Structural and chromatic characterization of a new Malvidin 3-glucoside–vanillyl–catechin pigment

A new pigment, resulting from the reaction between malvidin 3-glucoside and catechin in the presence of vanillin, was detected in a model solution. This newly formed anthocyanin-aryl-flavanol adduct was structurally characterized by 1D and 2D NMR and mass spectrometry, and its chromatic characteristics were studied by UV–Vis techniques. The new pigment was shown to have a wavelength of maximum absorption in the visible region (λ_max) of 549 nm, conferring on it a purple colour, and a molar extinction coefficient value (ε) of 12,247 l · mol⁻¹ · cm⁻¹.     

Pigments composition in monovarietal virgin olive oils from various sicilian olive varieties

This paper presents the first investigation of the chlorophyll and carotenoid pigments composition in sicilian monovarietal virgin olive oils from the three (Cerasuola, Nocellara, Biancolilla) main olive varieties cultivated in Sicily (Italy). In all, 19 compounds were identified and quantified in 24 olive oil samples. The application of reversed-phase liquid chromatography with photodiode array detection using a C-30 column in the simultaneous qualitative–quantitative analysis of virgin olive oils pigments, has been shown. The qualitative pigment pattern was similar among the varieties investigated, whereas quantitative differences were found among the different cultivars, which can all be considered as having an high pigment content. Pheophytin a, was the major component (19.36–25.04 ppm), followed by β-carotene (8.06–16.27 ppm). Pheophytin a′ (2.92–4.17 ppm), lutein (2.28–4.49 ppm) and neoxanthin (1.54–2.11 ppm) were also well represented. The presence of carotenoid esters was also detected. The neoxanthin and β-carotene contents were higher compared to reports present in the literature for other olive oil varieties. This may be due to genetic factors and/or geographical differences. The ratio between the two isochromic pigment fractions, namely the chlorophyll and the carotenoid fractions, was around one in all varieties, showing that they were in balance. The lutein/β-carotene ratio was less than one in all cases. These parameters, along with other analytical parameters, could be used as indicators of typicality in olive oils. The presence of a specific pigment profile in olive oils could in fact be used to guarantee the genuineness of the product, since the quality control of food requires a precise knowledge of the pigments composition of the original products.     

Effect of the monascus pigment threonine derivative on regulation of the cholesterol level in mice

Different amino acid derivatives were synthesized during cultivation of a Monascus species. Derivatives exhibiting an inhibitory activity against HMG-CoA reductase were screened by in vitro tests. The threonine derivative had a high inhibitory activity of 38% while four other derivatives showed a greater than 23% activity. The orange monascus pigment showed a high activity of 36%. In vivo tests using female C57BL/6 mice were performed with the threonine derivative and orange pigment. Changes in the cholesterol and lipid levels in mice due to addition of the pigments were investigated. The total cholesterol (TC) level of mouse serum was reduced by 8–9% with the threonine derivative and by 16% with orange pigment. Supplementation with the threonine derivative and orange pigment decreased the LDL cholesterol level by 18–26% and increased the HDL cholesterol level by 1–9%. The atherogenic index (AI) value was reduced by 23–27% with pigment supplementation. The anti-atherosclerosis effect of monascus pigments can be induced by control of the lipid content in the serum rather than in the liver of mice.     

Partition of selected food preservatives in fish oil–water systems

The partition coefficients (K_ow) of benzoic acid and sorbic acid in systems of fish oil (sand eel)–water, fish oil–buffer solution, rape oil–water and olive oil–water were experimentally determined in a temperature range from 5 to 43 °C and pH from 4.5 to 6.5 °C. The dimerization of benzoic acid in fish oil–water system was observed at 25 °C. Two modifications have been made to the Nordic Food Analysis Standard for the determination of sorbic acid by HPLC. The experimental results show that the K_ow of benzoic acid and sorbic acid in fish oil–buffer system is ca. 100 times lower than that in fish oil–water system. The K_ow values of benzoic acid and sorbic acid in fish oil and water system decrease with increasing system pH values. The partition coefficients of plant origin and fish origin oils are in the same order of magnitude even though their molecular structures are very different.     

