Craik DJ, Daly NL, Bond T, 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
Article
CAS
PubMed
Google Scholar
Gruber CW, Elliott AG, Ireland DC, Delprete PG, Dessein S, Göransson U, Trabi M, Wang CK, Kinghorn AB, Robbrecht E, Craik DJ (2008) Distribution and evolution of circular miniproteins in flowering plants. Plant Cell 20:2471–2483
Article
CAS
PubMed
Google Scholar
Trabi M, Mylne JS, Sando L, Craik DJ (2009) Circular proteins from Melicytus (Violaceae) refine the conserved protein and gene architecture of cyclotides. Org Biomol Chem 7:2378–2388
Article
CAS
PubMed
Google Scholar
Trabi M, Svangard E, Herrmann A, Göransson U, Claeson P, Craik DJ, Bohlin L (2004) Variations in cyclotide expression in Viola species. J Nat Prod 67:806–810
Article
CAS
PubMed
Google Scholar
Gran L (1970) An oxytocic principle found in Oldenlandia affinis DC. Medd Nor Farm Selsk 12:173–180
Google Scholar
Gustafson KR, Sowder RCI, Henderson LE, Parsons IC, Kashman Y, Cardellina JHI, McMahon JB, Buckheit RWJ, Pannell LK, Boyd MR (1994) Circulins A and B: novel HIV-inhibitory macrocyclic peptides from the tropical tree Chassalia parvifolia. J Am Chem Soc 116:9337–9338
Article
CAS
Google Scholar
Schöpke T, Hasan Agha MI, Kraft R, Otto A, Hiller K (1993) Hämolytisch aktive komponenten aus Viola tricolor L. und Viola arvensis Murray. Sci Pharm 61:145–153
Google Scholar
Witherup KM, Bogusky MJ, Anderson PS, Ramjit H, Ransom RW, Wood T, Sardana M (1994) Cyclopsychotride A, a biologically active, 31-residue cyclic peptide isolated from Psychotria longipes. J Nat Prod 57:1619–1625
Article
CAS
PubMed
Google Scholar
Ireland DC, Wang CK, Wilson JA, Gustafson KR, Craik DJ (2008) Cyclotides as natural anti-HIV agents. Biopolymers Pept Sci 90:51–60
Article
CAS
Google Scholar
Cemazar M, Gruber CW, Craik DJ (2008) Oxidative folding of cyclic cystine knot proteins. Antioxid Redox Signal 10:103–111
Article
CAS
PubMed
Google Scholar
Craik DJ, Clark RJ, Daly NL (2007) Potential therapeutic applications of the cyclotides and related cystine knot mini-proteins. Expert Opin Investig Drugs 16:595–604
Article
CAS
PubMed
Google Scholar
Craik DJ, Cemazar M, Daly NL (2007) The chemistry and biology of cyclotides. Curr Opin Drug Discovery Dev 10:176–184
CAS
Google Scholar
Gruber CW, Cemazar M, Anderson MA, Craik DJ (2007) Insecticidal plant cyclotides and related cystine knot toxins. Toxicon 49:561–575
Article
CAS
PubMed
Google Scholar
Pelegrini PB, Quirino BF, Franco OL (2007) Plant cyclotides: an unusual class of defense compounds. Peptides 28:1475–1481
Article
CAS
PubMed
Google Scholar
Göransson U, Svangard E, Claeson P, Bohlin L (2004) Novel strategies for isolation and characterization of cyclotides: the discovery of bioactive macrocyclic plant polypeptides in the Violaceae. Curr Protein Pept Sci 5:317–329
Article
PubMed
Google Scholar
Jennings C, West J, Waine C, Craik D, Anderson M (2001) Biosynthesis and insecticidal properties of plant cyclotides: the cyclic knotted proteins from Oldenlandia affinis. Proc Natl Acad Sci USA 98:10614–10619
Article
CAS
PubMed
Google Scholar
Tan N-H, Zhou J (2006) Plant cyclopeptides. Chem Rev 106:840–895
Article
CAS
PubMed
Google Scholar
