Alnustone
(Synonyms: 桤木酮) 目录号 : GC35296
Alnustone 是一种在草药和香料中发现的非酚双苯庚烷类化合物，是姜黄的成分之一。Alnustone 具有抗吐、抗炎作用。
Cas No.:33457-62-4
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
Alnustone, a non-phenolic diarylheptanoid found in herbs and spices, is a constituent of Curcuma xanthorrhiza. Alnustone displays anti-emetic and anti-inflammatory activities[1][2].
[1]. SÜleyman GÖksu, et al. An efficient synthesis of alnustone, a naturally occurring compound. Turkish Journal of Chemistry 27(1):31-34. [2]. Claeson P, et al. Three non-phenolic diarylheptanoids with anti-inflammatory activity from Curcuma xanthorrhiza. Planta Med. 1993 Oct;59(5):451-4.
| Cas No. | 33457-62-4 | SDF | |
| 别名 | 桤木酮 | ||
| Canonical SMILES | O=C(/C=C/C=C/C1=CC=CC=C1)CCC2=CC=CC=C2 | ||
| 分子式 | C19H18O | 分子量 | 262.35 |
| 溶解度 | Soluble in DMSO | 储存条件 | 4°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 | 3.8117 mL | 19.0585 mL | 38.117 mL |
| 5 mM | 0.7623 mL | 3.8117 mL | 7.6234 mL |
| 10 mM | 0.3812 mL | 1.9059 mL | 3.8117 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。
Alnustone inhibits the growth of hepatocellular carcinoma via ROS- mediated PI3K/Akt/mTOR/p70S6K axis
Phytother Res 2022 Jan;36(1):525-542.PMID:34847624DOI:10.1002/ptr.7337.
Alnustone, a diarylheptane compound, exhibits potent growth inhibition against hepatocellular carcinoma (HCC) BEL-7402 cells. However, the underlying mechanisms associated with its anticancer activity remain unknown. In the present study, we evaluated the anticancer effect of Alnustone against several human cancers focused on HCC and the possible associated mechanisms. The results showed that Alnustone significantly inhibited the growth of several cancer cells by CCK-8 assay. Alnustone markedly induced apoptosis and decreased mitochondrial membrane potential in BEL-7402 and HepG2 cells. Alnustone inhibited the expression of proteins related to apoptosis and PI3K/Akt/mTOR/p70S6K pathways and generated ROS production in BEL-7402 and HepG2 cells. Moreover, N-acetyl-L-cysteine (NAC, a ROS inhibitor) could significantly reverse the effects of Alnustone on the growth inhibition of BEL-7402 and HepG2 cells and the expression of proteins related to apoptosis and PI3K/Akt/mTOR signaling pathway in HepG2 cells. Furthermore, Alnustone significantly inhibited tumor growth of HepG2 xenografts, obviously induced apoptosis in the tumor tissues and improved the pathological condition of liver tissues of mice in vivo. The study provides evidence that Alnustone is effective against HCC via ROS-mediated PI3K/Akt/mTOR/p70S6K pathway and the compound has the potential to be developed as a novel anticancer agent for the treatment of HCC clinically.
Alnustone inhibits Streptococcus pneumoniae virulence by targeting pneumolysin and sortase A
Fitoterapia 2022 Oct;162:105261.PMID:35944753DOI:10.1016/j.fitote.2022.105261.
Streptococcus pneumoniae (S. pneumoniae) is a major Gram-positive opportunistic pathogen that causes pneumonia, bacteremia, and other fatal infections. This bacterium is responsible for more deaths than any other single pathogen in the world. Inexplicably, these symptoms persist despite the administration of effective antibiotics. Targeting pneumolysin (PLY) and sortase A (SrtA), the major virulence factors of S. pneumoniae, this study uncovered a novel resistance mechanism to S. pneumoniae infection. Using protein phenotype assays, we determined that the small molecule inhibitor Alnustone is a potent drug that inhibits both PLY and SrtA. As essential virulence factors of S. pneumoniae, PLY and SrtA play a significant role in the occurrence of infection. Furthermore, evaluation using PLY-mediated hemolysis assay demonstrated alunstone had the potential to interrupt the haemolytic activity of PLY with treatment alunstone (4 μg/ml). Co-incubation of S. pneumoniae D39 SrtA with small-molecule inhibitors decreases cell wall-bound Nan A (pneumococcal-anchored surface protein SrtA), inhibits biofilm formation, and reduces biomass significantly. The protective effect of invasive pneumococcal disease (IPD) on murine S. pneumoniae was demonstrated further. Our study proposes a comprehensive bacteriostatic mechanism for S. pneumoniae and highlights the significant translational potential of targeting both PLY and SrtA to prevent pneumococcal infections. Our findings indicate that the antibacterial strategy of directly targeting PLY and SrtA with Alnustone is a promising treatment option for S. pneumoniae and that Alnustone is a potent inhibitor of PLY and SrtA.
