Your browser doesn't support javascript.
loading
Mostrar: 20 | 50 | 100
Resultados 1 - 20 de 16.618
Filtrar
1.
Food Chem ; 366: 130583, 2022 Jan 01.
Artigo em Inglês | MEDLINE | ID: mdl-34303203

RESUMO

Terpenoid metabolism at different developmental stages of Carya cathayensis was elucidated based on LC-MS/MS analysis and multi-omics. Terpenoid metabolites 2-hydroxy-1,4-naphoquinone and 3-hydroxybenzoic acid reached the maximum at 105 days after pollination (DAP) (P2 stage). To reveal the complex mechanism of C. cathayensis embryogenesis in relation to terpenoid metabolites (90-165 DAP), a metabolomic and transcriptional co-expression analysis was conducted. Based on RNA-Seq analysis, 679 genes of 1144 terpenoid biosynthesis were differentially expressed. Six terpenoid metabolites and 86 differentially expressed genes related to terpenoquinone metabolism were identified. Comprehensive analysis of metabolome and transcriptional data revealed that terpenoquinone accumulated in the early phase was active in the later phase. Overall, we profiled the transcriptome and metabolome changes in C. cathayensis during the developmental phase to investigate the metabolic pathways and candidate genes underlying the changes at different growth stages.


Assuntos
Carya , Cromatografia Líquida , Perfilação da Expressão Gênica , Espectrometria de Massas em Tandem , Terpenos , Transcriptoma
2.
J Agric Food Chem ; 69(34): 9743-9753, 2021 Sep 01.
Artigo em Inglês | MEDLINE | ID: mdl-34465092

RESUMO

Indirect defense is an important strategy employed by sessile plants to defend against herbivorous insects by recruiting the natural enemies of herbivores mediated by herbivore-induced plant volatiles (HIPVs). We aimed to determine whether indirect defense occurs in Compositae with Chrysanthemum morifolium as the model and elucidate the mechanisms underlying the biosynthesis of HIPVs. Using two-choice olfactometer bioassays, we showed that C. morifolium plants following infestation by larvae of the tobacco cutworm (Spodoptera litura, TCW) were significantly more attractive to two natural enemies of TCW larvae than control plants, indicating that indirect defense is an active defense strategy of C. morifolium. The chemical cue responsible for indirect defense in C. morifolium was identified as a complex blend of volatiles predominated by sesquiterpenes and monoterpenes. A total of 11 candidate terpene synthase (TPS) genes were identified by comparing the transcriptomes of healthy and TCW-infested plants. Gene expression analysis confirmed that up-regulated CmjTPS genes are consistent with the elevated emission of terpenes after herbivory treatment. Our study showed that the herbivore-induced emission of JA-dependent volatile terpenes attracted both predatory and parasitic enemies of herbivores. Generally, our findings indicate that indirect defense might be an important defense mechanism against insects in C. morifolium.


Assuntos
Chrysanthemum , Herbivoria , Animais , Chrysanthemum/genética , Larva , Spodoptera/genética , Terpenos
3.
Environ Monit Assess ; 193(10): 633, 2021 Sep 07.
Artigo em Inglês | MEDLINE | ID: mdl-34490544

RESUMO

Diagnostic ratios and compound-specific isotopic analysis (CSIA) are two tools that can help identify and differentiate the petrogenic and biogenic sources of hydrocarbons found in environmental samples. The present study aims to evaluate the concentration and type of n-alkanes and isoprenoids found in the oligotrophic waters of the Gulf of Mexico (n = 14), and through the typical diagnostic ratios reported for n-alkanes and its carbon isotopic composition (δ13C) to establish and differentiate the possible source of the hydrocarbons. Additionally, crude oil samples (n = 10) extracted in the Gulf of Mexico were evaluated by CSIA as a possible source of hydrocarbons to the study area. We found that the CSIA of δ13C for n-alkanes (n-C11 to n-C30) and isoprenoids (pristane and phytane) found in the surface water samples varied from - 25.55 to - 37.59‰ and from - 23.78 to - 33.97‰ in the crude oil samples, values which are more related to petrogenic sources. An analysis of the δ13C for pristane vs. phytane suggests that only three surface water samples show an origin in common that those observed in crude oils of the Gulf of Mexico. A low incidence of odd- and even-numbered n-alkanes higher than n-C25 in the water samples indicate low to negligible presence of terrigenous sources into the area, which was supported by the carbon isotopic composition of the individual n-alkanes.


