Tetrodecamycin
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| Category | Antibiotics |
| Catalog number | BBF-01145 |
| CAS | 156980-57-3 |
| Molecular Weight | 334.36 |
| Molecular Formula | C18H22O6 |
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Description
It is produced by the strain of Streptomyces nashvillensis MJ885-mF8. It has anti-gram-positive bacteria (MIC is 6.25-12.5 μg/mL) and PasteureRci pisciccida (MIC is 1.56-3.12 μg/mL) activity.
Specification
| Synonyms | (-)-tetrodecamycin; 5,11-Methanofuro(3,4-d)(3)benzoxonin-1,12(3H,5H)-dione,6,6a,7,8,9,10,10a,11-octahydro-6,6a-dihydroxy-11,13-dimethyl-3-methylene-, (5R-(5R*,6S*,6aR*,10aR*,11S*,13R*))- |
| IUPAC Name | (5S,6R,6aS,10aS,11R,13S)-6,6a-dihydroxy-11,13-dimethyl-3-methylene-6,6a,7,8,9,10,10a,11-octahydro-5,11-methanobenzo[f]furo[3,4-b]oxonine-1,12(3H,5H)-dione |
| Canonical SMILES | CC1C2C(C3(CCCCC3C1(C(=O)C4=C(O2)C(=C)OC4=O)C)O)O |
| InChI | InChI=1S/C18H22O6/c1-8-12-15(20)18(22)7-5-4-6-10(18)17(8,3)14(19)11-13(24-12)9(2)23-16(11)21/h8,10,12,15,20,22H,2,4-7H2,1,3H3 |
| InChI Key | VSUPSZGXABDKGD-UHFFFAOYSA-N |
Properties
| Appearance | Colorless Flaky Crystal |
| Antibiotic Activity Spectrum | gram-posotive becteria |
| Boiling Point | 502.1 °C at 760 mmHg |
| Melting Point | 87-94 °C |
| Density | 1.38 g/cm3 |
| Solubility | Soluble in Methanol |
Reference Reading
1. Biosynthetic Genes for the Tetrodecamycin Antibiotics
Tomas Gverzdys, Justin R Nodwell J Bacteriol. 2016 Jun 27;198(14):1965-1973. doi: 10.1128/JB.00140-16. Print 2016 Jul 15.
We recently described 13-deoxytetrodecamycin, a new member of the tetrodecamycin family of antibiotics. A defining feature of these molecules is the presence of a five-membered lactone called a tetronate ring. By sequencing the genome of a producer strain, Streptomyces sp. strain WAC04657, and searching for a gene previously implicated in tetronate ring formation, we identified the biosynthetic genes responsible for producing 13-deoxytetrodecamycin (the ted genes). Using the ted cluster in WAC04657 as a reference, we found related clusters in three other organisms: Streptomyces atroolivaceus ATCC 19725, Streptomyces globisporus NRRL B-2293, and Streptomyces sp. strain LaPpAH-202. Comparing the four clusters allowed us to identify the cluster boundaries. Genetic manipulation of the cluster confirmed the involvement of the ted genes in 13-deoxytetrodecamycin biosynthesis and revealed several additional molecules produced through the ted biosynthetic pathway, including tetrodecamycin, dihydrotetrodecamycin, and another, W5.9, a novel molecule. Comparison of the bioactivities of these four molecules suggests that they may act through the covalent modification of their target(s). Importance: The tetrodecamycins are a distinct subgroup of the tetronate family of secondary metabolites. Little is known about their biosynthesis or mechanisms of action, making them an attractive subject for investigation. In this paper we present the biosynthetic gene cluster for 13-deoxytetrodecamycin in Streptomyces sp. strain WAC04657. We identify related clusters in several other organisms and show that they produce related molecules.
2. Tetrodecamycin: An unusual and interesting tetronate antibiotic
Tomas Gverzdys, Glenna Kramer, Justin R Nodwell Bioorg Med Chem. 2016 Dec 15;24(24):6269-6275. doi: 10.1016/j.bmc.2016.05.028. Epub 2016 May 18.
The tetrodecamycins are a group of secondary metabolites that are characterized by the presence of a tetronate ring in their structure. Originally discovered for their antibiotic activity against Photobacterium damselae ssp. piscicida, the causative agent of pseudotuberculosis in fish, this family of molecules has also been shown to have potent antibiotic activity against methicillin-resistant Staphylococcus aureus. Due to their small size and highly cyclized nature, they represent an unusual member of the much larger group of bioactive molecules called the tetronates. Herein, we review what is known about the mechanism of action of these molecules and also present a hypothesis for their biosynthesis. A deeper understanding of the tetrodecamycins will provide a more holistic view of the tetronate-family, provide new chemical probes of bacterial biology, and may provide therapeutic lead molecules.
3. Tetrodecadazinone, a novel tetrodecamycin-pyridazinone hybrid with anti-liver fibrosis activity from Streptomyces sp. HU051
Ruo-Xi Liu, Shi-Fan Ma, Yi-Li Chen, Lie-Feng Ma, Ji-Dong Wang, Zha-Jun Zhan Bioorg Chem. 2022 Feb;119:105573. doi: 10.1016/j.bioorg.2021.105573. Epub 2021 Dec 16.
Tetrodecadazinone (1), a novel tetrodecamycin-pyridazinone hybrid possessing a new 1,2-dimethyl-1-(2-methylnonyl)decahydronaphthalene skeleton, and 4-hydroxydihydrotetrodecamycin (2) were separated from a culture of Streptomyces sp. HU051, together with a known compound, dihydrotetrodecamycin (3). Diverse spectroscopic approaches were applied to assign the structures of 1-3, and the structure of 1 was further confirmed by single crystal X-ray diffraction analysis. Compound 1 is the first example of a pyridazinone-containing natural product. Biosynthetically, 1 is proposed to be derived from a Michael addition reaction of a PKS-derived tetrodecamycin and a piperazic-acid-derived pyridazinone. Biological evaluation revealed 1 could reduce the expressions of extracellular matrix proteins (fibronectin and collagen I) and α-smooth muscle actin (α-SMA) in transforming growth factor-β (TGF-β1)-activated LX-2 cells. Preliminary mechanism study showed 1 exerted its anti-liver fibrosis effect by regulating TGF-β1/Smad2/3 signaling pathway.
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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 ╳
