A bacterial metabolite with diverse biological activities
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Benastatin B

Item No. 32893

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5,6,8,13-tetrahydro-1,7,9,11-tetrahydroxy-13,13-dimethyl-8-oxo-3-pentyl-benzo[a]naphthacene-2-carboxylic acid
CAS Number
138968-86-2
Molecular Formula
C30H30O7
Formula Weight
502.6
Purity
≥90%
Formulation
A solid
SMILES
O=C(C1=C(CCCCC)C=C(CCC2=C(C3=C(C=C24)C(C)(C)C5=C(C(O)=CC(O)=C5)C3=O)O)C4=C1O)O
InChi Code
InChI=1S/C30H30O7/c1-4-5-6-7-14-10-15-8-9-17-18(22(15)27(34)23(14)29(36)37)13-20-25(26(17)33)28(35)24-19(30(20,2)3)11-16(31)12-21(24)32/h10-13,31-34H,4-9H2,1-3H3,(H,36,37)
InChi Key
FUKMCLKFEWEFSC-UHFFFAOYSA-N
Origin
Bacterium/Streptomyces sp.
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    1 mg

    $623

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    Product Description

    Benastatin B is a polyketide synthase-derived benastatin that has been found in Streptomyces and has diverse biological activities.1,2,3 It inhibits glutathione S-transferase (GST; Ki = 3.7 µM for the rat liver enzyme).2 Benastatin B also inhibits the transglycosylase activity of A. baumannii, C. difficile, E. coli, and S. aureus recombinant penicillin-binding proteins (PBPs; IC50s = 16, 53.3, 30.7, and 31.6 µM, respectively).3 It is active against several bacteria, including methicillin-resistant S. aureus (MRSA; MIC = 3.12 µg/ml).2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Xu, Z., Schenk, A., and Hertweck, C. Molecular analysis of the benastatin biosynthetic pathway and genetic engineering of altered fatty acid-polyketide hybrids. J. Am. Chem. Soc. 129(18), 6022-6030 (2007).

    2. Aoyagi, T., Aoyama, T., Kojima, F., et al. Benastatins A and B, new inhibitors of glutathione S-transferase, produced by Streptomyces sp. MI384-DF12. I. Taxonomy, production, isolation, physico-chemical properties and biological activities. J. Antibiot. (Tokyo) 45(9), 1385-1390 (1992).

    3. Wu, W.-S., Cheng, W.-C., Cheng, T.-J.R., et al. Affinity-based screen for inhibitors of bacterial transglycosylase. Am. Chem. Soc. 140(8), 2752-2755 (2018).