Saska I, Gillon AD, Hatsugai N, Dietzgen RG, Hara-Nishimura I, Anderson MA, Craik DJ (2007) An asparaginyl endopeptidase mediates in vivo protein backbone cyclisation. J Biol Chem 282:29721–29728
Article
CAS
PubMed
Google Scholar
Gillon AD, Saska I, Jennings CV, Guarino RF, Craik DJ, Anderson MA (2008) Biosynthesis of circular proteins in plants. Plant J 53:505–515
Article
CAS
PubMed
Google Scholar
Tang Y-Q, Yuan J, Ösapay G, Ösapay K, Tran D, Miller CJ, Ouellette AJ, Selsted ME (1999) A cyclic antimicrobial peptide produced in primate leukocytes by the ligation of two truncated α-defensins. Science 286:498–502
Article
CAS
PubMed
Google Scholar
Trabi M, Craik DJ (2002) Circular proteins—no end in sight. Trends Biochem Sci 27:132–138
Article
CAS
PubMed
Google Scholar
Maqueda M, Galvez A, Bueno MM, Sanchez-Barrena MJ, Gonzalez C, Albert A, Rico M, Valdivia E (2004) Peptide AS-48: prototype of a new class of cyclic bacteriocins. Curr Protein Pept Sci 5:399–416
Article
CAS
PubMed
Google Scholar
Craik DJ (2006) Seamless proteins tie up their loose ends. Science 311:1563–1564
Article
PubMed
Google Scholar
Hallen HE, Luo H, Scott-Craig JS, Walton JD (2007) Gene family encoding the major toxins of lethal Amanita mushrooms. Proc Natl Acad Sci USA 104:19097–19101
Article
CAS
PubMed
Google Scholar
Donia MS, Ravel J, Schmidt EW (2008) A global assembly line for cyanobactins. Nat Chem Biol 4:341–343
Article
CAS
PubMed
Google Scholar
Gran L, Sandberg F, Sletten K (2000) Oldenlandia affinis (R&S) DC: a plant containing uteroactive peptides used in African traditional medicine. J Ethnopharmacol 70:197–203
Article
CAS
PubMed
Google Scholar
Claeson P, Göransson U, Johansson S, Luijendijk T, Bohlin L (1998) Fractionation protocol for the isolation of polypeptides from plant biomass. J Nat Prod 61:77–81
Article
CAS
PubMed
Google Scholar
Göransson U, Luijendijk T, Johansson S, Bohlin L, Claeson P (1999) Seven novel macrocyclic polypeptides from Viola arvensis. J Nat Prod 62:283–286
Article
PubMed
Google Scholar
Craik DJ (2009) Circling the enemy: cyclic proteins in plant defence. Trends Plant Sci 14:328–335
Article
CAS
PubMed
Google Scholar
Barbeta BL, Marshall AT, Gillon AD, Craik DJ, Anderson MA (2008) Plant cyclotides disrupt epithelial cells in the midgut of lepidopteran larvae. Proc Natl Acad Sci USA 105:1221–1225
Article
CAS
PubMed
Google Scholar
Jennings CV, Rosengren KJ, Daly NL, Plan M, Stevens J, Scanlon MJ, Waine C, Norman DG, Anderson MA, Craik DJ (2005) Isolation, solution structure, and insecticidal activity of kalata B2, a circular protein with a twist: do Möbius strips exist in nature? Biochemistry 44:851–860
Article
CAS
PubMed
Google Scholar
Tam JP, Lu YA, Yang JL, Chiu KW (1999) An unusual structural motif of antimicrobial peptides containing end-to-end macrocycle and cystine-knot disulfides. Proc Natl Acad Sci USA 96:8913–8918
Article
CAS
PubMed
Google Scholar
Göransson U, Sjogren M, Svangard E, Claeson P, Bohlin L (2004) Reversible antifouling effect of the cyclotide cycloviolacin O2 against barnacles. J Nat Prod 67:1287–1290
Article
PubMed
Google Scholar
Lindholm P, Göransson U, Johansson S, Claeson P, Gulbo J, Larsson R, Bohlin L, Backlund A (2002) Cyclotides: a novel type of cytotoxic agents. Mol Cancer Ther 1:365–369
