Advancements in small-molecule research have created the need for sensitive techniques to accurately study biological processes in living systems. Fluorescent-labeled probes have become indispensable tools, particularly those that use boron-dipyrromethene (BODIPY) dyes. Terpenes and terpenoids are organic compounds found in nature that offer diverse biological activities, and BODIPY-based probes play a crucial role in studying these compounds. Monoterpene-BODIPY conjugates have exhibited potential for staining bacterial and fungal cells. Sesquiterpene-BODIPY derivatives have been used to study sarcoplasmic/endoplasmic reticulum calcium ATPase (SERCA), indicating their potential for drug development. Owing to their unique properties, diterpenes have been investigated using BODIPY conjugates to evaluate their mechanisms of action. Triterpene-BODIPY conjugates have been synthesized for biological studies, with different spacers affecting their cytotoxicity. Fluorescent probes, inspired by terpenoid-containing vitamins, have also been developed. Derivatives of tocopherol, coenzyme Q10, and vitamin K1 can provide insights into their oxidation-reduction abilities. All these probes have diverse applications, including the study of cell membranes to investigate immune responses and antioxidant properties. Further research in this field can help better understand and use terpenes and terpenoids in various biological contexts.
- MeSH
- fluorescenční barviva chemie MeSH
- lidé MeSH
- molekulární struktura MeSH
- sloučeniny boru * chemie farmakologie MeSH
- terpeny * chemie farmakologie MeSH
- Check Tag
- lidé MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
- přehledy MeSH
Compounds isolated from botanical sources represent innovative and promising alternatives to conventional insecticides. Carlina oxide is a compound isolated from Carlina acaulis L. (Asteraceae) essential oil (EO) with great potential as bioinsecticide, being effective on various arthropod vectors and agricultural pests, with moderate toxicity on non-target species. Since the production from the wild source is limited, there is the need of exploring new synthetic routes for obtaining this compound and analogues with improved bioactivity and lower toxicity. Herein, the chemical synthesis of carlina oxide analogues was developed. Their insecticidal activity was assessed on the vectors Musca domestica L. and Culex quinquefasciatus Say, and their cytotoxicity was evaluated on a human keratinocyte cell line (HaCaT). The compounds' activity was compared with that of the natural counterparts EO and carlina oxide. In housefly tests, the analogues were comparably effective to purified carlina oxide. In Cx. quinquefasciatus assays, the meta-chloro analogue provided a significantly higher efficacy (LC50 of 0.71 μg mL-1) than the EO and carlina oxide (LC50 1.21 and 1.31 μg mL-1, respectively) and a better safety profile than carlina oxide on keratinocytes. Overall, this study can open the way to an agrochemical production of carlina oxide analogues employable as nature-inspired insecticides.
- MeSH
- Asteraceae * chemie MeSH
- Culex * MeSH
- insekticidy * farmakologie MeSH
- komáří přenašeči MeSH
- larva MeSH
- lidé MeSH
- oleje prchavé * farmakologie chemie MeSH
- zvířata MeSH
- Check Tag
- lidé MeSH
- zvířata MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
Naphthoquinones isolated from Quambalaria cyanescens (quambalarines) are natural pigments possessing significant cytotoxic and antimicrobial properties. Determining the structure of naphthoquinone compounds is important for the understanding of their biological activities and the informed synthesis of related analogues. Identifying quambalarines is challenging, because they contain a hydroxylated naphthoquinone scaffold and have limited solubility. Here, we report a detailed structural study of quambalarine derivatives, which form strong intramolecular hydrogen bonds (IMHBs) that enable the formation of several tautomers; these tautomers may complicate structural investigation due to their fast interconversion. To investigate tautomeric equilibria and identify new quambalarines, we complemented the experimental NMR spectroscopy data with density functional theory (DFT) calculations.
- MeSH
- antiinfekční látky chemie izolace a purifikace farmakologie MeSH
- antitumorózní látky chemie izolace a purifikace farmakologie MeSH
- Basidiomycota chemie MeSH
- magnetická rezonanční spektroskopie MeSH
- magnetická rezonanční tomografie MeSH
- molekulární struktura MeSH
- naftochinony chemie izolace a purifikace farmakologie MeSH
- vodíková vazba MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
A new method was developed for the mild and selective bromination of simple aromatic compounds and flavonoids in good yields using α,β-dibromohydrocinnamic acid in the presence of a base. This procedure enables selective mono- or dibromination of compounds highly sensitive to oxidative or radical attack. New brominated derivatives of silymarin flavonolignans and related flavonoids were prepared. These brominated derivatives can be used as valuable synthetic intermediates in further synthesis.
