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1.
Org Biomol Chem ; 19(13): 2978-2985, 2021 04 07.
Article in English | MEDLINE | ID: mdl-33729254

ABSTRACT

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 carbon atoms attached at the 3'-carbon atom of ABA that prevents folding of the ABA analog-bound receptor required for ABA signalling. The two-step synthesis is based upon the optimized conversion of natural (S)-ABA to 3'-iodo ABA which can be coupled to phenyl acetylenes using Sonogashira conditions, or to styryl compounds through Suzuki chemistry. The parent 3'-(phenyl alkynyl) ABA analog 7 was obtained in 29% yield, 74% yield based on recovered starting material. In a lentil seed germination assay, compound 7 was found to have more potent activity than other known 3'-substituted ABA antagonists to date. In a structure activity study parasubstituted phenyl alkynyl analogs had comparable activity to the analog 7 while the 3'-styryl ABA 18 was only slightly less active. Analog 7 overcame ABA inhibition of germination and seedling growth in a wide range of mono and dicot plant species, including canola, lentil, soybean, rice, wheat, barley, cannabis and canary seed. 3'-(Phenyl alkynyl) ABA analogs have numerous potential practical agricultural applications including promoting ripening of crops, dormancy breaking of seeds and woody perennials, as well as promoting seed germination, and growth under stress conditions as demonstrated in this report.


Subject(s)
Abscisic Acid/pharmacology , Alkynes/pharmacology , Plant Growth Regulators/pharmacology , Plants/drug effects , Abscisic Acid/chemical synthesis , Abscisic Acid/chemistry , Alkynes/chemical synthesis , Alkynes/chemistry , Germination/drug effects , Molecular Structure , Plant Growth Regulators/chemical synthesis , Plant Growth Regulators/chemistry , Plants/metabolism , Seeds/drug effects , Signal Transduction/drug effects
2.
Molecules ; 22(12)2017 Dec 15.
Article in English | MEDLINE | ID: mdl-29244719

ABSTRACT

2',3'-iso-Benzoabscisic acid (iso-PhABA), an excellent selective abscisic acid (ABA) analog, was developed in our previous work. In order to find its more structure-activity information, some structural modifications were completed in this paper, including the substitution of phenyl ring and replacing the ring with heterocycles. Thus, 16 novel analogs of iso-PhABA were synthesized and screened with three bioassays, Arabidopsis and lettuce seed germination and rice seedling elongation. Some of them, i.e., 2',3'-iso-pyridoabscisic acid (iso-PyABA) and 2',3'-iso-franoabscisic acid (iso-FrABA), displayed good bioactivities that closed to iso-PhABA and natural (+)-ABA. Some others, for instance, substituted-iso-PhABA, exhibited certain selectivity to different physiological process when compared to iso-PhABA or (+)-ABA. These analogs not only provided new candidates of ABA-like synthetic plant growth regulators (PGRs) for practical application, but also new potential selective agonist/antagonist for probing the specific function of ABA receptors.


Subject(s)
Abscisic Acid/analogs & derivatives , Abscisic Acid/chemical synthesis , Abscisic Acid/metabolism , Arabidopsis/metabolism , Germination , Lactuca/metabolism , Molecular Structure , Oryza/metabolism , Plant Growth Regulators/chemical synthesis , Plant Growth Regulators/metabolism , Seedlings/metabolism , Seeds/metabolism
3.
Sci Rep ; 7: 43863, 2017 03 08.
Article in English | MEDLINE | ID: mdl-28272449

ABSTRACT

The phytohormone abscisic acid (ABA) plays a crucial role in mediating plant growth and development by recruiting genetically redundant ABA receptors. To overcome its oxidation inactivation, we developed a novel ABA analog named 2',3'-benzo-iso-ABA (iso-PhABA) and studied its function and structural characterization with A. thaliana ABA receptors. The (+)-iso-PhABA form showed much higher ABA-like activities than (+)-ABA including inhibitory effects on the seed germination of lettuce and A. thaliana, wheat embryo germination and rice seedling elongation. The PP2C (protein phosphatases 2C) activity assay showed that (+)-iso-PhABA acted as a potent and selective ABA receptor agonist, which is preferred to PYL10. In some cases, (-)-iso-PhABA showed moderate to high activity for the PYL protein inhibiting PP2C activity, suggesting different mechanisms of action of iso-PhABA and ABA. The complex crystal structure of iso-PhABA with PYL10 was determined and elucidated successfully, revealing that (+)-iso-PhABA was better coordinated in the same binding pocket compared to (+)-ABA. Moreover, the detailed interaction network of iso-PhABA/PYL10 was disclosed and involves hydrogen bonds and multiple hydrophobic interactions that provide a robust framework for the design of novel ABA receptor agonists/antagonists.


