Characteristic fragmentation of polyunsaturated fatty acids with allylic vicinal diols in positive-ion LC/ESI-MS/MS |
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Affiliation: | 1. Institute for Protein Research, Osaka University, Osaka, Japan;2. Graduate School of Pharmaceutical Sciences, University of Tokyo, Tokyo, Japan |
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Abstract: | A characteristic fragmentation was observed for PUFAs that contain allylic vicinal diol groups (resolvin D1, D2, D4, E3, lipoxin A4, B4, and maresin 2), which were derivatized with N,N-dimethylethylenediamine (DMED), in positive-ion ESI-MS/MS. The findings indicate that when these compounds contain an allylic hydroxyl group that is located distal to the terminal DMED moiety in the case of resolvin D1, D4, and lipoxin A4, an aldehyde (-CH=O) is predominately formed, which arises from the breakdown in between vicinal diols, whereas, in the case of an allylic hydroxyl group that is located proximal to the DMED moiety, as in resolvin D2, E3, lipoxin B4, and maresin 2, an allylic carbene (-CH=CH-CH:) is formed. These specific fragmentations could be used as diagnostic ions for characterizing the above seven PUFAs. As a result, it was possible to detect resolvin D1, D2, E3, lipoxin A4, and B4 in sera (20 μl) obtained from healthy volunteers by multiple-reaction monitoring using LC/ESI-MS/MS. |
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Keywords: | allylic vicinal diols fragmentation human serum lipoxin maresin polyunsaturated fatty acids resolvin positive-ion ESI-MS/MS ACN" },{" #name" :" keyword" ," $" :{" id" :" kwrd0055" }," $$" :[{" #name" :" text" ," _" :" acetonitrile AMPP" },{" #name" :" keyword" ," $" :{" id" :" kwrd0065" }," $$" :[{" #name" :" text" ," $$" :[{" #name" :" italic" ," _" :" N" },{" #name" :" __text__" ," _" :" -(4-aminomethylphenyl)pyridinium CID" },{" #name" :" keyword" ," $" :{" id" :" kwrd0075" }," $$" :[{" #name" :" text" ," _" :" collision-induced dissociation DMED" },{" #name" :" keyword" ," $" :{" id" :" kwrd0085" }," $$" :[{" #name" :" text" ," $$" :[{" #name" :" italic" ," _" :" N,N" },{" #name" :" __text__" ," _" :" -dimethylethylenediamine DMF" },{" #name" :" keyword" ," $" :{" id" :" kwrd0095" }," $$" :[{" #name" :" text" ," _" :" dimethlyformamide FA" },{" #name" :" keyword" ," $" :{" id" :" kwrd0090b" }," $$" :[{" #name" :" text" ," _" :" formic acid LxA4" },{" #name" :" keyword" ," $" :{" id" :" kwrd0105" }," $$" :[{" #name" :" text" ," $$" :[{" #name" :" __text__" ," _" :" 5" },{" #name" :" italic" ," _" :" S" },{" #name" :" __text__" ," _" :" , 6" },{" #name" :" italic" ," _" :" R" },{" #name" :" __text__" ," _" :" -Lipoxin A4 LxB4" },{" #name" :" keyword" ," $" :{" id" :" kwrd0115" }," $$" :[{" #name" :" text" ," $$" :[{" #name" :" __text__" ," _" :" 5" },{" #name" :" italic" ," _" :" S" },{" #name" :" __text__" ," _" :" , 14" },{" #name" :" italic" ," _" :" R" },{" #name" :" __text__" ," _" :" -Lipoxin B4 Mar2" },{" #name" :" keyword" ," $" :{" id" :" kwrd0125" }," $$" :[{" #name" :" text" ," _" :" maresin 2 MRM" },{" #name" :" keyword" ," $" :{" id" :" kwrd0135" }," $$" :[{" #name" :" text" ," _" :" multiple-reaction monitoring RvD1" },{" #name" :" keyword" ," $" :{" id" :" kwrd0145" }," $$" :[{" #name" :" text" ," _" :" resolvin D1 RvD2" },{" #name" :" keyword" ," $" :{" id" :" kwrd0155" }," $$" :[{" #name" :" text" ," _" :" resolvin D2 RvD4" },{" #name" :" keyword" ," $" :{" id" :" kwrd0165" }," $$" :[{" #name" :" text" ," _" :" resolvin D4 RvE3R" },{" #name" :" keyword" ," $" :{" id" :" kwrd0175" }," $$" :[{" #name" :" text" ," $$" :[{" #name" :" __text__" ," _" :" 18" },{" #name" :" italic" ," _" :" R" },{" #name" :" __text__" ," _" :" -Resolvin E3 y.o." },{" #name" :" keyword" ," $" :{" id" :" kwrd0175ab" }," $$" :[{" #name" :" text" ," _" :" years old |
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