Characteristic fragmentation of polyunsaturated fatty acids with allylic vicinal diols in positive-ion LC/ESI-MS/MS
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...
| Main Authors: | , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Elsevier
2023-06-01
|
| Series: | Journal of Lipid Research |
| Subjects: | |
| Online Access: | http://www.sciencedirect.com/science/article/pii/S0022227523000573 |
| _version_ | 1797797190941278208 |
|---|---|
| author | Huibin Zhu Mone Kurokawa Mengyao Chen Qiuyi Wang Masayuki Inoue Toshifumi Takao |
| author_facet | Huibin Zhu Mone Kurokawa Mengyao Chen Qiuyi Wang Masayuki Inoue Toshifumi Takao |
| author_sort | Huibin Zhu |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-03-13T03:44:28Z |
| format | Article |
| id | doaj.art-4f43d57ba34f4c1999faee0d8e3103be |
| institution | Directory Open Access Journal |
| issn | 0022-2275 |
| language | English |
| last_indexed | 2024-03-13T03:44:28Z |
| publishDate | 2023-06-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Journal of Lipid Research |
| spelling | doaj.art-4f43d57ba34f4c1999faee0d8e3103be2023-06-23T04:42:17ZengElsevierJournal of Lipid Research0022-22752023-06-01646100384Characteristic fragmentation of polyunsaturated fatty acids with allylic vicinal diols in positive-ion LC/ESI-MS/MSHuibin Zhu0Mone Kurokawa1Mengyao Chen2Qiuyi Wang3Masayuki Inoue4Toshifumi Takao5Institute for Protein Research, Osaka University, Osaka, JapanInstitute for Protein Research, Osaka University, Osaka, JapanInstitute for Protein Research, Osaka University, Osaka, JapanInstitute for Protein Research, Osaka University, Osaka, JapanGraduate School of Pharmaceutical Sciences, University of Tokyo, Tokyo, JapanInstitute for Protein Research, Osaka University, Osaka, Japan; For correspondence: Toshifumi TakaoA 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.http://www.sciencedirect.com/science/article/pii/S0022227523000573allylic vicinal diolsfragmentationhuman serumlipoxinmaresinpolyunsaturated fatty acids |
| spellingShingle | Huibin Zhu Mone Kurokawa Mengyao Chen Qiuyi Wang Masayuki Inoue Toshifumi Takao Characteristic fragmentation of polyunsaturated fatty acids with allylic vicinal diols in positive-ion LC/ESI-MS/MS Journal of Lipid Research allylic vicinal diols fragmentation human serum lipoxin maresin polyunsaturated fatty acids |
| title | Characteristic fragmentation of polyunsaturated fatty acids with allylic vicinal diols in positive-ion LC/ESI-MS/MS |
| title_full | Characteristic fragmentation of polyunsaturated fatty acids with allylic vicinal diols in positive-ion LC/ESI-MS/MS |
| title_fullStr | Characteristic fragmentation of polyunsaturated fatty acids with allylic vicinal diols in positive-ion LC/ESI-MS/MS |
| title_full_unstemmed | Characteristic fragmentation of polyunsaturated fatty acids with allylic vicinal diols in positive-ion LC/ESI-MS/MS |
| title_short | Characteristic fragmentation of polyunsaturated fatty acids with allylic vicinal diols in positive-ion LC/ESI-MS/MS |
| title_sort | characteristic fragmentation of polyunsaturated fatty acids with allylic vicinal diols in positive ion lc esi ms ms |
| topic | allylic vicinal diols fragmentation human serum lipoxin maresin polyunsaturated fatty acids |
| url | http://www.sciencedirect.com/science/article/pii/S0022227523000573 |
| work_keys_str_mv | AT huibinzhu characteristicfragmentationofpolyunsaturatedfattyacidswithallylicvicinaldiolsinpositiveionlcesimsms AT monekurokawa characteristicfragmentationofpolyunsaturatedfattyacidswithallylicvicinaldiolsinpositiveionlcesimsms AT mengyaochen characteristicfragmentationofpolyunsaturatedfattyacidswithallylicvicinaldiolsinpositiveionlcesimsms AT qiuyiwang characteristicfragmentationofpolyunsaturatedfattyacidswithallylicvicinaldiolsinpositiveionlcesimsms AT masayukiinoue characteristicfragmentationofpolyunsaturatedfattyacidswithallylicvicinaldiolsinpositiveionlcesimsms AT toshifumitakao characteristicfragmentationofpolyunsaturatedfattyacidswithallylicvicinaldiolsinpositiveionlcesimsms |