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1.
Chem Commun (Camb) ; 55(90): 13594-13597, 2019 Nov 07.
Artigo em Inglês | MEDLINE | ID: mdl-31657378

RESUMO

Indole and the anthocyanin orientalin proceed through a unique cascade sequence that leads to nudicaulins I and II in 92% yield. This biomimetic synthesis confirms the biosynthesis proposal for these structurally unprecedented flavoalkaloids that play a key role in the colour range displayed by the Iceland poppy.


Assuntos
Materiais Biomiméticos/síntese química , Papaver/química , Pigmentos Biológicos/síntese química , Materiais Biomiméticos/química , Islândia , Estrutura Molecular , Pigmentos Biológicos/química
2.
World J Microbiol Biotechnol ; 35(9): 138, 2019 Aug 26.
Artigo em Inglês | MEDLINE | ID: mdl-31451937

RESUMO

Monascus azaphilone pigments, including red, orange, and yellow, are world-famous food colorants. However, the pigments produced by different Monascus species vary in yields and compositions. The underlying mechanism is unclear. In this study, four wild-type Monascus strains, namely M. anka M7, M. purpureus M9, M. ruber C100, and M. aurantiacus M15, were selected as research objects according to the diversification of their pigments fermented in the same mediums and conditions. Twenty-three 3 kbp segments (300 bp overlap with adjacent segments) of the pigment gene cluster were amplified, sequenced, and assembled into the DNA sequences of the clusters. The DNA sequences of pigment biosynthetic gene clusters of the four strains showed 99.94% similarity according to the results of multiple alignment. The expression levels of 17 pigment biosynthetic genes of four strains were determined by using real-time quantitative PCR. The transcriptional regulation contributed more than the DNA sequence variation in Monascus pigments metabolism. Our result gives insight into the study of Monascus pigment biosynthesis.


Assuntos
Monascus/genética , Monascus/metabolismo , Pigmentos Biológicos/biossíntese , Transcrição Genética , Sequência de Aminoácidos , Sequência de Bases , Cor , DNA Fúngico/genética , Proteínas Fúngicas/genética , Proteínas Fúngicas/metabolismo , Regulação Fúngica da Expressão Gênica , Variação Genética , Monascus/química , Monascus/classificação , Família Multigênica , Filogenia , Pigmentos Biológicos/química
3.
J Agric Food Chem ; 67(32): 8938-8949, 2019 Aug 14.
Artigo em Inglês | MEDLINE | ID: mdl-31361121

RESUMO

Polymeric pigments formed via ethyl linkages between grape tannins and anthocyanins are important to the development of stable red wine color. To determine the effect of tannin structure on the stability and color properties of ethyl-linked polymeric pigments, tannin fractions with average polymerization between 4 and 43 units were prepared from grape skins and seeds and combined with malvidin-3-glucoside (M3G) in model wine containing acetaldehyde. As tannin molecular mass increased, the reaction rate with M3G increased. Compared with skin tannins of comparable molecular mass, seed tannins reacted more rapidly with M3G but were prone to precipitation. This resulted in a loss of polymeric pigments formed from seed tannins, which was greater as tannin molecular mass increased. Aggregation occurred following the reaction of seed tannin with M3G, concomitant with precipitation. The aggregation-precipitation phenomenon was not observed for skin tannin-derived pigments, indicating a greater stability in solution than those formed from seed tannins.


Assuntos
Acetaldeído/química , Antocianinas/química , Pigmentos Biológicos/química , Extratos Vegetais/química , Sementes/química , Taninos/química , Vitis/química , Precipitação Química , Cor , Frutas/química , Cinética , Peso Molecular , Polimerização , Polímeros/química
4.
Phytochemistry ; 165: 112048, 2019 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-31229789

RESUMO

For the first time, the pigment composition of basidiocarps from the Chilean mushroom Cortinarius pyromyxa was studied under various aspects like phylogeny, chemistry and antibiotic activity. A molecular biological study supports the monotypic position of C. pyromyxa in subgenus Myxacium, genus Cortinarius. Four undescribed diterpenoids, named pyromyxones A-D, were isolated from fruiting bodies of C. pyromyxa. Their chemical structures were elucidated based on comprehensive one- and two-dimensional NMR spectroscopic analysis, ESI-HRMS measurements, as well as X-ray crystallography. In addition, the absolute configurations of pyromyxones A-D were established with the aid of JH,H, NOESY spectra and quantum chemical CD calculation. The pyromyxones A-D possess the undescribed nor-guanacastane skeleton. Tested pyromyxones A, B, and D exhibit only weak activity against gram-positive Bacillus subtilis and gram-negative Aliivibrio fischeri as well as the phytopathogenic fungi Botrytis cinerea, Septoria tritici and Phytophthora infestans.


