Circular proteins from plants and fungi

Journal of Biological Chemistry

Volumn 287, Issue 32, 2012, Pages 27001-27006

  Göransson, Ulf ^a   Burman, Robert ^a   Gunasekera, Sunithi ^a   Strömstedt, Adam A ^a   Rosengren, K Johan ^a,b  

^a UPPSALA UNIVERSITY   (Sweden)

^b UNIVERSITY OF QUEENSLAND   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

CIRCULAR PROTEINS; CROP PROTECTION; CYCLOTIDES; MECHANISM OF ACTION; NATURAL PRODUCTS; PROTEIN FAMILY; RATIONAL POINTS; RIBOSOMAL SYNTHESIS; STRUCTURAL CONCEPT; TRYPSIN INHIBITOR;

FUNGI; POLYPEPTIDES;

PROTEINS;

AMANITIN; CIRCULAR PROTEIN; CIRCULAR SUNFLOWER TRYPSIN INHIBITOR; CYCLOTIDE; PHALLOTOXIN; POLYPEPTIDE; RNA POLYMERASE II; TRYPSIN INHIBITOR; UNCLASSIFIED DRUG;

AMANITA; ANTIMICROBIAL ACTIVITY; BETA SHEET; CRYSTAL STRUCTURE; FUNGUS; HOST RESISTANCE; HYDROGEN BOND; INSECTICIDAL ACTIVITY; LD 50; NONHUMAN; OLDENLANDIA; PLANT; PRIORITY JOURNAL; PROTEIN CROSS LINKING; PROTEIN EXPRESSION; PROTEIN MOTIF; PROTEIN PROCESSING; PROTEIN STRUCTURE; RIBOSOME; SHORT SURVEY;

AMINO ACID SEQUENCE; FUNGAL PROTEINS; MOLECULAR SEQUENCE DATA; PEPTIDES, CYCLIC; PLANT PROTEINS; SEQUENCE HOMOLOGY, AMINO ACID;

AMANITA; FUNGI; HELIANTHUS;

EID: 84864551115     PISSN: 00219258     EISSN: 1083351X     Source Type: Journal    
DOI: 10.1074/jbc.R111.300129     Document Type: Short Survey

References (50)

