Carabrone
(Synonyms: 天名精内酯酮) 目录号 : GC35604
Carabrone 天名精内酯酮从 Carpesium abrotanoides 的果实中分离出来，是一种倍半萜，具有显着的抗菌和抗肿瘤活性。Carabrone 在体内外具有抗真菌活性，抗灰霉病菌 Botrytis cinerea，炭疽病菌 Colletotrichum lagenarium 和禾白粉菌 Erysiphe graminis。
Cas No.:1748-81-8
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
Carabrone is isolated from the fruits of Carpesium abrotanoides , is a well-known sesquiterpene and exhibits significant anti-bacterial and anti-tumor activities[1].Carabrone exhibits antifungal activities in vitro and in vivo against Botrytis cinerea, Colletotrichum lagenarium(EC50=7.10 μg/mL) and Erysiphe graminis[2]. EC50: 7.10 μg/mL (Colletotrichum lagenarium)[1]
[1]. Wang H, et al. Synthesis, antifungal activities and qualitative structure activity relationship of carabrone hydrazone derivatives as potential antifungal agents. [2]. Feng JT, et al. Synthesis and antifungal activity of carabrone derivatives. Molecules. 2010 Sep 16;15(9):6485-92.
| Cas No. | 1748-81-8 | SDF | |
| 别名 | 天名精内酯酮 | ||
| Canonical SMILES | O=C1O[C@@]2([H])[C@@](C[C@]([C@@H]3CCC(C)=O)([H])[C@]3(C)C2)([H])C1=C | ||
| 分子式 | C15H20O3 | 分子量 | 248.32 |
| 溶解度 | Soluble in DMSO | 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 | 4.0271 mL | 20.1353 mL | 40.2706 mL |
| 5 mM | 0.8054 mL | 4.0271 mL | 8.0541 mL |
| 10 mM | 0.4027 mL | 2.0135 mL | 4.0271 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。
A Carabrane-Type Sesquiterpenolide Carabrone from Carpesium cernuum Inhibits SW1990 Pancreatic Cancer Cells by Inducing Ferroptosis
Molecules 2022 Sep 9;27(18):5841.PMID:36144577DOI:10.3390/molecules27185841.
Pancreatic cancer has an extremely poor prognosis, and the clinical drugs for the treatment of pancreatic cancer are usually multi-drug combinations. Therefore, it is necessary to search for and find specific new bioactive agents against pancreatic cancer. Carabrone is a carabrane-type sesquiterpenolide extracted from Carpesium cernuum L., and this natural compound has been reported to be a potential anti-tumor agent. However, there are few reports on the function of Carabrone related to anti-tumor activity in pancreatic cancer. Herein, cell experiments indicated that Carabrone had anti-proliferation inhibition and anti-migration and anti-invasion activity against SW1990 cells. Furthermore, the tandem mass spectrometry and network pharmacology analysis showed that this activity may be related to the ferroptosis and Hippo signaling pathway. Taken together, our results demonstrated that Carabrone exhibited prominent anti-pancreatic cancer activity and could be a promising agent against pancreatic cancer.
The effect of Carabrone on mitochondrial respiratory chain complexes in Gaeumannomyces graminis
J Appl Microbiol 2017 Nov;123(5):1100-1110.PMID:28783246DOI:10.1111/jam.13554.
Aims: To evaluate the effect of Carabrone on mitochondrial respiratory chain complexes in Gaeumannomyces graminis to identify Carabrone targets. Methods and results: The influence of Carabrone on mitochondria in G. graminis mycelia was determined, and the activity of complexes I-V, citrate synthase, and respiratory chain complexes I+III and II+III was evaluated following treatment with 30% effective concentration (EC30 ) as well as EC50 and EC70 of Carabrone for 0, 6, 12 and 24 h. Quantitative real-time PCR analysis of the relative expression of genes encoding mitochondrial respiratory chain complexes was then conducted. Carabrone treatment influenced the activity of mitochondrial respiratory chain complexes III, I+III, and II+III in G. graminis in a dose- and time-dependent manner with a marked decrease (c. 50% compared to the control) in mitochondrial respiratory chain complex III activity following treatment with Carabrone at the EC50 . The GgCyc1 was downregulated following Carabrone treatment at the EC50 , and the other genes were upregulated with respect to the control. Conclusions: This study showed that mitochondrial respiratory chain complex III in G. graminis is highly sensitive to Carabrone and is a potential target of this botanical fungicidal agent. Significance and impact of the study: Carabrone is a promising botanical fungicidal agent that is environmentally friendly and can control plant diseases and reduce chemical fungicides in agricultural production.
