Synthesis of (+)-, (−)- and (±)-7′-hydroxyabscisic acid

Nelson, L. A. K.; Shaw, A.; Abrams, Suzanne R.

doi:10.1016/s0040-4020(01)86392-4

Cited by 36 publications

(17 citation statements)

References 25 publications

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“…ABA was purchased from Lomon Bio Technology [(S)-ABA; http://www.lomonbio.com]. Other ABA derivatives were synthesized as described in the cited literature: xanthoxin (Kuba et al, 2002), ABA alcohol and ABA aldehyde (Rose et al, 1992; ABA aldehyde was prepared immediately prior to use by oxidation of ABA alcohol), 7#-OH ABA (Nelson et al, 1991), DPA and ABA GE (Zaharia et al, 2005a), neoPA (Zhou et al, 2004), and the tetralone ABA derivatives (Nyangulu et al, 2006). PA was obtained by biotransformation of (+)-ABA in Black Mexican Sweet corn (Zea mays) as described by Balsevich et al (1994).…”

Section: Chemicalsmentioning

confidence: 99%

Action of Natural Abscisic Acid Precursors and Catabolites on Abscisic Acid Receptor Complexes

et al. 2011

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The phytohormone abscisic acid (ABA) regulates stress responses and controls numerous aspects of plant growth and development. Biosynthetic precursors and catabolites of ABA have been shown to trigger ABA responses in physiological assays, but it is not clear whether these are intrinsically active or whether they are converted into ABA in planta. In this study, we analyzed the effect of ABA precursors, conjugates, and catabolites on hormone signaling in Arabidopsis (Arabidopsis thaliana). The compounds were also tested in vitro for their ability to regulate the phosphatase moiety of ABA receptor complexes consisting of the protein phosphatase 2C ABI2 and the coreceptors RCAR1/PYL9, RCAR3/PYL8, and RCAR11/ PYR1. Using mutants defective in ABA biosynthesis, we show that the physiological activity associated with ABA precursors derives predominantly from their bioconversion to ABA. The ABA glucose ester conjugate, which is the most widespread storage form of ABA, showed weak ABA-like activity in germination assays and in triggering ABA signaling in protoplasts. The ABA conjugate and precursors showed negligible activity as a regulatory ligand of the ABI2/RCAR receptor complexes. The majority of ABA catabolites were inactive in our assays. To analyze the chemically unstable 8#-and 9#-hydroxylated ABA catabolites, we used stable tetralone derivatives of these compounds, which did trigger selective ABA responses. ABA synthetic analogs exhibited differential activity as regulatory ligands of different ABA receptor complexes in vitro. The data show that ABA precursors, catabolites, and conjugates have limited intrinsic bioactivity and that both natural and synthetic ABA-related compounds can be used to probe the structural requirements of ABA ligand-receptor interactions.

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Section: Chemicalsmentioning

confidence: 99%

Action of Natural Abscisic Acid Precursors and Catabolites on Abscisic Acid Receptor Complexes

et al. 2011

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“…The following chemicals were prepared as described previously: (ϩ)-ABA (Balsevich et al, 1994); [8Ј,9Ј-2 H 6 ]ABA (Lamb et al, 1996); [5,8Ј-2 H 4 ]ABA ; [8Ј-2 H 3 ]ABA (Rose et al, 1997); S-(ϩ)-7Ј-OH ABA (Nelson et al, 1991); and (Ϫ)-PA (Balsevich et al, 1994). (ϩ)-9Ј-OH ABA, plus its enantiomer, and (2Z,4E)-5-[(1S,5S,8S)-8-hydroxy-1,5-dimethyl-3-oxo-6-oxa-bicyclo[3.2.1]oct-8-yl]-3-methyl-penta-2,4-dienoic acid ((ϩ)-neoPA), plus its enantiomer, were synthesized.…”

Section: Aba Aba Catabolites and Deuterium-labeled Analogsmentioning

confidence: 99%

A New Abscisic Acid Catabolic Pathway

et al. 2004

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We report the discovery of a new hydroxylated abscisic acid (ABA) metabolite, found in the course of a mass spectrometric study of ABA metabolism in Brassica napus siliques. This metabolite reveals a previously unknown catabolic pathway for ABA in which the 9-methyl group of ABA is oxidized. Analogs of ()-ABA deuterated at the 8-carbon atom and at both the 8-and 9-carbon atoms were fed to green siliques, and extracts containing the deuterated oxidized metabolites were analyzed to determine the position of ABA hydroxylation. The results indicated that hydroxylation of ABA had occurred at the 9-methyl group, as well as at the 7-and 8-methyl groups. The chromatographic characteristics and mass spectral fragmentation patterns of the new ABA metabolite were compared with those of synthetic 9-hydroxy ABA (9-OH ABA), in both open and cyclized forms. The new compound isolated from plant extracts was identified as the cyclized form of 9-OH ABA, which we have named neophaseic acid (neoPA). The proton nuclear magnetic resonance spectrum of pure neoPA isolated from immature seeds of B. napus was identical to that of the authentic synthetic compound. ABA and neoPA levels were high in young seeds and lower in older seeds. The open form (2Z,4E)-5-[(1R,6S)-1-Hydroxy-6-hydroxymethyl-2,6-dimethyl-4-oxo-cyclohex-2-enyl]-3-methyl-penta-2,4-dienoic acid, but not neoPA, exhibited ABA-like bioactivity in inhibiting Arabidopsis seed germination and in inducing gene expression in B. napus microspore-derived embryos. NeoPA was also detected in fruits of orange (Citrus sinensis) and tomato (Lycopersicon esculentum), in Arabidopsis, and in chickpea (Cicer arietinum), as well as in drought-stressed barley (Hordeum vulgare) and B. napus seedlings.

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“…(ϩ)-ABA, (Ϫ)-ABA, and their metabolites were obtained as described previously: (ϩ)-ABA, (Ϫ)-ABA, (Ϫ)-PA, 8Ј-hydroxy-ABA (Zou et al, 1995), DPA (according to the method of Zeevaart and Milborrow, 1976); (Ϯ)-7Ј-hydroxy-ABA (Nelson et al, 1991); (Ϯ)-ABA trans-1Ј,4Ј-diol and (Ϯ)-ABA cis-1Ј, 4Ј-diol (Balsevich et al, 1996). Additional (ϩ)-ABA was generously provided by Y. Kamuro (BAL Planning Co., Hanaike, Japan).…”

Section: Chemicalsmentioning

confidence: 99%