Elemicin
(Synonyms: 榄香素) 目录号 : GC38436
A trioxygenated phenylpropane
Cas No.:487-11-6
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
Elemicin is a trioxygenated phenylpropane that has been found in A. dracunculus.1 It is active against S. aureus, B. subtilis, and C. albicans (MICs = 600, 2,500, and 1,000 mg/L, respectively) but not E. coli, K. pneumoniae, P. aeruginosa (MICs = >8,000 mg/L for all), or L. monocytogenes (MIC = >3,000 mg/L). Elemicin is toxic to mice following metabolic activation to 1’-hydroxyelemicin by the cytochrome P450 (CYP) isoforms CYP1A1 and CYP1A2.2 It increases plasma and hepatic triglyceride levels, decreases stearoyl-CoA desaturase 1 (Scd1) expression, and induces hepatomegaly in mice when administered at a dose of 500 mg/kg per day for three weeks.
1.Pauli, A., and Kubeczka, K.H.Antimicrobial properties of volatile phenylpropanesNat. Prod. Commun.5(9)1387-1394(2010) 2.Yang, X.N., Wang, Y.K., Zhu, X., et al.Metabolic activation of elemicin leads to the inhibition of stearoyl-CoA desaturase 1Chem. Res. Toxicol.32(10)195-1976(2019)
| Cas No. | 487-11-6 | SDF | |
| 别名 | 榄香素 | ||
| Canonical SMILES | C=CCC1=CC(OC)=C(OC)C(OC)=C1 | ||
| 分子式 | C12H16O3 | 分子量 | 208.25 |
| 溶解度 | DMSO: ≥ 250 mg/mL (1200.48 mM) | 储存条件 | Store at 2-8°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 | 4.8019 mL | 24.0096 mL | 48.0192 mL |
| 5 mM | 0.9604 mL | 4.8019 mL | 9.6038 mL |
| 10 mM | 0.4802 mL | 2.401 mL | 4.8019 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。
Myristicin and Elemicin: Potentially Toxic Alkenylbenzenes in Food
Foods 2022 Jul 5;11(13):1988.PMID:35804802DOI:10.3390/foods11131988.
Alkenylbenzenes represent a group of naturally occurring substances that are synthesized as secondary metabolites in various plants, including nutmeg and basil. Many of the alkenylbenzene-containing plants are common spice plants and preparations thereof are used for flavoring purposes. However, many alkenylbenzenes are known toxicants. For example, safrole and methyleugenol were classified as genotoxic carcinogens based on extensive toxicological evidence. In contrast, reliable toxicological data, in particular regarding genotoxicity, carcinogenicity, and reproductive toxicity is missing for several other structurally closely related alkenylbenzenes, such as myristicin and Elemicin. Moreover, existing data on the occurrence of these substances in various foods suffer from several limitations. Together, the existing data gaps regarding exposure and toxicity cause difficulty in evaluating health risks for humans. This review gives an overview on available occurrence data of myristicin, Elemicin, and other selected alkenylbenzenes in certain foods. Moreover, the current knowledge on the toxicity of myristicin and Elemicin in comparison to their structurally related and well-characterized derivatives safrole and methyleugenol, especially with respect to their genotoxic and carcinogenic potential, is discussed. Finally, this article focuses on existing data gaps regarding exposure and toxicity currently impeding the evaluation of adverse health effects potentially caused by myristicin and Elemicin.
Role of Metabolic Activation in Elemicin-Induced Cellular Toxicity
J Agric Food Chem 2019 Jul 24;67(29):8243-8252.PMID:31271289DOI:10.1021/acs.jafc.9b02137.
Elemicin, an alkenylbenzene constituent of natural oils of several plant species, is widely distributed in food, dietary supplements, and medicinal plants. 1'-Hydroxylation is known to cause metabolic activation of alkenylbenzenes leading to their potential toxicity. The aim of this study was to explore the relationship between Elemicin metabolism and its toxicity through comparing the metabolic maps between Elemicin and 1'-hydroxyelemicin. Elemicin was transformed into a reactive metabolite of 1'-hydroxyelemicin, which was subsequently conjugated with cysteine (Cys) and N-acetylcysteine (NAC). Administration of NAC could significantly ameliorate the elemicin- and 1'-hydroxyelemicin-induced cytotoxicity of HepG2 cells, while depletion of Cys with diethyl maleate (DEM) increased cytotoxicity. Recombinant human CYP screening and CYP inhibition experiments revealed that multiple CYPs, notably CYP1A1, CYP1A2, and CYP3A4, were responsible for the metabolic activation of Elemicin. This study revealed that metabolic activation plays a critical role in Elemicin cytotoxicity.
