Ergot alkaloids: Structure diversity, biosynthetic gene clusters and functional proof of biosynthetic genes

Natural Product Reports

Volumn 28, Issue 3, 2011, Pages 496-510

  Wallwey, Christiane ^a   Li, Shu Ming ^a  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ERGOT ALKALOID; MYCOTOXIN;

ASCOMYCETES; BIOSYNTHESIS; CHEMICAL STRUCTURE; CHEMISTRY; FUNGAL GENE; GENETICS; MULTIGENE FAMILY; REVIEW;

ASCOMYCOTA; ERGOT ALKALOIDS; GENES, FUNGAL; MOLECULAR STRUCTURE; MULTIGENE FAMILY; MYCOTOXINS;

ASCOMYCOTA; ASPERGILLUS; CLAVICEPS; EMBRYOPHYTA; FUNGI; PENICILLIUM;

EID: 79952014752     PISSN: 02650568     EISSN: 14604752     Source Type: Journal    
DOI: 10.1039/c0np00060d     Document Type: Review

References (148)

1. C. L. Schardl, D. G. Panaccione and P. Tudzynski, Alkaloids: Chem. Biol., 2006, 63, 45-86.
2. M. Flieger, M. Wurst and R. Shelby, Folia Microbiol., 1997, 42, 3-30.
3. D. Gröger and H. G. Floss, Alkaloids: Chem. Biol., 1998, 50, 171-218.
4. T. Haarmann, et al., Mol. Plant Pathol., 2009, 10, 563-577.
5. A. N. de Groot, et al., Drugs, 1998, 56, 523-535.
6. M. R. Lee, J. R. Coll. Physicians Edinbugh, 2009, 39, 179-184.
7. M. R. Lee, J. R. Coll. Physicians Edinburgh, 2009, 39, 365-369.
8. K. Pedrosa and K. Grießler, Feed Intern., September-October 2010, pp. 28-30.
9. C. L. Schardl, A. Leuchtmann and M. J. Spiering, Annu. Rev. Plant Biol., 2004, 55, 315-340.
10. D. G. Panaccione, et al., Proc. Natl. Acad. Sci. U. S. A., 2001, 98, 12820-12825.
11. E. Leistner and U. Steiner, 'Fungal Origin of Ergoline Alkaloids Present in Dicotyledonous Plants (Convolvulaceae)', in The Mycota XV: Physiology and Genetics, Springer-Verlag, Berlin/Heidelberg, 2009, pp. 197-208.
12. H. G. Floss, Tetrahedron, 1976, 32, 873-912.
13. H. G. Floss, et al., J. Am. Chem. Soc., 1974, 96, 1898-1909.
14. R. M. Williams, E. M. Stocking and J. F. Sanz-Cervera, Top. Curr. Chem., 2000, 209, 97-173.
15. P. Tudzynski, et al., Mol. Gen. Genet., 1999, 261, 133-141.
16. H. F. Tsai, et al., Biochem. Biophys. Res. Commun., 1995, 216, 119-125.
17. I. A. Unsöld and S.-M. Li, Microbiology, 2005, 151, 1499-1505.
18. C. M. Coyle, et al., Mycologia, 2007, 99, 804-811.
19. B. G. Katzug, 'Histamine, Serotonin and the Ergot Alkaloids', in Basic and Clinical Pharmacology, ed. B. G. Katzung, S. B. Masters, and A. J. Trevor, McGraw-Hill Medical, 2009, pp. 271-292.
20. A. Sinz, Pharm. Unserer Zeit, 2008, 37, 306-309.
21. R. J. Cole and M. A. Schweikert, 'Indole Alkaloids', in Handbook of secondary fungal metabolites, Elsevier Science, 2003, pp. 1-143.
22. H. Pertz, Planta Med., 1996, 62, 387-392.
23. H. M. Ge, et al., J. Nat. Prod., 2009, 72, 753-755.
24. I. A. Unsöld and S.-M. Li, ChemBioChem, 2006, 7, 158-164.
25. J. C. Frisvad, et al., Med. Mycol., 2008, 1-19.
26. S. Ohmomo, M. Kaneko and P. Atthasampunna, MIRCEN J. Appl. Microbiol. Biotechnol., 1989, 5, 5-13.
27. K. Kawai, et al., Mycotoxins, 1992, 36, 19-24.