Assuntos
Petróleo , Poluentes Químicos da Água , Alcanos/análise , Isótopos de Carbono/análise , Monitoramento Ambiental , Sedimentos Geológicos , Golfo do México , Petróleo/análise , Terpenos , Poluentes Químicos da Água/análise
4.
Planta ; 254(4): 67, 2021 Sep 08.
Artigo em Inglês | MEDLINE | ID: mdl-34495419

RESUMO

MAIN CONCLUSION: Transcriptomic and volatile component analyses showed that high expression levels of genes from the terpenoid backbone biosynthesis pathway and the monoterpene metabolic pathway can strengthen the floral fragrance of tree peony. Floral fragrance is a crucial ornamental trait whose improvement is one of the primary objectives of tree peony breeding. So far, exploration of the floral fragrance of tree peony has focused on the identification of its volatile components, but the molecular mechanisms responsible for their formation remain unclear. Here, we identified 128 volatile components from the petals of tree peony and found that they consisted primarily of terpenes, alcohols, and esters. Based on the distribution pattern of these major fragrance components, 24 tree peony cultivars were classified into 4 types: grassy scent (ocimene), woody scent (longifolene), lily of the valley scent (linalool), and fruity scent (2-ethyl hexanol). We used RNA-seq to explore the mechanistic basis of terpenoid metabolism in tree peony petals with various scents. The expression levels of AACT, HMGR, PMK, DXS, DXR, HDS, HDR, and GGPS, which encode key enzymes of terpenoid backbone biosynthesis, were upregulated in 'Huangguan' (strong fragrance) compared to 'Fengdan' (faint fragrance). Moreover, the transcript abundance of LIS and MYS, two monoterpene synthase genes, was also enhanced in petals of 'Huangguan' compared to those of 'Fengdan'. Together, these results demonstrate that differences in the expression of genes from the monoterpene synthesis and terpenoid backbone pathways are associated with differences in the fragrance of tree peony. This research provides crucial genetic resources for fragrance improvement and also lays a foundation for further clarification of the mechanisms that underlie tree peony fragrance.


Assuntos
Paeonia , Flores/genética , Regulação da Expressão Gênica de Plantas , Paeonia/genética , Melhoramento Vegetal , Terpenos , Transcriptoma/genética , Árvores
5.
J Agric Food Chem ; 69(36): 10678-10687, 2021 Sep 15.
Artigo em Inglês | MEDLINE | ID: mdl-34468130

RESUMO

Terpinen-4-ol, the main component of tea tree oil, markedly increases the disease resistance of postharvest strawberry fruit. To understand the mechanism underlying the enhancement of disease resistance, a high-throughput RNA-seq was used to analyze gene transcription in terpinen-4-ol-treated and untreated fruit. The results show that terpinen-4-ol induces the expression of genes in the jasmonic acid (JA) biosynthesis pathway, secondary metabolic pathways such as phenylpropanoid biosynthesis, and pathways involved in plant-pathogen interactions. Terpinen-4-ol treatment reduced disease incidence and lesion diameter in strawberry fruit inoculated with Botrytis cinerea. Terpinen-4-ol treatment enhanced the expression of genes involved in JA synthesis (FaLOX, FaAOC, and FaOPR3) and signaling (FaCOI1), as well as genes related to disease defense (FaPAL, FaCHI, and FaGLU). In contrast, treatment with the JA biosynthesis inhibitor salicylhydroxamic acid (SHAM) accelerated disease development and inhibited the induction of gene expressions by terpinen-4-ol. We conclude that the JA pathway participates in the induction of disease resistance by terpinen-4-ol in strawberry fruit. More generally, the results illuminate the mechanisms by which disease resistance is enhanced by essential oils.