Assuntos
Antibacterianos/farmacologia , Cortinarius/química , Bactérias Gram-Negativas/efeitos dos fármacos , Bactérias Gram-Positivas/efeitos dos fármacos , Pigmentos Biológicos/farmacologia , Antibacterianos/química , Antibacterianos/isolamento & purificação , Cristalografia por Raios X , Diterpenos/química , Diterpenos/isolamento & purificação , Diterpenos/farmacologia , Testes de Sensibilidade Microbiana , Modelos Moleculares , Estrutura Molecular , Filogenia , Pigmentos Biológicos/química , Pigmentos Biológicos/isolamento & purificação , Teoria Quântica
5.
J Agric Food Chem ; 67(26): 7526-7529, 2019 Jul 03.
Artigo em Inglês | MEDLINE | ID: mdl-31184887

RESUMO

A limitation of the 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging ability (DRSA) due to the presence of pigments and colors in the extracts of plant-based foods was addressed. The pigments present in the test samples absorb in the same wavelength region as the DPPH radicals; this interferes with the elaborate absorbance readings of the DPPH radicals. In this contribution, electron paramagnetic resonance (EPR) spectroscopy for DPPH assay is proposed in order to avoid this limitation. In the EPR-DPPH assay, the underestimation of the radical scavenging abilities of four different pigment-containing extracts was corrected and this reflected up to a 16.1% change compared to the original values. Thus, the EPR-DPPH assay eliminated interference from the pigments coexisting in the reaction medium and improved the accuracy of the DPPH radical scavenging potential of such extracts. The principle of the proposed solution might also be employed in other assays which suffer from pigment interference.


Assuntos
Compostos de Bifenilo/química , Espectroscopia de Ressonância de Spin Eletrônica/métodos , Depuradores de Radicais Livres/química , Picratos/química , Pigmentos Biológicos/química , Extratos Vegetais/química , Beta vulgaris/química , Capsicum/química , Cor , Rubus/química
6.
Food Chem ; 295: 466-474, 2019 Oct 15.
Artigo em Inglês | MEDLINE | ID: mdl-31174783

RESUMO

Physicochemical properties and emulsion stability of octenyl succinic anhydride (OSA)-modified partial waxy rice Baegjinju starches which were made with different OSA additions and the color stability of the encapsulated paprika pigment powder using the OSA starch were investigated. The DSs of the OSA starches ranged from 0.0152 to 0.0269. The band at 3303 cm-1 reduced as the OSA levels increased, but the A-type crystallinity was maintained. The oil absorption and emulsion stability, the short chain (DP6-12) amylopectin, the resistant starch levels, and the peak and final viscosities increased as the OSA levels increased. The encapsulated pigment powder with freeze-drying had higher color stability and better emulsion, and heating stabilities occurred with spray drying and the native pigment. From these results, it is suggested that the OSA-modified Baegjinju rice starch is a good wall material to protect lipophilic carotenoids. The encapsulated pigment powders could be used as stable natural colorants.


