STUDIES ON PLANT GROWTH-REGULATING SUBSTANCES

The cress-root test and the maize-root segment tests, both of which depend on the measurement of root-growth inhibition, have been used to assess the growth-regulating activity of a wide range of phenoxyalkanecarboxylic acids. The results are presented and compared with those obtained with the same compounds in other tests in which shoot tissues were employed. The results are also discussed in relation to current theories on mode of action and structure/activity relationship. These studies included the 'α-hydrogen' effect, the activity of stereoisomers and activity of homologues of seventeen series of ω-phenoxyalkanecarboxylic acids, considered in relation to their degradation within the tissues by β-oxidation. Earlier findings were largely confirmed. Compounds which had previously been shown to be active in shoot tests such as the wheat-cylinder, the pea-curvature and the pea-segment tests, were found to be active in the root-growth inhibition tests and, furthermore, the degree of activity was usually similar.
It is concluded that the two root tests investigated are of real value in assessing the activity of phenoxy acids in studies on the relationships between chemical structure and plant growth-regulating activity.     

Studies on plant growth-regulating substances

Series of I, I-dichloro-2-phenoxyethanes, α,α-dichlorotoluenes and I, I-dihalo-2-phenylethanes have been examined for plant growth-regulating activity in a number of tests. Some compounds were shown to be active and the results, together with those obtained from metabolism studies, are discussed in terms of chemical structure/biological activity relationships and mode of action.     

Studies on plant growth-regulating substances. XLIII. 2 -Chloro -3 -phenoxypropionitriles

A number of ring substituted 2-chloro-3-phenoxypropionitriles have been prepared and their plant growth-regulating activity has been assessed in the wheat coleoptile, pea segment and pea curvature tests, and also by spray treatments on tomato and dwarf French bean plants. The activities of these compounds are compared with those of previously studied 2-chloro-3-phenylpropionitriles and the results are discussed in terms of chemical structure/biological activity relationships and mode of action.     

Studies on plant growth-regulating substances. XXX. The plant growth-regulating activity of substituted phenols

The growth-regulating activity of a number of substituted monophenols and related compounds has been assessed in the wheat cylinder, pea segment, pea curvature and tomato-leaf epinasty tests and the effect on activity of position, size and electronic nature of the substituents has been studied. The results indicate that, for high auxin activity, electron-attracting substituents, having certain steric properties must be substituted in the 2- and 6-positions. Furthermore, at least one of these ortho-substituents must be capable of intramolecular bonding with the hydrogen of the phenolic hydroxyl group. Any substituent in the para-position to the hydroxyl group leads to complete loss of activity and activity is reduced by meta-substitution. This new group of phenolic plant growth regulators is considered in relation to other synthetic auxins from the viewpoints of structural requirements for activity and current theories on mode of action.     

Studies on plant growth-regulating substances. XLIX. Phenoxyalkenes

A series of phenoxyalkenes has been examined in a number of tests for plant growth-regulating and selective herbicidal properties. Some of these compounds were found to possess high activity. The results are discussed in terms of chemical structure/biological activity relationships and mode of action.     

Plant hormones and plant growth regulators in plant tissue culture

Summary This is a short review of the classical and new, natural and synthetic plant hormones and growth regulators (phytohormones) and highlights some of their uses in plant tissue culture. Plant hormones rarely act alone, and for most processes— at least those that are observed at the organ level—many of these regulators have interacted in order to produce the final effect. The following substances are discussed: (a) Classical plant hormones (auxins, cytokinins, gibberellins, abscisic acid, ethylene and growth regulatory substances with similar biological effects. New, naturally occurring substances in these categories are still being discovered. At the same time, novel structurally related compounds are constantly being synthesized. There are also many new but chemically unrelated compounds with similar hormone-like activity being produced. A better knowledge of the uptake, transport, metabolism, and mode of action of phytohormones and the appearance of chemicals that inhibit synthesis, transport, and action of the native plant hormones has increased our knowledge of the role of these hormones in growth and development. (b) More recently discovered natural growth substances that have phytohormonal-like regulatory roles (polyamines, oligosaccharins, salicylates, jasmonates, sterols, brassinosteroids, dehydrodiconiferyl alcohol glucosides, turgorins, systemin, unrelated natural stimulators and inhibitors), as well as myoinositol. Many of these growth active substances have not yet been examined in relation to growth and organized developmentin vitro.     

