Strobilurin F
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| Category | Antibiotics |
| Catalog number | BBF-03081 |
| CAS | 129145-63-7 |
| Molecular Weight | 358.43 |
| Molecular Formula | C21H26O5 |
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Description
Strobilurin F is an antibiotic produced by Bolina lutea Sacc. It has strong anti-fungal activity, and its in vitro anti-tumor proliferation IC50 is 2.2 µmol/L.
Specification
| IUPAC Name | methyl (2E,3Z,5E)-6-[3-hydroxy-4-(3-methylbut-2-enoxy)phenyl]-2-(methoxymethylidene)-3-methylhexa-3,5-dienoate |
| Canonical SMILES | CC(=CCOC1=C(C=C(C=C1)C=CC=C(C)C(=COC)C(=O)OC)O)C |
| InChI | InChI=1S/C21H26O5/c1-15(2)11-12-26-20-10-9-17(13-19(20)22)8-6-7-16(3)18(14-24-4)21(23)25-5/h6-11,13-14,22H,12H2,1-5H3/b8-6+,16-7-,18-14+ |
| InChI Key | WMDIAAUGKNWXHK-GEVYMXDOSA-N |
Properties
| Appearance | Colorless Crystal |
| Antibiotic Activity Spectrum | fungi; neoplastics (Tumor) |
| Boiling Point | 536.7°C at 760 mmHg |
| Melting Point | 77.5-78°C |
| Density | 1.104 g/cm3 |
Reference Reading
1. Strobilurin D and strobilurin F: two new cytostatic and antifungal (E)-beta-methoxyacrylate antibiotics from Cyphellopsis anomala (1)
W Weber, T Anke, M Bross, W Steglich Planta Med. 1990 Oct;56(5):446-50. doi: 10.1055/s-2006-961008.
Strobilurin D and strobilurin F, two new cytostatic and antifungal antibiotics of the (E)-beta-methoxyacrylate class, have been isolated from mycelial cultures of the basidiomycete Cyphellopsis anomala (Pers. ex Fr.) Sing. The structures were elucidated by spectroscopic methods. The antibiotics inhibit the growth of human and animal cells and a wide variety of fungi. Like strobilurins A and B, the new metabolites are potent inhibitors of respiration.
2. Strobilurins F, G and H, three new antifungal metabolites from Bolinea lutea. I. Fermentation, isolation and biological activity
A Fredenhagen, A Kuhn, H H Peter, V Cuomo, U Giuliano J Antibiot (Tokyo). 1990 Jun;43(6):655-60. doi: 10.7164/antibiotics.43.655.
Three new strobilurins F, G and H, antibiotics with antifungal activity, were isolated from cultures of Bolinea lutea Sacc. These new compounds differ from previously described analogs in their aromatic substitution. An HPLC method allows complete separation of all the components.
3. Bolineol, a novel co-metabolite of strobilurins A, F and G from Bolinea lutea
Colin T Bedford, David Perry, Rajnesh K Sharma Nat Prod Res. 2008;22(17):1535-9. doi: 10.1080/14786410802176737.
A mycelial co-metabolite of strobilurin A, F and G from Bolinea lutea, which we have named bolineol, has been characterised for the first time. Bolineol (methyl 2-hydroxymethyl-3-methyl-6-phenyl-3Z,5E-hexadienoate) has a similar carbon skeleton to strobilurin A but differs in oxidation level. Its structure has been deduced from its spectral characteristics and those of its acetate. The known compound strobilurin F-1 (methyl 2-methoxymethylene-3-methyl-6-(3'-hydroxyphenyl)-3Z,5E-hexadienoate) has been detected in this organism for the first time and converted into its acetate, a new compound, the structure of which was assigned from its spectral data.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
