Aurantiogliocladin
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| Category | Antibiotics |
| Catalog number | BBF-00607 |
| CAS | 483-54-5 |
| Molecular Weight | 196.20 |
| Molecular Formula | C10H12O4 |
| Purity | 95% |
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Description
It is produced by the strain of Gliocladium roseum. Aurantiogliocladin has weak activity of anti-gram positive bacteria, negative bacteria and fungal.
Specification
| Synonyms | 2,3-DIMETHOXY-5,6-DIMETHYL-2,5-CYCLOHEXADIENE-1,4-DIONE; 2,3-DIMETHOXY-5,6-DIMETHYL-P-BENZOQUINONE; AURANTIOGLIOCLADIN; 2,3-Dimethoxy-5,6-dimethyl-1,4-benzoquinone |
| IUPAC Name | 2,3-dimethoxy-5,6-dimethylcyclohexa-2,5-diene-1,4-dione |
| Canonical SMILES | CC1=C(C(=O)C(=C(C1=O)OC)OC)C |
| InChI | InChI=1S/C10H12O4/c1-5-6(2)8(12)10(14-4)9(13-3)7(5)11/h1-4H3 |
| InChI Key | NOYQJVWDVBANHI-UHFFFAOYSA-N |
Properties
| Appearance | Orange Flake Crystalline |
| Antibiotic Activity Spectrum | gram-positive bacterial; gram-negative bacteria; fungi |
| Boiling Point | 337.326°C at 760 mmHg |
| Melting Point | 62-63 °C |
| Density | 1.167 g/cm3 |
Reference Reading
1. Anthelmintic constituents of Clonostachys candelabrum
Sloan Ayers, Deborah L Zink, Kenneth Mohn, Joanne S Powell, Christine M Brown, Gerald Bills, Alan Grund, Donald Thompson, Sheo B Singh J Antibiot (Tokyo). 2010 Mar;63(3):119-22. doi: 10.1038/ja.2009.131. Epub 2010 Jan 15.
Five diastereomeric polyketide glycosides, roselipins 3A-3E (1-5), have been isolated from the acetone extract of Clonostachys candelabrum on the basis of their positive anthelmintic activity. The structures of these compounds were elucidated by comparison of their NMR and MS data to those of previously reported roselipins and related structures, and were confirmed by 2D-NMR spectral analysis. Known compounds linoleic acid (6) and aurantiogliocladin (7) were also isolated as active anthelmintic components, although much less potent than the roselipins.
2. Aurantiogliocladin inhibits biofilm formation at subtoxic concentrations
Kamila Tomoko Yuyama, Thaís Souto Paula da Costa Neves, Marina Torquato Memória, Iago Toledo Tartuci, Wolf-Rainer Abraham AIMS Microbiol. 2017 Jan 24;3(1):50-60. doi: 10.3934/microbiol.2017.1.50. eCollection 2017.
Infections where pathogens are organized in biofilms are difficult to treat due to increased antibiotic resistances in biofilms. To overcome this limitation new approaches are needed to control biofilms. One way is to screen natural products from organisms living in a wet environment. The rational is that these organisms are preferentially threatened by biofilm formation and may have developed strategies to control pathogens in these biofilms. In a screen of fungal isolates obtained from the Harz mountains in Germany several strains have been found producing compounds for the inhibition of biofilms. One of these strains has been identified as Clonostachys candelabrum producing aurantiogliocladin. Biological tests showed aurantiogliocladin as a weak antibiotic which was active against Staphylococcus epidermidis but not S. aureus. Aurantiogliocladin could also inhibit biofilm formation of several of the tested bacterial strains. This inhibition, however, was never complete but biofilm inhibition activity was also found at concentrations below the minimal inhibitory concentrations, e. g. Bacillus cereus with a MIC of 128 µg mL-1 showed at 32 µg mL-1 still 37% biofilm inhibition. In agreement with this finding was the observation that aurantiogliocladin was bacteriostatic for the tested bacteria but not bactericidal. Because several closely related toluquinones with different antibiotic activities have been reported from various fungi screening of a chemical library of toluquinones is suggested for the improvement of biofilm inhibition activities.
3. Studies on the Host-finding Mechanisms of Neotylenchus linfordi
J W Klink, V H Dropkin, J E Mitchell J Nematol. 1970 Apr;2(2):106-17.
The plant-parasitic nematode, Neotylenchus linlordi, congregated around colonies or filtrates from mycelia of Gliocladium roseum, Rhizoctonia solani, Pyrenochaeta terrestris and Chaetomium indicum. The average time required for the nematodes to reach the fungal colonies ranged from less than 4 hr for G. roseum to 20 hr for R. solani. Nematodes first circled near the point of introduction, then moved toward the fungus or filtrate. Several methods of measuring the response of N. linfordi to G. roseum culture filtrate were evaluated. The response was strongest when the test materials were assayed on an agar disk submerged in water agar and the introduced nematodes suspended in agar in a center well midway between the test materials. Filtrates obtained from cultures of G. roseum incubated between 12 and 21 days in potato dextrose broth, were most active. The attractants were small thermostable molecules, soluble in methyl alcohol and unaffected by pH. A yellow pigment with properties similar to a mixture of aurantiogliocladin, rubrogliocladin, and gliorosein was shown to be one of the active materials. The response of N. linfordi to the G. roseum filtrate was not associated with any nutritive factors which would result in reproduction.
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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 ╳
