Analysis, distribution and function of unnatural glycerophospholipids in marine organisms

海洋生物中非天然甘油磷脂的分析、分布和功能

• 批准号: 13460088
• 负责人: ITABASHI Yutaka
• 金额: $ 8万
• 依托单位: Hokkaido University
• 依托单位国家: 日本
• 项目类别: Grant-in-Aid for Scientific Research (B)
• 财政年份: 2001
• 资助国家: 日本
• 起止时间: 2001 至 2003
• 项目状态: 已结题
• 来源: https://kaken.nii.ac.jp/en/grant/KAKENHI-PROJECT-13460088/
• 关键词: unnatural phospholipids; glycoglycerolipids; phosphatidylglycerol; reverse isomer; diastereomer; chiral phase HPLC; bacteia; environmental adaptation; 高温性細菌; 大腸菌; 化学分類; ビスモノアシルウリセロリン酸; 脂肪酸; 光学異性体

The aim of this study was to clarify the distribution and physiological function of unusual glycerophospho- and glycolipids in marine organisms. For this purpose, chiral phase HPLC, reversed-phase HPLC and reversed-phase HPLC in conjunction with electrospray ionization mass spectrometry(ESI-MS) were applied to the separation and identification of stereoisomeric and regio-isomeric glycerolipids. Using these techniques, we found an unnatural phosphatidylglycerol (1,2-diacyl-sn-glycero-3-phospho-3'-sn-glycerol, R, R configurations at the two chiral centers) from various kinds of microorganisms including marine bacteria. The R, R isomer content increased with increasing culture temperature. The results strongly suggest that the bacteria adapt to temperature by alternating not only the degree of unsaturation but also the stereoisomer composition of phosphatidylglycerols. In the present study, we also investigated the separation and identification of the reverse isomers of glycerophospholipi … More ds (PtdCho,PtdEtn,PtdIno) and glycoglycerolipids (MGDG,DGDG,SQDG) by reversed-phase HPLC/ESI-MS. These glycerolipids were chromatographed as intact forms or 3,5-dinitrophenylurethanes of the 1,2-diacyl-sn-glycerols derived from the parent molecules. Excellent resolution was achieved for reverse isomers of very different pairs of acyl groups, such as 20:5-16:0 and 22:6-16:0, on highly efficient C18 columns. Using the method, we analyzed the glycerolipids from some fish and marine algae, and found that only MGDG from marine red algae, such as Porphyra yezoensis and Gracilaria verrucosa, gave two clearly resolved peaks, representing the reverse isomers of 20:5(sn-1)/16:0(sn-2) and 16:0(sn-1)/20:5(sn-2), and 20:4(sn-1)/16:0(sn-2) and 16:0(sn-1)/20:5(sn-2), respectively. The present method provides the first direct demonstration of the occurrence of reverse isomers in natural glycoglycerolipids and should be helpful in promoting work on the biosynthetic pathway and physiological importance of the reverse isomers in the red algae. Less

本研究的目的是阐明海洋生物中不寻常的甘油磷酸脂和糖脂的分布和生理功能。为此，手性相高效液相色谱法，反相高效液相色谱法和反相高效液相色谱与电喷雾电离质谱（ESI-MS）相结合，应用于分离和鉴定的立体异构体和区域异构体的甘油脂。利用这些技术，我们从包括海洋细菌在内的各种微生物中发现了一种非天然的磷脂酰甘油（1，2-二酰基-sn-甘油-3-磷酸-3 '-sn-甘油，两个手性中心的R，R构型）。随着培养温度的升高，R，R异构体含量增加。结果强烈表明，细菌适应温度交替不仅不饱和度，但也磷脂酰甘油的立体异构体组成。在本研究中，我们还研究了甘油磷脂的反异构体的分离和鉴定 ...更多信息 ds（PtdCho，PtdEtn，PtdIno）和糖基甘油脂（MGDG，DGDG，SQDG）。这些甘油脂以完整形式或衍生自母体分子的1，2-二酰基-sn-甘油的3，5-二硝基苯氨基甲酸乙酯形式进行色谱分离。在高效C18色谱柱上，对不同酰基对的反相异构体（如20：5-16：0和22：6-16：0）实现了良好的分离。用该方法分析了几种鱼类和海藻中的甘油脂，发现只有条斑紫菜和江蓠中的MGDG有两个清晰的峰，分别为20：5（sn-1）/16：0（sn-2）和16：0（sn-1）/20：5（sn-2），以及20：4（sn-1）/16：0（sn-2）和16：0（sn-1）/20：5（sn-2）。本方法提供了第一个直接的演示发生在天然glycoglycerolipids的反异构体，并应有助于促进工作的生物合成途径和生理重要性的反异构体在红藻。少

项目成果

Chiral phase HPLC of glycerolipids

甘油脂的手性相 HPLC

• 发表时间: 2005
• 期刊: HPLC of Acyl Lipids(edited by J.-T.Lin, T.A.McKeon)(HNB Publishing, New York) Chapter 7
• 作者: Y.Taoka;Y.Itabashi;堀井豊充;Y.Itabashi
• 通讯作者: Y.Itabashi

Effect of temperature of the stereoselectivity of phospholipase D toward glycerol in the transphosphatidylation of phosphatidylcholine to phosphatidylglycerol

磷脂酰胆碱转磷脂酰化为磷脂酰甘油过程中温度对磷脂酶 D 对甘油立体选择性的影响

• 发表时间: 2004
• 期刊: LIPIDS 39・10
• 作者: R.Sato;Y.Itabashi;A.Suzuki;T.Hatanaka;A.Kuksis
• 通讯作者: A.Kuksis

忠海聡子, 遠藤 忍, 赤川博人, 板橋 豊: "間接紫外検出キャピラリー電気泳動法による脂肪酸の組成分析"分析化学. 52・9. 847-850 (2003)

Satoko Tadami、Shinobu Endo、Hiroto Akakawa、Yutaka Itabashi：“通过间接紫外检测毛细管电泳进行脂肪酸的组成分析” 分析化学 847-850（2003）。

板橋 豊 (共著): "改訂四版 油脂化学便覧 -脂質・界面活性剤-(日本油化学協会編)"丸善. 704 (2002)

Yutaka Itabashi（共同作者）：“修订版第四版油脂化学手册 - 脂质和表面活性剂 -（日本油脂化学家协会编辑）” Maruzen 704 (2002)。

Resolution of triacylglycerol positional isomers by reversed-phase high-performance liquid chromatography

• DOI: 10.1002/jssc.200401746
• 发表时间: 2004-08-01
• 期刊: JOURNAL OF SEPARATION SCIENCE
• 影响因子: 3.1
• 作者: Momchilova, S;Tsuji, K;Kuksis, A
• 通讯作者: Kuksis, A