Pterulone
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| Category | Enzyme inhibitors |
| Catalog number | BBF-03523 |
| CAS | 190143-31-8 |
| Molecular Weight | 234.68 |
| Molecular Formula | C13H11ClO2 |
| Purity | 95% |
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Description
Pterulone is a Coenzyme I: Coenzyme Q oxidoreductase inhibitor produced by Pterula sp. 82168. It has anti-yeast and filamentous fungus effect.
Specification
| Synonyms | (E)-Pterulone; Pterulone A |
| IUPAC Name | 1-[(3E)-3-(chloromethylidene)-1-benzoxepin-7-yl]ethanone |
| Canonical SMILES | CC(=O)C1=CC2=C(C=C1)OCC(=CCl)C=C2 |
| InChI | InChI=1S/C13H11ClO2/c1-9(15)11-4-5-13-12(6-11)3-2-10(7-14)8-16-13/h2-7H,8H2,1H3/b10-7+ |
| InChI Key | QEWSARCWWQPUSM-JXMROGBWSA-N |
Properties
| Appearance | Yellow Crystal |
| Antibiotic Activity Spectrum | fungi; yeast |
| Boiling Point | 408.4±45.0°C at 760 mmHg |
| Melting Point | 122-124°C |
| Density | 1.289±0.06 g/cm3 |
Reference Reading
1. Production of antibiotics by Collybia nivalis, Omphalotus olearis, a Favolaschia and a Pterula species on natural substrates
M Engler, T Anke, O Sterner Z Naturforsch C J Biosci. 1998 May-Jun;53(5-6):318-24. doi: 10.1515/znc-1998-5-604.
Collybia nivalis, Favolaschia sp. 87129, Pterula sp. 82168 and Omphalotus olearius were cultivated on natural substrates. The antibiotic metabolites oudemansin A. strobilurins A, D, illudin S and pterulone were isolated and identified. A new antifungal metabolite, pterulone B, was described from cultures of Pterula sp. 82168 on wood. Collybia nivalis was found to be the first species of this genus to produce strobilurins and oudemansin A. As compared to rich media the cultivation on natural substrates resulted in the production of fewer metabolites. The concentrations of the antibiotics, however, were sufficient to inhibit other saprophytic fungi.
2. Efficient syntheses of pterulone, pterulone B and related analogues
Philippe Lemaire, Geneviève Balme, Philippe Desbordes, Jean-Pierre Vors Org Biomol Chem. 2003 Dec 7;1(23):4209-19. doi: 10.1039/b306356a. Epub 2003 Oct 23.
An efficient synthesis of the three halogenated naturally occurring products, pterulone (2), pterulone B (3) and alcohol 5, and of a wide range of related unnatural analogues has been achieved starting from the two readily available 1-benzoxepine sulfonyl-containing intermediates 6a and 6b. The biological activities of pterulone and some of the synthesized analogues were tested against a wide spectrum of phytopathogenic fungi.
3. Pterulinic acid and pterulone, two novel inhibitors of NADH:ubiquinone oxidoreductase (complex I) produced by a Pterula species. II. Physico-chemical properties and structure elucidation
M Engler, T Anke, O Sterner J Antibiot (Tokyo). 1997 Apr;50(4):330-3. doi: 10.7164/antibiotics.50.330.
The structures of two novel fungal antibiotics, isolated from a Pterula species, that interfere with the NADH:ubiquinone oxidoreductase and inhibit the respiration of eucaryotes, were determined by spectroscopic techniques. Both compounds, pterulinic acid (1a) and pterulone (2), contain a 1-benzoxepin ring system and are chlorinated. Pterulinic acid (1a), which was obtained as a 1:5 inseparable mixture of the two isomers (Z)-1a and (E)-1a, in addition contains a furan. Their structures were determined by mass spectrometry and NMR spectroscopy, and 2D heteronuclear correlation experiments permitted the assignment of all NMR signals.
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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 ╳