Assuntos
Botrytis , Fragaria , Ciclopentanos , Resistência à Doença/genética , Fragaria/genética , Frutas/genética , Oxilipinas , Doenças das Plantas/genética , Transdução de Sinais , Terpenos
6.
J Med Microbiol ; 70(9)2021 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-34491156

RESUMO

Introduction. The increase of invasive fungal infections (IFIs) and associated treatment failure in populations at risk is driving us to look for new treatments.Hypothesis. The CIN-102 compound, derived from cinnamon essential oil, could be a new antifungal class with an activity, in particular, on strains resistant to current antifungals but also on biofilms, a factor of virulence and resistance of fungi.Aim. The aim of this study is to show the activity of CIN-102 on various strains resistant to current antifungals, on the biofilm and to determine the possibility of resistance induced with this compound.Methodology. We studied the MIC of CIN-102 and of current antifungals (voriconazole and amphotericin B) using CLSI techniques against eight different strains of three genera of filamentous fungi involved in IFIs and having resistance phenotypes to current antifungals. We also determined their effects on biofilm formation, and the induced resistance by voriconazole (VRC) and CIN-102.Results. MIC values determined for CIN-102 were between 62.5 and 250 µg ml-1. We demonstrated the antifungal effect of CIN-102 on biofilm, and more particularly on its formation, with 100 % inhibition achieved for most of the strains. CIN-102 at a sub-inhibitory concentration in the medium did not induce resistance in our strains, even after 30 generations.Conclusions. In this study we show that CIN-102 is effective against resistant filamentous fungi and against biofilm formation. In addition, our strains did not acquire a resistance phenotype against CIN-102 over time, unlike with VRC. CIN-102 is therefore an interesting candidate for the treatment of IFIs, including in cases of therapeutic failure linked to resistance, although further studies on its efficacy, safety and mechanism of action are needed.


Assuntos
Antifúngicos/farmacologia , Benzoatos/farmacologia , Biofilmes/efeitos dos fármacos , Cinamatos/farmacologia , Fungos/efeitos dos fármacos , Micoses , Terpenos/farmacologia , Anfotericina B/farmacologia , Combinação de Medicamentos , Humanos , Testes de Sensibilidade Microbiana , Micoses/tratamento farmacológico , Micoses/microbiologia , Voriconazol/farmacologia
7.
Zhongguo Zhong Yao Za Zhi ; 46(15): 3789-3796, 2021 Aug.
Artigo em Chinês | MEDLINE | ID: mdl-34472251

RESUMO

The genus Chloranthus has 13 species and 5 varieties in China, which can be found in the southwest and northeast regions. Phytochemical studies on Chloranthus plants have reported a large amount of terpenoids, such as diterpenoids, sesquiterpenoids, and sesquiterpenoid dimers. Their anti-inflammation, anti-tumor, antifungal, antivirus, and neuroprotection activities have been confirmed by previous pharmacological research. Herein, research on the chemical constituents from Chloranthus plants and their biological activities over the five years was summarized to provide scientific basis for the further development and utilization of Chloranthus plants.


Assuntos
Diterpenos , Sesquiterpenos , Compostos Fitoquímicos/farmacologia , Plantas , Sesquiterpenos/farmacologia , Terpenos
8.
Zhongguo Zhong Yao Za Zhi ; 46(15): 3797-3805, 2021 Aug.
Artigo em Chinês | MEDLINE | ID: mdl-34472252

RESUMO

Terpenes are the largest group of natural products and contain the widest assortment of structural types. Terpene cyclization is also the most complex reaction found in nature. For a long time, terpenoids with diverse structures have attracted natural product chemists to explore their biosynthesis mechanism. Such a large number of terpene skeletons are catalyzed by enzymes called terpene synthase. Sesquiterpene synthase is a kind of terpene synthase, which can catalyze the cyclization of linear precursor farnesyl pyrophosphate(FPP) to sesquiterpene skeletons. Sesquiterpene synthase cyclize a single precursor FPP into many sesquiterpene skeletons. With the continuous discovery of sesquiterpene synthase, the cyclization mechanism of sesquiterpene synthase has been studied deeply. In recent years, with the development and improvement of isotope labeling of substrate FPP and structural analysis of sesquiterpene synthase, the structure and cyclization mechanism of sesquiterpene synthase have been studied more systematically and accurately. In this review, we reviewed the progress of the research methods on the mechanism of sesquiterpene cyclization by substrate isotope labeling and protein structure, as well as the summary and prospect of sesquiterpene synthase research.


