Juglone
(Synonyms: 胡桃醌; 5-Hydroxy-1,4-naphthalenedione) 目录号 : GC43933
An allelopathic naphthoquinone
Cas No.:481-39-0
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >97.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Juglone is a natural naphthoquinone found in the black walnut (J. nigra) and other plants in the Juglandaceae family. It has allelopathic actions, suppressing growth, photosynthesis, and respiration in plants and other organisms, although some bacteria can metabolize juglone. Juglone also irreversibly inhibits peptidyl-prolyl cis/trans isomerases of the parvulin family, including human Pin1, yeast Ess1/Ptf1, and E. coli parvulin (Ki = 55.9 nM). Juglone also blocks transcription by RNA polymerases I, II, and III (IC50s = 2-7 µM) and attenuates kidney fibrosis in rats treated with unilateral ureteral obstruction, both through Pin1-independent mechanisms.
| Cas No. | 481-39-0 | SDF | |
| 别名 | 胡桃醌; 5-Hydroxy-1,4-naphthalenedione | ||
| Canonical SMILES | O=C1C=CC(C2=CC=CC(O)=C21)=O | ||
| 分子式 | C10H6O3 | 分子量 | 174.2 |
| 溶解度 | DMSO: 10 mg/ml,Ethanol: 10 mg/ml | 储存条件 | 4°C, protect from light ,unstable in solution, ready to use. |
| 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 | 5.7405 mL | 28.7026 mL | 57.4053 mL |
| 5 mM | 1.1481 mL | 5.7405 mL | 11.4811 mL |
| 10 mM | 0.5741 mL | 2.8703 mL | 5.7405 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。
Juglone: A Versatile Natural Platform for Obtaining New Bioactive Compounds
Curr Top Med Chem 2021;21(22):2018-2045.PMID:34348624DOI:10.2174/1568026621666210804121054.
Juglone is a metabolite produced by several species of plants, in particular Juglans nigra. Additionally, Juglone is a 1,4-naphthoquinone that has several biological actions. Antimicrobial, antifungal, sedative, oxidizing, antihypertensive, and especially anti-proliferative actions have been described for Juglone. This justifies that 1,4-naphthoquinone is a privileged structure for Medicinal Chemistry, and it is useful for the development of new prototypes with varied actions. In this work, we make a profound review of Juglone synthesis methodology, the biological actions of Juglone, and mainly the synthesis and pharmacological actions of Juglone derivatives. We hope that the potent biological actions described for these derivatives in this review will stimulate the continuous design, synthesis, and pharmacological evaluation of new Juglone derivatives.
Juglone in Oxidative Stress and Cell Signaling
Antioxidants (Basel) 2019 Apr 5;8(4):91.PMID:30959841DOI:10.3390/antiox8040091.
Juglone (5-hydroxyl-1,4-naphthoquinone) is a phenolic compound found in walnuts. Because of the antioxidant capacities of phenolic compounds, Juglone may serve to combat oxidative stress, thereby protecting against the development of various diseases and aging processes. However, being a quinone molecule, Juglone could also act as a redox cycling agent and produce reactive oxygen species. Such prooxidant properties of Juglone may confer health effects, such as by killing cancer cells. Further, recent studies revealed that Juglone influences cell signaling. Notably, Juglone is an inhibitor of Pin1 (peptidyl-prolyl cis/trans isomerase) that could regulate phosphorylation of Tau, implicating potential effects of Juglone in Alzheimer's disease. Juglone also activates mitogen-activated protein kinases that could promote cell survival, thereby protecting against conditions such as cardiac injury. This review describes recent advances in the understanding of the effects and roles of Juglone in oxidative stress and cell signaling.
Juglone regulates gut microbiota and Th17/Treg balance in DSS-induced ulcerative colitis
Int Immunopharmacol 2021 Aug;97:107683.PMID:33915494DOI:10.1016/j.intimp.2021.107683.
