 125.
    Krywolap GN, Grand LF, Casida LE Jr (1964) Can J Microbiol 10:323Google Scholar
  126. 126.
    Marx DH (1969) Phytopathology 59:411Google Scholar
  127. 127.
    Teintze M, Hossain MB, Barnes CL, Leong J, van der Helm D (1981) Biochemistry 20:6446CrossRefGoogle Scholar
  128. 128.
    De Weger L, van Boxtel R, van der Burg B, Gruters RA, Geels FP, Schippers B, Lugtenburg B (1986) J Bacteriol 165:585Google Scholar
  129. 129.
    Fravel DR (1988) Ann Rev Phytopath 26:75Google Scholar
  130. 130.
    Gutterson N (1990) Crit Rev Biotech 10:69CrossRefGoogle Scholar
  131. 131.
    Keel C, Wirthner PH, Oberhansli TH, Voisard C,B utger D, Hass D, Défago G (1990) Symbiosis 9:327Google Scholar
  132. 132.
    Hamden H, Weller DM, Thomashow LS (1991) Appl Environ Microbiol 57:3270Google Scholar
  133. 133.
    Leong J (1986) Ann Rev Phytopath 24:187CrossRefGoogle Scholar
  134. 134.
    Loper JE (1988) Phytopathology 78:166CrossRefGoogle Scholar
  135. 135.
    Schippers B, Bakker AW, Bakker PAHM (1987) Ann Rev Phytopath 25:339CrossRefGoogle Scholar
  136. 136.
    O’Sullivan DJ, O’Gara F (1992) Microbiol Rev 56:662Google Scholar
  137. 137.
    Kloepper JW, Leong J, Teintze M, Schroth MN (1980) Nature 286:885CrossRefGoogle Scholar
  138. 138.
    O’Gara F, Treacy P, O’Sullivan D, O’Sullivan M, Higgins P (1986) In: Swinburne TR (ed) Iron siderophores and plant disease. Plenum, New York, p 331Google Scholar
  139. 139.
    Vanderbergh PA, Gonzalez CF, Wright AM, Kunka BS (1983) Appl Environ Microbiol 46:128Google Scholar
  140. 140.
    Bakker PAHM, Lamers JG, Bakker AW, Marugg JD, Weisbeek PJ, Schippers B (1986) Neth J Plant Pathol 92:249CrossRefGoogle Scholar
  141. 141.
    Thomashow LS, Weller DM, Bonsall RF, Pierson LS III (1990) Appl Environ Microbiol 56:908Google Scholar
  142. 142.
    Shanahan P, O’Sullivan DJ, Simpson P, Glennon JD, O’Gara F (1992) Appl Environ Microbiol 58:353Google Scholar
  143. 143.
    Haas D, Keel C, Laville J, Maurhofer M, Oberhansli T, Schnider U, Voisard C, Wuthrich B, Dérfago G (1991) In: Hennecke H, Verma DPS (eds) Advances of molecular genetics of plant-microbe interactions. Kluwer Academic Publishers, Dordrect, The Netherlands, p 450Google Scholar
  144. 144.
    Voisard C, Kell C, Haas D, Défago G (1989) EMBO J 8:351Google Scholar
  145. 145.
    Raaijmakers JM, Weller DM, Thomashow LS (1997) Appl Environ Microbiol 63:881Google Scholar
  146. 146.
    Pierson LS, Pierson EA 1996. FEMS Microbiol Lett 136:101CrossRefGoogle Scholar
  147. 147.
    Thomashow LS, Weller DM (1988) J Bacteriol 170:3499Google Scholar
  148. 148.
    Mazzola M, Cook RJ, Thomashow LS, Weller DM, Pierson III LS (1992) Appl Envir Microbiol 58:2616Google Scholar
  149. 149.
    Pierson LS, Thomashow LS (1992) Mol Plant-Microbe Interact 5:330Google Scholar
  150. 150.
