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Violacin A

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

Violacin A is an antibacterial peptide isolated from Viola odorata. It has low hemolytic activity.

Category

Functional Peptides

Catalog number

BAT-011031

Molecular Formula

C129H191N33O37S6

Molecular Weight

2988.5

Specification
Reference Reading

IUPAC Name

3-[(1R,4S,7S,13S,16S,19R,22S,25S,28S,31S,34R,37S,40S,46R,49S,52S,55S,58S,61S,64R,67S,70S,76S,79S,82R,85S)-22,28,61-tris(4-aminobutyl)-25,31-dibenzyl-52-[(2S)-butan-2-yl]-4-(3-carbamimidamidopropyl)-13,37-bis[(1R)-1-hydroxyethyl]-49,58,79,85-tetrakis(hydroxymethyl)-16,76-bis[(4-hydroxyphenyl)methyl]-55-methyl-3,6,12,15,18,21,24,27,30,33,36,39,42,45,48,51,54,57,60,63,66,69,75,78,81,84,87-heptacosaoxo-67-propan-2-yl-89,90,93,94,97,98-hexathia-2,5,11,14,17,20,23,26,29,32,35,38,41,44,47,50,53,56,59,62,65,68,74,77,80,83,86-heptacosazahexacyclo[44.41.4.419,64.434,82.07,11.070,74]nonanonacontan-40-yl]propanoic acid

Synonyms

cyclo[Ala-Ile-Ser-Cys(1)-Gly-Glu-Thr-Cys(2)-Phe-Lys-Phe-Lys-Cys(3)-Tyr-Thr-Pro-Arg-Cys(1)-Ser-Cys(2)-Ser-Tyr-Pro-Val-Cys(3)-Lys-Ser]; SAISCGETCFKFKCYTPRCSCSYPVCK

Sequence

(cyclo)-AISC(1)GETC(2)FKFKC(3)YTPRC(1)SC(2)SYPVC(3)KS-(cyclo)

InChI

InChI=1S/C129H191N33O37S6/c1-8-66(4)100-125(196)150-88(58-166)116(187)151-89-59-200-201-61-91-120(191)149-87(57-165)115(186)154-92-62-203-205-64-94(156-126(197)101(68(6)167)159-109(180)80(42-43-98(172)173)138-97(171)54-136-104(89)175)119(190)144-82(51-71-26-13-10-14-27-71)111(182)139-76(28-15-18-44-130)105(176)143-81(50-70-24-11-9-12-25-70)110(181)140-78(30-17-20-46-132)107(178)152-90(118(189)145-83(52-72-34-38-74(169)39-35-72)112(183)160-102(69(7)168)128(199)162-49-23-32-95(162)122(193)142-79(108(179)153-91)31-21-47-135-129(133)134)60-202-204-63-93(117(188)141-77(29-16-19-45-131)106(177)147-85(55-163)113(184)137-67(5)103(174)158-100)155-124(195)99(65(2)3)157-123(194)96-33-22-48-161(96)127(198)84(53-73-36-40-75(170)41-37-73)146-114(185)86(56-164)148-121(92)192/h9-14,24-27,34-41,65-69,76-96,99-102,163-170H,8,15-23,28-33,42-64,130-132H2,1-7H3,(H,136,175)(H,137,184)(H,138,171)(H,139,182)(H,140,181)(H,141,188)(H,142,193)(H,143,176)(H,144,190)(H,145,189)(H,146,185)(H,147,177)(H,148,192)(H,149,191)(H,150,196)(H,151,187)(H,152,178)(H,153,179)(H,154,186)(H,155,195)(H,156,197)(H,157,194)(H,158,174)(H,159,180)(H,160,183)(H,172,173)(H4,133,134,135)/t66-,67-,68+,69+,76-,77-,78-,79-,80-,81-,82-,83-,84-,85-,86-,87-,88-,89-,90-,91-,92-,93-,94-,95-,96-,99-,100-,101-,102-/m0/s1

InChI Key

DIHQXZONSJVFJY-UPRQFWENSA-N

Canonical SMILES

CCC(C)C1C(=O)NC(C(=O)NC2CSSCC3C(=O)NC(C(=O)NC4CSSCC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(CSSCC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N1)C)CO)CCCCN)NC(=O)C(NC(=O)C5CCCN5C(=O)C(NC(=O)C(NC4=O)CO)CC6=CC=C(C=C6)O)C(C)C)C(=O)NC(C(=O)NC(C(=O)N7CCCC7C(=O)NC(C(=O)N3)CCCNC(=N)N)C(C)O)CC8=CC=C(C=C8)O)CCCCN)CC9=CC=CC=C9)CCCCN)CC1=CC=CC=C1)NC(=O)C(NC(=O)C(NC(=O)CNC2=O)CCC(=O)O)C(C)O)CO)CO

