Linoleate-rich acylglucosylceramides of pig epidermis: structure determination by proton magnetic resonance.
The structure of the linoleate-rich acylglycosylceramides isolated from pig epidermis has been reinvestigated. Gas-liquid chromatographic analysis of the alditol acetates produced from the sugar component indicated that 90% of the hexose is glucose while the remaining 10% is galactose. The predomina...
| Main Authors: | , , |
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| Format: | Article |
| Language: | English |
| Published: |
Elsevier
1985-06-01
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| Series: | Journal of Lipid Research |
| Online Access: | http://www.sciencedirect.com/science/article/pii/S0022227520343340 |
| _version_ | 1818862805077458944 |
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| author | W Abraham P W Wertz D T Downing |
| author_facet | W Abraham P W Wertz D T Downing |
| author_sort | W Abraham |
| collection | DOAJ |
| description | The structure of the linoleate-rich acylglycosylceramides isolated from pig epidermis has been reinvestigated. Gas-liquid chromatographic analysis of the alditol acetates produced from the sugar component indicated that 90% of the hexose is glucose while the remaining 10% is galactose. The predominance of the beta-D-glucosyl group was confirmed by 360 MHz proton magnetic resonance spectroscopy. The magnetic resonance method was also used to prove that the ester-linked linoleic acid is actually attached to the omega-hydroxyl group of the long chain hydroxyacid, not to the sugar as had been reported previously. A key spectral feature supporting this new structural assignment was a triplet at 3.82 ppm, which indicates methylene protons between another methylene and an ester linkage. After saponification, this signal moved to 3.33 ppm, a chemical shift expected for a methylene bearing a free hydroxyl group. Furthermore, all of the sugar ring protons could be accounted for both before and after acetylation. No evidence was found to suggest that an ester is attached to the sugar ring in the native material. It is concluded that the principal porcine epidermal acylglycosylceramide is 1-beta-D-glucosyl-N-(omega-O-linoleoyl)-triacontanoylsphingosine. |
| first_indexed | 2024-12-19T10:05:42Z |
| format | Article |
| id | doaj.art-e5f40a06836e4c3b8ce4eb9b94197f67 |
| institution | Directory Open Access Journal |
| issn | 0022-2275 |
| language | English |
| last_indexed | 2024-12-19T10:05:42Z |
| publishDate | 1985-06-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Journal of Lipid Research |
| spelling | doaj.art-e5f40a06836e4c3b8ce4eb9b94197f672022-12-21T20:26:31ZengElsevierJournal of Lipid Research0022-22751985-06-01266761766Linoleate-rich acylglucosylceramides of pig epidermis: structure determination by proton magnetic resonance.W AbrahamP W WertzD T DowningThe structure of the linoleate-rich acylglycosylceramides isolated from pig epidermis has been reinvestigated. Gas-liquid chromatographic analysis of the alditol acetates produced from the sugar component indicated that 90% of the hexose is glucose while the remaining 10% is galactose. The predominance of the beta-D-glucosyl group was confirmed by 360 MHz proton magnetic resonance spectroscopy. The magnetic resonance method was also used to prove that the ester-linked linoleic acid is actually attached to the omega-hydroxyl group of the long chain hydroxyacid, not to the sugar as had been reported previously. A key spectral feature supporting this new structural assignment was a triplet at 3.82 ppm, which indicates methylene protons between another methylene and an ester linkage. After saponification, this signal moved to 3.33 ppm, a chemical shift expected for a methylene bearing a free hydroxyl group. Furthermore, all of the sugar ring protons could be accounted for both before and after acetylation. No evidence was found to suggest that an ester is attached to the sugar ring in the native material. It is concluded that the principal porcine epidermal acylglycosylceramide is 1-beta-D-glucosyl-N-(omega-O-linoleoyl)-triacontanoylsphingosine.http://www.sciencedirect.com/science/article/pii/S0022227520343340 |
| spellingShingle | W Abraham P W Wertz D T Downing Linoleate-rich acylglucosylceramides of pig epidermis: structure determination by proton magnetic resonance. Journal of Lipid Research |
| title | Linoleate-rich acylglucosylceramides of pig epidermis: structure determination by proton magnetic resonance. |
| title_full | Linoleate-rich acylglucosylceramides of pig epidermis: structure determination by proton magnetic resonance. |
| title_fullStr | Linoleate-rich acylglucosylceramides of pig epidermis: structure determination by proton magnetic resonance. |
| title_full_unstemmed | Linoleate-rich acylglucosylceramides of pig epidermis: structure determination by proton magnetic resonance. |
| title_short | Linoleate-rich acylglucosylceramides of pig epidermis: structure determination by proton magnetic resonance. |
| title_sort | linoleate rich acylglucosylceramides of pig epidermis structure determination by proton magnetic resonance |
| url | http://www.sciencedirect.com/science/article/pii/S0022227520343340 |
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