Allicin
(Synonyms: 大蒜素; Diallyl thiosulfinate) 目录号 : GC34462
A natural product with diverse biological activities
Cas No.:539-86-6
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
Allicin is a natural product originally isolated from A. sativum that has wide-ranging biological effects including antioxidative, anticancer, antimicrobial, and antifungal activities.1,2,3,4 It inhibits the cysteine proteases cathepsin B and L, facipain 2, and rhodesain with Ki values of 8.6 and 9.3, 1.04, and 5.31 ?M, respectively.5 It shows antiparasitic activity against P. falciparum (IC50 = 5.2 ?M) and T. b. brucei (IC50 = 13.8 ?M), the parasites that cause malaria and African sleeping sickness, respectively. Allicin (5-10 ?M) dose-dependently inhibits cell adhesion, invasion, and migration in various lung adenocarcinoma cell lines.2 It also alters the balance of tissue inhibitors of matrix metalloproteinases (TIMPs) and matrix metalloproteinases (MMPs), decreases phosphorylation of Akt, and decreases PI3K/Akt signaling.
1.Chan, J.Y., Yuen, A.C., Chan, R.Y., et al.A review of the cardiovascular benefits and antioxidant properties of allicinPhytother. Res.27(5)637-646(2013) 2.Huang, L., Song, Y., Lian, J., et al.Allicin inhibits the invasion of lung adenocarcinoma cells by altering tissue inhibitor of metalloproteinase/matrix metalloproteinase balance via reducing the activity of phosphoinositide 3-kinase/AKT signaling.Oncol. Lett.14(1)468-474(2017) 3.Ankri, S., and Mirelman, D.Antimicrobial properties of allicin from garlicMicrobes Infect.1(2)125-129(1999) 4.Burian, J.P., Sacramento, L.V.S., and Carlos, I.Z.Fungal infection control by garlic extracts (Allium sativum L.) and modulation of peritoneal macrophages activity in murine model of sporotrichosis.Braz. J. Biol.(2017) 5.Waag, T., Gelhaus, C., Rath, J., et al.Allicin and derivates are cysteine protease inhibitors with antiparasitic activityBioorg. Med. Chem. Lett.20(18)5541-5543(2010)
| Cas No. | 539-86-6 | SDF | |
| 别名 | 大蒜素; Diallyl thiosulfinate | ||
| Canonical SMILES | C=CCS(SCC=C)=O | ||
| 分子式 | C6H10OS2 | 分子量 | 162.27 |
| 溶解度 | DMSO : 5 mg/mL (30.81 mM);Water : < 0.1 mg/mL (insoluble) | 储存条件 | 4°C, away from moisture and 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 | 6.1626 mL | 30.8128 mL | 61.6257 mL |
| 5 mM | 1.2325 mL | 6.1626 mL | 12.3251 mL |
| 10 mM | 0.6163 mL | 3.0813 mL | 6.1626 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。
Allicin: chemistry and biological properties
Molecules 2014 Aug 19;19(8):12591-618.PMID:25153873DOI:10.3390/molecules190812591.
Allicin (diallylthiosulfinate) is a defence molecule from garlic (Allium sativum L.) with a broad range of biological activities. Allicin is produced upon tissue damage from the non-proteinogenic amino acid alliin (S-allylcysteine sulfoxide) in a reaction that is catalyzed by the enzyme alliinase. Current understanding of the Allicin biosynthetic pathway will be presented in this review. Being a thiosulfinate, Allicin is a reactive sulfur species (RSS) and undergoes a redox-reaction with thiol groups in glutathione and proteins that is thought to be essential for its biological activity. Allicin is physiologically active in microbial, plant and mammalian cells. In a dose-dependent manner Allicin can inhibit the proliferation of both bacteria and fungi or kill cells outright, including antibiotic-resistant strains like methicillin-resistant Staphylococcus aureus (MRSA). Furthermore, in mammalian cell lines, including cancer cells, Allicin induces cell-death and inhibits cell proliferation. In plants Allicin inhibits seed germination and attenuates root-development. The majority of Allicin's effects are believed to be mediated via redox-dependent mechanisms. In sub-lethal concentrations, Allicin has a variety of health-promoting properties, for example cholesterol- and blood pressure-lowering effects that are advantageous for the cardio-vascular system. Clearly, Allicin has wide-ranging and interesting applications in medicine and (green) agriculture, hence the detailed discussion of its enormous potential in this review. Taken together, Allicin is a fascinating biologically active compound whose properties are a direct consequence of the molecule's chemistry.
Antimicrobial properties of Allicin from garlic
Microbes Infect 1999 Feb;1(2):125-9.PMID:10594976DOI:10.1016/s1286-4579(99)80003-3.
