Isolation and characterization of cytotoxic cyclotides from Viola philippica

Peptides

Volumn 32, Issue 8, 2011, Pages 1719-1723

  He, Wenjun ^a,c   Chan, Lai Yue ^b   Zeng, Guangzhi ^a   Daly, Norelle L ^b   Craik, David J ^b   Tan, Ninghua ^a  

^a KUNMING INSTITUTE OF BOTANY   (China)

^b UNIVERSITY OF QUEENSLAND   (Australia)

^c UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

Cyclic peptides; Cyclotides; Cytotoxic activity; Viola philippica; Violaceae; Viphi A H

Indexed keywords

CYCLOTIDE;

AMINO ACID SEQUENCE; ARTICLE; CANCER CELL CULTURE; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG ISOLATION; ENZYME DEGRADATION; FEMALE; HELA CELL; HUMAN; HUMAN CELL; MEDICINAL PLANT; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION; TANDEM MASS SPECTROMETRY; VIOLA PHILIPPICA; VIOLACEAE;

AMINO ACID SEQUENCE; ANTINEOPLASTIC AGENTS, PHYTOGENIC; CELL LINE, TUMOR; CYCLOTIDES; HELA CELLS; HUMANS; MOLECULAR SEQUENCE DATA; STRUCTURE-ACTIVITY RELATIONSHIP; VIOLA;

VIOLA YEDOENSIS; VIOLACEAE;

EID: 80051552189     PISSN: 01969781     EISSN: 18735169     Source Type: Journal    
DOI: 10.1016/j.peptides.2011.06.016     Document Type: Article

References (45)