28. R. J. Cole, et al., Ann. Nutr. Aliment., 1977, 31, 685-691.
29. Y. Zhao, et al., J. Pharm. Pharmacol., 2004, 56, 775-782.
30. T. Möller, K. Åkerstrand and T. Massoud, Nat. Toxins., 1997, 5, 86-89.
31. M. O'Brien, et al., J. Agric. Food Chem., 2006, 54, 9268-9276.
32. R. J. Cole, et al., J. Agric. Food Chem., 1983, 31, 655-657.
33. H. Y. Ma, et al., Planta Med., 2006, 72, 387-392.
34. X.-F. Wu, et al., Int. Immunopharmacol., 2005, 5, 1543-1553.
35. P. W. van Dongen and A. N. de Groot, Eur. J. Obstet. Gynecol. Reprod. Biol., 1995, 60, 109-116.
36. C. De Costa, Lancet, 2002, 359, 1768-1770.
37. P. V. Rajan and D. A. Wing, Clin. Obst. Gyn., 2010, 53, 165-181.
38. M. R. Lee, J. R. Coll. Physicians Edinburgh, 2010, 40, 77-80.
39. A. Hofmann, LSD - My Problem Child, McGraw-Hill, New York, 1980.
40. S. Uhlig and D. Petersen, Toxicon, 2008, 52, 175-185.
41. T. Correia, et al., Chem. Biol., 2003, 10, 1281-1292.
42. T. Haarmann, N. Lorenz and P. Tudzynski, Fungal. Genet. Biol, 2008, 45, 35-44.
43. C. E. Robertson, D. F. Black and J. W. Swanson, Semin. Neurol., 2010, 30, 201-211.
44. R. Halker, B. Vargas and D. W. Dodick, Semin. Neurol., 2010, 30, 175-185.
45. J. R. Saper and S. Silberstein, Headache, 2006, 46(Suppl. 4), S171-S181.
46. B. V. Lovell and M. J. Marmura, Curr. Opin. Neurol., 2010, 23, 254-258.
47. G. Jourdan, et al., Fundam. Clin. Pharmacol., 2007, 21, 45-53.
48. D. J. Fleetwood, et al., Appl. Environ. Microbiol., 2007, 73, 2571-2579.
49. P. L. Schiff, Am. J. Pharm. Educ., 2006, 70, 1-10.
50. I. Setnikar, et al., Arzneimittelforschung., 2001, 51, 2-6.
51. W. Cabri, et al., Org. Process Res. Dev., 2006, 10, 198-202.
52. U. Bonuccelli, P. Del Dotto and O. Rascol, Parkinsonism Relat. Disord., 2009, 15S, S44-S53.
53. P. Martinez-Martin and M. M. Kurtis, Parkinsonism Relat. Disord., 2009, 15(Suppl. 4), S58-S64.
54. M. P. Curran and C. M. Perry, Drugs, 2004, 64, 2125-2141.
55. J. M. Cassady, et al., J. Med. Chem., 1974, 17, 300-307.
56. P. Chanson, et al., Ann. Endocrinol. (Paris), 2007, 68, 113-117.
57. S. Motazedian, et al., Indian J Med. Res., 2010, 131, 670-674.
58. A. Colao, et al., Nat. Clin. Pract. Endocrinol. Metab., 2006, 2, 200-210.
59. J. C. Frisvad, et al., Stud. Mycol., 2004, 49, 201-241.
60. T. Furuta, M. Koike and M. Abe, Agric. Biol. Chem., 1982, 46, 1921-1922.
61. J. W. Dorner, et al., Appl. Environ. Microbiol., 1980, 40, 685-687.
62. R. J. Cole, et al., Tetrahedron Lett., 1976, 17, 3849-3852.
63. S. Yamatodani, et al., Agric. Biol. Chem., 1970, 34, 485-487.
64. H. Tscherter and H. Hauth, Helv. Chim. Acta, 1974, 57, 113-121.
65. G. S. King, et al., J. Chem. Soc., Perkin Trans. 1, 1977, 2099-2103.
66. J. E. Robbers and H. G. Floss, Tetrahedron Lett., 1969, 10, 1857-1858.
67. A. G. Kozlovskii, et al., Dokl. Akad. Nauk SSSR, 1981, 260, 230-233.
68. J. C. Frisvad, et al., Med. Mycol., 2009, 47, S53-S71.
69. V. P. Zhelifonova, et al., Microbiology (Moscow), 2009, 78, 350-354.
