Isolongifolene
(Synonyms: 异长叶烯; (-)-Isolongifolene) 目录号 : GC60949
Isolongifolene((-)-Isolongifolene)是一种从Murrayakoenigii中分离的三环倍半萜烯。Isolongifolene通过调节P13K/AKT/GSK-3β信号通路来减轻鱼藤酮诱导的氧化应激，线粒体功能障碍和细胞凋亡。Isolongifolene具有抗氧化，抗炎，抗癌和神经保护的特性。
Cas No.:1135-66-6
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
Isolongifolene ((-)-Isolongifolene) is a tricyclic sesquiterpene isolated from Murraya koenigii. Isolongifolene attenuates Rotenone-induced oxidative stress, mitochondrial dysfunction and apoptosis through the regulation of P13K/AKT/GSK-3β signaling pathways. Isolongifolene has antioxidant, anti-inflammatory, anticancer and neuroprotective properties[1].
Isolongifolene (0-50 μM; 26 hours; SH-SY5Y neuroblastoma cells) treatment significantly alleviates Rotenone-induced cytotoxicity in SH-SY5Y cells in a dose-dependent manner[1].Isolongifolene (10 μM; 26 hours; SH-SY5Y neuroblastoma cells) treatment attenuates Rotenone-induced apoptosis in SH-SY5Y cells[1].Isolongifolene (10 μM; 26 hours; SH-SY5Y neuroblastoma cells) treatment attenuates Rotenone induced toxicity by down-regulating Bax, caspases-3, 6, 8 and 9 expression and up-regulating of Bcl-2 expression. Furthermore regulation of p-P13K, p-AKT and p-GSK-3β expression by Isolongifolene[1]. Cell Viability Assay[1] Cell Line: SH-SY5Y neuroblastoma cells
[1]. Balakrishnan R, et al. Isolongifolene attenuates rotenone-induced mitochondrial dysfunction, oxidative stress and apoptosis. Front Biosci (Schol Ed). 2018 Jan 1;10:248-261.
| Cas No. | 1135-66-6 | SDF | |
| 别名 | 异长叶烯; (-)-Isolongifolene | ||
| Canonical SMILES | CC1(C)[C@]23CC[C@](C3)([H])C(C)(C)C2=CCC1 | ||
| 分子式 | C15H24 | 分子量 | 204.35 |
| 溶解度 | DMSO: 10 mg/mL (48.94 mM); Water: < 0.1 mg/mL (insoluble) | 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 | 4.8936 mL | 24.4678 mL | 48.9356 mL |
| 5 mM | 0.9787 mL | 4.8936 mL | 9.7871 mL |
| 10 mM | 0.4894 mL | 2.4468 mL | 4.8936 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。
Isolongifolene alleviates liver ischemia/reperfusion injury by regulating AMPK-PGC1α signaling pathway-mediated inflammation, apoptosis, and oxidative stress
Int Immunopharmacol 2022 Dec;113(Pt A):109185.PMID:36252482DOI:10.1016/j.intimp.2022.109185.
Isolongifolene (ISO) has antioxidant, anti-inflammatory, anticancer, and neuroprotective effects; however, it is unclear whether ISO has a protective effects against liver ischemia/reperfusion (I/R) injury. In this study, a mouse liver I/R injury model and a mouse AML12 cell Hypoxia reoxygenation (H/R) model were established after pretreatment with different concentrations of ISO. Serum transaminase levels, necrotic liver area, cell viability, inflammation response, oxidative stress, and apoptosis were used to evaluate the effect of ISO on liver I/R or cell H/R injury. Western blotting was used to detect Bax, Bcl-2, C-Caspase3, AMPK, P-AMPK, and PGC1α protein expression levels. The AMPK inhibitor, compound C, was used to inhibit the AMPK expression. The results showed that ISO reduced serum alanine aminotransferase (ALT) and aspartate aminotransferase (AST) levels, liver necrosis, inflammatory factors IL-1β, IL-6, MCP-1, and TNF-α expression, MPO+ inflammatory cell infiltration, MDA content, TUNEL-positive cell number, cell apoptosis rate, and the expression of pro-apoptotic proteins Bax and C-Caspase3, while increasing cell viability, SOD and GSH activity, and the expression of anti-apoptotic protein Bcl-2. Moreover, Western blotting results showed that ISO could increase the protein expression of P-AMPK and PGC1α. Following the addition of compound C, the protective effect of ISO was significantly weakened. Therefore, our results suggest that ISO alleviates liver I/R injury by regulating AMPK-PGC1α signaling pathway-mediated anti-inflammatory, and antioxidant and anti-apoptotic effects.
Isolongifolene attenuates rotenone-induced mitochondrial dysfunction, oxidative stress and apoptosis
Front Biosci (Schol Ed) 2018 Jan 1;10(2):248-261.PMID:28930531DOI:10.2741/s513.
