Cycloviolins A-D, anti-HIV macrocyclic peptides from Leonia cymosa

Four novel anti-HIV macrocyclic peptides containing 28-31 amino acid residues, named cycloviolins A-D, have been isolated from the hitherto unstudied tropical plant Leonia cymosa. Their primary structure, including amino acid composition and sequence, was determined by a combination of MALDI-TOF and...

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Bibliographic Details
Published in:Journal of organic chemistry 2000-01, Vol.65 (1), p.124-128
Main Authors: Hallock, Y F, Sowder, 2nd, R C, Pannell, L K, Hughes, C B, Johnson, D G, Gulakowski, R, Cardellina, 2nd, J H, Boyd, M R
Format: Article
Language:English
Subjects:
AIDS/HIV
Amino Acid Sequence
Anti-HIV Agents - chemistry
Anti-HIV Agents - isolation & purification
Chromatography, High Pressure Liquid
Magnetic Resonance Spectroscopy
Molecular Sequence Data
Peptides, Cyclic - chemistry
Peptides, Cyclic - isolation & purification
Plants - chemistry
Sequence Homology, Amino Acid
Spectrometry, Mass, Fast Atom Bombardment
Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization
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Summary:Four novel anti-HIV macrocyclic peptides containing 28-31 amino acid residues, named cycloviolins A-D, have been isolated from the hitherto unstudied tropical plant Leonia cymosa. Their primary structure, including amino acid composition and sequence, was determined by a combination of MALDI-TOF and FAB MS and by enzymatic digestion of reduced derivatives, followed by Edman degradation and mass analyses. All of the cycloviolins contain six cysteines, which are present as three intramolecular disulfide bridges. Intriguingly, cycloviolins A-D showed high degrees of sequence homology to the known cyclopsychotride A and circulins A and B from the Rubiaceae family but much less homology to the varv peptides from Viola, a member of the same family (Violaceae).
ISSN:0022-3263
DOI:10.1021/jo990952r