70. N. G. Vinokurova, et al., Microbiology (Moscow), 2003, 72, 149-151.
71. K. K. Janardhanan, A. Sattar and A. Husain, Can. J. Microbiol., 1984, 30, 247-250.
72. R. J. Cole, et al., J. Agric. Food Chem., 1977, 25, 826-830.
73. D. G. Panaccione and C. M. Coyle, Appl. Environ. Microbiol., 2005, 71, 3106-3111.
74. J. F. Spilsbury and S. Wilkinson, J. Chem. Soc., 1961, 2085-2091.
75. N. G. Vinokurova, et al., Appl. Biochem. Microbiol., 1991, 27, 644-648.
76. N. G. Vinokurova, L. V. Boichenko and M. U. Arinbasarov, Appl. Biochem. Microbiol., 2003, 39, 403-406.
77. L. V. Boichenko, et al., Appl. Biochem. Microbiol., 2003, 39, 294-299.
78. G. T. Banks, P. G. Mantle and C. A. Szczyrbak, J. Gen. Microbiol., 1974, 82(Pt. 2), 345-361.
79. S. Pažoutová, et al., J. Nat. Prod., 1981, 44, 225-235.
80. B. Schumann, et al., Planta Med., 1982, 45, 11-14.
81. V. Kren, et al., FEMS Microbiol. Lett., 1986, 37, 31-34.
82. N. Lorenz, et al., Phytochemistry, 2009, 70, 1822-1932.
83. I. Ortel and U. Keller, J. Biol. Chem., 2009, 284, 6650-6660.
84. C. L. Schardl, B. Scott, S. Florea and D. Zhang, 'Epichloë Endophytes: Clavicipitaceous Symbionts of Grasses', in The Mycota V: Plant Relationships, Springer-Verlag, Berlin/Heidelberg, 2009, pp. 275-306.
85. S. Kucht, et al., Planta, 2004, 219, 619-625.
86. A. Markert, et al., Plant Physiol., 2008, 147, 296-305.
87. M. A. Ahimsa-Müller, et al., J. Nat. Prod., 2007, 70, 1955-1960.
88. C. L. Schardl, Fungal. Genet. Biol., 2001, 33, 69-82.
89. A. A. Bacetty, et al., Phytopathology, 2009, 99, 1336-1345.
90. S. H. Faeth, C. J. Hayes and D. R. Gardner, Plant-Microbe Interact., 2010, DOI: 10.1007/s00248-010-9643-4.
91. S. B. Hassam and H. G. Floss, J. Nat. Prod., 1981, 44, 756-758.
92. H. G. Floss and J. A. Anderson, 'Biosynthesis of Ergot Toxins', in The biosynthesis of mycotoxins. A study in secondary metabolism, ed. S. S. Pieter, 1980, pp. 17-67.
93. D. Hoffmeister and N. P. Keller, Nat. Prod. Rep., 2007, 24, 393-416.
94. M. Luzhetska, J. Härle and A. Bechthold, Fortschr. Chem Org. Naturst., 2010, 93, 211-237.
95. A. Osbourn, Trends Genet., 2010, 26, 449-457.
96. T. Haarmann, et al., Phytochemistry, 2005, 66, 1312-1320.
97. N. Lorenz, et al., Appl. Environ. Microbiol., 2007, 73, 7185-7191.
98. C. T. Walsh and M. A. Fischbach, J. Am. Chem. Soc., 2010, 132, 2469-2493.
99. D. Stack, C. Neville and S. Doyle, Microbiology, 2007, 153, 1297-1306.
100. H. von Döhren, Adv. Biochem. Eng. Biotechnol., 2004, 88, 217-264.
101. L. Du and L. Lou, Nat. Prod. Rep., 2010, 27, 255-278.
102. I. A. Uns̈old, Dissertation Universität Tübingen, 2006.
103. M. G. Jones, Microbiology, 2007, 153, 1-6.
104. N. P. Keller, G. Turner and J. W. Bennett, Nat. Rev. Microbiol., 2005, 3, 937-947.
105. C. Corre and G. L. Challis, Nat. Prod. Rep., 2009, 26, 977-986.
106. W. C. Nierman, et al., Nature, 2005, 438, 1151-1156.
107. S.-M. Li, Phytochemistry, 2009, 70, 1746-1757.
