20-Hydroxyecdysterone - (2β,3β,5β,22R)-2,3,14,20,22,25-hexahydroxycholest-7-en-6-one was isolated in satisfactory yield using ethanol extraction from the aerial part of Silene wolgensis (Hornem.) Otth; sometimes Silene wolgensis (Willd.) Bess. ex Spreng. The complexation of the phytoecdysteroid with β-cyclodextrin was studied by NMR spectroscopy. By studying the changes in chemical shifts of protons of substrates and receptors it was found that ecdysterone interacts with cyclodextrins to form supramolecular inclusion complexes of stoichiometric composition of 1:1 or 1:2. Ecdysterone-β-cyclodextrin complexes exhibit 100 times higher solubility in water than the parent compound.
- Klíčová slova
- Cyclodextrins, Ecdysterones, Inclusion complexes, NMR spectroscopy,
- MeSH
- biologická dostupnost MeSH
- cyklodextriny chemie MeSH
- ekdysteron chemie izolace a purifikace farmakokinetika MeSH
- magnetická rezonanční spektroskopie MeSH
- molekulární konformace MeSH
- rozpustnost MeSH
- Silene chemie MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
- Názvy látek
- cyklodextriny MeSH
- ekdysteron MeSH
The polyhydroxylated derivatives of 6-keto,7-dehydrocholesterol (ecdysone, ecdysteroids, Ecd) are natural compounds widely distributed in plants. They exhibit strong anabolic, vitamin D-like, pharmacological effects in vertebrate animals and in the human body. In the larval stages of insects, injections of pure Ecd cause serious pathophysiological, "hyperecdysonic" syndromes associated with neuromuscular paralysis, premature cuticular apolysis and complete inhibition of ecdysis. Ecds do not penetrate insect cuticle. For this reason, all previous attempts to induce ecdysone responses by topical applications of Ecd failed. In this work, we tried to induce the topical effects of Ecd by preparation of more lipophilic complexes, with 2 or 4 molecules of 20-hydroxyecdysone (E20) attached to a relatively large nucleus of the porphyrin. The resulting porphyrin-E20 complexes (ecdysogens) have been subjected to standardised assays for ecdysone activity in the ligatured larvae ("dauerlarvae") of the greater waxmoth (Galleria mellonella). Similarly like the free E20 alone, porphyrin-E20 complexes had no effect when applied on the body surface or administered in the larval diet. When injected, however, they exhibited delayed effects, but the adverse ("hyperecdysonic") pathophysiological syndromes were reduced or abolished. It is concluded, therefore, that the replacement of pathophysiological, precocious or "hyperecdysonic" moults by the larval-pupal transformation, was due to successive metabolic liberation of the biologically active, free E20 from the porphyrin-E20 complex. The biological status of Ecd does not agree with their definition as the prothoracic gland (PG) hormone of insects, nor with the assumptions about a growth hormone of plants. A possibility that the most important status of Ecd may depend on the pharmacological properties of a sterolic D6 vitamin has been discussed.
- Klíčová slova
- 20-hydroxyecdysone (E20), Ecdysone, Ecdysone bioassays, Ecdysteroids (Ecds), Galleria mellonella, Hyperecdysonic syndromes, Neuromuscular paralysis by Ecd,
- MeSH
- aplikace lokální MeSH
- aplikace orální MeSH
- biologická proměna účinky léků MeSH
- ekdysteron aplikace a dávkování chemie farmakologie fyziologie MeSH
- kukla účinky léků MeSH
- larva účinky léků MeSH
- Lepidoptera účinky léků fyziologie MeSH
- porfyriny chemie farmakologie MeSH
- vztah mezi dávkou a účinkem léčiva MeSH
- zvířata MeSH
- Check Tag
- zvířata MeSH
- Publikační typ
- časopisecké články MeSH
- Názvy látek
- ekdysteron MeSH
- porfyriny MeSH
The aim of the work was to examine the effect of brassinosteroid (24-epibrassinolide; 24E) and ecdysteroid (20-hydroxyecdysone; 20E) on various parts of primary photosynthetic processes in maize and spinach. Additionally, the effect of steroids on gaseous exchange, pigment content and biomass accumulation was studied. The efficiency of the photosynthetic whole electron-transport chain responded negatively to the 24E or 20E treatment in both species, but there were interspecific differences regarding Photosystem (PS) II response. A positive effect on its oxygen-evolving complex and a slightly better energetical connectivity between PSII units were observed in maize whereas the opposite was true for spinach. The size of the pool of the PSI end electron acceptors was usually diminished due to 24E or 20E treatment. The treatment of plants with 24E or 20E applied individually positively influenced the content of photosynthetic pigments in maize (not in spinach). On the other hand, it did not affect gaseous exchange in maize but resulted in its reduction in spinach. Plants treated with combination of both steroids mostly did not significantly differ from the control plants. We have demonstrated for the first time that 20E applied in low (10nM) concentration can affect various parts of photosynthetic processes similarly to 24E and that brassinosteroids regulate not only PSII but also other parts of the photosynthetic electron transport chain - but not necessarily in the same way.