    Vincent MN, Harrison LA, Brackin JM, Kovacevich PA, Mukerji P, Weller DM, Pierson EA (1991) Appl Environ Microbiol 57:2928Google Scholar
  151. 151.
    Gutterson N, Ziegle JS, Warren GJ, Layton TJ (1988) J Bacteriol 170:380Google Scholar
  152. 152.
    Gutterson N, Howie W, Suslow T (1990) In: Baker R, Dunn P (eds) New directions in biological control: alternatives for suppressing agricultural pests and diseases. Alan R. Liss, New York, p 749Google Scholar
  153. 153.
    Hill DS, Stein JI, Torkewitz NR, Morse AM, Howell CR, Pachlatko JP, Becker JO, Ligon JM (1994) Appl Environ Microbiol 60:78Google Scholar
  154. 154.
    Buysens S, Heungens K, Poppe J, Höfte M (1996) Appl Environ Microbiol 62:865Google Scholar
  155. 155.
    Gill PR Jr, Warren GJ (1988) J Bacteriol 170:163Google Scholar
  156. 156.
    Silo-Suh LA, Lethbridge BJ, Raffel SJ, He H, Clardy J, Handelsman J (1994) Appl Environ Microbiol 60:2023Google Scholar
  157. 157.
    Stabb EV, Jacobson LM, Handelsman J (1994) Appl Environ Microbiol 60:4404Google Scholar
  158. 158.
    Leifert C, Li H, Chidburee S, Hampson S, Workman S, Sigee D, Epton HAS, Harbour A (1995) J Appl Bacteriol 78:97Google Scholar
  159. 159.
    Rothrock CS, Gottlieb D (1984) Can J Microbiol 30:1440CrossRefGoogle Scholar
  160. 160.
    Eckwall EC, Schottel JL (1997) J Indust Microbiol Biotechnol 19:220CrossRefGoogle Scholar
  161. 161.
    Costacurta S, Vanderlyden J (1995) Crit Rev Microbiol 21:1CrossRefGoogle Scholar
  162. 162.
    Kimura Y, Mizuno T, Nakajima H, Hamasaki T (1992) Biosci Biotech Biochem 56:1664CrossRefGoogle Scholar
  163. 163.
    Yang X, Strobel G, Stierle A, Hess WM, Lee J, Clardy J (1994) Plant Sci 102:1CrossRefGoogle Scholar
  164. 164.
    Paul VJ, Frautschy S, Fenical W, Nealson KH (1981) J Chem Ecol 7:589CrossRefGoogle Scholar
  165. 165.
    Akhurst RJ (1982) J Gen Microbiol 128:3061Google Scholar
  166. 166.
    Richardson WH, Schmidt TM, Nealson K (1988) Appl Environ Microbiol 54:1602Google Scholar
  167. 167.
    Jigami Y, Harada H, Uemura H, Tanaka H, Ishikawa K, Nakasoto S, Kita H, Sugiura M (1986) Agric Biol Chem 50:1637Google Scholar
  168. 168.
    Fredenhagen A, Tamura SY, Kenney PTM, Komura H, Naya Y, Nakanishi K, Nishiyama K, Sugiura M, Kita H (1987) J Amer Chem Soc 109:4409CrossRefGoogle Scholar
  169. 169.
    Gil-Turnes MS, Hay ME, Fenical W (1989) Science 246:116CrossRefGoogle Scholar
  170. 170.
    Fenical W (1993) Chem Rev 93:1673CrossRefGoogle Scholar
  171. 171.
    Elyakov GB, Kuznetsova T, Mikhailov VV, Maltsev II, Voinov VG, Fedoreyev SA (1991) Experientia47:632CrossRefGoogle Scholar
  172. 172.
    Voinov VG, El’kin YN, Kuznetsova TA, Mal’tsev II, Mikhailov VV, Sasunkevich VA (1991) J Chromatog 586:360CrossRefGoogle Scholar
  173. 173.
    Gooday GW (1987) In: Bennett JW, Ciegler A (eds) Secondary metabolism and differentiation in fungi. Marcel Dekker, New York, p 239Google Scholar
  174. 174.
