np6b00746_si_001.pdf (2.98 MB)
Determination of the Absolute Configuration of a Monoglyceride Antibolting Compound and Isolation of Related Compounds from Radish Leaves (Raphanus sativus)
journal contribution
posted on 2017-03-23, 15:03 authored by Tsuyoshi Ogihara, Naruki Amano, Yuki Mitsui, Kaien Fujino, Hiroyuki Ohta, Kosaku Takahashi, Hideyuki MatsuuraA monoglyceride (1)
has been reported to possess an
antibolting effect in radish (Raphanus sativus),
but its absolute configuration at the C-2 position was not determined
earlier. In this work, the absolute configuration of 1 was determined to be (2S), and it was also accompanied
by one new (2) and two known monoglycerides (3 and 4). The chemical structure of 2 was
determined as β-(7′Z,10′Z,13′Z)-hexadecatrienoic acid monoglyceride
(β-16:3 monoglyceride). Qualitative and quantitative analytical
methods for compounds 1–4 were developed,
using two deuterium-labeled compounds (8 and 9) as internal standards. The results revealed a broader range of
distribution of 1–4 in several annual
winter crops. It was also found that these isolated compounds have
an inhibitory effect on the root elongation of Arabidopsis
thaliana seedlings at concentrations of 25 and 50 μM
in the medium. However, the inhibitory effect of 1 was
not dependent on coronatin-insensitive 1 (COI1) protein, which may
suggest the involvement of an unidentified signaling system other
than jasmonic acid signaling.