Metabolomics-oriented isolation and structure elucidation of 37 compounds including two anthocyanins from Arabidopsis thaliana.
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.
Nakabayashi
Ryo
R
Graduate School of Pharmaceutical Sciences, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba 263-8522, Japan.
Kusano
Miyako
M
Kobayashi
Makoto
M
Tohge
Takayuki
T
Yonekura-Sakakibara
Keiko
K
Kogure
Noriyuki
N
Yamazaki
Mami
M
Kitajima
Mariko
M
Saito
Kazuki
K
Takayama
Hiromitsu
H
D000872:Anthocyanins / Q000737:chemistry* / Q000145:classification / Q000302:isolation & purification*; D017360:Arabidopsis / Q000737:chemistry*; D002338:Carotenoids / Q000737:chemistry / Q000302:isolation & purification*; D038983:Galactolipids / Q000737:chemistry / Q000302:isolation & purification; D005960:Glucosides / Q000737:chemistry / Q000302:isolation & purification; D007211:Indoles / Q000737:chemistry / Q000494:pharmacology; D015394:Molecular Structure
D000872:Anthocyanins; D038983:Galactolipids; D005960:Glucosides; D007211:Indoles; D002338:Carotenoids