Subject(s)
Abscisic Acid/chemical synthesis , Abscisic Acid/pharmacology , Drug Design , Models, Chemical , Abscisic Acid/chemistry , Arabidopsis/growth & development , Arabidopsis Proteins/agonists , Arabidopsis Proteins/chemistry , Arabidopsis Proteins/metabolism , Crystallography, X-Ray , Germination/drug effects , Lactuca/growth & development , Molecular Structure , Oryza/growth & development , Plant Growth Regulators/chemical synthesis , Plant Growth Regulators/chemistry , Plant Growth Regulators/pharmacology , Protein Phosphatase 2C/antagonists & inhibitors , Protein Phosphatase 2C/metabolism , Receptors, Cell Surface/agonists , Receptors, Cell Surface/chemistry , Receptors, Cell Surface/metabolism , Seedlings/drug effects , Seedlings/growth & development , Seeds/drug effects , Seeds/growth & development
4.
Bioorg Med Chem ; 23(18): 6210-7, 2015 Sep 15.
Article in English | MEDLINE | ID: mdl-26296912

ABSTRACT

cis-2,3-Cyclopropanated abscisic acid (cis-CpABA) has high photostability and good ABA-like activity. To further investigate its activity and action mechanism, 2S,3S-2,3-cyclopropanated ABA (3a) and 2R,3R-2,3-cyclopropanated ABA (3b) were synthesized. Bioassay showed that 3a displayed higher inhibitory activity in germination than that of 3b and ABA at the concentration of 3.0 µM, but 3a and 3b had much weaker inhibitory activity in inhibition seedling growth compared to ABA. The study of photostability revealed that 3a and 3b showed high stability under UV light exposure, which were 4 times and 3 times greater than (±)-ABA, respectively. Action mechanism study showed that 3a presented higher inhibition on phosphatase activity of HAB1 than 3b, although they all inferior to ABA. Molecular docking studies of 3a, 3b and ABA receptor PYL10 were agreement with the bioassay data and confirmed the importance of the configuration of the 2,3-cyclopropyl ABA analogs for their bioactivity in somewhat. This study provides a new approach for the design of ABA analogs, and the results validated structure-based design for this target class.


Subject(s)
Abscisic Acid/analogs & derivatives , Plant Growth Regulators/chemical synthesis , Abscisic Acid/chemical synthesis , Abscisic Acid/chemistry , Abscisic Acid/pharmacology , Arabidopsis/growth & development , Arabidopsis/metabolism , Arabidopsis Proteins/antagonists & inhibitors , Arabidopsis Proteins/genetics , Arabidopsis Proteins/metabolism , Binding Sites , Cyclopropanes/chemistry , Germination/drug effects , Molecular Docking Simulation , Monocyclic Sesquiterpenes , Phosphoprotein Phosphatases/antagonists & inhibitors , Phosphoprotein Phosphatases/genetics , Phosphoprotein Phosphatases/metabolism , Plant Growth Regulators/chemistry , Plant Growth Regulators/pharmacology , Protein Structure, Tertiary , Recombinant Proteins/biosynthesis , Recombinant Proteins/chemistry , Recombinant Proteins/isolation & purification , Seeds/growth & development
5.
Bioorg Med Chem Lett ; 25(11): 2438-41, 2015 Jun 01.
Article in English | MEDLINE | ID: mdl-25913114

ABSTRACT

2',3'-Benzoabscisic acid 4a is significantly more active than (±)-ABA and can be potentially used as a plant growth regulator for agriculture. In this study, six 4a analogs were designed and synthesized. Bioassay showed that 4a displayed greater activity than (±)-ABA and the six analogs produced less inhibition than 4a itself. Specially, some analogs displayed markedly different activities to different physiological and biochemical process, which were largely different from ABA and 4a. Compared to (±)-ABA, 4b and 4c were more effective germination inhibitors for lettuce, but less effective inhibitors for rice elongation. Five-membered analog 5 was higher or slightly weaker in inhibiting Arabidopsis seed germination and rice elongation, respectively, but at least 10 times less effective than (±)-ABA in lettuce seed germination. Dual acid 6 and alkyne acid 20 nearly produced no inhibitory activity for Arabidopsis seed germination, but displayed excellent activity in inhibiting rice seedling growth. The preference of the analogs to different physiology process indicated that they might provide a strategy to develop novel ABA agonists or antagonist and be used as probe to investigate the function of different ABA receptors.


