Oxidation of the 8′-position of a biologically active abscisic acid analogue

Par Conseil national de recherches du Canada

DOI	Trouver le DOI : https://doi.org/10.1016/S0031-9422(00)90687-3
Auteur	Rechercher : Lamb, Nancy¹; Rechercher : Shaw, Angela C.¹; Rechercher : Abrams, Suzanne R.¹; Rechercher : Reaney, Martin J.T.; Rechercher : Ewan, Bruce; Rechercher : Robertson, Albert J.; Rechercher : Gusta, Lawrence V.
Affiliation	Conseil national de recherches du Canada. Institut de biotechnologie des plantes du CNRC
Format	Texte, Article
Résumé	e metabolism of a biologically active abscisic acid (ABA) analogue, ( + )-( l’SJ’S)-2’,3’-dihydroabscisic acid [( +)-4-(1E,3Z)-(4S,5S)-4-(4-carboxy-3-methyl-1,3-butadienyl)-4-hydroxy-3,3,5-trimethyl~clohexanone], which cannot form phase & acid was studied in a cell suspension culture of bromegrass (Bromus inermis). The analogue induced freezing tolerance in bromegrass cells similar to (S)-( + )-ABA and was oxidized to (l’S,2’S)-8’-hydroxy-2’,3’-dihydroabscisic acid [4-(1E,3Z)-(3R,4S,5S)-4-(4-carboxy-3-methyl-l,3-butadienyl)-~hydroxy-3-hydroxymethyl-3,5-dimethylcyclohexanone]. The enantiomer ( -)-(l’RJ’R)- 2’,3’dihydroabscisic acid, which was inactive in inducing freezing tolerance, was converted to two metabolites, viz., the corresponding enantiomeric (l’RJ’R)-8’-hydroxy-2’,3’-dihydroabscisic acid [4-(1E,3Z~3S,4R,5R)-4-(4_carboxy-3-methyl-l,3-butadi~yl)~-hydroxy-3-hydroxymethyl-3,5-dimethylcyclohexanone] and reduction product (-)-l-(lE,3Z)-( lR,4S,6R)-1-(4-carboxy-3-methyl-1,3-butadienyl)-2,2,6-trimethylcyclohexan-l+diol. Both enantiomers of the analogue were transformed to the glucose esters. The structures of the metabolites were established by both spectroscopic analyses and chemical syntheses. The metabolite 8’-hydroxy-2’,3’-hydroxyabscisic acid is a cyclohexanone analogue of 8’-hydroxyabscisic acid, the transient oxidation product in the metabolism of ABA to phaseic acid. Like phaseic acid, the racemic form of 8’-hydroxy-2’,3’-dihydroabscisic acid was inactive in inducing freezing tolerance in bromegrass cells, suggesting that ABA and (+)-(l’&?‘S)-2’,3’-dihydroabscisic acid were the active compounds.
Date de publication	1993-11
Maison d’édition	Elsevier
Dans	Phytochemistry 34, nº 4 (novembre 1993) : 905–917.
Langue	anglais
Publications évaluées par des pairs	Oui
Identificateur	S0031942200906873 NRCC-35892
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Identificateur de l’enregistrement	5534e772-c0d2-4431-87fd-2184eab74af7
Enregistrement créé	2023-11-06
Enregistrement modifié	2023-11-06

Date de modification :: 2024-07-01