The present study was carried out to investigate the neuroprotective effects of Isolongifolene (ILF), a tricyclic sesquiterpene of Murraya koenigii, against rotenone-induced mitochondrial dysfunction, oxidative stress and apoptosis in a cellular model. SH-SY5Y human neuroblastoma cells were divided into four experimental groups (control, rotenone (100 nM), ILF (10 microM) + rotenone (100 nanoM), ILF 10 microM alone treated) based on 3-(4, 5-dimethyl 2-yl)-2, 5-diphenyltetrazolium bromide (MTT) assay. The results of the present study showed that the ILF treatment significantly alleviated rotenone-induced cytotoxicity, oxidative stress and mitochondrial dysfunction in SH-SY5Y cells. Moreover, ILF attenuated rotenone induced toxicity by down-regulating Bax, caspases-3, 6, 8 and 9 expression and up-regulating of Bcl-2 expression. Furthermore regulation of p-P13K, p-AKT and p-GSK-3 beta expression by ILF, clearly confirmed its protective effects. Taken together, our results suggested that ILF attenuated rotenone-induced oxidative stress, mitochondrial dysfunction and apoptosis through the regulation of P13K/AKT/GSK-3 beta signaling pathways. However further pre-clinical studies are warranted in rodents to use ILF as a promising therapeutic agent for PD in future.
Isolongifolene mitigates rotenone-induced dopamine depletion and motor deficits through anti-oxidative and anti-apoptotic effects in a rat model of Parkinson's disease
J Chem Neuroanat 2021 Mar;112:101890.PMID:33220427DOI:10.1016/j.jchemneu.2020.101890.
Isolongifolene (ILF), a novel tricyclic sesquiterpene compound isolated from the Indian herb Murraya koenigii (M. koenigii), has been previously demonstrated to have a neuroprotective effect against rotenone-induced oxidative stress, mitochondrial dysfunction, and apoptosis in in vitro model. However, these neuroprotective and anti-apoptotic effects of ILF are not well understood and must be further investigated to elucidate the underlying molecular mechanism of ILF in animal experiments. The objective of this study was to evaluate the neuroprotective effect of ILF on motor impediments, neurochemical variables, anti-oxidative indices, and apoptotic protein expression in a rotenone-induced rat model of Parkinson's disease (PD). PD was induced in male albino Wistar rats via injection of 2.5 mg/kg rotenone for 4 weeks. Rotenone produces PD-like effects by promoting mitochondrial complex I inhibition and microglial activation properties. The protective effect of three different doses of ILF 5, 10 and 20 mg/kg were evaluated for spontaneous locomotion, rotarod performance, and striatal dopamine (DA) content. The results showed that ILF dose-dependently ameliorated the rotenone-induced striatal DA loss and motor impairment from 10 mg/kg. Therefore, we selected 10 mg/kg as the ILF dose for further investigation. Chronic administration of rotenone caused PD-related pathological processes like oxidative stress, and produced a significant decrease in tyrosine hydroxylase (TH), DA transporter (DAT), Vesicular monoamine transporter 2 (VMAT2), and a significant upregulated in α-synuclein and apoptotic protein expression of Bax, Cyt-C and caspases -3, -8 and -9 as well as by decreasing Bcl2 expression. Treatment with ILF 10 mg/kg mitigated oxidative stress in rotenone-treated rats. Furthermore, ILF dramatically alleviated rotenone-induced toxicity and cell death by increasing TH, DAT and VMAT2 expression and reducing the upregulation of α-synuclein, Bax, Cyt-C, caspases -3, -8 and -9. Together, our results confirm that ILF's protective effect against rotenone-induced PD is mediated through anti-oxidant and anti-apoptotic properties. However, further in-depth investigations on ILF's anti-inflammatory and mitochondrial protective abilities are needed to establish ILF as a potential drug candidate for the treatment of Parkinson's disease.
Sesquiterpene Cyclisations Catalysed inside the Resorcinarene Capsule and Application in the Short Synthesis of Isolongifolene and Isolongifolenone
Nat Catal 2018 Aug;1(8):609-615.PMID:30221250DOI:10.1038/s41929-018-0115-4.
Terpenes constitute the largest class of natural products and serve as an important source for medicinal treatments. Despite constant progress in chemical synthesis, the construction of complex polycyclic sesqui- and diterpene scaffolds remains challenging. Natural cyclase enzymes, however, are able to form the whole variety of terpene structures from just a handful of linear precursors. Man-made catalysts able to mimic such natural enzymes are lacking. Here, we describe the examples of sesquiterpene cyclisations inside an enzyme-mimicking supramolecular catalyst. This strategy allowed the formation of the tricyclic sesquiterpene Isolongifolene in only four steps. The mechanism of the catalysed cyclisation reaction was elucidated using 13C-labelling studies and DFT calculations.
Nutraceutical potential, and antioxidant and antibacterial properties of Quararibea funebris flowers
Food Chem 2023 Jun 15;411:135529.PMID:36689869DOI:10.1016/j.foodchem.2023.135529.
The flowers of Quararibea funebris tree are an important component of tejate, a traditional Mexican beverage. The flowers exhibited a high concentration of total polyphenolic compounds, total carotenoids, and vitamin C. UPLC analysis revealed the presence of salicylic acid, kaemferol-3-O-glucoside, trans-cinnamic acid, rutin, scopoletin, l-phenylalanine, 4-coumaric acid and quercetin-3-glucoside, among others metabolites. The flowers exhibited volatile compounds as Isolongifolene, α-cedrene, 2,5,5-trimethyl-2,3,4,5,6,7-hexahydro-1H-2,4a-ethanonaphthalene, while that linoleic acid, palmitic acid, and linolenic acid were the major fatty acids present in the oil extract. Magnesium, potassium, and calcium were the minerals most abundant in the flowers. In addition the methanolic extract of the flowers exhibited antimicrobial properties against the tested pathogenic microbial strains. In conclusion, these results showed that the Q. funebris flowers not only have an aromatic and flavoring power for the Tejate beverage, but also contains compounds with antioxidant, antimicrobial, and nutraceutical potential, which helps to explain its therapeutic uses.