Neoxaline
目录号 : GC45524
A fungal metabolite
Cas No.:909900-78-3
Sample solution is provided at 25 µL, 10mM.
;)
,-1-7$$$37316672.jpg');)
;)
;)
$$$36806353.jpg');)
;33(7)%EF%BC%9A546-561$$$37156877.jpg');)
;)
;)
;)
%201124-1138.$$$35908550.jpg');)
%20766-780.$$$37100057.jpg');)
%20418-432.$$$36893736.jpg');)
%EF%BC%9A-240-255.$$$35108512.jpg');)
533-545$$$36543525.jpg');)
%201-13.$$$36600053.jpg');)
;)
Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Neoxaline is an alkaloid fungal metabolite originally isolated from A. japonicus.1
References
1. Hirano, A., Iwai, Y., Masuma, R., et al. Neoxaline, a new alkaloid produced by Aspergillus japonicus. Production, isolation and properties. J. Antibiot. (Tokyo) 32(8), 781-785 (1979).
| Cas No. | 909900-78-3 | SDF | |
| Canonical SMILES | CON(C1=C2C=CC=C1)[C@]34[C@@]2(C(C)(C)C=C)C[C@H](O)C(N3/C(C(N4)=O)=C/C5=CN=CN5)=O | ||
| 分子式 | C23H25N5O4 | 分子量 | 435.5 |
| 溶解度 | Methanol: 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。 |
||
| 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 | |||
 |
1 mg | 5 mg | 10 mg |
| 1 mM | 2.2962 mL | 11.4811 mL | 22.9621 mL |
| 5 mM | 0.4592 mL | 2.2962 mL | 4.5924 mL |
| 10 mM | 0.2296 mL | 1.1481 mL | 2.2962 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。
Asymmetric total synthesis of Neoxaline
J Am Chem Soc 2013 Aug 28;135(34):12568-71.PMID:23957424DOI:10.1021/ja406657v.
A first asymmetric total synthesis and determination of the absolute configuration of Neoxaline has been accomplished through the highly stereoselective introduction of a reverse prenyl group to create a quaternary carbon stereocenter using (-)-3a-hydroxyfuroindoline as a building block, construction of the indoline spiroaminal via cautious stepwise oxidations with cyclizations from the indoline, assembly of (Z)-dehydrohistidine, and photoisomerization of unnatural (Z)-neoxaline to the natural (E)-neoxaline as the key steps.
Neoxaline, a new alkaloid produced by Aspergillus japonicus. Production, isolation and properties
J Antibiot (Tokyo) 1979 Aug;32(8):781-5.PMID:500498DOI:10.7164/antibiotics.32.781.
A new alkaloid named Neoxaline has been isolated from culture broth of Aspergillus japonicug Fg-551 by solvent extraction and silica gel chromatography. The compound does not possess antimicrobial activities, but weakly stimulates the central nervous system. The molecular formula of Neoxaline has been determined as C23H25N5O4 on the basis of elemental analysis and its mass spectrometry.
Evolutionary formation of gene clusters by reorganization: the meleagrin/roquefortine paradigm in different fungi
Appl Microbiol Biotechnol 2016 Feb;100(4):1579-1587.PMID:26668029DOI:10.1007/s00253-015-7192-y.
The biosynthesis of secondary metabolites in fungi is catalyzed by enzymes encoded by genes linked in clusters that are frequently co-regulated at the transcriptional level. Formation of gene clusters may take place by de novo assembly of genes recruited from other cellular functions, but also novel gene clusters are formed by reorganization of progenitor clusters and are distributed by horizontal gene transfer. This article reviews (i) the published information on the roquefortine/meleagrin/Neoxaline gene clusters of Penicillium chrysogenum (Penicillium rubens) and the short roquefortine cluster of Penicillium roqueforti, and (ii) the correlation of the genes present in those clusters with the enzymes and metabolites derived from these pathways. The P. chrysogenum roq/mel cluster consists of seven genes and includes a gene (roqT) encoding a 12-TMS transporter protein of the MFS family. Interestingly, the orthologous P. roquefortine gene cluster has only four genes and the roqT gene is present as a residual pseudogene that encodes only small peptides. Two of the genes present in the central region of the P. chrysogenum roq/mel cluster have been lost during the evolutionary formation of the short cluster and the order of the structural genes in the cluster has been rearranged. The two lost genes encode a N1 atom hydroxylase (nox) and a roquefortine scaffold-reorganizing oxygenase (sro). As a consequence P. roqueforti has lost the ability to convert the roquefortine-type carbon skeleton to the glandicoline/meleagrin-type scaffold and is unable to produce glandicoline B, meleagrin and Neoxaline. The loss of this genetic information is not recent and occurred probably millions of years ago when a progenitor Penicillium strain got adapted to life in a few rich habitats such as cheese, fermented cereal grains or silage. P. roqueforti may be considered as a "domesticated" variant of a progenitor common to contemporary P. chrysogenum and related Penicillia.
A concise stereoselective route to the indoline spiroaminal framework of Neoxaline and oxaline
Org Lett 2005 Mar 3;7(5):941-3.PMID:15727480DOI:10.1021/ol050077y.
The stereoselective synthesis of tetracyclic intermediate, the indoline spiroaminal 3 for Neoxaline (1) and oxaline (2), has been accomplished. The key step of the stereoselective synthesis of 3 was the Lewis acid mediated transcyclization of 4 to the diaminal 18, and the tungstate-catalyzed oxidation of 18 to obtain the nitrone 19, which easily cyclizes to the indoline spiroaminal framework 3. [structure: see text]
Novel key metabolites reveal further branching of the roquefortine/meleagrin biosynthetic pathway
J Biol Chem 2013 Dec 27;288(52):37289-95.PMID:24225953DOI:10.1074/jbc.M113.512665.
Metabolic profiling and structural elucidation of novel secondary metabolites obtained from derived deletion strains of the filamentous fungus Penicillium chrysogenum were used to reassign various previously ascribed synthetase genes of the roquefortine/meleagrin pathway to their corresponding products. Next to the structural characterization of roquefortine F and Neoxaline, which are for the first time reported for P. chrysogenum, we identified the novel metabolite roquefortine L, including its degradation products, harboring remarkable chemical structures. Their biosynthesis is discussed, questioning the exclusive role of glandicoline A as key intermediate in the pathway. The results reveal that further enzymes of this pathway are rather unspecific and catalyze more than one reaction, leading to excessive branching in the pathway with meleagrin and Neoxaline as end products of two branches.