Allylglutathione sulphide

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Allylglutathione sulphide
• 英文别名: S-2-propenylmercapto-L-glutathione；S-allyl glutathione disulfide；S-allyl-mercapto-glutathione；allyl glutathionyl disulfide；S-allylmercaptoglutathione；S-allylthio-glutathione；(2S)-2-amino-5-[[(2R)-1-(carboxymethylamino)-1-oxo-3-(prop-2-enyldisulfanyl)propan-2-yl]amino]-5-oxopentanoic acid
• 化学式: C₁₃H₂₁N₃O₆S₂
• 分子量: 379.458
• InChiKey: GWIWSTVHQDDXNU-IUCAKERBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.5
• 重原子数：
  24
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  209
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  卡托普利 、 Allylglutathione sulphide 反应 2.5h， 生成 谷胱甘肽 、 卡托普利-谷胱甘肽混合二硫化物
  参考文献：
  名称：

  大蒜素和烯丙基混合二硫化物与蛋白质和硫醇小分子的反应机理

  摘要：

  大蒜中的烯丙基硫化物是化学预防剂。预期进入的细胞最初会与谷胱甘肽相互作用。因此，在无细胞系统中分析了产物S-烯丙基硫代谷胱甘肽与模型蛋白和硫醇的反应机理。以谷胱甘肽，半胱氨酰基或卡托普利代表S-烯丙基脂族加合物，与巯基的反应产生由S-烯丙基和脂族部分两者形成的混合二硫化物混合物。 为了改善常规的血压前药治疗，癌症和肠道炎症合成了S-烯丙基硫代前药，例如S-烯丙基硫代6-巯基嘌呤和S-烯丙基硫代-卡托普利。2种成分的协同活性以及增加的细胞渗透性允许有效的体内活性。这些衍生物与谷胱甘肽反应后，形成S-烯丙基硫代-谷胱甘肽，而6-巯基嘌呤为离去基团。过量的细胞谷胱甘肽使巯基-二硫键交换反应发生数个周期，从而扩展了杂合药物的药效学。

  DOI：

  10.1016/j.ejmech.2010.01.031
• 作为产物：
  描述：

  谷胱甘肽 、 大蒜素 以 乙醇 为溶剂， 生成 Allylglutathione sulphide
  参考文献：
  名称：

  大蒜素和烯丙基混合二硫化物与蛋白质和硫醇小分子的反应机理

  摘要：

  大蒜中的烯丙基硫化物是化学预防剂。预期进入的细胞最初会与谷胱甘肽相互作用。因此，在无细胞系统中分析了产物S-烯丙基硫代谷胱甘肽与模型蛋白和硫醇的反应机理。以谷胱甘肽，半胱氨酰基或卡托普利代表S-烯丙基脂族加合物，与巯基的反应产生由S-烯丙基和脂族部分两者形成的混合二硫化物混合物。 为了改善常规的血压前药治疗，癌症和肠道炎症合成了S-烯丙基硫代前药，例如S-烯丙基硫代6-巯基嘌呤和S-烯丙基硫代-卡托普利。2种成分的协同活性以及增加的细胞渗透性允许有效的体内活性。这些衍生物与谷胱甘肽反应后，形成S-烯丙基硫代-谷胱甘肽，而6-巯基嘌呤为离去基团。过量的细胞谷胱甘肽使巯基-二硫键交换反应发生数个周期，从而扩展了杂合药物的药效学。

  DOI：

  10.1016/j.ejmech.2010.01.031

文献信息

• Antibacterial Potential of Garlic-Derived Allicin and Its Cancellation by Sulfhydryl Compounds
  作者：Hiroyuki FUJISAWA、Kazuhiro WATANABE、Kaoru SUMA、Kana ORIGUCHI、Hiroshi MATSUFUJI、Taiichiro SEKI、Toyohiko ARIGA

