A fungus-derived calmodulin antagonist
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Ophiobolin B

Item No. 18432

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(1R,3aS,6aR,7S,9aR,10aS)-7-[(1S)-1,5-dimethyl-4-hexen-1-yl]-1,2,3,3a,6,6a,7,8,9,9a,10,10a-dodecahydro-1,7-dihydroxy-1,9a-dimethyl-3-oxo-dicyclopenta[a,d]cyclooctene-4-carboxaldehyde
CAS Number
5601-74-1
Synonyms
  • Cochliobolin B
  • Ophiobolsin A
  • Zizanin B
Molecular Formula
C25H38O4
Formula Weight
402.6
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: solubleDMSO: solubleEthanol: solubleMethanol: soluble
SMILES
C[C@@]12C[C@@]([H])([C@]3(/C(C=O)=C\C[C@]1([C@](O)(CC2)[C@H](CC/C=C(C)\C)C)[H])[H])[C@](CC3=O)(C)O
InChi Code
InChI=1S/C25H38O4/c1-16(2)7-6-8-17(3)25(29)12-11-23(4)13-19-22(20(27)14-24(19,5)28)18(15-26)9-10-21(23)25/h7,9,15,17,19,21-22,28-29H,6,8,10-14H2,1-5H3/b18-9-/t17-,19-,21+,22+,23+,24+,25-/m0/s1
InChi Key
SXRLPRKYTRWOES-PCQMDVLKSA-N
Origin
Fungus/Bipolaris leersia
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    Product Description

    Calmodulin is a calcium-sensing protein that regulates a wide array of proteins involved in diverse cellular functions. Ophiobolin B is a sesterterpenoid fungal phytotoxin that binds and irreversibly antagonizes calmodulin, producing cytotoxic and antimicrobial effects. It induces apoptosis in chronic lymphocytic leukemia cells with an LC50 value of 2 nM and in different zygomycetes with MIC values ranging from 25-50 µg/ml.1,2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Bladt, T.T., Dürr, C., Knudsen, P.B., et al. Bio-activity and dereplication-based discovery of ophiobolins and other fungal secondary metabolites targeting leukemia cells. Molecules 18(12), 14629-14650 (2013).

    2. Krizsán, K., Bencsik, O., Nyilasi, I., et al. Effect of the sesterterpene-type metabolites, ophiobolins A and B, on zygomycetes fungi. FEMS Microbiol Lett. 313(2), 135-140 (2010).