Kodai Tetsuya, Nakatani Takafumi, Noda Naoki
Faculty of Pharmaceutical Sciences, Setsunan University, 45-1, Nagaotoge-cho, Hirakata, Osaka, 573-0101, Japan.
Lipids. 2011 Mar;46(3):263-70. doi: 10.1007/s11745-010-3497-x. Epub 2010 Nov 17.
9-Hydroxy-2E-decenoic acid (9-HDA) is a precursor of the queen-produced substance, 9-oxo-2E-decenoic acid (9-ODA), which has various important functions and roles for caste maintenance in honeybee colonies (Apis mellifera). 9-HDA in royal jelly is considered to be a metabolite of 9-ODA produced by worker bees, and it is fed back to the queen who then transforms it into 9-ODA. Recently we found that 9-HDA is present in royal jelly as a mixture of optical isomers (R:S, 2:1). The finding leads us to suspect that chiral fatty acids in royal jelly are precursors of semiochemicals. Rather than looking for semiochemicals in the mandibular glands of the queen bee, this study involves the search for precursors of pheromones from large quantities of royal jelly. Seven chiral hydroxy fatty acids, 9,10-dihydroxy-2E-decenoic, 4,10-dihydroxy-2E-decenoic, 4,9-dihydroxy-2E-decenoic, 3-hydroxydecanoic, 3,9-dihydroxydecanoic, 3,11-dihydroxydodecanoic, and 3,10-dihydroxydecanoic acids were isolated. The absolute configurations of these acids were determined using the modified Mosher's method, and it was revealed that, similar to 9-HDA, five acids are present in royal jelly as mixtures of optical isomers.
9-羟基-2E-癸烯酸（9-HDA）是蜂王分泌物质9-氧代-2E-癸烯酸（9-ODA）的前体，9-ODA对蜜蜂蜂群（意大利蜜蜂）的等级维持具有多种重要功能和作用。蜂王浆中的9-HDA被认为是工蜂产生的9-ODA的代谢产物，并反馈给蜂王，然后蜂王将其转化为9-ODA。最近我们发现，9-HDA在蜂王浆中以旋光异构体混合物（R:S，2:1）的形式存在。这一发现使我们怀疑蜂王浆中的手性脂肪酸是信息素的前体。本研究并非在蜂王的下颌腺中寻找信息素，而是从大量蜂王浆中寻找信息素的前体。分离出了七种手性羟基脂肪酸，即9,10-二羟基-2E-癸烯酸、4,10-二羟基-2E-癸烯酸、4,9-二羟基-2E-癸烯酸、3-羟基癸酸、3,9-二羟基癸酸、3,11-二羟基十二烷酸和3,10-二羟基癸酸。使用改良的莫舍尔方法确定了这些酸的绝对构型，结果表明，与9-HDA类似，蜂王浆中有五种酸以旋光异构体混合物的形式存在。