1. Vetter, J. (1998) Toxins of Amanita phalloides. Toxicon 36, 13-24
2. Walton, J. D., Hallen-Adams, H. E., and Luo, H. (2010) Ribosomal biosynthesis of the cyclic peptide toxins of Amanita mushrooms. Biopolymers 94, 659-664
3. Hallen, H. E., Luo, H., Scott-Craig, J. S., and Walton, J. D. (2007) Gene family encoding the major toxins of lethal Amanita mushrooms. Proc. Natl. Acad. Sci. U.S.A. 104, 19097-19101
4. Luo, H., Hallen-Adams, H. E., Scott-Craig, J. S., and Walton, J. D. (2010) Colocalization of amanitin and a candidate toxin-processing prolyl oligopeptidase in Amanita basidiocarps. Eukaryot. Cell 9, 1891-1900
5. Kaplan, C. D., Larsson, K. M., and Kornberg, R. D. (2008) The RNA polymerase II trigger loop functions in substrate selection and is directly targeted by α-amanitin. Mol. Cell 30, 547-556 (Pubitemid 351755064)
6. Auinger, S., and Small, J. V. (2008) Correlated light and electron microscopy of the cytoskeleton. Methods Cell Biol. 88, 257-272
7. Luckett, S., Garcia, R. S., Barker, J. J., Konarev, A. V., Shewry, P. R., Clarke, A. R., and Brady, R. L. (1999) High resolution structure of a potent cyclic proteinase inhibitor from sunflower seeds. J. Mol. Biol. 290, 525-533 (Pubitemid 29324836)
8. 1HNMRof the novel cyclic trypsin inhibitor SFTI-1 from sunflower seeds and an acyclic permutant. J. Mol. Biol. 311, 579-591
9. Korsinczky, M. L., Clark, R. J., and Craik, D. J. (2005) Disulfide bond mutagenesis and the structure and function of the head-to-tail macrocyclic trypsin inhibitor SFTI-1. Biochemistry 44, 1145-1153 (Pubitemid 40208994)
10. Daly, N. L., Chen, Y. K., Foley, F. M., Bansal, P. S., Bharathi, R., Clark, R. J., Sommerhoff, C. P., and Craik, D. J. (2006) The absolute structural requirement for a proline in the P3′-position of Bowman-Birk protease inhibitors is surmounted in the minimized SFTI-1 scaffold. J. Biol. Chem. 281, 23668-23675 (Pubitemid 44274142)
11. Mylne, J. S., Colgrave, M. L., Daly, N. L., Chanson, A. H., Elliott, A. G., McCallum, E. J., Jones, A., and Craik, D. J. (2011) Albumins and their processing machinery are hijacked for cyclic peptides in sunflower. Nat. Chem. Biol. 7, 257-259
12. Craik, D. J., Daly, N. L., Bond, T., and Waine, C. (1999) Plant cyclotides: a unique family of cyclic and knotted proteins that defines the cyclic cystine knot structural motif. J. Mol. Biol. 294, 1327-1336 (Pubitemid 30008803)
13. Gruber, C. W., Elliott, A. G., Ireland, D. C., Delprete, P. G., Dessein, S., Göransson, U., Trabi, M., Wang, C. K., Kinghorn, A. B., Robbrecht, E., and Craik, D. J. (2008) Distribution and evolution of circular miniproteins in flowering plants. Plant Cell 20, 2471-2483 (Pubitemid 352844612)
14. Colgrave, M. L., and Craik, D. J. (2004) Thermal, chemical, and enzymatic stability of the cyclotide kalata B1: the importance of the cyclic cystine knot. Biochemistry 43, 5965-5975 (Pubitemid 38669464)
15. Rosengren, K. J., Daly, N. L., Plan, M. R., Waine, C., and Craik, D. J. (2003) Twists, knots, and rings in proteins. Structural definition of the cyclotide framework. J. Biol. Chem. 278, 8606-8616 (Pubitemid 36800615)
16. Wang, C. K., Hu, S. H., Martin, J. L., Sjögren, T., Hajdu, J., Bohlin, L., Claeson, P., Göransson, U., Rosengren, K. J., Tang, J., Tan, N. H., and Craik, D. J. (2009) Combined x-ray andNMRanalysis of the stability of the cyclotide cystine knot fold that underpins its insecticidal activity and potential use as a drug scaffold. J. Biol. Chem. 284, 10672-10683
17. Kaas, Q., and Craik, D. J. (2010) Analysis and classification of circular proteins in CyBase. Biopolymers 94, 584-591
18. Göransson, U., Herrmann, A., Burman, R., Haugaard-Jönsson, L. M., and Rosengren, K. J. (2009) The conserved Glu in the cyclotide cycloviolacin O2 has a key structural role. ChemBioChem 10, 2354-2360
