大蒜烯丙基硫化物的分离鉴定及抗氧化性
为了研究大蒜烯丙基硫化物的抗氧化活性,该文利用离子交换层析与制备液相技术从大蒜中分离得到S-烯丙基-L-半胱氨酸（S-allyl-L-cysteine,SAC）、S-烯丙基-L-半胱氨酸亚砜（S-allyl-L-cysteine sulfoxide,ACSO）和γ-谷氨酰-S-烯丙基-L-半胱氨酸（γ-L-glutamyl-S-allyl-L-cysteine,GSAC）3种水溶性烯丙基硫化物。分离产物利用高效液相色谱-电喷雾离子化串联质谱联用（high performance liquid chromatography-electrospray ionization-mass/mass sp...
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| Published in | 农业工程学报 Vol. 31; no. 12; pp. 268 - 274 |
|---|---|
| Main Author | |
| Format | Journal Article |
| Language | Chinese |
| Published |
沈阳农业大学食品学院,沈阳,110866%沈阳师范大学美术与设计学院,沈阳,110034
2015
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| Subjects | |
| Online Access | Get full text |
| ISSN | 1002-6819 |
| DOI | 10.11975/j.issn.1002-6819.2015.12.036 |
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| Abstract | 为了研究大蒜烯丙基硫化物的抗氧化活性,该文利用离子交换层析与制备液相技术从大蒜中分离得到S-烯丙基-L-半胱氨酸（S-allyl-L-cysteine,SAC）、S-烯丙基-L-半胱氨酸亚砜（S-allyl-L-cysteine sulfoxide,ACSO）和γ-谷氨酰-S-烯丙基-L-半胱氨酸（γ-L-glutamyl-S-allyl-L-cysteine,GSAC）3种水溶性烯丙基硫化物。分离产物利用高效液相色谱-电喷雾离子化串联质谱联用（high performance liquid chromatography-electrospray ionization-mass/mass spectrometry,HPLC-ESI-MS/MS）、核磁共振氢谱（proton nuclear magnetic resonance,1H NMR）和核磁共振碳谱（carbon-13 nuclear magnetic resonance,13C NMR）技术及比旋光度检测方法鉴定,并与合成标准品比对分析确定。同时,该文以具有半胱氨酸结构的还原型谷胱甘肽（glutathione,GSH）为参照测定了SAC、ACSO、GSAC的1,1-二苯基-2-三硝基苯肼（1,1-diphenyl-2-picrylhydrazyl,DPPH）自由基清除能力及铁离子螯合能力。结果表明,SAC和GSAC对DPPH自由基的清除率较高（73.55%,72.68%）且与GSH（71.14%）无显著性差异（P〈0.05）;SAC和ACSO对铁离子的螯合率较高（81.21%,79.18%）且与GSH（78.13%）无显著性差异（P〈0.05）,尤其是GSAC对铁离子螯合率（92.76%）显著性高于GSH（P〈0.05）,证实了3种硫化物均具有很好的抗氧化性能。研究结果进一步解释和阐述大蒜硫化物的螯合能力,进而为大蒜硫化物以抗氧化为基础的其他功能活性研究提供参考。 |
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| AbstractList | 为了研究大蒜烯丙基硫化物的抗氧化活性,该文利用离子交换层析与制备液相技术从大蒜中分离得到S-烯丙基-L-半胱氨酸（S-allyl-L-cysteine,SAC）、S-烯丙基-L-半胱氨酸亚砜（S-allyl-L-cysteine sulfoxide,ACSO）和γ-谷氨酰-S-烯丙基-L-半胱氨酸（γ-L-glutamyl-S-allyl-L-cysteine,GSAC）3种水溶性烯丙基硫化物。分离产物利用高效液相色谱-电喷雾离子化串联质谱联用（high performance liquid chromatography-electrospray ionization-mass/mass spectrometry,HPLC-ESI-MS/MS）、核磁共振氢谱（proton nuclear magnetic resonance,1H NMR）和核磁共振碳谱（carbon-13 nuclear magnetic resonance,13C NMR）技术及比旋光度检测方法鉴定,并与合成标准品比对分析确定。同时,该文以具有半胱氨酸结构的还原型谷胱甘肽（glutathione,GSH）为参照测定了SAC、ACSO、GSAC的1,1-二苯基-2-三硝基苯肼（1,1-diphenyl-2-picrylhydrazyl,DPPH）自由基清除能力及铁离子螯合能力。结果表明,SAC和GSAC对DPPH自由基的清除率较高（73.55%,72.68%）且与GSH（71.14%）无显著性差异（P〈0.05）;SAC和ACSO对铁离子的螯合率较高（81.21%,79.18%）且与GSH（78.13%）无显著性差异（P〈0.05）,尤其是GSAC对铁离子螯合率（92.76%）显著性高于GSH（P〈0.05）,证实了3种硫化物均具有很好的抗氧化性能。研究结果进一步解释和阐述大蒜硫化物的螯合能力,进而为大蒜硫化物以抗氧化为基础的其他功能活性研究提供参考。 TS201.2; 为了研究大蒜烯丙基硫化物的抗氧化活性，该文利用离子交换层析与制备液相技术从大蒜中分离得到 S-烯丙基-L-半胱氨酸（S-allyl-L-cysteine，SAC）、S-烯丙基-L-半胱氨酸亚砜（S-allyl-L-cysteine sulfoxide，ACSO）和γ-谷氨酰-S-烯丙基-L-半胱氨酸（γ-L-glutamyl-S-allyl-L-cysteine，GSAC）3种水溶性烯丙基硫化物。分离产物利用高效液相色谱-电喷雾离子化串联质谱联用（high performance liquid chromatography-electrospray ionization-mass/mass spectrometry， HPLC-ESI-MS/MS）、核磁共振氢谱（proton nuclear magnetic resonance，1H NMR）和核磁共振碳谱（carbon-13 nuclear magnetic resonance，13C NMR）技术及比旋光度检测方法鉴定，并与合成标准品比对分析确定。同时，该文以具有半胱氨酸结构的还原型谷胱甘肽（glutathione，GSH）为参照测定了 SAC、ACSO、GSAC 的1,1-二苯基-2-三硝基苯肼（1,1-diphenyl-2-picrylhydrazyl，DPPH）自由基清除能力及铁离子螯合能力。结果表明，SAC和GSAC对DPPH自由基的清除率较高（73.55%，72.68%）且与 GSH（71.14%）无显著性差异（P<0.05）；SAC 和 ACSO 对铁离子的螯合率较高（81.21%，79.18%）且与GSH（78.13%）无显著性差异（P<0.05），尤其是GSAC对铁离子螯合率（92.76%）显著性高于GSH（P<0.05），证实了3种硫化物均具有很好的抗氧化性能。研究结果进一步解释和阐述大蒜硫化物的螯合能力，进而为大蒜硫化物以抗氧化为基础的其他功能活性研究提供参考。 |
