scholarly journals Synthesis of New Abscisic Acid (ABA) Analogs Possessing a Geometrically Rigid Cyclized Side Chain

1992 ◽  
Vol 56 (4) ◽  
pp. 624-629 ◽  
Author(s):  
Bum-Tae Kim ◽  
Tadao Asami ◽  
Kensuke Morita ◽  
Chang-Ho Soh ◽  
Noboru Murofushi ◽  
...  
Keyword(s):  
Abscisic Acid ◽  
Side Chain ◽  
Aba Analogs

scholarly journals Abscisic acid analogs with a geometrically rigid conjugated acid side-chain.

1986 ◽  
Vol 50 (4) ◽  
pp. 1097-1100 ◽  
Author(s):  
S. C. CHEN ◽  
J. M. MACTAGGART
Keyword(s):  
Abscisic Acid ◽  
Side Chain

The effect of abscisic acid and abscisic acid metabolites on the germination of cress seed

1992 ◽  
Vol 70 (8) ◽  
pp. 1550-1555 ◽  
Author(s):  
L. V. Gusta ◽  
B. Ewan ◽  
M. J. T. Reaney ◽  
S. R. Abrams
Keyword(s):  
Abscisic Acid ◽  
Seed Germination ◽  
Optical Isomers ◽  
Phaseic Acid ◽  
Naturally Occurring ◽  
Maximum Inhibition ◽  
Cress Seed ◽  
Acid Metabolites ◽  
Aba Analogs ◽  
Optically Pure

Optical isomers of abscisic acid (ABA) and racemic mixtures of both abscisic acid and abscisic acid metabolites were studied to determine their effects on the emergence of root primordia and cotyledons from cress seed. The relative emergence sensitivity of cress seed to the racemic compounds was (±)-ABA aldehyde ≥ (±)-ABA alcohol > (±)-ABA > (±)7′-hydroxy ABA > (±)-phaseic acid. Thus ABA and ABA precursors were effective inhibitors whereas the ABA catabolites, phaseic acid, and 7′-hydroxy ABA had little or no effect on germination. The naturally occurring optically pure enantiomer (+)ABA was a more potent germination inhibitor than synthetic (−)-ABA. An ABA analog, 2′,3′-cis dihydro ABA (DHABA), that is not metabolized to phaseic acid was also studied for inhibitory activity. Although optically pure DHABA has the same configuration at C-1 as (+)-ABA, it was less inhibitory than (+)-ABA and its (−) enantiomer was inactive. The pattern of activity observed in treatments with the enantiomers of DHABA indicates that the configuration at C-1′ is important for maximum inhibition of cress seed germination. It also suggests that in contrast to monocot seeds, the formation of phaseic acid is not required for the inhibition of cress seed germination. Key words: abscisic acid, phaseic acid, ABA alcohol, ABA aldehyde, 7′OHABA, germination, ABA analogs.

scholarly journals Evaluation of Abscisic Acid Analogs as Holding Agents for Bedding Plant Seedlings

2006 ◽  
Vol 16 (1) ◽  
pp. 71-77 ◽  
Author(s):  
Nirmala Sharma ◽  
Doug R. Waterer ◽  
Suzanne R. Abrams
Keyword(s):  
Abscisic Acid ◽  
Methyl Ester ◽  
Moisture Loss ◽  
Dependent Manner ◽  
Negative Effects ◽  
Aesthetic Quality ◽  
Bedding Plant ◽  
Aba Analogs ◽  
Term Performance ◽  
Plant Seedlings