Subject(s)
Abscisic Acid/analogs & derivatives , Abscisic Acid/chemical synthesis , Naphthalenes/chemical synthesis , Abscisic Acid/pharmacology , Arabidopsis/drug effects , Arabidopsis/growth & development , Biological Assay , Germination/drug effects , Lactuca/drug effects , Lactuca/growth & development , Molecular Structure , Naphthalenes/pharmacology , Oryza/drug effects , Oryza/growth & development , Seeds/drug effects , Seeds/growth & development
6.
Bioorg Med Chem ; 23(1): 22-32, 2015 Jan 01.
Article in English | MEDLINE | ID: mdl-25496807

ABSTRACT

The phytohormone abscisic acid (ABA), in addition to regulating physiological functions in plants, is also produced and released by several mammalian cell types, including human granulocytes, where it stimulates innate immune functions via an increase of the intracellular cAMP concentration ([cAMP]i). We synthesized several ABA analogs and evaluated the structure-activity relationship, by the systematical modification of selected regions of these analogs. The resulting molecules were tested for their ability to inhibit the ABA-induced increase of [cAMP]i in human granulocytes. The analogs with modified configurations at C-2' and C-3' abrogated the ABA-induced increase of the [cAMP]i and also inhibited several pro-inflammatory effects induced by exogenous ABA on granulocytes and monocytes. Accordingly, these analogs could be suitable as novel putative anti-inflammatory compounds.


Subject(s)
Abscisic Acid/analogs & derivatives , Abscisic Acid/pharmacology , Cyclic AMP/metabolism , Granulocytes/drug effects , Granulocytes/metabolism , Abscisic Acid/chemical synthesis , Abscisic Acid/chemistry , Humans , Intracellular Membranes/drug effects , Signal Transduction , Structure-Activity Relationship
7.
Nat Chem Biol ; 10(6): 477-82, 2014 Jun.
Article in English | MEDLINE | ID: mdl-24792952

ABSTRACT

The plant stress hormone abscisic acid (ABA) is critical for several abiotic stress responses. ABA signaling is normally repressed by group-A protein phosphatases 2C (PP2Cs), but stress-induced ABA binds Arabidopsis PYR/PYL/RCAR (PYL) receptors, which then bind and inhibit PP2Cs. X-ray structures of several receptor-ABA complexes revealed a tunnel above ABA's 3' ring CH that opens at the PP2C binding interface. Here, ABA analogs with sufficiently long 3' alkyl chains were predicted to traverse this tunnel and block PYL-PP2C interactions. To test this, a series of 3'-alkylsulfanyl ABAs were synthesized with different alkyl chain lengths. Physiological, biochemical and structural analyses revealed that a six-carbon alkyl substitution produced a potent ABA antagonist that was sufficiently active to block multiple stress-induced ABA responses in vivo. This study provides a new approach for the design of ABA analogs, and the results validated structure-based design for this target class.


Subject(s)
Abscisic Acid/analogs & derivatives , Arabidopsis Proteins/antagonists & inhibitors , Phosphoprotein Phosphatases/antagonists & inhibitors , Plant Growth Regulators , Abscisic Acid/chemical synthesis , Abscisic Acid/pharmacology , Arabidopsis/drug effects , Arabidopsis/genetics , Arabidopsis/metabolism , Arabidopsis Proteins/metabolism , Germination/drug effects , Lactuca/drug effects , Lactuca/metabolism , Models, Molecular , Phosphoprotein Phosphatases/metabolism , Plant Growth Regulators/chemical synthesis , Plant Growth Regulators/pharmacology , Plant Physiological Phenomena , Protein Binding , Raphanus/drug effects , Raphanus/metabolism , Seeds/drug effects , Seeds/metabolism , Structure-Activity Relationship
8.
Bioorg Med Chem ; 19(5): 1743-50, 2011 Mar 01.
Article in English | MEDLINE | ID: mdl-21310619