| Abstract_FL | The allyl-substituted cysteine derivatives were major components of sulfur compounds in garlic. This study separated and identified 3 allyl-substituted cysteine derivatives, i.e.S-allyl-L-cysteine (SAC),S-allyl-L-cysteine sulfoxide (ACSO) andγ-L-glutamyl-S-allyl-L-cysteine (GSAC). Furthermore, scavenging ability of 1,1-Diphenyl-2-picrylhydrazyl (DPPH) free radical and iron chelating ability were tested through comparing the compounds of SAC, ACSO and GSAC with glutathione (GSH) to evaluate the antioxidation. SAC, ACSO and GSAC were isolated from garlic bulbs using ion-exchange chromatography and pre-HPLC (high performance liquid chromatography). Their molecular structures were identified by high performance liquid chromatography-electrospray ionization-mass/mass spectrometry (HPLC-ESI-MS/MS), proton nuclear magnetic resonance (1H NMR), carbon-13 nuclear magnetic resonance (13C NMR) and specific rotatory power. SAC and ACSO which yielded the expected [M+H]+ of m/z 162.1 and 177.8 by the measurement of mass spectrometry under positive ion mode were conferred asS-allyl-L-cysteine (C6H11O2NS) andS-allyl-L-cysteine sulfoxide (C6H11O3NS) respectively compared with the data of corresponding standard. GSAC, showing the corresponding [M-H]- of m/z 288.8, was identified asγ-glutamyl-S-allyl-L-cysteine (C11H18O5N2S) by HPLC-MS. The1H NMR spectrum of SAC and ACSOindicated the presence of the cysteinyl (δ 2.96 and 3.83, 3H) and (δ 3.26 and 4.13, 3H) moieties. The13C NMR spectrum of compound SAC and ACSO showed the presence of the cysteinyl carboxyl (δ 175.6 andδ 188.0) carbons. Similarly, the1H NMR spectrum of GSAC indicated the presence of the glutamyl (δ 2.32-2.43, 2.66 and 3.46, 5H) and cysteinyl (δ 2.75 and 4.76, 3H) moieties. The13C NMR spectrum of GSACrevealed the presence of 11 magnetically nonequivalent carbon atoms, with three of them being the glutamyl carboxyl, glutamyl carbonyl and cysteinyl carboxyl (δ 182.5, 183.2 and 184.4) carbons. Meanwhile, the scavenging activity of DPPH free radical and the chelating activity of iron ion by allyl-substituted sulfides (SAC, ACSO and GSAC) were determined with reference to cysteine derivative of GSH. The scavenging activity of DPPH free radical had no significant difference between GSH (71.14%) and both of SAC (73.55%) andGSAC (72.68%). Iron ion is one of the main oxidizing auxiliaries which can initiate free radical in vitro and vivo, therefore, chelating with iron ion can remove the oxidizing auxiliaries effectively, and prevent the formation of free radicals. Likewise, no significant differences between GSH (81.21%) and both of SAC (79.18%) and ACSO (78.13%) were observed for the chelating activity of iron ion tested in this study. In particular, the chelating activity of iron ion of GSAC (92.76%) was greater than GSH. These results confirmed the antioxidant activity of these allyl-substituted cysteine derivatives. Garlic planting area in China accounted for a third of the world. At harvest time, garlic waste dumping in the field led to the waste