ophiobolin C

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 an inhibitor of human CCR5 binding to HIV-1 gp120.

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.

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

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