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First cyclotide from Hybanthus (Violaceae)
Uppsala universitet, Medicinska och farmaceutiska vetenskapsområdet, Farmaceutiska fakulteten, Institutionen för läkemedelskemi, Avdelningen för farmakognosi.
Vise andre og tillknytning
2001 (engelsk)Inngår i: Phytochemistry, ISSN 0031-9422, E-ISSN 1873-3700, Vol. 58, nr 1, s. 47-51Artikkel i tidsskrift (Fagfellevurdert) Published
Abstract [en]

Hypa A, a novel macrocyclic polypeptide containing 30 amino acid residues, has been isolated from the n-butanol extract of the Argentine plant Hybanthus parviflorus. The sequence, cyclo-(SCVYIPCTITALLGCSCKNKVCYNGIPCAE), was determined by automated Edman degradation, quantitative amino acid analysis and nanospray MS/MS(2). Three intramolecular disulfide bridges stabilize the cyclic peptide backbone of hypa A. Using these structural features to classify the peptide as a cyclotide, we extended the distribution of that substance class to a new genus, and now propose a uniform nomenclature for cyclotides.

sted, utgiver, år, opplag, sider
2001. Vol. 58, nr 1, s. 47-51
HSV kategori
Identifikatorer
URN: urn:nbn:se:uu:diva-89793DOI: 10.1016/S0031-9422(01)00173-XPubMedID: 11524112OAI: oai:DiVA.org:uu-89793DiVA, id: diva2:161547
Tilgjengelig fra: 2002-04-05 Laget: 2002-04-05 Sist oppdatert: 2017-12-14bibliografisk kontrollert
Inngår i avhandling
1. Macrocyclic polypeptides from plants
Åpne denne publikasjonen i ny fane eller vindu >>Macrocyclic polypeptides from plants
2002 (engelsk)Doktoravhandling, med artikler (Annet vitenskapelig)
Abstract [en]

The aim of this work was to explore the structural and functional diversity of polypeptides that are found in plants. Expanding knowledge of simililarities between plant use of these compound and animal use promises exceptional opportunities for finding, from plant research, new structures with biomedical and biotechnological potential.

A fractionation protocol was developed and applied to many plant species, providing fractions enriched in polypeptides, amenable to chemical and biological evaluation. From one species, the common field pansy (Viola arvensis), a 29-amino-acid residue polypeptide was isolated, named varv A, which revealed a remarkable macrocyclic structure (i.e., N- and C-termini are joined) stabilised by three knotted disulfides.

Varv A, together with an increasing number of homologous peptides, form the currently known peptide family of cyclotides. Their stable structure makes them an attractive scaffold for protein engineering. In addition, they display a wide range of biological activities (e.g., antimicrobial, cytotoxic, and insecticidal). As a part of this work, the cytotoxic effects of varv A and two other isolated cyclotides were evaluated in a human cell-line panel: all were active in the low µM range. Most likely, these effects involve pore formation through cell membranes.

Cyclotides were found to be common in the plant family Violaceae; with eleven cyclotides isolated and sequenced from V. arvensis, V. cotyledon, and Hybanthus parviflorus. For six members of the genus Viola, cyclotide expression profiles were examined by liquid chromatography-mass spectrometry (LC-MS): all expressed notably complex mixtures, with single species containing more than 50 cyclotides. These profiles reflect the evolution of the genus.

To assess these mixtures, a rational strategy for MS based amino acid sequencing of cyclotides was developed, circumventing inherent structural problems, such as low content of positively charged amino acids and the macrocyclic structure. This was achieved by aminoethylation of cysteines, which, following tryptic digestion, produced fragments of size and charge amenable to MS analysis. This method was also modified and used for mapping of disulfide bonds.

Methods for isolation and characterisation developed in this work may prove useful not only for further studies on macrocyclic polypeptides from plants, but also for other plant peptides and disulfide-rich peptides from animals.

sted, utgiver, år, opplag, sider
Uppsala: Acta Universitatis Upsaliensis, 2002. s. 59
Serie
Comprehensive Summaries of Uppsala Dissertations from the Faculty of Pharmacy, ISSN 0282-7484 ; 270
Emneord
Pharmaceutical chemistry, Farmaceutisk kemi
HSV kategori
Forskningsprogram
Farmakognosi
Identifikatorer
urn:nbn:se:uu:diva-1956 (URN)91-554-5279-5 (ISBN)
Disputas
2002-04-26, BMC sal B22, Uppsala, 10:15
Opponent
Tilgjengelig fra: 2002-04-05 Laget: 2002-04-05 Sist oppdatert: 2018-01-13bibliografisk kontrollert

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