Assuntos
Capsicum/química , Oryza/química , Pigmentos Biológicos/química , Amido/análogos & derivados , Amilopectina , Emulsões/química , Liofilização , Extratos Vegetais/química , Pós/química , Espectroscopia de Infravermelho com Transformada de Fourier , Amido/química , Viscosidade
7.
Food Funct ; 10(6): 3161-3171, 2019 Jun 19.
Artigo em Inglês | MEDLINE | ID: mdl-31120462

RESUMO

Ocimum basilicum var. purpurascens (red rubin basil) is a basil variety rich in anthocyanin compounds, commonly used in the food industry as an aromatic plant. In this study, the nutritional and chemical compositions of red rubin basil leaves were analysed, as well as, the antimicrobial activity and hepatotoxicity of their hydroethanolic extract. Carbohydrates were the main macronutrients present, with glucose being the major free sugar. Quinic acid was the most abundant organic acid, while γ-tocopherol was the highest tocopherol isoform found. α-Linolenic acid was the major fatty acid of the twenty identified compounds. Regarding polyphenols, twenty-six molecules were identified (thirteen non-anthocyanin and thirteen anthocyanin compounds), with rosmarinic acid being the main non-anthocyanin molecule and cyanidin-3-(6,6'-di-p-coumaroyl)-sophoroside-5-glcucoside the most abundant anthocyanin. These compounds could be related to the antimicrobial activity observed in this study. Thus, this variety could be considered a good source of value added molecules for the food industry.


Assuntos
Corantes de Alimentos/química , Ocimum basilicum/química , Pigmentos Biológicos/química , Extratos Vegetais/química , Folhas de Planta/química , Corantes de Alimentos/isolamento & purificação , Indústria Alimentícia , Pigmentos Biológicos/isolamento & purificação , Extratos Vegetais/isolamento & purificação
8.
Mar Drugs ; 17(5)2019 Apr 28.
Artigo em Inglês | MEDLINE | ID: mdl-31035362

RESUMO

Three new azaphilone alkaloids containing glutamine residues, namely N-glutarylchaetoviridins A-C (1-3), together with two related compounds (4 and 5) were isolated from the extract of Chaetomium globosum HDN151398, a fungus isolated from a deep-sea sediment sample collected in South China Sea. Their structures were elucidated on the basis of extensive 1D and 2D NMR as well as HRESIMS spectroscopic data and chemical analysis. N-glutarylchaetoviridins A-C (1-3) represent the first class of chaetoviridins characterized by embedded glutamate residues. Amino acids incubation experiments produced five azaphilone laden different amino acids residues (6-10) which indicated that this method can enhanced the structural diversity of this strain by culturing with amino acids. Cytotoxicity of the isolated compounds were evaluated against a panel of human cancer cell lines.


Assuntos
Alcaloides/farmacologia , Antineoplásicos/farmacologia , Benzopiranos/farmacologia , Chaetomium/química , Sedimentos Geológicos/microbiologia , Pigmentos Biológicos/farmacologia , Alcaloides/química , Alcaloides/isolamento & purificação , Antineoplásicos/química , Antineoplásicos/isolamento & purificação , Organismos Aquáticos/química , Benzopiranos/química , Benzopiranos/isolamento & purificação , Linhagem Celular Tumoral , Ensaios de Seleção de Medicamentos Antitumorais , Glutamina/química , Humanos , Concentração Inibidora 50 , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Pigmentos Biológicos/química , Pigmentos Biológicos/isolamento & purificação
9.
Mar Drugs ; 17(5)2019 Apr 30.
Artigo em Inglês | MEDLINE | ID: mdl-31052279

RESUMO

Four new azaphilones, sclerotiorins A-D (1-4), as well as the dimeric sclerotiorin E (5) of which we first determined its absolute configuration, and 12 known analogues (5-16) were isolated from the fermentation broth of Penicillium sclerotiorum OUCMDZ-3839 associated with a marine sponge Paratetilla sp.. The new structures, including absolute configurations, were elucidated by spectroscopic analyses, optical rotation, ECD spectra, X-ray single-crystal diffraction, and chemical transformations. Compounds 11 and 14 displayed significant inhibitory activity against α-glycosidase, with IC50 values of 17.3 and 166.1 µM, respectively. In addition, compounds 5, 7, 10, 12-14, and 16 showed moderate bioactivity against H1N1 virus.


