Guaiazulene
(Synonyms: 愈疮奥) 目录号 : GC38440
A sesquiterpene with diverse biological activities
Cas No.:489-84-9
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >99.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Guaiazulene is a sesquiterpene that has been found in M. chamomilla and has diverse biological activities.1,2,3 It inhibits lipid peroxidation in rat hepatic microsomes (IC50 = 9.8 μM), as well as scavenges hydroxyl and 2,2-diphenyl-1-picrylhydrazyl radicals in cell-free assays.1 It inhibits LPS-induced nitric oxide production in RAW 264.7 cells (EC50 = 10.1 μM) but is cytotoxic to RAW 264.7 cells at higher concentrations with cytotoxic concentration (CC50) values of 29.8 and 30.8 μM in the presence and absence, respectively, of LPS.2 Guaiazulene is cytotoxic to N2a neuroblastoma cells and primary rat neurons in a concentration-dependent manner.3 It inhibits decreases in hepatic glutathione (GSH) levels induced by paracetamol in rats when administered at a dose of 250 mg/kg.1
1.Kourounakis, A.P., Rekka, E.A., and Kourounakis, P.N.Antioxidant activity of guaiazulene and protection against paracetamol hepatotoxicity in ratsJ. Pharm. Pharmacol.49(9)938-942(1997) 2.Hashiba, K., Yokoyama, K., Wakabayashi, H., et al.Inhibition of LPS-stimulated NO production in mouse macrophage-like cells by azulenesAnticancer Res.24(6)3939-3944(2004) 3.Togar, B., Turkez, H., Hacimuftuoglu, A., et al.Guaiazulene biochemical activity and cytotoxic and genotoxic effects on rat neuron and N2a neuroblastom cellsJ. Intercult. Ethnopharmacol.4(1)29-33(2015)
| Cas No. | 489-84-9 | SDF | |
| 别名 | 愈疮奥 | ||
| Canonical SMILES | CC(C1=CC2=C(C)C=CC2=C(C)C=C1)C | ||
| 分子式 | C15H18 | 分子量 | 198.3 |
| 溶解度 | DMSO: 250 mg/mL (1260.72 mM) | 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 | 5.0429 mL | 25.2143 mL | 50.4286 mL |
| 5 mM | 1.0086 mL | 5.0429 mL | 10.0857 mL |
| 10 mM | 0.5043 mL | 2.5214 mL | 5.0429 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。
Guaiazulene and related compounds: A review of current perspective on biomedical applications
Life Sci 2023 Mar 1;316:121389.PMID:36646376DOI:10.1016/j.lfs.2023.121389.
Background: Thousands of people worldwide pass away yearly due to neurological disorders, cardiovascular illnesses, cancer, metabolic disorders, and microbial infections. Additionally, a sizable population has also been impacted by hepatotoxicity, ulcers, gastroesophageal reflux disease, and breast fissure. These ailments are likewise steadily increasing along with the increase in life expectancy. Finding innovative therapies to cure and consequently lessen the impact of these ailments is, therefore, a global concern. Methods and materials: All provided literature on Guaiazulene (GA) and its related compounds were searched using various electronic databases such as PubMed, Google Scholar, Web of Science, Elsevier, Springer, ACS, CNKI, and books via the keywords Guaiazulene, Matricaria chamomilla, GA-related compounds, and Guaiazulene analogous. Results: The FDA has approved the bicyclic sesquiterpene GA, commonly referred to as azulon or 1,4-dimethyl-7-isopropylazulene, as a component in cosmetic colorants. The pleiotropic health advantages of GA and related substances, especially their antioxidant and anti-inflammatory effects, attracted a lot of research. Numerous studies have found that GA can help to manage various conditions, including bacterial infections, tumors, immunomodulation, expectorants, diuretics, diaphoresis, ulcers, dermatitis, proliferation, and gastritis. These conditions all involve lipid peroxidation and inflammatory response. In this review, we have covered the biomedical applications of GA. Moreover, we also emphasize the therapeutic potential of Guaiazulene derivatives in pre-clinical and clinical settings, along with their underlying mechanism(s). Conclusion: GA and its related compounds exhibit therapeutic potential in several diseases. Still, it is necessary to investigate their potential in animal models for various other ailments and establish their safety profile. They might be a good candidate to advance to clinical trials.
C4-aldehyde of Guaiazulene: synthesis and derivatisation
Org Biomol Chem 2021 Mar 21;19(11):2502-2511.PMID:33661271DOI:10.1039/d0ob02567d.