Assuntos
Sesquiterpenos , Ciclização , Terpenos
9.
Zhongguo Zhong Yao Za Zhi ; 46(15): 3877-3885, 2021 Aug.
Artigo em Chinês | MEDLINE | ID: mdl-34472263

RESUMO

Twenty-six compounds, including sixteen meroterpenoids(1-16), a triterpenoid(17), four terpenoid derivatives(18-21), and five aromatic compounds(22-26), were isolated from the leaves of Psidium guajava. Their structures were identified by spectroscopic analyses including NMR and MS. Compounds 21-26 were obtained from plants of Psidium for the first time. Based on the structure,(R)-2-ethylhexyl 2H-1,2,3-triazole-4-carboxylate(24 a), an α-glucosidase inhibitor recently isolated from Paramignya trimera, should be revised as compound 24. Meroterpenoids 1-16 were evaluated for their antitumor and antifungal activities. Meroterpenoids psiguajadial D(4), guapsidial A(5), 4,5-diepipsidial A(7), guadial A(14), and guadial B(15) showed cytotoxicities against five human tumor cell lines(HL-60, A-549, SMMC-7721, MCF-7, and SW-480), among which 5 was the most effective with an IC_(50) of 3.21-9.94 µmol·L~(-1).


Assuntos
Psidium , Antifúngicos/farmacologia , Humanos , Espectroscopia de Ressonância Magnética , Extratos Vegetais , Folhas de Planta , Terpenos
10.
Photochem Photobiol Sci ; 20(10): 1357-1378, 2021 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-34537894

RESUMO

Natural products and their analogue have played a key role in the drug discovery and development process. In the laboratory, the total synthesis of secondary metabolites is very useful in ascertaining the hypothetical complex structure of molecules of natural origin. Total synthesis of natural products using Norrish type I and II reactions as a crucial step has been explored in this overview. Norrish reactions are important photo-induced transformations of carbonyl compounds in organic synthetic chemistry and are connected in numerous industrially and biologically relevant procedures and the processing of carbonyl compounds in the atmosphere. The present review tries to focus on the brilliant applications of Norrish type I and II photochemical reactions as a key step in the total synthesis of natural products and highlights on natural sources, structures, and biological activities of the promising natural products for the first time elegantly.


Assuntos
Produtos Biológicos/síntese química , Alcaloides/síntese química , Alcaloides/química , Antibacterianos/síntese química , Antibacterianos/química , Produtos Biológicos/química , Ciclização/efeitos da radiação , Luz , Naftalenos/síntese química , Naftalenos/química , Policetídeos/síntese química , Policetídeos/química , Teoria Quântica , Compostos de Espiro/síntese química , Compostos de Espiro/química , Terpenos/síntese química , Terpenos/química
11.
Nat Plants ; 7(9): 1239-1253, 2021 09.
Artigo em Inglês | MEDLINE | ID: mdl-34475528

RESUMO

Aristolochia, a genus in the magnoliid order Piperales, has been famous for centuries for its highly specialized flowers and wide medicinal applications. Here, we present a new, high-quality genome sequence of Aristolochia fimbriata, a species that, similar to Amborella trichopoda, lacks further whole-genome duplications since the origin of extant angiosperms. As such, the A. fimbriata genome is an excellent reference for inferences of angiosperm genome evolution, enabling detection of two novel whole-genome duplications in Piperales and dating of previously reported whole-genome duplications in other magnoliids. Genomic comparisons between A. fimbriata and other angiosperms facilitated the identification of ancient genomic rearrangements suggesting the placement of magnoliids as sister to monocots, whereas phylogenetic inferences based on sequence data we compiled yielded ambiguous relationships. By identifying associated homologues and investigating their evolutionary histories and expression patterns, we revealed highly conserved floral developmental genes and their distinct downstream regulatory network that may contribute to the complex flower morphology in A. fimbriata. Finally, we elucidated the genetic basis underlying the biosynthesis of terpenoids and aristolochic acids in A. fimbriata.


