RESUMO
We present a novel solid form of monascin, an azaphilonoid derivative extracted from Monascus purpureus-fermented rice. The crystal structure, C21H26O5, was characterized by single-crystal X-ray diffraction and belongs to the orthorhombic space group P212121. To gain insight into the electronic properties of the short contacts in the crystalline state of monascin, we utilized the Experimental Library of Multipolar Atom Model 2 (ELMAM2) database to transfer the electron density of monascin in its crystalline state. Hirshfeld surface analysis, fingerprint analysis, electronic properties and energetic characterization reveal that intermolecular C-H...O hydrogen bonds play a crucial role in the noncovalent bonding interactions by connecting molecules into two- and three-dimensional networks. The molecular electrostatic potential (MEP) map of the monascin molecule demonstrates that negatively charged regions located at four O atoms are favoured binding sites for more positively charged amino acid residues during molecular recognition. In addition, powder X-ray diffraction confirms that no transformation occurs during the crystallization of monascin.
Assuntos
Ligação de Hidrogênio , Monascus , Oryza , Monascus/química , Monascus/metabolismo , Cristalografia por Raios X , Oryza/química , Fermentação , Compostos Heterocíclicos com 3 Anéis/química , Estrutura Molecular , Modelos Moleculares , Extratos Vegetais/química , Eletricidade EstáticaRESUMO
Citrinin is a hepato-nephrotoxic mycotoxin produced by fungal species. The Monascus purpureus fungus plays a crucial role in the fermentation of red rice to produce red yeast rice-based food supplements, which represent the primary source of human exposure to citrinin. In this study, a simple and sensitive analytical method was successfully developed and validated for the citrinin determination in these products. The extraction process involved a QuEChERS (Quick, Easy, Cheap, Effective, Rugged, and Safe) step and citrinin determination by ultra high-performance liquid chromatography coupled with tandem mass spectrometry (UHPLC-MS/MS). The proposed method provided satisfactory linearity, percentage of recovery from 82 to 104% with relative standard deviations (RSD) lower than 14%, and limits of detection and quantification of 0.07 µg/Kg and 0.24 µg/kg, respectively. Among the 14 samples analyzed, citrinin was found in two red rice samples (0.24 and 0.46 µg/kg) and in six food supplements (from 0.44 to 87 µg/kg).
Assuntos
Citrinina , Suplementos Nutricionais , Contaminação de Alimentos , Oryza , Espectrometria de Massas em Tandem , Citrinina/análise , Espectrometria de Massas em Tandem/métodos , Cromatografia Líquida de Alta Pressão , Suplementos Nutricionais/análise , Oryza/química , Oryza/microbiologia , Contaminação de Alimentos/análise , Monascus/metabolismo , Monascus/química , Produtos Biológicos/análise , Produtos Biológicos/químicaRESUMO
The fungus Monascus is a well-known source of secondary metabolites with interesting pharmaceutical and nutraceutical applications. In particular, Monascus pigments possess a wide range of biological activities (e.g. antimicrobial, antioxidant, anti-inflammatory or antitumoral). To broaden the scope of their possible application, this study focused on testing Monascus pigment extracts as potential photosensitizing agents efficient in antimicrobial photodynamic therapy (aPDT) against bacteria. For this purpose, eight different extracts of secondary metabolites from the liquid- and solid-state fermentation of Monascus purpureus DBM 4360 and Monascus sp. DBM 4361 were tested against Gram-positive and Gram-negative model bacteria, Bacillus subtilis and Escherichia coli and further screened for ESKAPE pathogens, Staphylococcus aureus and Pseudomonas aeruginosa. To the bacterial culture, increasing concentration of extracts was added and it was found that all extracts showed varying antimicrobial activity against Gram-positive bacteria in dark, which was further increased after irradiation. Gram-negative bacteria were tolerant to the extracts' exposure in the dark but sensitivity to almost all extracts that occurred after irradiation. The Monascus sp. DBM 4361 extracts seemed to be the best potential candidate for aPDT against Gram-positive bacteria, being efficient at low doses, i.e. the lowest total concentration of Monascus pigments exhibiting aPDT effect was 3.92 ± 1.36 mg/L for E. coli. Our results indicate that Monascus spp., forming monascuspiloin as the major yellow pigment and not-forming mycotoxin citrinin, is a promising source of antimicrobials and photoantimicrobials.
