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首页> 外文期刊>Protoplasma: An International Journal of Cell Biology >O-4-linked coniferyl and sinapyl aldehydes in lignifying cell walls are the main targets of the Wiesner (phloroglucinol-HCl) reaction
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O-4-linked coniferyl and sinapyl aldehydes in lignifying cell walls are the main targets of the Wiesner (phloroglucinol-HCl) reaction

机译：木质素化细胞壁中的O-4-连接的松柏基和芥子醛是Wiesner（间苯三酚-HCl）反应的主要目标

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摘要

The nature and specificity of the Wiesner test (phloroglucinol-HCl reagent) for the aromatic aldehyde fraction contained in lignins is studied. Phloroglucinol reacted in ethanol-hydrochloric acid with coniferyl aldehyde, sinapyl aldehyde, vanillin, and syringaldehyde to yield either pink pigments (in the case of hydroxycinnamyl aldehydes) or red-brown pigments (in the case of hydroxybenzaldehydes). However, coniferyl alcohol, sinapyl alcohol, and highly condensed dehydrogenation polymers derived from these cinnamyl alcohols and aldehydes did not react with phloroglucinol in ethanol-hydrochloric acid. The differences in the reactivity of phloroglucinol with hydroxycinnamyl aldehydes and their dehydrogenation polymers may be explained by the fact that, in the latter, the unsubstituted (alpha,beta-unsaturated) cinnamaldehyde functional group, which is responsible for the dye reaction, is lost due to lateral chain cross-linking reactions involving the beta carbon. Fourier transform infrared spectroscopy and thioacidolysis analyses of phloroglucinol-positive lignifying plant cell walls belonging to the plant species Zinnia elegans L., Capsicum annuum var. annuum, Populus alba L., and Pinus halepensis L. demonstrated the presence of 4-O-linked hydroxycinnamyl aldehyde end groups and 4-O-linked 4-hydroxy-3-methoxy-benzaldehyde (vanillin) end groups in lignins. However, given the relatively low abundance of 4-O-linked vanillin in lignifying cell walls and the low extinction coefficient of its red-brown phloroglucinol adduct, it is unlikely that vanillin contributes to a great extent to the phloroglucinol-positive stain reaction. These results suggest that the phloroglucinol-HCl pink stain of lignifying xylem cell walls actually reveals the 4-O-linked hydroxycinnamyl aldehyde structures contained in lignins. Histochemical studies showed that these aldehyde structures are assembled, as in the case of coniferyl aldehyde, during the early stages of xylem cell wall lignification. [References: 36]
机译：研究了木质素中所含芳香醛馏分的Wiesner试验（间苯三酚-HCl试剂）的性质和特异性。间苯三酚在乙醇盐酸中与松柏醛，芥子醛，香兰素和丁香醛反应，生成粉红色颜料（在羟基肉桂醛的情况下）或红棕色颜料（在羟基苯甲醛的情况下）。但是，松柏油醇，芥子醇和衍生自这些肉桂醇和醛的高度缩合的脱氢聚合物在乙醇-盐酸中不与间苯三酚反应。间苯三酚与羟基肉桂醛及其脱氢聚合物的反应性差异可能是由于以下事实造成的：在后者中，负责染料反应的未取代的（α，β-不饱和）肉桂醛官能团会丢失涉及β碳的侧链交联反应。属于植物百日菊属百日草的辣椒属植物间苯三酚阳性木质化植物细胞壁的傅里叶变换红外光谱和硫代酸解分析。年青，白杨和樟子松证明木质素中存在4-O-连接的羟基肉桂醛末端基团和4-O-连接的4-羟基-3-甲氧基-苯甲醛（香草醛）端基。但是，鉴于木质素化细胞壁中4-O-连接的香兰素相对较低的丰度以及其红棕色间苯三酚加合物的消光系数低，因此，香兰素不太可能在很大程度上促进间苯三酚阳性的染色反应。这些结果表明，木质素木质部细胞壁的间苯三酚-HCl粉红色染色实际上揭示了木质素中包含的4-O-连接的羟基肉桂醛结构。组织化学研究表明，在木质部细胞壁木质化的早期阶段，这些醛结构如松柏基醛一样被组装。 [参考：36]

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