10.1021/acs.jnatprod.6b00746.s001
Tsuyoshi Ogihara
Tsuyoshi
Ogihara
Naruki Amano
Naruki
Amano
Yuki Mitsui
Yuki
Mitsui
Kaien Fujino
Kaien
Fujino
Hiroyuki Ohta
Hiroyuki
Ohta
Kosaku Takahashi
Kosaku
Takahashi
Hideyuki Matsuura
Hideyuki
Matsuura
Determination of the Absolute Configuration of a Monoglyceride
Antibolting Compound and Isolation of Related Compounds from Radish
Leaves (<i>Raphanus sativus</i>)
American Chemical Society
2017
coronatin-insensitive 1
jasmonic acid
Arabidopsis thaliana seedlings
C -2 position
monoglyceride
configuration
deuterium-labeled compounds
winter crops
Raphanus sativus
COI
Monoglyceride Antibolting
Related Compounds
50 μ M
chemical structure
antibolting effect
Radish Leaves
Absolute Configuration
root elongation
2017-03-23 15:03:26
Journal contribution
https://acs.figshare.com/articles/journal_contribution/Determination_of_the_Absolute_Configuration_of_a_Monoglyceride_Antibolting_Compound_and_Isolation_of_Related_Compounds_from_Radish_Leaves_i_Raphanus_sativus_i_/4781143
A monoglyceride (<b>1</b>)
has been reported to possess an
antibolting effect in radish (<i>Raphanus sativus</i>),
but its absolute configuration at the C-2 position was not determined
earlier. In this work, the absolute configuration of <b>1</b> was determined to be (2<i>S</i>), and it was also accompanied
by one new (<b>2</b>) and two known monoglycerides (<b>3</b> and <b>4</b>). The chemical structure of <b>2</b> was
determined as β-(7′<i>Z</i>,10′<i>Z</i>,13′<i>Z</i>)-hexadecatrienoic acid monoglyceride
(β-16:3 monoglyceride). Qualitative and quantitative analytical
methods for compounds <b>1</b>–<b>4</b> were developed,
using two deuterium-labeled compounds (<b>8</b> and <b>9</b>) as internal standards. The results revealed a broader range of
distribution of <b>1</b>–<b>4</b> in several annual
winter crops. It was also found that these isolated compounds have
an inhibitory effect on the root elongation of <i>Arabidopsis
thaliana</i> seedlings at concentrations of 25 and 50 μM
in the medium. However, the inhibitory effect of <b>1</b> was
not dependent on coronatin-insensitive 1 (COI1) protein, which may
suggest the involvement of an unidentified signaling system other
than jasmonic acid signaling.