2-fluoroabscisic acid analogues: their synthesis and biological activities.
Fluorine was introduced into the 2-position of the side chain of abscisic acid (ABA) analogues by Wittig reaction of alpha-ionone derivatives with ethyl triethylphosphono-2-fluoroacetate. The effects of the fluorinated analogues were evaluated on inhibition of cress seed germination and inhibition of gibberellin-inducible alpha-amylase induction in embryoless barley half-seeds. (2E, 4E)-2-Fluoro-5-(1'-hydroxy-2',6', 6'-trimethyl-2'-cyclohexen-1'-yl)-3-methyl-2,4-pentadienoic acid (5b) showed potent inhibitory activity at the same level as ABA in the cress seed germination test, and 5b also inhibited gibberellin-inducible alpha-amylase induction at 4 x 10(-)(6), 3 times the concentration of ABA (1 x 10(-)(6)) for 50% inhibition of alpha-amylase production. 5b also showed dehydrin induction activity. These results indicate that fluorinated ABA analogues mimic ABA action and can be a lead for a plant growth regulator which regulates plant growth or protects plants from environmental stresses.
Kim
B T
BT
Korea Research Institute of Chemical Technology, P.O. Box 107, Yusong, Taejon 305-606, Korea.
Min
Y K
YK
Asami
T
T
Park
N K
NK
Kwon
O Y
OY
Cho
K Y
KY
Yoshida
S
S
D000040:Abscisic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D004790:Enzyme Induction; D018525:Germination / Q000187:drug effects; D001467:Hordeum / Q000196:embryology / Q000201:enzymology
D000040:Abscisic Acid