Carotenoid Bixin Research Articles

Acrylic yarns pre-treated with different mordants and their dyeing potential with annatto dye

The study aimed to identify the best conditions for dyeing acrylic fiber with natural annatto dye, considering the presence of metallic mordants such as alum and ferrous sulfate, and evaluating the influence of soy milk or the absence of a mordant. Exhaust dyeing tests were conducted with the extract at different pH ranges to understand the behavior of the carotenoids bixin and norbixin in annatto seeds. Color intensity was measured by spectrophotometry, while colorfastness tests were performed to assess color transfer. The alum mordant showed less colorfastness than dyeing without a mordant, suggesting interference in dye fixation despite high color intensity values. On the other hand, the ferrous sulfate mordant exhibited limited leveling but high colorfastness. The natural pH range of the extract with soy milk mordant demonstrated good colorfastness and moderate intensity, resulting in a light-yellow shade. These findings underscore the complexity of interactions between natural dyes, synthetic fibers, and different mordants, emphasizing the importance of considering various factors to optimize desired outcomes in acrylic fiber dyeing.

Stability, reusability, and equivalent circuit of TiO2/treated metakaolinite-based dye-sensitized solar cell: effect of illumination intensity on Voc and Isc values

In this research, treated metakaolinite (TMK) was introduced into the TiO2 photoelectrode to fabricated dye-sensitized solar cells (DSSCs). The photovoltaic cells have four main natural components, i.e., a photosensitizer (carotenoid bixin), photoelectrode (TiO2/kaolinite), electrolyte (glycerine carbonate derivative), and counter-electrode (carbon). Their stability, reusability, and equivalent circuit were studied. The presence of 5% of TMK in anatase TiO2 paste decreased the TiO2 band gap from 3.21 to 3.16 eV. The result showed that the presence of 5% of TMK in TiO2 paste was more favorable to obtain higher energy conversion efficiency. Under a light intensity of 200 W/m2, it produced an energy conversion yield of 0.086%. The combination of the electrolyte and the TMK demonstrated a synergistic effect to improve the electrical properties of the DSSC. The energy storage function worked well until the third day of analysis. The DSSC based on TiO2/TMK photoelectrode exhibited 16 times better stability than pure TiO2-based photoelectrode. The Faraday charge transfer processes showed that the TiO2/TMK photoelectrode is not in direct contact with the carbon counter-electrode.

Polymer-bixin nanofibers: A promising environmentally friendly material for the removal of dyes from water

A new environmentally safe technology for the removal of dyes was evaluated. A new polymeric nanofiber with a natural carotenoid bixin was used as an adsorbent. The material was manufactured by the electrospinning technique. The behavior of bixin nanofiber in the sorption on dye compounds was studied by investigating the deposition time, area, medium pH, ionic strength, adsorption kinetics and adsorption isotherms. Removal greater than 96% and 70% for BG and MB, respectively, was obtained under the following conditions: dye solutions of 20.0 mg kg−1, pH 6.00, and supporting area of 6.76 cm−2 of the adsorbent material (80 min of deposition of nanofibers on each face). The kinetics presented the best fit to the pseudo-second order model. Dye recoveries using real water samples from taps and lakes, as well as from aquaculture industry were over 58% and 78% for MB and BG, respectively. Thus, polymeric bixin nanofibers are promising for application as dye remover for water remediation.

Understanding Solvent/Bixin Interactions by Raman Spectroscopy

In this work, Raman spectroscopy and density functional theory (DFT) calculations have been used in order to understand the nature of the interaction between the carotenoid bixin and organic solvents with dielectric constant varying from ca. 2 (toluene) to ca. 47 (dimethyl sulfoxide). Raman shifts registered for the main carotenoid marker band, the C=C stretching mode (1525-1533 cm-1), were used as a probe to monitor spectral changes due to chemical interaction between bixin in the solid state with the analogous solvated species. Raman spectra of bixin in solution showed significant bathochromic shifts in the wavenumber position of ν(C=C) when compared with the solid state. Among the solutions, subtle differences were observed and the polarizability rather than dielectric constant of the solvents seems to be a more appropriate parameter to explain the differences in Raman shifts which could be correlated with the solvation degree of bixin. Correlation between DFT analysis and molecular dynamics simulations obtained for cis-bixin in DMSO and CHCl3 demonstrated that the interaction of the solute with the respective solvents occurs in specific portions of the molecule, however, this result was not confirmed by the experimental data since bixin is solvated by larger numbers of solvent molecules.

