(Z)-ajoene | 92285-00-2

• 分子结构分类: 有机化合物 - 有机硫化合物 - 亚砜
• 英文名称: (Z)-ajoene
• 英文别名: (Z)-1-allyl-2-(3-(allylsulfinyl)prop-1-en-1-yl)disulfane；(Z)-4,5,9-trithiadodeca-1,6,11-triene-9-oxide；Z-4,5,9-trithiadodeca-1,6,11-triene 9-oxide；Z-4,5,9-trithiadodeca-1,6,11-triene-9-oxide；4,5,9-trithiadodeca-1,6,11-triene-9-oxide；cis-ajoene；(Z)-1-(prop-2-enyldisulfanyl)-3-prop-2-enylsulfinylprop-1-ene
• CAS: 92285-00-2
• 化学式: C₉H₁₄OS₃
• 分子量: 234.408
• InChiKey: IXELFRRANAOWSF-ALCCZGGFSA-N

物化性质

• 沸点：
  376.0±42.0 °C(Predicted)
• 密度：
  1.181±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  86.9
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2930909090

反应信息

• 作为反应物：
  描述：

  (Z)-ajoene 在 还原型辅酶II(NADPH)四钠盐 、 glutathione reductase 作用下， 以 水 为溶剂， 生成 4,5,9-trithiadodeca-1,6,11-triene 、 4,8,9,13-tetrathiahexadeca-1,6,10,15-tetraene
  参考文献：
  名称：

  Ajoene Is an Inhibitor and Subversive Substrate of Human Glutathione Reductase and Trypanosoma cruzi Trypanothione Reductase:  Crystallographic, Kinetic, and Spectroscopic Studies

  摘要：

  Ajoene ((E,Z)-4,5,9-trithiadodeca-1,6,11-triene 9-oxide), a garlic-derived natural compound, is a covalent; inhibitor as well as a substrate of human glutathione reductase (GR) and Trypanosoma cruzi trypanothione reductase (TR). The 2.1-Angstrom resolution crystal structure of GR inhibited by (E)-ajoene revealed a mixed disulfide between the active site Cys58 and the CH2=CH-CH2-SO-CH2-CH=CH-S moiety of ajoene. The modified enzyme has a markedly increased oxidase activity when compared to free GR, GR reduces (Z)-ajoene with a k(cat)/K-m of 6.8 x 10(3) M-1 s(-1) yielding 4,5,9-trithiadodeca-1,6,11-triene (deoxyajoene) and 4,8,9,13-tetrathiahexadeca-1,6,10,15-tetraene as stable reaction products. The reaction leads also to the formation of single-electron reduced products and concomitantly superoxide anion radicals as shown by coupling the reaction to the reduction of cytochrome c. The interactions between the flavoenzymes and ajoene are expected to increase the oxidative stress of the respective cell. The antiparasitic and cytostatic actions of ajoene may at least in part be due to the multiple effects on key enzymes of the antioxidant thiol metabolism.

  DOI：

  10.1021/jm980471k
• 作为产物：
  描述：

  1-allyl-2-(3-(allylthio)prop-1-en-1-yl)disulfane 在 间氯过氧苯甲酸 作用下， 生成 (Z)-ajoene
  参考文献：
  名称：

  Ajoene, A Stable Garlic By-Product, Inhibits High Fat Diet-Induced Hepatic Steatosis and Oxidative Injury Through LKB1-Dependent AMPK Activation

  摘要：

  Hepatic steatosis, a hepatic component of metabolic syndrome, is common and may progress to steatohepatitis and cirrhosis. The liver X receptor-alpha (LXR alpha)-sterol regulatory element binding protein-1c (SREBP-1c) pathway plays a key role in hepatic steatosis. This study investigated the potential of ajoene, a stable garlic by-product, to inhibit high fat diet (HFD)-induced hepatic steatosis and the underlying mechanism. Ajoene treatment attenuated fat accumulation and induction of lipogenic genes in the liver of HFD-fed mice. Blood biochemical analyses and histopathologic examinations showed that ajoene prevented liver injury with the inhibition of oxidative stress, as evidenced by thiobarbituric acid reactive substances formation and nitrotyrosinylation. Moreover, ajoene treatment inhibited LXR alpha agonist (T0901317)-mediated SREBP-1c activation, and transactivation of the lipogenic target genes in hepatocytes. Ajoene was found to activate AMP-activated protein kinase (AMPK) via LKB1, responsible for the inhibition of p70 ribosomal S6 kinase-1 (S6K1). The ability of ajoene to repress T0901317-induced SREBP-1c expression was antagonized by inhibition of AMPK or activation of S6K1, supporting the role of these kinases in the antisteatotic effect. Our results demonstrate that ajoene has an effect of activating AMPK through LKB1 and inhibit S6K1 activity, contributing to the prevention of SREBP-1c-mediated hepatic lipogenesis via the inhibition of LXR alpha activity. Antioxid Redox Signal. 14, 187-202.