- Klíčová slova
- Brassinosteroids, Chlorophyll, Ecdysteroids, Gas exchange, OJIP analysis, Photosynthetic electron transport,
- MeSH
- brassinosteroidy aplikace a dávkování MeSH
- ekdysteron aplikace a dávkování MeSH
- fotosyntéza účinky léků genetika MeSH
- fotosystém II - proteinový komplex účinky léků genetika MeSH
- kukuřice setá účinky léků růst a vývoj MeSH
- listy rostlin účinky léků metabolismus MeSH
- oxidace-redukce MeSH
- rostlinné proteiny biosyntéza MeSH
- Spinacia oleracea účinky léků růst a vývoj MeSH
- steroidy heterocyklické aplikace a dávkování MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
- Názvy látek
- brassinolide MeSH Prohlížeč
- brassinosteroidy MeSH
- ekdysteron MeSH
- fotosystém II - proteinový komplex MeSH
- rostlinné proteiny MeSH
- steroidy heterocyklické MeSH
Beside ecdysone (1), ecdysterone (2) is one of the most common 5beta-cholest-7-en-6-one (ecdysteroid) derivatives, which, besides having a hormonal effect on invertebrates, possesses a number of favorable non-hormonal biological effects on mammals. The most interesting of these is that on degenerative diseases, one of which, up to now not clarified in detail, is the so-called adaptogenic effect (protection of the organism against adverse stress factors) associated with anabolic, gastroprotective, and antioxidant effects. A second group of favorable effects is the possibility of suppression of neurodegenerative processes and protection of the cardiovascular system (metabolic syndrome symptom suppression, antidiabetic activity, and protection of heart and blood vessels). Because of these properties, ecdysterone has the potential to be developed as a medicinal agent.
- MeSH
- anabolika farmakologie MeSH
- antioxidancia farmakologie MeSH
- diabetes mellitus farmakoterapie MeSH
- ekdysteron metabolismus farmakologie terapeutické užití MeSH
- hypoglykemika farmakologie MeSH
- kardiovaskulární systém účinky léků MeSH
- lidé MeSH
- metabolický syndrom farmakoterapie MeSH
- neurodegenerativní nemoci farmakoterapie MeSH
- vřed farmakoterapie MeSH
- zvířata MeSH
- Check Tag
- lidé MeSH
- zvířata MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
- přehledy MeSH
- Názvy látek
- anabolika MeSH
- antioxidancia MeSH
- ekdysteron MeSH
- hypoglykemika MeSH
The aim of this work was to isolate plant ecdysteroid-binding proteins using affinity chromatography. Ecdysteroids as insect hormones have been investigated thoroughly but their function and the mechanism of action in plants and other organisms is still unknown although ecdysteroids occur in some plants in a relatively large amount. Therefore, 20-hydroxyecdysone was immobilized on a polymeric carrier as a ligand for affinity chromatography in order to isolate plant ecdysteroid-binding proteins from the cytosolic extract of New Zealand spinach (Tetragonia tetragonoides). Non-specifically bound proteins were eluted with a rising gradient of concentration of sodium chloride, and 3% (v/v) acetic acid was used for the elution of the specifically bound proteins. Using this method, ribulose 1,5-bisphosphate carboxylase/oxygenase (RuBisCO) was isolated. The influence of ecdysteroids on RuBisCO was further studied. Our results show that ecdysteroids are able to increase the yield of RuBisCO-mediated reaction in which CO(2) is fixed into organic matter by more than 10%.
