| Identification | Back Directory | [Name]
OPHIOBOLIN A | [CAS]
4611-05-6 | [Synonyms]
ophiobolin
cochliobolin
OPHIOBOLIN A
COCHLIOBOLIN A
Ophiobolin A >=95% (HPLC)
Ophiobolin, Helminthosporium sp.
ophiobolin A from helminthosporium sp.
Cochliobolin A, Ophiobolin, Ophiobalin
18-epoxy-3-hydroxy-5-oxo-19-dien-25-a(18r)-ophiobola-14
(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
Spiro[dicyclopenta[a,d]cyclooctene-3(2H),2'(3'H)-furan]-6-carboxaldehyde, 1,3a,4,4',5',6a,7,8,9,9a,10,10a-dodecahydro-9-hydroxy-3',9,10a-trimethyl-5'-(2-methyl-1-propen-1-yl)-7-oxo-, (2'S,3'S,3aR,5'R,6aS,9R,9aS,10aR)- | [Molecular Formula]
C25H36O4 | [MDL Number]
MFCD00058400 | [MOL File]
4611-05-6.mol | [Molecular Weight]
400.55 |
| Chemical Properties | Back Directory | [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 Data | Back Directory | [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. |
| Hazard Information | Back Directory | [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. | [Biological Activity]
Cell permeable antagonist of calmodulin. Inhibits Ca2+/calmodulin-dependent phosphodiesterase. Inhibits P-glycoprotein-mediated transport. Exhibits antibacterial, antitumor and nematocidal activities. Phytotoxic. | [storage]
Store at -20°C,protect from light | [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 |
|
| Company Name: |
Lynnchem
|
| Telephone: |
86-(0)29-85992781 17792393971 |
| Website: |
http://www.lynnchem.com/ |
| Company Name: |
Energy Chemical
|
| Telephone: |
021-58432009 400-005-6266 |
| Website: |
http://www.energy-chemical.com |
|