Nidulin
(Synonyms: 巢曲菌素) 目录号 : GC44402
A depsidone
Cas No.:10089-10-8
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >99.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Nidulin is a depsidone originally isolated from A. nidulans. It is active against the bacteria M. tuberculosis and M. ranoe, as well as the fungi T. tonsurans and M. audouini. It also inhibits the growth of methicillin-resistant S. aureus (MRSA; MIC = 4 µg/ml) and has larvicidal activity toward Artemia (LC50 = 2.8 µg/ml). Nidulin is cytotoxic to MOLT-3 cells (IC50 = 21.2 µM) but not HuCCA-1, HepG2, or A549 cells (IC50s = >112.7 µM). It inhibits aromatase with an IC50 value of 11.2 µM.
| Cas No. | 10089-10-8 | SDF | |
| 别名 | 巢曲菌素 | ||
| Canonical SMILES | O=C(OC(C(C)=C(OC)C(Cl)=C1/C(C)=C/C)=C1O2)C3=C2C(Cl)=C(O)C(Cl)=C3C | ||
| 分子式 | C20H17Cl3O5 | 分子量 | 443.7 |
| 溶解度 | DMF: 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 | 2.2538 mL | 11.2689 mL | 22.5378 mL |
| 5 mM | 0.4508 mL | 2.2538 mL | 4.5076 mL |
| 10 mM | 0.2254 mL | 1.1269 mL | 2.2538 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。
Semisynthesis and antibacterial activities of Nidulin derivatives
J Antibiot (Tokyo) 2019 Mar;72(3):181-184.PMID:30555155DOI:10.1038/s41429-018-0133-0.
Derivatives of the fungal depsidone, Nidulin, have been synthesized in order to evaluate the potential of the chemical skeleton as antibacterial agents. Alkylation, acylation, and arylation reactions of nornidulin underwent in a regioselective manner to predominantly produce 8-O-substituted derivatives. Many of the semisynthetic derivatives showed more potent antibacterial activities than Nidulin, In particular, 8-O-aryl ether derivatives displayed significant activities against Gram-positive bacteria, including Methicillin-resistant Staphylococcus aureus.
Expanding antibiotic chemical space around the Nidulin pharmacophore
Org Biomol Chem 2018 Apr 25;16(16):3038-3051.PMID:29634062DOI:10.1039/c8ob00545a.
Reinvestigating antibiotic scaffolds that were identified during the Golden Age of antibiotic discovery, but have long since been "forgotten", has proven to be an effective strategy for delivering next-generation antibiotics capable of combatting multidrug-resistant superbugs. In this study, we have revisited the trichloro-substituted depsidone, Nidulin, as a selective and unexploited antibiotic lead produced by the fungus Aspergillus unguis. Manipulation of halide ion concentration proved to be a powerful tool for modulating secondary metabolite production and triggering quiescent pathways in A. unguis. Supplementation of the culture media with chloride resulted in a shift in co-metabolite profile to dichlorounguinols and nornidulin at the expense of the non-chlorinated parent, unguinol. Surprisingly, only marginal enhancement of Nidulin was observed, suggesting O-methylation may be rate-limiting. Similarly, supplementation of the media with bromide led to the production of the corresponding bromo-analogues, but also resulted in a novel family of depsides, the unguidepsides. Unexpectedly, depletion of chloride from the media halted the biosynthesis of the non-chlorinated parent compound, unguinol, and redirected biosynthesis to a novel family of ring-opened analogues, the unguinolic acids. Supplementation of the media with a range of unnatural salicylic acids failed to yield the corresponding Nidulin analogues, suggesting the compounds may be biosynthesised by a single polyketide synthase. In total, 12 new and 11 previously reported Nidulin analogues were isolated, characterised and assayed for in vitro activity against a panel of bacteria, fungi and mammalian cells, providing a comprehensive structure-activity profile for the Nidulin scaffold.