1. T.L. Aboye, R.J. Clark, D.J. Craik, and U. Göransson Ultra-stable peptide scaffolds for protein engineering-synthesis and folding of the circular cystine knotted cyclotide cycloviolacin O2 Chembiochem 9 2007 103 113
2. M.L. Colgrave, and D.J. Craik Thermal, chemical, and enzymatic stability of the cyclotide kalata B1: the importance of the cyclic cystine knot Biochemistry 43 2004 5965 5975 (Pubitemid 38669464)
3. M.L. Colgrave, A.G. Poth, Q. Kaas, and D.J. Craik A new "era" for cyclotide sequencing Biopolym Pept Sci 94 2010 592 601
4. D.J. Craik, N.L. Daly, T. Bond, and C. Waine Plant cyclotides: a unique family of cyclic and knotted proteins that defines the cyclic cystine knot structural motif J Mol Biol 294 1999 1327 1336 (Pubitemid 30008803)
5. G.Y. Fu, K. Fu, H.G. Wang, Y.M. Bao, and L. Zhang Extraction and determination of total flavone from Viola philippica Cav by spectrophotometry J Inn Mong Univ Natl (Nat Sci) 23 2008 512 513
6. U. Göransson, A.M. Broussalis, and P. Claeson Expression of Viola cyclotides by liquid chromatography-mass spectrometry and tandem mass spectrometry sequencing of intercysteine loops after introduction of charges and cleavage sites by aminoethylation Anal Biochem 318 2003 107 117 (Pubitemid 36627489)
7. U. Göransson, A. Herrmann, R. Burman, L.M. Haugaard-Jonsson, and K.J. Rosengren The conserved Glu in the cyclotide cycloviolacin O2 has a key structural role Chembiochem 10 2009 2354 2360
8. A.D. Gillon, I. Saska, C.V. Jennings, R.F. Guarino, D.J. Craik, and M.A. Anderson Biosynthesis of circular proteins in plants Plant J 53 2008 505 515 (Pubitemid 351172020)
9. S. Gunasekera, F.M. Foley, R.J. Clark, L. Sando, L.J. Fabri, and D.J. Craik Engineering stabilized vascular endothelial growth factor-A antagonists: synthesis, structural characterization, and bioactivity of grafted analogues of cyclotides J Med Chem 51 2008 7697 7704
10. K.R. Gustafson, R.C. Sowder, L.E. Henderson, I.C. Parsons, Y. Kashman, and J.H. Cardellina Circulins A and B. Novel human immunodeficiency virus (HIV)-inhibitory macrocyclic peptides from the tropical tree Chassalia parvifolia J Am Chem Soc 116 1994 9337 9338
11. J.F. Hernandez, J. Gagnon, L. Chiche, T.M. Nguyen, J.P. Andrieu, and A. Heitz Squash trypsin inhibitors from Momordica cochinchinensis exhibit an atypical macrocyclic structure Biochemistry 39 2000 5722 5730 (Pubitemid 30307960)
12. A. Herrmann, E. Svangard, P. Claeson, J. Gullbo, L. Bohlin, and U. Göransson Key role of glutamic acid for the cytotoxic activity of the cyclotide cycloviolacin O2 Cell Mol Life Sci 63 2006 235 245 (Pubitemid 43100292)
13. D.C. Ireland, M.L. Colgrave, and D.J. Craik A novel suite of cyclotides from Viola odorata: sequence variation and the implications for structure, function and stability Biochem J 400 2006 1 12 (Pubitemid 44763814)
14. D.C. Ireland, M.L. Colgrave, P. Nguyencong, N.L. Daly, and D.J. Craik Discovery and characterization of a linear cyclotide from Viola odorata: implications for the processing of circular proteins J Mol Biol 357 2006 1522 1535
15. K. Jagadish, and J.A. Camarero Cyclotides, a promising molecular scaffold for peptide-based therapeutics Biopolymers Pept Sci 94 2010 611 616
16. C. Jennings, J. West, C. Waine, D. Craik, and M. Anderson Biosynthesis and insecticidal properties of plant cyclotides: the cyclic knotted proteins from Oldenlandia affinis Proc Natl Acad Sci USA 98 2001 10614 10619 (Pubitemid 32878669)
17. Q. Kaas, and D.J. Craik Analysis and classification of circular proteins in CyBase Biopolymers Pept Sci 94 2010 584 591
18. P. Lindholm, U. Göransson, S. Johansson, P. Claeson, J. Gullbo, and R. Larsson Cyclotides: a novel type of cytotoxic agents Mol Cancer Ther 1 2002 365 369
19. J.R. Mulvenna, L. Sando, and D.J. Craik Processing of a 22 kDa precursor protein to produce the circular protein tricyclon A Structure 13 2005 691 701 (Pubitemid 40704658)
20. H. Peng Spermatophyta Z.Y. Wu, Flora Yunnanica 1th ed. 2003 Science Press Beijing 47 48
21. M.R.R. Plan, U. Göransson, R.J. Clark, N.L. Daly, M.L. Colgrave, and D.J. Craik The cyclotide fingerprint in Oldenlandia affinis: elucidation of chemically modified, linear and novel macrocyclic peptides Chembiochem 8 2007 1001 1011 (Pubitemid 47183617)
22. A.G. Poth, M.L. Colgrave, R. Philip, B. Kerenga, N.L. Daly, and M.A. Anderson Discovery of cyclotides in the Fabaceae plant family provides new insights into the cyclization, evolution, and distribution of circular proteins ACS Chem Biol 6 2011 345 355
