Faculty of Bioenvironmental Science, Kyoto Gakuen University, Kameoka-shi, Kyoto 621-8555, Japan.
J Chem Ecol. 2011 Mar;37(3):232-8. doi: 10.1007/s10886-011-9920-9. Epub 2011 Feb 23.
Mandelonitrile benzoate, a minor defense component produced by polydesmoid millipedes, is produced in large amounts together with hydrogen cyanide following shake-disturbances administered to individuals of Nedyopus tambanus tambanus, Parafontaria tonominea, Epanerchodus sp., and Epanerchodus fulvus. These species commonly produce mandelonitrile and benzoyl cyanide (the oxidized product after discharge). The newly generated mandelonitrile benzoate was identified as a product of post secretion Schotten-Baumann reaction under basic conditions of bled bodily fluids (pH ca. 9.0), and was not an enzymatic reaction product. The reaction occurred in vitro even under less basic conditions [1M Tris-HCl buffer (pH 8.0)], and could be defined as a new mechanism of hydrogen cyanide release occurring in roughly half of polydesmoid millipedes. Species possessing no benzoyl cyanide, such as Oxidus gracilis and Cryptocorypha sp., could also produce mandelonitrile benzoate under conditions in which benzoyl cyanide was exogenously provided.
苯甲酸苦杏仁腈是一种由多节千足虫产生的次要防御成分，在对 Nedyopus tambanus tambanus、Parafontaria tonominea、Epanerchodus sp. 和 Epanerchodus fulvus 个体进行摇晃干扰后，会与氢氰酸一起大量产生。这些物种通常会产生苦杏仁腈和苯甲酰氰化物（排出后的氧化产物）。新生成的苯甲酸苦杏仁腈被鉴定为在出血体液的碱性条件（pH 约 9.0）下分泌后 Schotten-Baumann 反应的产物，而不是酶反应产物。即使在碱性较弱的条件下（1M Tris-HCl 缓冲液，pH 8.0），反应也会在体外发生，并且可以定义为在大约一半的多节千足虫中发生氢氰酸释放的新机制。像 Oxidus gracilis 和 Cryptocorypha sp. 这样没有苯甲酰氰化物的物种，也可以在外源提供苯甲酰氰化物的条件下产生苯甲酸苦杏仁腈。