Assuntos
Antibacterianos , Testes de Sensibilidade Microbiana , Monascus , Micélio , Monascus/química , Monascus/metabolismo , Antibacterianos/farmacologia , Antibacterianos/química , Micélio/química , Micélio/efeitos da radiação , Micélio/efeitos dos fármacos , Fármacos Fotossensibilizantes/farmacologia , Fármacos Fotossensibilizantes/química , Produtos Biológicos/farmacologia , Produtos Biológicos/química , Bactérias Gram-Positivas/efeitos dos fármacos , Bactérias Gram-Positivas/efeitos da radiação , Misturas Complexas/farmacologia , Misturas Complexas/química , Pigmentos Biológicos/farmacologia , FotoquimioterapiaRESUMO
In recent years, the considerable potential of endophytic bacteria and fungi as prolific producers of exopolysaccharides (EPSs) have attracted interest. In this study, 56 endophytes were isolated from Cyclocarya paliurus, and the secondary metabolites of EPSs were extracted from Monascus purpureus, Penicillium citrinum and Aspergillus versicolor, screened, and named MPE, PCE and AVE, respectively. In this work, the physicochemical properties and antioxidant activities of three EPSs, their cell proliferation activity on IEC-6 and RAW264.7 were investigated. The three EPSs were mainly composed of neutral sugar and differ in microstructure. However, MPE had a loose structure, and PCE exhibited a dense and sheet-like structure. In addition, the three EPSs performed ordinary antioxidant activity in vitro but showed excellent cell proliferation activity on IEC-6 and RAW264.7. The cell proliferation activity of PCE was 1.4-fold that of the controls at a concentration of 800 µg/mL on IEC-6, and MPE exhibited 1.3-fold increase on RAW264.7. This study provided scientific evidence and insights into the application of endophytes as a novel plant resource possessing huge application potential.
Assuntos
Antioxidantes , Proliferação de Células , Endófitos , Juglandaceae , Penicillium , Camundongos , Animais , Antioxidantes/farmacologia , Antioxidantes/química , Células RAW 264.7 , Endófitos/química , Endófitos/metabolismo , Proliferação de Células/efeitos dos fármacos , Juglandaceae/química , Penicillium/química , Penicillium/metabolismo , Aspergillus/química , Aspergillus/metabolismo , Polissacarídeos Fúngicos/química , Polissacarídeos Fúngicos/farmacologia , Polissacarídeos Fúngicos/isolamento & purificação , Monascus/química , Monascus/metabolismo , RatosRESUMO
Pear residue, a byproduct of pear juice extraction, is rich in soluble sugar, vitamins, minerals, and cellulose. This study utilized Monascus anka in liquid fermentation to extract dietary fiber (DF) from pear residue, and the structural and functional characteristics of the DF were analyzed. Soluble DF (SDF) content was increased from 7.9/100 g to 12.6 g/100 g, with a reduction of average particle size from 532.4 to 383.0 nm by fermenting with M. anka. Scanning electron microscopy and infrared spectroscopic analysis revealed more porous and looser structures in Monascus pear residue DF (MPDF). Water-, oil-holding, and swelling capacities of MPDF were also enhanced. UV-visible spectral analysis showed that the yield of yellow pigment in Monascus pear residue fermentation broth (MPFB) was slightly higher than that in the Monascus blank control fermentation broth. The citrinin content in MPFB and M. anka seed broth was 0.90 and 0.98 ug/mL, respectively. Therefore, liquid fermentation with M. anka improved the structural and functional properties of MPDF, suggesting its potential as a functional ingredient in food.
Assuntos
Fibras na Dieta , Fermentação , Monascus , Pyrus , Monascus/metabolismo , Monascus/química , Fibras na Dieta/análise , Pyrus/química , Pigmentos Biológicos/análise , Citrinina/análise , Frutas/química , Microscopia Eletrônica de Varredura , Tamanho da PartículaRESUMO
Three new monacolin analogues, 3,6-dihydroxy-monacolin P (1), 6-methoxy monacolin S (2), and 6-methoxy dehydromonacolin S (3), were isolated from a fraction that strongly inhibited 3-hydroxy-3-methylglutaryl-CoA reductase from the ethyl acetate portion of red yeast rice ethanol extract. Their structures were determined through a combination of 1D and 2D NMR experiments, mass spectrometry analysis, and known literature reports.