Assuntos
Benzopiranos/farmacologia , Penicillium/química , Pigmentos Biológicos/farmacologia , Animais , Benzopiranos/química , Benzopiranos/isolamento & purificação , Fungos , Glicosídeo Hidrolases/efeitos dos fármacos , Vírus da Influenza A Subtipo H1N1/efeitos dos fármacos , Estrutura Molecular , Pigmentos Biológicos/química , Pigmentos Biológicos/isolamento & purificação , Poríferos
10.
Mar Drugs ; 17(6)2019 May 28.
Artigo em Inglês | MEDLINE | ID: mdl-31142027

RESUMO

Recent studies have shown that marine algae represent a great source of natural compounds with several properties. The lipidic extract of the seaweed Chaetomorpha linum (Chlorophyta, Cladophorales), one of the dominant species in the Mar Piccolo of Taranto (Mediterranean, Ionian Sea), revealed an antibacterial activity against Vibrio ordalii and Vibrio vulnificus, common pathogens in aquaculture, suggesting its potential employment to control fish and shellfish diseases due to vibriosis and to reduce the public health hazards related to antibiotic use in aquaculture. This extract showed also an antioxidant activity, corresponding to 170.960 ± 16. mmol Trolox equivalent/g (oxygen radical absorbance capacity assay-ORAC) and to 30.554 ± 2.30 mmol Trolox equivalent/g (Trolox equivalent antioxidant capacity assay-TEAC). The chemical characterization of the extract, performed by 1D and 2D NMR spectroscopy, highlighted the presence of free, saturated (SAFAs), unsaturated (UFAs) and polyunsaturated (PUFAs) fatty acids. The high content of ω-6 and ω-3 PUFAs confirmed also by gas chromatography indicates the potentiality of this algal species in the production of fortified food. The antibacterial activity seems related to the presence of linolenic acid present at high density, while the antioxidant activity could be likely ascribable to molecules such as carotenoids and chlorophylls (characterized also by thin-layer chromatography), known for this property. The presence of polyhydroxybutyrate, a biopolymer with potentiality in the field of biodegradable bioplastics was also detected. The exploitation of C. linum for a future biotechnological application is also encouraged by the results from a first attempt of cultivating this species in an integrated multi-trophic aquaculture (IMTA) system.


Assuntos
Clorófitas/química , Lipídeos/química , Lipídeos/farmacologia , Compostos Fitoquímicos/química , Antibacterianos/química , Antibacterianos/farmacologia , Antioxidantes/química , Antioxidantes/farmacologia , Bactérias/efeitos dos fármacos , Clorófitas/crescimento & desenvolvimento , Cromatografia em Camada Delgada , Ácidos Graxos/análise , Espectroscopia de Ressonância Magnética , Mar Mediterrâneo , Compostos Fitoquímicos/farmacologia , Pigmentos Biológicos/química
11.
Biotechnol Lett ; 41(6-7): 813-822, 2019 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-31069568

RESUMO

OBJECTIVE: To explore the secondary metabolite biosynthetic potential of Rubrivivax benzoatilyticus JA2 using a new metabolite mining strategy. RESULTS: Combination of precursor-feeding and altered growth conditions were used to mine new biomolecules. Strain JA2 utilised L-phenylalanine as sole source of nitrogen and showed pigments production only under phenylalanine-amended aerobic cultures. Stable isotope based precursor feeding studies indicated the blue pigment consists of 4-phenyl rings derived from L-phenylalanine. The purified blue pigment displayed characteristic visible-absorption and pH-dependent color variations. Precursor-feeding under altered growth conditions activated the plausible novel aromatic pigment production in strain JA2. CONCLUSION: Our approach unraveled the previously unknown pigment synthesis in strain JA2 and demonstrated the potential of mining strategy in discovering the hidden secondary metabolite repertoire in microorganisms.


Assuntos
Burkholderiales/crescimento & desenvolvimento , Burkholderiales/metabolismo , Pigmentos Biológicos/biossíntese , Aerobiose , Técnicas Bacteriológicas , Nitrogênio/metabolismo , Fenilalanina/metabolismo , Pigmentos Biológicos/química , Pigmentos Biológicos/isolamento & purificação
12.
J Microbiol Biotechnol ; 29(6): 897-904, 2019 Jun 28.
Artigo em Inglês | MEDLINE | ID: mdl-31091861

RESUMO

Monascus purpureus recombinant mppC and mpp7 knockout strains were subjected to extractive fermentation in the context of azaphilone pigment production. Inclusion of Diaion HP-20 resin resulted in the selective production of unreduced azaphilone congeners, in addition to the early intermediate FK17-P2a, from ∆mppC and ∆mpp7 strains that would otherwise mainly produce reduced congeners. Structural determination of two novel unreduced azaphilones from the ∆mpp7 strain was accomplished. The unreduced azaphilone compound was converted into the cognate reduced congener in recombinant M. purpureus strains, demonstrating its intermediate role in azaphilone biosynthesis. This study demonstrates the possibility that extractive fermentation with Diaion HP-20 resin can be used to obtain cryptic azaphilone metabolites.