Assuntos
Aristolochia/crescimento & desenvolvimento , Aristolochia/genética , Ácidos Aristolóquicos/biossíntese , Evolução Biológica , Flores/crescimento & desenvolvimento , Flores/genética , Magnoliopsida/genética , Terpenos/metabolismo , Ácidos Aristolóquicos/genética , Variação Genética , Genoma de Planta , Genótipo , Filogenia , Plantas Medicinais/genética , Plantas Medicinais/crescimento & desenvolvimento
12.
Molecules ; 26(15)2021 Jul 29.
Artigo em Inglês | MEDLINE | ID: mdl-34361745

RESUMO

The edible parts of the plants Camellia sinensis, Vitis vinifera and Withania somnifera were extensively used in ancient practices such as Ayurveda, owing to their potent biomedical significance. They are very rich in secondary metabolites such as polyphenols, which are very good antioxidants and exhibit anti-carcinogenic properties. This study aims to evaluate the anti-cancerous properties of these plant crude extracts on human liver cancer HepG2 cells. The leaves of Camellia sinensis, Withania somnifera and the seeds of Vitis vinifera were collected and methanolic extracts were prepared. Then, these extracts were subjected to DPPH, α- amylase assays to determine the antioxidant properties. A MTT assay was performed to investigate the viability of the extracts of HepG2 cells, and the mode of cell death was detected by Ao/EtBr staining and flow cytometry with PI Annexin- V FITC dual staining. Then, the protein expression of BAX and BCl2 was studied using fluorescent dye to determine the regulation of the BAX and BCl2 genes. We observed that all the three extracts showed the presence of bioactive compounds such as polyphenols or phytochemicals. The W. somnifera bioactive compounds were found to have the highest anti-proliferative activity on human liver cancer cells.


Assuntos
Antineoplásicos Fitogênicos/farmacologia , Antioxidantes/farmacologia , Camellia sinensis/química , Regulação Neoplásica da Expressão Gênica/efeitos dos fármacos , Vitis/química , Withania/química , Alcaloides/química , Alcaloides/isolamento & purificação , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Antioxidantes/química , Antioxidantes/isolamento & purificação , Compostos de Bifenilo/antagonistas & inibidores , Compostos de Bifenilo/química , Morte Celular/efeitos dos fármacos , Flavonoides/química , Flavonoides/isolamento & purificação , Células Hep G2 , Humanos , Picratos/antagonistas & inibidores , Picratos/química , Extratos Vegetais/química , Folhas de Planta/química , Proteínas Proto-Oncogênicas c-bcl-2/genética , Proteínas Proto-Oncogênicas c-bcl-2/metabolismo , Sementes/química , Transdução de Sinais , Taninos/química , Taninos/isolamento & purificação , Terpenos/química , Terpenos/isolamento & purificação , alfa-Amilases/genética , alfa-Amilases/metabolismo , Proteína X Associada a bcl-2/genética , Proteína X Associada a bcl-2/metabolismo
13.
Molecules ; 26(16)2021 Aug 15.
Artigo em Inglês | MEDLINE | ID: mdl-34443531

RESUMO

The aim of the study was to determine the chemical profile, antioxidant properties and antimicrobial activities of Heterotrigona itama bee bread from Malaysia. The pH, presence of phytochemicals, antioxidant properties, total phenolic content (TPC) and total flavonoid content (TFC), as well as antimicrobial activities, were assessed. Results revealed a decrease in the pH of bee bread water extract (BBW) relative to bee bread ethanolic extract (BBE) and bee bread hot water extract (BBH). Further, alkaloids, flavonoids, phenols, tannins, saponins, terpenoids, resins, glycosides and xanthoproteins were detected in BBW, BBH and BBE. Also, significant decreases in TPC, TFC, DPPH activity and FRAP were detected in BBW relative to BBH and BBE. We detected phenolic acids such as gallic acid, caffeic acid, trans-ferulic acid, trans 3-hydroxycinnamic acid and 2-hydroxycinnamic acid, and flavonoids such as quercetin, kaempferol, apigenin and mangiferin in BBE using high-performance liquid chromatography analysis. The strongest antimicrobial activity was observed in Klebsilla pneumonia (MIC50 1.914 µg/mL), followed by E. coli (MIC50 1.923 µg/mL), Shigella (MIC50 1.813 µg/mL) and Salmonella typhi (MIC50 1.617 µg/mL). Bee bread samples possess antioxidant and antimicrobial properties. Bee bread contains phenolic acids and flavonoids, and could be beneficial in the management and treatment of metabolic diseases.


