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海藻MGMG型甘油糖脂的研究
引用本文:王梦雪,蒋盈,詹娜,何美佳,刘红兵. 海藻MGMG型甘油糖脂的研究[J]. 中草药, 2017, 48(21): 4398-4402
作者姓名:王梦雪  蒋盈  詹娜  何美佳  刘红兵
作者单位:中国海洋大学医药学院, 青岛海洋科学与技术国家实验室海洋药物与生物制品功能实验室, 山东 青岛 266003,中国海洋大学医药学院, 青岛海洋科学与技术国家实验室海洋药物与生物制品功能实验室, 山东 青岛 266003,中国海洋大学医药学院, 青岛海洋科学与技术国家实验室海洋药物与生物制品功能实验室, 山东 青岛 266003,中国海洋大学医药学院, 青岛海洋科学与技术国家实验室海洋药物与生物制品功能实验室, 山东 青岛 266003,中国海洋大学医药学院, 青岛海洋科学与技术国家实验室海洋药物与生物制品功能实验室, 山东 青岛 266003
基金项目:国家自然科学基金资助项目(31271845);青岛海洋科学与技术国家实验室鳌山科技创新计划项目(2015ASKJ02)
摘    要:目的鉴定中药海藻(羊栖菜Sargassum fusiforme)中的单半乳糖基单酰基甘油酯(monogalactosylmonoacylglycerol,MGMG),分析sn-1型和sn-2型位置异构体的化学特征。方法利用多种色谱手段分离得到MGMG,采用NMR、HR-ESI-MS等谱学方法鉴定结构,采用HPLC、HPLC-ESI-MS/MS分析位置异构体的互变及其色谱-质谱特征。结果分离到并鉴定5个MGMG,酰基分别为十八碳四烯酰基、十八碳三烯酰基、二十碳四烯酰基、十八碳二烯酰基和十八碳单烯酰基;sn-1型和sn-2型MGMG单体均不稳定,会相互迅速转变直至sn-1型为主(相对峰面积85∶15)的平衡状态。sn-2型在反相色谱柱上的保留时间较sn-1型小,先被洗脱;两者二级质谱碎片离子丰度有较大差异,以[M+Na-Gal]~+为基峰(100%),sn-2型的[M+Na-RCOOH]~+丰度50%,sn-1型的[M+Na-RCOOH]~+丰度20%。结论首次从褐藻门中分离鉴定上述5个MGMG,阐明了sn-1型和sn-2型MGMG之间的互变过程,首次报道这2种位置异构体的色谱-质谱特征,可用于MGMG类化合物酰基取代位置的鉴定。

关 键 词:海藻  羊栖菜  单半乳糖基单酰基甘油酯  甘油糖脂  结构鉴定  位置异构
收稿时间:2017-05-10

Study on monogalactosylmonoacylglycerol in marine algae (Sargassum fusiforme)
WANG Meng-xue,JIANG Ying,ZHAN N,HE Mei-jia and LIU Hong-bing. Study on monogalactosylmonoacylglycerol in marine algae (Sargassum fusiforme)[J]. Chinese Traditional and Herbal Drugs, 2017, 48(21): 4398-4402
Authors:WANG Meng-xue  JIANG Ying  ZHAN N  HE Mei-jia  LIU Hong-bing
Affiliation:Laboratory for Marine Drugs and Bioproducts of Qingdao, National Laboratory for Marine Science and Technology, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China,Laboratory for Marine Drugs and Bioproducts of Qingdao, National Laboratory for Marine Science and Technology, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China,Laboratory for Marine Drugs and Bioproducts of Qingdao, National Laboratory for Marine Science and Technology, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China,Laboratory for Marine Drugs and Bioproducts of Qingdao, National Laboratory for Marine Science and Technology, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China and Laboratory for Marine Drugs and Bioproducts of Qingdao, National Laboratory for Marine Science and Technology, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China
Abstract:Objective To indentify monogalactosylmonoacylglycerol (MGMG) and analyze the chemical characteristics of sn-1 and sn-2 type isomers in Marine TCM Sargassum fusiforme. Methods The MGMG compounds were isolated by multiple chromatography methods and their structures were determined by spectroscopic methods such as NMR and HRESI-MS. The interconversion and chromatography-mass spectrometry feature of MGMG positional isomers were analyzed through HPLC and HPLC-ESI-MS/MS. Results Five MGMGs were isolated from Sargassum fusiforme, and the fatty acyl compositions were stearidonoyl, linolenoyl, arachidoyl, linoleyl, and oleyl. The sn-1 and sn-2 type of MGMG were unstable. The interconversion tended to be sn-1 type rapidly, and kept balanced content at 85:15. The relative retention time of sn-2 type was less than sn-1 type on C18 reverse phase chromatography. The abundant fragment ions of MS/MS were significantly differences. The base peak was[M+Na-Gal]+ (100%), and the peak intensity of[M+Na-RCOOH]+ was always more than 50% from sn-2 type while less than 20% from sn-1 type. Conclusion Five MGMGs were isolated from brown algae for the first time. This was the first report about the interconversion and chromatography-mass spectrometry feature of sn-1 and sn-2 type. It can use to determine the fatty acyl attachment in each MGMG.
Keywords:marine algae  Sargassum fusiforme(Harvey.) Setchell  monogalactosylmonoacylglycerol (MGMG)  glyceroglycolipid  structure identification  positional isomers
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