Maculosin

Maculosin (Cyclo (Tyr-Pro) ) is a host-specific phytotoxin for spotted knapweed from Alternaria alternata. Maculosin is a quorum-sensing molecule involved in cell-cell communication. Maculosin also acts as a signaling molecule regulating virulence gene expression. Maculosin shows antimicrobial, antifungal, antioxidant and anti-cancer properties[1][2][3][4][5][6][7][8][9].Maculosin (Cyclo (Tyr-Pro) ) is a host-specific phytotoxin for spotted knapweed from Alternaria alternata. Maculosin is a quorum-sensing molecule involved in cell-cell communication. Maculosin also acts as a signaling molecule regulating virulence gene expression. Maculosin shows antimicrobial, antifungal, antioxidant and anti-cancer properties[1][2][3][4][5][6][7][8][9].

Product Specifications

CAS Number

[4549-02-4]

Product Name Alternative

Cyclo (Tyr-Pro)

UNSPSC

12352209

Hazard Statement

H301, H311, H331, H371

Target

Bacterial; Endogenous Metabolite; Fungal

Type

Peptides

Related Pathways

Anti-infection; Metabolic Enzyme/Protease

Applications

Cancer-programmed cell death

Field of Research

Cancer; Infection

Assay Protocol

https://www.medchemexpress.com/maculosin.html

Purity

99.06

Solubility

DMSO : 100 mg/mL (ultrasonic)

Smiles

OC1=CC=C(C=C1)C[C@@H]2NC([C@]3([H])CCCN3C2=O)=O

Molecular Formula

C14H16N2O3

Molecular Weight

260.29

Precautions

H301, H311, H331, H371

References & Citations

[1]Lee W, et al. Vibrio vulnificus quorum-sensing molecule cyclo (Phe-Pro) inhibits RIG-I-mediated antiviral innate immunity. Nat Commun. 2018 Apr 23;9 (1) :1606.|[2]Stierle AC, et al. Maculosin, a host-specific phytotoxin for spotted knapweed from Alternaria alternata. Proc Natl Acad Sci U S A. 1988 Nov;85 (21) :8008-11.|[3]Paudel B, et al. Maculosin, a non-toxic antioxidant compound isolated from Streptomyces sp. KTM18. Pharm Biol. 2021 Dec;59 (1) :933-936. |[4]Puopolo G, et al. Lysobacter capsici AZ78 produces cyclo (L-Pro-L-Tyr), a 2,5-diketopiperazine with toxic activity against sporangia of Phytophthora infestans and Plasmopara viticola. J Appl Microbiol. 2014 Oct;117 (4) :1168-80.|[5]Wattana-Amorn P, et al. Antibacterial activity of cyclo (L-Pro-L-Tyr) and cyclo (D-Pro-L-Tyr) from Streptomyces sp. strain 22-4 against phytopathogenic bacteria. Nat Prod Res. 2016 Sep;30 (17) :1980-3. |[6]Cain CC, et al. Synergistic antimicrobial activity of metabolites produced by a nonobligate bacterial predator. Antimicrob Agents Chemother. 2003 Jul;47 (7) :2113-7.|[7]Driche EH, et al. A New Saharan Strain of Streptomyces sp. GSB-11 Produces Maculosin and N-acetyltyramine Active Against Multidrug-Resistant Pathogenic Bacteria. Curr Microbiol. 2022 Aug 24;79 (10) :298.|[8]Wang X, et al. Analysis of the Antioxidant Composition of Low Molecular Weight Metabolites from the Agarolytic Bacterium Alteromonas macleodii QZ9-9: Possibilities for High-Added Value Utilization of Macroalgae. Antioxidants (Basel) . 2022 Oct 3;11 (10) :1977.|[9]Wang Y, et al. Developments around the bioactive diketopiperazines: a patent review. Expert Opin Ther Pat. 2013 Nov;23 (11) :1415-33.