Griseolutein A
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| Category | Bioactive by-products |
| Catalog number | BBF-01288 |
| CAS | 573-84-2 |
| Molecular Weight | 342.30 |
| Molecular Formula | C17H14N2O6 |
| Purity | >98% |
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Description
It is produced by the strain of Streptomyces griseoluteus. Griseolutein A and Griseolutein B have similar activitiy against gram-positive and negative bacteria.
Specification
| Synonyms | 6-(((Hydroxyacetyl)oxy)methyl)-9-methoxy-1-phenazinecarboxylic acid; 1-Phenazinecarboxylic acid, 6-(hydroxymethyl)-9-methoxy-, glycolate (ester) |
| IUPAC Name | 6-[(2-hydroxyacetyl)oxymethyl]-9-methoxyphenazine-1-carboxylic acid |
| Canonical SMILES | COC1=CC=C(C2=NC3=CC=CC(=C3N=C12)C(=O)O)COC(=O)CO |
| InChI | InChI=1S/C17H14N2O6/c1-24-12-6-5-9(8-25-13(21)7-20)14-16(12)19-15-10(17(22)23)3-2-4-11(15)18-14/h2-6,20H,7-8H2,1H3,(H,22,23) |
| InChI Key | LRNVPBRAXOLPTF-UHFFFAOYSA-N |
Properties
| Appearance | Orange-Yellow Crystal |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria |
| Boiling Point | 635.6±45.0 °C (Predicted) |
| Melting Point | 194-197 °C |
| Density | 1.482±0.06 g/cm3 (Predicted) |
| Solubility | Soluble in Ethyl Acetate, Alcohol; Insoluble in Ether, Benzene, Water |
Reference Reading
1. Inhibition of DNA synthesis by griseolutein in Escherichia coli through a possible interaction at the cell surface
M Hori, S Nozaki, K Nagami, H Asakura, H Umezawa Biochim Biophys Acta. 1978 Nov 21;521(1):101-10. doi: 10.1016/0005-2787(78)90252-6.
Griseolutein acts as a bactericidal agent, its toxicity decreasing with increase in cell density. There is no evidence that griseolutein acts at a specific stage of cell cycle. Inhibition of incorporation of radioactive thymidine into acid-insoluble fraction of cells is marked and rapid, while inhibition of incorporation of uridine also takes place. Incorporation of 32Pi into the acid-insoluble fraction of cells is inhibited while the incorporation into the nucleotide pool is not. Concentration of any of the four deoxyribonucleoside triphosphates in griseolutein-treated cells are similar to or higher than those in untreated cells. No extensive degradation of cellualr DNA is caused by griseolutein. DNA synthesis in plasmolyzed cells in not inhibited by griseolutein.
2. Modified phenazines from an Indonesian Streptomyces sp
Serge Fotso, Dwi Andreas Santosa, Rasti Saraswati, Jongtae Yang, Taifo Mahmud, T Mark Zabriskie, Philip J Proteau J Nat Prod. 2010 Mar 26;73(3):472-5. doi: 10.1021/np9005647.
Fractionation of the extract from the Indonesian Streptomyces sp. ICBB8198 as directed by the antibacterial activity delivered the known phenazine antibiotics griseoluteic acid (1a) and griseolutein A (1b), as well as two new phenazine derivatives (2 and 3). In addition, the known compounds spirodionic acid, dihydrosarkomycins, and 6-ethyl-4-hydroxy-3,5-dimethyl-2H-pyran-2-one (4a), along with the new pyrone 3,6-diethyl-4-hydroxy-5-methyl-2H-pyran-2-one (4b), were isolated. We report here the isolation, structure elucidation, and antibiotic activity of the new metabolites as well as a hypothetical pathway for the formation of the new phenazine derivatives.
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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 ╳
