Oxaline
目录号 : GC47846
An alkaloid fungal metabolite
Cas No.:55623-37-5
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >70.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Oxaline is an alkaloid fungal metabolite originally isolated from P. oxalicum.1
1.Nagel, D.W., Pachler, K.G.R., Steyn, P.S., et al.The chemistry and 13C NMR assignments of oxaline, a novel alkaloid from penicillium oxalicumTetrahedron32(21)2625-2631(1976)
| Cas No. | 55623-37-5 | SDF | |
| Canonical SMILES | CON(C1=C2C=CC=C1)[C@]34[C@@]2(C(C)(C)C=C)C=C(OC)C(N3/C(C(N4)=O)=C/C5=CN=CN5)=O | ||
| 分子式 | C24H25N5O4 | 分子量 | 447.5 |
| 溶解度 | Dichloromethane: soluble,DMSO: soluble,Ethanol: soluble,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。 |
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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 | 2.2346 mL | 11.1732 mL | 22.3464 mL |
| 5 mM | 0.4469 mL | 2.2346 mL | 4.4693 mL |
| 10 mM | 0.2235 mL | 1.1173 mL | 2.2346 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。
Anti-neuroinflammatory effect of Oxaline, isorhodoptilometrin, and 5-hydroxy-7-(2'-hydroxypropyl)-2-methyl-chromone obtained from the marine fungal strain Penicillium oxalicum CLC-MF05
Arch Pharm Res 2022 Feb;45(2):90-104.PMID:35094261DOI:10.1007/s12272-022-01370-w.
Penicillium is a rich source of bioactive compounds. Among all Penicillium species, Penicillium oxalicum has been reported to produce various types of secondary metabolites, including alkaloids, phenolics, and tetrahydroxanthone dimeric compounds, exhibiting many pharmacological effects, such as antiviral, antibacterial, and cytotoxic activities. Three secondary metabolites were isolated from a fermented culture of the sponge-associated fungal strain P. oxalicum CLC-MF05: Oxaline (1), isorhodoptilometrin (2), and 5-hydroxy-7-(2'-hydroxypropyl)-2-methyl-chromone (3). Their chemical structures were identified by 1D and 2D NMR and high-resolution mass spectroscopic analyses and compared with previously reported data. All three compounds inhibited NO and PGE2 overproduction and iNOS and COX-2 overexpression in both LPS-stimulated BV2 and rat primary microglia. These metabolites also repressed mRNA expression of TNF-α, IL-1β, IL-6, and IL-12. Further, mechanistic studies revealed that the inhibitory actions of compounds 1-3 were regulated by the inactivation of the NF-κB and MAPK signaling pathways. Furthermore, inactivation of the TLR4/MyD88 pathway contributed to the anti-neuroinflammatory activity of these compounds. These results suggest that compounds 1-3 represent potential anti-inflammatory candidates for the treatment of neurodegenerative diseases; however, further investigation is needed.
Oxaline, a fungal alkaloid, arrests the cell cycle in M phase by inhibition of tubulin polymerization
Biochim Biophys Acta 2004 Jul 23;1693(1):47-55.PMID:15276324DOI:10.1016/j.bbamcr.2004.04.013.
Oxaline and neoxaline, fungal alkaloids, were found to inhibit cell proliferation and to induce cell cycle arrest at the G(2)/M phase in Jurkat cells. CBP501 (a peptide corresponding to amino acids 211-221 of Cdc25C phosphatase), which inhibits the G(2) checkpoint, did not affect the G(2)/M arrest caused by Oxaline, suggesting that Oxaline causes M phase arrest but not G(2) phase arrest. The Cdc2 phosphorylation level of oxaline-treated cell lysate was lower than that of the control cells, indicating that Oxaline arrests the M phase. Oxaline disrupted cytoplasmic microtubule assembly in 3T3 cells. Furthermore, Oxaline inhibited polymerization of microtubule protein and purified tubulin dose-dependently in vitro. In a binding competition assay, Oxaline inhibited the binding of [(3)H]colchicine to tubulin, but not that of [(3)H]vinblastine. These results indicate that Oxaline inhibits tubulin polymerization, resulting in cell cycle arrest at the M phase.