Assuntos
Espectroscopia de Ressonância Magnética , Monascus , Monascus/química , Estrutura Molecular , Inibidores de Hidroximetilglutaril-CoA Redutases/química , Hidroximetilglutaril-CoA Redutases/química , Hidroximetilglutaril-CoA Redutases/metabolismo , Produtos BiológicosRESUMO
BACKGROUND: Monascus pigment (MP) is a natural food coloring with vital physiological functions but prone to degradation and color fading under light conditions. RESULTS: This study investigated the effect of complex formation of soybean protein isolate (SPI), maltodextrin (MD), and MP on the photostability of MP. Light stability was assessed through retention rate and color difference. Fluorescence spectroscopy (FS), circular dichroism (CD), Fourier-transform infrared (FTIR) spectroscopy, and X-ray diffraction (XRD) explored MP, SPI, and MD interactions, clarifying the MP-SPI-MD complex mechanism on the light stability of MP. Microstructure and differential scanning calorimetry (DSC) analyzed the morphology and thermal properties. The retention rate of MP increased to approximately 80%, and minimal color difference was observed when adding SPI and MD simultaneously. FS revealed hydrophobic interaction between MP and SPI. FTIR analysis showed intensity changes and peak shifts in amide I band and amide II band, which proved the hydrophobic interaction. CD showed a decrease in α-helix content and an increase in ß-sheet content after complex formation, indicating strengthened hydrogen bonding interactions. Scanning electron microscopy (SEM) analysis demonstrated that MP was attached to the surface and interior of complexes. XRD showed MP as crystalline, while SPI and MD were amorphous, complexes exhibited weakened or absent peaks, suggesting MP encapsulation. The results of DSC were consistent with XRD. CONCLUSION: SPI and MD enveloped MP through hydrogen bonding and hydrophobic interaction, ultimately enhancing its light stability and providing insights for pigment-protein-polysaccharide interactions and improving pigment stability in the food industry. © 2024 Society of Chemical Industry.
Assuntos
Monascus , Pigmentos Biológicos , Polissacarídeos , Proteínas de Soja , Proteínas de Soja/química , Monascus/química , Monascus/metabolismo , Polissacarídeos/química , Pigmentos Biológicos/química , Difração de Raios X , Espectroscopia de Infravermelho com Transformada de Fourier , Dicroísmo Circular , Interações Hidrofóbicas e Hidrofílicas , Varredura Diferencial de Calorimetria , Corantes de Alimentos/químicaRESUMO
Monascus is a filamentous fungus that has been used in the food and pharmaceutical industries. When used as an auxiliary fermenting agent in the manufacturing of cheese, Monascus cheese is obtained. Citrinin (CIT) is a well-known hepatorenal toxin produced by Monascus that can harm the kidneys structurally and functionally and is frequently found in foods. However, CIT contamination in Monascus cheese is exacerbated by the metabolic ability of Monascus to product CIT, which is not lost during fermentation, and by the threat of contamination by Penicillium spp. that may be introduced during production and processing. Considering the safety of consumption and subsequent industrial development, the CIT contamination of Monascus cheese products needs to be addressed. This review aimed to examine its occurrence in Monascus cheese, risk implications, traditional control strategies, and new research advances in prevention and control to guide the application of biotechnology in the control of CIT contamination, providing more possibilities for the application of Monascus in the cheese industry.