CAS
PubMed
Google Scholar
Plan MR, Saska I, Cagauan AG, Craik DJ (2008) Backbone cyclised peptides from plants show molluscicidal activity against the rice pest Pomacea canaliculata (golden apple snail). J Agric Food Chem 56:5237–5241
Article
CAS
PubMed
Google Scholar
Colgrave ML, Kotze AC, Huang YH, O’Grady J, Simonsen SM, Craik DJ (2008) Cyclotides: natural, circular plant peptides that possess significant activity against gastrointestinal nematode parasites of sheep. Biochemistry 47:5581–5589
Article
CAS
PubMed
Google Scholar
Colgrave ML, Kotze AC, Ireland DC, Wang CK, Craik DJ (2008) The anthelmintic activity of the cyclotides: natural variants with enhanced activity. ChemBioChem 9:1939–1945
Article
CAS
PubMed
Google Scholar
Colgrave ML, Kotze AC, Kopp S, McCarthy JS, Coleman GT, Craik DJ (2009) Anthelmintic activity of cyclotides: in vitro studies with canine and human hookworms. Acta Trop 109:163–166
Article
CAS
PubMed
Google Scholar
Gran L, Sletten K, Skjeldal L (2008) Cyclic peptides from Oldenlandia affinis DC: molecular and biological properties. Chem Biodivers 5:2014–2022
Article
CAS
PubMed
Google Scholar
Kamimori H, Hall K, Craik DJ, Aguilar MI (2005) Studies on the membrane interactions of the cyclotides kalata B1 and kalata B6 on model membrane systems by surface plasmon resonance. Anal Biochem 337:149–153
Article
CAS
PubMed
Google Scholar
Shenkarev ZO, Nadezhdin KD, Sobol VA, Sobol AG, Skjeldal L, Arseniev AS (2006) Conformation and mode of membrane interaction in cyclotides: spatial structure of kalata B1 bound to a dodecylphosphocholine micelle. FEBS J. 273:2658–2672
Article
CAS
PubMed
Google Scholar
Shenkarev ZO, Nadezhdin KD, Lyukmanova EN, Sobol VA, Skjeldal L, Arseniev AS (2008) Divalent cation coordination and mode of membrane interaction in cyclotides: NMR spatial structure of ternary complex Kalata B7/Mn2+/DPC micelle. J Inorg Biochem 102:1246–1256
Article
CAS
PubMed
Google Scholar
Wang CK, Colgrave ML, Ireland DC, Kaas Q, Craik DJ (2009) Despite a conserved cystine knot motif, different cyclotides have different membrane binding modes. Biochem J 97:1471–1481
Google Scholar
Nourse A, Trabi M, Daly NL, Craik DJ (2004) A comparison of the self-association behavior of the plant cyclotides kalata B1 and kalata B2 via analytical ultracentrifugation. J Biol Chem 279:562–570
Article
CAS
PubMed
Google Scholar
Simonsen SM, Sando L, Rosengren KJ, Wang CK, Colgrave ML, Daly NL, Craik DJ (2008) Alanine scanning mutagenesis of the prototypic cyclotide reveals a cluster of residues essential for bioactivity. J Biol Chem 283:9805–9813
Article
CAS
PubMed
Google Scholar
Huang YH, Colgrave ML, Daly NL, Keleshian A, Martinac B, Craik DJ (2009) The biological activity of the prototypic cyclotide kalata B1 is modulated by the formation of multimeric pores. J Biol Chem 284:20699–20707
Article
CAS
PubMed
Google Scholar
Svangard E, Burman R, Gunasekera S, Lovborg H, Gullbo J, Göransson U (2007) Mechanism of action of cytotoxic cyclotides: cycloviolacin O2 disrupts lipid membranes. J Nat Prod 70:643–647
Article
PubMed
Google Scholar
