Glucoraphanin
(Synonyms: 萝卜硫苷) 目录号 : GC32999
A natural compound with protective effects
Cas No.:21414-41-5
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
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Animal experiment: |
Male C57BL/6JSlc mice are 7 weeks of age. The Nrf2 knockout (Nrf2−/−) mouse strain is used in the assay. After 1 week of acclimation, mice are fed normal chow (NC) (containing 2.2% dextrinized cornstarch, 10% kcal from fat), NC containing 0.3% glucoraphanin (NC-GR) (containing 2.2% extract powder), an HFD (containing 2.2% dextrinized cornstarch, 60% kcal from fat), or an HFD containing 0.3% glucoraphanin (HFD-GR) (containing 2.2% extract powder) for 14 weeks. Both the NC and the HFD containing cornstarch or glucoraphanin are prepared. All mice studied are maintained on a 12-h light/dark cycle at 24-26°C with free access to water and food. |
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References: [1]. Nagata N, et al. Glucoraphanin Ameliorates Obesity and Insulin Resistance Through Adipose Tissue Browning and Reduction of Metabolic Endotoxemia in Mice. Diabetes. 2017 May;66(5):1222-1236. |
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Glucoraphanin is a natural glycoinsolate found in cruciferous vegetables, including broccoli.1 It is converted to the isothiocyanate sulforaphane by the enzyme myrosinase.1 Sulforaphane has powerful antioxidant, anti-
1.James, D., Devaraj, S., Bellur, P., et al.Novel concepts of broccoli sulforaphanes and disease: Induction of phase II antioxidant and detoxification enzymes by enhanced-glucoraphanin broccoliNutr. Rev.70(11)654-665(2012) 2.Liang, H., and Yuan, Q.Natural sulforaphane as a functional chemopreventive agent: Including a review of isolation, purification and analysis methodsCrit. Rev. Biotechnol.32(3)218-234(2012) 3.La Marca, M., Beffy, P., Della Croce, C., et al.Structural influence of isothiocyanates on expression of cytochrome P450, phase II enzymes, and activation of Nrf2 in primary rat hepatocytesFood Chem. Toxicol.50(8)2822-2830(2012) 4.Dinkova-Kostova, A.T., Holtzclaw, W.D., Cole, R.N., et al.Direct evidence that sulfhydryl groups of Keap1 are the sensors regulating induction of phase 2 enzymes that protect against carcinogens and oxidantsProc. Natl. Acad. Sci. USA99(18)11908-11913(2012)
| Cas No. | 21414-41-5 | SDF | |
| 别名 | 萝卜硫苷 | ||
| Canonical SMILES | CS(CCCC/C(S[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)CO)=N\OS(=O)(O)=O)=O | ||
| 分子式 | C12H23NO10S3 | 分子量 | 437.51 |
| 溶解度 | Water : ≥ 76.5 mg/mL (174.85 mM) | 储存条件 | Store at -20°C, protect from light |
| 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 | 2.2857 mL | 11.4283 mL | 22.8566 mL |
| 5 mM | 0.4571 mL | 2.2857 mL | 4.5713 mL |
| 10 mM | 0.2286 mL | 1.1428 mL | 2.2857 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。
Glucoraphanin: a broccoli sprout extract that ameliorates obesity-induced inflammation and insulin resistance
Adipocyte 2018;7(3):218-225.PMID:29898626DOI:10.1080/21623945.2018.1474669.
Obesity is a low-grade sustained inflammatory state that causes oxidative stress in different metabolic tissues, which leads to insulin resistance and nonalcoholic fatty liver disease (NAFLD). Particularly, obesity-induced metabolic endotoxemia plays an important role in the pathogenesis of insulin resistance and inflammation. Nuclear factor erythroid 2-related factor 2 (Nrf2) is a key regulator of antioxidant signaling that serves as a primary cellular defense against the cytotoxic effects of oxidative stress. Pharmacological stimulation of Nrf2 mitigates obesity and insulin resistance in mice; however, Nrf2 activators are not clinically available due to biosafety concerns. A recent study demonstrated that Glucoraphanin, a precursor of the Nrf2 activator sulforaphane, ameliorates obesity by enhancing energy expenditure and browning of white adipose tissue, and attenuates obesity-related inflammation and insulin resistance by polarizing M2 macrophages and reducing metabolic endotoxemia. Thus, this review focuses on the efficiency and safety of Glucoraphanin in alleviating obesity, insulin resistance, and NAFLD. Abbreviations: ALT, Alanine aminotransferase; AMPK, AMP-activated protein kinase; ATMs, Adipose tissue macrophages; BAT, Brown adipose tissue; CDDO-Im, 2-cyano-3,12-dioxoolean-1,9-dien-28-oic acid-imidazolide; CDDO-Me, CDDO-methyl ester; DIO, High-fat-diet-induced obese; FFA, Free fatty acid; FGF, Fibroblast growth factor; GTP, Glutamyl transpeptidase; HFD, High-fat diet; IKKβ, Inhibitor of κB-kinase β; IL, Interleukin; JNK, C-Jun N-terminal kinase; KD, Knockdown; Keap1, Kelch-like ECH-associated protein 1; KO, Knockout; LPS, Lipopolysaccharide; NADPH, Nicotinamide adenine dinucleotide phosphate; NAFLD, Non-alcoholic fatty liver disease; NF-κB, Nuclear factor-κB; Nrf2, Nuclear factor E2-related factor 2; ROS, Reactive oxygen species; T2D, Type 2 diabetes; TLR, Toll-like receptor; TNF, tumor necrosis factor; UCP, Uncoupling protein; WAT, White adipose tissue.