Unveiling sequential late-stage methyltransferase reactions in the meleagrin/Oxaline biosynthetic pathway
Org Biomol Chem 2018 Sep 11;16(35):6450-6459.PMID:30141817DOI:10.1039/c8ob01565a.
Antimicrobial and anti-proliferative meleagrin and Oxaline are roquefortine C-derived alkaloids produced by fungi of the genus Penicillium. Tandem O-methylations complete the biosynthesis of Oxaline from glandicoline B through meleagrin. Currently, little is known about the role of these methylation patterns in the bioactivity profile of meleagrin and Oxaline. To establish the structural and mechanistic basis of methylation in these pathways, crystal structures were determined for two late-stage methyltransferases in the Oxaline and meleagrin gene clusters from Penicillium oxalicum and Penicillium chrysogenum. The homologous enzymes OxaG and RoqN were shown to catalyze penultimate hydroxylamine O-methylation to generate meleagrin in vitro. Crystal structures of these enzymes in the presence of methyl donor S-adenosylmethionine revealed an open active site, which lacks an apparent base indicating that catalysis is driven by proximity effects. OxaC was shown to methylate meleagrin to form Oxaline in vitro, the terminal pathway product. Crystal structures of OxaC in a pseudo-Michaelis complex containing sinefungin and meleagrin, and in a product complex containing S-adenosyl-homocysteine and Oxaline, reveal key active site residues with His313 serving as a base that is activated by Glu369. These data provide structural insights into the enzymatic methylation of these alkaloids that include a rare hydroxylamine oxygen acceptor, and can be used to guide future efforts towards selective derivatization and structural diversification and establishing the role of methylation in bioactivity.
Roquefortine/Oxaline biosynthesis pathway metabolites in Penicillium ser. Corymbifera: in planta production and implications for competitive fitness
J Chem Ecol 2005 Oct;31(10):2373-90.PMID:16195849DOI:10.1007/s10886-005-7107-y.
Three strains of each of the seven taxa comprising the Penicillium series Corymbifera were surveyed by direct injection mass spectrometry (MS) and liquid chromatography-MS for the production of terrestric acid and roquefortine/Oxaline biosynthesis pathway metabolites when cultured upon macerated tissue agars prepared from Allium cepa, Zingiber officinale, and Tulipa gesneriana, and on the defined medium Czapek yeast autolysate agar (CYA). A novel solid-phase extraction methodology was applied for the rapid purification of roquefortine metabolites from a complex matrix. Penicillium hordei and P. venetum produced roquefortine D and C, whereas P. hirsutum produced roquefortine D and C and glandicolines A and B. P. albocoremium, P. allii, and P. radicicola carried the pathway through to meleagrin, producing roquefortine D and C, glandicolines A and B, and meleagrin. P. tulipae produced all previously mentioned metabolites yet carried the pathway through to an end product recognized as epi-neoxaline, prompting the proposal of a roquefortine/epi-neoxaline biogenesis pathway. Terrestric acid production was stimulated by all Corymbifera strains on plant-derived media compared to CYA controls. In planta, production of terrestric acid, roquefortine C, glandicolines A and B, meleagrin, epi-neoxaline, and several other species-related secondary metabolites were confirmed from A. cepa bulbs infected with Corymbifera strains. The deposition of roquefortine/Oxaline pathway metabolites as an extracellular nitrogen reserve for uptake and metabolism into growing mycelia and the synergistic role of terrestric acid and other Corymbifera secondary metabolites in enhancing the competitive fitness of Corymbifera species in planta are proposed.
Indolyl alkaloid derivatives, Nb-acetyltryptamine and Oxaline from a marine-derived fungus
Arch Pharm Res 2003 Jan;26(1):21-3.PMID:12568352DOI:10.1007/BF03179925.
Indolyl alkaloids, Nb-acetyltryptamine (1) and the known Oxaline (2) have been isolated from the organic extract of the broth of an unidentified fungus collected from the surface of the marine red alga Gracilaria verrucosa. The structure of Nb-acetyltryptamine (1) was assigned on the basis of comprehensive spectroscopic analyses.