Assuntos
Anti-Infecciosos/farmacologia , Antioxidantes/farmacologia , Abelhas/química , Própole/farmacologia , Alcaloides/química , Animais , Anti-Infecciosos/química , Antioxidantes/química , Cromatografia Líquida de Alta Pressão , Escherichia coli/efeitos dos fármacos , Escherichia coli/patogenicidade , Flavonoides/química , Glicosídeos/química , Himenópteros/química , Fenóis/química , Própole/química , Salmonella typhi/efeitos dos fármacos , Salmonella typhi/patogenicidade , Saponinas/química , Shigella/efeitos dos fármacos , Shigella/patogenicidade , Taninos/química , Terpenos/química
14.
Molecules ; 26(15)2021 Aug 02.
Artigo em Inglês | MEDLINE | ID: mdl-34361835

RESUMO

The present study compared the effects of natural senescence and methyl jasmonate (JA-Me) treatment on the levels of terpene trilactones (TTLs; ginkgolides and bilobalide), phenolic acids, and flavonoids in the primary organs of Ginkgo biloba leaves, leaf blades, and petioles. Levels of the major TTLs, ginkgolides B and C, were significantly higher in the leaf blades of naturally senesced yellow leaves harvested on 20 October compared with green leaves harvested on 9 September. In petioles, a similar effect was found, although the levels of these compounds were almost half as high. These facts indicate the importance of the senescence process on TTL accumulation. Some flavonoids and phenolic acids also showed changes in content related to maturation or senescence. Generally, the application of JA-Me slightly but substantially increased the levels of TTLs in leaf blades irrespective of the difference in its application side on the leaves. Of the flavonoids analyzed, levels of quercetin, rutin, quercetin-4-glucoside, apigenin, and luteolin were dependent on the JA-Me application site, whereas levels of (+) catechin and (-) epicatechin were not. Application of JA-Me increased ferulic acid and p-coumaric acid esters in the petiole but decreased the levels of these compounds in the leaf blade. The content of p-coumaric acid glycosides and caffeic acid esters was only slightly modified by JA-Me. In general, JA-Me application affected leaf senescence by modifying the accumulation of ginkogolides, flavonoids, and phenolic acids. These effects were also found to be different in leaf blades and petioles. Based on JA-Me- and aging-related metabolic changes in endogenous levels of the secondary metabolites in G. biloba leaves, we discussed the results of study in the context of basic research and possible practical application.


Assuntos
Senescência Celular , Ciclopentanos/farmacologia , Flavonoides/metabolismo , Ginkgo biloba/metabolismo , Hidroxibenzoatos/metabolismo , Lactonas/metabolismo , Oxilipinas/farmacologia , Folhas de Planta/metabolismo , Flavonoides/análise , Ginkgo biloba/efeitos dos fármacos , Ginkgo biloba/crescimento & desenvolvimento , Hidroxibenzoatos/análise , Lactonas/análise , Reguladores de Crescimento de Plantas/farmacologia , Folhas de Planta/efeitos dos fármacos , Folhas de Planta/crescimento & desenvolvimento , Terpenos/análise , Terpenos/metabolismo
15.
J Agric Food Chem ; 69(33): 9498-9510, 2021 Aug 25.
Artigo em Inglês | MEDLINE | ID: mdl-34376044

RESUMO

Sesquiterpenes are natural compounds composed of three isoprene units. They represent the largest class of terpene compounds found in plants, and many have remarkable biological activities. Furthermore, sesquiterpenes have broad applications in the flavor, pharmaceutical and biofuel industries due to their complex structures. With the development of metabolic engineering and synthetic biology, the production of different sesquiterpenes has been realized in various chassis microbes. The microbial production of sesquiterpenes provides a promising alternative to plant extraction and chemical synthesis, enabling us to meet the increasing market demand. In this review, we summarized the heterologous production of different plant sesquiterpenes using the eukaryotic yeasts Saccharomyces cerevisiae and Yarrowia lipolytica, followed by a discussion of common metabolic engineering strategies used in this field.