Assuntos
Queijo , Citrinina , Contaminação de Alimentos , Monascus , Monascus/metabolismo , Monascus/química , Queijo/microbiologia , Queijo/análise , Citrinina/análise , Contaminação de Alimentos/análise , Contaminação de Alimentos/prevenção & controle , Humanos , FermentaçãoRESUMO
Red koji polysaccharides, derived from the fermentation of Monascus, have been recognized for their health-enhancing properties. This article reviews their structural characteristics, biosynthesis pathways, and biological activities. It emphasizes the need for sustainable practices in fermentation and the optimization of extraction methods for scalable production. The significance of exploring the molecular mechanisms involved in their biosynthesis is also highlighted to enhance yield and efficiency. Research indicates that red koji polysaccharides possess diverse biological functions, beneficial for pharmaceutical applications due to their health benefits and minimal toxicity. The review points out the necessity for more detailed studies on key enzymes and genes in biosynthesis to improve production methods. It also identifies the current challenges in production scalability and extraction efficiency. Furthermore, while these polysaccharides show potential in pharmaceuticals, their clinical efficacy and mechanism of action in human subjects require further investigation. The review briefly explores potential structural modifications to improve their biological activities. The review concludes that red koji polysaccharides hold significant untapped potential, particularly in drug formulation. Future research should focus on overcoming current production and application challenges, including conducting clinical trials to validate their efficacy and exploring structural modifications for enhanced therapeutic benefits. This comprehensive understanding of red koji polysaccharides paves the way for their expanded application in the pharmaceutical industry. © 2024 Society of Chemical Industry.
Assuntos
Monascus , Polissacarídeos , Humanos , Polissacarídeos/farmacologia , Polissacarídeos/química , Polissacarídeos/isolamento & purificação , Polissacarídeos/biossíntese , Monascus/metabolismo , Monascus/química , Monascus/genética , Animais , FermentaçãoRESUMO
The natural pigment of monascus is favored by human for its special coloring and physiological activity, and its development and application have attracted much attention. In this study, a novel corn oil-based nanoemulsion encapsulated with Yellow Monascus Pigment crude extract (CO-YMPN) was successfully prepared via the phase inversion composition method. The fabrication and stable conditions of the CO-YMPN including Yellow Monascus pigment crude extract (YMPCE) concentration, emulsifier ratio, pH, temperature, ionic strength, monochromatic light and storage time were investigated systemically. The optimized fabrication conditions were the emulsifier ratio (5:3 ratio of Tween 60 to Tween 80) and the YMPCE concentration (20.00% wt%)). Additionally, the DPPH radical scavenging capability of the CO-YMPN (19.47 ± 0.52%) was more excellent than each YMPCE or corn oil. Moreover, the kinetic analysis results based on Michaelis-Menten equation and constant revealed that CO-YMPN could improve lipase hydrolysis capacity. Therefore, the CO-YMPN complex had excellent storage stability and water solubility in the final water system, and the YMPCE showed brilliant stability.
Assuntos
Monascus , Pigmentos Biológicos , Humanos , Pigmentos Biológicos/química , Monascus/química , Óleo de Milho , Hidrólise , Cinética , Polissorbatos , Emulsificantes , Água , Digestão , LipaseRESUMO
Monascus fermented rice, also known as red yeast rice, exhibits a broad spectrum of biological activities due to its chemical constituents, such as monacolins and azaphilone pigments. Here, we cultured Monascus kaoliang KB9 in a liquid malt medium instead of on rice as a carbon source. Eleven known compounds (1-11) containing azaphilones and their early intermediate were isolated and identified. However, this was the first time that angular tricyclic azaphilones, monasfluols A (4) and B (7), acetyl-monasfluol A (5) and monasfluore A (6), were isolated from this species. Interestingly, all isolated tricyclic azaphilones existed exclusively in enol form in CD3OD, as evidenced by NMR spectroscopy. The absolute configuration of compounds 4-7 was also first experimentally identified based on ECD spectroscopy combined with conformational analyses using computational techniques. The assigned stereochemistry of Monascus azaphilones in this work provides essential structural information that will benefit future biological and pharmaceutical investigations.
Assuntos
Monascus , Monascus/química , Solventes , Benzopiranos/farmacologia , Benzopiranos/química , Pigmentos Biológicos/químicaRESUMO
Two orange pigments, rubropunctatin (1) and monascorubrin (2), along with the yellow pigments, monascin (3) and ankaflavin (4), were isolated from M. kaoliang KB9-fermented rice, also known as red yeast rice. The orange pigments exhibit a broad spectrum of biological activities and appeared to be the major components of this fermented rice. In this work, quantitative 1H NMR (qHNMR) and 13C NMR experiments were used to determine the amounts of the two orange pigments in a crude extract in which most of the 1H NMR signals of the two compounds were indistinguishable. The quantitative values obtained by NMR techniques were found to be similar to those obtained by HPLC. Thus, the combined qHNMR with 13C experiment described in this work could be further developed to quantifying Monascus pigments or other invaluable natural products when qHNMR alone is insufficient for quantitative analysis.
