Isoeleutherin
(Synonyms: 异红葱乙素) 目录号 : GC60944
Isoeleutherin是从Merr.EtHeyne中分离得到的萘酚类衍生物，具有抗真菌、抗病毒和抗肿瘤活性。Isoeleutherin在T辅助细胞介导的免疫反应选择性调节中起重要作用。
Cas No.:1078723-14-4
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
Isoeleutherin is a naphthopyran derivative isolated from E. americana Merr. Et Heyne with anti-fungal, anti-viral, and anti-tumor activities. Isoeleutherin plays an important role in selective modulation of T helper cell-mediated immune responses[1].
[1]. Francesca R Gallo, et al. Polyketides from Eleutherine bulbosa. Nat Prod Res. 2010 Oct;24(16):1578-86.
| Cas No. | 1078723-14-4 | SDF | |
| 别名 | 异红葱乙素 | ||
| Canonical SMILES | O=C(C1=C2[C@H](C)O[C@@H](C)C1)C3=C(C2=O)C(OC)=CC=C3 | ||
| 分子式 | C16H16O4 | 分子量 | 272.3 |
| 溶解度 | DMSO : 10 mg/mL (36.72 mM; Need ultrasonic) | 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 | 3.6724 mL | 18.3621 mL | 36.7242 mL |
| 5 mM | 0.7345 mL | 3.6724 mL | 7.3448 mL |
| 10 mM | 0.3672 mL | 1.8362 mL | 3.6724 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。
Isoeleutherin and eleutherinol, naturally occurring selective modulators of Th cell-mediated immune responses
Biochem Biophys Res Commun 2008 Jun 27;371(2):278-82.PMID:18435915DOI:10.1016/j.bbrc.2008.04.060.
Natural compounds possessing naphthopyran moiety have been attracted by their anti-bacterial, anti-fungal, and anti-viral activities, as well as anti-tumor activities. Although chemical structures were critical for the potential biological activities, the detailed functional mechanisms remained unclear. Here, we have studied the effects of naphthopyran derivatives (eleutherin, Isoeleutherin, and eleutherinol) on T helper cell-mediated immune responses to understand the mechanisms of their anti-microbial and anti-tumor activities. The study revealed that Isoeleutherin, which has 1,4-naphthoquinone ring with alpha-methyl group, selectively and specifically stimulated IFNgamma production through the activation of T-bet gene transcription, thus enhancing Th1-mediated immune responses. However, a natural naphthopyran-4-one, eleutherinol dramatically inhibited both IFNgamma and IL-2 productions during Th cell activation by suppressing the gene transcriptions of cytokines. Therefore, we suggest that the chemical modification and chirality of naphthopyran moiety in Isoeleutherin and eleutherinol may be critical for the selective modulation of T helper cell-mediated immune responses.
Study of Genotoxicity, Activities on Caspase 8 and on the Stabilization of the Topoisomerase Complex of Isoeleutherin and Analogues
Molecules 2023 Feb 8;28(4):1630.PMID:36838618DOI:10.3390/molecules28041630.
This study evaluated the genotoxicity of Ethanol Extract (EEEp), Dichloromethane Fraction (FDCMEp) and Isoeleutherin isolated from Eleutherine plicata, using the micronucleus test and the impact of structural alterations on toxicity and molecular docking (topoisomerase II and DNA complex). The extract was obtained by maceration and fractionation in a chromatography column. The genotoxicity was evaluated by the micronucleus test in human hepatoma cells (HepG2). Isoeleutherin was the starting molecule in the search for analogues by structural similarity, using the ZINC and e-Molecules databases. Isoeleutherin and analogues were subjected to in silico toxicity prediction, and compounds free of toxicological risks (CP13, CP14, CP17 and Isoeleutherin) were selected for molecular docking in Topoisomerase II (PDB: 1ZXM). In the micronucleus test, Isoeleutherin was less genotoxic. Among the 22 Isoeleutherin analogues there were variations in the toxicity profile. Molecular docking studies showed that the compounds have good complementarity in the active site with important hydrogens bonds. Therefore, the structural changes of Isoeleutherin led to the obtaining of a molecule with a lower mutagenic potential, and the CP13 can be considered a prototype compound for the development of new molecules with pharmacological potential.
