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Maculosin

MCE China：Maculosin

Brand：MedChemExpress (MCE)

Cat. No.HY-P1940

CAS：4549-02-4

Synonyms：Cyclo(Tyr-Pro)

Purity：99.59%

Storage：Sealed storage, away from moisture and light, under nitrogen Powder -80°C 2 years -20°C 1 year *In solvent : -80°C, 6 months; -20°C, 1 month (sealed storage, away from moisture and light, under nitrogen)

Shipping：Room temperature in continental US; may vary elsewhere.

Description：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.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.

In Vitro：Maculosin shows cytotoxic activity against the human liver cancer cell lines, with an IC50 of 48.90 µg/mL[3]. Maculosin (0-128 μg/mL) shows stronger antioxidant activity than the commercially used Butylated hydroxyanisole (BHA) (HY-B1066), with IC50s of 2.16 and 4.8 µg/mL[3]. Maculosin (0-128 μg/mL, 24 h) shows no toxicity (LD50, [3]. Maculosin (10-100 μg/mL) reduces the growth of the plant pathogenic bacteria X. axonopodis and R. solanacearum (MICs = 31.25 μg/mL) as well as the pathogenic oomycetes P. cactorum, P. capsici, P. cinnamomi, P. infestans, and P. ultimum[4][5]. Maculosin inhibits the growth of M. luteus, M. smegmatis, S. cerevisiae, C. albicans, C. neoformans, and A. niger when used in combination with Pyrrolnitrin (HY-133704) or Banegasin[6]. Maculosin (0.5-100 μg/mL) shows antibacterial activity against certain multidrug-resistant pathogenic bacteria, with MICs of 5-15 mg/mL[7]. Maculosin shows specific antioxidant activity, with the DPPH scavenging activities of 38.22% at 7.5 μg/mL[8]. Maculosin (10 μM-1 mM) exhibits lesion inductive abilities when applied to knapweed leaves and hypocotyls[9].

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References：

[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.  [Content Brief]

[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.  [Content Brief]

[3]. Paudel B, et al. Maculosin, a non-toxic antioxidant compound isolated from Streptomyces sp. KTM18. Pharm Biol. 2021 Dec;59(1):933-936.  [Content Brief]

[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.  [Content Brief]

[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.  [Content Brief]

[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.  [Content Brief]

[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.  [Content Brief]

[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.  [Content Brief]

[9]. Wang Y, et al. Developments around the bioactive diketopiperazines: a patent review. Expert Opin Ther Pat. 2013 Nov;23(11):1415-33.  [Content Brief]