Aureothin
(Synonyms: 金链菌素) 目录号 : GC42874
A polyketide antibiotic that inhibits oxidoreductase
Cas No.:2825-00-5
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >96.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Aureothin is a natural nitroaryl-substituted polyketide that exhibits antitumor, antifungal, and insecticidal activities. It is a non-competitive inhibitor of NADH:ubiquinone oxidoreductase of bovine heart, N. crassa, and E. coli (IC50s = 0.07, 0.08, and 22 nmol/mg protein, respectively).
| Cas No. | 2825-00-5 | SDF | |
| 别名 | 金链菌素 | ||
| Canonical SMILES | CC(/C=C1CO[C@@H](C(OC(OC)=C2C)=C(C)C2=O)C\1)=C\C3=CC=C([N+]([O-])=O)C=C3 | ||
| 分子式 | C22H23NO6 | 分子量 | 397.4 |
| 溶解度 | DMF: soluble,DMSO: soluble,Ethanol: soluble | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 2.5164 mL | 12.5818 mL | 25.1636 mL |
| 5 mM | 0.5033 mL | 2.5164 mL | 5.0327 mL |
| 10 mM | 0.2516 mL | 1.2582 mL | 2.5164 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
A novel Aureothin diepoxide derivative from Streptomyces sp. NIIST-D31 strain
J Antibiot (Tokyo) 2022 Sep;75(9):491-497.PMID:35922482DOI:10.1038/s41429-022-00547-1.
A novel vicinal diepoxide of alloaureothin was isolated from Streptomyces sp. NIIST-D31 strain along with three carboxamides, p-aminobenzoic acid and 1,6-dimethoxyphenazine. Exhaustive 2D NMR analysis and analysis of experimental, theoretical CD spectra aided in establishing the structure of compound 1. Compound 1 inhibits adipogenesis and accumulation of lipid droplets during the differentiation of 3T3-L1 cells.
Evolution of metabolic diversity in polyketide-derived pyrones: using the non-colinear Aureothin assembly line as a model system
Phytochemistry 2009 Oct-Nov;70(15-16):1833-40.PMID:19651421DOI:10.1016/j.phytochem.2009.05.022.
Polyketide-derived pyrones are structurally diverse secondary metabolites that are represented in all three kingdoms of life and are endowed with various biological functions. The Aureothin family of Streptomyces metabolites was chosen as a model to study the factors governing structural diversity and the evolutionary processes involved. This review highlights recent insights into the non-colinear Aureothin and neoaureothin modular type I polyketide synthase (PKS), aromatic starter unit biosynthesis, polyketide tailoring reactions, and a non-enzymatic polyene splicing cascade. Pyrone biosynthesis in bacteria, fungi, and plants is compared. Finally, various strategies to increase metabolic diversity of Aureothin derivatives through mutasynthesis, pathway engineering, and biotransformation are presented. The unusual Aureothin and neoaureothin assembly lines thus not only represent a model for PKS evolution, but provided important insights into non-canonical enzymatic processes that could be employed for the production of antitumor and antifungal agents.
Streptomyces distallicus, a Potential Microbial Biolarvicide
J Agric Food Chem 2022 Sep 14;70(36):11274-11280.PMID:36040208DOI:10.1021/acs.jafc.2c03537.
Infected mosquitos from the genus Aedes have become one of the world's most influential contributors to human morbidity and death. To explore new biopesticides with activity against Aedes aegypti, Streptomyces distallicus, a species related to the subspecies group of Streptomyces netropsis, was investigated. Six metabolites, Aureothin, allo-aureothin, deoxyaureothin, 4',7-dihydroxy isoflavone, 2-methyl-5-(3-indolyl)oxazole, and 2-ethyl-5-(3-indolyl)oxazole were isolated, and chemical structures, were elucidated based on one- and two-dimensional NMR spectroscopy analyses and HRMS. The A. aegypti larvicidal activity of these compounds was evaluated. Only two isomeric compounds, Aureothin and allo-aureothin, showed larvicidal activity against A. aegypti with LC50 values of 1.5 and 3.1 ppm for 24 h post-treatment, respectively, and 3.8 and 7.4 ppm for 48 h post-treatment, respectively. The crude extract of S. distallicus also demonstrated potent larvicidal activity with LC50 values of 1.46 and 1.2 ppm for 24 and 48 h post-treatment, respectively. Deoxyaureothin, a furan ring reduced form of Aureothin, showed no activity against A. aegypti. The hybrid imported fire ants activity of Aureothin was also evaluated, but it did not show any activity at the highest dose of 62.5 μg/g. Described here is the first report on a bioassay-directed investigation of the secondary metabolites of S. distallicus and biological evaluation of isolated compounds Aureothin and its isomer and intermediates as potential microbial larvicides. S. distallicus and crude extracts thereof are a promising source of potential microbial biolarvicides.
Emulating evolutionary processes to morph aureothin-type modular polyketide synthases and associated oxygenases
Nat Commun 2019 Sep 2;10(1):3918.PMID:31477708DOI:10.1038/s41467-019-11896-1.
Polyketides produced by modular type I polyketide synthases (PKSs) play eminent roles in the development of medicines. Yet, the production of structural analogs by genetic engineering poses a major challenge. We report an evolution-guided morphing of modular PKSs inspired by recombination processes that lead to structural diversity in nature. By deletion and insertion of PKS modules we interconvert the assembly lines for related antibiotic and antifungal agents, Aureothin (aur) and neoaureothin (nor) (aka spectinabilin), in both directions. Mutational and functional analyses of the polyketide-tailoring cytochrome P450 monooxygenases, and PKS phylogenies give contradictory clues on potential evolutionary scenarios (generalist-to-specialist enzyme evolution vs. most parsimonious ancestor). The KS-AT linker proves to be well suited as fusion site for both excision and insertion of modules, which supports a model for alternative module boundaries in some PKS systems. This study teaches important lessons on the evolution of PKSs, which may guide future engineering approaches.
New discovery on the nematode activity of Aureothin and alloaureothin isolated from endophytic bacteria Streptomyces sp. AE170020
Sci Rep 2022 Mar 10;12(1):3947.PMID:35273247DOI:10.1038/s41598-022-07879-w.
Endophytic bacteria, a rich source of bioactive secondary metabolites, are ideal candidates for environmentally benign agents. In this study, an endophytic strain, Streptomyces sp. AE170020, was isolated and selected for the purification of nematicidal substances based on its high nematicidal activity. Two highly active components, Aureothin and alloaureothin, were identified, and their chemical structures were determined using spectroscopic analysis. Both compounds suppressed the growth, reproduction, and behavior of Bursaphelenchus xylophilus. In in vivo experiments, the extracts of strain Streptomyces sp. AE170020 effectively suppressed the development of pine wilt disease in 4-year-old plants of Pinus densiflora. The potency of secondary metabolites isolated from endophytic strains suggests applications in controlling Bursaphelenchus xylophilus and opens an avenue for further research on exploring bioactive substances against the pine wood nematode.