Allicin, one of the active principles of freshly crushed garlic homogenates, has a variety of antimicrobial activities. Allicin in its pure form was found to exhibit i) antibacterial activity against a wide range of Gram-negative and Gram-positive bacteria, including multidrug-resistant enterotoxicogenic strains of Escherichia coli; ii) antifungal activity, particularly against Candida albicans; iii) antiparasitic activity, including some major human intestinal protozoan parasites such as Entamoeba histolytica and Giardia lamblia; and iv) antiviral activity. The main antimicrobial effect of Allicin is due to its chemical reaction with thiol groups of various enzymes, e.g. alcohol dehydrogenase, thioredoxin reductase, and RNA polymerase, which can affect essential metabolism of cysteine proteinase activity involved in the virulence of E. histolytica.
Anticancer potential of Allicin: A review
Pharmacol Res 2022 Mar;177:106118.PMID:35134476DOI:10.1016/j.phrs.2022.106118.
Phytochemicals have attracted attention in the oncological field because they are biologically friendly and have relevant pharmacological activities. Thanks to the intense and unique spicy aroma, garlic is one of the most used plants for cooking. Its consumption is correlated to health beneficial effects towards several chronic diseases, such as cancer, mainly attributable to Allicin, a bioactive sulfur compound stored in different plant parts in a precursor form. The objective of this review is to present and critically discuss the chemistry and biosynthesis of Allicin, its pharmacokinetic profile, its anticancer mechanisms and molecular targets, and its selectivity towards tumor cells. The research carried out so far revealed that Allicin suppresses the growth of different types of tumors. In particular, it targets many signaling pathways associated with cancer development. Future research directions are also outlined to further characterize this promising natural product.
Allicin Bioavailability and Bioequivalence from Garlic Supplements and Garlic Foods
Nutrients 2018 Jun 24;10(7):812.PMID:29937536DOI:10.3390/nu10070812.
Allicin is considered responsible for most of the pharmacological activity of crushed raw garlic cloves. However, when garlic supplements and garlic foods are consumed, Allicin bioavailability or bioequivalence (ABB) has been unknown and in question because Allicin formation from alliin and garlic alliinase usually occurs after consumption, under enzyme-inhibiting gastrointestinal conditions. The ABB from 13 garlic supplements and 9 garlic foods was determined by bioassay for 13 subjects by comparing the area under the 32-h concentration curve of breath allyl methyl sulfide (AMS), the main breath metabolite of Allicin, to the area found after consuming a control (100% ABB) of known Allicin content: homogenized raw garlic. For enteric tablets, ABB varied from 36⁻104%, but it was reduced to 22⁻57% when consumed with a high-protein meal, due to slower gastric emptying. Independent of meal type, non-enteric tablets gave high ABB (80⁻111%), while garlic powder capsules gave 26⁻109%. Kwai garlic powder tablets, which have been used in a large number of clinical trials, gave 80% ABB, validating it as representing raw garlic in those trials. ABB did not vary with alliinase activity, indicating that only a minimum level of activity is required. Enteric tablets (high-protein meal) disintegrated slower in women than men. The ABB of supplements was compared to that predicted in vitro by the dissolution test in the United States Pharmacopeia (USP); only partial agreement was found. Cooked or acidified garlic foods, which have no alliinase activity, gave higher ABB than expected: boiled (16%), roasted (30%), pickled (19%), and acid-minced (66%). Black garlic gave 5%. The mechanism for the higher than expected ABB for alliinase-inhibited garlic was explored; the results for an alliin-free/allicin-free extract indicate a partial role for the enhanced metabolism of γ-glutamyl S-allylcysteine and S-allylcysteine to AMS. In conclusion, these largely unexpected results (lower ABB for enteric tablets and higher ABB for all other products) provide guidelines for the qualities of garlic products to be used in future clinical trials and new standards for manufacturers of garlic powder supplements. They also give the consumer an awareness of how garlic foods might compare to the garlic powder supplements used to establish any allicin-related health benefit of garlic.
Allicin Improves Metabolism in High-Fat Diet-Induced Obese Mice by Modulating the Gut Microbiota
Nutrients 2019 Dec 2;11(12):2909.PMID:31810206DOI:10.3390/nu11122909.
Allicin, naturally present in the bulbs of the lily family, has anticancer, blood pressure lowering, blood fat lowering and diabetes improving effects. Recent studies have shown that Allicin promotes the browning of white adipocytes and reduces the weight gain of mice induced by high-fat diet. While the gut microbiota has a strong relationship with obesity and energy metabolism, the effect of Allicin on weight loss via gut microorganisms is still unclear. In this study, we treated obese mice induced by high-fat diet with Allicin to determine its effects on fat deposition, blood metabolic parameters and intestinal morphology. Furthermore, we used high-throughput sequencing on a MiSeq Illumina platform to determine the gut microorganisms' species. We found that Allicin significantly reduced the weight gain of obese mice by promoting lipolysis and thermogenesis, as well as blood metabolism and intestinal morphology, and suppressing hepatic lipid synthesis and transport. In addition, Allicin changed the composition of the intestinal microbiota and increased the proportion of beneficial bacteria. In conclusion, our study showed that Allicin improves metabolism in high-fat induced obese mice by modulating the gut microbiota. Our findings provide a theoretical basis for further elucidation of the weight loss mechanism of Allicin.