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Diallyl Tetrasulfide

(Synonyms: 二烯丙基四硫醚,ICD-1585) 目录号 : GC45992

An organosulfur compound with diverse biological activities

Diallyl Tetrasulfide Chemical Structure

Cas No.:2444-49-7

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Diallyl tetrasulfide is an organosulfur compound that has been found in A. sativum and has diverse biological activities, including antimicrobial, antioxidant, and anticancer properties.[1],[2],[3],[4] It is active against the bacteria S. aureus and methicillin-resistant S. aureus (MRSA; MICs = 0.5 and 2 mg/L, respectively), as well as the fungi C. albicans, C. krusei, C. glabrata, A. niger, A. flavus, and A. fumigatus (MICs = 0.5, 4, 2, 1, 2, and 4 mg/L, respectively).[1] It reduces cadmium-induced increases in hepatic levels of thiobarbituric acid reactive substances (TBARS) and increases cadmium-induced decreases in the hepatic activity of superoxide dismutase (SOD1), catalase, GST, and glucose-6-phosphate dehydrogenase (G6PDH) in rats when administered at a dose of 40 mg/kg.[2] Diallyl tetrasulfide is cytotoxic to MCF-7 breast cancer cells (IC50 = 92 μM) and reduces tumor growth in a BGC-823 mouse xenograft model when administered at doses of 20, 30, and 40 mg/kg for 32 days.[3],[4]

[1]. Tsao, S.-M., and Yin, M.-C. In-vitro antimicrobial activity of four diallyl sulphides occurring naturally in garlic and Chinese leek oils. J. Med. Microbiol. 50(7), 646-649 (2001).
[2]. Murugavel, P., and Pari, L. Effects of diallyl tetrasulfide on cadmium-induced oxidative damage in the liver of rats. Hum. Exp. Toxicol. 26(6), 527-534 (2007).
[3]. Viry, E., Anwar, A., Kirsch, G., et al. Antiproliferative effect of natural tetrasulfides in human breast cancer cells is mediated through the inhibition of the cell division cycle 25 phosphatases. Int. J. Oncol. 38(4), 1103-1111 (2011).
[4]. Jiang, X.-Y., Zhu, X.-S., Xu, H.-Y., et al. Diallyl trisulfide suppresses tumor growth through the attenuation of Nrf2/Akt and activation of p38/JNK and potentiates cisplatin efficacy in gastric cancer treatment. Acta Pharmacol. Sin. 38(7), 1048-1058 (2017).

Chemical Properties

Cas No. 2444-49-7 SDF
别名 二烯丙基四硫醚,ICD-1585
化学名 di-2-propen-1-yl tetrasulfide
分子式 C6H10S4 分子量 210.4
溶解度 30mg/mL in DMSO, 30mg/mL in DMF, 30mg/mL in Ethanol 储存条件 Store at -20°C
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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。
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1 mg 5 mg 10 mg
1 mM 4.7529 mL 23.7643 mL 47.5285 mL
5 mM 0.9506 mL 4.7529 mL 9.5057 mL
10 mM 0.4753 mL 2.3764 mL 4.7529 mL
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Research Update

Diallyl Tetrasulfide protects cadmium-induced alterations in lipids and plasma lipoproteins in rats

Nutr Res 2007 Jun;27(6):356-361.PMID:32726894DOI:10.1016/j.nutres.2007.04.012.

Lipoprotein abnormalities disrupt the levels of serum and cellular lipid, which accounts for the genesis of cardiovascular diseases. Cadmium (Cd) exposure is associated with a number of distinct pathological changes including dyslipidemia. Garlic and its organosulfur compounds seem to hold promise in reducing the risk factors associated with cardiovascular disease. The present study was undertaken to assess the effect of Diallyl Tetrasulfide (DTS) from garlic on Cd-induced alterations in the levels of lipids and lipoproteins in Wistar rats. Subcutaneous administration of Cd (3 mg/[kg body weight d]) for 3 weeks showed a significant (P < .05) increase in total cholesterol, very low density lipoprotein cholesterol, low-density lipoprotein cholesterol, triglycerides, free fatty acids, and phospholipids, with a significant (P < .05) reduction in high-density lipoprotein cholesterol in plasma. In addition, the activity of hydroxy-3-methylglutaryl-coenzyme A reductase and the levels of cholesterol, free fatty acids, and triglycerides were significantly (P < .05) increased and the level of phospholipids was significantly decreased (P < .05) in liver of Cd-treated rats. Oral administration ofDTS (40 mg/[kg body weight d]) significantly (P < .05) reduced the levels of cholesterol, free fatty acids, triglycerides, very low density lipoprotein cholesterol, and low-density lipoprotein cholesterol; but the activity of hepatic hydroxy-3-methylglutaryl-coenzyme A reductase and the levels of high-density lipoprotein cholesterol increased (P < .05) in Cd-treated rats. Our results indicate that the administration of DTS afforded remarkable protection against Cd-induced alterations in lipid metabolism and thereby reduced the Cd-mediated cardiovascular diseases.

Diallyl Tetrasulfide modulates the cadmium-induced impairment of membrane bound enzymes in rats

J Basic Clin Physiol Pharmacol 2007;18(1):37-48.PMID:17569245DOI:10.1515/jbcpp.2007.18.1.37.

