[6]-dehydroshogaol

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: [6]-dehydroshogaol
• 英文别名: 1-(4-Hydroxy-3-methoxyphenyl)deca-1,4-dien-3-one；1-(4-hydroxy-3-methoxyphenyl)deca-1,4-dien-3-one
• 化学式: C₁₇H₂₂O₃
• 分子量: 274.36
• InChiKey: JLXKTAQNHHXFHL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  谷胱甘肽 、 [6]-dehydroshogaol 在 三乙胺 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 6-dehydroshogaol glutathione conjugate
  参考文献：
  名称：

  Glutathione conjugation attenuates biological activities of 6-dehydroshogaol from ginger

  摘要：

  6-Dehydroshogaol (6-DHSG) is a bioactive alpha,beta-unsaturated carbonyl compound isolated from fresh ginger with anti-inflammatory and phase II enzyme inducing activities. Here we describe the glutathione (GSH)-dependent metabolism and the effect of this metabolic transformation on the biological activities of 6-DHSG. Compared with other ginger compounds, such as 6-gingerol and 6-shogaol, 6-DHSG showed the most potent anti-inflammatory effect in lipopolysaccharide (LPS)-stimulated RAW 264.7 cells. The biological activities of 6-DHSG were attenuated by sulfhydryl antioxidants such as glutathione (GSH) or N-acetyl cysteine (NAC), but not ascorbic acid (ASC). 6-DHSG was metabolised by GSH to form a GSH conjugate (GS-6-DHSG) in RAW 264.7 cells, via a potential mechanism involving the catalytic activity of glutathione-S-transferase (GST). GS-6-DHSG showed reduced biological activities compared with 6-DHSG in multiple biological assays. Together, these results indicate that GSH conjugation attenuates the biological activities of 6-DHSG and other alpha,beta-unsaturated carbonyl compounds. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.foodchem.2013.02.073

文献信息

• GINGER METABOLITES AND USES THEREOF
  申请人：North Carolina A&T State University

  公开号：US20160235697A1

  公开（公告）日：2016-08-18

  The present application generally relates to the use of metabolites of ginger and analogs thereof for the treatment and prevention of diseases, including but not limited to, cancer.

  本申请一般涉及使用生姜代谢物及其类似物治疗和预防疾病，包括但不限于癌症。
• 6-shogaol derivatives and activities thereof
  申请人：North Carolina Agricultural and Technical State University

  公开号：US10342766B2

  公开（公告）日：2019-07-09

  Derivatives of 6-shogaol are described herein. Also described herein are methods of preparing the derivatives, as well as methods of using the derivatives to activate Nrf2 and to treat diseases associated with inflammation and/or oxidative stress.

  本文描述了 6-肖高醇的衍生物。本文还描述了制备这些衍生物的方法，以及使用这些衍生物激活 Nrf2 和治疗与炎症和/或氧化应激相关疾病的方法。
• US9272994B1
  申请人：——

  公开号：US9272994B1

  公开（公告）日：2016-03-01
• US9549911B2
  申请人：——

  公开号：US9549911B2

  公开（公告）日：2017-01-24
• Glutathione conjugation attenuates biological activities of 6-dehydroshogaol from ginger
  作者：Guodong Zhang、Viriya Nitteranon、Lok Yan Chan、Kirk L. Parkin

  DOI：10.1016/j.foodchem.2013.02.073

  日期：2013.9

  6-Dehydroshogaol (6-DHSG) is a bioactive alpha,beta-unsaturated carbonyl compound isolated from fresh ginger with anti-inflammatory and phase II enzyme inducing activities. Here we describe the glutathione (GSH)-dependent metabolism and the effect of this metabolic transformation on the biological activities of 6-DHSG. Compared with other ginger compounds, such as 6-gingerol and 6-shogaol, 6-DHSG showed the most potent anti-inflammatory effect in lipopolysaccharide (LPS)-stimulated RAW 264.7 cells. The biological activities of 6-DHSG were attenuated by sulfhydryl antioxidants such as glutathione (GSH) or N-acetyl cysteine (NAC), but not ascorbic acid (ASC). 6-DHSG was metabolised by GSH to form a GSH conjugate (GS-6-DHSG) in RAW 264.7 cells, via a potential mechanism involving the catalytic activity of glutathione-S-transferase (GST). GS-6-DHSG showed reduced biological activities compared with 6-DHSG in multiple biological assays. Together, these results indicate that GSH conjugation attenuates the biological activities of 6-DHSG and other alpha,beta-unsaturated carbonyl compounds. (C) 2013 Elsevier Ltd. All rights reserved.