Dihydrotetrodecamycin
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| Category | Antibiotics |
| Catalog number | BBF-01144 |
| CAS | 166403-10-7 |
| Molecular Weight | 336.38 |
| Molecular Formula | C18H24O6 |
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Description
It is produced by the strain of Streptomyces nashvillensis MJ885-mF8. Dihydrotetrodecamycin 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. Dihydrotetrodecamycin has weak antibacterial activity.
Specification
| Synonyms | 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-3,11,13-trimethyl-, (3R-(3R*,5R*,6S*,6ar*,10ar*,11S*,13R*))- |
| IUPAC Name | (1R,2S,7S,8R,9S,12S,17S)-7,8-dihydroxy-1,12,17-trimethyl-10,13-dioxatetracyclo[7.7.1.02,7.011,15]heptadec-11(15)-ene-14,16-dione |
| Canonical SMILES | CC1C2C(C3(CCCCC3C1(C(=O)C4=C(O2)C(OC4=O)C)C)O)O |
| InChI | InChI=1S/C18H24O6/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,4-7H2,1-3H3/t8-,9+,10+,12+,15-,17-,18+/m1/s1 |
| InChI Key | UMVGVJGZMKQXJC-YRWKBYQYSA-N |
Properties
| Appearance | Amorphous Powder |
| Antibiotic Activity Spectrum | gram-posotive becteria |
| Boiling Point | 521.2 °C at 760 mmHg |
| Melting Point | 200-203 °C |
| Density | 1.35 g/cm3 |
| Solubility | Soluble in Methanol |
Reference Reading
1. Tetrodecamycin and dihydrotetrodecamycin, new antimicrobial antibiotics against Pasteurella piscicida produced by Streptomyces nashvillensis MJ885-mF8. II. Structure determination
T Tsuchida, H Iinuma, R Sawa, Y Takahashi, H Nakamura, K T Nakamura, T Sawa, H Naganawa, T Takeuchi J Antibiot (Tokyo). 1995 Oct;48(10):1110-4. doi: 10.7164/antibiotics.48.1110.
Novel antimicrobial antibiotics against Pasteurella piscicida, tetrodecamycin (1) and weakly active dihydrotetrodecamycin (2) were isolated from a culture broth of Streptomyces nashvillensis MJ885-mF8. The planar structure of 1 was determined to be 2-acyl-4-ylidene tetronic acid alkyl ether containing decaline ring by various NMR spectral data of 1 and its acetyl derivative (3). The structure of 2 was elucidated by comparison with the spectral data of 1 and confirmed by catalytic reduction of 1 into 2. The X-ray crystallography of 2 showed the relative stereochemistry. Their absolute configurations were determined by using modified Mosher's method.
2. 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.
3. 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.
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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 ╳
