Moser Simone, Ulrich Markus, Müller Thomas, Kräutler Bernhard
Institute of Organic Chemistry, Innrain 52a & Centre of Molecular Biosciences, University of Innsbruck, A-6020, Innsbruck, Austria.
Photochem Photobiol Sci. 2008 Dec;7(12):1577-81. doi: 10.1039/b813558d. Epub 2008 Oct 17.
Here we describe the detection and identification of a yellow chlorophyll catabolite (Cj-YCC) in fresh extracts of senescent leaves of Cercidiphyllum japonicum. In addition, we report its partial synthesis by oxidation of Cj-NCC-1, the major (colourless) "nonfluorescent" chlorophyll catabolite (NCC) found in degreened leaves of C. japonicum. The spectroscopic analysis and structural characterization indicated Cj-YCC to be a simple dehydrogenation product of Cj-NCC-1 (by formal removal of a hydrogen atom at the C(20)- and C(1)-positions). Indeed, NCCs are easily oxidized and were first called "rusty pigments", as they had a tendency to turn brown upon storage on a dry silica gel plate. The yellow tetrapyrrole Cj-YCC may thus come about by oxidation of Cj-NCC-1 in the leaves. Its presence in the yellow leaves of a deciduous tree provides the first evidence for the contribution of a coloured chlorophyll catabolite to the fall colours.
在此,我们描述了在日本连香树衰老叶片的新鲜提取物中对一种黄色叶绿素分解产物(Cj - YCC)的检测与鉴定。此外,我们报告了通过氧化Cj - NCC - 1实现其部分合成,Cj - NCC - 1是在日本连香树脱绿叶片中发现的主要(无色)“非荧光”叶绿素分解产物(NCC)。光谱分析和结构表征表明Cj - YCC是Cj - NCC - 1的简单脱氢产物(通过在C(20) - 和C(1) - 位置正式去除一个氢原子)。实际上,NCC很容易被氧化,并且最初被称为“生锈色素”,因为它们在干燥硅胶板上储存时容易变成棕色。黄色四吡咯Cj - YCC因此可能是由叶片中的Cj - NCC - 1氧化产生的。它在落叶树黄叶中的存在为有色叶绿素分解产物对秋季色彩的贡献提供了首个证据。