Isolation of lignin–carbohydrate bonds in wood. Model experiments and preliminary application to pine wood
Isolation of lignin–carbohydrate bonds in wood. Model experiments and preliminary application to pine wood
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DOI：
10.1007/s10086-003-0542-x
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发表时间：
2004-04
影响因子：
2.9
通讯作者：
Olov Karlsson;T. Ikeda;T. Kishimoto;K. Magara;Y. Matsumoto;S. Hosoya
中科院分区：
文献类型：
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作者：
Olov Karlsson;T. Ikeda;T. Kishimoto;K. Magara;Y. Matsumoto;S. Hosoya
建立了一种利用模型化合物分析苯醚型木质素-碳水化合物键的新方法。模型化合物3-（4-羟基-3-甲氧基苯基）-2-（2-甲氧基苯氧基）-3-（甲基β-d-葡萄糖吡喃苷-6- o -基）-1-丙醇（GGMGP）的4个非对映体，在0℃下以醋酸/水/甲醇16:3:1臭氧化1h。对各非对映体的臭氧化产物进行皂化处理，并用离子交换色谱分离得到相应的α-醚化四烯酸（TAMGP）。在臭氧化苯醚型模型化合物的产物混合物中检测到少量的甲基β-d-葡萄糖吡喃苷（MGP）和少量的与戊二酸醚化的葡萄糖酸（TAGLCA）、戊二酸、葡萄糖酸和甘油酸。结果表明，在臭氧处理过程中，木质素与碳水化合物之间的苯醚键相当稳定。用衍生TAMGP的硫酸或三氟乙酸进行酸处理可导致糖苷键断裂，但α-醚键断裂仅生成少量产物（四酸和葡萄糖）。将成功的化学处理方法应用于日本红松苯醚键的研究。结果表明，在木材多糖存在苯醚键。
A novel method for analysis of benzylic ether type lignin–carbohydrate bonds has been developed by using model compounds. Four diastereomers of model compound 3-(4-hydroxy-3-methoxyphenyl)-2-(2-methoxyphenoxy)-3-(methylβ-d-glucopyranoside-6-O-yl)-1-propanol (GGMGP), were ozonized in acetic acid/water/methanol 16 : 3 : 1 for 1 h at 0°C. The product from ozonation of each diastereomer was saponified and the correspondingα-etherified tetronic acid (TAMGP) was isolated using ion exchange chromatography. Minor amounts of methylβ-d-glucopyranoside (MGP) and small amounts of a gluconic acid etherified with tetronic acid (TAGLCA), tetronic acid, gluconic acid, and glyceric acid were detected in the product mixture of ozonated benzylic ether type model compounds. The results suggest that a benzyl ether bond between lignin and carbohydrate is rather stable during the ozone treatment. Acid treatments with sulfuric acid or trifluoroacetic acid of the derived TAMGP led to cleavage of the glucosidic bond but only a small amount of products (tetronic acid and glucose) resulting from cleavage of theα-ether bond were formed. The successful chemical treatments were used for studies of benzylic ether bonds in Japanese red pine. The results suggest the presence of benzylic ether bonds to polysaccharides in the wood.