WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 559349
CAS#: 4549-02-4
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.
MedKoo Cat#: 559349
Name: Maculosin
CAS#: 4549-02-4
Chemical Formula: C14H16N2O3
Exact Mass: 260.1161
Molecular Weight: 260.29
Elemental Analysis: C, 64.60; H, 6.20; N, 10.76; O, 18.44
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Synonym: Maculosin; Cyclo(L-pro-L-tyr)
IUPAC/Chemical Name: Pyrrolo(1,2-a)pyrazine-1,4-dione, hexahydro-3-((4-hydroxyphenyl)methyl)-, (3S,8aS)-
InChi Key: LSGOTAXPWMCUCK-RYUDHWBXSA-N
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
SMILES Code: Oc1ccc(C[C@@H]2NC(=O)[C@@H]3CCCN3C2=O)cc1
Appearance: Solid powder
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: To be determined
Shelf Life: >2 years if stored properly
Drug Formulation: To be determined
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
The following data is based on the product molecular weight 260.29 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 1.15 mL | 5.76 mL | 11.51 mL |
| 5 mM | 0.23 mL | 1.15 mL | 2.3 mL |
| 10 mM | 0.12 mL | 0.58 mL | 1.15 mL |
| 50 mM | 0.02 mL | 0.12 mL | 0.23 mL |
1. Stierle, A.C., Cardellina, J.H., and Strobel, G.A. Maculosin, a host-specific phytotoxin for spotted knapweed from Alternaria alternata. Proc. Natl. Acad. Sci. U.S.A. 85(21), 8008-8011 (1988).
2. Puopolo, G., Cimmino, A., Palmieri, M.C., 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. 117(4), 1168-1180 (2014).
3. Wattana-Amorn, P., Charoenwongsa, W., Williams, C., 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. 30(17), 1980-1983 (2016).
4. Cain, C.C., Lee, D., Waldo, R.H., III, et al. Synergistic antimicrobial activity of metabolites produced by a nonobligate bacterial predator. Antimicrob. Agents Chemother. 47(7), 2113-2117 (2003).