Bixin Triggers Apoptosis of Human Hep3B Hepatocellular Carcinoma Cells: An Insight to Molecular and IN SILICO Approach

Hepatocellular carcinoma (HCC) is the most common liver cancer and is known to be resistant to conventional chemotherapy. The use of herbal medicine and supplements has increased over recent decades following side effects and resistant to conventional chemotherapy. The seeds of Bixa orellana L. commonly known as annatto have recently gained scientific attention due to presence of a carotenoid bixin for its substantial anticancer properties. However, molecular mechanisms underlying bixin-induced apoptosis are still unclear. Treatment of bixin significantly decreased the number of Hep3B cells and morphological study revealed the change in cellular and nuclear morphology that trigger the events of apoptosis confirmed by annexin V/PI staining. Further DCFDA and rhodamine 123 spectrofluorimetry study showed elevation in reactive oxygen species (ROS) production and loss of mitochondrial membrane potential (MMP), respectively. ROS production caused DNA damage and apoptosis was marked by cell cycle arrest, up-regulation of Bax and FasL protein as well as cleavage of caspase-9, caspase-8 and caspase-3 protein. Docking study with pro-apoptotic molecule Bax and surface Fas ligand exhibited energetically favourable binding interaction. Collectively, these results suggest that bixin capable of modulating the extrinsic and intrinsic molecules of apoptosis indicating its potential for development of promising candidate for hepatocellular carcinoma.

The carotenoid Bixin found to exhibit the highest measured carotenoid oxidation potential to date consistent with its practical protective use in cosmetics, drugs and food

The electrochemical oxidation potentials of cis bixin correspond to the production of the carotenoid radical cation, Car+ and dication Car++. The oxidation is a two-electron process with oxidation potentials at ~0.94 and ~1.14 V vs SCE (reference to ferrocene at 0.528 V) in THF. These potentials are higher than that of symmetrical canthaxanthin at 0.775 V and 0.972 V and for β-carotene at 0.634 V and 0.605 V respectively. The second oxidation potential for canthaxanthin is higher by 0.20 V than the first. Similar difference is observed for bixin. In contrast, the second oxidation potential for β-carotene is lower by 30 mV than that of the first. Reduction potentials were found to occur at ~−0.69 and ~−1.22 V vs SCE. The lifetime of the radical cation of cis bixin, Car+, is short and decays rapidly at ambient temperature. The suggested scavenging ability of cis bixin towards reactive oxidative oxygen species is estimated to be 44. On the other hand, that of β-carotene, symmetrical canthaxanthin and the dicyano substituted carotenoid which exhibit oxidation potentials of 0.634 V, 0.775 V and 0.833 V vs SCE were measured to be 0.64, 1.96 and 23.60 respectively. The non-reversible electrochemical measurements suggest the tendency for bixin to react with trace amounts of reactive oxygen species (OH, O2−, OOH).

The carotenoid bixin: Optical studies of aggregation in polar/water solvents

In contrast to the H-aggregation that results in a 100 nm blue shift in the optical absorption maximum for all trans zeaxanthin and astaxanthin in methanol/water solutions, the carotenoid bixin in methanol water solution does not form an H-aggregate. Instead, it exhibits a 4 nm red shift in a 50% water-methanol solution, suggesting possible J-aggregation. The lack of H aggregation can be traced to the fact that the ground state geometry for bixin is cis and not trans, resulting in an unfavorable geometry for H-aggregate formation. However, bixin is one carotenoid that exhibits enhanced water solubility compared to other common carotenoids. The optical spectrum is reported for bixin in chloroform, dioxane, dimethylformamide, tetrahydrofuran, acetonitrile, and methanol. The optical absorption maximum is blue shifted relative to chloroform as the polarizability of the solvent decreases and the polarity increases. A blue shift (0–4 nm) is observed when water is added to these solvents, the largest shift found for 5% water in acetonitrile, the most polar of the solvents besides methanol.