    Gooday GW (1994) In: Wessels JGH, Meinhardt F (eds) The mycota. I. Growth, differentiation and sexuality. Springer, Berlin Heidelberg New York, p 401Google Scholar
  175. 175.
    Wolf JC, Mirocha CJ (1977) Appl Environ Microbiol 33:546Google Scholar
  176. 176.
    Nutting WH, Rapoport H, Machlis L (1968) J Am Chem Soc 90:6434CrossRefGoogle Scholar
  177. 177.
    Barksdale AW, Morris TC, Seshadri R, Aranachalam T, Edwards JA, Sundeen J, Green JM (1974) J Gen Microbiol 82:295Google Scholar
  178. 178.
    Sakagami Y, Isogai A, Suzuki A, Tamura S, Tsuchiya E, Fukui S (1987) Agric Biol Chem 42:1301Google Scholar
  179. 179.
    Champe S, Rao P, Chang A (1987) J Gen Microbiol 133:1383Google Scholar
  180. 180.
    Kunesch G, Zagatti P, Pouvreau A, Cassini R (1987) Z Naturforsch 42c: 657Google Scholar
  181. 181.
    Sakurai S, Tamura S, Yanagishima N, Shimoda C (1977) Agric Biol Chem 41:395Google Scholar
  182. 182.
    Kamiya M, Sakurai A, Tamura S, Takahashi N, Abe K, Tsuchiya E, Fukui S (1978) Agric Biol Chem 42:1239Google Scholar
  183. 183.
    Suzuki A, Mori M, Sakagami Y, Isogai A, Fujino M, Kitada C, Craig RA, Clewell DB (1984) Science 226:849CrossRefGoogle Scholar
  184. 184.
    Havarstein LS, Coomaraswamy G, Morrison DA (1995) Proc Natl Acad Sci USA 92:11140CrossRefGoogle Scholar
  185. 185.
    Nisbet L, Porter N (1989) Symp Soc Gen Microbiol 44:309Google Scholar
  186. 186.
    Roth J, Leroith D, Collier ES, Watkinson A, Lesniak MA (1986) Ann NY Acad Sci 463:1CrossRefGoogle Scholar
  187. 187.
    Pazoutova S, Pokorny V, Rehacek Z (1977) Can J Microbiol 23:1182CrossRefGoogle Scholar
  188. 188.
    Sarkar N, Paulus H (1972) Nature New Biol 239:228Google Scholar
  189. 189.
    Ristow H, Schazschneider B, Kleinkauf H (1975) Biochim Biophys Acta 63:1085Google Scholar
  190. 190.
    Schazschneider B, Ristow H, Kleinkauf H (1974) Nature 294:757CrossRefGoogle Scholar
  191. 191.
    Ristow H, Pschorn W, Hansen J, Winkel U (1979) Nature 280:165CrossRefGoogle Scholar
  192. 192.
    Demain AL, Piret JM (1979) In: Luckner M, Shreiber K (eds) Regulation of secondary product and plant hormone metabolism. Pergamon, New York, p 183Google Scholar
  193. 193.
    Mukherjee PK, Paulus H (1977) Proc Natl Acad Sci USA 74:780CrossRefGoogle Scholar
  194. 194.
    Piret JM, Demain AL (1983) J Gen Microbiol 129:1309Google Scholar
  195. 195.
    Symons DC, Hodgson B (1982) J Bacteriol 151:580Google Scholar
  196. 196.
    Marahiel MA, Danders W, Krause M, Kleinkauf H (1979) Eur J Biochem 99:49CrossRefGoogle Scholar
  197. 197.
    Nandi S, Seddon B (1978) Biochem Soc Trans 6:409Google Scholar
  198. 198.
    Ristow H, Russo J, Stochaj E, Paulus H (1982) In: Kleinkauf H, von Dohren H (eds) Peptide antibiotics-biosynthesis and functions. Walter de Gruyter, Berlin, p 381Google Scholar
  199. 199.
