S-Allyl-L-cysteine
(Synonyms: S-烯丙基-L-半胱氨酸; S- 烯丙基别半胱氨酸) 目录号 : GC30205
A water soluble organosulfur compound derived from garlic
Cas No.:21593-77-1
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >97.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
L-
1.Kim, J.M., Chang, H.J., Kim, W.K., et al.Structure-activity relationship of neuroprotective and reactive oxygen species scavenging activities for allium organosulfur compoundsJ. Agric. Food Chem.546547-6553(2006) 2.Colín-González, A.L., Santana, R.A., Silva-Islas, C.A., et al.The antioxidant mechanisms underlying the aged garlic extract- and S-allylcysteine-induced protectionOxid. Med. Cell. Longev.2012(2012)
| Cas No. | 21593-77-1 | SDF | |
| 别名 | S-烯丙基-L-半胱氨酸; S- 烯丙基别半胱氨酸 | ||
| Canonical SMILES | N[C@@H](CSCC=C)C(O)=O | ||
| 分子式 | C6H11NO2S | 分子量 | 161.22 |
| 溶解度 | Water : 33.33 mg/mL (206.74 mM) | 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 | 6.2027 mL | 31.0135 mL | 62.027 mL |
| 5 mM | 1.2405 mL | 6.2027 mL | 12.4054 mL |
| 10 mM | 0.6203 mL | 3.1014 mL | 6.2027 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。
Neuroprotective mechanisms of S-Allyl-L-cysteine in neurological disease
Exp Ther Med 2020 Feb;19(2):1565-1569.32010340 PMC6966174
S-Allyl-L-cysteine (SAC) is a sulfur-containing amino acid present in garlic and exhibits a wide range of biological activities such as antioxidant, anti-inflammatory, and anticancer agent. An earlier study demonstrated that SAC ameliorates oxidative damage in a model of experimental stroke. However, the antioxidant property of SAC does not suffice to explain its beneficial effects in terms of the underlying mechanisms. Endoplasmic reticulum (ER) stress and ER stress-induced cell death have been shown to be involved in various neurological diseases such as brain ischemia, Alzheimer's disease, Parkinson's disease, amyotrophic lateral sclerosis and Huntington's disease. We have previously demonstrated that SAC exerts significant protective effects against ER stress-induced neurotoxicity in cultured rat hippocampal neurons and organotypic hippocampal slice cultures. Recently, we demonstrated that these results are due to the direct suppression of calpain activity via the binding of SAC to this enzyme's Ca2+-binding domain. We also found that the protective effects of the side-chain-modified SAC derivatives, S-ethyl-L-cysteine (SEC) and S-propyl-L-cysteine (SPC), against ER stress-induced neurotoxicity were more potent than those of SAC in cultured rat hippocampal neurons. In addition, SAC, SEC and SPC have been shown to decrease the production of amyloid-β peptide in the brains of mice with D-galactose-induced aging. These three hydrophilic cysteine-containing compounds have also been shown to exert neuroprotective effects against dopaminergic neuron injury in a murine model of Parkinson's disease induced by 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP). In this review, we aim to provide a current overview of the protective actions of SAC and the SAC-related compounds, SEC and SPC, in neurodegenerative disease and discuss the promise of SAC as a prototype for developing novel therapeutic drugs for neurological diseases.
Characteristics, biosynthesis, decomposition, metabolism and functions of the garlic odour precursor, S-Allyl-L-cysteine sulfoxide
Exp Ther Med 2020 Feb;19(2):1528-1535.32010334 PMC6966203
S-Allyl-L-cysteine sulfoxide (ACSO) is an odour precursor in garlic bulbs. One plausible pathway for the biosynthesis of ACSO involves S-2-carboxypropyl glutathione produced from glutathione and methacrylic acid via valine or from γ-glutamyl cysteine. The elimination of glycine and glutamic acid from S-2-carboxypropyl glutathione produces S-2-carboxypropyl cysteine, which is converted to S-allyl cysteine by decarboxylation and oxidation. S-Allyl cysteine is also biosynthesized via the elimination of glutamic acid from γ-glutamyl S-allyl cysteine by γ-glutamyl transpeptidase. The sulfur oxidation of S-allyl cysteine by flavin-containing monooxygenase forms ACSO. When cells are damaged by slicing or grating, ACSO in the cytoplasm or cytoplasmic vesicle is immediately converted to allylsulfenic acid, pyruvic acid, and ammonia by alliinase (C-S lyase), which is located in the vacuoles of vascular bundle sheath cells. Two molecules of allylsulfenic acid form diallyl thiosulfinate (allicin), which exhibits potent antimicrobial activity. Allicin eventually yields garlic odour compounds, such as diallyl disulfide (DADS) and diallyl trisulfide (DATS). Although these sulfides are known to exert various physiological functions, their strong odour limits their use in foods. On the other hand, ACSO is water-soluble and odourless and enhances sweet, salty, and umami tastes, characteristics of which are desirable for food additives. Upon consumption, ACSO is primarily absorbed from the small intestine in the intact form, but is also partly decomposed to allylsulfenic acid, pyruvic acid and ammonia. Allylsulfenic acid is then further converted to DADS and diallyl monosulfide (DAS). ACSO has numerous in vivo functions, such as the prevention of diabetes, myocardial ischaemia, hepatic injury, platelet aggregation and blood ethanol elevation. Although some of these effects may be attributed to its metabolites, ACSO itself contributes to many of these physiological functions.