108. N. Steffan, et al., Curr. Med. Chem., 2009, 16, 218-231.
109. C. M. Coyle and D. G. Panaccione, Appl. Environ. Microbiol., 2005, 71, 3112-3118.
110. S.-M. Li, Nat. Prod. Rep., 2010, 27, 57-78.
111. C. Wallwey, et al., Org. Biomol. Chem., 2010, 8, 3500-3508.
112. J. Wang, et al., Fungal Genet. Biol., 2004, 41, 189-198.
113. N. Steffan, I. A. Unsöld and S.-M. Li, ChemBioChem, 2007, 8, 1298-1307.
114. N. Steffan and S.-M. Li, Arch. Microbiol., 2009, 191, 461-466.
115. U. Metzger, et al., Proc. Natl. Acad. Sci. U. S. A., 2009, 106, 14309-14314.
116. Y. Ding, R. M. Williams and D. H. Sherman, J. Biol. Chem., 2008, 283, 16068-16076.
117. A. Kremer and S.-M. Li, Microbiology, 2010, 156, 278-286.
118. P. H. Liang, T. P. Ko and A. H. Wang, Eur. J. Biochem., 2002, 269, 3339-3354.
119. K. Yazaki, K. Sasaki and Y. Tsurumaru, Phytochemistry, 2009, 70, 1739-1745.
120. Y. Ding, et al., J. Am. Chem. Soc., 2010, 132, 12733-12740.
121. W.-B. Yin, J. Cheng and S.-M. Li, Org. Biomol. Chem., 2009, 7, 2202-2207.
122. S.-M. Li, Appl. Microbiol. Biotechnol., 2009, 84, 631-639.
123. W.-B. Yin, et al., Org. Biomol. Chem., 2010, 8, 1133-1141.
124. W.-B. Yin, et al., Org. Biomol. Chem., 2010, 8, 2430-2438.
125. T. Kuzuyama, J. P. Noel and S. B. Richard, Nature, 2005, 435, 983-987.
126. Y. Haagen, et al., FEBS Lett., 2007, 581, 2889-2893.
127. F. Pojer, et al., Proc. Natl. Acad. Sci. U. S. A., 2003, 100, 2316-2321.
128. O. Saleh, et al., J. Biol. Chem., 2009, 284, 14439-14447.
129. S. Keller, et al., Acta Crystallogr., Sect. F: Struct. Biol. Cryst. Commun., 2006, 62, 1153-1155.
130. E. Stec, et al., ChemBioChem, 2008, 9, 2055-2058.
131. L. Y. Luk and M. E. Tanner, J. Am. Chem. Soc., 2009, 131, 13932-13933.
132. M. Liu, D. G. Panaccione and C. L. Schardl, Evol. Bioinform., 2009, 5, 15-30.
133. O. Rigbers and S.-M. Li, J. Biol. Chem., 2008, 283, 26859-26868.
134. R. M. Kagan and S. Clarke, Arch. Biochem. Biophys., 1994, 310, 417-427.
135. P. Z. Kozbial and A. R. Mushegian, BMC Struct. Biol., 2005, 5, 19-44.
136. M. Abe, et al., Agric. Biol. Chem., 1969, 33, 469-471.
137. N. Lorenz, et al., Appl. Environ. Microbiol., 2010, 76, 1822-1830.
138. C. Wallwey, M. Matuschek and S.-M. Li, Arch. Microbiol., 2010, 192, 127-134.
139. C. M. Coyle, et al., Appl. Environ. Microbiol., 2010, 76, 3898-3903.
140. J. Z. Cheng, et al., J. Am. Chem. Soc., 2010, 132, 12835-12837.
141. J. Z. Cheng, et al., J. Am. Chem. Soc., 2010, 132, 1776-1777.
142. H. Plieninger, et al., Justus Liebigs Ann. Chem., 1978, 1978, 813-817.
143. S.-M. Li and I. A. Unsöld, Planta Med., 2006, 72, 1117-1120.
144. X. Liu, et al., ChemBioChem, 2009, 10, 2325-2328.
145. T. Haarmann, et al., ChemBioChem, 2006, 7, 645-652.
146. B. Walzel, B. Riederer and U. Keller, Chem. Biol., 1997, 4, 223-230.
147. F. R. Quigley and H. G. Floss, J. Org. Chem., 1981, 46, 464-466.
148. D. G. Panaccione, et al., J. Agric. Food Chem., 2003, 51, 6429-6437.