STUDIES ON PLANT GROWTH-REGULATING SUBSTANCES XI. AUXIN ANTAGONISM IN RELATION TO A THEORY ON MODE OF ACTION OF ARYL- AND ARYLOXY-ALKANECARBOXYLIC ACIDS

A study has been made of the antagonistic effects of a range of phenoxy and other acids on the growth-promoting activity of a number of auxins as assessed by the Avena cylinder and pea curvature tests. The compounds examined as inhibitors were selected on a logical basis, these molecules not possessing the structural requirements considered necessary for growth-regulating activity, yet possessing groupings which might allow them to accumulate at a site of action from which the growth response by auxins might be initiated. Our previous demonstrations that inactive stereoisomers of x-aryloxy propionic acids can competitively inhibit the activity of their active enantiomorph has been confirmed and a similar antagonism has been found to operate with other inactive aryloxy acids. Such competitive antagonism is discussed in relation to a 'three-point' contact theory on mode of action.     

Ribosome-inactivating proteins from plants: more than RNA N-glycosidases?

Many plants contain proteins that are capable of inactivating ribosomes and accordingly are called ribosome-inactivating proteins or RIPs. These typical plant proteins receive a lot of attention in biological and biomedical research because of their unique biological activities toward animal and human cells. In addition, evidence is accumulating that some RIPs play a role in plant defense and hence can be exploited in plant protection. To understand the mode of action of RIPs and to optimize their medical and therapeutical applications and their use as antiviral compounds in plant protection, intensive efforts have been made to unravel the enzymatic activities of RIPs and provide a structural basis for these activities. Though marked progress has been made during the last decade, the enzymatic activity of RIPs has become a controversial issue because of the concept that RIPs possess, in addition to their classical RNA N-glycosidase and polynucleotide:adenosine glycosidase activity, other unrelated enzymatic activities. Moreover, the presumed novel enzymatic activities, especially those related to diverse nuclease activities, are believed to play an important role in various biological activities of RIPs. However, both the novel enzymatic activities and their presumed involvement in the biological activities of RIPs have been questioned because there is evidence that the activities observed are due to contaminating enzymes. We offer a critical review of the pros and cons of the putative novel enzymatic activities of RIPs. Based on the available data, it is suggested that there is little conclusive evidence in support of the presumed activities and that in the past too little attention has been given to the purity of the RIP preparation. The antiviral activity and mode of action of RIPs in plants are discussed in view of their classical and presumed novel enzymatic activities.     

Allelopathic evidence in the Poaceae

The Poaceae family has been reported in several published works to show evidence of allelopathic activity. Secondary metabolites as phenolic compounds, hydroxamic acids, flavonoids, etc. commonly occur in both cultivated and wild Gramineae. This article, therefore, attempts to review and synthesize past and recent findings concerning the allelopathic activity of this family. It reviews the type of the activity (stimulative or inhibitive), the donor plant, the target species, and the mode of action in each case.     

Flavonoid glycosides isolated from unique legume plant extracts as novel inhibitors of xanthine oxidase

Legumes and the polyphenolic compounds present in them have gained a lot of interest due to their beneficial health implications. Dietary polyphenolic compounds, especially flavonoids, exert antioxidant properties and are potent inhibitors of xanthine oxidase (XO) activity. XO is the main contributor of free radicals during exercise but it is also involved in pathogenesis of several diseases such as vascular disorders, cancer and gout. In order to discover new natural, dietary XO inhibitors, some polyphenolic fractions and pure compounds isolated from two legume plant extracts were tested for their effects on XO activity. The fractions isolated from both Vicia faba and Lotus edulis plant extracts were potent inhibitors of XO with IC(50) values range from 40-135 μg/mL and 55-260 μg/mL, respectively. All the pure polyphenolic compounds inhibited XO and their K(i) values ranged from 13-767 μM. Ten of the compounds followed the non competitive inhibitory model whereas one of them was a competitive inhibitor. These findings indicate that flavonoid isolates from legume plant extracts are novel, natural XO inhibitors. Their mode of action is under investigation in order to examine their potential in drug design for diseases related to overwhelming XO action.     

Jasmonate-related mutants of Arabidopsis as tools for studying stress signaling

Jasmonates are naturally occurring signal compounds that regulate plant growth and development, and are involved in plant responses to several environmental stress factors. The mode of action of jasmonates has been investigated traditionally by analysis of the effects of exogenous application of these compounds, including identification of jasmonate-responsive genes and determination of their expression and responsive promoter elements. In addition, jasmonate biosynthesis has been studied by identification of biosynthetic enzymes, use of inhibitors and determination of endogenous jasmonate levels. Recently, several mutants defective in jasmonate biosynthesis and signaling have been isolated and their phenotypes shed new light on the role of jasmonates and jasmonate signaling in plant responses to pathogens, insects and ozone.     