l-Tryptophan-starved cultivation enhances S-Allyl-L-cysteine synthesis in various food-related microorganisms
Biosci Biotechnol Biochem 2022 May 24;86(6):792-799.35388878 10.1093/bbb/zbac044
S-Allyl-L-cysteine (SAC) has received much interest due to its beneficial effects on human health. To satisfy the increasing demand for SAC, this study aims to develop a valuable culturing method for microbial screening synthesizing SAC from readily available materials. Although tryptophan synthase is a promising enzyme for SAC synthesis, its expression in microorganisms is strictly regulated by environmental l-tryptophan. Thus, we constructed a semisynthetic medium lacking l-tryptophan using casamino acids. This medium successfully enhanced the SAC-synthesizing activity of Lactococcus lactis ssp. cremoris NBRC 100676. In addition, microorganisms with high SAC-synthesizing activity were screened by the same medium. Food-related Klebsiella pneumoniae K-15 and Pantoea agglomerans P-3 were found to have a significantly increased SAC-synthesizing activity. The SAC-producing process established in this study is shorter in duration than the conventional garlic aging method. Furthermore, this study proposes a promising alternative strategy for producing food-grade SAC by microorganisms.
S-Allyl-L-cysteine (SAC) protects hepatocytes from alcohol-induced apoptosis
FEBS Open Bio 2019 Jul;9(7):1327-1336.31161729 PMC6609569
Hepatocyte apoptosis is frequently observed in alcohol-related liver disease (ARLD), which ranks among the 30 leading causes of death worldwide. In the current study, we explored the impact of S-Allyl-L-cysteine (SAC), an organosulfur component of garlic, on hepatocyte apoptosis induced by alcohol. Rat liver (BRL-3A) cells were challenged by ethanol with or without SAC treatment. Cell death/viability, reactive oxygen species (ROS) generation, mitochondrial Cytochrome C release, and caspase 3 activity were then examined. We found that ethanol remarkably induced apoptosis of hepatocytes, while SAC treatment rescued ethanol-induced hepatocyte injury, as demonstrated by cell counting kit-8 (CCK8) assay, TUNEL assay, and annexin V/PI staining assay. Ethanol evoked ROS generation in BRL-3A cells, and this was abated by SAC pretreatment, as indicated by 2',7'-dichlorofluorescin diacetate (DCFDA) staining assay. Moreover, ethanol suppressed cellular anti-apoptotic protein B-cell lymphoma-2 (Bcl-2) expression, increased pro-apoptotic protein Bcl-2-associated X protein (Bax) expression, induced mitochondrial Cytochrome C release, and activated the caspase 3-dependent apoptosis pathway in BRL-3A cells. SAC was sufficient to abolish all these changes induced by ethanol, thereby revealing the molecular mechanisms underlying its protective effects. In conclusion, SAC protects hepatocytes from ethanol-induced apoptosis and may be suitable for use as a novel anti-apoptotic agent for treating ARLD.
Antioxidant Interactions between S-Allyl-L-cysteine and Polyphenols Using Interaction Index and Isobolographic Analysis
Molecules 2022 Jun 25;27(13):4089.35807335 PMC9268411
This work aims to study the antioxidant interactions between S-Allyl-L-cysteine (SAC) and six natural polyphenols (quercetin, caffeic acid, sinapic acid, catechin, ferulic acid, and 3,4-dihydroxybenzoic acid) through the measurement of free-radical-scavenging activity of 1,1-diphenyl- 2-picryl-hydrazyl (DPPH), the radical-cation-scavenging activity of 2,2-azino-bis-3-ethylbenzothiazoline-6-sulfonic acid (ABTS), and reducing power. Among the six natural polyphenols, caffeic acid showed the strongest synergistic effect with SAC according to DPPH and reducing power assays. Further investigations based on the results of interaction index and isobologram analysis showed that the antioxidant activity (DPPH, ABTS, and reducing power) of the combination of caffeic acid with SAC presented an increase with the raising of their individual concentrations in their mixture and along with a dose-response manner. The best synergistic effect between caffeic acid and SAC based on DPPH, ABTS, and reducing power assays were observed at the ratio of 1:20, 1:35, and 1:70, respectively. The excellent synergic antioxidant activity of the combination of caffeic acid with SAC in our study suggests SAC has a more broad and effective application prospects in food field.