Bioavailability of Glucoraphanin and Sulforaphane from High-Glucoraphanin Broccoli
Mol Nutr Food Res 2018 Sep;62(18):e1700911.PMID:29266773DOI:10.1002/mnfr.201700911.
Scope: Broccoli accumulates 4-methylsulphinylbutyl glucosinolate (Glucoraphanin) which is hydrolyzed to the isothiocyanate sulforaphane. Through the introgression of novel alleles of the Myb28 transcription factor from Brassica villosa, broccoli genotypes have been developed that have enhanced levels of Glucoraphanin. This study seeks to quantify the exposure of human tissues to Glucoraphanin and sulforaphane following consumption of broccoli with contrasting Myb28 genotypes. Methods and results: Ten participants are recruited into a three-phase, double-blinded, randomized crossover trial (NCT02300324), with each phase comprising consumption of 300 g of a soup made from broccoli of one of three Myb28 genotypes (Myb28B/B , Myb28B/V , Myb28V/V ). Plant myrosinases are intentionally denatured during soup manufacture. Threefold and fivefold higher levels of sulforaphane occur in the circulation following consumption of Myb28V/B and Myb28V/V broccoli soups, respectively. The percentage of sulforaphane excreted in 24 h relative to the amount of Glucoraphanin consumed varies among volunteers from 2 to 15%, but does not depend on the broccoli genotype. Conclusion: This is the first study to report the bioavailability of Glucoraphanin and sulforaphane from soups made with novel broccoli varieties. The presence of one or two Myb28V alleles results in enhanced delivery of sulforaphane to the systemic circulation.
Isothiocyanate from Broccoli, Sulforaphane, and Its Properties
J Med Food 2019 Feb;22(2):121-126.PMID:30372361DOI:10.1089/jmf.2018.0024.
Sulforaphane is an isothiocyanate occurring in stored form as Glucoraphanin in cruciferous vegetables such as cabbage, cauliflower, and kale, and at high levels in broccoli especially in broccoli sprouts. Glucoraphanin requires the plant enzyme myrosinase for converting it into sulforaphane. Sulforaphane is metabolized through mercapturic acid pathway, being conjugated with glutathione and undergoes further biotransformation, yielding metabolites. Sulforaphane is extensively investigated and is in the interest in medicine for its health benefits. It has been shown that sulforaphane may protect against various types of cancer, may also decrease the risk of cardiovascular disease, and help in autism and osteoporosis. Our review offers a short summary of interesting properties of sulforaphane. Both the in vitro and in vivo methods/models and clinical studies are mentioned.
Optimization of Heterologous Glucoraphanin Production In Planta
ACS Synth Biol 2022 May 20;11(5):1865-1873.PMID:35438493DOI:10.1021/acssynbio.2c00030.
Glucoraphanin is a plant specialized metabolite found in cruciferous vegetables that has long been a target for production in a heterologous host because it can subsequently be hydrolyzed to form the chemopreventive compound sulforaphane before and during consumption. However, previous studies have only been able to produce small amounts of Glucoraphanin in heterologous plant and microbial systems compared to the levels found in glucoraphanin-producing plants, suggesting that there may be missing auxiliary genes that play a role in improving production in planta. In an effort to identify auxiliary genes required for high Glucoraphanin production, we leveraged transient expression in Nicotiana benthamiana to screen a combination of previously uncharacterized coexpressed genes and rationally selected genes alongside the Glucoraphanin biosynthetic pathway. This strategy alleviated metabolic bottlenecks, which improved Glucoraphanin production by 4.74-fold. Our optimized Glucoraphanin biosynthetic pathway provides a pathway amenable for high Glucoraphanin production.
Efficacy of Sulforaphane in Neurodegenerative Diseases
Int J Mol Sci 2020 Nov 16;21(22):8637.PMID:33207780DOI:10.3390/ijms21228637.
Sulforaphane (SFN) is a phytocompound belonging to the isothiocyanate family. Although it was also found in seeds and mature plants, SFN is mainly present in sprouts of many cruciferous vegetables, including cabbage, broccoli, cauliflower, and Brussels sprouts. SFN is produced by the conversion of Glucoraphanin through the enzyme myrosinase, which leads to the formation of this isothiocyanate. SFN is especially characterized by antioxidant, anti-inflammatory, and anti-apoptotic properties, and for this reason, it aroused the interest of researchers. The aim of this review is to summarize the experimental studies present on Pubmed that report the efficacy of SFN in the treatment of neurodegenerative disease, including Alzheimer's disease (AD), Parkinson's disease (PD), and multiple sclerosis (MS). Therefore, thanks to its beneficial effects, SFN could be useful as a supplement to counteracting neurodegenerative diseases.