Barry DG, Daly NL, Clark RJ, Sando L, Craik DJ (2003) Linearization of a naturally occurring circular protein maintains structure but eliminates hemolytic activity. Biochemistry 42:6688–6695
Article
CAS
PubMed
Google Scholar
Daly NL, Craik DJ (2000) Acyclic permutants of naturally occurring cyclic proteins: characterization of cystine knot and beta-sheet formation in the macrocyclic polypeptide kalata B1. J Biol Chem 275:19068–19075
Article
CAS
PubMed
Google Scholar
Herrmann A, Burman R, Mylne JS, Karlsson G, Gullbo J, Craik DJ, Clark RJ, Göransson U (2008) The alpine violet, Viola biflora, is a rich source of cyclotides with potent cytotoxicity. Phytochemistry 69:939–952
Article
CAS
PubMed
Google Scholar
Mulvenna JP, Mylne JS, Bharathi R, Burton RA, Shirley NJ, Fincher GB, Anderson MA, Craik DJ (2006) Discovery of cyclotide-like protein sequences in graminaceous crop plants: ancestral precursors of circular proteins? Plant Cell 18:2134–2144
Article
CAS
PubMed
Google Scholar
Basse CW (2005) Dissecting defense-related and developmental transcriptional responses of maize during Ustilago maydis infection and subsequent tumor formation. Plant Physiol 138:1774–1784
Article
CAS
PubMed
Google Scholar
Rosengren KJ, Daly NL, Plan MR, Waine C, Craik DJ (2003) Twists, knots, and rings in proteins. Structural definition of the cyclotide framework. J Biol Chem 278:8606–8616
Article
CAS
PubMed
Google Scholar
Herrmann A, Svangard E, Claeson P, Gullbo J, Bohlin L, Goransson U (2006) Key role of glutamic acid for the cytotoxic activity of the cyclotide cycloviolacin O2. Cell Mol Life Sci 63:235–245
Article
CAS
PubMed
Google Scholar
Saska I, Craik DJ (2008) Protease-catalysed protein splicing: a new post-translational modification? Trends Biochem Sci 33:363–368
Article
CAS
PubMed
Google Scholar
Daly NL, Love S, Alewood PF, Craik DJ (1999) Chemical synthesis and folding of large cyclic polypeptides: studies of the cystine knot polypeptide kalata B1. Biochemistry 38:10606–10614
Article
CAS
PubMed
Google Scholar
Kent SB (2009) Total chemical synthesis of proteins. Chem Soc Rev 38:338–351
Article
CAS
PubMed
Google Scholar
Gruber CW, Cemazar M, Clark RJ, Horibe T, Renda RF, Anderson MA, Craik DJ (2007) A novel plant protein-disulfide isomerase involved in the oxidative folding of cystine knot defense proteins. J Biol Chem 282:20435–20446
Article
CAS
PubMed
Google Scholar
Andeme-Ondzighi C, Christopher DA, Cho EJ, Chang SC, Staehelin LA (2008) Arabidopsis protein disulfide isomerase-5 inhibits cysteine proteases during trafficking to vacuoles before programmed cell death of the endothelium in developing seeds. Plant Cell 20:2205–2220
Article
PubMed
Google Scholar
Gunasekera S, Daly NL, Anderson MA, Craik DJ (2006) Chemical synthesis and biosynthesis of the cyclotide family of circular proteins. IUBMB Life 58:515–524
Article
CAS
PubMed
Google Scholar
Kimura RH, Tran A-T, Camarero JA (2006) Biosynthesis of the cyclotide kalata B1 by using protein splicing. Angew Chem Int Ed Engl 118:987–990
Article
Google Scholar
Camarero JA, Kimura RH, Woo Y-H, Shekhtman A, Cantor J (2007) Biosynthesis of a fully functional cyclotide inside living bacterial cells. ChemBioChem 8:1363–1366
Article
CAS
PubMed
Google Scholar