Pharmacokinetics and Tissue Distribution of Alnustone in Rats after Intravenous Administration by Liquid Chromatography-Mass Spectrometry
Molecules 2019 Sep 2;24(17):3183.PMID:31480657DOI:10.3390/molecules24173183.
Alnustone, a nonphenolic diarylheptanoid, first isolated from Alnus pendula (Betulaceae), has recently received a great deal of attention due to its various beneficial pharmacological effects. However, its pharmacokinetic profile in vivo remains unclear. The purpose of this study is to establish a fast and sensitive quantification method of Alnustone using liquid chromatography tandem mass spectrometry (LC-MS/MS) and evaluate the pharmacokinetic and tissue distribution profiles of Alnustone in rats. The sample was precipitated with acetonitrile with 0.5% formic acid and separated on BEH C18 Column. The mobile phase was composed of 0.1% formic acid in water and methanol at a flow rate of 0.3 mL/min. Alnustone and the internal standard (caffeine) were quantitatively monitored with precursor-to-product ion transitions of m/z 262.9→105.2 and m/z 195.2→138.0, respectively. The calibration curve for Alnustone was linear from 1 to 2000 ng/mL. The intra- and inter-day assay precision (RSD) ranged from 1.1-9.0 % to 3.3-8.6%, respectively and the intra- and inter-day assay accuracy (RE) was between -8.2-9.7% and -10.3-9.9%, respectively. The validated method was successfully applied to the pharmacokinetic studies of Alnustone in rats. After single-dose intravenous administration of Alnustone (5 mg/kg), the mean peak plasma concentration (Cmax) value was 7066.36 ± 820.62 ng/mL, and the mean area under the concentration-time curve (AUC0-t) value was 6009.79 ± 567.30 ng/mL∙h. Our results demonstrated that the residence time of Alnustone in vivo was not long and it eliminated quickly from the rat plasma. Meanwhile, the drug is mainly distributed in tissues with large blood flow, and the lung and liver might be the target organs for Alnustone efficacy. The study will provide information for further application of Alnustone.
Syntheses and antibacterial activities of 4 linear nonphenolic diarylheptanoids
Turk J Chem 2020 Jun 1;44(3):589-601.PMID:33488179DOI:10.3906/kim-1911-61.
Four linear nonphenolic diarylheptanoids were synthesized and their antibacterial activities were studied. ( S )-2-Me-CBS-catalysed reduction of Alnustone with BH3SMe2 gave ( R )(-)(4 E ,6 E )-1,7-diphenylhepta-4,6-dien-3-ol, a natural product. Reduction of Alnustone with Na in t -BuOH at -15 °C under N3 atm gave (E)-1,7-diphenylhept-5- en-3-one as a Birch-type reduction product. t-BuOK catalysed condensation of benzalacetone with propionyl chloride gave (4 Z ,6 E )-5-hydroxy-1,7-diphenylhepta-4,6-dien-3-one, a natural product. (1 E ,4 Z ,6 E )-5-Hydroxy-4-phenethyl-1,7-diphenylhepta-1,4,6-trien-3-one, a curcuminoid, was synthesized starting from pentan-2,4-dione in 3 steps. The synthesized chemical compounds were applied against 2 gram-positive bacteria ( Bacillus cereus and Arthrobacter agilis ), 4 gram-negative bacteria ( Pseudomonas aeruginosa , Xanthomonas campestris , Klebsiella oxytoca , and Helicobacter pylori ), and 1 yeast (Candida albicans) by the disc diffusion method. All of the synthesized compound exhibited different degrees of antimicrobial activity at concentrations between 20-100 μg/disc against the test organisms.
[Qualitative and quantitative methods for Alpiniae Katsumadai semen]
Zhongguo Zhong Yao Za Zhi 2010 Aug;35(16):2091-4.PMID:21046736doi
The qualitative and quantitative methods for the quality evaluation of Alpiniae Katsumadai Semen were established. Alpinetin, pinocembrin, cardamonin and Alnustone in the sample were identified by TLC. The contents of them were determined by HPLC. The separation was performed on a Ultimate XB-C18 column (4.6 mm x 250 mm, 5 microm) at 30 degrees C using a gradient elution consisting of mobile phase A (water) and mobile phase B (MeOH). The detection wavelength was 300 nm. The TLC method was suitable for the identification of alpinetin, pinocembrin, cardamonin and Alnustone. The linear ranges of the four reference compounds were 25.5-509 (r = 0.9999), 24.9-498 (r = 0.9999), 26.1-521 (r = 0.9999), 50.2-1003 ng (r = 0.9999), respectively. The average recoveries (n=9) of the four components were 97.95%, 97.36%, 97.50%, 98.02%, RSD < 1.9%. Nine samples were analyzed by the established methods. The results indicate that, the methods are simple, accurate, sensitive and reliable for quality evaluation of Alpiniae Katsumadai Semen.