Elemicin exposure induced aberrant lipid metabolism via modulation of gut microbiota in mice
Toxicology 2022 Feb 15;467:153088.PMID:34979169DOI:10.1016/j.tox.2021.153088.
Elemicin (Ele) is a constituent of natural alkenylbenzene present in many foods and herbs. Ele exposure could induce hepatomegaly and hepatosteatosis. However, the role of gut microbiota in Ele-induced hepatotoxicity remains unclear. Here, the mice were treated with 200 mg/kg/day of Ele for 4 weeks with or without depletion of gut microbiota by antibiotics cocktail treatment. The mice treated with Ele showed enlargement of liver and slight hepatosteatosis, accompanied by higher levels of serum alanine aminotransferase (ALT), aspartate aminotransferase (AST), triglyceride (TG). Ele could also shift the structure of fecal microbiota and increase the richness. Functional prediction of the microbiota revealed the enrichment of non-alcoholic fatty liver disease pathway upon Ele exposure. Compared with control group, Patescibacteria and Epsilonbacteraeota were significantly enriched at the phylum level upon Ele treatment. A total of 20 genera were significant with respect specifically to Ele exposure, including decreased Alistipes and elevated Ruminiclostridium_9 and Gordonibacter. Among them, 13 retained significant associations with ALT and TG by Spearman correlation test, 4 were correlated with AST. Further MaAsLin analysis revealed that ALT was associated with 4 differentially abundant genera, such as Alistipes and Ruminiclostridium_9 and Gordonibacter. In addition, only Alistipes was significantly correlated with serum TG. Intriguingly, depletion of the microbiota significantly attenuated hepatosteatosis, restore increased ALT, AST and TG and inhibit the expression of genes involved in de novo lipogenesis and adipocyte differentiation, such as Fasn, ADIPOQ and leptin. Collectively, depletion of gut microbiota protected against Ele induced aberrant lipid metabolism in mice.
Metabolic Activation of Elemicin Leads to the Inhibition of Stearoyl-CoA Desaturase 1
Chem Res Toxicol 2019 Oct 21;32(10):1965-1976.PMID:31468958DOI:10.1021/acs.chemrestox.9b00112.
Elemicin is a constituent of natural aromatic phenylpropanoids present in many herbs and spices. However, its potential to cause toxicity remains unclear. To examine the potential toxicity and associated mechanism, Elemicin was administered to mice for 3 weeks and serum metabolites were examined. Enlarged livers were observed in elemicin-treated mice, which were accompanied by lower ratios of unsaturated- and saturated-lysophosphatidylcholines in plasma, and inhibition of stearoyl-CoA desaturase 1 (Scd1) mRNA expression in liver. Administration of the unsaturated fatty acid oleic acid reduced the toxicity of 1'-hydroxylelemicin, the primary oxidative metabolite of Elemicin, while treatment with the SCD1 inhibitor A939572 potentiated its toxicity. Furthermore, the in vitro use of recombinant human CYPs and chemical inhibition of CYPs in human liver microsomes revealed that CYP1A1 and CYP1A2 were the primary CYPs responsible for Elemicin bioactivation. Notably, the CYP1A2 inhibitor α-naphthoflavone could attenuate the susceptibility of mice to elemicin-induced hepatomegaly. This study revealed that metabolic activation of Elemicin leads to SCD1 inhibition in liver, suggesting that upregulation of SCD1 may serve as potential intervention strategy for elemicin-induced toxicity.
Constituents of aromatic plants: Elemicin
Fitoterapia 2004 Sep;75(6):615-8.PMID:15351123DOI:10.1016/j.fitote.2004.05.003.
No results of short-term or chronic toxicity studies have been found. Elemicin did induce UDS in hepatocytes from male rats. Studies on carcinogenicity were negative, but the 1'-hydroxy-metabolite of Elemicin gave positive and negative results. The total intake of Elemicin from essential oil seems to be limited. The main source of intake appears to be nutmeg. Further studies are needed to evaluate if the intake of Elemicin may represent a health risk.