Vibralactone D
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| Category | Enzyme inhibitors |
| Catalog number | BBF-04387 |
| CAS | 1251748-32-9 |
| Molecular Weight | 210.27 |
| Molecular Formula | C12H18O3 |
| Purity | ≥98% |
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Description
Vibralactone D is isolated from Boreostereum vibrans and exhibits weak inhibitory effect against isozymes of 11beta-hydroxysteroid dehydrogenases (HSD).
Specification
| Synonyms | (1S,5R,6S)-6-hydroxy-5-(3-methylbut-2-enyl)-3-oxabicyclo[3.2.1]octan-4-one; 3-Oxabicyclo[3.2.1]octan-2-one, 7-hydroxy-1-(3-methyl-2-buten-1-yl)-, (1R,5S,7S)- |
| Storage | Store at 2-8°C |
| IUPAC Name | (1R,5S,7S)-7-hydroxy-1-(3-methylbut-2-enyl)-3-oxabicyclo[3.2.1]octan-2-one |
| Canonical SMILES | CC(=CCC12CC(CC1O)COC2=O)C |
| InChI | InChI=1S/C12H18O3/c1-8(2)3-4-12-6-9(5-10(12)13)7-15-11(12)14/h3,9-10,13H,4-7H2,1-2H3/t9-,10+,12-/m1/s1 |
| InChI Key | SUNCJWCQYMBYLA-JFGNBEQYSA-N |
Properties
| Appearance | Powder |
| Boiling Point | 362.5±25.0°C at 760 mmHg |
| Density | 1.2±0.1 g/cm3 |
| Solubility | Soluble in Methanol |
Reference Reading
1. Antifungal activities of secondary metabolites isolated from liquid fermentations of Stereum hirsutum (Sh134-11) against Botrytis cinerea (grey mould agent)
Pedro Aqueveque, Carlos L Céspedes, José Becerra, Mario Aranda, Olov Sterner Food Chem Toxicol. 2017 Nov;109(Pt 2):1048-1054. doi: 10.1016/j.fct.2017.05.036. Epub 2017 May 18.
Extracts obtained from liquid mycelial fermentations of the Chilean fungus Stereum hirsutum (Sh134-11) showed antifungal activity against Botrytis cinerea. Two types of extracts were obtained: EtOAc-extract (liquid phase) and MeOH-extract (mycelial phase). Plate diffusion assay showed that EtOAc-extracts were more active than MeOH-extracts. A large-scale fermentation of Sh134-11 and chromatographic methods allowed to isolated four compounds: MS-3, Vibralactone, Vibralactone B and Sterenin D. Only Sterenin D showed antifungal activity against B. cinerea in the tests performed. Effects on the mycelial growth of B. cinerea showed that Sterenin D showed inhibition at 1000-2000 μg/mL reaching 67% and 76% respectively. Sterenin D was more effective to control the sporogenesis, inhibiting in 96% the sporulation at 500 μg/mL. Assays showed that Sterenin D exhibited a minimal fungicidal concentration (MFC) of 50 μg/mL and minimal inhibitory concentration (MIC) at 20 μg/mL. Our study indicated that submerged fermentations of Chilean S. hirsutum (Sh134-11) produced extracts with antifungal activity and Sterenin D is responsible for this activity, which could be used as possible biofungicides alternative to synthetic fungicides.
2. Vibralactones D-F from cultures of the basidiomycete Boreostereum vibrans
Meng-Yuan Jiang, Ling Zhang, Ze-Jun Dong, Zhu-Liang Yang, Ying Leng, Ji-Kai Liu Chem Pharm Bull (Tokyo). 2010 Jan;58(1):113-6. doi: 10.1248/cpb.58.113.
Three new metabolites, vibralactones D-F (1-3) were isolated from cultures of the basidiomycete Boreostereum vibrans. The relative configuration of 1 was established on the basis of X-ray diffraction analysis, while the absolute configurations of 1-3 were assigned using a modified Mosher's method. Compound 1 showed weak inhibitory activities against isozymes of 11beta-hydroxysteroid dehydrogenases (HSD) with IC(50) values of 85.7 microM (human HSD1), 295.2 microM (mouse HSD1), and 87.1 microM (human HSD2).
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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 ╳
