A new family of cystine knot peptides from the seeds of Momordica cochinchinensis

Peptides

Volumn 39, Issue 1, 2013, Pages 29-35

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

^a UNIVERSITY OF QUEENSLAND   (Australia)

^b KUNMING INSTITUTE OF BOTANY   (China)

Author keywords

Cystine knot; MCo 3 to MCo 6; Momordica cochinchinensis; Peptides

Indexed keywords

MCO 1 PEPTIDE; MCO 2 PEPTIDE; MCO 3 PEPTIDE; MCO 4 PEPTIDE; MCO 5 PEPTIDE; MCO 6 PEPTIDE; PEPTIDE DERIVATIVE; TRYPSIN; TRYPSIN INHIBITOR; UNCLASSIFIED DRUG;

ALKYLATION; AMINO ACID SEQUENCE; ANTIMALARIAL ACTIVITY; ARTICLE; CANCER CELL; CYSTINE KNOT MOTIF; DIASTEREOISOMER; DISULFIDE BOND; DRUG ISOLATION; DRUG STRUCTURE; ENZYME INHIBITION; HUMAN; HUMAN CELL; MOMORDICA COCHINCHINENSIS; NONHUMAN; PLANT SEED; PLASMODIUM FALCIPARUM; PRIORITY JOURNAL; PROTEIN MOTIF; PROTON NUCLEAR MAGNETIC RESONANCE; REDUCTION; SEQUENCE ANALYSIS; SEQUENCE HOMOLOGY;

AMINO ACID SEQUENCE; ANTIMALARIALS; ANTINEOPLASTIC AGENTS, PHYTOGENIC; CELL LINE, TUMOR; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; MOLECULAR SEQUENCE DATA; MOLECULAR WEIGHT; MOMORDICA; PEPTIDES; PLANT EXTRACTS; PLANT PROTEINS; PLASMODIUM FALCIPARUM; SEEDS; SEQUENCE ANALYSIS, PROTEIN; TANDEM MASS SPECTROMETRY;

CUCURBITACEAE; MOMORDICA COCHINCHINENSIS; PLASMODIUM FALCIPARUM;

EID: 84870188313     PISSN: 01969781     EISSN: 18735169     Source Type: Journal    
DOI: 10.1016/j.peptides.2012.09.018     Document Type: Article

References (37)

