Nakabayashi Ryo, Kusano Miyako, Kobayashi Makoto, Tohge Takayuki, Yonekura-Sakakibara Keiko, Kogure Noriyuki, Yamazaki Mami, Kitajima Mariko, Saito Kazuki, Takayama Hiromitsu
Graduate School of Pharmaceutical Sciences, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba 263-8522, Japan.
Phytochemistry. 2009 May;70(8):1017-29. doi: 10.1016/j.phytochem.2009.03.021. Epub 2009 Jun 3.
In order to conduct metabolomic studies in a model plant for genome research, such as Arabidopsis thaliana (Arabidopsis), it is a prerequisite to obtain structural information for the isolated metabolites from the plant of interest. In this study, we isolated metabolites of Arabidopsis in a relatively non-targeted way, aiming at the construction of metabolite standards and chemotaxonomic comparison. Anthocyanins (5 and 7) called A8 and A10 were isolated and their structures were elucidated as cyanidin 3-O-[2-O-(beta-D-xylopyranosyl)-6-O-(4-O-(beta-D-glucopyranosyl)-E-p-coumaroyl)-beta-D-glucopyranoside]-5-O-[6-O-(malonyl)-beta-D-glucopyranoside] and cyanidin 3-O-[2-O-(2-O-(E-sinapoyl)-beta-D-xylopyranosyl)-6-O-(4-O-(beta-D-glucopyranosyl)-E-p-coumaroyl)-beta-D-glucopyranoside]-5-O-[beta-D-glucopyranoside] from analyses of 1D NMR, 2D NMR ((1)H NMR, NOE, (13)C NMR, HMBC and HMQC), HRFABMS, FT-ESI-MS and GC-TOF-MS data. In addition, 35 known compounds, including six anthocyanins, eight flavonols, one nucleoside, one indole glucosinolate, four phenylpropanoids and a derivative, together with three indoles, one carotenoid, one apocarotenoid, three galactolipids, two chlorophyll derivatives, one steroid, one hydrocarbon, and two dicarboxylic acids, were also isolated and identified from their spectroscopic data.
为了在用于基因组研究的模式植物（如拟南芥）中开展代谢组学研究，获取目标植物中分离出的代谢物的结构信息是一个先决条件。在本研究中，我们以相对非靶向的方式分离了拟南芥的代谢物，旨在构建代谢物标准品并进行化学分类比较。分离出了名为A8和A10的花青素（5种和7种），通过对一维核磁共振（1D NMR）、二维核磁共振（（1）H NMR、NOE、（13）C NMR、HMBC和HMQC）、高分辨快原子轰击质谱（HRFABMS）、傅里叶变换电喷雾电离质谱（FT-ESI-MS）和气相色谱-飞行时间质谱（GC-TOF-MS）数据的分析，确定其结构分别为矢车菊素3-O-[2-O-(β-D-吡喃木糖基)-6-O-(4-O-(β-D-吡喃葡萄糖基)-E-p-香豆酰基)-β-D-吡喃葡萄糖苷]-5-O-[6-O-(丙二酰基)-β-D-吡喃葡萄糖苷]和矢车菊素3-O-[2-O-(2-O-(E-芥子酰基)-β-D-吡喃木糖基)-6-O-(4-O-(β-D-吡喃葡萄糖基)-E-p-香豆酰基)-β-D-吡喃葡萄糖苷]-5-O-[β-D-吡喃葡萄糖苷]。此外，还从其光谱数据中分离并鉴定出35种已知化合物，包括6种花青素、8种黄酮醇、1种核苷、1种吲哚硫代葡萄糖苷、4种苯丙烷类化合物及其衍生物，以及3种吲哚、1种类胡萝卜素、1种脱辅基类胡萝卜素、3种半乳糖脂、2种叶绿素衍生物、1种甾类化合物、1种烃类化合物和2种二元羧酸。
