Abscinazole-F1, a conformationally restricted analogue of the plant growth retardant uniconazole and an inhibitor of ABA 8'-hydroxylase CYP707A with no growth-retardant effect.
To develop a specific inhibitor of abscisic acid (ABA) 8'-hydroxylase, a key enzyme in the catabolism of ABA, a plant hormone involved in stress tolerance, seed dormancy, and other various physiological events, we designed and synthesized conformationally restricted analogues of uniconazole (UNI), a well-known plant growth retardant, which inhibits a biosynthetic enzyme (ent-kaurene oxidase) of gibberellin as well as ABA 8'-hydroxylase. Although most of these analogues were less effective than UNI in inhibition of ABA 8'-hydroxylase and rice seedling growth, we found that a lactol-bridged analogue with an imidazole is a potent inhibitor of ABA 8'-hydroxylase but not of plant growth. This compound, abscinazole-F1, induced drought tolerance in apple seedlings upon spray treatment with a 10 microM solution.
Todoroki
Yasushi
Y
Department of Applied Biological Chemistry, Faculty of Agriculture, Shizuoka University, Shizuoka 422-8529, Japan. aytodor@agr.shizuoka.ac.jp
Kobayashi
Kyotaro
K
Shirakura
Minaho
M
Aoyama
Hikaru
H
Takatori
Kokichi
K
Nimitkeatkai
Hataitip
H
Jin
Mei-Hong
MH
Hiramatsu
Saori
S
Ueno
Kotomi
K
Kondo
Satoru
S
Mizutani
Masaharu
M
Hirai
Nobuhiro
N
D000040:Abscisic Acid / Q000378:metabolism; D000064:Acclimatization; D065607:Cytochrome P-450 Enzyme Inhibitors; D003577:Cytochrome P-450 Enzyme System / Q000378:metabolism; D055864:Droughts; D027845:Malus / Q000502:physiology; D008968:Molecular Conformation; D012275:Oryza / Q000254:growth & development; D010937:Plant Growth Regulators / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism*; D010940:Plant Proteins; D014230:Triazoles / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism*
D065607:Cytochrome P-450 Enzyme Inhibitors; D010937:Plant Growth Regulators; D010940:Plant Proteins; D014230:Triazoles; D000040:Abscisic Acid; D003577:Cytochrome P-450 Enzyme System; C107203:abscisic acid 8'-hydroxylase; C092705:uniconazole