A derivatization strategy for comprehensive identification of 2- and 3-hydroxyl fatty acids by LC-MS

doi:10.1016/j.aca.2022.339981

	A derivatization strategy for comprehensive identification of 2- and 3-hydroxyl fatty acids by LC-MS
	Zhu, Zhancheng1,2,3,4 ; Li, Xiaomei 4; Tang, Chunping 3,4; Shen, Jianhua 4; Liu, Jia 5,6; Ye, Yang1,2,3,4,5
	2022-07-11
发表期刊	ANALYTICA CHIMICA ACTA (IF:5.7[JCR-2023],5.5[5-Year])
ISSN	0003-2670
EISSN	1873-4324
卷号	1216
发表状态	已发表
DOI	10.1016/j.aca.2022.339981
摘要	2/3-Hydroxy fatty acids (2/3-OHFAs) are a class of important biological molecules closely related to many diseases, of which the unsaturated ones (2/3-OHUFAs) obtain special recognition for their bioactivities. However, the comprehensive identification of 2/3-OHFAs has been a daunting task due to the similarity of isomeric structures and lack of authentic standards. Herein, we report a strategy for the 2/3-OHUFA identification by using an in-house synthesized derivatization reagent, 4-amino-1,1-dimethylpiperidin-1-ium iodide hydrochloride (ADMI). Through ADMI derivatization, the diagnostic ion m/z 155.1 or 171.1 were produced by liquid chromatography-mass spectrometry (LC-MS) analysis, which could distinguish the 2-OH or 3-OH group, respectively. Then the meta-chloroperoxybenzoic acid (mcpba) was used to resolve the locations of double bonds in 2/3-OHUFAs by the characteristic cleavage of the newly formed epoxides. Thus, the identification of 2/3-OHUFAs was enabled by all these characteristics. Moreover, in order to simplify the whole analysis, an isotope-labeled ADMI was designed to quickly pick out the low-abundant 2/3-OHFAs from complex biological matrices. Finally, a combined derivatization strategy was established to analyze mouse lung tissues with melanoma metastasis. Different long-chain 2-OHFAs and 3-OHFAs were identified, including FA 12:0-3OH, FA 12:1(Δ9)-3OH, FA 14:0-3OH, FA 14:1(Δ5)-3OH, FA 16:0-2/3OH, and FA 18:0-2/3OH. The results showed that the contents of most identified 2/3-OHFAs were lower in the cancer group than in the control group, suggesting the plausible role of 2/3-OHFAs in cancer development. In summary, the new derivatization method provides a powerful analysis strategy for 2/3-OHUFAs, which sheds light on a better understanding of the biological functions of 2/3-OHUFAs. © 2022 Elsevier B.V.
关键词	Biological organs Cell death Diagnosis Diseases Drug products Histology Isotopes Liquid chromatography Mass spectrometry Molecules Oncology Pathology Unsaturated fatty acids 3-Hydroxy fatty acids ADMI derivatization Biological molecule Derivatizations Liquid chromatography mass spectrometries Lung metastasis m-CPBA-oxidation Melanoma lung metastasis Stable-isotope labeling Unsaturated 2/3-hydroxyl fatty acid
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收录类别	SCI ; SCIE ; EI
语种	英语
资助项目	National Natural Science Foundation of China[21920102003] ; Science and Technology Commission of Shanghai Municipality[20430780300] ; Key-Area Research and Development Program of Guangdong Province[2020B0303070002]
WOS研究方向	Chemistry
WOS类目	Chemistry, Analytical
WOS记录号	WOS:000808295500002
出版者	Elsevier B.V.
EI入藏号	20222412210101
EI主题词	Dermatology
EI分类号	461.2 Biological Materials and Tissue Engineering ; 461.6 Medicine and Pharmacology ; 461.9 Biology ; 801 Chemistry ; 804.1 Organic Compounds ; 931.3 Atomic and Molecular Physics
原始文献类型	Journal article (JA)
引用统计	正在获取...
文献类型	期刊论文
条目标识符	https://kms.shanghaitech.edu.cn/handle/2MSLDSTB/190400
专题	生命科学与技术学院_博士生生命科学与技术学院_特聘教授组_叶阳组
通讯作者	Liu, Jia; Ye, Yang
作者单位	1.ShanghaiTech Univ, Sch Life Sci & Technol, Shanghai 201210, Peoples R China 2.Univ Chinese Acad Sci, Beijing 100049, Peoples R China 3.Chinese Acad Sci, Shanghai Inst Mat Med, Nat Prod Chem Dept, Shanghai 201203, Peoples R China 4.Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, Shanghai 201203, Peoples R China 5.Chinese Acad Sci, Shanghai Inst Mat Med, Shanghai 201203, Peoples R China 6.Univ Chinese Acad Sci, Hangzhou Inst Adv Study, Sch Pharmaceut Sci & Technol, Hangzhou 310058, Peoples R China
第一作者单位	生命科学与技术学院
通讯作者单位	生命科学与技术学院
第一作者的第一单位	生命科学与技术学院
推荐引用方式 GB/T 7714	Zhu, Zhancheng,Li, Xiaomei,Tang, Chunping,et al. A derivatization strategy for comprehensive identification of 2- and 3-hydroxyl fatty acids by LC-MS[J]. ANALYTICA CHIMICA ACTA,2022,1216.
APA	Zhu, Zhancheng,Li, Xiaomei,Tang, Chunping,Shen, Jianhua,Liu, Jia,&Ye, Yang.(2022).A derivatization strategy for comprehensive identification of 2- and 3-hydroxyl fatty acids by LC-MS.ANALYTICA CHIMICA ACTA,1216.
MLA	Zhu, Zhancheng,et al."A derivatization strategy for comprehensive identification of 2- and 3-hydroxyl fatty acids by LC-MS".ANALYTICA CHIMICA ACTA 1216(2022).