Stress-induced factor involved in flower formation of Lemna is an alpha-ketol derivative of linolenic acid.
A stress-induced substance(s) (factor C) incubated with norepinephrine (NE) has strong flower-inducing activity in Lemna paucicostata. We isolated an essential component (FIF) of factor C, and clarified its chemical structure as 9-hydroxy-10-oxo-12(Z),15(Z)-octadecadienoic acid, an alpha-ketol derivative of linolenic acid, which is formed via 9-hydroperoxy linolenic acid. Synthesized FIF showed flower-inducing activity after incubation with NE (factor C activity) equivalent to that formed in the stressed Lemna. Jasmonic acid and 13-hydroxy-12-oxo-9(Z),15(Z)-octadecadienoic acid (12,13-alpha-ketol linolenic acid), both of which are formed via 13-hydroperoxide of linolenic acid and all other derivatives of FIF synthesized by chemical and enzymatic processes failed to show the factor C activity. These results suggest that the molecular structure of FIF is very specific for the factor C activity.
Yokoyama
M
M
Basic Res. Center, Shiseido Co., Ltd., Yokohama, Japan.
Yamaguchi
S
S
Inomata
S
S
Komatsu
K
K
Yoshida
S
S
Iida
T
T
Yokokawa
Y
Y
Yamaguchi
M
M
Kaihara
S
S
Takimoto
A
A
D005231:Fatty Acids, Unsaturated / Q000737:chemistry / Q000378:metabolism* / Q000494:pharmacology; D006358:Hot Temperature; D019684:Magnoliopsida / Q000187:drug effects / Q000254:growth & development*; D009638:Norepinephrine / Q000737:chemistry / Q000494:pharmacology; D009997:Osmotic Pressure; D018514:Plant Structures / Q000187:drug effects / Q000254:growth & development*; D013329:Structure-Activity Relationship; D014867:Water / Q000502:physiology; D017962:alpha-Linolenic Acid / Q000031:analogs & derivatives* / Q000737:chemistry / Q000378:metabolism* / Q000494:pharmacology
C408092:9-hydroxy-10-oxo-12,15-octadecadienoic acid; D005231:Fatty Acids, Unsaturated; D014867:Water; D017962:alpha-Linolenic Acid; D009638:Norepinephrine