23. M. Pränting, C. Lööv, R. Burman, U. Göransson, and D.I. Andersson The cyclotide cycloviolacin O2 from Viola odorata has potent bactericidal activity against Gram-negative bacteria J Antimicrob Chemother 65 2010 1964 1971
24. Q. Qin, E. McCallum, Q. Kaas, J. Suda, I. Saska, and D. Craik Identification of candidates for cyclotide biosynthesis and cyclisation by expressed sequence tag analysis of Oldenlandia affinis BMC Genomics 11 2010 111 121
25. K.J. Rosengren, N.L. Daly, M.R. Plan, C. Waine, and D.J. Craik Twists, knots, and rings in proteins - structural definition of the cyclotide framework J Biol Chem 278 2003 8606 8616 (Pubitemid 36800615)
26. O. Saether, D.J. Craik, I.D. Campbell, K. Sletten, J. Juul, and D.G. Norman Elucidation of the primary and three-dimensional structure of the uterotonic polypeptide Kalata B1 Biochemistry 34 1995 4147 4158
27. I. Saska, A.D. Gillon, N. Hatsugai, R.G. Dietzgen, I. Hara-Nishimura, and M.A. Anderson An asparaginyl endopeptidase mediates in vivo protein backbone cyclization J Biol Chem 282 2007 29721 29728 (Pubitemid 350043339)
28. T. Schöepke, M.I. Hasan Agha, R. Kraft, and A. Otto Compounds with hemolytic activity from Viola tricolor L. and Viola arvensis Murray Sci Phar 61 1993 145 153 (Pubitemid 23244214)
29. S.M. Simonsen, L. Sando, D.C. Ireland, M.L. Colgrave, R. Bharathi, and U. Göransson A continent of plant defense peptide diversity: cyclotides in Australian Hybanthus (Violaceae) Plant Cell 17 2005 3176 3189
30. S.M. Simonsen, L. Sando, K.J. Rosengren, C.K. Wang, M.L. Colgrave, and N.L. Daly Alanine scanning mutagenesis of the prototypic cyclotide reveals a cluster of residues essential for bioactivity J Biol Chem 283 2008 9805 9813
31. K. Sletten, and L. Gran Some molecular properties of kalatapeptide B-1. A uterotonic polypeptide isolated from Oldenlandia affinis DC Medd Nor Farm Selsk 7-8 1973 69 82
32. E. Svangard, U. Göransson, Z. Hocaoglu, J. Gullbo, R. Larsson, and P. Claeson Cytotoxic cyclotides from Viola tricolor J Nat Prod 67 2004 144 147 (Pubitemid 38282899)
33. J.P. Tam, Y.A. Lu, J.L. Yang, and K.W. Chiu An unusual structural motif of antimicrobial peptides containing end-to-end macrocycle and cystine-knot disulfides Proc Natl Acad Sci USA 96 1999 8913 8918 (Pubitemid 29374682)
34. N.H. Tan, and J. Zhou Plant cyclopeptides Chem Rev 106 2006 840 895
35. J. Tang, N.H. Tan, W.Y. Xu, C.J. Ji, X.L. Pan, and C. Wang Structure of cyclotide: cycloviolacin O2 Acta Bot Yunnan 30 2008 232 238
36. J. Tang, C.K. Wang, X. Pan, H. Yan, G. Zeng, and W. Xu Isolation and characterization of cytotoxic cyclotides from Viola tricolor Peptides 31 2010 1434 1440
37. J. Tang, C.K. Wang, X.L. Pan, H. Yan, G.Z. Zeng, and W.Y. Xu Isolation and characterization of bioactive cyclotides from Viola labridorica Helv Chim Acta 93 2010 2287 2295
38. M. Trabi, J.S. Mylne, L. Sando, and D.J. Craik Circular proteins from Melicytus (Violaceae) refine the conserved protein and gene architecture of cyclotides Org Biomol Chem 2009 2378 2388
39. J.D. Walton, H.E. Hallen-Adams, and H. Luo Ribosomal biosynthesis of the cyclic peptide toxins of Amanita mushrooms Biopolymers Pept Sci 94 2010 659 664
40. C.K. Wang, S.H. Hu, J.L. Martin, T. Sjogren, J. Hajdu, and L. Bohlin Combined X-ray and NMR analysis 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 2009 10672 10683
41. C.K.L. Wang, M.L. Colgrave, K.R. Gustafson, D.C. Ireland, U. Göransson, and D.J. Craik Anti-HIV cyclotides from the chinese medicinal herb Viola yedoensis J Nat Prod 71 2007 47 52
42. C.K.L. Wang, Q. Kaas, L. Chiche, and D.J. Craik CyBase: a database of cyclic protein sequences and structures, with applications in protein discovery and engineering Nucleic Acids Res 36 2008 1 5
43. K.M. Witherup, M.J. Bogusky, P.S. Anderson, H. Ramjit, R.W. Ransom, and T. Wood Cyclopsychotride A, a biologically active, 31-residue cyclic peptide isolated from Psychotria longipes J Nat Prod 57 1994 1619 1625
44. W.Y. Xu, J. Tang, C.J. Ji, W.J. He, and N.H. Tan Application of a TLC chemical method to detection of cyclotides in plants Chin Sci Bull 53 2008 1671 1674 (Pubitemid 351794067)
45. J. Zhang, B. Liao, D.J. Craik, J.T. Li, M. Hu, and W.S. Shu Identification of two suites of cyclotide precursor genes from metallophyte Viola baoshanensis: cDNA sequence variation, alternative RNA splicing and potential cyclotide diversity Gene 431 2009 23 32