1. O. Avrutina, H.U. Schmoldt, D. Gabrijelcic-Geiger, D. Le Nguyen, C.P. Sommerhoff, and U. Diederichsen Trypsin inhibition by macrocyclic and open-chain variants of the squash inhibitor MCoTI-II Biol Chem 386 2005 1301 1306
2. K. Begum, H.S. Kim, V. Kumar, I. Stojiljkovic, and Y. Wataya In vitro antimalarial activity of metalloporphyrins against Plasmodium falciparum Parasitol Res 90 2003 221 224
3. L. Braunschweiler, and R.R. Ernst Coherence transfer by isotropic mixing: application to proton correlation spectroscopy J Magn Reson 53 1983 521 528
4. M. Cemazar, A. Joshi, N.L. Daly, A.E. Mark, and D.J. Craik The structure of a two-disulfide intermediate assists in elucidating the oxidative folding pathway of a cyclic cystine knot protein Structure 16 2008 842 851
5. L.Y. Chan, C.K. Wang, J.M. Major, K.P. Greenwood, R.J. Lewis, and D.J. Craik Isolation and characterization of peptides from Momordica cochinchinensis seeds J Nat Prod 72 2009 1453 1458
6. B. Chen, M.L. Colgrave, N.L. Daly, K.J. Rosengren, K.R. Gustafson, and D.J. Craik Isolation and characterization of novel cyclotides from Viola hederaceae-solution structure and anti-HIV activity of vhl-1, a leaf-specific expressed cyclotide J Biol Chem 280 2005 22395 22405
7. J. Chen, and S.K. Chen Spermatophyta Z.Y. Wu, Flora Yunnanica 1st ed. 1995 Science Press Beijing 329 330
8. L. Chiche, A. Heitz, J.C. Gelly, J. Gracy, P.T. Chau, and P.T. Ha Squash inhibitors: from structural motifs to macrocyclic knottins Curr Protein Pept Sci 5 2004 341 349
9. P. Claeson, U. Göransson, S. Johansson, T. Luijendijk, and L. Bohlin Fractionation protocol for the isolation of polypeptides from plant biomass J Nat Prod 61 1998 77 81
10. 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
11. D.J. Craik Plant cyclotides: circular, knotted peptide toxins Toxicon 39 2001 1809 1813
12. 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
13. D.J. Craik, N.L. Daly, and C. Waine The cystine knot motif in toxins and implications for drug design Toxicon 39 2001 43 60
14. N.L. Daly, and D.J. Craik Bioactive cystine knot proteins Curr Opin Chem Biol 15 2011 362 368
15. A. Favel, H. Mattras, M.A. Coletti-Previero, R. Zwilling, E.A. Robinson, and B. Castro Protease inhibitors from Ecballium elaterium seeds Int J Pept Protein Res 33 1989 202 208
16. M.E. Felizmenio-Quimio, N.L. Daly, and D.J. Craik Circular proteins in plants: solution structure of a novel macrocyclic trypsin inhibitor from Momordica cochinchinensis J Biol Chem 276 2001 22875 22882
17. S.F. Foley, Y. Sun, T.S. Zheng, and D. Wen Picomole-level mapping of protein disulfides by mass spectrometry following partial reduction and alkylation Anal Biochem 377 2008 95 104
18. U. Göransson, and D.J. Craik Disulfide mapping of the cyclotide kalata B1-chemical proof of the cyclic cystine knot motif J Biol Chem 278 2003 48188 48196
19. J. Gracy, D. Le-Nguyen, J.-C. Gelly, Q. Kaas, A. Heitz, and L. Chiche KNOTTIN: the knottin or inhibitor cystine knot scaffold in 2007 Nucleic Acids Res 36 2007 D314 D319
20. W.J. He, L.Y. Chan, G.Z. Zeng, N.L. Daly, D.J. Craik, and N.H. Tan Isolation and characterization of cytotoxic cyclotides from Viola philippica Peptides 32 2011 1719 1723
21. 1H 2D NMR and distance geometry study of the folding of Ecballium elaterium trypsin inhibitor, a member of the squash inhibitors family Biochemistry 28 1989 2392 2398
22. A. Heitz, J.F. Hernandez, J. Gagnon, T.T. Hong, T.T.C. Pham, and T.M. Nguyen Solution structure of the squash trypsin inhibitor MCoTI-II. A new family for cyclic knottins Biochemistry 40 2001 7973 7983
23. 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
24. J. Jeener, B.H. Meier, P. Bachmann, and R.R. Ernst Investigation of exchange processes by two-dimensional NMR spectroscopy J Chem Phys 71 1979 4546 4553
25. Goddard TD, Kneller DG., SPARKY 3, University of California, San Francisco.
26. B.C. Lee, and V.N. Gladyshev The biological significance of methionine sulfoxide stereochemistry Free Radic Biol Med 50 2011 221 227
27. N.H. Tan, and J. Zhou Plant cyclopeptides Chem Rev 106 2006 840 895
28. J. Tang, N.H. Tan, W.Y. Xu, C.J. Ji, X.L. Pan, and C.K. Wang Structure of cyclotide: cycloviolacin O2 Acta Bot Yunnan 30 2008 232 238
29. 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
30. J. Tang, C.K. Wang, X.L. Pan, H. Yan, G.Z. Zeng, and W.Y. Xu Isolation and characterization of cytotoxic cyclotides from Viola tricolor Peptides 31 2010 1434 1440
31. A.Y.-K. Tsoi, T.-B. Ng, and W.-P. Fong Antioxidative effect of a chymotrypsin inhibitor from Momordica cochinchinensis (Cucurbitaceae) seeds in a primary rat hepatocyte culture J Pept Sci 11 2005 665 668
32. C.K. 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
33. A.A. Watson, D.P. Fairlie, and D.J. Craik Solution structure of methionine-oxidized amyloid β-peptide (1-40). Does oxidation affect conformational switching? Biochemistry 37 1998 12700 12706
34. R.C.H. Wong, W.P. Fong, and T.B. Ng Multiple trypsin inhibitors from Momordica cochinchinensis seeds, the Chinese drug mubiezhi Peptides 25 2004 163 169
35. K. Wüthrich NMR of proteins and nucleic acids 1986 Wiley-Interscience New York
36. 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
37. J. Zhou, and N.H. Tan Application of a new TLC chemical method for detection of cyclopeptides in plants Chin Sci Bull 45 2000 1825 1831