The marketing period of nursery-raised bedding plant seedlings is limited by the loss of aesthetic quality associated with undesirable growth and/or excess moisture loss during storage and handling. Long-lasting synthetic analogs of abscisic acid (ABA) (8′-methylene ABA methyl ester and 8′-acetylene ABA methyl ester) were evaluated for their potential use in controlling growth and extending the marketing period of seedlings of tomato (Lycopersicon esculentum), snapdragon (Antirrhinum majus), and nasturtium (Tropelaum majus). ABA analogs, applied as root-dips, slowed moisture use and reduced seedling growth in a dosage-dependent manner with no significant phytotoxic effects over the short term. The nature and duration of the responses of the three test crops to the ABA analog treatments were similar. ABA analogs were more effective at reducing moisture use by tomato seedlings than regular ABA and also had fewer negative effects on plant appearance. Before ABA analogs can be recommended for commercial-scale use, their impact on long-term performance needs to be determined, along with an evaluation of their cost and safety relative to other plant growth retardants.

3’-(Phenyl alkynyl) Analogs of Abscisic Acid: Two Step Synthesis of Potent ABA Antagonists

2021 ◽  
Author(s):  
Naveen Diddi ◽  
Leon Lai ◽  
Benjamin P Brookbank ◽  
Saad Hussain ◽  
Eiji Nambara ◽  
...  
Keyword(s):  
Abscisic Acid ◽  
Biological Testing ◽  
New Class ◽  
Rigid Framework ◽  
Aba Analogs

We report here the synthesis and biological testing of 3’-phenyl alkynyl abscisic ABA analogs, a new class of potent ABA antagonists. These ABA analogs incorporate a rigid framework of eight...

Effects of abscisic acid (ABA) and ABA analogs on freezing tolerance, low-temperature growth, and flowering in rapeseed

1994 ◽  
Vol 13 (4) ◽  
pp. 235-241 ◽  
Author(s):  
Ronald W. Wilen ◽  
Lawrence V. Gusta ◽  
Bo Lei ◽  
Suzanne R. Abrams ◽  
Bruce E. Ewan
Keyword(s):  
Abscisic Acid ◽  
Low Temperature ◽  
Freezing Tolerance ◽  
Temperature Growth ◽  
Low Temperature Growth ◽  
Aba Analogs

scholarly journals Photostable Abscisic Acid Agonists with a Geometrically Rigid Cyclized Side Chain

2022 ◽  
Author(s):  
Jun Takeuchi ◽  
Saya Mimura ◽  
Toshiyuki Ohnishi ◽  
Yasushi Todoroki
Keyword(s):  
Abscisic Acid ◽  
Side Chain

Insights into the in Vitro and in Vivo SAR of Abscisic Acid - Exploring Unprecedented Variations of the Side Chain via Cross-Coupling-Mediated Syntheses

2018 ◽  
Vol 2018 (12) ◽  
pp. 1403-1415 ◽  
Author(s):  
Jens Frackenpohl ◽  
Erwin Grill ◽  
Guido Bojack ◽  
Rachel Baltz ◽  
Marco Busch ◽  
...  
Keyword(s):  
Abscisic Acid ◽  
Cross Coupling ◽  
Side Chain

Endogenous biosynthetic precursors of (+)-abscisic acid. VII. The 1′,4′-trans-diol is formed from ABA, it is not a precursor

1998 ◽  
Vol 25 (6) ◽  
pp. 729 ◽  
Author(s):  
B. V. Milborrow ◽  
H.-S. Lee
Keyword(s):  
Abscisic Acid ◽  
Mung Bean ◽  
Cold Trap ◽  
Hydroxyl Group ◽  
Side Chain ◽  
Plant Tissues ◽  
Bean Seedling ◽  
Avocado Fruit ◽  
In Trans ◽  
Reducing Potential