- MeSH
- chromatografie afinitní * MeSH
- cytosol enzymologie MeSH
- ekdysteron metabolismus MeSH
- enzymy imobilizované MeSH
- ribulosa-1,5-bisfosfát-karboxylasa izolace a purifikace metabolismus MeSH
- Spinacia oleracea enzymologie MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
- Názvy látek
- ekdysteron MeSH
- enzymy imobilizované MeSH
- ribulosa-1,5-bisfosfát-karboxylasa MeSH
Leuzea carthamoides is an adaptogenic plant containing biologically active compounds as ecdysteroids and guaianolide-type sesquiterpene lactones, conventionally extracted from the plant with ethanol. It may be a potential source of the mentioned natural compounds. Ethanol-modified near-critical CO(2) was used as selective solvent with the aim to increase the level of 20-hydroxyecdysone in the extract from L. carthamoides roots and to remove selectively cynaropicrin, a sesquiterpene lactone of bitter taste, from the leaves. The extraction conditions were varied (pressure 20-28 MPa, temperature 40-60 degrees C, ethanol concentration in the solvent 0-7.1%) and the extraction yield and extract composition were compared with the results of ethanolic extraction. The supercritical fluid extraction (SFE) from finely powdered plant was controlled by phase equilibrium. Cynaropicrin was quantitatively removed from the leaves where 89% of 20-hydroxyecdysone was retained. The extraction yield of 20-hydroxyecdysone from roots with ethanol-modified CO(2 )was lower by 30% than with ethanol but its concentration in the extract was higher by 67%.
- MeSH
- chemické modely MeSH
- chemické techniky analytické metody MeSH
- ekdysteron analýza izolace a purifikace MeSH
- ethanol chemie MeSH
- kořeny rostlin metabolismus MeSH
- laktony analýza izolace a purifikace MeSH
- Leuzea metabolismus MeSH
- listy rostlin metabolismus MeSH
- rostlinné extrakty metabolismus MeSH
- rozpouštědla chemie MeSH
- seskviterpeny analýza izolace a purifikace MeSH
- superkritická fluidní chromatografie metody MeSH
- teplota MeSH
- tlak MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
- Názvy látek
- cynaropicrin MeSH Prohlížeč
- ekdysteron MeSH
- ethanol MeSH
- laktony MeSH
- rostlinné extrakty MeSH
- rozpouštědla MeSH
- seskviterpeny MeSH
Injections of 38 pmol paraquat (1,1'-dimethyl-4,4'-bypyridilium) into adult Pyrrhocoris apterus (average body weight 29.6 mg in males and 36.9 mg in females) caused a significant elevation of lipid peroxidation and protein carbonylation and a decline of membrane fluidity in the microsomal brain fraction. Another manifestation of oxidative stress was a depletion of the reduced glutathione pool and reduction of the gamma-glutamyl transpeptidase activity in the brain extracts. The damaging action of paraquat on the brain was counteracted by simultaneous injection of 1 pmol 20-hydroxyecdysone (20E). 20E restrained lipid peroxidation and the formation of protein carbonyls, ameliorated changes in microsomal membrane fluidity, enhanced the level of reduced glutathione, and upregulated the activity of gamma-glutamyl transpeptidase. At the organismic level, 20E curtailed three detrimental effects caused by paraquat injection: the disappearance of a blood protein, the suppression of fecundity and egg hatchability, and the shortening of adult life span. The data showed that 20E provided a systemic antioxidant protection but the significance of endogenous ecdysteroids in the management of oxidative stress remains to be shown.
- MeSH
- biologické markery MeSH
- ekdysteron metabolismus farmakologie MeSH
- gama-glutamyltransferasa metabolismus MeSH
- glutathion metabolismus MeSH
- hemolymfa chemie MeSH
- herbicidy farmakologie MeSH
- Heteroptera účinky léků metabolismus MeSH
- hmyzí proteiny analýza MeSH
- oxidační stres účinky léků MeSH
- paraquat farmakologie MeSH
- pohlavní dimorfismus MeSH
- zvířata MeSH
- Check Tag
- mužské pohlaví MeSH
- ženské pohlaví MeSH
- zvířata MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
- Názvy látek
- biologické markery MeSH
- ekdysteron MeSH
- gama-glutamyltransferasa MeSH
- glutathion MeSH
- herbicidy MeSH
- hmyzí proteiny MeSH
- paraquat MeSH
The biological activities of selected specific ecdysteroids obtained by photochemical or chemical transformation are compared in the B(II) bioassay, in which the potency reflects the affinity of binding to the ligand-binding site of the Drosophila melanogaster ecdysteroid receptor. The compounds tested represent 14-deoxy, 14-dehydroxy, 14-hydroperoxy and 14-epi derivatives of 20-hydroxyecdysone and were selected on the basis of their close structural relationship to elucidate the contribution of the 14-hydroxy group and the stereochemical configuration at C-14 to ecdysteroid agonist activity. The structure-activity relationship shows that a 14-hydroxy group is not required for activity. However, the alpha-configuration of -H, -OH or -OOH at C-14, which determines the C/D rings trans-annelation, is very significant for activity; it is as important for activity as the well studied A/B rings cis-annelation. Compounds containing a double bond involving C-14 showed low activity with the exception of the specific, and so far unique, ecdysteroid dimer 7,7'-bis-[14-deoxy-8(14)-ene-20-hydroxyecdysone], which was obtained as the main product of the photochemical transformation of 20-hydroxyecdysone. The relatively high biological activity of this dimeric compound is discussed.
