Antimycin A4
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| Category | Bioactive by-products |
| Catalog number | BBF-00555 |
| CAS | 27220-59-3 |
| Molecular Weight | 506.54 |
| Molecular Formula | C25H34N2O9 |
| Purity | >98% by HPLC |
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Description
Antimycin A is a macrolide antibiotic produced by Streptomyces kitasawaensis, Str. griseus and Str. antibioticus. Antimycin A4 can inhibit atp-citrate lyase activity.
Specification
| Synonyms | 8-Butyl-3-(3-formamido-2-hydroxybenzamido)-2,6-dimethyl-4,9-dioxo-1,5-dioxonan-7-yl butyrate |
| Storage | -20°C |
| IUPAC Name | [8-butyl-3-[(3-formamido-2-hydroxybenzoyl)amino]-2,6-dimethyl-4,9-dioxo-1,5-dioxonan-7-yl] butanoate |
| Canonical SMILES | CCCCC1C(C(OC(=O)C(C(OC1=O)C)NC(=O)C2=C(C(=CC=C2)NC=O)O)C)OC(=O)CCC |
| InChI | InChI=1S/C25H34N2O9/c1-5-7-10-17-22(36-19(29)9-6-2)15(4)35-25(33)20(14(3)34-24(17)32)27-23(31)16-11-8-12-18(21(16)30)26-13-28/h8,11-15,17,20,22,30H,5-7,9-10H2,1-4H3,(H,26,28)(H,27,31) |
| InChI Key | GYANSQKXOLFAFP-UHFFFAOYSA-N |
| Source | Streptomyces sp. |
Properties
| Appearance | White solid |
| Boiling Point | 744.9°C at 760 mmHg |
| Melting Point | 164-165°C |
| Density | 1.27 g/cm3 |
| Solubility | Soluble in ethanol, methanol, DMF or DMSO. Poor water solubility. |
Reference Reading
1. Antimycins, inhibitors of ATP-citrate lyase, from a Streptomyces sp
R Cooper, A M Gillum, H H Sun, V Marinelli, C C Chadwick, J J Oleynek, C J Barrow, D M Sedlock, P Kaplita J Antibiot (Tokyo) . 1997 Sep;50(9):729-33. doi: 10.7164/antibiotics.50.729.
A related group of compounds belonging to the antimycin class of antibiotics was found in culture broth produced by a Streptomyces species. The group includes known antimycins A1, A2, A3 and A4, and new antimycins A7 and A8. These compounds inhibit ATP-citrate lyase with Ki values of 4 to 60 microM against the substrate magnesium citrate. The structures of the new antimycins were determined by spectroscopic analyses.
2. Preparative separation of six antimycin A components from antimycin fermentation broth by high-speed counter-current chromatography
Hong Jiang, Yaoming Wen, Wei Zheng, Jiaoyan Wang, Ying Xie, Huaiwang Wang, Xiuming Chen, Jingming Zhou, Yuhan Lin J Chromatogr A . 2010 Sep 3;1217(36):5687-92. doi: 10.1016/j.chroma.2010.07.003.
A method of using high-speed counter-current chromatography (HSCCC) was established for preparative isolation and purification of antimycin A components from antimycin fermentation broth. Six antimycin A components were successfully purified for the first time by HSCCC with a two-phase solvent system composed of n-hexane-ethyl acetate-methanol-water (5:2:4:1, by volume). Total of 20mg antimycin A(4)(a or b), 25mg antimycin A(3)(a or b), 21mg antimycin A(8)(a or b), 34mg antimycin A(2)(a or b), 26mg antimycin A(1)(a or b) and 34mg antimycin A(1)(a or b) with the purities of 93.2, 98.6, 96.2, 94.1, 94.9 and 96.7%, respectively, determined by high-performance liquid chromatography (HPLC), were yielded from 200mg crude sample only in one HSCCC run.
3. Chemical basis of the synergism and antagonism in microbial communities in the nests of leaf-cutting ants
Ilka Schoenian, Hubert Herz, Manoj Ghaste, Dieter Spiteller, Rainer Wirth, Michael Spiteller Proc Natl Acad Sci U S A . 2011 Feb 1;108(5):1955-60. doi: 10.1073/pnas.1008441108.
Leaf-cutting ants cultivate the fungus Leucoagaricus gongylophorus, which serves as a major food source. This symbiosis is threatened by microbial pathogens that can severely infect L. gongylophorus. Microbial symbionts of leaf-cutting ants, mainly Pseudonocardia and Streptomyces, support the ants in defending their fungus gardens against infections by supplying antimicrobial and antifungal compounds. The ecological role of microorganisms in the nests of leaf-cutting ants can only be addressed in detail if their secondary metabolites are known. Here, we use an approach for the rapid identification of established bioactive compounds from microorganisms in ecological contexts by combining phylogenetic data, database searches, and liquid chromatography electrospray ionisation high resolution mass spectrometry (LC-ESI-HR-MS) screening. Antimycins A(1)-A(4), valinomycins, and actinomycins were identified in this manner from Streptomyces symbionts of leaf-cutting ants. Matrix-assisted laser desorption ionization (MALDI) imaging revealed the distribution of valinomycin directly on the integument of Acromyrmex echinatior workers. Valinomycins and actinomycins were also directly identified in samples from the waste of A. echinatior and A. niger leaf-cutting ants, suggesting that the compounds exert their antimicrobial and antifungal potential in the nests of leaf-cutting ants. Strong synergistic effects of the secondary meta-bolites produced by ant-associated Streptomyces were observed in the agar diffusion assay against Escovopsis weberi. Actinomycins strongly inhibit soil bacteria as well as other Streptomyces and Pseudonocardia symbionts. The antifungal antimycins are not only active against pathogenic fungi but also the garden fungus L. gongylophorus itself. In conclusion, secondary metabolites of microbial symbionts of leaf-cutting ants contribute to shaping the microbial communities within the nests of leaf-cutting ants.
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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 ╳