19. Herrmann, A., Svangård, E., Claeson, P., Gullbo, J., Bohlin, L., and Göransson, U. (2006) Key role of glutamic acid for the cytotoxic activity of the cyclotide cycloviolacin O2. Cell. Mol. Life Sci. 63, 235-245 (Pubitemid 43100292)
20. Simonsen, S. M., Sando, L., Rosengren, K. J., Wang, C. K., Colgrave, M. L., Daly, N. L., and Craik, D. J. (2008) Alanine scanning mutagenesis of the prototypic cyclotide reveals a cluster of residues essential for bioactivity. J. Biol. Chem. 283, 9805-9813
21. Burman, R., Gruber, C. W., Rizzardi, K., Herrmann, A., Craik, D. J., Gupta, M. P., and Göransson, U. (2010) Cyclotide proteins and precursors from the genus Gloeospermum: filling a blank spot in the cyclotide map of Violaceae. Phytochemistry 71, 13-20
22. Poth, A. G., Colgrave, M. L., Philip, R., Kerenga, B., Daly, N. L., Anderson, M. A., and Craik, D. J. (2011) Discovery of cyclotides in the Fabaceae plant family provides new insights into the cyclization, evolution, and distribution of circular proteins. ACS Chem. Biol. 6, 345-355
23. Hernandez, J. F., Gagnon, J., Chiche, L., Nguyen, T. M., Andrieu, J. P., Heitz, A., Trinh Hong, T., Pham, T. T., and Le Nguyen, D. (2000) Squash trypsin inhibitors from Momordica cochinchinensis exhibit an atypical macrocyclic structure. Biochemistry 39, 5722-5730 (Pubitemid 30307960)
24. Craik, D. J. (2010) Discovery and applications of the plant cyclotides. Toxicon 56, 1092-1102
25. Pränting, M., Lööv, C., Burman, R., Göransson, U., and Andersson, D. I. (2010) The cyclotide cycloviolacin O2 from Viola odorata has potent bactericidal activity against Gram-negative bacteria. J. Antimicrob. Chemother. 65, 1964-1971
26. Wong, C. T., Taichi, M., Nishio, H., Nishiuchi, Y., and Tam, J. P. (2011) Optimal oxidative folding of the novel antimicrobial cyclotide from Hedyotis biflora requires high alcohol concentrations. Biochemistry 50, 7275-7283
27. Jennings, C., West, J., Waine, C., Craik, D., and Anderson, M. (2001) Biosynthesis and insecticidal properties of plant cyclotides: the cyclic knotted proteins from Oldenlandia affinis. Proc. Natl. Acad. Sci. U.S.A. 98, 10614-10619 (Pubitemid 32878669)
28. Mylne, J. S., Wang, C. K., van der Weerden, N. L., and Craik, D. J. (2010) Cyclotides are a component of the innate defense of Oldenlandia affinis. Biopolymers 94, 635-646
29. Shenkarev, Z. O., Nadezhdin, K. D., Sobol, V. A., Sobol, A. G., Skjeldal, L., and Arseniev, A. S. (2006) Conformation and mode of membrane interaction in cyclotides. Spatial structure of kalata B1 bound to a dodecylphosphocholine micelle. FEBS J. 273, 2658-2672
30. Svangård, E., Burman, R., Gunasekera, S., Lövborg, H., Gullbo, J., and Göransson, U. (2007) Mechanism of action of cytotoxic cyclotides: cycloviolacin O2 disrupts lipid membranes. J. Nat. Prod. 70, 643-647
31. Henriques, S. T., Huang, Y. H., Rosengren, K. J., Franquelim, H. G., Carvalho, F. A., Johnson, A., Sonza, S., Tachedjian, G., Castanho, M. A., Daly, N. L., and Craik, D. J. (2011) Decoding the membrane activity of the cyclotide kalata B1: the importance of phosphatidylethanolamine phospholipids and lipid organization in hemolytic and anti-HIV activities. J. Biol. Chem. 286, 24231-24241
32. Burman, R., Strömstedt, A. A., Malmsten, M., and Göransson, U. (2011) Cyclotide-membrane interactions: defining factors of membrane binding, depletion, and disruption. Biochim. Biophys. Acta 1808, 2665-2673
33. Huang, Y. H., Colgrave, M. L., Clark, R. J., Kotze, A. C., and Craik, D. J. (2010) Lysine scanning mutagenesis reveals an amendable face of the cyclotide kalata B1 for the optimization of nematocidal activity. J. Biol. Chem. 285, 10797-10805
