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Cycloviolin-B

* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.

Cycloviolin-B is isolated from Leonia cymosa. It probably participates in a plant defense mechanism. Cycloviolin-B has anti-HIV activity.

Category

Functional Peptides

Catalog number

BAT-012294

Molecular Formula

C120H177N31O40S6

Molecular Weight

2886.26

Specification
Reference Reading

IUPAC Name

3-[(1R,7S,10S,13R,16S,19S,22S,28S,31R,34S,37S,40S,46R,49S,52R,55S,58S,61S,64S,67R,70S,73S,76S,82S,85S)-73-(4-aminobutyl)-76-(2-amino-2-oxoethyl)-64-(3-amino-3-oxopropyl)-34,70-dibenzyl-37,49,55,82-tetrakis[(1R)-1-hydroxyethyl]-10,58,61-tris(hydroxymethyl)-16-[(4-hydroxyphenyl)methyl]-85-methyl-22-(2-methylpropyl)-2,5,8,11,14,17,20,23,29,32,35,38,41,44,47,50,53,56,59,62,65,68,71,74,77,80,83,86-octacosaoxo-19,40-di(propan-2-yl)-89,90,93,94,97,98-hexathia-3,6,9,12,15,18,21,24,30,33,36,39,42,45,48,51,54,57,60,63,66,69,72,75,78,81,84,87-octacosazapentacyclo[44.41.4.413,52.431,67.024,28]nonanonacontan-7-yl]propanoic acid

Sequence

GTACGESCYVLPCFTVGCTCTSSQCFKN

InChI

InChI=1S/C120H177N31O40S6/c1-54(2)37-73-120(191)151-36-20-26-83(151)113(184)143-81-52-196-194-50-79-108(179)132-69(38-62-21-14-12-15-22-62)102(173)130-66(25-18-19-35-121)99(170)135-72(41-85(123)161)97(168)124-44-88(164)145-92(58(8)155)116(187)127-57(7)96(167)140-77-48-192-193-49-78(129-87(163)43-126-114(185)90(55(3)4)147-119(190)95(61(11)158)148-104(175)70(133-110(81)181)39-63-23-16-13-17-24-63)111(182)149-94(60(10)157)118(189)144-82(112(183)150-93(59(9)156)117(188)139-76(47-154)106(177)138-74(45-152)105(176)131-68(101(172)141-79)31-33-84(122)160)53-197-195-51-80(142-107(178)75(46-153)137-100(171)67(32-34-89(165)166)128-86(162)42-125-98(77)169)109(180)134-71(40-64-27-29-65(159)30-28-64)103(174)146-91(56(5)6)115(186)136-73/h12-17,21-24,27-30,54-61,66-83,90-95,152-159H,18-20,25-26,31-53,121H2,1-11H3,(H2,122,160)(H2,123,161)(H,124,168)(H,125,169)(H,126,185)(H,127,187)(H,128,162)(H,129,163)(H,130,173)(H,131,176)(H,132,179)(H,133,181)(H,134,180)(H,135,170)(H,136,186)(H,137,171)(H,138,177)(H,139,188)(H,140,167)(H,141,172)(H,142,178)(H,143,184)(H,144,189)(H,145,164)(H,146,174)(H,147,190)(H,148,175)(H,149,182)(H,150,183)(H,165,166)/t57-,58+,59+,60+,61+,66-,67-,68-,69-,70-,71-,72-,73-,74-,75-,76-,77-,78-,79-,80-,81-,82-,83-,90-,91-,92-,93-,94-,95-/m0/s1

InChI Key

HLXPUKTVQPHDNH-JIQJZISXSA-N

Canonical SMILES

CC1C(=O)NC2CSSCC3C(=O)NC(C(=O)NC4CSSCC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N5CCCC5C(=O)NC(CSSCC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NCC(=O)NC(C(=O)N1)C(C)O)CC(=O)N)CCCCN)CC6=CC=CC=C6)NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC4=O)C(C)O)CO)CO)CCC(=O)N)C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NCC(=O)N3)C(C)C)C(C)O)CC7=CC=CC=C7)CC(C)C)C(C)C)CC8=CC=C(C=C8)O)NC(=O)C(NC(=O)C(NC(=O)CNC2=O)CCC(=O)O)CO)C(C)O

1. Analysis of the disulfide linkage pattern in circulin A and B, HIV-inhibitory macrocyclic peptides

R Derua, K R Gustafson, L K Pannell Biochem Biophys Res Commun. 1996 Nov 12;228(2):632-8. doi: 10.1006/bbrc.1996.1708.

