A diketopiperazine metabolite
Technical Support & Resources

Information provided in the product description is from published literature. Due to the nature of scientific experimentation, your results (e.g., selectivity and effective concentrations) or specific application for this product may differ. If you have questions about how this product fits your application, please contact our technical support staff.

Visit our FAQ

Contact Us

Toll Free Phone (USA and Canada Only): (888) 526-5351
Direct Phone: (734) 975-3888

Request Technical Support

Technical Support Request

To streamline the process attach the appropriate questionnaire to your inquiry.

Download IHC QuestionnaireDownload WB Questionnaire

View Our Privacy Statement for details on how we use and protect your data. In addition, this site is protected by hCaptcha and its Privacy Policy and Terms of Service apply.

Maculosin

Item No. 25019

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
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(Learn about Variance in Solubility)
DMF: solubleDMSO: solubleEthanol: solubleMethanol: 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
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Recommended Products

Certificates of Analysis & Batch Specific Data

Provide batch numbers separated by commas to download or request available product inserts, QC sheets, certificates of analysis, data packs, and GC-MS data.

Download most recent Certificate of Analysis for this product

    5 mg

    $143

    Add

    25 mg

    $458

    Add
    Cayman Chemical
    Neutrophil Biology Wall Poster

    Explore how neutrophils shape the immune response in health and disease. This poster highlights neutrophil pathogen defense mechanisms, including phagocytosis, degranulation, and NETosis, as well as neutrophil roles in inflammation and NET-associated pathologies.

    DOWNLOAD NOW
    Product Description

    Maculosin is a diketopiperazine metabolite produced by A. alternata, L. capsici, Streptomyces, and the Gram-negative, nonobligate predator bacterial strain 679-2.1,2,3,4 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.1 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.2,3 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.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    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. USA 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).