Structure-activity relationship of antioxidative components isolated from ginger (Zingiber officinal)

姜（Zingiber officinal）中分离的抗氧化成分的构效关系

• 批准号: 10660133
• 负责人: KIKUZAKI Hiroe
• 金额: $ 1.98万
• 依托单位: Osaka City University
• 依托单位国家: 日本
• 项目类别: Grant-in-Aid for Scientific Research (C)
• 财政年份: 1998
• 资助国家: 日本
• 起止时间: 1998 至 1999
• 项目状态: 已结题
• 来源: https://kaken.nii.ac.jp/grant/KAKENHI-PROJECT-10660133/
• 关键词: ginger; gingerol; shogaol; dehydrogingerdione; ferulic acid related compounds; radical scavenging activity; antioxidant activity; ジンゲロール関連化合物

Eleven gingerol related compounds, gingerols, shogaols and dehydrogingerdiones substituted with an alkyl group bearing 8〜12 carbon chain length, were isolated from rhizomes of ginger (Zingiber officinale) using repeated chromatographic techniques. The antioxidant activities of these compounds were evaluated by five measurements ; 1) the DPPH radical scavenging activity, 2) the inhibitory effect on autoxidation of linoleic acid in ehtanol-buffer system, 3) the inhibitory effect on autoxidation of methyl linoleate, 4) the inhibitory effect on oxidation of methyl linoleate under aeration and heating using Oil Stability Index method and 5) the inhibitory effect on oxidation of liposome. The antioxidant activity of these constituents based on the methods 1 and 5 was in the order shogaols 【similar or equal】 gingerols > dehydrogingerdiones. The inhibitory effect on autoxidation of linoleic acid was in the order shogaols > gingerols > dehydrogingerdiones, while the activity of the compounds based on methods 3 and 4 was in the order dehydrogingerdiones > gingerols 【similar or equal】 shogaols. Concerning ginerol related compounds with different lengths of alkyl chain, significant higher activity was correlated with longer alkyl chains based on the method 2. This finding was also observed in the case of alkyl ferulates with different lengths of alkyl chain. In addition, the effects of cinnamic acid related compounds were measured using the methods 1-4. Caffeic acid with 3,4-dihydroxy phenyl group showed the strongest activity based on the methods 1, 3 and 4, while felulic acid with 4-hydroxy-3-methoxyphenyl group showed the strongest activity based on the method 2. These findings suggested that not only radical scavenging ability of antioxidant but also the affinity of the antioxidant with substrate owing to the substituents on the alkyl chain might contribute to the antioxidant activity.

采用重复色谱技术从姜（Zingiber officinale）根茎中分离出 11 种姜辣素相关化合物，即姜辣素、姜烯酚和被碳链长度为 8〜12 的烷基取代的脱氢姜二酮。通过五次测量评估这些化合物的抗氧化活性； 1）DPPH自由基清除活性，2）乙醇缓冲体系中对亚油酸自氧化的抑制作用，3）对亚油酸甲酯自氧化的抑制作用，4）使用油稳定性指数法对通气和加热下亚油酸甲酯氧化的抑制作用，5）对脂质体氧化的抑制作用。根据方法1和5，这些成分的抗氧化活性顺序为姜烯酚【相似或相等】姜辣素>脱氢姜二酮。对亚油酸自氧化的抑制作用顺序为姜烯酚>姜酚>去氢姜二酮，而方法3和4的化合物活性为去氢姜二酮>姜辣素【相似或相等】姜烯酚。对于具有不同烷基链长度的金花醇相关化合物，根据方法2，显着较高的活性与较长的烷基链相关。在具有不同烷基链长度的烷基阿魏酸的情况下也观察到这一发现。另外，使用方法1-4测量肉桂酸相关化合物的效果。根据方法1、3和4，具有3,4-二羟基苯基的咖啡酸显示出最强的活性，而根据方法2，具有4-羟基-3-甲氧基苯基的阿魏酸显示出最强的活性。这些结果表明，不仅抗氧化剂的自由基清除能力，而且由于抗氧化剂上的取代基而影响了抗氧化剂与底物的亲和力。 烷基链可能有助于抗氧化活性。