1-(3'-O-ACYL)-BETA-GLUCOSYL-N-DIHYDROXYPENTATRIACONTADIENOYLSPHINGOSINE, A MAJOR COMPONENT OF GLUCOSYLCERAMIDES OF PIG AND HUMAN EPIDERMIS
1-(3'-O-ACYL)-BETA-GLUCOSYL-N-DIHYDROXYPENTATRIACONTADIENOYLSPHINGOSINE, A MAJOR COMPONENT OF GLUCOSYLCERAMIDES OF PIG AND HUMAN EPIDERMIS
复制标题
DOI：
10.1016/0005-2760(78)90058-9
复制
发表时间：
1978-01-01
期刊：
影响因子：
--
通讯作者：
MAJER, JR
中科院分区：
文献类型：
--
作者：
GRAY, GM;WHITE, RJ;MAJER, JR
从其红外光谱和降解产物中鉴定出猪和人表皮中 4 种色谱上不同的葡萄糖神经酰胺中极性最小的为 O-酰基葡萄糖神经酰胺。全甲基化研究表明，猪的酰基主要（80%）附着在葡萄糖的 C-3 上，而人 O-酰基葡萄糖神经酰胺中的酰基仅附着在葡萄糖的 C-3 上。十八碳二烯酸是猪和人O-酰基葡萄糖神经酰胺中与葡萄糖酯化的主要酸，二氢鞘氨醇、二氢鞘氨醇和十七二氢鞘氨醇占长链碱基的大部分（猪中87%，人中80%）。色谱和化学证据表明，具有超过 30 个碳原子的单一未知不饱和二羟基脂肪酸通过酰胺键连接到鞘氨醇上。这通过质谱分析得到证实。精确的质量测量表明该酸的相对分子量为 550.496115 (C35H66O4)，是具有 2 个双键的二羟基酸。其他质谱数据表明羟基和双键仅限于 C-16 和 C-20 之间的区域。猪表皮中的 O-酰基葡萄糖神经酰胺和人表皮中的 O-酰基葡萄糖神经酰胺，由于其性质非常相似，可能也是 1-(3''-O-酰基)-β-葡萄糖基-N-二羟基五十三二烯酰鞘氨醇。
The least polar of 4 chromatographically distinct glucosylceramides in both pig and human epidermis was identified from its IR spectrum and degradation products as O-acylglucosylceramide. Permethylation studies indicated that the acyl group was attached predominantly (80%) to the C-3 of glucose in the pig and only to the C-3 of glucose in human O-acylglucosylceramide. Octadecadienoic acid was the major acid esterified to glucose in both pig and human O-acylglucosylceramides and sphingenine, sphinganine and heptadecasphinganine accounted for most of the long chain bases (87% in pig, 80% in human). Chromatographic and chemical evidence suggested that a single, unknown unsaturated dihydroxy fatty acid with more than 30 carbon atoms was attached through the amide link to the sphingosines. This was confirmed by mass spectrometry. Precise mass measurements indicated that the acid had a relative MW of 550.496115 (C35H66O4) and was a dihydroxy acid with 2 double bonds. Other mass spectrometric data suggested that the hydroxyl groups and double bonds were confined to the region between C-16 and C-20. The O-acylglucosylceramide in pig epidermis and, by the close similarity of its properties, probably that in human epidermis also was 1-(3''-O-acyl)-.beta.-glucosyl-N-dihydroxypentatriacontadienoylsphingosine.