Cadmium (Cd) induces extensive membrane damage that contributes to the cytotoxic effect of Cd. We studied the effect of Diallyl Tetrasulfide (DTS) from garlic on Cd-induced changes in lipid peroxidation and membrane-bound enzymes in liver, kidney, and testis of rats. Cadmium exposure (3 mg/kg body weight, s.c) for 3 weeks induced a significant elevation in the levels of lipid peroxidation markers (thiobarbituric acid substances and lipid hydroperoxides) with a significant decrease in the activities of membrane bound ATPases (Na+/K+ ATPase, Ca2+ ATPase, Mg2+ ATPase), the indicators of membrane function in liver, kidney and testis. The oral administration of DTS (40 mg/kg body weight) along with Cd significantly decreased the level of lipid peroxidation and significantly restored the activities of membrane bound ATPases. The results of our study suggest that DTS attenuates lipid peroxidation in tissues and promotes the stability of the membrane by protecting it from Cd-induced alterations.

Comparison between the effects of Diallyl Tetrasulfide on human retina pigment epithelial cells (ARPE-19) and HCT116 cells

Biochim Biophys Acta 2013 Nov;1830(11):5267-76.PMID:23948592DOI:10.1016/j.bbagen.2013.08.004.

Background: Diallyl mono- and polysulfanes from garlic are known to induce an adaptive cell response and the formation of antioxidants in cancer cells. In the case of a severe ER stress and a failure in the response, cancer cells eventually go into apoptosis. Only little is known about the response of normal cells upon treatment. Methods: Normal ARPE-19 cells were treated with Diallyl Tetrasulfide to study their cellular response and the results were compared with those of HCT116 cancer cells. Cell viability was checked by an MTT assay and cytofluorimetry. The formation of superoxide radicals, H2O2 and thiols were determined and proteins involved in the ER stress response were also detected by Western blot analysis. Results: We found that Diallyl Tetrasulfide induced reactive oxygen species (ROS) in normal cells similar to cancer cells in a time (0 to 60min) and dose dependent manner (0 to 50μM). The level of heme oxigenase-1 (HO-1) was up-regulated in both cell types. Initially, we found a decrease in the total thiol level in both cell types but in contrast to cancer cells, normal cells recovered from the decrease in the total thiol concentration within 60min of treatment. Conclusions: The recovery of the thiol concentration in normal cells treated with Diallyl Tetrasulfide seems to be responsible for the failure to induce the ER stress signalling pathway and finally apoptosis in normal cells. General significance: The difference in the recovery of the thiol status might be an explanation for the anti-carcinogenic effects of garlic compounds.

Effects of Diallyl Tetrasulfide on cadmium-induced oxidative damage in the liver of rats

Hum Exp Toxicol 2007 Jun;26(6):527-34.PMID:17698948DOI:10.1177/0960327107073810.

The protective efficacy of Diallyl Tetrasulfide (DTS) from garlic on liver injury induced by cadmium (Cd) was investigated. In this study, Cd (3 mg/kg body weight) was administered subcutaneously for 3 weeks to induce toxicity. DTS was administered orally (10, 20 and 40 mg/kg body weight) for 3 weeks with subcutaneous (sc) injection of Cd. Cd-induced liver damage was evidenced from increased activities of serum hepatic enzymes, namely aspartate transaminase, alanine transaminase, alkaline phosphatase and lactate dehydrogenase, with significant elevation of lipid peroxidation indices (thiobarbituric acid reactive substances and hydroperoxides) and protein carbonyl groups in the liver. Rats subjected to Cd toxicity also showed a decline in the levels of total thiols, reduced glutathione (GSH), vitamin C and vitamin E, accompanied by an increased accumulation of Cd, and significantly decreased activities of superoxide dismutase, catalase (CAT), glutathione peroxidase, glutathione-S-transferase (GST), glutathione reductase, and glucose-6-phosphate dehydrogenase in the liver. Administration of DTS at 40 mg/kg body weight significantly normalised the activities of hepatic marker enzymes, compared to other doses of DTS (10 and 20 mg/kg body weight). In addition, DTS (40 mg/kg body weight) significantly reduced the accumulation of Cd and the level of lipid peroxidation, and restored the level of antioxidant defense in the liver. Histological studies also showed that administration of DTS to Cd-treated rats resulted in a marked improvement of hepatocytes morphology with mild portal inflammation. Our results suggest that DTS might play a vital role in protecting Cd-induced oxidative damage in the liver.

Protective role of Diallyl Tetrasulfide on cadmium-induced testicular damage in adult rats: a biochemical and histological study

Toxicol Ind Health 2011 Jun;27(5):407-16.PMID:21245201DOI:10.1177/0748233710387633.

Cadmium (Cd)-induced oxidative damage is the most serious problem that leads to reproductive system failure in both human and animals. Our previous studies indicate that Diallyl Tetrasulfide (DTS) from garlic has the cytoprotective and antioxidant activity against Cd-induced toxicity in vivo and in vitro. The present investigation was carried out to find the influence of DTS on peroxidative damage induced by Cd in rat testes. The Cd-exposed rat testis showed a significant (p < 0.05) decrease in testes to body weight ratio, along with a significant (p < 0.05) increase in Cd accumulation, lipid peroxidation and protein carbonyl levels. In Cd-exposed rats, we also observed a significant (p < 0.05) decrease in the activities of antioxidant (superoxide dismutase, catalase and glutathione peroxidase) and glutathione metabolizing (glutathione-S-transferase, glutathione reductase and glucose-6-phosphate dehydrogenase) enzymes as well as reduced levels of non-enzymic (reduced glutathione, ascorbate and total sulphydryl groups) antioxidants. In contrast, treatment with DTS (40 mg/kg body weight orally) significantly (p < 0.05) reduced the accumulation of Cd and lipid peroxidation markers and also significantly improved the activities of antioxidant defense system in testes. Testicular protection by DTS is further substantiated by remarkable reduction of Cd-induced pathological changes. Our study has revealed that DTS renders protection against Cd-induced testicular injury by reducing Cd-mediated oxidative damage.