  DOI：10.1271/bbb.90096

  日期：2009.9.23

  Allicin (allyl 2-propenethiosulfinate), an antibacterial principle of garlic, has drawn much attention, since it has potent antimicrobial activity against a range of microorganisms, including methicillin-resistant Staphylococcus aureus. There have been many reports on the antibacterial properties of allicin, but no quantitative comparison of antibacterial activities between freshly prepared garlic extract and clinically useful antibiotics has been performed. To verify the substantial antibacterial effect of aqueous garlic extract, we compared it with those of allicin and several clinically useful antibiotics using two representative bacteria commonly found in the human environment, Gram-positive S. aureus and Gram-negative Escherichia coli. The garlic extract had more potent anti-staphylococcal activity than an equal amount of allicin. In terms of antibiotic potency against Gram-positive and Gram-negative bacteria, authentic allicin had roughly 1–2% of the potency of streptomycin (vs.  S. aureus), 8% of that of vancomycin (vs.  S. aureus), and only 0.2% of that of colistin (vs.  E. coli). The antibacterial activity of allicin was completely abolished by cysteine, glutathione and coenzyme A, but not by non-SH-compounds. The oxygen in the structure (–S(=O)–S–) of allicin therefore functions to liberate the S-allyl moiety, which might be an offensive tool against bacteria.

  大蒜素（2-丙烯基硫代亚磺酸酯）是大蒜中的一种抗菌成分，因其对包括耐甲氧西林金黄色葡萄球菌在内的一众微生物具有强效的抗微生物活性而引起了广泛关注。虽然已有许多报道介绍了大蒜素的抗菌特性，但还没有实验进行过新制备的大蒜提取液和临床用抗生素之间抗菌活性的定量比较。为了证实水溶性大蒜提取液具有显著的抗菌效果，我们将其抗菌活性与大蒜素及数种临床可用抗生素进行了比较，采用的实验菌株为两种在人体环境中常见的细菌，即革兰氏阳性菌金黄色葡萄球菌和革兰氏阴性菌大肠杆菌。大蒜提取液对金黄色葡萄球菌的抗菌活性较相同量的大蒜素更强。就抗生素对革兰氏阳性和革兰氏阴性菌的抗菌效力而言，纯大蒜素大致具有链霉素（对金黄色葡萄球菌）1~2%的效力，万古霉素（对金黄色葡萄球菌）8%的效力，以及多粘菌素（对大肠杆菌）0.2%的效力。半胱氨酸、谷胱甘肽和辅酶A能够完全消除大蒜素的抗菌活性，而非巯基化合物则不能。因此大蒜素结构（-S(=O)-S-）中的氧具有释放S-丙烯基的作用，这可能是大蒜素对抗细菌的一种手段。
• Medicinal products incorporating bound organosulfur groups
  申请人：Ott M. David

  公开号：US20050260250A1

  公开（公告）日：2005-11-24

  Nutraceutical and dietary supplement formulations for delivering bioavailable thiols to a host, comprising certain organosulfur radicals, such as the allyl mercapto radical, bound to larger molecules such as proteins, resulting in the formation in the host's body of various allium -related compounds such as allicin. The formulations are produced by treating an ingestible material comprising a cysteine-containing protein with a thiol, disulfide, mixed disulfide, thiosufinate or mixed thiosulfinate so as to cause thiol residues to become disulfide bonded to cysteines contained in the protein.

  提供生物可利用的硫醇给宿主的营养保健品和膳食补充剂配方，包括某些有机硫自由基，例如烯丙基巯基自由基，与较大的分子（如蛋白质）结合，导致在宿主体内形成各种与葱属植物相关的化合物，如蒜素。这些配方通过用硫醇、二硫化物、混合二硫化物、硫酰基或混合硫酰基处理含半胱氨酸蛋白质的可摄入材料来制备，使硫醇残基与蛋白质中含有的半胱氨酸形成二硫键结合。
• Organosulphur prodrugs for the prevention and treatment of injectious diseases and pathologenic immune system response
  申请人：——