Assuntos
Sesquiterpenos , Yarrowia , Engenharia Metabólica , Saccharomyces cerevisiae/genética , Terpenos , Yarrowia/genética
16.
Int J Mol Sci ; 22(15)2021 Jul 26.
Artigo em Inglês | MEDLINE | ID: mdl-34360730

RESUMO

In recent years, meroterpenoids have found wide biomedical application due to their synthetic availability, low toxicity, and biocompatibility. However, these compounds are not used in targeted drug delivery systems due to their high affinity for cell membranes, both healthy and in cancer cells. Using the approach of creating supramolecular amphiphiles, we have developed self-assembling systems based on water-soluble pillar[5]arene and synthetic meroterpenoids containing geraniol, myrtenol, farnesol, and phytol fragments. The resulting systems can be used as universal drug delivery systems. It was shown by turbidimetry that the obtained pillar[5]arene/synthetic meroterpenoid systems do not interact with the model cell membrane at pH = 7.4, but the associates are destroyed at pH = 4.1. In this case, the synthetic meroterpenoid is incorporated into the lipid bilayer of the model membrane. The characteristics of supramolecular self-assembly, association constants and stoichiometry of the most stable pillar[5]arene/synthetic meroterpenoid complexes were established by UV-vis spectroscopy and dynamic light scattering (DLS). It was shown that supramolecular amphiphiles based on pillar[5]arene/synthetic meroterpenoid systems form monodisperse associates in a wide range of concentrations. The inclusion of the antitumor drug 5-fluoro-2'-deoxyuridine (floxuridine) into the structure of the supramolecular associate was demonstrated by DLS, 19F, 2D DOSY NMR spectroscopy.


Assuntos
Calixarenos/química , Floxuridina/química , Membranas Artificiais , Terpenos/química
17.
Molecules ; 26(16)2021 Aug 04.
Artigo em Inglês | MEDLINE | ID: mdl-34443305

RESUMO

The local botanical Imperata cylindrica in Cameroon was investigated for its antibacterial potency. The methanol extract afforded a total of seven compounds, including five hitherto unreported compounds comprising three flavonoids (1-3) and two C-15 isoprenoid analogues (4 and 5) together with known derivatives (6 and 7). The novelty of the flavonoids was related to the presence of both methyl and prenyl groups. The potential origin of the methyl in the flavonoids is discussed, as well as the chemophenetic significance of our findings. Isolation was performed over repeated silica gel and Sephadex LH-20 column chromatography and the structures were elucidated by (NMR and MS). The crude methanol extract and isolated compounds showed considerable antibacterial potency against a panel of multi-drug resistant (MDR) bacterial strains. The best MIC values were obtained with compound (2) against S. aureus ATCC 25923 (32 µg/mL) and MRSA1 (16 µg/mL).


Assuntos
Antibacterianos/farmacologia , Flavonoides/farmacologia , Poaceae/química , Prenilação , Terpenos/farmacologia , Espectroscopia de Ressonância Magnética Nuclear de Carbono-13 , Flavonoides/química , Flavonoides/isolamento & purificação , Testes de Sensibilidade Microbiana , Espectroscopia de Prótons por Ressonância Magnética , Terpenos/química , Terpenos/isolamento & purificação
18.
Molecules ; 26(16)2021 Aug 13.
Artigo em Inglês | MEDLINE | ID: mdl-34443500

