TY - JOUR
T1 - Characterization of a helminthosporic acid analog that is a selective agonist of gibberellin receptor
AU - Miyazaki, Sho
AU - Tomita, Kenji
AU - Yamane, Hisakazu
AU - Kobayashi, Masatomo
AU - Asami, Tadao
AU - Nakajima, Masatoshi
N1 - Funding Information:
This work was supported in part by grants from the Japan Society for the Promotion of Science (JSPS) KAKENHI (Grant nos. 24380060 , 15H04492 , and 18H02142 to MN and 16K18693 to SM), the Agricultural Chemical Research Foundation (to SM), and the Wada Kunko-kai Research Foundation (to MN).
Publisher Copyright:
© 2018 Elsevier Ltd
PY - 2018/8/1
Y1 - 2018/8/1
N2 - Helminthosporol, a natural growth regulator isolated from a fungus, stimulates hypocotyl growth and seed germination, similar to gibberellin (GA). We recently reported that helminthosporic acid (H-acid), a synthetic analog of helminthosporol, acts as an agonist of GA receptor. In this study, we showed that a H-acid analog, in which the hydroxymethyl group at the C-8 position of H-acid was converted to a keto group, acts as a selective GA receptor agonist. 1) This analog shows higher hypocotyl elongation activity in Arabidopsis than H-acid does, and induces the degradation of DELLA protein and 2) leads to the formation of the GID1-DELLA complex and 3) regulates the expression of GA-related genes. In addition, 4) its hypocotyl elongation activity was not observed in a atgid1a single mutant, and 5) this analog could promote only the interaction between specific GA receptors and DELLA proteins in vitro. Taken together, our results strongly suggest that the selectivity of the reported H-acid analog depends on the specificity of its GA receptor binding activity.
AB - Helminthosporol, a natural growth regulator isolated from a fungus, stimulates hypocotyl growth and seed germination, similar to gibberellin (GA). We recently reported that helminthosporic acid (H-acid), a synthetic analog of helminthosporol, acts as an agonist of GA receptor. In this study, we showed that a H-acid analog, in which the hydroxymethyl group at the C-8 position of H-acid was converted to a keto group, acts as a selective GA receptor agonist. 1) This analog shows higher hypocotyl elongation activity in Arabidopsis than H-acid does, and induces the degradation of DELLA protein and 2) leads to the formation of the GID1-DELLA complex and 3) regulates the expression of GA-related genes. In addition, 4) its hypocotyl elongation activity was not observed in a atgid1a single mutant, and 5) this analog could promote only the interaction between specific GA receptors and DELLA proteins in vitro. Taken together, our results strongly suggest that the selectivity of the reported H-acid analog depends on the specificity of its GA receptor binding activity.
KW - GA-like
KW - GID1
KW - Natural product
KW - Plant hormone
KW - Selectivity
KW - Terpenoid
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U2 - 10.1016/j.bmcl.2018.06.005
DO - 10.1016/j.bmcl.2018.06.005
M3 - Article
C2 - 29907394
AN - SCOPUS:85048332017
SN - 0960-894X
VL - 28
SP - 2465
EP - 2470
JO - Bioorganic and Medicinal Chemistry Letters
JF - Bioorganic and Medicinal Chemistry Letters
IS - 14
ER -