    Piret JM, Demain AL (1982) Arch Microbiol 133:38CrossRefGoogle Scholar
  200. 200.
    Özcengiz G, Alaeddinoglu NG (1991) Curr Microbiol 23:61CrossRefGoogle Scholar
  201. 201.
    Basalp A, Özcengiz G, Alaeddinoglu NG (1992) Curr Microbiol 24:129CrossRefGoogle Scholar
  202. 202.
    Grossman AD, Losick R (1988) Proc Natl Acad Sci USA 85:4369CrossRefGoogle Scholar
  203. 203.
    Chou WG, Pogell BM (1981) Biochem Biophys Res Commun 100:344CrossRefGoogle Scholar
  204. 204.
    McCann PA, Pogell BM (1979) J Antibiot 32:673Google Scholar
  205. 205.
    Kondo S, Yasui K, Natsume M, Katayama M, Marumo S (1988) J Antibiot 41:1196Google Scholar
  206. 206.
    Chou WG, Pogell BM (1981) Antimicrob Agents Chemother 20:443Google Scholar
  207. 207.
    Natsume M, Yasui K, Kondo S, Marumo S (1991) Tetrahedron Lett 32:3087CrossRefGoogle Scholar
  208. 208.
    Khokhlov AS, Anisova LN, Tovarova II, Kleiner EM, Koralenko LV, Krasilnikova OI, Kornitskaja EY, Pliner SA (1973) Z Allg Mikrobiol 13:647CrossRefGoogle Scholar
  209. 209.
    Grafe U, Reinhardt G, Schade W, Eritt I, Fleck WF, Radics L (1983) Biotechnol Lett 5:591CrossRefGoogle Scholar
  210. 210.
    Kondo S, Marumo S (1984) Ann Mtg Agric Chem Soc Japan No. IV-8:288Google Scholar
  211. 211.
    Schuz TC, Zähner H (1993) FEMS Microbiol Lett 144:41Google Scholar
  212. 212.
    Andres N, Wolf H, Zähner H (1990) Z Naturforschung 45c: 851Google Scholar
  213. 213.
    Azuma M, Hori K, O-hashi Y, Yoshida M, Horinouchi S, Beppu T (1990) Agric Biol Chem 54:1447Google Scholar
  214. 214.
    Tanaka S, Wada K, Katayama M, Marumo S (1984) Agric Biol Chem 49:3189Google Scholar
  215. 215.
    Kawai G, Ikeda Y (1985) J Lipid Res 26:338Google Scholar
  216. 216.
    Marumo S, Nukina M, Kondo S, Tomiyama K (1982) Agric Bio Chem 46:2399Google Scholar
  217. 217.
    Kondo S, Katayama M, Marumo S (1986) J Antibiot 39:727Google Scholar
  218. 218.
    Taya Y, Yamada T, Nishimura S (1980) J Bacteriol 143:715Google Scholar
  219. 219.
    Dahlberg KR, Van Etten JL (1982) Annu Rev Phytopathol 20:281CrossRefGoogle Scholar
  220. 220.
    Tsurushima T, Ueno T, Fukami H, Tani T, Mayama A (1990) Abstract PS86-11, IUMS Congress, OsakaGoogle Scholar
  221. 221.
    Leite B, Nicholson RL (1992) Exp Mycol 16:76CrossRefGoogle Scholar
  222. 222.
    Eaton D, Ensign JC (1980) J Bacteriol 143:377Google Scholar
  223. 223.
    Petersen F, Zähner H, Metzger JW, Freund S, Hummel R-P (1993) J Antibiot 46:1126Google Scholar
  224. 224.
    Piret JM (1980) Abstr 6th Internat Ferm Symp. London, CanadaGoogle Scholar
  225. 225.
    Lazaridis I, Frangou-Lazaridis M, Maccuish FC, Nandi S, Seddon B (1980) FEMS Microbiol Lett 7:229CrossRefGoogle Scholar
  226. 226.
    Danders W, Marahiel MA (1981) FEMS Microbiol Lett 10:277CrossRefGoogle Scholar
  227. 227.