(E)-2,4,7-Trichloro-3-hydr-oxy-8-meth-oxy-1,9-dimethyl-6-(1-methyl-1-propen-yl)-11H-dibenzo[b,e][1,4]dioxepin-11-one monohydrate (Nidulin monohydrate)
Acta Crystallogr Sect E Struct Rep Online 2009 Sep 16;65(Pt 10):o2470-1.PMID:21577923DOI:10.1107/S1600536809036277.
In the title compound, C(20)H(17)Cl(3)O(5)·H(2)O, the Nidulin mol-ecule consists of three rings, the folded central dioxepin-11-one ring being fused on both sides to phenyl rings. The mol-ecular structure is stabilized by intra-molecular O-H⋯Cl and C-H⋯Cl hydrogen bonds that generate S(6) ring motifs. The crystal structure is stabilized by inter-molecular O-H⋯O and O-H⋯(O,O) hydrogen bonds mediated by two inversion-related water mol-ecules, generating R(4) (2)(8) ring and C(2) (2)(4) chain motifs. Weak inter-molecular Cl⋯O halogen bonds are also present with Cl⋯O distances of 3.071 (1) and 3.182 (2) Å.
Secondary Metabolites Diversity of Aspergillus unguis and Their Bioactivities: A Potential Target to Be Explored
Biomolecules 2022 Dec 6;12(12):1820.PMID:36551248DOI:10.3390/biom12121820.
Aspergillus unguis belongs to the Aspergillus section Nidulantes. This species is found in soils and organisms from marine environments, such as jellyfishes and sponges. The first chemical study reported in the literature dates from 1970, with depsidones Nidulin (1), nornidulin (2), and unguinol (3) being the first isolated compounds. Fifty-two years since this first study, the isolation and characterization of ninety-seven (97) compounds have been reported. These compounds are from different classes, such as depsides, depsidones, phthalides, cyclopeptides, indanones, diarylethers, pyrones, benzoic acid derivatives, orcinol/orsenillate derivatives, and sesterpenoids. In terms of biological activities, the first studies on isolated compounds from A. unguis came only in the 1990s. Considering the tendency for antiparasitic and antibiotics to become ineffective against resistant microorganisms and larvae, A. unguis compounds have also been extensively investigated and some compounds are considered very promising. In addition to these larvicidal and antimicrobial activities, these compounds also show activity against cancer cell lines, animal growth promotion, antimalarial and antioxidant activities. Despite the diversity of these compounds and reported biological activities, A. unguis remains an interesting target for studies on metabolic induction to produce new compounds, the determination of new biological activities, medicinal chemistry, structural modification, biotechnological approaches, and molecular modeling, which have yet to be extensively explored.
Depsidones, aromatase inhibitors and radical scavenging agents from the marine-derived fungus Aspergillus unguis CRI282-03
Planta Med 2012 Apr;78(6):582-8.PMID:22307935DOI:10.1055/s-0031-1298228.
Three new depsidones ( 1, 3, and 4), a new diaryl ether ( 5), and a new natural pyrone ( 9) (synthetically known), together with three known depsidones, Nidulin ( 6), nornidulin ( 7), and 2-chlorounguinol ( 8), were isolated from the marine-derived fungus ASPERGILLUS UNGUIS CRI282-03. Aspergillusidone C ( 4) showed the most potent aromatase inhibitory activity with the IC (50) value of 0.74 µM, while depsidones 1, 3, 6- 8 inhibited aromatase with IC (50) values of 1.2-11.2 µM. It was found that the structural feature of depsidones, not their corresponding diaryl ether derivatives (e.g. 5), was important for aromatase inhibitory activity. Aspergillusidones A ( 1) and B ( 3) showed radical scavenging activity in the XXO assay with IC (50) values of 16.0 and < 15.6 µM, respectively. Compounds 1 and 3- 7 were mostly inactive or showed only weak cytotoxic activity against HuCCA-1, HepG2, A549, and MOLT-3 cancer cell lines.