Selective cytotoxicity evaluation in anticancer drug screening of fractionated plant extracts

Chosen to reflect biodiversity in a phylogenetic sense, 100 fractionated plant extracts were screened in vitro for cytotoxicity following extraction and fractionation (polypeptide isolation). Of these 100 extracts, 30 were selected and then characterized preliminarily for antitumor potency and mode of action by testing them on two cell lines and primary cultures of human tumor cells. On the basis of cytotoxicity potency, 10 of the extracts were further characterized for anticancer activity in 10 human tumor cell lines. This final testing resulted in seven potential lead plants with superior evidence of antitumor potential: Colchicum autumnale L. (Colchicaceae), Digitalis lanata Ehrh. and Digitalis purpurea L. (Plantaginaceae), Helleborus cyclophyllus Boiss. (Ranunculaceae), Menyanthes trifoliata L. (Menyanthaceae), and Viola arvensis Murr. and Viola patrinii Ging. (Violaceae). Within a database of antitumor compounds, the activity profiles of the extracts from these seven plants were compared, by correlation analysis, with those of more than 100 other compounds, including 39 standard drugs from different classes of cytotoxic mechanisms. The activity profiles of six of these candidates were uncorrelated with those of the standard drugs, possibly indicating new pathways of drug-mediated cell death.     

Studies on plant growth-regulating substances XXV. The plant growth-regulating activity of cinnamic acids

Effects of ring substitution on the plant growth-regulating activities of trans- and cis-cinnamic acids have been investigated in the wheat cylinder, pea segment and pea curvature tests. Most of the cis- acids were shown to be active. Substitution of fluorine, chlorine or bromine into the ring of cis-cinnamic acid in most cases increased the activity. The results are discussed in relation to mode of action and chemical structure/biological activity relationships: 4-chlorobenzoic acid is shown to act as a competitive antagonist towards 4-chloro-cis-cinnamic acid.     

Daminozide and prohexadione have similar modes of action as inhibitors of the late stages of gibberellin metabolism

One of the effects of daminozide is to retard shoot growth in certain plant species, but its mode of action is unclear. Prohexadione, an acylcyclohexanedione, also causes retardation of shoot growth, but it is active in all plant systems tested so far. This inhibition has been shown to be a result of competition with the natural co-substrate, 2-oxoglutarate, at the active site of hydroxylases involved in the later stages of the gibberellin (GA) biosynthesis pathway. In order to determine the mode of action of daminozide in relation to prohexadione, the potencies of the two retardants as inhibitors of 3β-hydroxylation of GAs in cell-free systems from pumpkin ( Cucurbita maxima ) endosperm and French bean ( Phaseolus coccineus ) cotyledons were studied. Several compounds, related to or representing structural links between daminozide and prohexadione, were also included in this investigation. Daminozide was found to inhibit only the bean 3β-hydroxylase to a significant degree, whereas prohexadione inhibited both the bean and pumpkin enzymes.
Further information was obtained from the GC-MS analysis of GAs found in the newly formed parts of the shoots of peanut seedlings treated with the two compounds. Both growth retardants inhibited the formation of GA₁, whereas its immediate precursor, GA₂₀, accumulated. Furthermore, levels of GA₈ (2β-hydroxy GA₁) were also reduced, but by a smaller relative amount.
These results clearly indicate for the first time that daminozide has the same mode of action as prohexadione in distinct plant species, namely to inhibit the 3β-hydroxylase and, to a lesser extent, the 2β-hydroxylase. This is probably due to the structural similarity of the two inhibitors with 2-oxoglutarate.     

A plant growth retardant related to chlamydocin and its proposed mechanism of action

A comparison of the plant growth retardant activity of the chlamydocin analogues, compound 1, six derivatives from 1 and 2, and two synthetic analogues revealed that there are two types of retardant in chlamydocin analogues. One, for example in compound 1, requires an oxygen atom at C-8 of the 2-aminodecanoic acid moiety to show retardant activity. The other, for example in compound 8, requires no oxygen atom at C-8 but requires a specific alkyl group chain length for activity. To determine the differences in mode of action of both types of retardant, rice seedlings were separately treated with compounds 1 and 8, and after appearance of dwarfism, their endogenous ABA and GA(1) levels were determined and compared to those of the control. Treatment with 1 (10 nmol/plant) increased ABA levels 4 times higher than that of the control and decreased GA(1) levels to 20% of that of the control. Treatment with 8 (30 nmol/plant) did not affect the ABA level but decreased GA(1) content to 5% of that of the control.     