Oxidative Stress and Apoptosis of Gaeumannomyces graminis ( Get) Induced by Carabrone
J Agric Food Chem 2019 Sep 18;67(37):10448-10457.PMID:31453693DOI:10.1021/acs.jafc.9b02951.
Carabrone is isolated from Carpesium macrocephalum Franch. et Sav, which has good fungicidal activity, especially for Gaeumannomyces graminis (Get). According to previous studies, we speculated that Carabrone targets the mitochondrial enzyme complex III of Get. To elucidate the mode of action, we used Carabrone to induce oxidative stress and apoptosis in Get. Incubation with Carabrone reduced the burst of reactive oxygen species (ROS) and mitochondrial membrane potential, as well as phosphatidylserine release. Carabrone caused ROS accumulation in mycelia by inhibiting the activity of antioxidase enzymes, among which inhibition of glutathione reductase (GR) activity was most obvious. The catalytic center of GR consists of l-cysteine residues that react with the α-methylene-γ-butyrolactone active site of Carabrone. Additionally, a positive TUNEL reaction led to diffusion of the DNA electrophoresis band and upregulation of Ggmet1 and Ggmet2. We propose that Carabrone inhibits antioxidant enzymes and promotes ROS overproduction, which causes membrane hyperpermeability, release of apoptotic factors, activation of the mitochondria-mediated apoptosis pathway, and fungal cell apoptosis.
A functional analysis of mitochondrial respiratory chain cytochrome bc1 complex in Gaeumannomyces tritici by RNA silencing as a possible target of Carabrone
Mol Plant Pathol 2020 Dec;21(12):1529-1544.PMID:32997435DOI:10.1111/mpp.12993.
Gaeumannomyces tritici, an ascomycete soilborne fungus, causes a devastating root disease in wheat. Carabrone, a botanical bicyclic sesquiterpenic lactone, is a promising fungicidal agent that can effectively control G. tritici. However, the mechanism of action of Carabrone against G. tritici remains largely unclear. Here, we used immunogold for subcellular localization of Carabrone and the results showed that Carabrone is subcellularly localized in the mitochondria of G. tritici. We then explored the functional analysis of genes GtCytc1 , GtCytb, and GtIsp of the mitochondrial respiratory chain cytochrome bc1 complex in G. tritici by RNA silencing as a possible target of Carabrone. The results showed that the silenced mutant ∆GtIsp is less sensitive to Carabrone compared to ∆GtCytc1 and ∆GtCytb. Compared with the control, the activities of complex III in all the strains, except ∆GtIsp and carabrone-resistant isolate 24-HN-1, were significantly decreased following treatment with Carabrone at EC20 and EC80 in vitro (40%-50% and 70%-80%, respectively). The activities of mitochondrial respiratory chain complex III and the mitochondrial respiration oxygen consumption rates in all the strains, except ∆GtIsp and 24-HN-1, were higher with respect to the control when treated with Carabrone at EC20 in vivo. The rates of mitochondrial respiration of all strains, except ∆GtIsp, were significantly inhibited following treatment with Carabrone at EC80 (ranging from 57% to 81%). This study reveals that the targeting of the iron-sulphur protein encoded by GtIsp is highly sensitive to Carabrone and provides a direction for the research of Carabrone's target.
Synthesis and antifungal activity of Carabrone derivatives
Molecules 2010 Sep 16;15(9):6485-92.PMID:20877238DOI:10.3390/molecules15096485.
Nine derivatives 6-14 of Carabrone (1) were synthesized and tested in vitro against Colletotrichum lagenarium Ell et Halst using the spore germination method. Among all of the derivatives, compounds 6-8 and 12 showed more potent antifungal activity than 1. Structure-activity relationships (SAR) demonstrated that the γ-lactone was necessary for the antifungal activity of 1, and the substituents on the C-4 position of 1 could significantly affect the antifungal activity.