RESUMO
BACKGROUND AND AIMS: In the subfamily Poöideae (Poaceae), certain grass species possess anti-herbivore alkaloids synthesized by fungal endophytes that belong to the genus Epichloë (Clavicipitaceae). The protective role of these symbiotic endophytes can vary, depending on alkaloid concentrations within specific plant-endophyte associations and plant parts. METHODS: We conducted a literature review to identify articles containing alkaloid concentration data for various plant parts in six important pasture species, Lolium arundinaceum, Lolium perenne, Lolium pratense, Lolium multiflorum|Lolium rigidum and Festuca rubra, associated with their common endophytes. We considered the alkaloids lolines (1-aminopyrrolizidines), peramine (pyrrolopyrazines), ergovaline (ergot alkaloids) and lolitrem B (indole-diterpenes). While all these alkaloids have shown bioactivity against insect herbivores, ergovaline and lolitrem B are harmful for mammals. KEY RESULTS: Loline alkaloid levels were higher in the perennial grasses L. pratense and L. arundinaceum compared to the annual species L. multiflorum and L. rigidum, and higher in reproductive tissues than in vegetative structures. This is probably due to the greater biomass accumulation in perennial species that can result in higher endophyte mycelial biomass. Peramine concentrations were higher in L. perenne than in L. arundinaceum and not affected by plant part. This can be attributed to the high within-plant mobility of peramine. Ergovaline and lolitrem B, both hydrophobic compounds, were associated with plant parts where fungal mycelium is usually present, and their concentrations were higher in plant reproductive tissues. Only loline alkaloid data were sufficient for below-ground tissue analyses and concentrations were lower than in above-ground parts. CONCLUSIONS: Our study provides a comprehensive synthesis of fungal alkaloid variation across host grasses and plant parts, essential for understanding the endophyte-conferred defence extent. The patterns can be understood by considering endophyte growth within the plant and alkaloid mobility. Our study identifies research gaps, including the limited documentation of alkaloid presence in roots and the need to investigate the influence of different environmental conditions.
Assuntos
Alcaloides , Endófitos , Epichloe , Festuca , Lolium , Poliaminas , Alcaloides/metabolismo , Alcaloides/análise , Endófitos/química , Endófitos/fisiologia , Epichloe/química , Epichloe/fisiologia , Ergotaminas/metabolismo , Festuca/microbiologia , Festuca/fisiologia , Herbivoria , Compostos Heterocíclicos com 2 Anéis , Alcaloides Indólicos/metabolismo , Lolium/microbiologia , Lolium/fisiologia , Micotoxinas , Defesa das Plantas contra Herbivoria , Poaceae/microbiologia , Poaceae/metabolismo , SimbioseRESUMO
Indigo is a bis-indolic alkaloid that has antioxidant and anti-inflammatory effects reported in literature and is a promissory compound for treating chronic inflammatory diseases. This fact prompted to investigate the effects of this alkaloid in the experimental model of Duchenne muscular dystrophy. The main aim of this study was to evaluate the potential role of the indigo on oxidative stress and related signaling pathways in primary skeletal muscle cell cultures and in the diaphragm muscle from mdx mice. The MTT and Neutral Red assays showed no indigo dose-dependent toxicities in mdx muscle cells at concentrations analyzed (3.12, 6.25, 12.50, and 25.00 µg/mL). Antioxidant effect of indigo, in mdx muscle cells and diaphragm muscle, was demonstrated by reduction in 4-HNE content, H2O2 levels, DHE reaction, and lipofuscin granules. A significant decrease in the inflammatory process was identified by a reduction on TNF and NF-κB levels, on inflammatory area, and on macrophage infiltration in the dystrophic sample, after indigo treatment. Upregulation of PGC-1α and SIRT1 in dystrophic muscle cells treated with indigo was also observed. These results suggest the potential of indigo as a therapeutic agent for muscular dystrophy, through their action anti-inflammatory, antioxidant, and modulator of SIRT1/PGC-1α pathway.
Assuntos
Distrofia Muscular de Duchenne , Animais , Anti-Inflamatórios/farmacologia , Anti-Inflamatórios/uso terapêutico , Antioxidantes/metabolismo , Modelos Animais de Doenças , Peróxido de Hidrogênio/metabolismo , Índigo Carmim/metabolismo , Índigo Carmim/farmacologia , Índigo Carmim/uso terapêutico , Alcaloides Indólicos/metabolismo , Alcaloides Indólicos/farmacologia , Alcaloides Indólicos/uso terapêutico , Camundongos , Camundongos Endogâmicos mdx , Modelos Teóricos , Músculo Esquelético/metabolismo , Distrofia Muscular de Duchenne/tratamento farmacológico , Transdução de Sinais , Sirtuína 1/metabolismoRESUMO
Six known indole alkaloid derivatives have been isolated for the first time from Bacillus thuringiensis and Bacillus velezensis strains, all of them as building blocks for the synthesis of larger natural products. Their structure was elucidated by a complete spectroscopy. Their biological activities were tested against some Gram-positive and Gram-negative bacteria and three phytopathogenic fungi which cause diseases in important crops, such as Moniliophthora roreri, the causal agent of cacao disease. The results indicated that some compounds had modest antibacterial activity; however, some of them had strong antifungal activity against the probed fungi. This antifungal activity of these compounds has not been reported.
