A-80915 A
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| Category | Antibiotics |
| Catalog number | BBF-03167 |
| CAS | 127875-60-9 |
| Molecular Weight | 529.88 |
| Molecular Formula | C26H31Cl3O5 |
| Purity | >98% |
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Description
A-80915 A is a naphthoquinone antibiotic produced by Streptomyces aculeolatus A80915. Activity against gram-positive bacteria.
Specification
| Synonyms | 2H-Naphtho(2,3-b)pyran-5,10-dione, 3,4a-dichloro-10a-((3-chloro-2,2-dimethyl-6-methylenecyclohexyl)methyl)-3,4,4a,10a-tetrahydro-6,8-dihydroxy-2,2,7-trimethyl- |
| Storage | Store at -20°C |
| IUPAC Name | 3,4a-dichloro-10a-[(3-chloro-2,2-dimethyl-6-methylidenecyclohexyl)methyl]-6,8-dihydroxy-2,2,7-trimethyl-3,4-dihydrobenzo[g]chromene-5,10-dione |
| Canonical SMILES | CC1=C(C=C2C(=C1O)C(=O)C3(CC(C(OC3(C2=O)CC4C(=C)CCC(C4(C)C)Cl)(C)C)Cl)Cl)O |
| InChI | InChI=1S/C26H31Cl3O5/c1-12-7-8-17(27)23(3,4)15(12)10-26-21(32)14-9-16(30)13(2)20(31)19(14)22(33)25(26,29)11-18(28)24(5,6)34-26/h9,15,17-18,30-31H,1,7-8,10-11H2,2-6H3 |
| InChI Key | JCIYFFNGTHMEDE-UHFFFAOYSA-N |
Properties
| Appearance | Light Yellow Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Boiling Point | 684.9°C at 760 mmHg |
| Density | 1.37 g/cm3 |
| Solubility | Soluble in DMSO |
Reference Reading
1. Napyradiomycin A4 and Its Relate Compounds, a New Anti-PRV Agent and Their Antibacterial Activities, from Streptomyces kebangsaanensis WS-68302
Yani Zhang, Wei Fang, Kaimei Wang, Zhigang Zhang, Zhaoyuan Wu, Liqiao Shi, Fang Liu, Zhongyi Wan, Manli Liu Molecules. 2023 Jan 8;28(2):640. doi: 10.3390/molecules28020640.
Two new napyradiomycins derivatives, napyradiomycin A4 (1) and A80915 H (2), along with five known ones, were isolated from the ethyl acetate extract of fermentation culture of Streptomyces kebangsaanensis WS-68302. Their structures were elucidated by extensive spectroscopic analysis, including HR-MS, 1D and 2D NMR, CD spectrum, as well as comparison with literature data. Compound 1 exhibited significant antiviral activity against PRV (Pseudorabies virus) with an IC50 value of 2.056 μM and therapeutic ratio at 14.98, suggesting that it might have potential for development of an antiviral agent. Moreover, compound 1 displayed the strongest inhibition against PRV protein among the tested napyradiomycins in the indirect immunofuorescence assay. Compounds 3 and 4 showed higher activities against swine pathogenic Streptococcus suis than the positive control penicillin G sodium salt, with MIC values of 3.125 and 6.25 μg/mL, respectively. Compounds 1 and 3-6 exhibited moderate antibacterial activity against the swine pathogenic Erysipelothrix rhusiopathiae, with MIC values ranging from 25 to 50 μg/mL.
2. Natural products containing a diazo group
Christopher C Nawrat, Christopher J Moody Nat Prod Rep. 2011 Aug;28(8):1426-44. doi: 10.1039/c1np00031d. Epub 2011 May 18.
Although diazo compounds are probably best known for their involvement as versatile intermediates in modern synthetic organic chemistry, a small number of such compounds also occur naturally. Many of the early examples, such as azaserine, originally isolated in the 1950s, have antitumour properties and consist of modified α-amino acids. More recently, other more complex diazo compounds have been isolated from natural sources, and these include diazobenzoquinones, diazonaphthoquinones, such as the SF2415 and A80915 antibiotics, and the diazofluorene-based kinamycins and lomaiviticins. This report will cover the isolation, biosynthesis, biological activity and synthesis of natural products containing a diazo group.
3. TMKS8A, an antibacterial and cytotoxic chlorinated α-lapachone, from a sea slug-derived actinomycete of the genus Streptomyces
Zhiwei Zhang, Mada Triandala Sibero, Akiho Kai, Keisuke Fukaya, Daisuke Urabe, Yasuhiro Igarashi J Antibiot (Tokyo). 2021 Jul;74(7):464-469. doi: 10.1038/s41429-021-00415-4. Epub 2021 Mar 11.
TMKS8A (1), a new chlorinated α-lapachone derivative, along with five known related metabolites, A80915 C (2), SF2415B1 (3), chlorinated dihydroquinone 3 (4), SF2415B3 (5), and A80915 C (6), were identified from the culture extract of Streptomyces sp. TMKS8, which was isolated from a sea slug, Paromoionchis tumidus. The structure of 1 was determined by the analysis of NMR and MS spectral data, assisted by NMR chemical shift prediction using DFT-based calculation. The absolute configuration was determined to be R by comparison of experimental and calculated ECD spectra. Compound 1 displayed antimicrobial activity against Gram-positive bacteria with MIC values ranging from 6.25 to 12.5 μg ml-1 and cytotoxicity against murine leukemia P388 cells with IC50 9.8 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 ╳
