LKT Labs

Biochemicals for Life Science Research

Ophiobolin A

Ophiobolin A

Product ID O610291
Cas No. 4611-05-6
Purity ≥98%
Product Unit SizeCostQuantityStock
1 mg $236.30 In stock
5 mg $887.10 In stock
10 mg $1,502.30 In stock
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Description

Ophiobolin A (Cochliobolin A) is a tetracyclic sesterterpenoid phytotoxin isolated from cochliobolus heterostrophus. This phytotoxin displays growth-inhibitory effects both in plants cells and in mammalian cells. Ophiobolin A was found to have anti-tumor effect in the B16F10 mouse melanoma model with lung pseudometastases.

Ophiobiolin A induces paraptosis-like cell death in human glioblastoma cells by decreasing BKCa channel activity.

In addition, ophiobolin A’s anti-cancer activity is attributed to its covalent modification of phosphatidylethanolamine in human cancer cells as well as its ability to activate mitochondrial pathway of apoptosis in tumor cells.

Product Info

Cas No.

4611-05-6
Purity

≥98%
Formula

C25H36O4
Formula Wt.

400.56
Chemical Name

(7E,18R)-3-Hydroxy-5-oxo-14,18-epoxyophiobola-7,19-dien-25-al

IUPAC Name

(7E,18R)-3-Hydroxy-5-oxo-14,18-epoxyophiobola-7,19-dien-25-al

Synonym

Cochiobolin A, NSC 114340, Cochliobolin, Ophiobolin, CHEBI:7777.
Melting Point

171-180°C
Appearance

White powder

Shipping and Storage

Store Temp

-20°C
Ship Temp

Ambient

Downloads

MSDS

O610291 MSDS PDF
Info Sheet

O610291 Info Sheet PDF

References

Bury M, Novo-Uzal E, Andolfi A, et al. 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. Int J Oncol. 2013; 43(2):575-85. PMID: 23754298.

Bury M, Girault A, Mégalizzi V, et al. Ophiobolin A induces paraptosis-like cell death in human glioblastoma cells by decreasing BKCa channel activity. Cell Death Dis. 2013, 28;4:e561. PMID: 23538442

Dasari R, Masi M, Lisy R, et al. Fungal metabolite ophiobolin A as a promising anti-glioma agent: In vivo evaluation, structure-activity relationship and unique pyrrolylation of primary amines. Bioorg Med Chem Lett. 2015, 25(20):4544-8. PMID: 26341136,

Chidley C, Trauger SA, Birsoy K, O'Shea EK. The anticancer natural product ophiobolin A induces cytotoxicity by covalent modification of phosphatidylethanolamine. Elife. 2016;5. pii: e14601. PMID: 27403889.

Rodolfo C, Rocco M, Cattaneo L, Ophiobolin A Induces Autophagy and Activates the Mitochondrial Pathway of Apoptosis in Human Melanoma Cells. PLoS One. 2016;11(12):e0167672. PMID: 27936075

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