Asterric acid
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| Category | Enzyme inhibitors |
| Catalog number | BBF-00570 |
| CAS | 577-64-0 |
| Molecular Weight | 348.30 |
| Molecular Formula | C17H16O8 |
| Purity | >98% |
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Description
Asterric acid is an Endothelin (ET) binding inhibitor produced by Aspergillus sp.
Specification
| Synonyms | Dimethylosoic acid,TAN 1415A, WF 12880A |
| Storage | Store at -20°C |
| IUPAC Name | 2-hydroxy-6-(4-hydroxy-2-methoxy-6-methoxycarbonylphenoxy)-4-methylbenzoic acid |
| Canonical SMILES | CC1=CC(=C(C(=C1)OC2=C(C=C(C=C2OC)O)C(=O)OC)C(=O)O)O |
| InChI | InChI=1S/C17H16O8/c1-8-4-11(19)14(16(20)21)12(5-8)25-15-10(17(22)24-3)6-9(18)7-13(15)23-2/h4-7,18-19H,1-3H3,(H,20,21) |
| InChI Key | XOKVHFNTYHPEHN-UHFFFAOYSA-N |
| Source | Aspergillus terreus |
Properties
| Appearance | Powder |
| Boiling Point | 557.6°C at 760 mmHg |
| Melting Point | 208-214°C |
| Density | 1.406 g/cm3 |
| Solubility | Soluble in DMSO |
Reference Reading
1. Bioactive asterric acid derivatives from the Antarctic ascomycete fungus Geomyces sp
Lihua Jiang, Yongsheng Che, Shuchun Liu, Bingda Sun, Yan Li, Xingzhong Liu, Hua Zhang J Nat Prod . 2008 Sep;71(9):1643-6. doi: 10.1021/np8003003.
Five new asterric acid derivatives, ethyl asterrate (3), n-butyl asterrate (4), and geomycins A-C (6-8), have been isolated from cultures of an isolate of the Antarctic ascomycete fungus Geomyces sp. The structures of these metabolites were elucidated by NMR spectroscopy. The absolute configuration of 8 was determined by application of the CD excitation chirality method. Compound 7 displayed antifungal activity against Aspergillus fumigatus, whereas 8 showed antimicrobial activities against gram-positive and gram-negative bacteria.
2. Antibacterial and antioxidant metabolites from the insect-associated fungus Aspergillus fumigatus
Zhi-Fei Chen, Dan-Dan Meng, Tian-Xiao Li, Chun-Ping Xu, Ying Wang, Pu Zhang, Jian-Qiang Zheng Pak J Pharm Sci . 2021 May;34(3(Special)):1271-1276.
The research on bioactive secondary metabolites from Aspergillus fumigatus afforded six compounds, which were identified by mass spectrometer (MS) and nuclear magnetic resonance (NMR) spectroscopic analysis as cyclopyazonic acid (1), trypacidin A (2), asterric acid (3), methyl asterrate (4), demethylcitreoviranol (5), as well as (5-hydroxy-2-oxo-2H-pyran-4-yl) methyl acetate (6). Cyclopyazonic acid (1) was found to have potent antibacterial effects, especially against Bacillus licheniformis with minimal inhibitory concentration (MIC) value of 3.7μg/mL. Its antibacterial effects were possibly related to the olefinic acid group in the structure. Phenyl ether derivatives 3 and 4, and trypacidin A (2) also exhibited antimicrobial effects. In addition, compound 6 showed significant antioxidant effects with half maximal effective concentration (EC50) value of 10.2μM in the ABTS (2,2-azino-bis-3-ethylbenzothiazoline-6-sulfonic acid) assay, which was better than the positive control.
3. Exploring the extremes: applying high concentration of yeast extract leads to drastic morphological changes and elimination of (+)-geodin and asterric acid production in Aspergillus terreus submerged cultures
Tomasz Boruta, Ida Stefaniak, Marcin Bizukojć, Iwona Grzybowska, Adrianna Górnicka Biotechnol Lett . 2021 Jan;43(1):61-71. doi: 10.1007/s10529-020-03018-5.
Objective:Evaluation of morphology and secondary metabolites production in Aspergillus terreus ATCC 20542 cultures over a wide range of lactose and yeast extract concentrations from 0.2 up to an extremely high level of 200 g l-l.Results:The morphological differences of mycelial objects were quantified with the use of morphological parameters calculated by applying the tools of digital image analysis. At 200 g l-lof yeast extract clumps and loose hyphae were recorded instead of pellets commonly observed in submerged cultures of A. terreus. Under these conditions the biosynthesis of (+)-geodin and asterric acid was totally blocked, lovastatin formation was found to be at a relatively low level and biomass production turned out to be greater than in the remaining variants, where the pelleted growth was observed. At 200 g l-lof lactose the production of lovastatin, (+)-geodin and asterric acid was visibly stimulated compared to the media containing 0.2, 2 and 20 g l-lof the sugar substrate, but at the same time no traces of butyrolactone I could be detected in the broth. Lactose at the extremely high concentration of 200 g l-ldid not induce the drastic morphological changes observed in the case of 200 g l-1of yeast extract. It was proved that at the C/N values as low as 4 and as high as 374 A. terreus not only continued to display growth but also exhibited the production of secondary metabolites. The use of cultivation media representing the equivalent C/N ratios led to different metabolic and morphological outcomes depending on the concentration of lactose and yeast extract that contributed to the given C/N value.Conclusion:The extremely high concentration of yeast extract leads to marked morphological changes of A. terreus and the elimination of (+)-geodin and asterric production, while applying the excess of lactose is stimulatory in terms of lovastatin production.
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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 ╳