of resource and the pollution of the environment, and these waste parts of garlic were also the sources of sulfur compounds. The processing in this experiment could make full use of garlic (edible part and non-edible part), and the study could provide some theoretical guidance for the industrialization of large-scale extraction of sulfur-containing products, and improve the level of deep processing of garlic. The work revealed the first evidence of antioxidant activity of GSAC, which could be involved in its chelating activity of iron ion. |
| Author | 刘玲 陈琭璐 张瑶 白冰 纪淑娟 |
| AuthorAffiliation | 沈阳农业大学食品学院,沈阳110866 沈阳师范大学美术与设计学院,沈阳110034 |
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| Author_FL | Chen Lulu Liu Ling Zhang Yao Ji Shujuan Bai Bing |
| Author_FL_xml | – sequence: 1 fullname: Liu Ling – sequence: 2 fullname: Chen Lulu – sequence: 3 fullname: Zhang Yao – sequence: 4 fullname: Bai Bing – sequence: 5 fullname: Ji Shujuan |
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| DOI | 10.11975/j.issn.1002-6819.2015.12.036 |
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| DocumentTitleAlternate | Isolation determination of garlic allyl sulfides and their antioxidant activity |
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| Keywords | S-烯丙基-L-半胱氨酸亚砜 γ-L-glutamyl-S-allyl-L-cysteine 螯合 S-allyl-L-cysteine antioxidant activity 抗氧化性 identification 鉴定 separation γ-谷氨酰-S-烯丙基-L-半胱氨酸 chelation S-allyl-L-cysteine sulfoxide S-烯丙基-L-半胱氨酸 分离 |
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| Notes | 11-2047/S Liu Ling, Chen Lulu, Zhang Yao, Bai Bing,Ji Shujuan （1. College of Food, Shenyang Agricultural University, Shenyang 110866, China; 2. College of Art and Design, Shenyang Normal University, Shenyang 110034, China） separation; identification; chelation; S-allyl-L-cysteine; S-allyl-L-cysteine sulfoxide; γ-L-glutamyl-S-allyl-L-cysteine; antioxidant activity The allyl-substituted cysteine derivatives were major components of sulfur compounds in garlic.This study separated and identified 3 allyl-substituted cysteine derivatives,i.e.S-allyl-L-cysteine（SAC）,S-allyl-L-cysteine sulfoxide（ACSO） and γ-L-glutamyl-S-allyl-L-cysteine（GSAC）.Furthermore,scavenging ability of 1,1-Diphenyl-2-picrylhydrazyl（DPPH） free radical and iron chelating ability were tested through comparing the compounds of SAC,ACSO and GSAC with glutathione（GSH） to evaluate the antioxidation.SAC,ACSO and GSAC were isolated from garlic bulbs using ion-exchange chromatography and pre-HPLC（high performance liquid chromatography）.Their molecular stru |
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| Publisher | 沈阳农业大学食品学院,沈阳,110866%沈阳师范大学美术与设计学院,沈阳,110034 |
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| Snippet | 为了研究大蒜烯丙基硫化物的抗氧化活性,该文利用离子交换层析与制备液相技术从大蒜中分离得到S-烯丙基-L-半胱氨酸（S-allyl-L-cysteine,SAC）、S-烯丙基-L-半胱氨酸亚砜（S-allyl-L-cysteine... TS201.2; 为了研究大蒜烯丙基硫化物的抗氧化活性，该文利用离子交换层析与制备液相技术从大蒜中分离得到 S-烯丙基-L-半胱氨酸（S-allyl-L-cysteine，SAC）、S-烯丙基-L-半胱氨酸亚砜（S-allyl-L-cysteine... |
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| SubjectTerms | S-烯丙基-L-半胱氨酸 S-烯丙基-L-半胱氨酸亚砜 γ-谷氨酰-S-烯丙基-L-半胱氨酸 分离 抗氧化性 螯合 鉴定 |
| Title | 大蒜烯丙基硫化物的分离鉴定及抗氧化性 |
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