Circulin A and B are members of a family of macrocyclic peptides, originally isolated from the tropical tree Chassalia parvifolia, that have been shown to display anti-HIV activity. Complete structural elucidation of these highly constrained peptides was difficult due to their cyclic amide backbone and the presence of six disulfide-linked cysteines. In the present study, the disulfide pairing motif of circulin A and circulin B was determined. Since the circulins were resistant to enzymatic proteolysis, cysteine residue pairings were identified by analysis of the complex mixture of cleavage products that resulted from partial acid hydrolysis of the native peptides. Combined utilization of HPLC, fast atom bombardment mass spectrometry and peptide recognition software ("F-MASS" and "F-LINK" programs) were employed to identify the cleavage products. Thus, we were able to unambiguously identify the disulfide linkage pattern in circulin A and circulin B as Cys1-Cys4, Cys2-Cys5 and Cys3-Cys6, where the numbers on the cystine residues refer to their respective order in the peptides.

2. New circulin macrocyclic polypeptides from Chassalia parvifolia

K R Gustafson, L K Walton, R C Sowder Jr, D G Johnson, L K Pannell, J H Cardellina Jr, M R Boyd J Nat Prod. 2000 Feb;63(2):176-8. doi: 10.1021/np990432r.

Four new macrocyclic polypeptides were isolated and identified from an extract of the tropical tree Chassalia parvifolia. Circulins C-F are 29-30 amino acid cyclic peptides in which the entire primary amino acid chain is covalently cyclized via peptide bonds. Their structures were deduced from a combination of FABMS analyses, N-terminal Edman degradation, endoproteinase digestion, and amino acid analyses. All the peptides share a high degree of sequence homology and contain six cysteine residues forming three intramolecular disulfide bridges. Circulins C-F inhibited the cytopathic effects of in vitro HIV-1 infection with EC(50) values of 50-275 nM.

3. Seven novel macrocyclic polypeptides from Viola arvensis

U Göransson, T Luijendijk, S Johansson, L Bohlin, P Claeson J Nat Prod. 1999 Feb;62(2):283-6. doi: 10.1021/np9803878.

Seven novel macrocyclic polypeptides, designated as varv peptides B-H, have been isolated from the aerial parts of Viola arvensis. Their primary structures have been elucidated by automated Edman degradation and mass spectrometry. They all consist of 29 or 30 amino acid residues, covalently cyclized via the amide backbone and by three internal disulfide bridges. Their amino acid sequences are as follows: varv peptide B, cyclo-(TCFGGTCNTPGCSCDPWPMCSRNGLPVCGE); varv peptide C, cyclo-(TCVGGTCNTPGCSCSWPVCTRNGVPICGE); varv peptide D, cyclo-(TCVGGSCNTPGCSCSWPVCTRNGLPICGE); varv peptide E, cyclo-(TCVGGTCNTPGCSCSWPVCTRNGLPICGE); varv peptide F, cyclo-(TCTLGTCYTAGCSCSWPVCTRNGVPICGE); varv peptide G, cyclo-(TCFGGTCNTPGCSCDPWPVCSRNGVPVCGE); and varv peptide H, cyclo-(TCFGGTCNTPGCSCETWPVCSRNGLPVCGE). The varv peptides B-H exhibited high degrees of homology with the hitherto known macrocyclic peptides varv peptide A, kalata B1, violapeptide I, circulins A and B, and cyclopsychotride A.