TMC-256A1
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| Category | Enzyme inhibitors |
| Catalog number | BBF-02546 |
| CAS | 3773-18-0 |
| Molecular Weight | 272.25 |
| Molecular Formula | C15H12O5 |
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Description
TMC-256A1 is an inhibitor of IL-4 signal transduction isolated from the fermentation broth of Aspergillus niger var niger TC 1629. It inhibited the IL-4 driven luciferase activity with IC50 values of 25 μmol/L.
Specification
| Synonyms | TMC-256 A1 |
| IUPAC Name | 4,5-dihydroxy-6-methoxy-2-methylbenzo[g]chromen-8-one |
| Canonical SMILES | CC1=CC(=C2C(=CC3=CC(=O)C=C(C3=C2O)OC)O1)O |
| InChI | InChI=1S/C15H12O5/c1-7-3-10(17)14-12(20-7)5-8-4-9(16)6-11(19-2)13(8)15(14)18/h3-6,17-18H,1-2H3 |
| InChI Key | BPQLYWBWGLXAIY-UHFFFAOYSA-N |
Properties
| Appearance | Yellow Powder |
Reference Reading
1. Mycobacterium smegmatis alters the production of secondary metabolites by marine-derived Aspergillus niger
Takahiro Jomori, Yasumasa Hara, Miho Sasaoka, Kazuo Harada, Andi Setiawan, Kazumasa Hirata, Atsushi Kimishima, Masayoshi Arai J Nat Med. 2020 Jan;74(1):76-82. doi: 10.1007/s11418-019-01345-0. Epub 2019 Jul 18.
It is generally accepted that fungi have a number of dormant gene clusters for the synthesis of secondary metabolites, and the activation of these gene clusters can expand the diversity of secondary metabolites in culture. Recent studies have revealed that the mycolic acid-containing bacterium Tsukamurella pulmonis activates dormant gene clusters in the bacterial genus Streptomyces. However, it is not clear whether the mycolic acid-containing bacteria activate dormant gene clusters of fungi. We performed co-culture experiments using marine-derived Aspergillus niger with Mycobacterium smegmatis, a mycolic acid-containing bacteria. The co-cultivation resulted in the production of a pigment by A. niger and increased cytotoxic activity of the extract against human prostate cancer DU145 cells. An analysis of secondary metabolites in the extract of the co-culture broth revealed that the increase in cytotoxic activity was caused by the production of malformin C (1), and that TMC-256A1 (2), desmethylkotanin (3), and aurasperone C (4) were selectively produced under co-culture conditions. In addition, further study suggested that direct interaction between the two microorganisms was necessary for the production of the pigment and the cytotoxic compound malformin C (1) from A. niger. Given the biological activities of malformin C, including cytotoxic activity, our approach for increasing the production of bioactive secondary metabolites has important practical applications and may facilitate structural analyses of novel bioactive compounds.
2. Capillasterin A, a Novel Pyrano[2,3-f]chromene from the Australian Crinoid Capillaster multiradiatus
Kah Yean Lum, Anthony R Carroll, Merrick G Ekins, Silven Read, Zahra Haq, Ian Tietjen, James St John, Rohan A Davis Mar Drugs. 2019 Jan 4;17(1):26. doi: 10.3390/md17010026.
Capillasterin A (1), a novel pyrano[2,3-f]chromene, together with seven known naphthopyrones including comaparvin (2), TMC-256C1 (3), 6-methoxycomaparvin-5- methyl ether (4), 5,8-dihydroxy-6-methoxy-2-propyl-4H-naphtho[2,3-b]pyran-4-one (5), 5,8-dihydroxy-6,10-dimethoxy-2-propyl-4H-naphtho[2,3-b]pyran-4-one (6), TMC-256A1 (7) and 6-methoxycomaparvin (8) were isolated from an EtOH/H₂O extract from the Australian crinoid Capillaster multiradiatus. The structures of all the compounds were determined by detailed spectroscopic (1D/2D NMR and MS) data analysis. This is the first report of a natural product that contains the pyrano[2,3-f]chromene skeleton. Compounds 2⁻6 were observed to display moderate inhibition of in vitro HIV-1 replication in a T cell line with EC50 values ranging from 7.5 to 25.5 µM without concomitant cytotoxicity.
3. Induced production of 6,9-dibromoflavasperone, a new radical scavenging naphthopyranone in the marine-mudflat-derived fungus Aspergillus niger
Alain Simplice Leutou, Keumja Yun, Byeng Wha Son Arch Pharm Res. 2016 Jun;39(6):806-10. doi: 10.1007/s12272-016-0764-2. Epub 2016 May 31.
The addition of metal bromides (NaBr and CaBr2) during fermentation of the marine-mudflat-derived fungus Aspergillus niger induced production of a new radical scavenging brominated naphthopyranone, 6,9-dibromoflavasperone (1); and three known naphtho-γ-pyranone monomers, flavasperone (2), TMC-256A1 (3), and fonsecin (4); and one naphtho-γ-pyranone dimer, aurasperone B (5). The structure of 6,9-dibromoflavasperone (1) was assigned through the combination of spectroscopic data analyses and comparison with the spectral data of flavasperone (2). Compounds 1-5 displayed potent radical scavenging activity against 2,2-diphenyl-1-picrylhydrazyl, with IC50 values of 21, 25, 0.3, 0.02, and 0.01 μM, respectively, and 3-5 were more potent than the positive control, ascorbic acid (IC50, 20.0 μM).
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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 ╳