Stilbenoids are important components of foods (e.g., peanuts, grapes, various edible berries), beverages (wine, white tea), and medicinal plants. Many publications have described the anti-inflammatory potential of stilbenoids, including the widely known trans-resveratrol and its analogues. However, comparatively little information is available regarding the activity of their prenylated derivatives. One new prenylated stilbenoid (2) was isolated from Artocarpus altilis and characterized structurally based on 1D and 2D NMR analysis and HRMS. Three other prenylated stilbenoids were prepared synthetically (9-11). Their antiphlogistic potential was determined by testing them together with known natural prenylated stilbenoids from Macaranga siamensis and Artocarpus heterophyllus in both cell-free and cell assays. The inhibition of 5-lipoxygenase (5-LOX) was also shown by simulated molecular docking for the most active stilbenoids in order to elucidate the mode of interaction between these compounds and the enzyme. Their effects on the pro-inflammatory nuclear factor-κB (NF-κB) and the activator protein 1 (AP-1) signaling pathway were also analyzed. The THP1-XBlue-MD2-CD14 cell line was used as a model for determining their anti-inflammatory potential, and lipopolysaccharide (LPS) stimulation of Toll-like receptor 4 induced a signaling cascade leading to the activation of NF-κB/AP-1. The ability of prenylated stilbenoids to attenuate the production of pro-inflammatory cytokines tumor necrosis factor-α (TNF-α) and interleukin-1β (IL-1β) was further evaluated using LPS-stimulated THP-1 macrophages.
- MeSH
- buněčné linie MeSH
- cyklooxygenasy metabolismus MeSH
- inhibitory enzymů farmakologie MeSH
- lidé MeSH
- lipoxygenasy metabolismus MeSH
- NF-kappa B antagonisté a inhibitory MeSH
- prenylace * MeSH
- signální transdukce účinky léků MeSH
- stilbeny farmakologie MeSH
- transkripční faktor AP-1 antagonisté a inhibitory MeSH
- zánět prevence a kontrola MeSH
- Check Tag
- lidé MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
Honey is a unique natural product produced by European honeybees. Due to its high economic value, honey is considered to be well characterized chemically, and it is often discovered to be an adulterated commodity. However, this study shows that our knowledge of honey protein composition, which is of high medical and pharmaceutical importance, is incomplete. In this in-depth proteomic study of 13 honeys, we identified a number of proteins that are important for an understanding of honey properties and merit additional pharmaceutical research. Our major result is an expanded understanding of the proteins underlying honey's antimicrobial properties, such as hymenoptaecin and defensin-1, glucose dehydrogenase isoforms, venom allergens and other venom-like proteins, serine proteases and serine protease inhibitors, and a series of royal jelly proteins. In addition, we performed quantitative comparisons of all of the proteins previously known or newly identified. The honey proteins, determined using label-free nLC-MS/MS in which the same protein quantity was analyzed in one series, were found in relatively similar proportions, although eucalyptus honey differed most widely from the remaining honeys. Overall, the proteome analysis indicated that honeybees supply proteins to honey in a relatively stable ratio within each proteome, but total protein quantity can differ by approximately an order of magnitude in different honeys.
- MeSH
- alergeny analýza MeSH
- antibakteriální látky farmakologie MeSH
- inhibitory serinových proteinas analýza MeSH
- mastné kyseliny chemie MeSH
- med analýza MeSH
- proteomika metody MeSH
- serinové proteasy analýza MeSH
- živočišné jedy analýza MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
In this study, an extract from the bulbs of Cyrtanthus contractus showed strong anti-inflammatory activity in vitro. The extract was partially separated into 14 fractions and analyzed by ultra-high performance liquid chromatography-quadrupole time-of-flight mass spectrometry metabolomics, and the correlation coefficients were calculated between biological activities and metabolite levels. As a result, the top-scoring metabolite narciclasine (1) is proposed as the active principle of C. contractus. This was confirmed by comparing the biological effect of crude extract with that of an authentic standard.
