Pyrenophorin
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| Category | Antibiotics |
| Catalog number | BBF-02094 |
| CAS | 5739-85-5 |
| Molecular Weight | 308.33 |
| Molecular Formula | C16H20O6 |
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Description
Pyrenophorin is a macrocyclic polylactone antibiotic produced by Pyrenophora averae NH7. It has activity against Gram-positive bacteria, mycobacteria, filamentous fungi, yeast-like fungi and Trichomonas.
Specification
| Synonyms | 1,9-Dioxacyclohexadeca-3,11-diene-2,5,10,13-tetrone, 8,16-dimethyl-, (8R-(3E,8R*,11E,16R*))- |
| IUPAC Name | (3Z,8R,11Z,16R)-8,16-dimethyl-1,9-dioxacyclohexadeca-3,11-diene-2,5,10,13-tetrone |
| Canonical SMILES | CC1CCC(=O)C=CC(=O)OC(CCC(=O)C=CC(=O)O1)C |
| InChI | InChI=1S/C16H20O6/c1-11-3-5-13(17)8-10-16(20)22-12(2)4-6-14(18)7-9-15(19)21-11/h7-12H,3-6H2,1-2H3/b9-7-,10-8-/t11-,12-/m1/s1 |
| InChI Key | PJHRIHGUXQTQLU-WICDBLAJSA-N |
Properties
| Appearance | Colorless Needle Crystal |
| Antibiotic Activity Spectrum | Gram-positive bacteria; mycobacteria; fungi; yeast |
| Boiling Point | 545.5±50.0°C at 760 mmHg |
| Melting Point | 174-175°C |
| Density | 1.1±0.1 g/cm3 |
Reference Reading
1. Physiological and ultrastructural changes in "green islands" on Avena sterilis leaves caused by (8R,16R)-(-)-pyrenophorin
C Fasseas, K A Aliferis, M Chrysayi-Tokousbalides Plant Physiol Biochem . 2006 Nov-Dec;44(11-12):851-6. doi: 10.1016/j.plaphy.2006.10.006.
The biochemical and ultrastructural changes in "green islands" (GIs) on detached Avena sterilis leaves caused by the macrodiolide (8R,16R)-(-)-pyrenophorin in the dark were examined. In the absence of light, leaf segments retained their photosynthetic pigments for 96 h after treatment with (8R,16R)-(-)-pyrenophorin (70 muM), whereas in the untreated leaves complete senescence, loss of photosynthetic pigments and cell disorganization were observed 72 h after detachment. Proteolytic enzyme activity in treated tissues with pyrenophorin remained at low levels for 96 h after treatment and protein dissipation was lower in the treated than in the untreated. Although tissues in "GIs" seem macroscopically healthy, electron microscopy observations revealed structurally disorganized cells filled with granular, electron-dense material. Chloroplasts were severely damaged and contained a large number of plastoglobuli. Similar ultrastructural changes were also observed in A. sterilis tissues treated with the phytotoxin under illumination, indicating a mechanism operating both under illumination and in the dark.
2. Exploiting the reversibility of olefin metathesis. Syntheses of macrocyclic trisubstituted alkenes and (R,R)-(-)-pyrenophorin
O R Thiel, A Fürstner, L Ackermann Org Lett . 2001 Feb 8;3(3):449-51. doi: 10.1021/ol0069554.
[figure: see text] The formation of the trisubstituted cycloalkene 7 by RCM of diene 5 proceeds via the acyclic dimer 6, thus demonstrating the ready reversibility of olefin metathesis if catalyzed by "second generation" ruthenium carbene complexes such as 2-4. When applied to acrylate 11, these catalysts trigger a cyclooligomerization process that evolves with time and serves as key step en route to the lactide antibiotic (-)-pyrenophorin 8.
3. Antifungal metabolites from fungal endophytes of Pinus strobus
Mark W Sumarah, Julie R Kesting, J David Miller, Dan Sørensen Phytochemistry . 2011 Oct;72(14-15):1833-7. doi: 10.1016/j.phytochem.2011.05.003.
The extracts of five foliar fungal endophytes isolated from Pinus strobus (eastern white pine) that showed antifungal activity in disc diffusion assays were selected for further study. From these strains, the aliphatic polyketide compound 1 and three related sesquiterpenes 2-4 were isolated and characterized. Compound 2 is reported for the first time as a natural product and the E/Z conformational isomers 3 and 4 were hitherto unknown. Additionally, the three known macrolides; pyrenophorol (5), dihydropyrenophorin (6), and pyrenophorin (7) were isolated and identified. Their structures were elucidated by spectroscopic analyses including 2D NMR, HRMS and by comparison to literature data where available. The isolated compounds 1, 2, and 5 were antifungal against both the rust Microbotryum violaceum and Saccharomyces cerevisae.
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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 ╳
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