Description
Maculosin is a diketopiperazine metabolite produced by
A. alternata, L. capsici, Streptomyces, and the Gram-negative, nonobligate predator bacterial strain 679-2. It acts as a host-specific phytotoxin, inducing formation of weeping necrotic lesions in leaves of spotted knapweed (
C. maculosa) when used at a concentration of 10 μM. Maculosin 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 when used at concentrations ranging from 10 to 100 mg/ml. Maculosin also inhibits the growth of
M. luteus, M. smegmatis, S. cerevisiae, C. albicans, C. neoformans, and
A. niger when used in combination with pyrrolnitrin or banegasin.
Uses
Cyclo(L-prolinyl-L-tyrosine) is a diketopiperazine derivative isolated from Bacillus thuringiensis and Bacillus endophyticus.
Uses
Cyclo(L-Pro-L-Tyr) (maculosin) is a diketopiperazine formed by the fusion of tyrosine and proline, reported as a secondary metabolite of fungi and bacteria. In Pseudomonas aeruginosa, cyclo(L-Pro-L-Tyr) is capable of activating N-acylhomoserine lactones (AHLs). Cyclo(L-Pro-L-Tyr) is also capable of activating or antagonizing other LuxR-based quorum-sensing systems. While the mode of action of cyclo(L-Pro-L-Tyr) is not known, its activity suggests the existence of cross talk among bacterial signalling systems. Cyclo(L-Pro-L-Tyr) was identified as a host-specific toxin produced by Alternaria alternata on spotted knapweed.
Definition
ChEBI: A homodetic cyclic peptide that is a dipeptide composed of L-proline and L-tyrosine joined by peptide linkages.
References
[1] A C STIERLE G A S J H Cardellina. Maculosin, a host-specific phytotoxin for spotted knapweed from Alternaria alternata.[J]. Proceedings of the National Academy of Sciences of the United States of America, 1988: 8008-8011. DOI:
10.1073/pnas.85.21.8008[2] G. PUOPOLO. 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]. Journal of Applied Microbiology, 2014, 117 4: 1168-1180. DOI:
10.1111/jam.12611[3] PAKORN WATTANA-AMORN . Antibacterial activity of cyclo(L-Pro-L-Tyr) and cyclo(D-Pro-L-Tyr) from Streptomyces sp. strain 22-4 against phytopathogenic bacteria[J]. Natural Product Research, 2016, 30 17: Pages 1980-1983. DOI:
10.1080/14786419.2015.1095747[4] CODY C CAIN. Synergistic antimicrobial activity of metabolites produced by a nonobligate bacterial predator.[J]. Antimicrobial Agents and Chemotherapy, 2003, 47 7: 2113-2117. DOI:
10.1128/aac.47.7.2113-2117.2003
