| Identification | Back Directory | [Name]
MACULOSIN | [CAS]
4549-02-4 | [Synonyms]
A-19C
MACULOSIN
ML-1532II
CYCLO(-PRO-TYR)
Antibiotic A-19C
cyclo(L-Pro-L-Tyr)
Cyclo(L-Tyr-L-Pro-)
MACULOSIN USP/EP/BP
Antibiotic ML-1532II
Cyclo(L-prolinyl-L-tyrosine)
(3S,8aS)-Hexahydro-3-[(4-hydroxyphenyl)methyl]pyrrolo[1,2-a]pyrazine-1,4-dione
Pyrrolo[1,2-a]pyrazine-1,4-dione, hexahydro-3-[(4-hydroxyphenyl)methyl]-, (3S,8aS)-
(3S,8aS)-3-(4-hydroxybenzyl)-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-quinone
(3S,8aS)-3-[(4-hydroxyphenyl)methyl]-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione | [Molecular Formula]
C14H16N2O3 | [MDL Number]
MFCD03093467 | [MOL File]
4549-02-4.mol | [Molecular Weight]
260.29 |
| Chemical Properties | Back Directory | [Melting point ]
156-159 °C | [Boiling point ]
581.4±43.0 °C(Predicted) | [density ]
1.36±0.1 g/cm3(Predicted) | [storage temp. ]
-15°C
| [solubility ]
DMF: soluble; DMSO: soluble; Ethanol: soluble; Methanol: soluble | [form ]
A solid | [pka]
9.92±0.15(Predicted) |
| Hazard Information | Back Directory | [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. |
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