A kind of potential food additive produced by Streptomyces coelicolor: Characteristics of blue pigment and identification of a novel compound, λ-actinorhodin

The blue pigment produced by Streptomyces coelicolor 100 with a yield as high as 3 g/l is a mixture of 10 components. The structure of one of the components was identified and it is a new actinorhodin analogue, named as λ-actinorhodin. The natural pigment can be dissolved in alkaline water solution and a number of organic solvents in common use. The color of a water solution of the pigment changes with pH value. The pigment is stable to light, heat and food additives in common use, and resistant to oxidants and reducers under acidic conditions and to reducers under alkaline conditions. Most inspected metal ions hardly affected pigment stability except for Fe²⁺ at high concentration and Pb²⁺. The pigment is nontoxic with LD₅₀ > 15,000 mg/kg in an acute toxicity trial. The good characteristics of the pigment make it potential useful in the food processing industry as an additive.     

Characterization of a new yellow pigment from model reaction system related to garlic greening

Three yellow pigments have been identified from three reaction systems containing pyruvic acid and 2-(1H-pyrrolyl) acetic acid, 1-(2′-methyl-1′-carboxy-propyl) pyrrole, and 1-(2′-methyl-1′-carboxy-butyl) pyrrole (a kind of precursor of garlic green pigment) related to garlic greening in previous paper, respectively. In the present study, another kind of yellow pigment from the same system containing pyruvic acid and 2-(1H-pyrrolyl) acetic acid was identified by liquid chromatography–electrospray ionization mass spectrometry (LC-ESI MS/MS) and high-resolution electrospray ionization mass spectrometry. This kind of pigment made predominant contribution to the production of yellow pigment in this model reaction pathway, which was involved in garlic discoloration. It was observed that there were two more methyl groups located on two conjugated double bonds that bridged two moles of 2-(1H-pyrrolyl) acetic acid compared to the structures of pigments, which was identified in our previous paper. Molecular weight of the pigment is 329.1495 [M+H]⁺, and its molecular formula is C₁₈H₂₀N₂O₄ which has a maximal absorbance at 436.9 nm, due to its conjugated structure.     

Effect of light on growth,intracellular and extracellular pigment production by five pigment-producing filamentous fungi in synthetic medium

The competence of the living creatures to sense and respond to light is well known. The effect of darkness and different color light quality on biomass, extracellular and intracellular pigment yield of five potent pigment producers Monascus purpureus, Isaria farinosa, Emericella nidulans, Fusarium verticillioides and Penicillium purpurogenum, with different color shades such as red, pink, reddish brown and yellow, were investigated. Incubation in total darkness increased the biomass, extracellular and intracellular pigment production in all the fungi. Extracellular red pigment produced by M. purpureus resulted maximum in darkness 36.75 ± 2.1 OD and minimum in white unscreened light 5.90 ± 1.1 OD. Similarly, intracellular red pigment produced by M. purpureus resulted maximum in darkness 18.27 ± 0.9 OD/g and minimum in yellow light 8.03 ± 0.6 OD/g of substrate. The maximum biomass production was also noticed in darkness 2.51 g/L and minimum in yellow light 0.5 g/L of dry weight. In contrast, growth of fungi in green and yellow wavelengths resulted in low biomass and pigment yield. It was found that darkness, (red 780–622 nm, blue 492–455 nm) and white light influenced pigment and biomass yield.     

Acidic degradation and enhanced antioxidant activities of exopolysaccharides from Cordyceps sinensis mycelial culture

An exopolysaccharide (EPS) fraction isolated from mycelial culture of a Cordyceps sinensis fungus, designated EPS-1 with an average molecular weight (MW) of 38 kDa, was hydrolysed in dilute sulphuric acid solution at pH 1 and 90 °C, yielding two major MW fractions, 3.0 kDa and 30 kDa, respectively. While the proportion of lower MW fraction increased with the hydrolysis period (18% in 0.5 h and 92% in 10 h), the polydispersity (M_w/M_n) of EPS decreased steadily (from 1.47 initially to 1.10 in 10 h). The IR spectra of hydrolysed EPS fractions showed changes only in the C–O–C and C–O–H band peaks from that of EPS-1. These results suggest that the hydrolysis of EPS in the acidic solution caused the EPS degradation mainly by cleaving the glycosidic linkage but no change in the primary molecular structure. The hydrolysed EPS fractions had much higher (30–80%) antioxidant and radical-scavenging activities.     