Guaiazulene is an alkyl-substituted azulene available from natural sources and is a much lower cost starting material for the synthesis of azulene derivatives than azulene itself. Here we report an approach for the selective functionalisation of Guaiazulene which takes advantage of the acidity of the protons on the Guaiazulene C4 methyl group. The aldehyde produced by this approach constitutes a building block for the construction of azulenes substituted on the seven-membered ring. Derivatives of this aldehyde synthesised by alkenylation, reduction and condensation are reported, and the halochromic properties of a subset of these derivatives have been studied.
Design, Synthesis, and Biological Activity of Guaiazulene Derivatives
Chem Biodivers 2023 Feb;20(2):e202201174.PMID:36573597DOI:10.1002/cbdv.202201174.
Guaiazulene and related derivatives were famous for diverse biological activities. In an effort to discover new highly efficient candidate drugs derived from Guaiazulene, four series of Guaiazulene derivatives were designed, synthesized, and evaluated for antiproliferation, antiviral, anti-inflammatory and peroxisome proliferators-activated receptor γ (PPARγ) signalling pathway agonist activities. Among them, two Guaiazulene condensation derivatives showed selective cytotoxic activities towards K562 cell with IC50 values 5.21 μM and 5.14 μM, respectively, accompanied by slight effects on normal cell viability. For the first time, one Guaiazulene derivative from series I exhibited potent antiviral activity towards influenza A virus with IC50 of 17.5 μM. A guaiazulene-based chalcone showed higher anti-inflammatory activity than positive drug indomethacin with an inhibitory rate of 34.29 % in zebrafish model in vivo. One guaiazulene-based flavonoid could strongly agitate PPARγ pathway at 20 μM, indicating the potential of Guaiazulene derivatives to reduce obesity development and ameliorate hepatic steatosis. Preliminary in silico ADME studies predicted the excellent drug-likeness properties of bioactive Guaiazulene derivatives.
Guaiazulene Triggers ROS-Induced Apoptosis and Protective Autophagy in Non-small Cell Lung Cancer
Front Pharmacol 2021 Apr 15;12:621181.PMID:33935713DOI:10.3389/fphar.2021.621181.
Non-small cell lung cancer (NSCLC) is one of the most frequent cancers worldwide, yet effective treatment remains a clinical challenge. Guaiazulene (GYZ), a cosmetic color additive, has previously been characterized as a potential antitumor agent due to observed anticancer effects. However, the efficacy of GYZ in the treatment of NSCLC and the involved molecular mechanisms remain largely unknown. Here, we indicated a role for GYZ in the suppression of NSCLC both in vitro and in vivo via triggering reactive oxygen species (ROS)-induced apoptosis. Concomitantly, GYZ induced complete autophagic flux in NSCLC cells via inhibiting the Akt/mTOR signaling pathway, which displayed cytoprotective effect against GYZ-induced growth suppression. Accompanied with autophagy inhibition obviously enhanced the effects of GYZ. Notably, GYZ acts synergistically with paclitaxel in the suppression of NSCLC in vitro. Together, our results for the first time reported that GYZ suppressed the proliferation of NSCLC and suggested a potential strategy for inhibiting NSCLC growth by combinational use of GYZ and autophagy inhibitors.
Guaiazulene derivative 1,2,3,4-tetrahydroazuleno[1,2-b] tropone reduces the production of ATP by inhibiting electron transfer complex II
FEBS Open Bio 2021 Nov;11(11):2921-2932.PMID:34061471DOI:10.1002/2211-5463.13215.
Molecularly targeted therapy has been used for treatment of various types of cancer. However, cancer cells often acquire resistance to molecularly targeted drugs that inhibit specific molecular abnormalities, such as constitutive activation of kinases. Even in cancer cells that have acquired resistance, enhanced anabolism, including the synthesis of nucleotides, amino acids and lipids, is common to normal cancer cells. Therefore, there is a renewed interest in effectively eliminating cancer cells by specifically targeting their abnormal energy metabolism. Multiple strategies are currently being developed for mitochondrial-targeted cancer therapy, with agents targeting oxidative phosphorylation, glycolysis, the tricarboxylic acid cycle and apoptosis. In this study, we found that one of the Guaiazulene derivatives, namely, 1,2,3,4-tetrahydroazuleno[1,2-b] tropone (TAT), inhibited the proliferation of cancer cell lines stronger than that of normal cells. In addition, we showed that TAT inhibited energy production in cancer cell lines, resulting in apoptosis. Analyses done in cancer cell lines and in the animal model Caenorhabditis elegans suggested that TAT acts on the mitochondrial electron transfer complex II and suppresses cellular energy production by inhibiting oxidative phosphorylation across species. These results suggest that TAT could represent a novel anticancer agent that selectively targets mitochondria.