Properties of plant aminotransferases

The occurrence and properties of plant aminotransferases are considered in relation to the known characteristics of corresponding animal and bacterial aminotransferases. Development of aminotransferase systems during seed germination and plant development is examined and changes in the activity of various systems are discussed in relation to environmental factors and endogenous hormone changes. Purification and substrate specificity of various plant aminotransferases are considered and the evidence for substrate multispecificity shown by certain enzymes is related to similar findings with some animal and bacterial aminotransferases. The physical and kinetic properties of plant aminotransferases such as their molecular weight, sedimentation coefficient, subunit composition, pyridoxal phosphate requirement, effect of pH and cations on activity, and their mechanism of action are reviewed and compared to similar observations from animal and bacterial aminotransferases. Finally, the intracellular location and functions of plant aminotransferases and their isoenzyme composition are discussed and compared to those of corresponding animal enzymes.     

The synthesis and antiviral activity of 4-fluoro-1-beta-D-ribofuranosyl-1H-pyrazole-3-carboxamide

A novel fluoropyrazole ribonucleoside has been shown to have significant anti-influenza activity in vitro. The compound is compared and contrasted with the structurally-related compound ribavirin in attempts to identify factors having significant bearing on the mode of action of both compounds.     

Acetylcholinesterase inhibitory activity of stigmasterol & hexacosanol is responsible for larvicidal and repellent properties of Chromolaena odorata

BackgroundChromolaena odorata, has been traditionally known for its insect repellent property. Aim of this study was to determine larvicidal tendency of C. odorata on Culex quinquefasciatus and isolate compounds responsible for this activity and to determine the mechanism of action of these compounds.MethodsC. odorata plant extract was screened for mosquito larvicidal activity. The extract was fractionated using chromatography and the bioactive fraction showing larvicidal activity was identified. The chemical nature of the compounds in the bioactive fraction was determined using NMR and Mass spectrometry.ResultsWe identified phytosterols and alkanols to be the compounds regulating larvicidal activity in the bioactive fraction of the plant extract. Stigmasterol and 1-hexacosanol were identified to be the chief orchestrators of larvicidal activity and their mode of action has been observed to be neurotoxicity. At a molecular level both stigmasterol and 1-hexacosanol were found to be inhibiting acetylcholinesterase activity in C. quinquefasciatus & A. aegypti. The acetylcholinesterase inhibitory effect was validated in vitro using recombinant acetylcholinesterase and ex vivo in larval homogenates of Culex and Aedes. Electrophysiological studies using electroantennography have shown enhanced neural response to these compounds.ConclusionsNeurotoxic effect of C. odorata derived stigmasterol and 1-hexacosanol, exerted through acetylcholinesterase inhibition was responsible for the mortality of C. quinquefasciatus, A. aegypti & Chironomus riparius. EAG studies pointed out hyper-excitability of the olfactory system by these compounds.General significanceThese compounds are natural agents for mosquito control that can be used in vector control as larvicidal compounds, pending further investigations.     

Untersuchungen zum Wirkungsspektrum und zur Wirkungsweise zweier quarternärer Ammoniumverbindungen gegenüber phytopathogenen Viren

Investigation of the influence of two quarternary ammonium compounds on some viruses and their mode of action The inhibitory effect of benzyl-dimethyl-hexadecylammoniumchloride (BDHA) and N-benzyl-N-dodecyl-N-bis (2-liydroxyethyl)-ammoniumchloride (BDBA) to various phytopathogenic viruses was studied. These substances were selected from 10 other quarternary ammonium compounds tested. They showed an inhibitory activity against BMV-, CMV-, CMoV-, PVX-, TMV- and TNV-infections. Studies on the mode of action of BDBA and BDHA in the virus-host-system TMV/Nicotiana tabacum var. Xanthi nc. revealed that the compounds exhibited besides a pre-infectional also a post-infectional inhibitory activity. Further, it has been shown that they display a direct inhibitory effect on TMV. The longlasting pre-infectional effect of the compounds resulted not only in a reduction of formation of local lesions, but also in a smaller size and a lower antigene content of the lesions. An antiviral activity was also detected in non-treated younger leaves of treated plants 10–14 days after treatment. This phenomenon was linked with the appearance of some new proteins in the intercellular fluids.     

The inter‐kingdom volatile signal indole promotes root development by interfering with auxin signalling

Recently, emission of volatile organic compounds (VOCs) has emerged as a mode of communication between bacteria and plants. Although some bacterial VOCs that promote plant growth have been identified, their underlying mechanism of action is unknown. Here we demonstrate that indole, which was identified using a screen for Arabidopsis growth promotion by VOCs from soil‐borne bacteria, is a potent plant‐growth modulator. Its prominent role in increasing the plant secondary root network is mediated by interfering with the auxin‐signalling machinery. Using auxin reporter lines and classic auxin physiological and transport assays we show that the indole signal invades the plant body, reaches zones of auxin activity and acts in a polar auxin transport‐dependent bimodal mechanism to trigger differential cellular auxin responses. Our results suggest that indole, beyond its importance as a bacterial signal molecule, can serve as a remote messenger to manipulate plant growth and development.