Solutions properties and solute–solvent interactions in ternary sugar–salt–water solutions

Viscometric constants were used to provide information on solute–solvent interactions in ternary water–sugar–salt solutions. Comparison was made between pure water and aqueous salt solution as solvents affecting the behaviour of small carbohydrates. The determination of intrinsic viscosity was made more accurate by applying triple extrapolation of the three equations (Huggins, Kramer and Meffroy-Biget). Results obtained with this triple extrapolation method were compared to that obtained with the Jones–Dole equation usually used. The B coefficient of the Jones–Dole equation was interpreted in terms of its components (B_size) and (B_structure), respectively assigned to the hydrodynamic volume and the contribution to solvent structural change. The determination of the apparent molar volumes in pure water enabled calculation of the hydration numbers. The determined apparent molar volumes of the studied sugars in aqueous salt solutions suggested a dehydration of the sugars explained by sugar–salt interactions. The most important perturbations observed in LiCl solutions compared to those in NaCl solutions were explained by LiCl being surrounded with more water molecules.     

Isomaltulose production by free cells of Serratia plymuthica in a batch process

Free cells of Serratia plymuthica were used to convert sucrose into isomaltulose and trehalulose reducing sugars. The effects of substrate concentration and temperature were observed in a batch process with flasks shaken at 150 rpm. The experimental design and response surface methodology analysis indicated that the conversion parameters had significant influence (p < 0.05) on sucrose conversion, and that a valid model was obtained after an analysis of variance (F_model = 10.48 > F_charted = 5.79) to obtain a response surface and isocurve. Conversion was favoured when a 30% sucrose solution and temperature of 25 °C were used, which resulted in a high conversion into isomaltulose – over 70% – and 7–8% trehalulose. Small amounts of glucose (5–7%) and fructose (5–8%) were formed in the reaction medium.     

Isolation and characterization of pigment from Cinnamomum burmannii' peel

Cinnamomum burmannii is cultivated for use as a spice, and as an ornamental tree. With the aim to develop a natural colorant for use in cosmetics and food additives from a new source, in the present study, pigment derived from C. burmannii' peel (CBP) was isolated by alkaline extraction, acid hydrolysis, repeated precipitation and purification by Sephadex G-75 with a total yield of 0.06 g/100 g (wet weight basis). The color values of the pigment was E_1 cm^1% 278 nm = 65.21. Physical and chemical properties revealed that CBP presses similar properties as most natural pigment. It was scarcely soluble in both water and all common organic solvents, and was soluble only in alkaline aqueous and DMSO. It was stable under ultraviolet light or room-light, stable in the range of 25-100 °C, relatively stable in alkaline aqueous and reducer, but was bleached by strong oxidants (KMnO₄, H₂O₂ and NaOCl). Sodium benzoic acid, tartaric acid, table salt and cane sugar affected it slightly. Spectroscopic analysis of CBP in relation with its structure was also discussed. This is the first report on the characterization of pigment obtained from C. burmannii 'peel.     

Effect of various salts and pH condition on rheological properties of Salvia macrosiphon hydrocolloid solutions

The extraction of Salvia macrosiphon seed hydrocolloid was performed successfully and the optimum hydration time and temperature were found to be 30 min and 25 °C for 12% extraction yield. The effect of solution pH (3–9) and addition of NaCl (0.5–3%), CaCl₂ (0.5–3%) and Na₂HPO₄ (0.2–0.6%) on rheological properties of the hydrocolloid solutions were investigated. Rheologcal data were fitted with the Power law model with regression coefficient of greater than 0.95. Strong shear thinning behavior with the n value of less than 0.53 was recorded. All variables had significant impacts on rheological parameters. The minimum and maximum consistencies were found at pH 3 and the 9, respectively. This was explained with the presence of carboxylic groups on the biopolymer backbone as indicated by FTIR. NaCl, CaCl₂ and Na₂HPO₄ had significant effects on rheological properties. Moreover, at similar salt concentration of 0.5%, Na₂HPO₄ had the greatest and NaCl had the lowest effect.     

Studies on the structure and oxidation properties of extracted cooked cured meat pigment by four spectra

The structure and oxidation properties of cooked cured meat pigment (CCMP) were investigated by comparing the change in spectra of CCMP before and after oxidisation. CCMP was extracted using petroleum ether/acetone/ethyl acetate step by step from precooked cured beef. The extracted sample was oxidised by being exposed to air with normal lighting or adding 1.5 ppm H₂O₂, respectively. The structure of CCMP was identified as a pentacoordinate mononitrosylheme complex by electron paramagnetic resonance (EPR), HPLC/ESI-HR-MS, Raman and FT–IR spectra. The changed EPR spectra of CCMP in acetone oxidised under different conditions suggested a new proposal that the NO⁻ group might not detach itself from iron porphyrin during oxidation in air with normal lighting, but changed in conjugated structure, and the structure tended to axial symmetry by analysis of the changes in g factor. This hypothesis was further supported by the results of the HPLC/ESI-HR-MS and Raman spectrum.     

