Maculosin

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.Formal Name: (3S,8aS)-hexahydro-3-[(4-hydroxyphenyl)methyl]-pyrrolo[1,2-a]pyrazine-1,4-dione. CAS Number: 4549-02-4. Synonyms: Cyclo(L-Pro-L-Tyr). Molecular Formula: C14H16N2O3. Formula Weight: 260.3. Purity: >95%. Formulation: (Request formulation change), A solid. Solubility: DMF: soluble, DMSO: soluble, Ethanol: soluble, Methanol: soluble. SMILES: OC1=CC=C(C[C@@H]2NC([C@@](CCC3)([H])N3C2=O)=O)C=C1. InChi Code: InChI=1S/C14H16N2O3/c17-10-5-3-9(4-6-10)8-11-14(19)16-7-1-2-12(16)13(18)15-11/h3-6,11-12,17H,1-2,7-8H2,(H,15,18)/t11-,12-/m0/s1. InChi Key: LSGOTAXPWMCUCK-RYUDHWBXSA-N.