- MeSH
- alkaloidy amarylkovitých chemie farmakologie MeSH
- Amaryllidaceae chemie MeSH
- antiflogistika nesteroidní chemie farmakologie MeSH
- buněčná adheze účinky léků MeSH
- buněčné linie MeSH
- endoteliální buňky pupečníkové žíly (lidské) účinky léků MeSH
- fenantridiny chemie farmakologie MeSH
- hmotnostní spektrometrie MeSH
- kořeny rostlin chemie MeSH
- lidé MeSH
- metabolomika * MeSH
- mezibuněčná adhezivní molekula-1 účinky léků metabolismus MeSH
- rostlinné extrakty chemie farmakologie MeSH
- viabilita buněk účinky léků MeSH
- vysokoúčinná kapalinová chromatografie MeSH
- Check Tag
- lidé MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
Three new alkaloids, bersavine (3), muraricine (4), and berbostrejdine (8), together with seven known isoquinoline alkaloids (1-2, 5-7, 9, and 10) were isolated from an alkaloidal extract of the root bark of Berberis vulgaris. The structures of the isolated compounds were determined by spectroscopic methods, including 1D and 2D NMR techniques, HRMS, and optical rotation, and by comparison of the obtained data with those in the literature. The NMR data of berbamine (5), aromoline (6), and obamegine (7) were completely assigned employing 2D NMR experiments. Alkaloids isolated in sufficient amounts were evaluated for their in vitro acetylcholinesterase, butyrylcholinesterase (BuChE), prolyl oligopeptidase, and glycogen synthase kinase-3β inhibitory activities. Selected compounds were studied for their ability to permeate through the blood-brain barrier. Significant human BuChE ( hBuChE) inhibitory activity was demonstrated by 6 (IC50 = 0.82 ± 0.10 μM). The in vitro data were further supported by computational analysis that showed the accommodation of 6 in the active site of hBuChE.
- MeSH
- acetylcholinesterasa metabolismus MeSH
- alkaloidy chemie izolace a purifikace terapeutické užití MeSH
- Alzheimerova nemoc farmakoterapie MeSH
- Berberis chemie MeSH
- butyrylcholinesterasa metabolismus MeSH
- cholinesterasové inhibitory terapeutické užití MeSH
- hematoencefalická bariéra účinky léků MeSH
- isochinoliny chemie izolace a purifikace terapeutické užití MeSH
- lidé MeSH
- magnetická rezonanční spektroskopie MeSH
- rostlinné exsudáty analýza MeSH
- Check Tag
- lidé MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
Strigolactones are a particular class of plant metabolites with diverse biological functions starting from the stimulation of parasitic seed germination to phytohormonal activity. The expansion of parasitic weeds in the fields of developing countries is threatening the food supply and calls for simple procedures to combat these weeds. Strigolactone analogues represent a promising approach for such control through suicidal germination, i.e., parasitic seed germination without the presence of the host causing parasite death. In the present work, the synthesis of resorcinol-type strigolactone mimics related to debranones is reported. These compounds were highly stable even at alkaline pH levels and able to induce seed germination of parasitic plants Striga hermonthica and Phelipanche ramosa at low concentrations, EC50 ≈ 2 × 10-7 M ( Striga) and EC50 ≈ 2 × 10-9 M ( Phelipanche). On the other hand, the mimics had no significant effect on root architecture of Arabidopsis plants, suggesting a selective activity for parasitic seed germination, making them a primary target as suicidal germinators.
- MeSH
- klíčení účinky léků MeSH
- laktony chemie farmakologie MeSH
- Orobanchaceae embryologie fyziologie MeSH
- regulátory růstu rostlin farmakologie MeSH
- resorcinoly chemie MeSH
- semena rostlinná účinky léků fyziologie MeSH
- Striga embryologie fyziologie MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
The queens of social insects differ from sterile colony members in many aspects of their physiology. Besides adaptations linked with their specialization for reproduction and extended lifespan, the queens also invest in the maintenance of their reproductive dominance by producing exocrine chemicals signaling their presence to the nestmates. The knowledge of the chemistry of queen-specific cues in termites is scarce. In addition to the contact recognition based on cuticular hydrocarbons, long-range signals mediated by volatiles are expected to participate in queen signaling, especially in populous colonies of higher termites (Termitidae). In queens of the higher termite Silvestritermes minutus (Syntermitinae), we have detected a previously undescribed volatile. It is present in important quantities on the body surface and in the headspace, ovaries, and body cavity. MS and GC-FTIR data analyses led us to propose the structure of the compound to be a macrolide 10-pentyl-3,4,5,8,9,10-hexahydro-2 H-oxecin-2-one. We performed enantiodivergent syntheses of two possible enantiomers starting from enantiopure ( S)-glycidyl tosylate. The synthetic sequence involved macrolide-closing metathesis quenched with a ruthenium scavenging agent. The absolute and relative configuration of the compound was assigned to be (5 Z,9 S)-tetradec-5-en-9-olide. Identification and preparation of the compound allow for investigation of its biological significance.
- MeSH
- hmotnostní spektrometrie MeSH
- indikátory a reagencie MeSH
- Isoptera chemie MeSH
- makrolidy chemická syntéza chemie farmakologie MeSH
- molekulární struktura MeSH
- ovarium chemie MeSH
- spektroskopie infračervená s Fourierovou transformací MeSH
- stereoizomerie MeSH
- zvířata MeSH
- Check Tag
- ženské pohlaví MeSH
- zvířata MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