Assuntos
Monascus , Pigmentos Biológicos , Cromatografia Líquida de Alta Pressão , Fermentação , Espectroscopia de Ressonância Magnética , Monascus/química , Pigmentos Biológicos/químicaRESUMO
Monascus rice (MR) and highland barley monascus (HBM), the monascus fermented products, are applied in food and medicine to reduce cholesterol and promote digestion. Due to the fermentation substrates, their compositions are different. However, the exact differences have not been reported to date. By UPLC-Q-Orbitrap HRMS analysis, multiple components of twenty batches of MR and HBM samples were identified. In total, 100 components were confirmed (e.g., monacolins, pigments, decalin derivatives, amino acids). Then, principal component analysis (PCA) and orthogonal partial least squares-discriminant analysis (OPLS-DA) were used to filter the components of MR and HBM. In the PCA model, 88.1% of the total variance was uncovered. The OPLS-DA model showed better discrimination between MR and HBM, and the values of R2X, R2Y, and Q2 were 0.837, 0.996, and 0.956, respectively. Based on the value of the variable importance in projection (VIP) and the result of the t-test, 424 components (VIP > 1, p < 0.05) were acquired. Finally, 11 differential components were selected as the characteristic compounds to discriminate between MR and HBM: the content of 9 monacolins (3-hydroxy-3,5-dihydrodehydromonacolin K, monacolin K, dehydromonacolin K, dehydromonacolin J hydroxy acid, monacophenyl, dihydromonacolin J hydroxy acid, monacolin L, dehydromonacolin J, and monacolin R) in HBM was higher than the content in MR, but the content of 2 pigments (ankaflavin and monascin) was lower in HBM and higher in MR. The findings revealed the similarities and differences in the chemical composition between MR and HBM, which is expected to provide a basis for quality control of HBM.
Assuntos
Hordeum , Monascus , Oryza , Fermentação , Hidroxiácidos/metabolismo , Lovastatina/análise , Monascus/química , Oryza/químicaRESUMO
A polysaccharide (EMP) was prepared from Monascus purpureus 40,269 through liquid fermentation, and its immunoregulatory effect was investigated to find clues regarding its potential applicability. Structural characterization demonstrated that EMP, with a molecular weight of 83.1 kDa, consists of Xyl, Man, Gal, Ara, Rha, Glc, GalA, and GlcA at a molar ratio of 2.6: 22: 35.1: 7: 1: 29.2: 2.7: 0.6. Immunomodulatory assays involving RAW264.7 cells indicated that EMP exhibits significantly enhanced pinocytic and phagocytic capacities and promotes the secretion of reactive oxygen species, nitric oxide, and cytokines (interleukin-1ß, tumor necrosis factor-α, and interleukin-6) by activating RAW264.7 cells. Moreover, EMP is recognized by Toll-like receptor 4 (TLR-4) and has an immunomodulatory effect by activating the mitogen-activated protein kinase (MAPK) and nuclear factor-kappa B (NF-κB) signaling pathways in RAW264.7 cells. Collectively, these results demonstrate that EMP could be used as a functional food for immunological reagents.
Assuntos
Sistema de Sinalização das MAP Quinases , Monascus , NF-kappa B , Polissacarídeos , Receptores de Laminina , Receptor 4 Toll-Like , Animais , Fermentação , Fatores Imunológicos/química , Fatores Imunológicos/farmacologia , Sistema de Sinalização das MAP Quinases/efeitos dos fármacos , Camundongos , Proteínas Quinases Ativadas por Mitógeno/metabolismo , Monascus/química , Monascus/metabolismo , NF-kappa B/metabolismo , Polissacarídeos/química , Polissacarídeos/farmacologia , Células RAW 264.7 , Transdução de Sinais/efeitos dos fármacos , Receptor 4 Toll-Like/metabolismoRESUMO
Highland barley Monascus has historically been used in solid state fermentation and traditional fermented foods in Tibet. It is possessed of the characteristics of medicine and food. Three new 8,13-unsaturated benzocyclodiketone-conjugated Monascus pigments (1-3), three new benzofuran Monascus pigments (4-6), three new butylated malonyl Monascus pigments (7-9), and eleven known Monascus pigment derivatives (10-20) were isolated from highland barley Monascus for the first time. Their structures were determined by analyzing NMR, MS, UV, and IR spectral data and compared with relevant references. Among them, compounds 2, 4, 6 showed important inhibition of pancreatic lipase activity, and decreased significantly FFA-induced lipid accumulation in HepG2 liver cells. Additionally, compounds 1, 10, 14, 16, 18 exhibited certain hepatoprotective activities against the damage in acetaminophen-induced HepG2 cells. The plausible biogenetic pathway and preliminary structure activity relationship of the selected compounds were scientifically summarized and discussed in this work.