Coupled model of extended Nernst–Planck equation and film theory in nanofiltration for xylo-oligosaccharide syrup

This work presents an observed retention (R_obs) model for xylo-oligosaccharides (XOs) syrup in nanofiltration (NF) process. A commercial-purchased HDS-12-2540 NF membrane was operated in batch recycling model. The volume flux (J_v), trans-membrane pressure (ΔP), solute concentrations in feed solution (C_b) and permeate solution (C_p) were collected and the experimental R_obs was obtained. On the basis of the extended Nernst–Planck equation and film theory, a theoretical R_obs model was established. The model parameters including solute permeability (P_s) and reflection coefficient (σ) for arabinose, xylose and xylobiose were estimated by curving fitting using genetic algorithm (GA) method. It was found that the reflection coefficient (σ) for arabinose (0.895) was higher than that for xylose (0.776), which indicated that the membrane retention to arabinose was stronger. Membrane structural parameters, such as ratio of solute radius to pore radius (λ) and ratio of effective membrane porosity to membrane thickness (A_k/Δx), were also estimated using steric-hindrance pore (SHP) model.     

Pigments profile in monovarietal virgin olive oils from various Italian olive varieties

This paper presents the investigation of the chlorophyll and carotenoid pigments composition in monovarietal virgin olive oils produced from the five main olive varieties (Minuta, Ottobratica, Calabrese, Ogliarola, Baddarica) cultivated in Sicily (southern Italy), from four main olive varieties (DolceAgogia, Moraiolo, Leccino, Frantoio) cultivated in Umbria (central Italy), and from three main olive varieties (Leccino, Oliva Nera di Collecorto, Noccioluta) cultivated in Molise (central Italy). Reversed-phase high performance liquid chromatography using a C-30 column with photodiode array detection was used for pigments analyses. In all, 19 compounds were identified and quantified in 60 olive oils samples. The qualitative pigments pattern was similar among the varieties investigated, whereas quantitative differences were found among the different cultivars; among the varieties investigated in this work, the oils from Umbria showed the highest pigment content (34.19 ppm in average), followed by the oils from Molise (18.61 ppm in average) and the oils from Sicily which showed the lowest pigment contents (13.38 ppm in average). In general, pheophytin a was the major component (range 0.49–19.42 ppm), followed by β-carotene (range 1.27–9.30 ppm) and lutein (range 0.44–5.12 ppm). Those differences may be due to genetic factors and/or geographical differences. Moreover, auroxanthin was detected for the first time in olive oils and was detected only in olive oils from Umbria and Molise regions. The ratio between the two isochromic pigment fractions, namely the ratio between the chlorophyll and carotenoid fractions showed an average value close to unity. The lutein/β-carotene ratio was less than one in the majority of the cases. These parameters, along with other analytical parameters, could be used as indicators of typicality in olive oils. The presence of a specific pigment profile in olive oils could infact be used to guarantee the genuineness of the product, since the quality control of food requires a precise knowledge of the pigments composition of the original products.     

Optimisation of the solvent extraction of bioactive compounds from Parkia speciosa pod using response surface methodology

Central composite design was employed to optimise the buffer-to-solids ratio (X₁: 20–50 ml/g), incubation temperature (X₂: 35–55 °C) and time (X₃: 100–200 min), obtaining extracts from Parkia speciosa pod with high total phenolic and flavonoid contents and high antioxidant activities. Analysis of variance showed that the contribution of a quadratic model was significant for the responses. An optimisation study using response surface methodology was performed and 3D response surfaces were plotted from the mathematical models. The optimal conditions based on combination responses were: X₁ = 20 ml/g, X₂ = 35–36 °C and X₃ = 100–102 min. These optimum conditions yielded total phenolic contents of 664–668 mg gallic acid equivalents/100 g, total flavonoid contents of 47.4–49.6 mg pyrocatechol equivalents/100 g, %DPPH_sc of 81.2–82.1%, %ABTS_sc of 78.2–79.8% and FRAP values of 3.2–3.3 mM. Close agreement between experimental and predicted values was found. This methodology could be applied in the extraction of bioactive compounds in the natural product industry.     

