An amicoumacin with quorum-sensing inhibitory activity
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Amicoumacin B

Item No. 31777

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3-amino-2,3,6-trideoxy-6-[[(1S)-1-[(3S)-3,4-dihydro-8-hydroxy-1-oxo-1H-2-benzopyran-3-yl]-3-methylbutyl]amino]-6-oxo-D-ribo-hexonic acid
CAS Number
77674-99-8
Synonyms
  • Compound 5195A
Molecular Formula
C20H28N2O8
Formula Weight
424.4
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: solubleMethanol: soluble
SMILES
O=C1C2=C(O)C=CC=C2C[C@@](O1)([H])[C@H](CC(C)C)NC([C@@H](O)[C@@H](O)[C@@H](N)CC(O)=O)=O
InChi Code
InChI=1S/C20H28N2O8/c1-9(2)6-12(22-19(28)18(27)17(26)11(21)8-15(24)25)14-7-10-4-3-5-13(23)16(10)20(29)30-14/h3-5,9,11-12,14,17-18,23,26-27H,6-8,21H2,1-2H3,(H,22,28)(H,24,25)/t11-,12-,14-,17-,18-/m0/s1
InChi Key
LOXFXXGTOVWWQV-YKRRISCLSA-N
Origin
Bacterium/Nocardia sp.
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

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    Product Description

    Amicoumacin B is an amicoumacin that has been found in N. jinanensis and has quorum-sensing inhibitory activity.1 It is active against C. violaceum (MIC = 250 µg/ml) and reduces the expression of the C. violaceum operons vioA, vioB, vioD, and vioE, but increases the expression of vioC, indicating quorum sensing inhibitory activity.2 Amicoumacin B increases the expression of bone morphogenetic protein 2 (BMP2) in MG-63 cells.1,3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Sun, W., Zhang, Y.-Q., Huang, Y., et al. Nocardia jinanensis sp. nov., an amicoumacin B-producing actinomycete. Int. J. Syst. Evol. Microbiol. 59(Pt 2), 417-420 (2009).

    2. Shi, W.-P., Zeng, H., Wan, C.-X., et al. Amicoumacins from a desert bacterium: quorum sensing inhibitor against Chromobacterium violaceum. Nat. Prod. Res. (2020).

    3. Zhao-Yong, Y., Zhi-Fei, Z., Xiao-Bo, H., et al. Study on the effect of amicoumacin B on up-regulating bmp-2 transcription and expression in MG63 cells. Chin. J. Antibiot. 33(4), 203-205 (2008).