A bacterial metabolite with diverse biological activities
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Deoxyenterocin

Item No. 25764

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(3S,4aR,5S,6S,7S,7aS)-7-benzoylhexahydro-4a,6,7a-trihydroxy-5-(4-methoxy-2-oxo-2H-pyran-6-yl)-3,6-methanocyclopenta[c]pyran-1(3H)-one
CAS Number
108605-51-2
Synonyms
  • 5-Deoxyenterocin
Molecular Formula
C22H20O9
Formula Weight
428.4
Purity
≥99%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: solubleDMSO: solubleEthanol: solubleMethanol: soluble
SMILES
O=C1[C@@]2(O)[C@@]([C@@H](C(O3)=CC(OC)=CC3=O)[C@]4(O)[C@@H]2C(C5=CC=CC=C5)=O)(O)C[C@@](C4)([H])O1
InChi Code
InChI=1S/C22H20O9/c1-29-12-7-14(31-15(23)8-12)17-20(26)9-13-10-21(17,27)22(28,19(25)30-13)18(20)16(24)11-5-3-2-4-6-11/h2-8,13,17-18,26-28H,9-10H2,1H3/t13-,17-,18-,20-,21+,22+/m0/s1
InChi Key
UTKCEZMWSNDCMR-SAKMHLFVSA-N
Origin
Bacterium/Streptomyces sp.
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Deoxyenterocin is a bacterial metabolite originally isolated from Streptomyces that has diverse biological activities, including antibiotic, antiviral, and antioxidant properties.1 It inhibits the growth of S. lutea, S. aureus, K. pneumoniae, and V. percolans in vitro when used at a concentration of 500 μg/ml. Deoxyenterocin (50 μg/ml) inhibits the cytopathic effect of influenza A H1N1 virus by 60.6% in vitro.2 It also prevents hydrogen peroxide-induced decreases in glutathione (GSH) levels and in the mitochondrial membrane potential in mouse primary cortical neuronal cultures when used at a concentration of 1 μM.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Yaginuma, S., Asahi, T., Muto, N., et al. Novel antibiotic 5-deoxyenterocin production by Streptomyces species and its antimicrobiol activities. (1987).

    2. Liu, H., Chen, Z., Zhu, G., et al. Phenolic polyketides from the marine alga-derived Streptomyces sp. OUCMDZ-3434. Tetrahedron 73(36), 5451-5455 (2017).

    3. Leiros, M., Alonso, E., Sanchez, J.A., et al. Mitigation of ROS insults by Streptomyces secondary metabolites in primary cortical neurons. ACS Chem. Neurosci. 5(1), 71-80 (2014).