34. Ireland, D. C., Clark, R. J., Daly, N. L., and Craik, D. J. (2010) Isolation, sequencing, and structure-activity relationships of cyclotides. J. Nat. Prod. 73, 1610-1622
35. Huang, Y. H., Colgrave, M. L., Daly, N. L., Keleshian, A., Martinac, B., and Craik, D. J. (2009) The biological activity of the prototypic cyclotide kalata b1 is modulated by the formation of multimeric pores. J. Biol. Chem. 284, 20699-20707
36. Ovesen, R. G., Brandt, K. K., Göransson, U., Nielsen, J., Hansen, H. C., and Cedergreen, N. (2011) Biomedicine in the environment: cyclotides constitute potent natural toxins in plants and soil bacteria. Environ. Toxicol. Chem. 30, 1190-1196
37. Trabi, M., Svangård, E., Herrmann, A., Göransson, U., Claeson, P., Craik, D. J., and Bohlin, L. (2004) Variations in cyclotide expression in Viola species. J. Nat. Prod. 67, 806-810 (Pubitemid 38702736)
38. Craik, D. J. (2009) Circling the enemy: cyclic proteins in plant defense. Trends Plant Sci. 14, 328-335
39. Colgrave, M. L., Korsinczky, M. J., Clark, R. J., Foley, F., and Craik, D. J. (2010) Sunflower trypsin inhibitor-1, proteolytic studies on a trypsin inhibitor peptide and its analogs. Biopolymers 94, 665-672
40. Swedberg, J. E., Nigon, L. V., Reid, J. C., de Veer, S. J., Walpole, C. M., Stephens, C. R., Walsh, T. P., Takayama, T. K., Hooper, J. D., Clements, J. A., Buckle, A. M., and Harris, J. M. (2009) Substrate-guided design of a potent and selective kallikrein-related peptidase inhibitor for kallikrein-4. Chem. Biol. 16, 633-643
41. Craik, D. J., and Conibear, A. C. (2011) The chemistry of cyclotides. J. Org. Chem. 76, 4805-4817
42. Gunasekera, S., Foley, F. M., Clark, R. J., Sando, L., Fabri, L. J., Craik, D. J., and Daly, N. L. (2008) Engineering stabilized vascular endothelial growth factor-A antagonists: synthesis, structural characterization, and bioactivity of grafted analogs of cyclotides. J. Med. Chem. 51, 7697-7704
43. Thongyoo, P., Roqué-Rosell, N., Leatherbarrow, R. J., and Tate, E. W. (2008) Chemical and biomimetic total syntheses of natural and engineered MCoTI cyclotides. Org. Biomol. Chem. 6, 1462-1470 (Pubitemid 351469865)
44. Austin, J., Wang, W., Puttamadappa, S., Shekhtman, A., and Camarero, J. A. (2009) Biosynthesis and biological screening of a genetically encoded library based on the cyclotide MCoTI-I. ChemBioChem 10, 2663-2670
45. Clark, R. J., Jensen, J., Nevin, S. T., Callaghan, B. P., Adams, D. J., and Craik, D. J. (2010) The engineering of an orally active conotoxin for the treatment of neuropathic pain. Angew. Chem. Int. Ed. Engl. 49, 6545-6548
46. Gran, L., Sandberg, F., and Sletten, K. (2000) Oldenlandia affinis (R&S) DC. A plant containing uteroactive peptides used in African traditional medicine. J. Ethnopharmacol. 70, 197-203 (Pubitemid 30317360)
47. Qin, Q., McCallum, E. J., Kaas, Q., Suda, J., Saska, I., Craik, D. J., and Mylne, J. S. (2010) Identification of candidates for cyclotide biosynthesis and cyclization by expressed sequence tag analysis of Oldenlandia affinis. BMC Genomics 11, 111
48. Mulvenna, J. P., Mylne, J. S., Bharathi, R., Burton, R. A., Shirley, N. J., Fincher, G. B., Anderson, M. A., and Craik, D. J. (2006) Discovery of cyclotide-like protein sequences in graminaceous crop plants: ancestral precursors of circular proteins? Plant Cell 18, 2134-2144 (Pubitemid 44484715)
49. Velásquez, J. E., and van der Donk, W. A. (2011) Genome mining for ribosomally synthesized natural products. Curr. Opin. Chem. Biol. 15, 11-21
50. Mohimani, H., Liu, W. T., Mylne, J. S., Poth, A. G., Colgrave, M. L., Tran, D., Selsted, M. E., Dorrestein, P. C., and Pevzner, P. A. (2011) Cycloquest: identification of cyclopeptides via database search of their mass spectra against genome databases. J. Proteome Res. 10, 4505-4512