ESTUDO DA EXTRAÇÃO DE CORANTE NATURAL QUE CONFERE PROTEÇÃO ULTRAVIOLETA EM FIBRAS NATURAIS

Neste trabalho estudaram-se parâmetros do processo de extração de bixina e norbixina a partir do urucum e a proteção ultravioleta conferida pelo corante à uma fibra natural. Avaliaram-se diferentes solventes de extração: acetona, acetato de etila, KOH em solução e etanol, bem como as misturas entre eles. Analisaram-se os efeitos de: temperatura (30 a 60oC); tamanho do sólido (semente intacta e moída); tempo de extração e razão mássica sólido/solvente nas proporções de 0,125, 0,25 e 0,42. Com os resultados obtidos verificou-se uma melhor extração utilizando-se a mistura etanol:acetona 50% (v/v), temperatura de 55ºC e tamanho da partícula de 100 MESH. A partir dos parâmetros adotados foi possível concluir que houve a saturação do solvente em 20 minutos de extração e com isso, concluiu-se que o sólido pode ser aproveitado para mais de um ciclo de extração. Verificou-se uma proteção ultravioleta conferida pelo corante aplicado no algodão alvejado de 89% da radiação ultravioleta absorvida.

The effect of the carotenoid bixin and annatto seeds on hematological markers and nephrotoxicity in rats subjected to chronic treatment with cisplatin

This study assessed the protective effect of the carotenoid bixin and annatto seeds against possible nephrotoxicity induced with a single peritoneal administration of pharmacological cisplatin in male Wistar rats. After 48h, the blood cell differential count showed a significant reduction in neutrophil counts in rats that received a diet rich in bixin when compared to the group that received only cisplatin. The use of cisplatin led to an increase in kidney weight. The carotenoid bixin attenuated renal injury, characterized by increased polymorphonuclear infiltration. No protective effect was observed with respect to Annatto. These results demonstrate the role of toxic cisplatin and suggest that bixin affords a protective effect against cisplatin-induced nephrotoxicity in adult Wistar rats.

The antiatherogenic effect of bixin in hypercholesterolemic rabbits is associated to the improvement of lipid profile and to its antioxidant and anti-inflammatory effects.

Hypercholesterolemia and oxidative stress have been implicated in the pathophysiology of atherosclerosis and coronary artery disease. We investigated whether the carotenoid bixin (BIX) may reduce oxidative damage, inflammatory response, and the atherosclerotic lesion induced by hypercholesterolemia in rabbits. Rabbits received regular chow (control) or a hypercholesterolemic diet (0.5% cholesterol) alone or supplemented with BIX (10, 30 or 100 mg/kg body weight, b.w.) or simvastatin (15 mg/kg b.w.) for 60 days. Treatment with BIX or simvastatin reduced the atherosclerotic lesions in cholesterol-fed rabbits (up to 55 and 96% reduction, respectively). This protective effect of BIX was accompanied by decrease in the levels of tumor necrosis factor alpha by 15%, interleukin 6 by 19%, lipid peroxidation by 60%, non-high-density lipoprotein cholesterol (non-HDL-C) by 37%, and triglycerides by 41%. BIX increased by 160% the HDL-C levels and decreased by 67% the atherogenic index of hypercholesterolemic rabbits. In atherosclerotic rabbits, the non-protein thiol groups content and the activity of the antioxidant enzymes superoxide dismutase, catalase, glutathione reductase, and thioredoxin reductase were increased in the aortic tissue, whereas paraoxonase activity was reduced in the serum. All these changes were completely prevented by BIX or simvastatin treatment. These results demonstrate that BIX reduces the extent of atherosclerotic lesions and this effect was associated with the decrease in oxidative stress, inflammatory response, and improvement of dyslipidemia, which were most effectively controlled after treatment with 10-30 mg BIX/kg b.w. BIX consumption may, therefore, be an adjuvant to prevent atherosclerosis reducing risk factors for coronary diseases.

Protective effect of bixin on carbon tetrachloride-induced hepatotoxicity in rats.

