Sclerotiorin
(Synonyms: 核丛青霉素) 目录号 : GC44879
A natural compound with LOX and CETP inhibitory activity
Cas No.:549-23-5
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Sclerotiorin is a natural product isolated primarily from Penicillium species. It inhibits soybean lipoxygenase-1 with an IC50 value of 4.2 µM. Sclerotiorin also exhibits a number of other activities including inhibition of cholesterol ester transfer protein (IC50 = 19.4 µM),, inhibition of Grb2-Shc interaction (IC50 = 22 µM),, and antagonism of endothelin receptors (IC50 = 114 and 152 µM for human ETA and ETB, respectively).
| Cas No. | 549-23-5 | SDF | |
| 别名 | 核丛青霉素 | ||
| Canonical SMILES | O=C1C2=COC(/C=C/C(C)=C/[C@@H](C)CC)=CC2=C(Cl)C([C@]1(C)OC(C)=O)=O | ||
| 分子式 | C21H23ClO5 | 分子量 | 390.9 |
| 溶解度 | DMF: 30 mg/ml,DMF:PBS(pH7.2) (1:2): 0.3 mg/ml,DMSO: 20 mg/ml,Ethanol: 3 mg/ml | 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 | 2.5582 mL | 12.791 mL | 25.582 mL |
| 5 mM | 0.5116 mL | 2.5582 mL | 5.1164 mL |
| 10 mM | 0.2558 mL | 1.2791 mL | 2.5582 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。
Sclerotiorin inhibits protein kinase G from Mycobacterium tuberculosis and impairs mycobacterial growth in macrophages
Tuberculosis (Edinb) 2017 Mar;103:37-43.PMID:28237032DOI:10.1016/j.tube.2017.01.001.
As a eukaryotic-like Ser/Thr protein kinase, Mycobacterium tuberculosis virulent effector protein kinase G (PknG) mediates mycobacterial survival by regulating bacterial cell metabolic processes and preventing phagosome-lysosome fusion in host macrophages. Targeting PknG is an effective strategy for development of anti-tuberculosis (TB) drugs. In the study, we found that Sclerotiorin, derived from marine fungi from the South China Sea, exhibited moderately strong inhibitory effects on recombinant PknG, with an IC50 value of 76.5 μM, and acted as a non-competitive inhibitor. The dissociation constant (KD) of Sclerotiorin determined by MST was 11.4 μM, demonstrating a moderate binding strength between them. Sclerotiorin could substantially impair the mycobacterial survival in infected macrophages while the macrophage viability remained unaffected, though it did not inhibit the mycobacterial growth in culture. When Sclerotiorin was used in combination with rifampicin, intracellular mycobacterial growth decreased as Sclerotiorin concentration increased. Docking analysis suggested a binding mechanism of inhibition with performing interactions with the P-loop and catalytic loop of PknG. In summary, we reported that Sclerotiorin had moderately strong PknG inhibitory activity, but no cytotoxicity, and it could substantially decrease the mycobacterial growth inside macrophages, suggesting that Sclerotiorin has potential to supplement antibiotic therapy for TB.
Preparation, COX-2 Inhibition and Anticancer Activity of Sclerotiorin Derivatives
Mar Drugs 2020 Dec 29;19(1):12.PMID:33383842DOI:10.3390/md19010012.
The latest research has indicated that anti-tumor agents with COX-2 inhibitory activity may benefit their anti-tumor efficiency. A series of Sclerotiorin derivatives have been synthesized and screened for their cytotoxic activity against human lung cancer cells A549, breast cancer cells MDA-MB-435 using the MTT method. Among them, compounds 3, 7, 12, 13, 15, 17 showed good cytotoxic activity with IC50 values of 6.39, 9.20, 9.76, 7.75, 9.08, and 8.18 μM, respectively. In addition, all compounds were tested in vitro the COX-2 inhibitory activity. The results disclosed compounds 7, 13, 25 and Sclerotiorin showed moderate to good COX-2 inhibition with the inhibitory ratios of 58.7%, 51.1%, 66.1% and 56.1%, respectively. Notably, compound 3 displayed a comparable inhibition ratio (70.6%) to the positive control indomethacin (78.9%). Furthermore, molecular docking was used to rationalize the potential of the Sclerotiorin derivatives as COX2 inhibitory agents by predicting their binding energy, binding modes and optimal orientation at the active site of the COX-2. Additionally, the structure-activity relationships (SARS) have been addressed.