Assuntos
Hipolipemiantes/química , Fígado/efeitos dos fármacos , Monascus/química , Pigmentos Biológicos/química , Cromatografia Gasosa-Espectrometria de Massas , Hordeum/microbiologia , Hipolipemiantes/isolamento & purificação , Hipolipemiantes/farmacologia , Espectrometria de Massas , Pigmentos Biológicos/isolamento & purificação , Pigmentos Biológicos/farmacologia , Espectrometria de Massas por Ionização por Electrospray , Espectrofotometria Ultravioleta , Espectroscopia de Infravermelho com Transformada de Fourier , Relação Estrutura-AtividadeRESUMO
Monascus pigments are a kind of high-quality natural edible pigments fermented by Monascus filamentous fungi, which have been widely used in food, cosmetics, medicine, textiles, dyes and chemical industries as active functional ingredients. Moreover, Monascus pigments have a good application prospect because of a variety of biological functions such as antibacterial, antioxidation, anti-inflammatory, regulating cholesterol, and anti-cancer. However, the low productivity and color value of pigments restrict their development and application. In this review, we introduced the categories, structures, biosynthesis and functions of Monascus pigments, and summarized the current methods for improving the productivity and color value of pigments, including screening and mutagenesis of strains, optimization of fermentation conditions, immobilized fermentation, mixed fermentation, additives, gene knockout and overexpression technologies, which will help to develop the foundation for the industrial production of Monascus pigments.
Assuntos
Monascus , Antioxidantes , Fermentação , Monascus/química , Pigmentação , Pigmentos BiológicosRESUMO
Alcohol metabolism causes an excessive accumulation of liver lipids and inflammation, resulting in liver damage. The yellow pigments monascin (MS) and ankaflavin (AK) of Monascus purpureus-fermented rice were proven to regulate ethanol-induced damage in HepG2 cells, but the complete anti-inflammatory and anti-fatty liver mechanisms in the animal model are still unclear. This study explored the roles of MS and AK in improving alcoholic liver injury. MS and AK were simultaneously fed to evaluate their effects and mechanisms in C57BL/6J mice fed the Lieber-DeCarli liquid alcohol diet for 6 weeks. The results indicated that MS and AK significantly reduced the serum aspartate aminotransferase and alanine aminotransferase activity, as well as the total liver cholesterol and triglyceride levels. The histopathological results indicated that MS and AK prevented lipid accumulation in the liver. MS and AK effectively enhanced the activity of antioxidant enzymes and reduced the degree of lipid peroxidation; AK was particularly effective and exhibited a superior preventive effect against alcoholic liver injury and fatty liver. In addition to inhibiting the phosphorylation of the MAPK family, MS and AK directly reduced TNF-α, IL-6, and IL-1ß levels, thereby reducing NF-κB and its downstream iNOS and COX-2 expressions, as well as increasing PPAR-γ, Nrf-2, and HO-1 expressions to prevent liver damage. MS and AK also directly reduced TNF-α, IL-6, and IL-1ß expression, thereby reducing the production of NF-κB and its downstream iNOS and COX-2, and increasing PPAR-γ, Nrf-2, and HO-1 expressions, preventing alcohol damage to the liver.
