| Identification | Back Directory | [Name]
ophiobolin C | [CAS]
19022-51-6 | [Synonyms]
Zizanin A
ophiobolin C
3-Hydroxy-5-oxoophiobola-7,19-dien-25-al
Dicyclopenta[a,d]cyclooctene-4-carboxaldehyde, 7-[(1S)-1,5-dimethyl-4-hexen-1-yl]-1,2,3,3a,6,6a,7,8,9,9a,10,10a-dodecahydro-1-hydroxy-1,9a-dimethyl-3-oxo-, (1R,3aS,6aS,7R,9aR,10aS)- | [Molecular Formula]
C25H38O3 | [MDL Number]
MFCD09752745 | [MOL File]
19022-51-6.mol | [Molecular Weight]
386.57 |
| Hazard Information | Back Directory | [Description]
Ophiobolin C is a sesterterpenoid fungal phytoxin produced by many species of the genus Bipolaris. It has been identified as an antagonist of chemokine receptor CCR5 binding (IC50 = 40 μM) to the envelope protein gp120 and to CD4, which is known to mediate HIV-1 viral entry into cells. Ophiobolin C is also reported to be cytotoxic to chronic lymphocytic leukemia cells (LC50 = 8 nM). | [Uses]
Ophiobolin C is a member of the ophiobolin class of phytotoxic metabolites produced by many species of the genus Bipolaris. Ophiobolin C inhibits human CCR5 binding to the envelope protein gp120 and CD4 that mediates HIV-1 entry into cells. Blockade of this binding was considered by scientists at Merck as a potential new mode of action for the treatment of HIV-1 infection. | [Uses]
Ophiobolin C is an inhibitor of human CCR5 binding to HIV-1 gp120. | [Definition]
ChEBI: Ophiobolin C is a sesterterpenoid that is ophiobolane with a hydroxy group at position 3, oxo group at positions 5, formyl group at position 7, and double bonds at positions 7-8 and 19-20. It has a role as an antineoplastic agent, an apoptosis inducer, an Aspergillus metabolite, a chemokine receptor 5 antagonist, a nematicide and a fungal metabolite. It is a cyclic ketone, an enal, a sesterterpenoid, a tertiary alcohol, a carbotricyclic compound and an olefinic compound. It derives from a hydride of an ophiobolane. | [IC 50]
CCR5; HIV-1 | [storage]
Store at -20°C | [References]
[1] HIRANTHI JAYASURIYA. Isolation and Structure of Antagonists of Chemokine Receptor (CCR5)[J]. Journal of Natural Products , 2004, 67 6: 1036-1038. DOI: 10.1021/np049974l
[2] TANJA THORSKOV BLADT. Bio-activity and dereplication-based discovery of ophiobolins and other fungal secondary metabolites targeting leukemia cells.[J]. Molecules, 2013, 18 12: 14629-14650. DOI: 10.3390/molecules181214629 |
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