1-O-(吲哚-3'-基乙酰基)-β-D-吡喃葡萄糖的化学合成。在植物切段伸长试验中，该糖苷相对于外源吲哚-3-乙酸具有更高的活性。
The chemical synthesis of 1-O-(indol-3'-ylacetyl)-beta-D-glucopyranose. The higher activity of the glucoside in comparison with exogenous indol-3-ylacetic acid in plant-section elongation tests.
作者信息
Keglević D, Pokorny M
出版信息
Biochem J. 1969 Oct;114(4):827-32. doi: 10.1042/bj1140827.
Abstract
- The synthesis of 1-O-(indol-3'-ylacetyl)-beta-d-glucopyranose via the fully benzylated 1-O-(indol-3'-ylacetyl)-d-glucopyranose is described. The configuration of the free ester glucoside was confirmed by complete hydrolysis with beta-glucosidase and by the n.m.r. spectrum of the tetra-acetyl derivative. 2. The growth-promoting effect of the glucoside in Avena coleoptile- and pea stem-section tests distinctly exceeds the responses stimulated by equimolar amounts of indol-3-ylacetic acid or equimolar mixtures of indol-3-ylacetic acid and glucose at all concentrations investigated. Time-sequence experiments revealed that the sections stimulated by the glucoside exhibit a markedly greater rate of elongation than those promoted by indol-3-ylacetic acid. 3. 1-O-(Indol-3'-ylacetyl)-beta-d-glucopyranose was isolated from intact Avena coleoptiles. 4. According to the results, the conjugation of indol-3-ylacetic acid with glucose could not be considered merely as a detoxication mechanism for indol-3-ylacetic acid in plant tissues.
摘要
- 描述了通过全苄基化的1-O-(吲哚-3'-基乙酰基)-d-吡喃葡萄糖合成1-O-(吲哚-3'-基乙酰基)-β-d-吡喃葡萄糖。通过用β-葡萄糖苷酶完全水解以及四乙酰衍生物的核磁共振光谱确定了游离酯糖苷的构型。2. 在所有研究浓度下，该糖苷在燕麦胚芽鞘和豌豆茎切段试验中的促生长作用明显超过等摩尔量的吲哚-3-乙酸或吲哚-3-乙酸与葡萄糖的等摩尔混合物所刺激的反应。时间序列实验表明，受该糖苷刺激的切段伸长速率明显高于受吲哚-3-乙酸促进的切段。3. 从完整的燕麦胚芽鞘中分离出1-O-(吲哚-3'-基乙酰基)-β-d-吡喃葡萄糖。4. 根据结果，吲哚-3-乙酸与葡萄糖的结合不能仅仅被视为植物组织中吲哚-3-乙酸的解毒机制。
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