Nimbin
(Synonyms: 宁宾) 目录号 : GC46185
A limonoid with diverse biological activities
Cas No.:5945-86-8
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
Nimbin is a limonoid that has been found in neem seeds and has diverse biological activities.1,2,3 It inhibits the growth of the plant pathogenic fungus D. oryzae by 64.8% when used at a concentration of 1,000 ppm.1 Nimbin (0.02-2,000 μM) has antifeedant activity against S. littoralis in a choice test.2 It decreases melanin content to 20.9% of control, without affecting viability, in B16 murine melanoma cells when used at a concentration of 25 μg/ml.3 Nimbin inhibits activation of Epstein-Barr virus early antigen (EBV-EA) induced by phorbol 12-myristate 13-acetate in Raji cells (IC50 = 499 mol ratio/32 pmol TPA).
|3. Akihisa, T., Noto, T., Takahashi, A., et al. Melanogenesis inhibitory, anti-inflammatory, and chemopreventive effects of limonoids from the seeds of Azadirachta indicia A. juss. (neem). J. Oleo. Sci. 58(11), 581-594 (2009).
| Cas No. | 5945-86-8 | SDF | |
| 别名 | 宁宾 | ||
| Canonical SMILES | CC1=C2[C@@]3(C)[C@H](CC(OC)=O)[C@@]4(C)C(C=C[C@](C(OC)=O)(C)[C@]4([H])[C@@H](OC(C)=O)[C@@]3([H])O[C@]2([H])C[C@@]1([H])C5=COC=C5)=O | ||
| 分子式 | C30H36O9 | 分子量 | 540.6 |
| 溶解度 | Chloroform: slightly soluble,Ethyl Acetate: slightly 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 | 1.8498 mL | 9.249 mL | 18.498 mL |
| 5 mM | 0.37 mL | 1.8498 mL | 3.6996 mL |
| 10 mM | 0.185 mL | 0.9249 mL | 1.8498 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。
Deacetylated Nimbin analog N2 fortifies alloxan-induced pancreatic β-cell damage in insulin-resistant zebrafish larvae by upregulating phosphoenolpyruvate carboxykinase (PEPCK) and insulin levels
Toxicol Appl Pharmacol 2022 Nov 1;454:116229.PMID:36089001DOI:10.1016/j.taap.2022.116229.
This study aims to evaluate the protective behaviour of N2, a semi-natural analog of Nimbin, for its anti-diabetic efficacy against alloxan-induced oxidative damage and β-cell dysfunction in in-vivo zebrafish larvae. A 500 μM of alloxan was exposed to zebrafish larvae for 24 h to induce oxidative stress in the pancreatic β-cells and co-exposed with N2 to study the protection of N2 by inhibiting ROS by DCFH-DA, DHE and NDA staining along with Cellular damage, apoptosis and lipid peroxidation. The zebrafish was further exposed to 500 μM alloxan for 72 h to induce β-cell destruction along with depleted glucose uptake and co-exposed to N2 to study the protective mechanism. Glucose levels were estimated, and PCR was used to verify the mRNA expression of phosphoenolpyruvate carboxykinase (PEPCK) and insulin. Alloxan induced (24 h) oxidative stress in the pancreatic β-cells in which N2's co-exposure inhibited ROS by eliminating O-₂ radicals and restoring the glutathione levels, thus preventing cellular damage and lipid peroxidation. The zebrafish exposed to 500 μM alloxan for 72 h was observed with β-cell destruction along with depleted glucose uptake when stained with 2NBDG, wherein N2 was able to protect the pancreatic β-cells from oxidative damage, promoted high glucose uptake and reduced glucose levels. N2 stimulated insulin production and downregulated PEPCK by inhibiting gluconeogenesis, attenuating post-prandial hyperglycemia. N2 may contribute to anti-oxidant protection against alloxan-induced β-cell damage and anti-hyperglycemic activity, restoring insulin function and suppressing PEPCK expression.
Multilayer capsules encapsulating Nimbin and doxorubicin for cancer chemo-photothermal therapy
Int J Pharm 2020 May 30;582:119350.PMID:32315747DOI:10.1016/j.ijpharm.2020.119350.
Layer-by-layer (LbL) assembled poly(allylamine hydrochloride) (PAH) and poly(methacrylic acid) (PMA) microcapsules were designed to incorporate gold nanorods (NRs) and co-encapsulate and release two drugs for cancer therapy. Calcium carbonate (CaCO3) microparticles modified with preformed NRs were used as sacrificial templates for the fabrication of hollow PAH/PMA/NR capsules incorporated with NRs. The hollow capsules were found to be 4.5 ± 0.5 µm in size and appeared with uniformly distributed NRs in the interior of the capsules. The morphology of the capsules transformed from pore free continuous structure to porous structure under laser light irradiation at 808 nm and 0.5 W cm-2. The encapsulation experiments showed that the hydrophilic drug (doxorubicin hydrochloride, Dox) was encapsulated in the interior of the capsules while the hydrophobic drug (Nimbin, NB) was entrapped in the porous polymeric network of the layer components. The encapsulation efficiency was found to be 30% for both Dox and NB. The release experiments showed an initial burst release followed by sustained release up to 3 h. Notably, the release was completed within 30 min under NIR irradiation at 808 nm. The estimated IC50 values against THP-1 cells were 75 and 1.8 µM for NB and Dox, respectively. The dual drug loaded capsules showed excellent anticancer activity against THP-1 cells under NIR light exposure in in-vitro experiments. Thus, such remotely addressable dual-drug loaded capsules with the provision for encapsulation of natural drugs demonstrate high potential for use as theranostics in cancer therapy.
