An alkaloid with diverse biological activities
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Brevianamide F

Item No. 23493

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(3S,8aS)-hexahydro-3-(1H-indol-3-ylmethyl)-pyrrolo[1,2-a]pyrazine-1,4-dione
CAS Number
38136-70-8
Synonyms
  • cyclo-(L-Trp-L-Pro)
  • Cyclo-L-tryptophyl-L-proline
Molecular Formula
C16H17N3O2
Formula Weight
283.3
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 33 mg/mlDMSO: 33 mg/mlDMSO:PBS(pH 7.2) (1:3): 0.25 mg/mlEthanol: 1 mg/ml
SMILES
O=C([C@@]1([H])N2CCC1)N[C@@H](CC3=CNC4=C3C=CC=C4)C2=O
InChi Code
InChI=1S/C16H17N3O2/c20-15-14-6-3-7-19(14)16(21)13(18-15)8-10-9-17-12-5-2-1-4-11(10)12/h1-2,4-5,9,13-14,17H,3,6-8H2,(H,18,20)/t13-,14-/m0/s1
InChi Key
RYFZBPVMVYTEKZ-KBPBESRZSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

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    Product Description

    Brevianamide F is an alkaloid metabolite produced by various Streptomyces, Actinomycetes, and Aspergillus strains that has diverse biological activities.1,2,3 It inhibits growth of M. luteus and S. aureus in an inhibitory disc assay when used at a concentration of 30 μg/disc as well as the Bacille Calmette-Guerin M. bovis strain (MIC = 12.5 μg/ml).2,3 Brevianamide F has antifouling activity, inhibiting attachment of B. neritina larvae to PVC plates without inducing lethality (EC50 = 6.35 μg/ml; LC50 = >200 μg/ml in paint used to coat PVC plates).1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Zhang, X.-Y., Xu, X.-Y., Peng, J., et al. Antifouling potentials of eight deep-sea-derived fungi from the South China Sea. J. Ind. Microbiol. Biotechnol. 41(4), 741-748 (2014).

    2. Ben Ameur Mehdi, R., Shaaban, K.A., Rebai, I.K., et al. Five naturally bioactive molecules including two rhamnopyranoside derivatives isolated from the Streptomyces sp. strain TN58. Nat. Prod. Res. 23(12), 1095-1107 (2009).

    3. Huang, P., Xie, F., Ren, B., et al. Anti-MRSA and anti-TB metabolites from marine-derived Verrucosispora sp. MS100047. Appl. Microbiol. Biotechnol. 100(17), 7437-7447 (2016).