BackgroundThe liver is an important organ for its ability to transform xenobiotics, making the liver tissue a prime target for toxic substances. The carotenoid bixin present in annatto is an antioxidant that can protect cells and tissues against the deleterious effects of free radicals. In this study, we evaluated the protective effect of bixin on liver damage induced by carbon tetrachloride (CCl4) in rats.ResultsThe animals were divided into four groups with six rats in each group. CCl4 (0.125 mL kg-1 body wt.) was injected intraperitoneally, and bixin (5.0 mg kg-1 body wt.) was given by gavage 7 days before the CCl4 injection. Bixin prevented the liver damage caused by CCl4, as noted by the significant decrease in serum aminotransferases release. Bixin protected the liver against the oxidizing effects of CCl4 by preventing a decrease in glutathione reductase activity and the levels of reduced glutathione and NADPH. The peroxidation of membrane lipids and histopathological damage of the liver was significantly prevented by bixin treatment.ConclusionTherefore, we can conclude that the protective effect of bixin against hepatotoxicity induced by CCl4 is related to the antioxidant activity of the compound.

Antioxidant activity and physicochemical characterization of raw and encapsulated annatto

Bixa orellana species is originated in tropical America and is widely used in the industry of natural colorants. The annatto colorant has a reddish coloration due to the presence of the carotenoid bixin in its seed aril. The objective of the present work was evaluating the antioxidant potential and characterize the physicochemical properties of three annatto cultivars in fresh (seeds) and encapsulated powder. Therefore, moisture, ash, lipid, protein and carbohydrates were analyzed. To evaluate the antioxidant properties the ABTS (2,2’-azinobis (3-ethylbenzothiazoline-6-sulfonic acid) method was used. The annatto seeds and encapsulated products showed antioxidant potential for free radical ABTS, being superior to the synthetic antioxidant BHT which showed 63.62% of inhibition. These results suggest that the use of annatto colorant can provide a preventive action on diseases contributing in a beneficial way to human health.

Spectroscopic and photothermal characterization of annatto: Applications in functional foods

Dyes are among the most common additives used primarily to intensify, compensate or add color to manufactured products. The major color detected in annatto seeds comes from carotenoids bixin (C25H30O4) and norbixin (C24H28O4), depending on the extraction method. This article presents absorption and fluorescence spectroscopic characterizations of annatto extracted in aqueous solutions from seeds of the tropical shrub Bixa orellana L. Extractions from seeds were performed using aqueous solution (at 98 °C) with different potential of hydrogen values (pH 6.5–11.2), and the results were compared to those obtained with chemical extraction methods using other solvents. Thermo-optical parameters, such as refractive index temperature coefficient (dn/dT), thermal diffusivity (D), fraction thermal load (φ) and quantum yield (η) were determined for annatto solutions. Finally, the effectiveness of using of different concentrations of annatto dye in bread preparation is investigated as a functional food possibility.

Carotenoides bixina e norbixina extraídos do urucum (Bixa orellana L.) como antioxidantes em produtos cárneos

A oxidação lipídica é uma das principais alterações que acometem os derivados cárneos em razão da composição química rica em lipídios e íons ferro, utilização de processos térmicos e de moagem, além do frequente uso do cloreto de sódio, um reconhecido catalisador desta reação. Os antioxidantes são substâncias utilizadas para inibir ou retardar a rancidez oxidativa, porém, seu uso desperta a atenção de consumidores e agências reguladoras, quanto à segurança que acompanha o consumo de aditivos sintéticos. Este trabalho teve por objetivo avaliar o uso dos carotenoides bixina e norbixina como antioxidantes em produtos cárneos por meio da revisão de suas características químicas, métodos de obtenção, toxicidade e aplicações tecnológicas. Esses pigmentos são extraídos das sementes do urucum (Bixa orellana L.) por métodos que envolvem o uso de solventes orgânicos, extração supercrítica ou ainda a utilização da tecnologia de micro-ondas. No Brasil, o uso dessas substâncias é previsto na legislação como corante alimentício, porém, estes carotenoides apresentam extensas cadeias carbônicas insaturadas que permitem a adição de radicais livres e lhes conferem a capacidade de atuar como antioxidantes. As diferenças estruturais entre bixina e norbixina resultam em particularidades quanto à polaridade, solubilidade, coloração e, por consequência, determinam singulares aplicações tecnológicas. Nas concentrações previstas pelas agências reguladoras, o consumo desses carotenoides é seguro e além das aplicações como corante, podem ser utilizados pela indústria como antioxidantes naturais, oportunizando uma alternativa capaz de substituir ou minimizar o uso de aditivos sintéticos em produtos cárneos.

