Identification of a component that induces flowering of Lemna among the reaction products of alpha-ketol linolenic acid (FIF) and norepinephrine.
A stress-induced fatty acid [FIF; 9-hydroxy-10-oxo-12(Z),15(Z)-octadecadienoic acid] incubated with (-)-norepinephrine (NE) strongly induces flower formation in Lemna paucicostata [Yokoyama et al. (2000), Plant Cell Physiol. 41: 110). The increase of flower-inducing activity was well correlated with the decrease in FIF in the incubation mixture, and the reaction proceeded rapidly at higher pH. We detected small amounts of many active components in the mixture after incubation by HPLC analysis. In this study, two major components, named FN1 and FN2, of the reaction mixture were isolated, and their absolute stereostructures were determined. FN1 showed a strong flower-inducing activity and was identified as a tricyclic alpha-ketol fatty acid, 9(R)-11-[(2'R,8'R,10'S,11'S)-2',8'-dihydroxy-7'-oxo-11'-[(Z)-2-pentenyl]-9'-oxa-4'-azatricyclo[6.3.1.0(1.5)]dodec- 5'en-10'-yl]-9-hydroxy-10-oxoundecanoic acid [corrected]. FN2, the C-9 epimer of FN1, showed no flower-inducing activity. The absolute stereostructure of FIF was also determined by a modification of Mosher's method. The 9-hydroxyl group was found to be predominantly 9R, with an enantiomeric excess of 40% (70% 9R and 30% 9S). FN1 was derived from 9R-type FIF and FN2 from 9S-type FIF. Various catecholamines and related substances were investigated for the ability to develop flower-inducing activity upon incubation with FIF. The essential structures were catechol and ethylamine groups (dopamine).
Yamaguchi
S
S
Basic Research Center, Shiseido Co. Ltd., Tsuzuki-ku, Yokohama, 224-8558 Japan.
Yokoyama
M
M
Iida
T
T
Okai
M
M
Tanaka
O
O
Takimoto
A
A
D002395:Catecholamines / Q000378:metabolism; D002851:Chromatography, High Pressure Liquid; D005021:Ethylamines / Q000378:metabolism; D006863:Hydrogen-Ion Concentration; D009682:Magnetic Resonance Spectroscopy; D019684:Magnoliopsida / Q000737:chemistry* / Q000254:growth & development; D015394:Molecular Structure; D009638:Norepinephrine / Q000378:metabolism; D018547:Plant Stems / Q000737:chemistry / Q000254:growth & development; D013237:Stereoisomerism; D017962:alpha-Linolenic Acid / Q000031:analogs & derivatives* / Q000737:chemistry* / Q000378:metabolism*
C454864:9(R)-11-((2'S,8'S,10'S,11'R)-2',8'-dihydroxy-7'-oxo-11'-((Z)-2-pentenyl)-9'-oxa-4'-azatricyclo (6.3.1.0(1.5))dodec-5'en-10'-yl)-9-hydroxy-10-oxoundecanoic acid, 9 epimer; C454863:9(R)-11-((2'S,8'S,10'S,11'R)-2',8'-dihydroxy-7'-oxo-11'-((Z)-2-pentenyl)-9'-oxa-4'-azatricyclo(6.3.1.0(1.5))dodec- 5'en-10'-yl)-9-hydroxy-10-oxoundecanoic acid; C408092:9-hydroxy-10-oxo-12,15-octadecadienoic acid; D002395:Catecholamines; D005021:Ethylamines; D017962:alpha-Linolenic Acid; D009638:Norepinephrine; C041564:ethylamine