Structural characterization of the major flavonoid glycosides from Arabidopsis thaliana seeds
Structural characterization of the major flavonoid glycosides from Arabidopsis thaliana seeds
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DOI：
10.1021/jf061043n
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发表时间：
2006-09-06
影响因子：
6.1
通讯作者：
Birlirakis, Nicolas
中科院分区：
文献类型：
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作者：
Kerhoas, Lucien;Aouak, Denya;Birlirakis, Nicolas
从模式植物拟南芥（芸苔科）种子中获得的信息有助于更好地了解类黄酮的合成，并可用于作物改良。然而，对拟南芥种子中积累的黄酮类化合物的详尽鉴定仍然缺乏。通过LC-ESI-MS、LC-ESI-MS和NMR对拟南芥种子中的黄酮类化合物进行了补充研究，得到了单糖苷类化合物（槲皮素3- o - α -鼠李糖苷和山奈酚3- o - α -鼠李糖苷）和二糖苷类化合物（槲皮素和山奈酚3- o - β -葡萄糖苷-7- o - α -鼠李糖苷）以及槲皮素和山奈酚3,7-二- o - α -鼠李糖苷)的完整表征。有趣的是，缺乏类黄酮-3′-羟化酶并因此只积累山奈酚衍生物的tt7突变体含有另外三种产物，山奈酚3- o - β -葡萄糖苷，山奈酚3- o - α -鼠李糖苷-7- o - β -葡萄糖苷和山奈酚3- o - β -[α -鼠李糖苷(1 - bbbb2)-葡萄糖苷]-7- o - α -鼠李糖苷。综上所述，这些结果允许提出黄酮醇糖基化的方案。
Information gains from the seed of the model plant Arabidopsis thaliana( Brassicaceae) have greatly contributed to a better understanding of flavonoid synthesis and may be used for crop improvement. However, exhaustive identification of the flavonoid accumulated in Arabidopsis seed was still lacking. Complementary investigations of seed flavonoids by LC-ESI-MS, LC-ESI-MS-MS, and NMR spectroscopy in Arabidopsis led to full characterization of monoglycosides, namely, quercetin 3-O-alpha-rhamnopyranoside and kaempferol 3-O-alpha-rhamnopyranoside, and diglycosides, namely, quercetin and kaempferol 3-O-beta-glucopyranoside-7-O-alpha-rhamnopyranoside and quercetin and kaempferol 3,7-di-O-alpha-rhamnopyranoside. Interestingly, the tt7 mutant that lacks flavonoid-3'-hydroxylase and consequently accumulates only kaempferol derivatives was shown to contain three additional products, kaempferol 3-O-beta-glucopyranoside, kaempferol 3-O-alpha-rhamnopyranoside-7-O-beta-glucopyranoside, and the triglycoside kaempferol 3-O-beta-[alpha-rhamnopyranosyl(1 -> 2)-glucopyranoside]-7-O-alpha-rhamnopyranoside. Taken together these results allow a scheme for flavonol glycosylation to be proposed.