ABSTRACT

We prepared 19 amino acid conjugates of the plant hormone abscisic acid (ABA) and investigated their biological activity, enzymatic hydrolysis by a recombinant Arabidopsis amidohydrolases GST-ILR1 and GST-IAR3, and metabolic fate in rice seedlings. Different sets of ABA-amino acids induced ABA-like responses in different plants. Some ABA-amino acids, including some that were active in bioassays, were hydrolyzed by recombinant Arabidopsis GST-IAR3, although GST-ILR1 did not show hydrolysis activity for any of the ABA-amino acids. ABA-L-Ala, which was active in all the bioassays, an Arabidopsis seed germination, spinach seed germination, and rice seedling elongation assays, except in a lettuce seed germination assay and was hydrolyzed by GST-IAR3, was hydrolyzed to free ABA in rice seedlings. These findings suggest that some plant amidohydrolases hydrolyze some ABA-amino acid conjugates. Because our study indicates the possibility that different plants have hydrolyzing activity toward different ABA-amino acids, an ABA-amino acid may function as a species-selective pro-hormone of ABA.


Subject(s)
Abscisic Acid , Amino Acids , Abscisic Acid/chemical synthesis , Abscisic Acid/chemistry , Abscisic Acid/metabolism , Abscisic Acid/pharmacology , Amino Acids/chemical synthesis , Amino Acids/chemistry , Amino Acids/metabolism , Amino Acids/pharmacology , Arabidopsis Proteins/metabolism , Germination , Inhibitory Concentration 50 , Molecular Structure , Oryza/metabolism , Plant Growth Regulators/chemistry , Plant Growth Regulators/metabolism , Seeds/growth & development , Spectrometry, Mass, Electrospray Ionization
9.
Curr Med Chem ; 17(5): 467-78, 2010.
Article in English | MEDLINE | ID: mdl-20015036

ABSTRACT

Since its discovery in the early 1960's, abscisic acid (ABA) has received considerable attention as an important phytohormone, and more recently, as a candidate medicinal in humans. In plants it has been shown to regulate important physiological processes such as response to drought stress, and dormancy. The discovery of ABA synthesis in animal cells has generated interest in the possible parallels between its role in plant and animal systems. The importance of this molecule has prompted the development of several methods for the chemical synthesis of ABA, which differ significantly from the biosynthesis of ABA in plants through the mevalonic acid pathway. ABA recognition in plants has been shown to occur at both the intra- and extracellularly but little is known about the perception of ABA by animal cells. A few ABA molecular targets have been identified in vitro (e.g., calcium signaling, G protein-coupled receptors) in both plant and animal systems. A unique finding in mammalian systems, however, is that the peroxisome proliferator-activated receptor, PPAR gamma, is upregulated by ABA in both in vitro and in vivo studies. Comparison of the human PPAR gamma gene network with Arabidopsis ABA-related genes reveal important orthologs between these groups. Also, ABA can ameliorate the symptoms of type II diabetes, targeting PPAR gamma in a similar manner as the thiazolidinediones class of anti-diabetic drugs. The use of ABA in the treatment of type II diabetes, offers encouragement for further studies concerning the biomedical applications of ABA.


Subject(s)
Abscisic Acid/pharmacology , Hypoglycemic Agents/pharmacology , Abscisic Acid/chemical synthesis , Abscisic Acid/chemistry , Calcium Signaling , Humans , Hypoglycemic Agents/chemical synthesis , Hypoglycemic Agents/chemistry , PPAR gamma/metabolism , Receptors, G-Protein-Coupled/metabolism
10.
Chem Biol ; 13(10): 1051-60, 2006 Oct.
Article in English | MEDLINE | ID: mdl-17052609

ABSTRACT

The hepatitis C virus (HCV) is a growing global health problem. Small molecules that interfere with host-viral interactions can serve as powerful tools for elucidating the molecular mechanisms of pathogenesis and defining new strategies for therapeutic development. Using a cell-based screen involving subgenomic HCV replicons, we identified the ability of 18 different abscisic acid (ABA) analogs, originally developed as plant growth regulators, to inhibit HCV replication. Three of these were further studied. One compound, here named origamicin, showed antiviral activity through the inhibition of host proteins involved in protein folding. Origamicin could therefore be an important tool for studying the maturation of both host and viral proteins. Herein we demonstrate an application for molecular scaffolds based on ABA for mammalian cell targets involved in protein folding.


