Cardol triene
目录号 : GC41400
A phenol from cashew nut shell liquid
Cas No.:79473-24-8
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >95.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Cardol triene is a phenol found in cashew nut shell liquid that competitively and irreversibly inhibits mushroom tyrosinase (IC50 = 22.5 µM). It is schistosomicidal, killing 25, 75, and 100% of S. mansoni worms after 24 hours when used at concentrations of 50, 100, or 200 µM, respectively. It has been used as a starting material for the synthesis of bis-benzoxazines.
| Cas No. | 79473-24-8 | SDF | |
| Canonical SMILES | OC1=CC(O)=CC(CCCCCCC/C=C\C/C=C\CC=C)=C1 | ||
| 分子式 | C21H30O2 | 分子量 | 314.5 |
| 溶解度 | DMF: 20 mg/ml,DMSO: 15 mg/ml,Ethanol: 22 mg/ml,Ethanol:PBS(pH 7.2) (1:1): 0.5 mg/ml | 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 | 3.1797 mL | 15.8983 mL | 31.7965 mL |
| 5 mM | 0.6359 mL | 3.1797 mL | 6.3593 mL |
| 10 mM | 0.318 mL | 1.5898 mL | 3.1797 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。
Cardol triene inhibits dengue infectivity by targeting kl loops and preventing envelope fusion
Sci Rep 2018 Nov 9;8(1):16643.PMID:30413789DOI:10.1038/s41598-018-35035-w.
Dengue virus causes a global burden that specific chemotherapy has not been established. A previous report suggested that anacardic acid inhibited hepatitis C virus infection. Here, we explored structure activity relationship of anacardic acid, cardanol, and cardol homologues with anti-DENV cellular infectivities. Cardol triene showed the highest therapeutic index at 29.07 with the CC50 and EC50 of 207.30 ± 5.24 and 7.13 ± 0.72 µM, respectively. Moreover, we observed that the more unsaturated the hydrocarbon tail, the higher the CC50s in all head groups. High CC50s were also found in HepG-2, THP-1, and HEK-293 cell lines where Cardol triene CC50s were 140.27 ± 8.44, 129.77 ± 12.08, and 92.80 ± 3.93 µM, respectively. Cardol triene expressed pan-dengue inhibition with the EC50s of 5.35 to 8.89 µM and kl loops of dengue envelope proteins were major targets. The strong binding energy at T48, E49, A50, P53, K128, V130, L135, M196, L198, Q200, W206, L207, I270, and L277 prevented cellular pH-dependent fusion. Zika virus kl loops were aligned in the closed position preventing Cardol triene to bind and inhibit fusion and infectivity. This study showed for the first time that Cardol triene had a potential for further development as anti-dengue inhibitors.
Irreversible competitive inhibitory kinetics of Cardol triene on mushroom tyrosinase
J Agric Food Chem 2010 Dec 22;58(24):12993-8.PMID:21121650DOI:10.1021/jf103723k.
Cardol triene was first purified from cashew (Anacardium occidentale L.) nut shell liquid and identified by gas chromatography coupled to mass spectroscopy and nuclear magnetic resonance. The effects of this compound on the activity of mushroom tyrosinase were studied. The results of the kinetic study showed that Cardol triene was a potent irreversible competitive inhibitor and the inactivation was of the complexing type. Two molecules of Cardol triene could bind to one molecule of tyrosinase and lead to the complete loss of its catalytic activity. The microscopic rate constants were determined for the reaction of Cardol triene with the enzyme. The anti-tyrosinase kinetic research of this study provides a comprehensive understanding of inhibitory mechanisms of resorcinolic lipids and is beneficial for the future design of novel tyrosinase inhibitors.
Schistosomicidal Activity of Alkyl-phenols from the Cashew Anacardium occidentale against Schistosoma mansoni Adult Worms
J Agric Food Chem 2016 Nov 23;64(46):8821-8827.PMID:27934289DOI:10.1021/acs.jafc.6b04200.
Bioassay-guided study of the ethanol extract from the cashew Anacardium occidentale furnished Cardol triene (1), cardol diene (2), anacardic acid triene (3), cardol monoene (4), anacardic acid diene (5), 2-methylcardol triene (6), and 2-methylcardol diene (7). 1D- and 2D-NMR experiments and HRMS analysis confirmed the structures of compounds 1-7. Compounds 2 and 7 were active against Schistosoma mansoni adult worms in vitro, with LC50 values of 32.2 and 14.5 μM and selectivity indices of 6.1 and 21.2, respectively. Scanning electron microscopy of the tegument of male worms in the presence of compound 7 at 25 μM after 24 h of incubation showed severe damage as well as peeling and reduction in the number of spine tubercles. Transmission electron microscopy analyses revealed swollen mitochondrial membrane, vacuoles, and altered tegument in worms incubated with compound 2 (25 μM after 24 h). Worms incubated with compound 7 (25 μM after 24 h) had lysed interstitial tissue, degenerated mitochondria, and drastically altered tegument. Together, the results indicated that compound 7 presents promising in vitro schistosomicidal activity.