Yano I, Tomiyasu I, Kaneda K, Kato Y, Sumi Y, Kurano S, Sugimoto N, Sawai H
J Pharmacobiodyn. 1987 Mar;10(3):113-23. doi: 10.1248/bpb1978.10.113.
Three classes of glycolipids (TMM (trehalose monomycolate), TDM (trehalose dimycolate) and GM (glucose mycolate] containing mycolic acids as hydrophobic components were isolated from a strain of Nocardia rubra (Rhodococcus rubrum) and their structures have been partially characterized using infrared spectrometry, gas-liquid chromatography and gas chromatography-mass spectrometry. Acid or alkaline hydrolysis of isolated glycolipids revealed that trehalose was the sole water soluble component in TMM and TDM, while glucose was the hydrophilic component in GM. On the other hand, saturated, monoenoic and dienoic mycolic acids with carbon atoms ranging from C36 to C50 contained constituents of fatty acid moiety at C44. From the analytical results, TMM, TDM and GM were tentatively identified as trehalose monomycolate, trehalose dimycolate and glucose monomycolate, respectively. The mycolic acid composition differed significantly by the glycolipid classes: the highest amount of saturated mycolic acids were detected in TMM and GM, while a significant amount of dienoic mycolic acids have been found in TDM and the cell wall bound lipid fraction (BL). All these three classes of glycolipids containing mycolic acids showed strong granuloma forming activity in lungs and spleen of ICR mice 1 week after intravenous injection of 100 to 500 micrograms glycolipid in W/O/W micelles containing Freund's incomplete adjuvant. These results indicated that glycolipids containing shorter carbon chain mycolic acids ranging C40-50, corresponding to less acyl numbers or monosaccharides such as glucose, can also produce foreign body-type granuloma in mice without protein antigens.
从一株红色诺卡氏菌（红球菌）中分离出了三类糖脂（海藻糖单霉菌酸酯、海藻糖双霉菌酸酯和葡萄糖霉菌酸酯），它们含有霉菌酸作为疏水成分，并利用红外光谱、气液色谱和气相色谱-质谱对其结构进行了部分表征。对分离出的糖脂进行酸或碱水解后发现，海藻糖是海藻糖单霉菌酸酯和海藻糖双霉菌酸酯中唯一的水溶性成分，而葡萄糖是葡萄糖霉菌酸酯中的亲水成分。另一方面，碳原子数在C36至C50之间的饱和、单烯和二烯霉菌酸在C44处含有脂肪酸部分的成分。根据分析结果，海藻糖单霉菌酸酯、海藻糖双霉菌酸酯和葡萄糖单霉菌酸酯分别被初步鉴定为海藻糖单霉菌酸酯、海藻糖双霉菌酸酯和葡萄糖单霉菌酸酯。不同类别的糖脂中霉菌酸的组成差异显著：在海藻糖单霉菌酸酯和葡萄糖单霉菌酸酯中检测到的饱和霉菌酸含量最高，而在海藻糖双霉菌酸酯和细胞壁结合脂质部分（BL）中发现了大量的二烯霉菌酸。在含有弗氏不完全佐剂的W/O/W微囊中静脉注射100至500微克糖脂1周后，所有这三类含霉菌酸的糖脂在ICR小鼠的肺和脾中均表现出很强的肉芽肿形成活性。这些结果表明，含有碳链较短（C40-50）、对应酰基数量较少的霉菌酸或单糖（如葡萄糖）的糖脂，在没有蛋白质抗原的情况下也能在小鼠体内产生异物型肉芽肿。