Reverse pharmacology of Nimbin-N2 attenuates alcoholic liver injury and promotes the hepatoprotective dual role of improving lipid metabolism and downregulating the levels of inflammatory cytokines in zebrafish larval model
Mol Cell Biochem 2022 Oct;477(10):2387-2401.PMID:35575874DOI:10.1007/s11010-022-04448-7.
Alcoholic liver disease is one of the most prominent liver diseases in the world. Lipid accumulation accompanied by oxidative stress and inflammation in the liver is the most important pathogenesis of ALD. This study was designed to investigate the anti-oxidative, fat metabolism-regulating, and anti-inflammatory potential of N2, a seminatural analog of Nimbin. The ethanol exposure was found to induce liver injury on zebrafish larvae, such as liver inflammation, lipid accumulation, oxidative stress, and hepatocytes apoptosis. N2 was subjected to ADMET screening in-silico, and it was observed N2's co-exposure decreased the ROS, apoptosis, lipid peroxidation, and macrophage accumulation in the liver of larval zebrafish. To further study the mechanism behind ethanol hepatotoxicity and the hepatoprotective behavior of N2, gene expression changes were determined in zebrafish. The results of this study revealed that ethanol exposure upregulated mRNA expressions of SREBP1, C/EBP-α, FAS and provoked more severe oxidative stress and hepatitis via upregulation of inflammatory cytokines TNF-α, IL-10, IL-1β, iNOS, COX-2. However, the N2 co-exposure protected the hepatocyte damage and almost reversed the condition by downregulating the mRNA levels. The study suggested that N2 could be an effective therapeutic agent for the treatment of ALD and other inflammatory conditions.
Nimbin analogs N5 and N7 regulate the expression of lipid metabolic genes and inhibit lipid accumulation in high-fat diet-induced zebrafish larvae: An antihyperlipidemic study
Tissue Cell 2023 Feb;80:102000.PMID:36542946DOI:10.1016/j.tice.2022.102000.
Background: Excess accumulation of lipids leads to obesity. Triterpenoids are a group of plant compounds which poses various biological activities. The biological activities of Nimbin analogs N5 and N7 were addressed in this study on inhibiting lipid aggregation and underlying the derivatives molecular mechanisms for a therapeutical approach. Aim: This study aims to evaluate the anti-adipogenic activity of semi-natural Nimbin analogs, N5 and N7, on zebrafish larvae induced with oxidative stress due to a high-fat diet (HFD) and adipogenesis using specific fluorescent stains. Materials and methods: Zebrafish at 4 days post fertilized (dpf) larvae were divided into groups for the HFD diet along with exposure to various concentrations of N5 and N7. HFD induced accumulation of neutral lipids and triglycerides (Oil Red O and Nile red staining, respectively) with weight gain, which generated intracellular ROS (DCFH-DA staining) and superoxide anion production (DHE staining) with depleted glutathione levels (NDA staining) were assayed. HFD exposure promoted the accumulation of inflammatory macrophages (Neutral red staining) and impaired glucose metabolism (2NBDG staining). The ability of N5 and N7 to reduce total regulating lipogenic specific genes C/EBP-α, SREBP-1 and FAS were evaluated using relative gene expression. Key findings: The Nimbin analogues N5 and N7 suppressed adipogenesis, forming intracellular ROS and superoxide anion while simultaneously restoring glutathione levels. The analogues significantly lowered total TC and TG levels, prevented inflammatory macrophage build-up and boosted glucose absorption. Also, N5 and N7 down-regulate the lipogenic-specific genes. Significance: Nimbin analogs N5 and N7 enhance lipolysis and inhibit adipogenesis in in-vivo zebrafish larvae model.
Nimbin analog N2 alleviates high testosterone induced oxidative stress in CHO cells and alters the expression of Tox3 and Dennd1a signal transduction pathway involved in the PCOS zebrafish
Phytother Res 2023 Apr;37(4):1449-1461.PMID:36450691DOI:10.1002/ptr.7685.
Polycystic ovarian syndrome (PCOS) is a hormonal disorder that causes enlargement of ovaries and follicular maturation arrest, which lacks efficient treatment. N2, a semi-natural triterpenoid from the neem family, was already reported to have antioxidant and antiinflammatory properties in our previous report. This study investigated the anti-androgenic property of N2 on testosterone-induced oxidative stress in Chinese Hamster Ovarian cells (CHO) and PCOS zebrafish model. The testosterone exposure disrupted the antioxidant enzymes and ROS level and enhanced the apoptosis in both CHO cells and PCOS zebrafish. However, N2 significantly protected the CHO cells from ROS and apoptosis. N2 improved the Gonado somatic index (GSI) and upregulated the expression of the SOD enzyme in zebrafish ovaries. Moreover, the testosterone-induced follicular maturation arrest was normalized by N2 treatment in histopathology studies. In addition, the gene expression studies of Tox3 and Denndla in zebrafish demonstrated that N2 could impair PCOS condition. Furthermore, to confirm the N2 activity, the in-silico studies were performed against PCOS susceptible genes Tox3 and Dennd1a using molecular docking and molecular dynamic simulations. The results suggested that N2 alleviated the oxidative stress and apoptosis in-vitro and in-vivo and altered the expression of PCOS key genes.