Metabolism of (+)- and (−)-abscisic acid by somatic embryo suspension cultures of white spruce

Dunstan, David I.; Bock, Cheryl A.; Abrams, Garth D.; Abrams, Suzanne R.

doi:10.1016/0031-9422(92)83085-d

Cited by 65 publications

(37 citation statements)

References 15 publications

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“…1) was obtained by preparative resolution of the racemic methyl ester on a chiral column, followed by hydrolysis of the (+) enantiomer to the free acid, as described by Dunstan et al (1992). (-)TA, the naturally occurring enantiomer (Fig.…”

Section: Preparation Of (+)-Aba and Metabolitesmentioning

confidence: 99%

Induction of Lipid and Oleosin Biosynthesis by (+)-Abscisic Acid and Its Metabolites in Microspore-Derived Embryos of Brassica napus L.cv Reston (Biological Responses in the Presence of 8[prime]-Hydroxyabscisic Acid)

et al. 1995

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Section: Preparation Of (+)-Aba and Metabolitesmentioning

confidence: 99%

Induction of Lipid and Oleosin Biosynthesis by (+)-Abscisic Acid and Its Metabolites in Microspore-Derived Embryos of Brassica napus L.cv Reston (Biological Responses in the Presence of 8[prime]-Hydroxyabscisic Acid)

et al. 1995

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“…The optically pure ABA isomers were prepared by resolution of the methyl ester of racemic ABA and then hydrolyzed to the acid as described by Dunstan et al (1992).…”

Section: Aba Treatments Of Developing Prematurely Driied and Hydratmentioning

confidence: 99%

Vicilin and Napin Storage-Protein Gene Promoters Are Responsive to Abscisic Acid in Developing Transgenic Tobacco Seed but Lose Sensitivity following Premature Desiccation

1996

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“…This column, which contains a chiral stationary phase, had previously been used to resolve racemic ABA methyl ester (19). The results are summarized in Table 2.…”

Section: Lc Of Acetosugar Estersmentioning

confidence: 99%

Preparation and analysis of some acetosugar esters of abscisic acid and derivatives

Balsevich¹,

Bishop²,

Jacques³

et al. 1996

Can. J. Chem.

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Racemic abscisic acid (ABA), the cis and trans l', 4'-diols (ABA diols) derived from ABA by reduction of the 4' ketone, and the corresponding 4'-0-acetates were converted into various acetosugar esters by reaction of their cesium salts with the I-chloroacetosugars derived from glucose, galactose, lactose, and maltose. Analytical separations of the acetosugar esters using high-performance liquid chromatography (LC) on reverse-phase columns were developed. Continuous flow secondary ion mass spectra (CFSIMS) of the various acetosugar esters were obtained and an LCICFSIMS protocol employing multiple reaction monitoring was used to detect ABA acetoglucose ester in an acetylated extract obtained from plant cells that had been treated with ABA.Key words: abscisic acid, acetosugar esters, synthesis, chromatography, mass spectrometry. Fig. 1) is a plant growth regulator that has also been implicated in a variety of stress-related responses (1). Several metabolites of endogenous and exogenously added ABA have been isolated and identified, including the reduction products, cis and trnrzs ABA l', 4'-diols (2-5); the oxidized derivative, phaseic acid (6-8); and the glucose esters (P-D-glucose, C-1-linked) of ABA and the aformentioned compounds (Fig. 1) (9-12). There has also been a report of the detection of a maltose ester of ABA (13).We were interested in following ABA metabolism, and in developing analytical methods to facilitate our studies; in particular, we sought to extend the utility of liquid chromatography-continuous flow secondary ion mass spectrometry (LC/ CFSIMS), which we had earlier used to detect ABA glucose ester in a plant extract (14), to other ABA-derived conjugates, which we felt were potential metabolites. To achieve these objectives, samples of potential metabolites or suitable derivatives thereof were required as standards.Previously, ABA glucose ester (P anomer) had been prepared by reaction of ABA (cesium or triethyl ammonium salt) with a-bromoacetoglucose followed by deacetylation of the intermediate acetoglucose ester with an enzyme preparation derived from sunflower seeds (Helianthus arirzus) (15, 16). ABA diols had been prepared by sodium borohydride reduction of ABA methyl ester, which yielded a mixture rich in both the 1', 4'-cis and -trans diols (17).To further extend earlier synthetic efforts as well as the use of LCICFSIMS in analysis of metabolite mixtures, we report here the preparation of various acetosugar derivatives of ABA (and deuterated ABA) and the diols, and acetylated diols of ABA, and the development of LC and LCICFSIMS protocols using these derivatives. The acetosugar derivatives were easily prepared and possessed good stability. Some deuterated analogs were prepared as an aid in assigning fragments in the mass spectrum and for potential use as internal standards. As an example of the utility of the developed protocol, a sample plant extract was analyzed.

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Metabolism of (+)- and (−)-abscisic acid by somatic embryo suspension cultures of white spruce

Cited by 65 publications

References 15 publications

Induction of Lipid and Oleosin Biosynthesis by (+)-Abscisic Acid and Its Metabolites in Microspore-Derived Embryos of Brassica napus L.cv Reston (Biological Responses in the Presence of 8[prime]-Hydroxyabscisic Acid)

Induction of Lipid and Oleosin Biosynthesis by (+)-Abscisic Acid and Its Metabolites in Microspore-Derived Embryos of Brassica napus L.cv Reston (Biological Responses in the Presence of 8[prime]-Hydroxyabscisic Acid)

Vicilin and Napin Storage-Protein Gene Promoters Are Responsive to Abscisic Acid in Developing Transgenic Tobacco Seed but Lose Sensitivity following Premature Desiccation

Preparation and analysis of some acetosugar esters of abscisic acid and derivatives

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