[14C]ABA fed to avocado fruit is known to be converted into the 1′,4′-trans-diol and [14C]1′,4′-trans-diol has been shown to be converted into ABA by several plant tissues. As a ‘cold trap’of trans-diol becomes labelled with 14C when [14C]mevalonate is converted into ABA, the trans-diol has been suggested to be the immediate precursor of ABA. This proposal has now been tested by feeding [5-14C,5-3H2]mevalonolactone to unripe avocado fruit and measuring the 3H :14C ratio in the ABA and in the 1′,4′-trans-diol isolated from the fruit after 16 h. Little labelled diol was present unless a ‘cold trap’ of unlabelled 1,4-trans-diol was added with the mevalonate. One 3H atom, derived from those at C-5 of mevalonate, would be expected at C-4′ of the diol, adjacent to the hydroxyl group, and another at C-5 of the side chain of the diol if the diol were a precursor of ABA (3H:14C ratio of 2:3). However, if the 4′-hydroxyl group had been oxidised to a ketone to form ABA, then the 3H atom at C-4′ of the diol would have been lost and the 3H:14C ratio would be expected to be 1:3. The normalised 3H : 14C ratios of ABA and 1′,4′-trans-diol biosynthesised from [14C,5-3H2]mevalonate were 0.915:3 and 0.844:3 respectively and after oxidation of the diol to ABA with MnO2 the ratio was 0.869:3 i.e. there was no 3H at C-4′ of the diol. These ratios are as expected for the trans-diol if it had been formed by reduction of ABA. This, and the absence of labelled diol in the fruit unless a ‘cold trap’was added, establishes that the 1′,4′-trans-diol is formed from ABA and it is not a precursor. The formation of the diols from newly synthesised labelled ABA in cell-free systems can be attributed to the addition to the homogenate of compounds with strong reducing potential. NADPH2+ (8.4 nmol) added to a mung bean seedling homogenate caused the reduction of (±)-[14C]ABA (0.37 nmol, 22.5 µCi/mol) to trans-diol (1189 dpm) whereas with NADP+ only 338 dpm were present in trans-diol. Glutathione (46 nmol) caused the formation of 1214 dpm while oxidised glutathione produced 638 dpm. Less 1′,4′-cis-diol was formed.

scholarly journals The conformation of abscisic acid by n.m.r. and a revision of the proposed mechanism for cyclization during its biosynthesis

1984 ◽  
Vol 220 (1) ◽  
pp. 325-332 ◽  
Author(s):  
B V Milborrow
Keyword(s):  
Abscisic Acid ◽  
Hydrogen Atom ◽  
Pulse Sequence ◽  
Chair Conformation ◽  
Crystalline Form ◽  
Side Chain ◽  
Hydrogen Atoms ◽  
Methyl Group ◽  
Nuclear Overhauser Enhancement ◽  
Nuclear Overhauser

The n.m.r. spectrum of abscisic acid (ABA) formed from [1,2-13C2]acetate by the fungus Cercospora rosicola shows 13C-13C coupling between C-6′ (41.7 p.p.m.; 36 Hz) and the downfield 6′-methyl group (6′-Me) (24.3 p.p.m, 36 Hz). This 6′-Me, therefore, is derived from C-3′ of mevalonate [Bennett, Norman & Maier (1981) Phytochemistry 20, 2343-2344]. An i.n.e.p.t. (insensitive nuclei enhanced by polarization transfer) pulse sequence demonstrated that the downfield 13C signal is produced by the 6′-Me that gives rise to the upfield 1H 6′-Me signal (23.1 d). The absolute configuration of this, the equatorial 6′-Me group, was determined as 6′-pro-R by decoupling and n.O.e. (nuclear-Overhauser-enhancement) experiments at 300 MHz using ABA, ABA in which the axial 6′-pro-S 5′-hydrogen atom had been exchanged with 2H in NaO2H and the 1′,4′-cis- and 1′,4′-trans-diols formed from these samples. The configuration at C-1′ and at C-6′ are now compatible with a chair-folded intermediate during cyclization, as proposed for beta- and epsilon-rings of carotenoids. ABA in solution exists, as in the crystalline form, with the ring in a pseudo-chair conformation. The side chain is axial and the C-3 Me and the C-5 hydrogen atoms are predominantly cis(Z).

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