RESUMO

Prostaglandins are a group of important cell-signaling molecules involved in the regulation of ovarian maturation, oocyte development, egg laying and associated behaviors in invertebrates. However, the presence of prostaglandin E2 (PGE2), the key enzymes for PGE2 biosynthesis and its interference by drugs were not investigated previously in the ovary of ticks. The present study was undertaken to assess the modulation of the PGE2-mediated pathway in the eclosion blocking effect of flumethrin and terpenoid subfraction isolated from Artemisia nilagirica in Rhipicephalus annulatus ticks. The acaricidal activities and chemical profiling of the terpenoid subfraction were performed. The localization of the cyclooxygenase1 (COX1) and prostaglandin E synthase (PGES) enzymes and the quantification of PGE2 in the ovaries of the ticks treated with methanol (control), flumethrin and terpenoid subfraction were also undertaken. In addition, the vitellogenin concentration in hemolymph was also assayed. Both flumethrin and the terpenoid subfraction of A. nilagirica elicited a concentration-dependent inhibition of fecundity and blocking of hatching of the eggs. The COX1 could not be detected in the ovaries of treated and control ticks, while there was no significant difference observed in the concentration of vitellogenin (Vg) in them. The presence of PGES in the oocytes of control ticks was confirmed while the immunoreactivities against PGES were absent in the vitellogenic oocytes of ticks treated with flumethrin and terpenoid subfraction. The levels of PGE2 were below the detection limit in the ovaries of the flumethrin-treated ticks, while it was significantly lower in the ovaries of the terpenoid subfraction-treated ticks. Hence, the prostaglandin E synthase and PGE2 were identified as very important mediators for the signaling pathway for ovarian maturation and oviposition in ticks. In addition, the key enzyme for prostaglandin biosynthesis, PGES and the receptors for PGE2 can be exploited as potential drug targets for tick control. The detection of PGES by immunohistochemistry and quantification of PGE2 by LC-MSMS can be employed as valuable tools for screening newer compounds for their eclosion blocking acaricidal effects.


Assuntos
Artemisia/química , Dinoprostona/metabolismo , Piretrinas/farmacologia , Rhipicephalus/efeitos dos fármacos , Terpenos/isolamento & purificação , Terpenos/farmacologia , Animais , Anticorpos/metabolismo , Feminino , Cromatografia Gasosa-Espectrometria de Massas , Hemolinfa/metabolismo , Imersão , Ovário/efeitos dos fármacos , Ovário/enzimologia , Peroxidase/metabolismo , Prostaglandina-E Sintases/metabolismo , Vitelogeninas/metabolismo
19.
Food Res Int ; 147: 110487, 2021 09.
Artigo em Inglês | MEDLINE | ID: mdl-34399483

RESUMO

Terpenes are a major class of natural aromatic compounds in grapes and wines to offer the characteristic flavor and aroma, serving as important quality traits of wine products. Saccharomyces cerevisiae represents an excellent cell factory platform for large-scale bio-based terpene production. This review describes the biosynthetic pathways of terpenes in different organisms. The metabolic engineering of S. cerevisiae for promoting terpene biosynthesis and the alternative microbial engineering platforms including filamentous fungi and Escherichia coli are also elaborated. Additionally, the potential applications of the terpene products from engineered microorganisms in food and beverage industries are also discussed. This review provides comprehensive information for an innovative supply way of terpene via microbial cell factory, which could facilitate the development and application of this technique at the industrial scale.


Assuntos
Saccharomyces cerevisiae , Terpenos , Bactérias/genética , Indústria Alimentícia , Fungos/genética , Engenharia Metabólica , Saccharomyces cerevisiae/genética
20.
Molecules ; 26(16)2021 Aug 06.
Artigo em Inglês | MEDLINE | ID: mdl-34443354

RESUMO

If plasma polymer thin films are to be synthesised from sustainable and natural precursors of chemically heterogeneous composition, it is important to understand the extent to which this composition influences the mechanism of polymerisation. To this end, a well-studied monoterpene alcohol, terpinen-4-ol, has been targeted for a comparative study with the naturally occurring mix of terpenes (viz. Melaleuca alternifolia oil) from which it is commonly distilled. Positive ion mode mass spectra of both terpinen-4-ol and M. alternifolia oil showed a decrease in disparities between the type and abundance of cationic species formed in their respective plasma environments as applied plasma power was increased. Supplementary biological assay revealed the antibacterial action of both terpinen-4-ol and M. alternifolia derived coatings with respect to S. aureus bacteria, whilst cytocompatibility was demonstrated by comparable eukaryotic cell adhesion to both coatings. Elucidating the processes occurring within the reactive plasmas can enhance the economics of plasma polymer deposition by permitting use of the minimum power, time and precursor pre-processing required to control the extent of monomer fragmentation and fabricate a film of the desired thickness and functionality.


Assuntos
Antibacterianos/química , Antibacterianos/farmacologia , Produtos Biológicos/química , Gases em Plasma/química , Staphylococcus aureus/efeitos dos fármacos , Terpenos/química , Terpenos/farmacologia , Melaleuca/química
SELEÇÃO DE REFERÊNCIAS
DETALHE DA PESQUISA
...