Subject(s)
Abscisic Acid/pharmacology , Alkynes/pharmacology , Antiviral Agents/pharmacology , Cyclohexanones/pharmacology , Hepacivirus/drug effects , Protein Folding , Virus Replication/drug effects , Abscisic Acid/chemical synthesis , Abscisic Acid/chemistry , Alkynes/chemical synthesis , Alkynes/chemistry , Antiviral Agents/chemistry , Cell Line, Tumor , Cell Proliferation/drug effects , Cyclohexanones/chemical synthesis , Cyclohexanones/chemistry , Dose-Response Relationship, Drug , Gene Expression Regulation, Viral/drug effects , Gene Expression Regulation, Viral/genetics , Hepacivirus/genetics , Humans , Microbial Sensitivity Tests , Molecular Structure , Molecular Weight , Tumor Cells, Cultured
11.
Org Biomol Chem ; 4(22): 4186-92, 2006 Nov 21.
Article in English | MEDLINE | ID: mdl-17312975

ABSTRACT

Short and high-yielding syntheses of enantiomerically pure (S)-(+) and (R)-(-)-abscisic acid are described. The syntheses proceed through key intermediates that preferentially recrystallise as single diastereoisomers for each enantiomer. This route allows the preparation of either enantiomer of abscisic acid in ca. 30% overall yield, and as demonstrated, gives access to an enantiomerically pure abscisic acid analogue.


Subject(s)
Abscisic Acid/analogs & derivatives , Abscisic Acid/chemical synthesis , Abscisic Acid/chemistry , Crystallography, X-Ray , Models, Molecular , Molecular Structure , Stereoisomerism
12.
Bioorg Med Chem Lett ; 15(23): 5226-9, 2005 Dec 01.
Article in English | MEDLINE | ID: mdl-16169217

ABSTRACT

(1'S*,2'S*)-(+/-)-6-Nor-2',3'-dihydro-4'-deoxo-ABA (2) was designed and synthesized as a candidate lead compound for developing a potent and specific inhibitor of ABA 8'-hydroxylase. This compound acted as an effective competitive inhibitor of the enzyme, with a K(I) value of 0.40microM, without exhibiting ABA activity. However, compound 2 also functioned as an enzyme substrate, making it a short-lived inhibitor. The 8'-difluorinated derivative of 2 (4) was synthesized as a long-lasting alternative. Compound 4 resisted 8'-hydroxylation, but inhibited ABA 8'-hydroxylation as effectively as 2. These results suggest that compound 2 is a useful lead compound for the future design and development of an ideal ABA 8'-hydroxylase inhibitor.


Subject(s)
Abscisic Acid/analogs & derivatives , Cytochrome P-450 Enzyme Inhibitors , Enzyme Inhibitors/chemistry , Mixed Function Oxygenases/antagonists & inhibitors , Abscisic Acid/chemical synthesis , Abscisic Acid/chemistry , Abscisic Acid/pharmacology , Cytochrome P-450 Enzyme System , Drug Design , Enzyme Inhibitors/chemical synthesis , Enzyme Inhibitors/pharmacology , Plant Proteins
13.
Biosci Biotechnol Biochem ; 67(11): 2408-15, 2003 Nov.
Article in English | MEDLINE | ID: mdl-14646201

ABSTRACT

The concentration of abscisic acid in plants is regulated not only by biosynthesis, but also by metabolism. Abscisic acid is metabolized to phaseic acid via 8'-hydroxyabscisic acid, and phaseic acid is then converted to dihydrophaseic acid and its epimer. A quantitative analysis of these metabolites is important as well as that of abscisic acid to understand changes in the concentration of abscisic acid in plants. However, no internal standards of the metabolites suitable for quantitative analysis have been reported. We prepared 7'-deuterium-labeled phaseic acid with a deuterium content of 86%, using the equilibrium reaction between phaseic acid and 8'-hydroxyabscisic acid. 7'-Deuterium-labeled dihydrophaseic acids were obtained by reducing 7'-deuterium-labeled phaseic acid. The levels of the metabolites in plant organs were determined by using the deuterated metabolites as internal standards.


