TY - JOUR
T1 - Design and chemical synthesis of root gravitropism inhibitors
T2 - Bridged analogues of ku-76 have more potent activity
AU - Shindo, Mitsuru
AU - Makigawa, Saki
AU - Kodama, Kozue
AU - Sugiyama, Hiromi
AU - Matsumoto, Kenji
AU - Iwata, Takayuki
AU - Wasano, Naoya
AU - Kano, Arihiro
AU - Morita, Miyo Terao
AU - Fujii, Yoshiharu
N1 - Funding Information:
This research was financially supported by JSPS KAKENHI Grant Number (No. JP22390002, JP24106731, JP16H01157, JP26293004, JP17K14449, JP18H04418, JP18H04624, and JP18H02557), Science and Technology Research Promotion Program for Agriculture, Forestry, Fisheries and Food industry (M.S.). This work was performed under the Cooperative Research Program “Network Joint Research Center for Materials and Devices.”
PY - 2020/11
Y1 - 2020/11
N2 - Previously, we found (2Z,4E)-5-phenylpenta-2,4-dienoic acid (ku-76) to be a selective inhibitor of root gravitropic bending of lettuce radicles at 5 μM, with no concomitant growth inhibition, and revealed the structure–activity relationship in this inhibitory activity. The conformation of ku-76 is flexible owing to the open-chain structure of pentan-2,4-dienoic acid with freely rotating single bonds, and the (2Z)-alkene moiety may be isomerized by external factors. To develop more potent inhibitors and obtain insight into the target biomolecules, various analogues of ku-76, fixed through conformation and/or configuration, were synthesized and evaluated. Stereochemical fixation was effective in improving the potency of gravitropic bending inhibition. Finally, we found highly potent conformational and/or configurational analogues (ku-257, ku-294 and ku-308), that did not inhibit root growth. The inhibition of root curvature by these analogues was comparable to that of naptalam.
AB - Previously, we found (2Z,4E)-5-phenylpenta-2,4-dienoic acid (ku-76) to be a selective inhibitor of root gravitropic bending of lettuce radicles at 5 μM, with no concomitant growth inhibition, and revealed the structure–activity relationship in this inhibitory activity. The conformation of ku-76 is flexible owing to the open-chain structure of pentan-2,4-dienoic acid with freely rotating single bonds, and the (2Z)-alkene moiety may be isomerized by external factors. To develop more potent inhibitors and obtain insight into the target biomolecules, various analogues of ku-76, fixed through conformation and/or configuration, were synthesized and evaluated. Stereochemical fixation was effective in improving the potency of gravitropic bending inhibition. Finally, we found highly potent conformational and/or configurational analogues (ku-257, ku-294 and ku-308), that did not inhibit root growth. The inhibition of root curvature by these analogues was comparable to that of naptalam.
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U2 - 10.1016/j.phytochem.2020.112508
DO - 10.1016/j.phytochem.2020.112508
M3 - Article
AN - SCOPUS:85090188168
VL - 179
JO - Phytochemistry
JF - Phytochemistry
SN - 0031-9422
M1 - 112508
ER -