Toxicity evaluation of Eleutherine plicata Herb. extracts and possible cell death mechanism
Toxicol Rep 2021 Jul 31;8:1480-1487.PMID:34401358DOI:10.1016/j.toxrep.2021.07.015.
Eleutherine plicata has been shown to be a promising medicinal plant, and its activity has been associated with naphthoquinones. The present study aimed at evaluating the cytotoxicity, genotoxicity, and oral toxicity of the ethanol extract (EEEp), dichloromethane fraction (FDMEp) of E. plicata, and Isoeleutherin. For the cytotoxicity evaluation, the viability test (MTT) was used. Genotoxicity was accessed through the Comet assay (alkaline version), acute and subacute oral toxicities were also evaluated. The antioxidant capacity of the samples in the wells where the cells were treated with E. plicata was evaluated. Furthermore, the participation of caspase-8 in the possible mechanism of action of Isoeleutherin, eleutherin, and eleutherol was also investigated through a docking study. FDMEp and Isoeleutherin were cytotoxic, with higher rates of DNA fragmentation observed for FDMEp and Isoeleutherin, and all samples displayed higher antioxidant potential than the control. In the acute oral toxicity test, EEEp, FDMEp, and Isoeleutherin did not cause significant clinical changes. In the subacute toxicity assay, EEEp and FDMEp also did not cause clinical, hematological, or biochemical changes. The three compounds bound similarly to caspase-8. Despite the results of cytotoxicity, in vitro studies demonstrated that the use of EEEp appears to be safe and cell death may involve its binding to caspase-8.
Polyketides from Eleutherine bulbosa
Nat Prod Res 2010 Oct;24(16):1578-86.PMID:20835959DOI:10.1080/14786419.2010.500007.
Four new polyketides, (R)-4-hydroxyeleutherin, eleuthone, eleutherinol-8-O-β-D-glucoside and isoeleuthoside C (dihydroisoeleutherin-5-O-β-D-gentiobioside) were isolated from the bulbs of Eleutherine bulbosa, to join eleutherin, Isoeleutherin, eleutherinol, eleutherol, eleuthoside B (eleutherol-4-O-β-D-gentiobioside), eleuthoside C (dihydroeleutherin-5-O-β-D-gentiobioside), hongconin (4-oxodihydroisoeleutherin) and elecanacin, which have already been isolated from the same plant. The structures of the new polyketides, based on oxydated cyclic systems, have been elucidated by chemical and spectroscopic methods.
Analysis of naphthoquinone derivatives in the Asian medicinal plant Eleutherine americana by RP-HPLC and LC-MS
J Pharm Biomed Anal 2008 Aug 5;47(4-5):990-3.PMID:18486396DOI:10.1016/j.jpba.2008.04.005.
The first analytical procedure for the determination of a new naphthopyrone, eleutherinoside A, together with the known bioactive compounds eleuthoside B, Isoeleutherin, eleutherin and eleutherol in Eleutherine americana was established. Optimum HPLC separation of these naphthoquinone derivatives was possible on RP-12 column material, using water and acetonitrile as mobile phase. Flow-rate, detection wavelength and temperature were adjusted to 1.0 mL/min, 254 nm and 40 degrees C, respectively. Validation results indicated that the HPLC method is well suited for the determination of naphthoquinone derivatives in the bulbs of E. americana with a good linearity (r2>0.9996), precision (intra-day R.S.D. <4.70%, inter-day R.S.D. <5.68%) and recovery rates from 96.26 to 103.48%. Limit of detection (LOD) was found to be below 0.84 microg/mL for all five compounds. LC-MS analyses performed in positive and negative electrospray ionization mode assured peak purity and identity. The analysis of different E. americana samples from Thailand revealed that eleutherol (0.10-0.20%) was dominant in all specimens, followed by Isoeleutherin and eleutherin. The new natural product 2,5-dimethyl-10-hydroxynaphthopyrone 8-O-beta-d-glucopyranoside occurred in percentages of less than 0.05%.