  公开号：US20040235946A1

  公开（公告）日：2004-11-25

  A method for enhancing the overall beneficial immune system response in a host that works in conjunction with the host's natural immune system response to simultaneously enhance the host's ability to eliminate infectious microbes while suppressing the toxicity of the immune system response to the host. The method utilizes the non-enzymatic formation of allicin in response to the localized generation of H2O2 by immune system cells (such as neutrophils) to simultaneously increase the antimicrobial effect while reducing the cytotoxicity to the host. It is shown that enzymes can be reversibly inhibited that would not normally be sensitive to deactivation by a thiol-disulfide exchange reaction. This results in part from the recognition that deactivation of SH dependant enzymes by allicin does not take place by the previously attributed mechanism of thiol-disulfide exchange reactions. Allicin, cysteine, and related organosulfur compounds have a variety of antimicrobial and immunomodulatory properties that work together with the host's immune system in the prevention and treatment of disease. Prophylactic and therapeutic treatment is provided by administering an allium-related organosulfur compound such that a localized thiosulfinate is caused to be non-enzymatically formed in response to localized generation of H2O2 by the activated immune system cells. Allicin, cysteine and related organosulfur compounds may be simultaneously delivered in an efficient manner through the use of protein-bound S-AllylMercaptoCysteine (SAMC) or similar prodrugs.

  一种增强宿主整体有益免疫系统反应的方法，与宿主自然免疫系统反应协同作用，同时增强宿主消除感染微生物的能力，同时抑制免疫系统反应对宿主的毒性。该方法利用免疫系统细胞（如中性粒细胞）产生的局部H2O2而非酶促形成大蒜素，以同时增加抗微生物作用，同时减少对宿主的细胞毒性。研究表明，可以可逆地抑制通常不敏感于巯基-二硫化物交换反应失活的酶。部分原因是因为认识到大蒜素对SH依赖的酶的失活不是通过先前归因于巯基-二硫化物交换反应的机制进行的。大蒜素、半胱氨酸和相关有机硫化合物具有各种抗微生物和免疫调节性质，与宿主的免疫系统一起在预防和治疗疾病方面发挥作用。通过给予与韭菜属植物相关的有机硫化合物，使局部硫代氧化物在被激活的免疫系统细胞产生的局部 的作用下非酶促形成，提供预防性和治疗性治疗。可以通过使用蛋白质结合的S-烯丙基巯基半胱氨酸（SAMC）或类似的前药同时有效地传递大蒜素、半胱氨酸和相关有机硫化合物。
• AGENT FOR PREVENTING, AMELIORATING, OR TREATING PERIODONTAL DISEASE
  申请人：Wakunaga Pharmaceutical Co., Ltd.

  公开号：EP3970793A1

  公开（公告）日：2022-03-23

  Provided is a medicine or food useful for preventing, ameliorating or treating periodontal disease. An agent for preventing, ameliorating or treating periodontal disease comprises one or more cysteine derivatives selected from the group consisting of S1PC, SAC and SAMC or a salt thereof as an active ingredient.

  本发明提供了一种用于预防、改善或治疗牙周病的药物或食品。一种用于预防、改善或治疗牙周病的制剂包含一种或多种选自 S1PC、SAC 和 SAMC 所组成的组的半胱氨酸衍生物或其盐作为活性成分。
• A Tissue Homogenate Method To Prepare Gram-Scale Allium Thiosulfinates and Their Disulfide Conjugates with Cysteine and Glutathione
  作者：Guodong Zhang、Kirk L. Parkin

  DOI：10.1021/jf4003818

  日期：2013.3.27

  The health benefits of Allium vegetables are widely attributed to the enzyme-derived organosulfur compounds called thiosulfinates (TS). However, the lack of a suitable method to prepare TS in good yields has hampered the evaluation of their biological activities. This paper describe a simple enzymatic method using Allium tissue homogenates as a reaction system to prepare gram-scale TS, including those enriched in 1-propenyl groups, which are particularly difficult to obtain. This method is simple, easy to scale up, and requires no column purification step, making it suitable for practical large-scale production of Allium TS. The prepared TS were further utilized to prepare the disulfide conjugates with cysteine and glutathione (CySSR and GSSR, R = methyl, ethyl, propyl, 1-propenyl, and allyl), which are the presumptive metabolites of TS. Among all of the Allium CySSR and GSSR conjugates, the newly prepared glutathione conjugate with 1-propenyl TS, GSSPe, showed the most potent effect to induce quinone reductase (QR, a representative phase II enzyme) in murine hepatoma cells (Hepa 1c1c7) and inhibit nitric oxide (NO) production in lipopolysaccharide (LPS)-stimulated macrophage cells (RAW 264.7).