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AdipoGen Life Sciences
Ophiobolin A
150
CHF
CHF 150.00
In stock
AG-CN2-0431-C100100 µgCHF 150.00
AG-CN2-0431-M0011 mgCHF 450.00
| Product Details | |
|---|---|
| Synonyms | Cochliobolin A; Ophiobalin; NSC 114340 |
| Product Type | Chemical |
| Properties | |
| Formula |
C25H36O4 |
| MW | 400.6 |
| CAS | 4611-05-6 |
| RTECS | RL1576000 |
| Source/Host Chemicals | Isolated from Bipolaris leersia. |
| Purity Chemicals | ≥95% (HPLC) |
| Appearance | White solid. |
| Solubility | Soluble in ethanol, methanol, DMSO or dimethylformamide. Poorly soluble in water. |
| InChi Key | MWYYLZRWWNBROW-BDZRSQQBSA-N |
| Smiles | [H]C(=O)C1=C[C@]2([H])[C@](C)(CC[C@@]22O[C@H](C[C@@H]2C)C=C(C)C)C[C@@]2([H])[C@]1([H])C(=O)C[C@@]2(C)O |
| Shipping and Handling | |
| Shipping | AMBIENT |
| Short Term Storage | +4°C |
| Long Term Storage | -20°C |
| Handling Advice |
Keep under inert gas. Protect from light. Protect from light when in solution. |
| Use/Stability | Stable for at least 2 years after receipt when stored at -20°C. |
| Documents | |
| MSDS |
 Download PDF |
| Product Specification Sheet | |
| Datasheet |
Download PDF |
Description
- 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 [1-3, 5, 6, 9].
- Herbicidal mycotoxin [7].
- Phytotoxic, antifungal, antibacterial and nematocidal compound [4, 6, 10].
- Anticancer compound. Shown to induce paraptosis-like cell death [11, 12].
- Shown to inhibit P-glycoprotein-mediated transport [8].
- Disruptor of intracellular sulfhydryl proteostasis, leading to ER stress and dilation.
Product References
- Ophiobolin A. A natural product inhibitor of calmodulin: P.C. Leung, et al.; J. Biol. Chem. 259, 2742 (1984)
- Role of Calmodulin Inhibition in the Mode of Action of Ophiobolin A: P.C. Leung, et al.; Plant Physiol. 77, 303 (1985)
- Characterization of the interaction of ophiobolin A and calmodulin: P.C. Leung, et al.; Int. J. Biochem. 20, 1351 (1988)
- Microbial metabolites of ophiobolin A and antimicrobial evaluation of ophiobolins: E. Li, et al.; J. Nat. Prod. 58, 74 (1995)
- 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)
- The biology of ophiobolins: T.K. Au, et al.; Life Sci. 67, 733 (2000) (Review)
- Herbicidal potential of ophiobolins produced by Drechslera gigantea: A. Evidente, et al.; J. Agric. Food Chem. 54, 1779 (2006)
- 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)
- Calcium depletion and calmodulin inhibition affect the import of nuclear-encoded proteins into plant mitochondria: S. Kuhn, et al.; Plant J. 58, 694 (2009)
- Effect of the sesterterpene-type metabolites, ophiobolins A and B, on zygomycetes fungi: K. Krizsan, et al.; FEMS Microbiol. Lett. 313, 135 (2010)
- 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)
- 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)
- Ophiobolin A kills human glioblastoma cells by inducing endoplasmic reticulum stress via disruption of thiol proteostasis: I.Y. Kim, et al.; Oncotarget 8, 106740 (2017)
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