Thongyoo P, Jaulent AM, Tate EW, Leatherbarrow RJ (2007) Immobilized protease-assisted synthesis of engineered cysteine-knot microproteins. ChemBioChem 8:1107–1109
Article
CAS
PubMed
Google Scholar
Gunasekera S, Foley FM, Clark RJ, Sando L, Fabri LJ, Craik DJ, Daly NL (2008) Engineering stabilized vascular endothelial growth factor-A antagonists: synthesis, structural characterization, and bioactivity of grafted analogues of cyclotides. J Med Chem 51:7697–7704
Article
CAS
PubMed
Google Scholar
Thongyoo P, Roque-Rosell N, Leatherbarrow RJ, Tate EW (2008) Chemical and biomimetic total syntheses of natural and engineered MCoTI cyclotides. Org Biomol Chem 6:1462–1470
Article
CAS
PubMed
Google Scholar
Werle M, Kafedjiiski K, Kolmar H, Bernkop-Schnurch A (2007) Evaluation and improvement of the properties of the novel cystine-knot microprotein McoEeTI for oral administration. Int J Pharm 332:72–79
Article
CAS
PubMed
Google Scholar
Reiss S, Sieber M, Oberle V, Wentzel A, Spangenberg P, Claus R, Kolmar H, Losche W (2006) Inhibition of platelet aggregation by grafting RGD and KGD sequences on the structural scaffold of small disulfide-rich proteins. Platelets 17:153–157
Article
CAS
PubMed
Google Scholar
Werle M, Schmitz T, Huang HL, Wentzel A, Kolmar H, Bernkop-Schnurch A (2006) The potential of cystine-knot microproteins as novel pharmacophoric scaffolds in oral peptide drug delivery. J Drug Target 14:137–146
Article
CAS
PubMed
Google Scholar
Seydel P, Dörnenburg H (2006) Establishment of in vitro plants, cell and tissue cultures from Oldenlandia affinis for the production of cyclic peptides. Plant Cell Tissue Organ Cult 85:247–255
Article
Google Scholar
Seydel P, Gruber CW, Craik DJ, Dörnenburg H (2007) Formation of cyclotides and variations in cyclotide expression in Oldenlandia affinis suspension cultures. Appl Microbiol Biotechnol 77:275–284
Article
CAS
PubMed
Google Scholar
Dörnenburg H (2008) Plant cell culture technology-harnessing a biological approach for competitive cyclotides production. Biotechnol Lett 30:1311–1321
Article
PubMed
Google Scholar
Hernandez JF, Gagnon J, Chiche L, Nguyen TM, Andrieu JP, Heitz A, Trinh Hong T, Pham TT, Le Nguyen D (2000) Squash trypsin inhibitors from Momordica cochinchinensis exhibit an atypical macrocyclic structure. Biochemistry 39:5722–5730
Article
CAS
PubMed
Google Scholar
Dutton JL, Renda RF, Waine C, Clark RJ, Daly NL, Jennings CV, Anderson MA, Craik DJ (2004) Conserved structural and sequence elements implicated in the processing of gene-encoded circular proteins. J Biol Chem 279:46858–46867
Article
CAS
PubMed
Google Scholar
Zhang J, Liao B, Craik DJ, Li J-T, Hu M, Shu W-S (2009) Identification of two suites of cyclotide precursor genes from metallophyte Viola baoshanensis: cDNA sequence variation, alternative RNA splicing and potential cyclotide diversity. Gene 431:23–32
Article
CAS
PubMed
Google Scholar
Saska I, Colgrave ML, Jones A, Anderson MA, Craik DJ (2008) Quantitative analysis of backbone-cyclised peptides in plants. J Chromatogr B Analyt Technol Biomed Life Sci 872:107–114
Article
CAS
PubMed
Google Scholar
Mylne JS, Craik DJ (2008) 15N cyclotides by whole plant labeling. Biopolym Pept Sci 90:575–580
Article
CAS
Google Scholar