title: Stress-induced factor involved in flower formation of Lemna is an alpha-ketol derivative of linolenic acid.
abstract: 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.
authors.affiliation: Basic Res. Center, Shiseido Co., Ltd., Yokohama, Japan.
authors.forename: M
authors.initials: M
authors.lastname: Yokoyama
authors.forename: S
authors.initials: S
authors.lastname: Yamaguchi
authors.forename: S
authors.initials: S
authors.lastname: Inomata
authors.forename: K
authors.initials: K
authors.lastname: Komatsu
authors.forename: S
authors.initials: S
authors.lastname: Yoshida
authors.forename: T
authors.initials: T
authors.lastname: Iida
authors.forename: Y
authors.initials: Y
authors.lastname: Yokokawa
authors.forename: M
authors.initials: M
authors.lastname: Yamaguchi
authors.forename: S
authors.initials: S
authors.lastname: Kaihara
authors.forename: A
authors.initials: A
authors.lastname: Takimoto
mesh_terms: 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
chemical_list: C408092:9-hydroxy-10-oxo-12,15-octadecadienoic acid; D005231:Fatty Acids, Unsaturated; D014867:Water; D017962:alpha-Linolenic Acid; D009638:Norepinephrine