Assuntos
Benzopiranos/metabolismo , Microbiologia Industrial/métodos , Monascus/genética , Monascus/metabolismo , Pigmentos Biológicos/metabolismo , Poliestirenos/metabolismo , Benzopiranos/química , Vias Biossintéticas , Fermentação , Proteínas Fúngicas/genética , Proteínas Fúngicas/metabolismo , Deleção de Genes , Oxirredução , Pigmentos Biológicos/química
13.
J Agric Food Chem ; 67(14): 4031-4042, 2019 Apr 10.
Artigo em Inglês | MEDLINE | ID: mdl-30892885

RESUMO

The increase of temperature can cause a decoupling of sugar and anthocyanin accumulation in grapes, leading to wines poor in color. Different enological techniques are nowadays under study to overcome this problem. Among them, the present study has evaluated the color and pigment composition modifications caused by the addition during Syrah winemaking of either Pedro Ximénez seeds (intended to increase chemical stability) or/and two different mannoproteins (color-protective and astringency-modulator) to increase colloidal stability. Color and pigment composition modifications were assessed from CIELAB color parameters and from HPLC-DAD-MS n results before and after cold-treatment (used to force colloidal instability). The addition of both seeds and mannoproteins increased color stability against cold and, additionally, against SO2-bleaching in the case of mannoproteins. However, the initial pigment composition and color of the samples were differently affected by these additions, being clearly affected (Δ E* ab > 3) in the cases of seeds and with the astringency-modulator mannoprotein and hardly modified with the other one.


Assuntos
Aditivos Alimentares/química , Manipulação de Alimentos/métodos , Glicoproteínas de Membrana/química , Pigmentos Biológicos/química , Sementes/química , Vitis/química , Vinho/análise , Cor , Fermentação , Aditivos Alimentares/metabolismo , Glicoproteínas de Membrana/metabolismo , Pigmentos Biológicos/metabolismo , Saccharomyces cerevisiae/metabolismo , Vitis/metabolismo , Vitis/microbiologia , Vinho/microbiologia
14.
Nat Commun ; 10(1): 1004, 2019 03 01.
Artigo em Inglês | MEDLINE | ID: mdl-30824708

RESUMO

Chromatophore organs in cephalopod skin are known to produce ultra-fast changes in appearance for camouflage and communication. Light-scattering pigment granules within chromatocytes have been presumed to be the sole source of coloration in these complex organs. We report the discovery of structural coloration emanating in precise register with expanded pigmented chromatocytes. Concurrently, using an annotated squid chromatophore proteome together with microscopy, we identify a likely biochemical component of this reflective coloration as reflectin proteins distributed in sheath cells that envelop each chromatocyte. Additionally, within the chromatocytes, where the pigment resides in nanostructured granules, we find the lens protein Ω- crystallin interfacing tightly with pigment molecules. These findings offer fresh perspectives on the intricate biophotonic interplay between pigmentary and structural coloration elements tightly co-located within the same dynamic flexible organ - a feature that may help inspire the development of new classes of engineered materials that change color and pattern.


