Asperlin
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| Category | Antibiotics |
| Catalog number | BBF-00568 |
| CAS | 30387-51-0 |
| Molecular Weight | 212.20 |
| Molecular Formula | C10H12O5 |
| Purity | >98% |
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Description
Asperlin is an antibiotic produced by Aspergillus nidulans CMI 94163. Asperlin has anti-gram-positive bacteria, negative bacteria, mycobacterial activity, and inhibits KB cells.
Specification
| Synonyms | Asperlin; U 13933 |
| Storage | Store at -20°C |
| IUPAC Name | [(2R,3S)-2-[(2S,3R)-3-methyloxiran-2-yl]-6-oxo-2,3-dihydropyran-3-yl] acetate |
| Canonical SMILES | CC1C(O1)C2C(C=CC(=O)O2)OC(=O)C |
| InChI | InChI=1S/C10H12O5/c1-5-9(13-5)10-7(14-6(2)11)3-4-8(12)15-10/h3-5,7,9-10H,1-2H3/t5-,7+,9+,10-/m1/s1 |
| InChI Key | SPKNARKFCOPTSY-XWPZMVOTSA-N |
Properties
| Appearance | Colorless Crystal |
| Antibiotic Activity Spectrum | fungi |
| Boiling Point | 360.4°C at 760 mmHg |
| Density | 1.28 g/cm3 |
| Solubility | Soluble in Water |
Reference Reading
1. Biocontrol Potential of Aspergillus Species Producing Antimicrobial Metabolites
Men Thi Ngo, Minh Van Nguyen, Jae Woo Han, Bomin Kim, Yun Kyung Kim, Myung Soo Park, Hun Kim, Gyung Ja Choi Front Microbiol. 2021 Dec 23;12:804333. doi: 10.3389/fmicb.2021.804333. eCollection 2021.
Microbial metabolites have been recognized as an important source for the discovery of new antifungal agents because of their diverse chemical structures with novel modes of action. In the course of our screening for new antifungal agents from microbes, we found that culture filtrates of two fungal species Aspergillus candidus SFC20200425-M11 and Aspergillus montenegroi SFC20200425-M27 have the potentials to reduce the development of fungal plant diseases such as tomato late blight and wheat leaf rust. From these two Aspergillus spp., we isolated a total of seven active compounds, including two new compounds (4 and 6), and identified their chemical structures based on the NMR spectral analyses: sphaeropsidin A (1), (R)-formosusin A (2), (R)-variotin (3), candidusin (4), asperlin (5), montenegrol (6), and protulactone A (7). Based on the results of the in vitro bioassays of 11 plant pathogenic fungi and bacteria, sphaeropsidin A (1), (R)-formosusin A (2), (R)-variotin (3), and asperlin (5) exhibited a wide range of antimicrobial activity. Furthermore, when plants were treated with sphaeropsidin A (1) and (R)-formosusin A (2) at a concentration of 500 μg/ml, sphaeropsidin A (1) exhibited an efficacy disease control value of 96 and 90% compared to non-treated control against tomato late blight and wheat leaf rust, and (R)-formosusin A (2) strongly reduced the development of tomato gray mold by 82%. Asperlin (5) at a concentration of 500 μg/ml effectively controlled the development of tomato late blight and wheat leaf rust with a disease control value of 95%. Given that culture filtrates and active compounds derived from two Aspergillus spp. exhibited disease control efficacies, our results suggest that the Aspergillus-produced antifungal compounds could be useful for the development of new natural fungicides.
2. Hybrid Transcription Factor Engineering Activates the Silent Secondary Metabolite Gene Cluster for (+)-Asperlin in Aspergillus nidulans
Michelle F Grau, Ruth Entwistle, Yi-Ming Chiang, Manmeet Ahuja, C Elizabeth Oakley, Tomohiro Akashi, Clay C C Wang, Richard B Todd, Berl R Oakley ACS Chem Biol. 2018 Nov 16;13(11):3193-3205. doi: 10.1021/acschembio.8b00679. Epub 2018 Oct 29.
Fungi are a major source of valuable bioactive secondary metabolites (SMs). These compounds are synthesized by enzymes encoded by genes that are clustered in the genome. The vast majority of SM biosynthetic gene clusters are not expressed under normal growth conditions, and their products are unknown. Developing methods for activation of these silent gene clusters offers the potential for discovering many valuable new fungal SMs. While a number of useful approaches have been developed, they each have limitations, and additional tools are needed. One approach, upregulation of SM gene cluster-specific transcription factors that are associated with many SM gene clusters, has worked extremely well in some cases, but it has failed more often than it has succeeded. Taking advantage of transcription factor domain modularity, we developed a new approach. We fused the DNA-binding domain of a transcription factor associated with a silent SM gene cluster with the activation domain of a robust SM transcription factor, AfoA. Expression of this hybrid transcription factor activated transcription of the genes in the target cluster and production of the antibiotic (+)-asperlin. Deletion of cluster genes confirmed that the cluster is responsible for (+)-asperlin production, and we designate it the aln cluster. Separately, coinduction of expression of two aln cluster genes revealed the pathway intermediate (2 Z,4 Z,6 E)-octa-2,4,6-trienoic acid, a compound with photoprotectant properties. Our findings demonstrate the potential of our novel synthetic hybrid transcription factor strategy to discover the products of other silent fungal SM gene clusters.
3. Asperlin Stimulates Energy Expenditure and Modulates Gut Microbiota in HFD-Fed Mice
Chongming Wu, Yue Zhou, Guihong Qi, Dong Liu, Xiaoxue Cao, Jiaqi Yu, Rong Zhang, Wenhan Lin, Peng Guo Mar Drugs. 2019 Jan 9;17(1):38. doi: 10.3390/md17010038.
Asperlin is a marine-derived, natural product with antifungal, anti-inflammatory and anti-atherosclerotic activities. In the present study, we showed that asperlin effectively prevented the development of obesity in high-fat diet (HFD)-fed mice. Oral administration of asperlin for 12 weeks significantly suppressed HFD-induced body weight gain and fat deposition without inhibiting food intake. Hyperlipidemia and liver steatosis were also substantially ameliorated. A respiratory metabolism monitor showed that asperlin efficiently increased energy expenditure and enhanced thermogenic gene expression in adipose tissue. Accordingly, asperlin-treated mice showed higher body temperature and were more tolerant of cold stress. Meanwhile, asperlin also increased the diversity and shifted the structure of gut microbiota. Oral administration of asperlin markedly increased the relative abundance of Bacteroidetes, leading to a higher Bacteroidetes-to-Fimicutes ratio. The HFD-induced abnormalities at both phylum and genus levels were all remarkably recovered by asperlin. These results demonstrated that asperlin is effective in preventing HFD-induced obesity and modulating gut microbiota. Its anti-obesity properties may be attributed to its effect on promoting energy expenditure.
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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 ╳