    Nandi S, Lazaridis I, Seddon B (1981) FEMS Microbiol Lett 10:71CrossRefGoogle Scholar
  228. 228.
    Lobareva GS, Zharikova GG, Mesyanzhinov VV (1977) Doklady Biol Sci (English translation) 236:418Google Scholar
  229. 229.
    Danders W, Marahiel MA, Krause M, Kosui N, Kato T, Izumiya N, Kleinkauf H (1982) Antimicrob Agents Chemother 22:785Google Scholar
  230. 230.
    Frangou-Lazaridis M, Seddon B (1985) J Gen Microbiol 131:437Google Scholar
  231. 231.
    Daher E, Rosenberg E, Demain AL (1985) J Bacteriol 161:47Google Scholar
  232. 232.
    Petras SF, Casida, LE Jr (1985) Appl Environ Microbiol 50:1496Google Scholar
  233. 233.
    Rosenberg E, Brown DR, Demain AL (1985) Arch Microbiol 142:51CrossRefGoogle Scholar
  234. 234.
    Vinter V, Slepecky RA (1965) J Bacteriol 90:803Google Scholar
  235. 235.
    Maheshwari R (1991) J Gen Microbiol 137:2103Google Scholar
  236. 236.
    Piret JM, Millet J, Demain AL (1977) Abstr Ann Mtg Amer Soc Microbiol, p 166Google Scholar
  237. 237.
    Kurotsu T, Marahiel MA, Muller KD, Kleinkauf H (1982) J Bacteriol 151:1466Google Scholar
  238. 238.
    Piret JM, Millet J, Demain AL (1983) Eur J Appl Microbiol Biotechnol 17:227CrossRefGoogle Scholar
  239. 239.
    Slapikoff S, Spitzer JL,V accaro D (1971) J Bacteriol 106:739Google Scholar
  240. 240.
    Marahiel MA, Danders W, Kraepelin G, Kleinkauf H (1982) In: Kleinkauf H, von Dohren H (eds) Peptide antibiotics-biosynthesis and functions. Walter de Gruyter, Berlin, p 389Google Scholar
  241. 241.
    Piret JM (1981) PhD Thesis, Massachusetts Institute of Technology, Cambridge, USAGoogle Scholar
  242. 242.
    Daher E, (1983) M.S. Thesis, Massachusetts Institute of Technology, Cambridge, USAGoogle Scholar
  243. 243.
    Bentzen G, Demain AL (1990) Curr Microbiol 20:165CrossRefGoogle Scholar
  244. 244.
    Murray T, Lazaridis I, Seddon B (1985) Lett Appl Microbiol 1:63CrossRefGoogle Scholar
  245. 245.
    Rines HW, French RC, Daasch LB (1976) J Agr Food Chem 22:96CrossRefGoogle Scholar
  246. 246.
    Charlang G, Horowitz RM, Lowy PH, Ng B, Poling SM, Horowitz NH (1982) J Bacteriol 150:785Google Scholar
  247. 247.
    Horowitz NH, Charlang G, Horn G, Williams NP (1976) J Bacteriol 127:135Google Scholar
  248. 248.
    Matzanke BF, Bill E, Trautwein AX, Winkelmann G (1987) J Bacteriol 169:5873Google Scholar
  249. 249.
    Kay RR (1982) Proc Natl Acad Sci USA 79:3228CrossRefGoogle Scholar
  250. 250.
    Burger SR, Bennett JW (1985) Appl Environ Microbiol 50:487Google Scholar
  251. 251.
    Schroeder WA, Johnson EA (1995) J Biol Chem 270:18374CrossRefGoogle Scholar

Copyright information

© Springer-Verlag Berlin Heidelberg 2000

Authors and Affiliations

  • Arnold L. Demain
    • 1
  • Aiqi Fang
    • 1
  1. 1.Fermentation Microbiology Laboratory, Department of BiologyMassachusetts Institute of TechnologyCambridgeUSA

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