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207314 Ophiobolin A (Cochliobolin A, Ophiobalin, NSC 114340) CAS: 4611-05-6

Specifications
References
CAS Number
4611-05-6
Grade
Highly Purified
Molecular Formula
C25H36O4
Molecular Weight
400.6
EU Commodity Code
38220090
Shipping Temp
Blue Ice
Storage Temp
-20°C

Cell permeable, irreversible calmodulin antagonist. Acts by covalently binding to a lysine-rich inhibitory site. Inhibits by blocking the activation of the Ca2+/calmodulin-dependent phosphodiesterase. Herbicidal mycotoxin. Phytotoxic, antifungal, antibacterial and nematocidal compound. Anticancer compound. Shown to induce paraptosis-like cell death. Shown to inhibit P-glycoprotein-mediated transport.

Source
Bipolaris leersia
Formula
C25H36O4
Solubility
Soluble in ethanol, methanol, DMSO or dimethylformamide. Poorly soluble in H2O.
Molecular Weight
~400.6
Storage and Stability
Lyophilized powder may be stored at -20°C. Stable for 12 months after receipt at -20°C. Reconstitute with ethanol, methanol, DMSO or dimethylformamide. Aliquot to avoid repeated freezing and thawing. Store at -20°C. Reconstituted product is stable for 6 months at -20°C. For maximum recovery of product, centrifuge the original vial after thawing and prior to removing the cap. Further dilutions can be made in assay buffer.
Source
Bipolaris leersia
Purity
~95% (HPLC)
Concentration
Not determined
Form
Supplied as a white solid.
Important Note
This product as supplied is intended for research use only, not for use in human, therapeutic or diagnostic applications without the expressed written authorization of United States Biological.
References
1. Ophiobolin A. A natural product inhibitor of calmodulin: P.C. Leung, et al.; J. Biol. Chem. 259: 2742 (1984). 2. Role of Calmodulin Inhibition in the Mode of Action of Ophiobolin A: P.C. Leung, et al.; Plant Physiol. 77: 303 (1985). 3. Characterization of the interaction of ophiobolin A and calmodulin: P.C. Leung, et al.; Int. J. Biochem. 20: 1351 (1988) 4. Microbial metabolites of ophiobolin A and antimicrobial evaluation of ophiobolins: E. Li, et al.; J. Nat. Prod. 58: 74 (1995). 5. Identification of the binding and inhibition sites in the calmodulin molecule for ophiobolin A by site-directed mutagenesis: T. Kong Au & P. Chow Leung; Plant Physiol. 118: 965 (1998). 6. The biology of ophiobolins: T.K. Au, et al.; Life Sci. 67: 733 (2000) (Review) 7. Herbicidal potential of ophiobolins produced by Drechslera gigantea: A. Evidente, et al.; J. Agric. Food Chem. 54: 1779 (2006) 8. Inhibition of P-glycoprotein-mediated transport by terpenoids contained in herbal medicines and natural products: N. Yoshida, et al.; Food Chem. Toxicol. 44: 2033 (2006) 9. Calcium depletion and calmodulin inhibition affect the import of nuclear-encoded proteins into plant mitochondria: S. Kuhn, et al.; Plant J. 58: 694 (2009) 10. Effect of the sesterterpene-type metabolites, ophiobolins A and B, on zygomycetes fungi: K. Krizsan, et al.; FEMS Microbiol. Lett. 313: 135 (2010) 11. Ophiobolin A induces paraptosis-like cell death in human glioblastoma cells by decreasing BKCa channel activity: M. Bury, et al.; Cell Death Dis. 4: e561 (2013). 12. Ophiobolin A, a sesterterpenoid fungal phytotoxin, displays higher in vitro growth-inhibitory effects in mammalian than in plant cells and displays in vivo antitumor activity: M. Bury, et al.; Int. J. Oncol. 43: 575 (2013)
USBio References
No references available
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