Assuntos
Proteínas Quinases Ativadas por AMP/metabolismo , Anti-Inflamatórios/farmacologia , Antioxidantes/farmacologia , Flavinas/farmacologia , Compostos Heterocíclicos com 3 Anéis/farmacologia , Hepatopatias Alcoólicas/tratamento farmacológico , Monascus/química , Proteínas Quinases Ativadas por AMP/genética , Animais , Depressores do Sistema Nervoso Central/toxicidade , Etanol/toxicidade , Metabolismo dos Lipídeos , Hepatopatias Alcoólicas/etiologia , Hepatopatias Alcoólicas/metabolismo , Hepatopatias Alcoólicas/patologia , Masculino , Camundongos , Camundongos Endogâmicos C57BLRESUMO
The mold Monascus has been used as a natural food coloring agent and food additive for more than 1000 years in Asian countries. In Chinese herbology, it was also used for easing digestion and antiseptic effects. Through a thorough investigation of a citrinin-free strain: M. purpureus BCRC 38110, four azaphilones, three benzenoids, one benzofuranone, one 5',6'-dihydrospiro[isochromane-1,2'-pyran]-4'(3'H)-one derivative, two steroids, and six tetralones have been successfully identified. Among them, monapyridine A (1), monatetralones A-E (2-6), and monabenzofuranone (7) were first reported. Their structures were characterized by 1D and 2D NMR, UV, IR, and HRESIMS analyses. With a series of bioactivity screening, monascuspirolide B (14) and ergosterol peroxide (16) exhibited concentration-dependent attenuation of the paclitaxel-induced neurite damage of mouse dorsal root ganglion neurons. The interleukin (IL)-1ß-induced release of inflammatory cytokines IL-8 and tumor necrosis factor (TNF)-α in human chondrosarcoma cells was inhibited by monapurpureusone (8) and monascuspirolide B (14). Altogether, M. purpureus BCRC 38110 possessed potentials as natural therapeutics against inflammatory osteoarthritis and paclitaxel-induced neurotoxicity.
Assuntos
Anti-Inflamatórios/isolamento & purificação , Anti-Inflamatórios/farmacologia , Monascus/química , Fármacos Neuroprotetores/isolamento & purificação , Fármacos Neuroprotetores/farmacologia , Animais , Anti-Inflamatórios/química , Linhagem Celular Tumoral , Células Cultivadas , Gânglios Espinais/efeitos dos fármacos , Humanos , Interleucina-1beta/imunologia , Interleucina-8/metabolismo , Camundongos , Estrutura Molecular , Monascus/metabolismo , Crescimento Neuronal/efeitos dos fármacos , Neurônios/efeitos dos fármacos , Fármacos Neuroprotetores/química , Osteoartrite/tratamento farmacológico , Fator de Necrose Tumoral alfa/metabolismoRESUMO
Azaphilones are a family of polyketide-based fungal natural products that exhibit interesting and useful bioactivities. This minireview explores the literature on various characterised azaphilone biosynthetic pathways, which allows for a proposed consensus scheme for the production of the core azaphilone structure, as well as identifying early diversification steps during azaphilone biosynthesis. A consensus understanding of the core enzymatic steps towards a particular family of fungal natural products can aid in genome-mining experiments. Genome mining for novel fungal natural products is a powerful technique for both exploring chemical space and providing new insights into fungal natural product pathways.
Assuntos
Produtos Biológicos/metabolismo , Monascus/química , Pigmentos Biológicos/biossíntese , Benzopiranos/química , Produtos Biológicos/química , Estrutura Molecular , Monascus/metabolismo , Pigmentos Biológicos/químicaRESUMO
Alkaline extracted endopolysaccharides (MPS) from Monascus purpureus (Hong Qu) mycelium were successfully separated into four sub-fractions, namely MPS-1 (18.0 %), MPS-2 (27.1 %), MPS-3 (12.6 %) and MPS-4 (14.7 %), by DEAE-Cellulose column chromatography. By combining monosaccharide composition analysis, methylation analysis and 1D & 2D NMR, the structure of sub-fractions was systematically characterized. Both MPS-1 and MPS-2 were comprised of mannose, glucose and galactose in the molar ratio of 1.5:1.6:1.0 and 10.6:1.0:13.8, respectively. The backbone of them both consisted of 2-α-Manp with several different branched chains. However, MPS-1 contained glucose based sugar residues such as 3-Glcp and 4-Glcp which were not shown on MPS-2. The proposed structures of MPS-3 and MPS-4 were not obtained due to the fairly complex molecular structure and relatively low yield. Moreover, based on the RAW 264.7 cells model, MPS-2 could significantly promote cytokines secretion including IL-6, TNF-α, and IL-10 and improve expression levels of the related mRNA.