Structural identification of the main ellagitannins of a boysenberry (Rubus loganbaccus × baileyanus Britt.) extract by LC–ESI-MS/MS,MALDI-TOF-MS and NMR spectroscopy

Four ellagitannins from boysenberry, a cross between Rubus loganbaccus and Rubus baileyanus Britt., were isolated by preparative HPLC and the exact structures determined by a combination of LC–ESI-MS/MS, MALDI-TOF-MS and NMR spectroscopy. The two most abundant ellagitannins were identified as sanguiin H-6, which is known to be abundant in Rubus species, and the other was identified as an isomer of sanguiin H-10, which has not previously been reported in Rubus. The two less abundant ellagitannins were identified as sanguiin H-2 and [galloyl–bis-HHDP–glucose]₂-gallate. Sanguiin H-2 has been previously reported in Rubus, whereas both sanguiin H-2 and [galloyl–bis-HHDP–glucose]₂-gallate have been previously reported as hot-water degradation products of lambertianin C. Even though lambertianin C is reported to be a major ellagitannin in other Rubus species, it was not found in any of the fractions, suggesting that both sanguiin H-2 and [galloyl–bis-HHDP–glucose]₂-gallate are present naturally in boysenberry.     

Use of the jabuticaba (Myrciaria cauliflora) depulping residue to produce a natural pigment powder with functional properties

The aim of this study was to produce a natural pigment powder with functional properties. To optimise the spray-drying process, a central composite design with 17 treatments was used, in which the independent variables were the inlet drying air temperature (138–202 °C), the feed flow rate (20–67 mL/min), and the concentration of the carrier (maltodextrin, 100–300 g/kg of extract). The dependent variables were the moisture content, hygroscopicity, and anthocyanin retention. The samples were analysed by: anthocyanin and phenolic content; antioxidant properties based on the ORAC and DPPH assays; antimicrobial activity against Staphylococcus aureus, Listeria monocytogenes, Salmonella enteritidis, and Escherichia coli; and inhibitory activity against arginase, an enzyme produced by Leishmania amazonensis. The experimental design was not significant or predictive in the ranges studied. The selected samples contained high concentrations of anthocyanins and phenolics, and high antioxidant capacities. In addition, they exhibited antimicrobial activity against three of the four microorganisms tested, and some of the samples also exhibited a bactericidal effect. Moreover, the powders exerted inhibitory activity (64–69%) against arginase. The results obtained in this study suggest that the jabuticaba depulping residue could be used to produce a natural pigment with functional properties.     

Analysis of ginsenosides in Panax ginseng in high pressure microwave-assisted extraction

High pressure microwave assisted extraction (HPMAE) was applied to extract the ginsenosides from Panax ginseng root. The influences of extraction solvent, extraction pressure and extraction time were individually investigated. HPMAE has been compared with other extraction methods, including Soxhlet extraction, ultrasound-assisted extraction and heat reflux extraction. The determination of ginsenosides was performed by HPLC–ESI-MS. The results indicated that the HPMAE not only took a shorter time but also afforded higher extraction yields of ginsenosides, especially ginsenoside Rb₁, Rc, Rb₂ and Rd. Furthermore, the neutral ginsenosides and malonyl ginsenosides in Panax ginseng root extracts by HPMAE were investigated. The malonyl ginsenoside m-Rb₁, m-Rc, m-Rb₂ and m-Rd degraded in HPMAE at 400 kPa (109–112 °C) in 70% (v/v) ethanol–water and at 600 kPa (112–115 °C) in methanol, and transformed into corresponding neutral ginsenoside Rb₁, Rc, Rb₂ and Rd. Using water as extraction solution, the neutral ginsenosides degraded under HPMAE at 400 kPa (135–140 °C), and transformed into less polarity rare ginsenosides.     

Optimizing a submerged Monascus cultivation for production of red pigment with bug damaged wheat using artificial neural networks

The combined effect of temperature, agitation speed, and light on red pigment production by Monascus purpureus (M. purpureus) Went DSM 1604 using bug damaged wheat was studied using an artificial neural network (ANN). Information retrieved from the ANN was used to determine the optimal operating conditions for pigment production by M. purpureus using bug damaged wheat meal. The developed ANN had R ² values for training, validation, and testing data sets of 0.993, 0.961, and 0.944, respectively. According to the model, the highest pigment production of 1.874 absorbance units at 510 nm (A_{510 nm}) would be achieved at 29°C and 150 rpm under light conditions. The mean value of the experimental results obtained under these optimum conditions was 1.787±0.072 A_{510 nm}, corresponding to a pigment yield of 35.740 A_{510 nm}/g. The study showed that bug damaged wheat can be used as a substrate for red pigment production by M. purpureus.