  DOI：

  10.1089/ars.2010.3190

文献信息

• [EN] PROCESS FOR THE MANUFACTURE OF AJOENE DERIVATIVES<br/>[FR] PROCÉDÉ DE PRÉPARATION DE DÉRIVÉS D'AJOÈNE
  申请人：UNIV DANMARKS TEKNISKE

  公开号：WO2012076016A1

  公开（公告）日：2012-06-14

  The present invention relates to the compound (E,Z)-ajoene of formula (1) for use in treatment of bacterial infections. Another aspect of the present invention is a composition comprising (E,Z)-ajoene of formula (1) and at least one antibiotic. Yet another aspect of the invention relates to a method for manufacturing (E,Z) ajoene of formula (1) wherein the conformation of the internal C=C- bond can be either E or Z or a mixture thereof, said method comprising reacting allicin of formula (3) with an acid in the presence of a solvent to provide (E,Z ajoene) of formula (1) as defined above. Yet another aspect of the invention is (E,Z)-ajoene of formula 1 obtainable by the method described above.

  本发明涉及化合物（E,Z）-蒜烯（式1）的用途，用于治疗细菌感染。本发明的另一个方面是包含（E,Z）-蒜烯（式1）和至少一种抗生素的组合物。本发明的另一个方面涉及一种制备（E,Z）蒜烯（式1）的方法，其中内部C=C键的构象可以是E或Z或二者的混合物，所述方法包括在溶剂存在下将大蒜素（式3）与酸反应，以提供上述定义的（E,Z蒜烯）（式1）。本发明的另一个方面是通过上述描述的方法获得的（E,Z）-蒜烯（式1）。
• The chemistry of alkyl thiosulfinate esters. 9. Antithrombotic organosulfur compounds from garlic: structural, mechanistic, and synthetic studies
  作者：Eric. Block、Saleem. Ahmad、James L. Catalfamo、Mahendra K. Jain、Rafael. Apitz-Castro

  DOI：10.1021/ja00282a033

  日期：1986.10

  Synthese de l'ajoene (oxyde-9 de trithia-4,5,9 dodecatriene-1,6,11) et de quelques analogues

  合成 de l'ajoene (oxyde-9 de trithia-4,5,9 dodecatriene-1,6,11) et de quelques 类似物
• Short Total Synthesis of Ajoene
  作者：Filipa Silva、Shaista S. Khokhar、Danielle M. Williams、Robert Saunders、Gareth J. S. Evans、Michael Graz、Thomas Wirth

  DOI：10.1002/anie.201808605

  日期：2018.9.17

  We describe a short total synthesis of ajoene, a major biologically active constituent of garlic. The instability of allicin as the only other known alternative starting material has led to the development of a reliable procedure for the synthesis of ajoene from simple building blocks that is also suitable for upscale operations.

  我们描述了大蒜主要生物活性成分阿霍烯的简短全合成。大蒜素作为唯一已知的替代起始材料的不稳定性导致开发出一种可靠的方法，用于从简单的结构单元合成阿霍烯，该方法也适用于高档操作。
• The chemistry of alkyl thiosulfate esters. 8. (E,Z)-Ajoene: a potent antithrombotic agent from garlic
  作者：Eric Block、Saleem Ahmad、Mahendra K. Jain、Roger W. Crecely、Rafael Apitz-Castro、Maria R. Cruz

  DOI：10.1021/ja00338a049

  日期：1984.12

  Synthese de l'ajoene([allyl propene-2sulfinyl-3propenyl] disulfure) a partir de l'allicine (propene-2 thiosulfinate de S-allyle), du diallyl trisulfure et de vinyl-2 dithianne-1,3. Ces 3 composes representent 75% de l'activite anticoagulante de l'extrait d'ail

  合成这些 de l'ajoene([allyl propene-2sulfinyl-3propenyl] disulfure) a partir de l'allicine (propene-2 thiosulfinate de S-allyle), du diallyl trisulfure et devinyl-2 dithianne-1,3。Ces 3 组成代表 75% de l'activite anticoagulante de l'extrait d'ail
• NOVEL ORGANIC SULFUR COMPOUND, METHOD FOR PREPARING SAME, AND PHARMACEUTICAL COMPOSITION FOR PREVENTING OR TREATING CANCER OR AN INFLAMMATORY DISEASE, CONTAINING SAME AS ACTIVE INGREDIENT
  申请人：SOOKMYUNG WOMENS UNIVERSITY INDUSTRY-ACADEMIC COOPERATION FOUNDATION

  公开号：US20210300865A1

  公开（公告）日：2021-09-30

  A novel organic sulfur compound, a method for preparing the same, and a pharmaceutical composition for preventing or treating cancer or inflammatory diseases, containing the same as an active ingredient are provided. The novel organic sulfur compound is capable of excellently inhibiting histone deacetylated (HDAC) enzymes in a concentration of nanomolar or micromolar units and has been found to have an excellent effect against inflammatory diseases, and has been found to be capable of inhibiting the proliferation of cancer.

  提供一种新型有机硫化合物，一种制备该化合物的方法，以及一种包含该化合物作为活性成分的用于预防或治疗癌症或炎症性疾病的药物组合物。这种新型有机硫化合物能够在纳摩尔或微摩尔单位的浓度下出色地抑制组蛋白去乙酰化酶（HDAC），已发现对炎症性疾病具有出色的作用，并且已发现能够抑制癌症的增殖。