Determination of the Absolute Configuration of a Monoglyceride Antibolting Compound and Isolation of Related Compounds from Radish Leaves (Raphanus sativus)

被引：14

作者：

Ogihara, Tsuyoshi ^{[1
]}

Amano, Naruki ^{[1
]}

Mitsui, Yuki ^{[2
]}

Fujino, Kaien ^{[1
]}

Ohta, Hiroyuki ^{[3
]}

Takahashi, Kosaku ^{[1
]}

Matsuura, Hideyuki ^{[1
]}

机构：

[1] Hokkaido Univ, Res Fac Agr, Sapporo, Hokkaido 0608589, Japan

[2] Tokyo Univ Agr, Setagaya Ku, 1-1-1 Sakuragaoka, Tokyo 1568502, Japan

[3] Tokyo Inst Technol, Sch Life Sci & Technol, Midori Ku, 4259-B65 Nagatsuta Cho, Yokohama, Kanagawa 2268501, Japan

来源：

JOURNAL OF NATURAL PRODUCTS | 2017年 / 80卷 / 04期

关键词：

INDUCED STEM ELONGATION; JASMONIC ACID; JAPANESE RADISH; GIBBERELLINS; INHIBITION; PLANTS; ROOT;

D O I：

10.1021/acs.jnatprod.6b00746

中图分类号：

Q94 [植物学];

学科分类号：

071001 ;

摘要：

A 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 beta-(7'Z,10'Z,13'Z)-hexadecatrienoic acid monoglyceride monoglyceride (beta-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 /AM in the medium. However, the inhibitory effect of 1 was not dependent on coronatin-insensitive 1 (COD) protein, which may suggest the involvement of an unidentified signaling system other than jasmonic acid signaling.

引用

页码：872 / 878

页数：7