scholarly journals Structure-dependent absorption of atypical sphingoid long-chain bases from digestive tract into lymph

2021 ◽  
Vol 20 (1) ◽  
Author(s):  
Daisuke Mikami ◽  
Shota Sakai ◽  
Megumi Nishimukai ◽  
Kohei Yuyama ◽  
Katsuyuki Mukai ◽  
...  
Keyword(s):  
Functional Foods ◽  
Skin Barrier ◽  
Mizuhopecten Yessoensis ◽  
Amorphophallus Konjac ◽  
Chromatography Tandem Mass Spectrometry ◽  
Structural Differences ◽  
Liquid Chromatography Tandem Mass ◽  
Lymph Duct ◽  
Dependent Absorption ◽  
Long Chain

Abstract Background Dietary sphingolipids have various biofunctions, including skin barrier improvement and anti-inflammatory and anti-carcinoma properties. Long-chain bases (LCBs), the essential backbones of sphingolipids, are expected to be important for these bioactivities, and they vary structurally between species. Given these findings, however, the absorption dynamics of each LCB remain unclear. Methods In this study, five structurally different LCBs were prepared from glucosylceramides (GlcCers) with LCB 18:2(4E,8Z);2OH and LCB 18:2(4E,8E);2OH moieties derived from konjac tuber (Amorphophallus konjac), from GlcCers with an LCB 18(9Me):2(4E,8E);2OH moiety derived from Tamogi mushroom (Pleurotus cornucopiae var. citrinopileatus), and from ceramide 2-aminoethyphosphonate with LCB 18:3(4E,8E,10E);2OH moiety and LCB 18(9Me):3(4E,8E,10E);2OH moiety derived from giant scallop (Mizuhopecten yessoensis), and their absorption percentages and metabolite levels were analyzed using a lymph-duct-cannulated rat model via liquid chromatography tandem mass spectrometry (LC/MS/MS) with a multistage fragmentation method. Results The five orally administered LCBs were absorbed and detected in chyle (lipid-containing lymph) as LCBs and several metabolites including ceramides, hexosylceramides, and sphingomyelins. The absorption percentages of LCBs were 0.10–1.17%, depending on their structure. The absorption percentage of LCB 18:2(4E,8Z);2OH was the highest (1.17%), whereas that of LCB 18:3(4E,8E,10E);2OH was the lowest (0.10%). The amount of sphingomyelin with an LCB 18:2(4E,8Z);2OH moiety in chyle was particularly higher than sphingomyelins with other LCB moieties. Conclusions Structural differences among LCBs, particularly geometric isomerism at the C8–C9 position, significantly affected the absorption percentages and ratio of metabolites. This is the first report to elucidate that the absorption and metabolism of sphingolipids are dependent on their LCB structure. These results could be used to develop functional foods that are more readily absorbed.

scholarly journals Structure-dependent absorption of sphingolipid long-chain bases from the digestive tract into lymph

2020 ◽  
Author(s):  
Daisuke Mikami ◽  
Shota Sakai ◽  
Megumi Nishimukai ◽  
Kohei Yuyama ◽  
Katsuyuki Mukai ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Absorption Rate ◽  
Skin Barrier ◽  
Tandem Mass ◽  
Chromatography Tandem Mass Spectrometry ◽  
Structural Differences ◽  
Liquid Chromatography Tandem Mass ◽  
Lymph Duct ◽  
Dependent Absorption ◽  
Long Chain

Abstract Background:Dietary sphingolipids have various biofunctions, including skin barrier improvement, anti-inflammatory and anti-carcinoma properties. Long-chain bases (LCBs), the essential backbones of sphingolipids, are responsible for these bioactivities, and they vary structurally between species. Given these findings, however, the absorption dynamics of each LCB remain unclear.Methods:In this study, five structurally different LCBs were isolated and their absorption ratios and levels of their metabolites were analyzed using a lymph-duct-cannulated rat model by liquid chromatography tandem mass spectrometry (LC/MS/MS) with a novel multistage fragmentation method.Results:The five orally administered LCBs were absorbed and detected in lymph as free LCBs and several metabolites including ceramides, glucosylceramides, and sphingomyelins. The absorption rates of LCBs were 0.10-1.17% depending on their structure. The absorption rate of 4-trans,8-cis-sphingadienine was highest (1.17%), whereas that of 4-trans,8-trans,10-trans-sphingatrienine was lowest (0.10%). The amount of 4-trans,8-cis-sphingadienine-bound sphingomyelin in lymph was particularly higher than other four LCB-bound sphingomyelins.Conclusion:Structural differences among LCBs, particularly the geometric isomerism at the C8–C9 position, significant affect the absorption rate and amounts of metabolites. This is the first report revealed that the absorption rate and metabolism of sphingolipids are dependent on their LCB structure.

Direct LC–ESI–MS/MS analysis of plant glucosylceramide and ceramide species with 8E and 8Z isomers of the long chain base

2020 ◽  
Vol 85 (2) ◽  
pp. 205-210
Author(s):  
Emi Yumoto ◽  
Masaki Sato ◽  
Tomoyoshi Kubota ◽  
Hirofumi Enomoto ◽  
Koji Miyamoto ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Liquid Chromatography ◽  
Tandem Mass ◽  
Chain Base ◽  
Esi Ms ◽  
Chromatography Tandem Mass Spectrometry ◽  
Long Chain Base ◽  
Liquid Chromatography Tandem Mass ◽  
Product Ions ◽  
Long Chain

ABSTRACT Glucosylceramides and ceramides with 8E and 8Z isomers of the long chain base are found in plants. These isomers have been difficult to quantify separately using liquid chromatography–tandem mass spectrometry (LC–MS/MS) because the isomers have the same retention time, their precursor and product ions have the same m/z values, and plant ceramide standards are not commercially available. Here we tested trial separations using various ODS columns and prepared plant ceramide standards generated by human glucocerebrosidase (imiglucerase) using commercially available plant glucosylceramide standards as the substrates. Consequently, we were able to quantify the isomers based on differences in retention times in a TSKgel ODS-120A column (Tosoh, Tokyo Japan) using LC–electrospray ionization–MS/MS (LC–ESI–MS/MS).

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