- MeSH
- biotest MeSH
- buněčné linie MeSH
- dimerizace MeSH
- Drosophila melanogaster MeSH
- ekdysteron analogy a deriváty chemie MeSH
- molekulární struktura MeSH
- steroidní receptory metabolismus MeSH
- vztahy mezi strukturou a aktivitou MeSH
- zvířata MeSH
- Check Tag
- zvířata MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
- Názvy látek
- ecdysteroid receptor MeSH Prohlížeč
- ekdysteron MeSH
- steroidní receptory MeSH
Structural modification of 20-hydroxyecdysone (20E) based on photochemical transformation yielded dimeric ecdysteroid 7alphaH,7'alphaH-bis-[(20R,22R)-2beta,3beta,20,22,25-pentahydroxy-5beta-cholest-8(14)-en-6-one-7-yl] as a main product. Its structure was determined by detailed NMR analysis. Furthermore, two new monomeric analogues: 14-epi-20-hydroxyecdysone and 14-deoxy-14,18-cyclo-20-hydroxyecdysone were identified in addition to the earlier described 14-deoxy and 14-hydroperoxy derivatives of 20E. Formation of the specific and so far unique ecdysteroid dimer has not been observed in earlier photo-transformation studies. The transformed dimeric analogue of 20-hydroxyecdysone retained the high agonistic activity on the ecdysone receptor in the B(II)-bioassay compared with the original 20E.
- MeSH
- dimerizace MeSH
- Drosophila melanogaster MeSH
- ekdysteroidy analogy a deriváty MeSH
- ekdysteron chemická syntéza chemie MeSH
- fotochemie metody MeSH
- magnetická rezonanční spektroskopie MeSH
- molekulární konformace MeSH
- molekulární modely MeSH
- spektrofotometrie infračervená MeSH
- steroidní receptory agonisté MeSH
- vysokoúčinná kapalinová chromatografie MeSH
- vztahy mezi strukturou a aktivitou MeSH
- zvířata MeSH
- Check Tag
- zvířata MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
- Názvy látek
- ecdysone receptor MeSH Prohlížeč
- ekdysteroidy MeSH
- ekdysteron MeSH
- steroidní receptory MeSH
Effects of methoprene and 20-hydroxyecdysone on the development and hemagglutination activity (HA) were studied in both sexes of two members of the Culex pipiens complex-anautogenous C. p. quinquefasciatus and autogenous C. p. molestus. Juvenile hormone analogue (methoprene) and 20-hydroxyecdysone caused developmental changes in both mosquito strains. High larval mortality, prolongation of intermolt period in each larval instar and in the pupal stage, and morphological changes in the larval-pupal and pupal-adult transformations were also observed. Developmental changes were accompanied with some differences in the HA. HA was found in both sexes of both experimental mosquito strains. The juvenile hormone analogue used in the larval stage caused significant decrease of HA in the gut of adults of both sexes. On the other hand, 20-hydroxyecdysone decreased HA only in the female gut. Results obtained indicate that HA depends on the sex, the studied organ, and the level of hormones.
- MeSH
- Culex účinky léků fyziologie MeSH
- ekdysteron farmakologie MeSH
- hemaglutinace účinky léků MeSH
- methopren farmakologie MeSH
- zvířata MeSH
- Check Tag
- mužské pohlaví MeSH
- ženské pohlaví MeSH
- zvířata MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
- Názvy látek
- ekdysteron MeSH
- methopren MeSH