Assuntos
Cefalópodes/química , Cefalópodes/ultraestrutura , Cromatóforos/química , Cromatóforos/ultraestrutura , Pigmentação da Pele , Animais , Cor , Grânulos Citoplasmáticos/ultraestrutura , Decapodiformes , Simulação de Acoplamento Molecular , Pigmentos Biológicos/química , Pigmentos Biológicos/isolamento & purificação , Proteoma , Pele , Transcriptoma
15.
Mar Biotechnol (NY) ; 21(3): 416-429, 2019 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-30874930

RESUMO

Considering the global trend in the search for alternative natural compounds with antioxidant and sun protection factor (SPF) boosting properties, bacterial carotenoids represent an opportunity for exploring pigments of natural origin which possess high antioxidant activity, lower toxicity, no residues, and no environmental risk and are readily decomposable. In this work, three pigmented bacteria from the Antarctic continent, named Arthrobacter agilis 50cyt, Zobellia laminarie 465, and Arthrobacter psychrochitiniphilus 366, were able to withstand UV-B and UV-C radiation. The pigments were extracted and tested for UV absorption, antioxidant capacity, photostability, and phototoxicity profile in murine fibroblasts (3T3 NRU PT-OECD TG 432) to evaluate their further potential use as UV filters. Furthermore, the pigments were identified by ultra-high-performance liquid chromatography-photodiode array detector-mass spectrometry (UPLC-PDA-MS/MS). The results showed that all pigments presented a very high antioxidant activity and good stability under exposure to UV light. However, except for a fraction of the A. agilis 50cyt pigment, they were shown to be phototoxic. A total of 18 different carotenoids were identified from 23 that were separated on a C18 column. The C50 carotenes bacterioruberin and decaprenoxanthin (including its variations) were confirmed for A. agilis 50cyt and A. psychrochitiniphilus 366, respectively. All-trans-bacterioruberin was identified as the pigment that did not express phototoxic activity in the 3T3 NRU PT assay (MPE < 0.1). Zeaxanthin, ß-cryptoxanthin, ß-carotene, and phytoene were detected in Z. laminarie 465. In conclusion, carotenoids identified in this work from Antarctic bacteria open perspectives for their further biotechnological application towards a more sustainable and environmentally friendly way of pigment exploitation.


Assuntos
Arthrobacter/química , Biotecnologia , Flavobacteriaceae/química , Pigmentos Biológicos/química , Regiões Antárticas , Carotenoides/química , Carotenoides/isolamento & purificação , Microbiologia Industrial , Pigmentos Biológicos/isolamento & purificação
16.
Molecules ; 24(3)2019 Feb 03.
Artigo em Inglês | MEDLINE | ID: mdl-30717480

RESUMO

In this study, hybrid pigments based on carminic acid (CA) were synthesized and applied in polymer materials. Modification of aluminum-magnesium hydroxycarbonate (LH) with CA transformed the soluble chromophore into an organic-inorganic hybrid colorant. Secondary ion mass spectroscopy (TOF-SIMS), X-ray photoelectron spectroscopy (XPS), X-ray diffraction (XRD), thermogravimetric analysis (TGA), scanning electron microscopy (SEM), and UV-Vis spectroscopy were used to study the structure, composition, and morphology of the insoluble LH/CA colorant. Successful modification of the LH was confirmed by the presence of interactions between the LH matrix and molecules of CA. XPS analysis corroborated the presence of CA complexes with Mg2+ ions in the LH host. The batochromic shift in UV-Vis spectra of the organic-inorganic hybrid colorant was attributed to metal-dye interactions in the organic-inorganic hybrid colorants. Strong metal-dye interactions may also be responsible for the improved solvent resistance and chromostability of the modified LH. In comparison to uncolored ethylene-norbornene copolymer (EN), a modified EN sample containing LH/CA pigment showed lower heat release rate (HRR) and reduced total heat release (THR), providing the material with enhanced flame retardancy.


Assuntos
Hidróxido de Alumínio/química , Carbonatos/química , Carmim/química , Hidróxido de Magnésio/química , Polímeros/química , Estrutura Molecular , Espectroscopia Fotoeletrônica , Pigmentos Biológicos/química , Termogravimetria , Difração de Raios X
17.
Food Funct ; 10(2): 1073-1084, 2019 Feb 20.
Artigo em Inglês | MEDLINE | ID: mdl-30720827