Assuntos
Antibacterianos/isolamento & purificação , Antifúngicos/isolamento & purificação , Bacillus thuringiensis/química , Bacillus/química , Alcaloides Indólicos/isolamento & purificação , Agaricales/efeitos dos fármacos , Antibacterianos/metabolismo , Antibacterianos/farmacologia , Antifúngicos/metabolismo , Antifúngicos/farmacologia , Bacillus/metabolismo , Bacillus thuringiensis/metabolismo , Produtos Biológicos/isolamento & purificação , Produtos Biológicos/metabolismo , Produtos Biológicos/farmacologia , Bactérias Gram-Negativas/efeitos dos fármacos , Bactérias Gram-Positivas/efeitos dos fármacos , Alcaloides Indólicos/metabolismo , Alcaloides Indólicos/farmacologia , Testes de Sensibilidade Microbiana , Estrutura MolecularRESUMO
Microorganisms are able to produce hundreds of unique chemical structures that can be effectively used by the human beings on their own benefit using the products in the chemical industry. Bacteria belonging to Bacillus genera are very good chemical factories capable to synthesize different compounds with a wide variety of activities. In this review, we try to review the compounds with their respective biological activities produced by different species of Bacillus.
Assuntos
Bacillus/metabolismo , Produtos Biológicos/metabolismo , Antibacterianos/química , Antibacterianos/metabolismo , Bacillus/química , Bacteriocinas/química , Bacteriocinas/metabolismo , Produtos Biológicos/química , Vias Biossintéticas , Humanos , Alcaloides Indólicos/química , Alcaloides Indólicos/metabolismo , Inseticidas/química , Inseticidas/metabolismo , Isocumarinas/química , Isocumarinas/metabolismo , Lipopeptídeos/química , Lipopeptídeos/metabolismo , Modelos Moleculares , Peptídeos Cíclicos/química , Peptídeos Cíclicos/metabolismo , Policetídeos/química , Policetídeos/metabolismo , Metabolismo Secundário , Sideróforos/química , Sideróforos/metabolismoRESUMO
Abstract Chaetoglobosin A is an antibacterial compound produced by Chaetomium globosum, with potential application as a biopesticide and cancer treatment drug. The aim of this study was to evaluate the feasibility of utilizing cornstalks to produce chaetoglobosin A by C. globosum W7 in solid-batch fermentation and to determine an optimal method for purification of the products. The output of chaetoglobosin A from the cornstalks was 0.34 mg/g, and its content in the crude extract was 4.80%. Purification conditions were optimized to increase the content of chaetoglobosin A in the crude extract, including the extract solvent, temperature, and pH value. The optimum process conditions were found to be acetone as the extractant, under room temperature, and at a pH value of 13. Under these conditions, a production process of the antifungal chaetoglobosin A was established, and the content reached 19.17%. Through further verification, cornstalks could replace crops for the production of chaetoglobosin A using this new production process. Moreover, the purified products showed great inhibition against Rhizoctonia solani, with chaetoglobosin A confirmed as the main effective constituent (IC50 = 3.88 µg/mL). Collectively, these results demonstrate the feasibility of using cornstalks to synthesize chaetoglobosin A and that the production process established in this study was effective.
Assuntos
Microbiologia Industrial/métodos , Calosidades/microbiologia , Chaetomium/metabolismo , Alcaloides Indólicos/metabolismo , Antifúngicos/metabolismo , Resíduos/análise , Microbiologia Industrial/instrumentação , Calosidades/metabolismo , Estrutura Molecular , Caules de Planta/metabolismo , Caules de Planta/microbiologia , Alcaloides Indólicos/isolamento & purificação , Alcaloides Indólicos/química , Antifúngicos/isolamento & purificação , Antifúngicos/químicaRESUMO
Chaetoglobosin A is an antibacterial compound produced by Chaetomium globosum, with potential application as a biopesticide and cancer treatment drug. The aim of this study was to evaluate the feasibility of utilizing cornstalks to produce chaetoglobosin A by C. globosum W7 in solid-batch fermentation and to determine an optimal method for purification of the products. The output of chaetoglobosin A from the cornstalks was 0.34mg/g, and its content in the crude extract was 4.80%. Purification conditions were optimized to increase the content of chaetoglobosin A in the crude extract, including the extract solvent, temperature, and pH value. The optimum process conditions were found to be acetone as the extractant, under room temperature, and at a pH value of 13. Under these conditions, a production process of the antifungal chaetoglobosin A was established, and the content reached 19.17%. Through further verification, cornstalks could replace crops for the production of chaetoglobosin A using this new production process. Moreover, the purified products showed great inhibition against Rhizoctonia solani, with chaetoglobosin A confirmed as the main effective constituent (IC50=3.88µg/mL). Collectively, these results demonstrate the feasibility of using cornstalks to synthesize chaetoglobosin A and that the production process established in this study was effective.
