Vibralactone B
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| Category | Bioactive by-products |
| Catalog number | BBF-04385 |
| CAS | 1093230-95-5 |
| Molecular Weight | 224.25 |
| Molecular Formula | C12H16O4 |
| Purity | ≥98% |
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Description
Vibralactone B is an antibacterial compound produced from liquid fermentations of Stereum hirsutum that inhibits the growth of E. coli and Pseudomonas aeruginosa.
Specification
| Synonyms | (1beta)-2alpha-Prenyl-3beta-hydroxy-5beta-(hydroxymethyl)-6-oxabicyclo[3.1.0]hexane-2-carboxylic acid 2,3-lactone; 3,7-Dioxatricyclo[4.2.0.02,4]octan-8-one, 4-(hydroxymethyl)-1-(3-methyl-2-buten-1-yl)-, (1S,2R,4R,6S)-; (1S,2R*,3R*,5S)-2,3-epoxyvibralactone |
| Storage | Store at 2-8°C |
| IUPAC Name | (1S,2R,4R,6S)-4-(hydroxymethyl)-1-(3-methylbut-2-enyl)-3,7-dioxatricyclo[4.2.0.02,4]octan-8-one |
| Canonical SMILES | CC(=CCC12C(CC3(C1O3)CO)OC2=O)C |
| InChI | InChI=1S/C12H16O4/c1-7(2)3-4-12-8(15-10(12)14)5-11(6-13)9(12)16-11/h3,8-9,13H,4-6H2,1-2H3/t8-,9-,11+,12-/m0/s1 |
| InChI Key | NOIVROLINHAPPT-XPXLGCRWSA-N |
Properties
| Appearance | Powder |
| Antibiotic Activity Spectrum | Gram-negative bacteria |
| Boiling Point | 361.0±37.0°C at 760 mmHg |
| Melting Point | 115-116°C (ethyl acetate) |
| Density | 1.3±0.1 g/cm3 |
| Solubility | Soluble in Methanol |
Reference Reading
1. Vibralactone Biogenesis-Associated Analogues from Submerged Cultures of the Fungus Boreostereum vibrans
He-Ping Chen, Meng-Yuan Jiang, Zhen-Zhu Zhao, Tao Feng, Zheng-Hui Li, Ji-Kai Liu Nat Prod Bioprospect. 2018 Feb;8(1):37-45. doi: 10.1007/s13659-017-0147-5. Epub 2017 Dec 5.
A scale-up fermentation of the fungus Boreostereum vibrans facilitated the isolation of six new vibralactone biogenesis-associated analogues, namely vibralactamide A (1), vibralactone T (2), 13-O-lactyl vibralactone (3), 10-O-acetyl vibralactone G (4), (11R,12R)- and (11S,12R)-vibradiol (5, 6). Their structures were established via extensive spectroscopic analyses, specific optical rotation comparison, and Snatzke's method. The biosynthetic pathway for vibralactamide A was postulated. The absolute configuration of vibralactone B was revised by single crystal X-ray diffraction analysis. This work puts the divergent vibralactone biosynthesis pathway one step further and expands the structural diversity of vibralactone-associated compounds.
2. 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.
3. Novel Natural Oximes and Oxime Esters with a Vibralactone Backbone from the Basidiomycete Boreostereum vibrans
He-Ping Chen, Zhen-Zhu Zhao, Zheng-Hui Li, Ze-Jun Dong, Kun Wei, Xue Bai, Ling Zhang, Chun-Nan Wen, Tao Feng, Ji-Kai Liu ChemistryOpen. 2016 Jan 13;5(2):142-9. doi: 10.1002/open.201500198. eCollection 2016 Apr.
A variety of novel natural products with significant bioactivities are produced by the basidiomycete Boreostereum vibrans. In the present study, we describe 16 novel natural oximes and oxime esters with a vibralactone backbone, vibralactoximes, which were isolated from the scale-up fermentation broth of B. vibrans. Their structures were determined through extensive spectroscopic analyses. These compounds represent the first oxime esters from nature. The hypothetical biosynthetic pathway of these compounds was also proposed. Seven compounds exhibited significant pancreatic lipase inhibitory activity, while ten compounds exhibited cytotoxicities against five human cancer cell lines (HL-60, SMMC-7721, A-549, MCF-7, and SW480), with IC50 values comparable with those of cisplatin.
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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 ╳