RESUMO

This study aimed to compare the hypolipidaemic activities of different Monascus pigments (yellow, red and orange pigments) and elucidate their possible regulatory mechanisms on lipid and cholesterol metabolism in rats fed on a high-fat diet (HFD). Results showed that oral administrations of Monascus yellow, red and orange pigments can markedly alleviate the disturbance of lipid metabolism through ameliorating the serum lipid levels and suppressing hepatic lipid accumulation and steatosis. Meanwhile, the excretion of fecal cholesterol, triacylglycerols and bile acids was also promoted by the oral administrations of different Monascus pigments (MPs). Furthermore, Monascus pigment (MP) supplementation produced significant structural changes in the intestinal microbiota of HFD-fed rats, and modulated the relative abundance of functionally related microbial phylotypes compared with the HFD group in particular. Key phylotypes in response to the HFD and Monascus pigment (MP) intervention were found to strongly correlate with the lipid metabolism disorder associated parameters using Spearman's correlation coefficient. Some beneficial gut microbiota (such as Oscillibacter sp., Ruminococcus albus, Clostridium sp., etc.) were found to be negatively correlated with the serum and hepatic lipid indicator. Moreover, Monascus pigment (MP) treatments regulated the mRNA expression levels of the genes responsible for lipid and cholesterol metabolism. In general, different Monascus pigments (MPs) regulate the homeostasis of lipid and cholesterol metabolism through different regulatory pathways. These findings illustrated that not only Monascus yellow pigments, but also Monascus red and orange pigments have the potential to ameliorate lipid metabolic disorders, and therefore could be used as potential functional food ingredients for the prevention or treatment of hyperlipidemia and gut microbiota dysbiosis.


Assuntos
Produtos Biológicos , Disbiose/tratamento farmacológico , Microbioma Gastrointestinal/efeitos dos fármacos , Metabolismo dos Lipídeos/efeitos dos fármacos , Monascus/química , Pigmentos Biológicos/farmacologia , Animais , Dieta Hiperlipídica , Fezes/química , Hepatopatia Gordurosa não Alcoólica/induzido quimicamente , Hepatopatia Gordurosa não Alcoólica/prevenção & controle , Pigmentos Biológicos/química , Ratos , Ratos Wistar
18.
J Agric Food Chem ; 67(8): 2175-2182, 2019 Feb 27.
Artigo em Inglês | MEDLINE | ID: mdl-30702881

RESUMO

Nine new azaphilone alkaloids, penazaphilones A-I (1-9), were isolated from the solid fermented rice culture of Penicillium sclerotiorum cib-411. The structures of compounds 1-9 were elucidated based on HRESIMS, NMR, and CD spectroscopic data. The structures of 5 and 8 were confirmed by X-ray crystallographic analyses. Biological evaluation showed that compounds 1, 5, 6, and 8 inhibited the production of nitric oxide (NO) on RAW 264.7 cells stimulated by lipopolysaccharide with IC50 values of 15.29, 9.34, 9.50, and 7.05 µM, respectively. Meanwhile, they did not exhibit obvious cytotoxicity at a concentration of 50.0 µM.


Assuntos
Alcaloides/farmacologia , Anti-Inflamatórios/farmacologia , Benzopiranos/farmacologia , Penicillium/química , Pigmentos Biológicos/farmacologia , Alcaloides/química , Animais , Anti-Inflamatórios/química , Benzopiranos/química , Macrófagos/efeitos dos fármacos , Macrófagos/imunologia , Camundongos , Estrutura Molecular , Pigmentos Biológicos/química , Células RAW 264.7
19.
J Sci Food Agric ; 99(8): 3860-3870, 2019 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-30680730

RESUMO

BACKGROUND: In this study, we investigated whether electron beam (e-beam) irradiation can inactivate microbial populations, including aerobic bacteria plate count, fungi, and coliforms, in two types of lavers (dried and roasted). The impact of e-beam doses of 4 and 7 kGy on microbial populations, color values, total soluble pigments, chlorophylls, and carotenoid content immediately and after storage at 4, 15, 25, and 35 °C for 4, 8, and 12 weeks was also evaluated. RESULTS: The initial microbial load of approximately 106 and 105 CFU g-1 in both dried and roasted lavers was reduced to 104 and 101 CFU g-1 , respectively, after irradiation at 7 kGy. No further proliferation was observed in irradiated dried lavers during 4 weeks of storage at 4 and 15 °C. When stored at low temperature, the shelf-life was extended for up to 12 weeks in 7 kGy irradiated dried and roasted lavers. High amounts of soluble pigments and carotenoids were observed during storage in the 7 kGy irradiated dried laver samples at the end of 12 weeks irrespective of temperature. Although the chlorophyll content decreased under the storage conditions, it was comparatively stable in the 7 kGy-irradiated dried laver. Maximum degradation of color was observed in laver samples subjected to the roasting process. CONCLUSION: Overall, this study indicated that e-beam irradiation of laver at 7 kGy maintains microbial safety as well as quality attributes during storage for up to 12 weeks. Further, dried laver had more essential compounds than roasted laver. © 2019 Society of Chemical Industry.