Sequential fungal fermentation-biotransformation process to produce a red pigment from Sclerotiorin
Food Chem 2016 Nov 1;210:355-61.PMID:27211658DOI:10.1016/j.foodchem.2016.04.057.
The fungus Penicillium sclerotiorum produces Sclerotiorin, an orange compound closely related to the useful food coloring pigments produced by Monascus species. The high productivity, together with several biological activities reported for Sclerotiorin highlights its potential application in food industry. In this work, Sclerotiorin was obtained as the major metabolite produced in liquid fermentation by P. sclerotiorum standing for 30% of the fungal dry extract. Modulation of Sclerotiorin color was accomplished by biotransformation using Beauveria bassiana generating a red derivative with 13.8% yield. Color modification was caused by fungal-mediated substitution of oxygen by nitrogen in the pyrone ring changing the molecule's chromophore. A derivative, 1-methyl Sclerotiorin was synthesized from Sclerotiorin using diazomethane and fed to B. bassiana. In this case, substituent at C-1 avoided heteroatom substitution. Sclerotiorin derivatives obtained in the present show the great potential of Sclerotiorin derivatives as food colorants.
Sclerotiorin Stabilizes the Assembly of Nonfibrillar Abeta42 Oligomers with Low Toxicity, Seeding Activity, and Beta-sheet Content
J Mol Biol 2020 Mar 27;432(7):2080-2098.PMID:32061932DOI:10.1016/j.jmb.2020.01.033.
The self-assembly of the 42-residue amyloid-β peptide, Aβ42, into fibrillar aggregates is associated with neuronal dysfunction and toxicity in Alzheimer's disease (AD) patient brains, suggesting that small molecules acting on this process might interfere with pathogenesis. Here, we present experimental evidence that the small molecule Sclerotiorin (SCL), a natural product belonging to the group of azaphilones, potently delays both seeded and nonseeded Aβ42 polymerization in cell-free assays. Mechanistic biochemical studies revealed that the inhibitory effect of SCL on fibrillogenesis is caused by its ability to kinetically stabilize small Aβ42 oligomers. These structures exhibit low β-sheet content and do not possess seeding activity, indicating that SCL acts very early in the amyloid formation cascade before the assembly of seeding-competent, β-sheet-rich fibrillar aggregates. Investigations with NMR WaterLOGSY experiments confirmed the association of Aβ42 assemblies with SCL in solution. Furthermore, using ion mobility-mass spectrometry, we observed that SCL directly interacts with a small fraction of Aβ42 monomers in the gas phase. In comparison to typical amyloid fibrils, small SCL-stabilized Aβ42 assemblies are inefficiently taken up into mammalian cells and have low toxicity in cell-based assays. Overall, these mechanistic studies support a pathological role of stable, β-sheet-rich Aβ42 fibrils in AD, while structures with low β-sheet content may be less relevant.
New azaphilones from mangrove endophytic fungus Penicillium Sclerotiorin SCNU-F0040
Nat Prod Res 2023 Jan;37(2):296-304.PMID:34498957DOI:10.1080/14786419.2021.1959580.
Two new sclerotioramines (1 and 2) and a new natural product of sclerotioramine analog (3), together with seven known compounds have been isolated from the mangrove endophytic fungus Penicillium Sclerotiorin SCNU-F0040. Their structures were identified based on the 1 D, 2 D NMR and HRESIM spectra. The absolute configurations of new compounds were deduced by specific rotation data and electronic circular dichroism spectra. All the isolated new compounds were tested on anti-diabetes activity by using a-glucosidase inhibition assay and anti-inflammatory activity by using cyclooxygenase inhibition assay, respectively. Compounds 1 and 2 have a-glucosidase inhibition activity with IC50 values of 102.3 and 217.5 μM. Compound 2 shows a moderate cyclooxygenase-2 inhibitory activity with an IC50 value of 47.8 μM.