WS-5995 B
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| Category | Antibiotics |
| Catalog number | BBF-01644 |
| CAS | |
| Molecular Weight | 338.3 |
| Molecular Formula | C19H14O6 |
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Description
WS-5995 B is an antibiotic produced by Streptomyces auranticolor. It exhibits weak ctivity against Proteus and trichomonas vaginalis.
Specification
| Synonyms | Antibiotic WS5995B |
| IUPAC Name | 2-(5-hydroxy-1,4-dioxonaphthalen-2-yl)-3-methoxy-5-methylbenzoic acid |
| Canonical SMILES | CC1=CC(=C(C(=C1)OC)C2=CC(=O)C3=C(C2=O)C=CC=C3O)C(=O)O |
| InChI | InChI=1S/C19H14O6/c1-9-6-12(19(23)24)16(15(7-9)25-2)11-8-14(21)17-10(18(11)22)4-3-5-13(17)20/h3-8,20H,1-2H3,(H,23,24) |
| InChI Key | SFCJKMQKLHNLCX-UHFFFAOYSA-N |
Properties
| Appearance | Yellow Needle Crystal |
| Antibiotic Activity Spectrum | parasites |
Reference Reading
1. New anticoccidial antibiotics, WS-5995 A and B. I. Isolation and characterization
H Ikushima, M Okamoto, H Tanaka, O Ohe, M Kohsaka, H Aoki, H Imanaka J Antibiot (Tokyo). 1980 Oct;33(10):1107-13. doi: 10.7164/antibiotics.33.1107.
WS-5995 A, B and C are produced by a new strain of Streptomyces designated Streptomyces auranticolor. These antibiotics were purified by solvent extraction followed by chromatography on silica gel and then crystallized. WS-5995 A (C19H12O6, m.p., 289 approximately 291 degrees C) and WS-5995 B (C19H14O6, sublimation at 300 degrees C) protect chickens from infection with Eimeria tenella, a species of coccidia, which produces morbidity or mortality in chickens. WS-5995 C (C19H14O 7, m.p. 288 approximately 290 degrees C), a biologically inactive component, was found to be converted to WS-5995 A on treatment with trifluoroacetic anhydride.
2. WS-5995 B, an antifungal agent inducing differential gene expression in the conifer pathogen Heterobasidion annosum but not in Heterobasidion abietinum
Nina A Lehr, Aleksandra Adomas, Frederick O Asiegbu, Rüdiger Hampp, Mika T Tarkka Appl Microbiol Biotechnol. 2009 Nov;85(2):347-58. doi: 10.1007/s00253-009-2254-7. Epub 2009 Oct 2.
The mycorrhization helper bacterium Streptomyces sp. AcH 505 inhibits Norway spruce root infection and colonisation by the root and butt rot fungus Heterobasidion annosum 005 but not by the congeneric strain Heterobasidion abietinum 331 because of higher sensitivity of H. annosum 005 towards the AcH 505-derived naphthoquinone antibiotic WS-5995 B. Differences in antibiotic sensitivity between two isolates belonging to two species, H. annosum 005 and H. abietinum 331, were investigated by comparative gene expression analysis using macroarrays and quantitative RT-PCR after WS-5995 B, structurally related mollisin and unrelated cycloheximide application. Treatment with 25 microM WS-5995 B for 2 h resulted in a significant up-regulation of expression of inosine-5'-monophosphate dehydrogenase, phosphoglucomutase and GTPase genes, while the expression of genes encoding for thioredoxin and glutathione dependent formaldehyde dehydrogenase was down-regulated in the sensitive fungal strain. No differential expression in the tolerant strain was detected. Application of WS-5995 B at higher concentrations over a time course experiment revealed that H. annosum 005 and H. abietinum 331 responded differently to WS-5995 B. The fungal gene expression levels depended on both the concentration of WS-5995 B and the duration of its application. The WS-5995 B-unrelated cycloheximide caused highly specific changes in patterns of gene expression. Our findings indicate considerable variations in response to bacterial metabolites by the isolates of the conifer pathogen.
3. Auxofuran, a novel metabolite that stimulates the growth of fly agaric, is produced by the mycorrhiza helper bacterium Streptomyces strain AcH 505
Julia Riedlinger, Silvia D Schrey, Mika T Tarkka, Rüdiger Hampp, Manmohan Kapur, Hans-Peter Fiedler Appl Environ Microbiol. 2006 May;72(5):3550-7. doi: 10.1128/AEM.72.5.3550-3557.2006.
The mycorrhiza helper bacterium Streptomyces strain AcH 505 improves mycelial growth of ectomycorrhizal fungi and formation of ectomycorrhizas between Amanita muscaria and spruce but suppresses the growth of plant-pathogenic fungi, suggesting that it produces both fungal growth-stimulating and -suppressing compounds. The dominant fungal-growth-promoting substance produced by strain AcH 505, auxofuran, was isolated, and its effect on the levels of gene expression of A. muscaria was investigated. Auxofuran and its synthetic analogue 7-dehydroxy-auxofuran were most effective at a concentration of 15 microM, and application of these compounds led to increased lipid metabolism-related gene expression. Cocultivation of strain AcH 505 and A. muscaria stimulated auxofuran production by the streptomycete. The antifungal substances produced by strain AcH 505 were identified as the antibiotics WS-5995 B and C. WS-5995 B completely blocked mycelial growth at a concentration of 60 microM and caused a cell stress-related gene expression response in A. muscaria. Characterization of these compounds provides the foundation for molecular analysis of the fungus-bacterium interaction in the ectomycorrhizal symbiosis between fly agaric and spruce.
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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 ╳
