4611-05-6

Basic information

• Product Name: OPHIOBOLIN A
• Synonyms: 18-epoxy-3-hydroxy-5-oxo-19-dien-25-a(18r)-ophiobola-14;cochliobolin;ophiobolin;COCHLIOBOLIN A;ophiobolin A from helminthosporium sp.;Ophiobolin, Helminthosporium sp.;(18R)-14,18-Epoxy-3-hydroxy-5-oxoophiobola-7,19-dien-25-al;(18R)-3-Hydroxy-5-oxo-14,18-epoxyophiobola-7,19-diene-25-al
• CAS NO: 4611-05-6
• Molecular Formula: C₂₅H₃₆O₄
• Molecular Weight: 400.55
• Mol File: 4611-05-6.mol
• Article Data: 2

Chemical Properties

• Melting Point: 182°C
• Boiling Point: 443.19°C (rough estimate)
• Flash Point: 177.8°C
• Appearance: /
• Density: 1.0278 (rough estimate)
• Vapor Pressure: 6.91E-14mmHg at 25°C
• Refractive Index: 1.4460 (estimate)
• Storage Temp.: 2-8°C
• Solubility: Soluble in DMSO (up to 10 mg/ml)
• PKA: 13.84±0.70(Predicted)
• 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.
• CAS DataBase Reference: OPHIOBOLIN A(CAS DataBase Reference)
• NIST Chemistry Reference: OPHIOBOLIN A(4611-05-6)
• EPA Substance Registry System: OPHIOBOLIN A(4611-05-6)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• RTECS: RL1576000
• Hazardous Substances Data: 4611-05-6(Hazardous Substances Data)

Usage

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) Bhatia et al. (2016), Anticancer activity of Ophiobolin A, isolated from the endophytic fungus Bipolaris setariae; Nat. Prod. Res., 30 1455 2) Dasari et al. (2015), 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., 25 4544 3) Chidley et al. (2016), The anticancer natural product ophiobolin A induces cytotoxicity by covalent modification of phosphatidylethanolamine; Elife., 5 e14601 4) Kim et al. (2017), Ophiobolin A kills human glioblastoma cells by inducing endoplasmic reticulum stress via disruption of thiol proteostatis; Oncotarget, 8 106740 5) Rodolfo et al. (2016), Ophiobolin A Induces Autophagy and Activates the Mitochondrial Pathway of Apoptosis in Human Melanoma Cells; PLoS One, 11 e0167672

InChI:InChI=1/C25H36O4/c1-15(2)10-18-11-16(3)25(29-18)9-8-23(4)12-19-22(20(27)13-24(19,5)28)17(14-26)6-7-21(23)25/h6,10,14,16,18-19,21-22,28H,7-9,11-13H2,1-5H3/b17-6-

Upstream product

• 1344673-75-1 2-[(2R,4S,5S,6R,7S)-2-tert-butyldiphenylsilyloxymethyl-7-formyl-4,7-dimethyl-1-oxaspiro[4.4]non-6-yl]ethyl pivalate 
• 1344673-84-2 2-[(2R,4S,5S,6R,7S)-2-tert-butyldiphenylsilyloxymethyl-7-hydroxymethyl-4,7-dimethyl-1-oxaspiro[4.4]non-6-yl]ethyl pivalate 
• 1344673-73-9 (1R,2S,3S,4S)-4-(benzyloxy)-2-{[(2R,4S,5S,6R,7R)-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-4,7-dimethyl-6-prop-2-en-1-yl-1-oxaspiro[4.4]non-7-yl]methyl}-3-[1-(hydroxymethyl)ethenyl]-1-methylcyclopentanol 

Relevant articles and documents

Enantioselective total synthesis of (+)-ophiobolin A

The enantioselective total synthesis of (+)-ophiobolin A is described. This total synthesis features the construction of the spiro CD ring of (+)-ophiobolin A through a stereoselective intramolecular Hosomi-Sakurai cyclization reaction, the joining of the