1. Violacin A, a new chromanone produced by Streptomyces violaceoruber and its anti-inflammatory activity

Jian Ma, Bixuan Cao, Xiu Chen, Minjuan Xu, Xiaoxu Bi, Peipei Guan, Yi Jiang, Jun Xu, Li Han, Xueshi Huang Bioorg Med Chem Lett. 2018 Mar 1;28(5):947-951. doi: 10.1016/j.bmcl.2018.01.051. Epub 2018 Jan 31.

A new chromanone derivative, named violacin A (1), was isolated from the fermentation broth of Streptomyces violaceoruber as a potential anti-inflammatory compound. The structure of violacin A was established using comprehensive NMR spectroscopic data analysis together with UV, IR, and MS data. The anti-inflammatory effects and action mechanisms of violacin A were investigated in vitro. The results demonstrated that violacin A attenuated the production of NO, IL-1β, IL-6, and TNF-α as well as inhibited the expression of iNOS in LPS-induced RAW 264.7 cells. Additionally, Western blot and qRT-PCR results revealed that 1 down-regulated pro-inflammatory cytokines expression correlated with the suppression of NF-κB signaling pathway.

2. Biomimetic synthesis and anti-inflammatory evaluation of violacin A analogues

Wenxi Wu, Yu Mu, Bo Liu, Zixuan Wang, Peipei Guan, Li Han, Mingguo Jiang, Xueshi Huang Bioorg Chem. 2021 Jun;111:104898. doi: 10.1016/j.bioorg.2021.104898. Epub 2021 Apr 8.

Violacin A, a chromanone derivative, isolated from a fermentation broth of Streptomyces violaceoruber, has excellent anti-inflammatory potential. Herein, a biogenetically modeled approach to synthesize violacin A and twenty-five analogues was described, which involved the preparation of aromatic polyketide precursor through Claisen condensation and its spontaneous cyclization. The inhibitory effect on nitric oxide (NO) production of all synthetic molecules was evaluated by lipopolysaccharide (LPS)-induced Raw264.7 cells. The results revealed that introduction of aliphatic amine moieties on C-7 obviously improved the anti-inflammation effect of violacin A, and also the aromatic ether instead of ketone group at side chain was favorable to increase the activity. Among them, analogue 7a and 16d were screened as the most effective anti-inflammatory candidates. Molecular mechanism research revealed that 7a and 16d acquired anti-inflammatory ability due to the inhibition of NF-κB signaling pathway.

3. Total synthesis and anti-inflammatory evaluation of violacin A and its analogues

Qingyin Liu, Yu Mu, Qi An, Jiali Xun, Jian Ma, Wenxi Wu, Minjuan Xu, Jun Xu, Li Han, Xueshi Huang Bioorg Chem. 2020 Jan;94:103420. doi: 10.1016/j.bioorg.2019.103420. Epub 2019 Nov 4.

A concise total synthesis of an exceedingly potent anti-inflammatory agent violacin A as well as the preparation of thirty analogues of this lead from commercially available orcinol are described. Highlights of our synthetic efforts involve Friedel-Crafts acylation, the regioselective etherification and esterification of phenolic hydroxyl groups, and Baker-Venkatamaran rearrangement to form basic skeleton of violacin A. The deprotection reaction with Pd-catalytic was involved to avoid the elimination of the hemiacetal hydroxyl at C2. In addition, all synthetic compounds were screened for anti-inflammatory activity against nitric oxide (NO) production using lipopolysaccharide (LPS)-induced Raw264.7 cells. A range of violacin A derivatives 11b, 11d, 11f, 12e, 12g, 13g, 17d-g exhibited stronger anti-inflammatory effect than that of violacin A. Notably, halogeno-benzyloxy substituent at C-7 were favourable for anti-inflammatory activities of violacin A derivatives. Additionally, Western blot results indicated halogeno-benzyloxy derivatives inhibited pro-inflammatory cytokines releases correlated with the suppression of NF-κB signaling pathway.