OPHIOBOLIN A

Product NameOPHIOBOLIN A
CAS4611-05-6
MFC25H36O4
MW400.55
EINECS
MOL File4611-05-6.mol

Chemical Properties

Melting point	182°C
Boiling point	443.19°C (rough estimate)
Density	1.0278 (rough estimate)
refractive index	1.4460 (estimate)
storage temp.	2-8°C
solubility	Soluble in DMSO (up to 10 mg/ml)
form	White to off-white solid.
pka	13.84±0.70(Predicted)
color	White
biological source	(from Biopolaris leersia fungal metabolite)
Stability	Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 2 months.
InChIKey	MWYYLZRWWNBROW-BDZRSQQBSA-N
SMILES	[H]C(/C1=C/C[C@]([C@]2(O[C@@H](C=C(C)C)C[C@@H]2C)CC3)([H])[C@@]3(C)C[C@@]([C@](C)(O)C4)([H])[C@]1([H])C4=O)=O

Safety Information

Hazard Codes	Xn
Risk Statements	20/21/22
Safety Statements	36
RIDADR	UN 2811 6.1/PG 3
WGK Germany	3
RTECS	RL1576000
HS Code	2932190090
Storage Class	6.1C - Combustible acute toxic Cat.3 toxic compounds or compounds which causing chronic effects
Hazard Classifications	Acute Tox. 3 Oral
Toxicity	mouse,LD50,intraperitoneal,21mg/kg (21mg/kg),"CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980Vol. 6, Pg. 143, 1981.

Usage And Synthesis

Description

Ophiobolin A (4611-05-6) selectively inhibits the growth of cancer cells (IC50=0.4-4.3 μM) over normal cells (IC50=20.9 μM).1 Induces non-apoptotic cell death in glioblastoma cells and is active in an in vivo model.2 Covalently reacts with primary amines such as lysine side chains2 and phosphatidylethanolamine3 forming unique pyrrole adducts. Induces ER stress4, paraptosis4 and autophagy5.

Uses

Ophiobolin A is the dominant member of a class of phytotoxic metabolites produced by plant pathogenic fungi. Ophiobolin A acts by inhibiting calmodulin action in calcium regulation.

Definition

ChEBI: A sesterterpenoid that is ophiobolane with a hydroxy group at position 3, oxo groups at positions 5 and 25, double bonds at positions 7-8 and 19-20, and an oxygen link between positions 14 and 18.

References

[1] DIMPLE R. BHATIA . Anticancer activity of Ophiobolin A, isolated from the endophytic fungus Bipolaris setariae[J]. Natural Product Research, 2016, 30 12: Pages 1455-1458. DOI:10.1080/14786419.2015.1062760
[2] RAMESH DASARI . Fungal metabolite ophiobolin A as a promising anti-glioma agent: In vivo evaluation, structure–activity relationship and unique pyrrolylation of primary amines[J]. Bioorganic & Medicinal Chemistry Letters, 2015, 25 20: Pages 4544-4548. DOI:10.1016/j.bmcl.2015.08.066
[3] CHRISTOPHER CHIDLEY. The anticancer natural product ophiobolin A induces cytotoxicity by covalent modification of phosphatidylethanolamine.[J]. eLife, 2016. DOI:10.7554/elife.14601
[4] IN YOUNG KIM. Ophiobolin A kills human glioblastoma cells by inducing endoplasmic reticulum stress via disruption of thiol proteostasis.[J]. Oncotarget, 2017, 8 63: 106740-106752. DOI:10.18632/oncotarget.22537
[5] C. RODOLFO. Ophiobolin A Induces Autophagy and Activates the Mitochondrial Pathway of Apoptosis in Human Melanoma Cells[J]. PLoS ONE, 2016, 11 1. DOI:10.1371/journal.pone.0167672

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