Assuntos
Antifúngicos/metabolismo , Calosidades/microbiologia , Chaetomium/metabolismo , Alcaloides Indólicos/metabolismo , Microbiologia Industrial/métodos , Antifúngicos/química , Antifúngicos/isolamento & purificação , Calosidades/metabolismo , Alcaloides Indólicos/química , Alcaloides Indólicos/isolamento & purificação , Microbiologia Industrial/instrumentação , Estrutura Molecular , Caules de Planta/metabolismo , Caules de Planta/microbiologia , Resíduos/análiseRESUMO
The natural compound hobartine {systematic name: (1R)-3-[(1S,5S)-(4,4,8-trimethylbicyclo[3.3.1]non-7-en-2-yl)methyl]-2,3-dihydro-1H-indole}, C20H26N2, (I), is an indole alkaloid isolated from Aristotelia chilensis as part of a study of secondary metabolites from Chilean flora. The colourless compound has a tetracyclic structure closely related to the strongly coloured polymorphic structures discussed in Paz et al. [Acta Cryst. (2013), C69, 1509-1512] and Watson et al. [Acta Cryst. (1989), C45, 1322-1324]. The main differences reside in the absence of a keto group in (I) compared with the previous structures, as well as an endo double bond in (I) contrasting with the exo double bond found in the previous structures. The supramolecular structure of (I) in strongly related to the twofold screw axis, around which isolated chains build up, internally linked by an N-H···N hydrogen bond which is the only significant intermolecular interaction present in the structure.
Assuntos
Produtos Biológicos/química , Produtos Biológicos/isolamento & purificação , Alcaloides Indólicos/química , Alcaloides Indólicos/isolamento & purificação , Produtos Biológicos/síntese química , Cristalografia por Raios X , Ligação de Hidrogênio , Alcaloides Indólicos/síntese química , Alcaloides Indólicos/metabolismo , Estrutura MolecularRESUMO
BACKGROUND: Erythrina verna, popularly known as "mulungu", is a Brazilian medicinal plant used to treat anxiety. Erythrina alkaloids have been described in several species of Erythrina, which have biological and therapeutic properties well known that include anxiolytic and sedative effects. METHODS: In this work, in vitro metabolism of erythraline (1), the major spirocyclic alkaloid of Erythrina verna, was studied in the pig cecum model and by biomimetic phase I reactions. The biomimetic reactions were performed with Jacobsen catalyst to produce oxidative metabolites and one metabolite was isolated and evaluated against cancer cells, as HL-60 (promyelocytic leukemia), SF-295 (Glioblastoma) and OVCAR-8 (ovarian carcinoma). RESULTS: Erythraline exhibited no metabolization by the pig microbiota and a main putative metabolite was formed in a biomimetic model using Jacobsen catalyst. This metabolite was isolated and identified as 8-oxo-erythraline (2). Finally, erythraline and the putative metabolite were tested in MTT model and both compounds showed no important cytotoxic activity against tumor cells. CONCLUSIONS: The alkaloid erythraline was not metabolized by intestinal microbiota, but it was possible to identify its oxidative metabolite from biomimetic reactions. So these data are interesting and stimulate other studies involving this alkaloid, since it is present in phytomedicine products and there are not reported data about the metabolism of erythrina alkaloids.
Assuntos
Erythrina/química , Alcaloides Indólicos/metabolismo , Extratos Vegetais/metabolismo , Animais , Ansiedade/tratamento farmacológico , Brasil , Células HL-60 , Humanos , Técnicas In Vitro , Alcaloides Indólicos/farmacologia , Plantas Medicinais , SuínosRESUMO
During our studies concerning endophytic fungi, two indole alkaloids were co-produced with verruculogen by Penicillium brasilianum isolated from Melia azedarach (Meliaceae). The compounds were isolated by the use of combined chromatographic procedures and identified by physical methods, mainly 1D- and 2D-NMR experiments. This article also describes the production of verruculogen TR-2, first described for this species of Penicillium, and a verruculogen TR-2C-11 epimer, that is a novel fungal natural product. The kinetic production of verruculogen and verruculogen TR-2 produced by P. brasilianum were evaluated in order to understand the involvement of verruculogen TR-2 in verruculogen biosynthesis.
Assuntos
Alcaloides Indólicos/metabolismo , Oryza/microbiologia , Penicillium/metabolismo , Cromatografia Líquida , Cinética , Espectrometria de Massas em TandemRESUMO
This review discusses the isolation, structural elucidation, and biological activities of halogenated indole alkaloids obtained from marine invertebrates. Meridianins and related compounds (variolins, psammopemmins, and aplicyanins), as well as aplysinopsins and leptoclinidamines, are focused on. A compilation of the (13)C-NMR spectral data of these selected natural indole alkaloids is also provided.