Subject(s)
Abscisic Acid/analogs & derivatives , Abscisic Acid/analysis , Plants/chemistry , Sesquiterpenes/analysis , Abscisic Acid/chemical synthesis , Deuterium , Flowers/chemistry , Isotope Labeling/methods , Kinetics , Malus/chemistry , Models, Molecular , Plant Leaves/chemistry , Reference Values , Sesquiterpenes/chemical synthesis
14.
Biosci Biotechnol Biochem ; 64(5): 1071-4, 2000 May.
Article in English | MEDLINE | ID: mdl-10879485

ABSTRACT

New abscisic acid analogs possessing a cyano or methoxycarbonyl group at the 6'alpha-position of methyl abscisate were synthesized by regioselective hydrocyanation. These compounds had weak activity in the rice second leaf sheath elongation test.


Subject(s)
Abscisic Acid/chemical synthesis , Plant Growth Regulators , Abscisic Acid/analogs & derivatives , Abscisic Acid/chemistry , Molecular Conformation , Molecular Structure , Oryza/drug effects , Oryza/growth & development , Plant Growth Regulators/chemistry , Plant Growth Regulators/pharmacology , Plant Leaves/drug effects , Plant Leaves/growth & development
15.
Bioorg Med Chem Lett ; 10(14): 1571-4, 2000 Jul 17.
Article in English | MEDLINE | ID: mdl-10915053

ABSTRACT

Replacing the 4'-carbonyl group of abscisic acid with a methoxy group does not affect the abscisic acid (ABA)-like activities of the product in barley aleurone protoplasts, although the reduction of ABA to 4'-hydroxyl derivatives significantly reduces the ABA-like activity of the products. This suggests that methoxy derivatives of abscisic acid might be used to produce probes for ABA binding proteins.


Subject(s)
Abscisic Acid/analogs & derivatives , Abscisic Acid/chemical synthesis , Plant Growth Regulators/chemical synthesis , alpha-Amylases/biosynthesis , Abscisic Acid/chemistry , Abscisic Acid/pharmacology , Drug Design , Enzyme Induction/drug effects , Hordeum/enzymology , Molecular Structure , Plant Growth Regulators/chemistry , Plant Growth Regulators/pharmacology , Protoplasts/drug effects , Protoplasts/enzymology , Structure-Activity Relationship
16.
J Agric Food Chem ; 47(1): 313-7, 1999 Jan.
Article in English | MEDLINE | ID: mdl-10563891

ABSTRACT

Fluorine was introduced into the 2-position of the side chain of abscisic acid (ABA) analogues by Wittig reaction of alpha-ionone derivatives with ethyl triethylphosphono-2-fluoroacetate. The effects of the fluorinated analogues were evaluated on inhibition of cress seed germination and inhibition of gibberellin-inducible alpha-amylase induction in embryoless barley half-seeds. (2E, 4E)-2-Fluoro-5-(1'-hydroxy-2',6', 6'-trimethyl-2'-cyclohexen-1'-yl)-3-methyl-2,4-pentadienoic acid (5b) showed potent inhibitory activity at the same level as ABA in the cress seed germination test, and 5b also inhibited gibberellin-inducible alpha-amylase induction at 4 x 10(-)(6), 3 times the concentration of ABA (1 x 10(-)(6)) for 50% inhibition of alpha-amylase production. 5b also showed dehydrin induction activity. These results indicate that fluorinated ABA analogues mimic ABA action and can be a lead for a plant growth regulator which regulates plant growth or protects plants from environmental stresses.


Subject(s)
Abscisic Acid/analogs & derivatives , Abscisic Acid/chemical synthesis , Abscisic Acid/pharmacology , Enzyme Induction , Germination/drug effects , Hordeum/embryology , Hordeum/enzymology
17.
Folia Microbiol (Praha) ; 37(2): 159-60, 1992.
Article in English | MEDLINE | ID: mdl-1387101

ABSTRACT

The plant hormone abscisic acid as well as its synthetic analog LAB 173711 significantly increased the nitrogenase activity of the bacterium Azotobacter chroococcum and the cyanobacterium Nostoc muscorum. The effect depended on the concentration of the substances (0.001-10 mg/L) and the age of the cultures. The biomass of the organisms was not significantly influenced.


Subject(s)
Abscisic Acid/pharmacology , Azotobacter/enzymology , Cyanobacteria/enzymology , Nitrogenase/metabolism , Abscisic Acid/chemical synthesis , Azotobacter/drug effects , Azotobacter/growth & development , Cyanobacteria/drug effects , Cyanobacteria/growth & development , Nitrogenase/drug effects
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