Noda Naoki, Umebayashi Kazue, Nakatani Takafumi, Miyahara Kazumoto, Ishiyama Kaori
Faculty of Pharmaceutical Sciences, Setsunan University, Osaka, Japan.
Lipids. 2005 Aug;40(8):833-8. doi: 10.1007/s11745-005-1445-6.
The present work characterizes novel FA in the royal jelly of honeybees (Apis mellifera). TLC analysis showed that the chloroform/methanol extract obtained from royal jelly consists mainly of FA. The FABMS spectrum of this extract gave several ion peaks due to compounds with higher M.W. than those of the FA so far reported. The methanol extract was found to contain unknown phospholipids. By means of reversed-phase HPLC with various solvent systems, 13 compounds were obtained in pure state. Their structures including absolute configurations were determined by chemical, NMR, and MS spectral analysis. Six compounds were identified as novel mono- or di-esters of 10-hydroxy-2E-decenoic acid in which the hydroxyl group was esterified by another FA unit, and one was hydroxy-2E-decenoic acid 10-phosphate. In addition, we demonstrated that 9-hydroxy-2E-decenoic acid exists as a mixture of optical isomers.
本研究对蜜蜂（意大利蜜蜂）蜂王浆中的新型脂肪酸进行了表征。薄层色谱分析表明，从蜂王浆中获得的氯仿/甲醇提取物主要由脂肪酸组成。该提取物的快原子轰击质谱给出了几个离子峰，这些离子峰来自分子量高于迄今报道的脂肪酸的化合物。发现甲醇提取物含有未知的磷脂。通过使用各种溶剂系统的反相高效液相色谱法，得到了13种纯态化合物。通过化学、核磁共振和质谱光谱分析确定了它们的结构，包括绝对构型。六种化合物被鉴定为10-羟基-2E-癸烯酸的新型单酯或二酯，其中羟基被另一个脂肪酸单元酯化，一种是10-磷酸羟基-2E-癸烯酸。此外，我们证明了9-羟基-2E-癸烯酸以旋光异构体混合物的形式存在。