The Effect of Carotenoid Bixin on Chromosome Instability in HL60 Tumor Cell

The Effect of Carotenoid Bixin on Chromosome Instability in HL60 Tumor Cell

The chemistry and analysis of annatto food colouring: a review

Annatto food colouring (E160b) has a long history of use in the food industry for the colouring of a wide range of food commodities. The principal colouring component of annatto is the oil-soluble diapo carotenoid bixin, which is the methyl ester of the dicarboxylic acid norbixin and soluble in aqueous alkali. Bixin and norbixin, therefore, exhibit not only physicochemical properties normally associated with carotenoids, but also certain anomalous properties that have an impact on the stability, food colouring applications, and importantly the analysis of annatto. This review summarizes the key aspects of the structural determination of bixin (and norbixin) with special attention to cis-trans isomerization and how this links with its chemical structure, spectroscopic properties, and stability. The oxidative, thermal, and photo-stability of annatto and the subsequent implications for its use in the colouring of foods, food processing, and the analysis of foods and beverages are discussed along with important mechanistic, thermodynamic and kinetic aspects. The main analytical techniques used for the chemical characterization of annatto, i.e. spectrophotometry, nuclear magnetic resonance (NMR), chromatography (particularly high-performance liquid chromatography (HPLC)) and mass spectrometry are reviewed in detail and other methods are discussed. This links in with a review of the methods available for the detection and measurement of annatto in colour formulations and foods and beverages, which highlights the importance of the need for a good understanding and knowledge of the chemistry of bixin and norbixin in order to meet new analytical challenges.

Bixin and lycopene modulation of free radical generation induced by cisplatin–DNA interaction

This work evaluated the modulation of reactive oxygen species (ROS) produced by the cisplatin–human DNA interaction in a cell-free experimental model by the carotenoids bixin and lycopene, extracted from natural dietary sources and purified through luminol- and Cypridina luciferin methoxy-analogue (MCLA)-enhanced chemiluminescence assays. The results showed that the ROS generation by DNA–cisplatin interaction was inhibited by both lycopene and bixin in a concentration-dependent manner. At a concentration of 100 μM, lycopene and bixin inhibited superoxide anion ( O 2 - ) generation at 90% and 82%, respectively, and the total ROS generation at 44% and 42%, respectively. The formation of significant amounts of isomers or degradation products of both carotenoids was not observed after ROS scavenging, as evaluated by high-performance liquid chromatography. Taken together, these results suggest that carotenoids can be helpful to modulate the oxidative stress found in cancer therapy with cisplatin.

Separation of the Carotenoid Bixin from Annatto Seeds Using Thin-Layer and Column Chromatography

In this experiment the carotenoid bixin is isolated from annatto (Bixa orellana) seeds using column chromatography. The experiment has several key advantages over previous pigment separation experiments. First, unlike other experiments significant quantities of the carotenoid (typically 20 to 25 mg) can be isolated from small quantities of plant material. Second, in this experiment students learn how to choose the appropriate solvent for a chromatographic separation by analyzing several potential solvents using thin-layer chromatography. After isolation, the purified bixin is analyzed by UV–vis and IR spectroscopy.

Characterization of bixin by LC‐MS and LC‐NMR

An overview upon modern analytical techniques for the isolation, separation, and structural identification of the essential bioactive carotenoid bixin is given. Isolation from biological matrices is performed by matrix solid phase dispersion (MSPD). The extract is separated with shape-selective C(30 )columns. Structural assignment of the separated compounds is done by online LC-MS and capillary HPLC-NMR.

Triplet state energy of the carotenoid bixin determined by photoacoustic calorimetry

The triplet state energy level of the natural cis-carotenoid bixin (methyl hydrogen 9′ Z-6,6′-diapocarotene-6,6′-dioate) was determined using laser-induced photoacoustic calorimetry (PAC) in acetonitrile/methanol (1:1) solution. An energy-transfer process with anthracene as sensitizer in O 2-saturated solution was used to populate the carotenoid triplet state. The energy balance of the system allowed the calculation of the triplet energy content of bixin as E T = 18 ± 2 kcal/mol. The result is discussed in relation with both its singlet molecular oxygen quenching and cis → trans isomerization abilities. The quantum yield, Φ = 0.69, for the formation of either the triplet state or the singlet molecular oxygen by the sensitizer anthracene was also determined.