Assuntos
Carotenoides/química , Clorofila/química , Irradiação de Alimentos/métodos , Pigmentos Biológicos/química , Extratos Vegetais/química , Porphyra/química , Bactérias/crescimento & desenvolvimento , Bactérias/isolamento & purificação , Bactérias/efeitos da radiação , Temperatura Baixa , Armazenamento de Alimentos , Humanos , Folhas de Planta/química , Folhas de Planta/microbiologia , Porphyra/microbiologia , Controle de Qualidade , Paladar
20.
Phytochemistry ; 159: 108-118, 2019 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-30605852

RESUMO

Five previously undescribed acylated pelargonidin 3-sophoroside-5-glucosides (pigments 2-6) were isolated from the red-purple flowers of Iberis umbellata L. 'Candycane Rose' and 'Candycane Red', in addition to a known one (pigment 1). The structures of five undescribed acylated anthocyanins were determined by chemical and spectroscopic methods to be pelargonidin 3-O-[2-O-(2-O-("acyl-A")-ß-glucopyranosyl)-6-O-("acyl-B")-ß-glucopyranoside]-5-O-[6-O-(malonyl)-ß-glucopyranoside], in which the "acyl-A" group was either trans-sinapic (2), trans-ferulic (3), trans-sinapic (4), trans-ferulic (5), or trans-ferulic acid (6), and "acyl-B" was either glucosyl-trans-p-coumaric acid (2), glucosyl-trans-p-coumaric acid (3), trans-feruloyl-glucosyl-trans-p-coumaric acid (4), trans-feruloyl-glucosyl-trans-p-coumaric acid (5), or glucosyl-trans-feruloyl-glucosyl-trans-p-coumaric acid (6). Moreover, three previously undescribed acylated pelargonidin 3-sambubioside-5-glucosides (pigments 7, 8, and 10) and one undescribed acylated pelargonidin 3-(3X-glucosylsambubioside)-5-glucoside (pigment 9) were isolated from the red flowers of Erysimum × cheiri (L.) Crantz 'Aurora' as major anthocyanins. The structures of the three undescribed acylated pelargonidin 3-sambubioside-5-glucosides were determined to be pelargonidin 3-O-[2-O-(2-O-("acyl-C")-ß-xylopyranosyl)-6-O-("acyl-D")-ß-glucopyranoside]-5-O-(ß-glucopyranoside), in which the "acyl-C" group was either non (7), non (8), or trans-p-coumaric acid (10) and "acyl-D" was either trans-p-coumaric (7), trans-ferulic (8), or trans-p-coumaric acid (10). Moreover, a previously undescribed acylated pelargonidin 3-(3X-glucosylsambubioside)-5-glucoside was identified to be pelargonidin 3-O-[2-O-(2-O-(trans-p-coumaroyl)-3-O-(ß-glucopyranosyl)-ß-xylopyranosyl)-6-O-(trans-p-coumaroyl)-ß-glucopyranoside]-5-O-(ß-glucopyranoside) (9). In addition, the distribution of anthocyanidins structural elements in 24 Brassicaceous species is compared.


Assuntos
Antocianinas/metabolismo , Brassicaceae/metabolismo , Flores/metabolismo , Glicosídeos/metabolismo , Acilação , Antocianinas/química , Cromatografia Líquida de Alta Pressão , Cromatografia em Camada Delgada , Glicosídeos/química , Espectroscopia de Ressonância Magnética/métodos , Estrutura Molecular , Pigmentos Biológicos/química , Pigmentos Biológicos/metabolismo , Espectrometria de Massas de Bombardeamento Rápido de Átomos , Espectrofotometria Ultravioleta
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