Juglone, mainly isolates from the green walnut husks of Juglans mandshurica, exhibits anti-cancer and anti-inflammaroty activities. But its protection on ulcerative colitis (UC) has never been explored. In this study, we first evaluated whether Juglone ameliorated UC, and investigated its effects on gut microbiota and Th17/Treg balance in DSS-induced UC mice model. The model was established by administrating 2.7% DSS for seven days. Juglone was given daily by gavage for ten days, once a day. The disease activity index (DAI) decrease and pathological characteristics improvement demonstrated that the UC in mice was alleviated by Juglone. Juglone treatment significantly inhibited the protein levels of IL-6, TNF-α and IL-1β, improved the protein expression of IL-10. In addition, Juglone altered microbial diversity and gut microbiota composition, including the enhancement of the ratio of Firmicutes to Bacteroidota and the abundance of Actinobacteriota, and decrease of the abundance of Verrucomicrobiota. Juglone treatment also inhibited the protein expressions of IL-6, STAT3 and RORγt, meanwhile improved the protein level of FOXP3. Furthermore, Juglone inhibited Th17 development and increased Treg generation, beneficial to Th17/Treg balance. Together, we herein provided the first evidence to support that Juglone, especially the high dose, possibly protected mice against UC by modulating gut microbiota and restoring Th17/Treg homeostasis.
Juglone Suppresses Inflammation and Oxidative Stress in Colitis Mice
Front Immunol 2021 Aug 5;12:674341.PMID:34421890DOI:10.3389/fimmu.2021.674341.
Juglone (JUG), a natural product found in walnut trees and other plants, shows potent antioxidant, antimicrobial, and immunoregulatory activities. However, it remains unknown whether JUG can alleviate ulcerative colitis. This study aims to explore the effect of JUG on dextran sulfate sodium (DSS)-induced colitis in mice. The mice were randomly assigned into three groups: the vehicle group, the DSS group, and the JUG group. The experiments lasted for 17 days; during the experiment, all mice received dimethyl sulfoxide (DMSO, 0.03% v/v)-containing water, while the mice in the JUG group received DMSO-containing water supplemented with JUG (0.04 w/v). Colitis was induced by administering DSS (3% w/v) orally for 10 consecutive days. The results showed that the JUG treatment significantly ameliorated body weight loss and disease activity index and improved the survival probability, colon length, and tissue damage. JUG reversed the DSS-induced up-regulation of proinflammatory cytokines, including interleukin (IL)-6, 12, 21, and 23, and tumor necrosis factor-alpha, and anti-inflammatory cytokines, such as IL-10 and transforming growth factor-beta, in the serum of the colitis mice. Additionally, the activation of mitochondrial uncoupling protein 2 and phospho-Nuclear Factor-kappa B p65 and the inhibition of the kelch-like ECH-associated protein 1 and NF-E2-related factor 2 induced by DSS were also reversed under JUG administration. Although the JUG group possessed a similar microbial community structure as the DSS group, JUG enriched potential beneficial microbes such as Lachnospiraceae_NK4A136_group but not pathogens such as Escherichia Shigella, which was dominative in DSS group, at the genus level. In conclusion, our results demonstrated that JUG could be a promising agent for UC prevention to regulate inflammatory cytokines and oxidative stress.
Juglone Inhibits Listeria monocytogenes ATCC 19115 by Targeting Cell Membrane and Protein
Foods 2022 Aug 24;11(17):2558.PMID:36076744DOI:10.3390/foods11172558.
Foodborne disease caused by Listeria monocytogenes is a major global food safety problem. A potential solution is the antimicrobial development of the highly bioactive natural product Juglone, yet few studies exist on its antibacterial mechanism against L. monocytogenes. Thus, we aimed to elucidate the antibacterial mechanism of action of Juglone against L. monocytogenes by determining the resultant cell morphology, membrane permeability, membrane integrity, and proteome changes. The minimum inhibitory concentration of Juglone against L. monocytogenes was 50 μg/mL, and L. monocytogenes treated with Juglone had longer lag phases compared to controls. Juglone induced L. monocytogenes cell dysfunction, leakage of potassium ions, and membrane potential hyperpolarization. Confocal laser scanning microscopy and field-emission-gun scanning electron microscope assays revealed clear membrane damage due to Juglone treatment. Fourier transform infrared analyses showed that L. monocytogenes responded to Juglone by some conformational and compositional changes in the molecular makeup of the cell membrane. Sodium dodecyl sulfate-polyacrylamide gel electrophoresis analysis showed that Juglone either destroyed proteins or inhibited proteins synthesis in L. monocytogenes. Therefore, our findings established Juglone as a natural antibacterial agent with potential to control foodborne L. monocytogenes infections.