Chemical structure of fucoxanthin (molecular formula: C42H58O6).

Chemical structure of fucoxanthin (molecular formula: C42H58O6).

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Seaweeds are important sources of carotenoids, and numerous studies have shown the beneficial effects of these pigments on human health. In the present study, Himanthalia elongata brown seaweed was extracted with a mixture of low polarity solvents, and the crude extract was separated using analytical thin-layer chromatography (TLC). The separated c...

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... The dried extract was then stored in vacuum desiccators for future use. The obtained dry extract ratio (DER) from the raw material was approximately 10-12%, as reported in references [10][11][12]. These extracts were subsequently employed in various aspects of the study. ...
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In this research, two primary bioactive components were isolated from Cynodon dactylon (L) Pers, commonly known as Durva grass. A gradient reverse phase High performance liquid chromatography coupled to Photodiode array detector (RP-HPLC-PDA) technique was established to identify and quantify these major bioactive constituents in 70% hydroalcoholic extracts of Cynodon dactylon (L) Pers. The chromatographic separation was achieved using an RP-C18 column (250 mm × 4.6 mm, 5 µm), Alliance (Waters) Empower3 liquid chromatography system, and a gradient mobile phase consisting of 5% acetic acid and acetonitrile. The flow rate was set at 1.2 mL/min, and a PDA detector at 320 nm was employed to analyze column effluents, targeting the active compounds' isotactic point. The retention times for the compounds p-coumeric and ferulic acid were determined as 24.11 and 31.52 min. The method exhibited linearity within the concentration range of 2–10 µg/mL, with regression coefficients of 0.998 and 0.9967 for the respective compounds. The mean recovery of p-coumeric and ferulic acid were found to between 102.64 and 109.44%. The RP-HPLC method was validated in accordance with ICH guidelines. KEY WORDS: 4-Hydroxycinnamic acid, Durva grass, Bioactive, Liquid-liquid extraction, RP-HPLC Bull. Chem. Soc. Ethiop. 2024, 38(6), 1533-1542. DOI: https://dx.doi.org/10.4314/bcse.v38i6.3
... LC-MS/MS analysis was carried out according to the method by Rajauria and Abu-Ghannam (2013) with Agilent Technologies 6520 Q-TOF. LC-MS/MS fitted with Mass Hunter Workstation software. ...
... The present study's analysis of in vitro and in vivo evidence indicates that fucoxanthin has numerous health advantages, although there has been little translational research success in clinical studies. Before a single chemical with many organ targets is developed into a pharmaceutical medicine, the activity-wise clinical trial can be conducted to validate the existing findings using human subjects due to its variety of health impacts (Rajauria and Abu-Ghannam, 2013). ...
... According to Rajauria and AbuGhannam (2013), Listeria monocytogenes showed a 10.89 mm zone of growth inhibition (ZOI). Fucoxanthin extracted from Turbinaria triquetra was found to exhibit the strongest antibacterial action against most of the pathogens including Bacillus cereus, Escherichia coli, Staphylococcus aureus, Klebsiella pneumoniae, Pseudomonas aeruginosa, and Bacillus subtilis (Rajauria and Abu-Ghannam, 2013). Zonglin Liu Z. et al. in 2019 reported the antibacterial activity of fucoxanthin isolated from the marine alga Undaria pinnatifida against five major human diseases. ...
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Fucoxanthin is a unique carotenoid present in brown seaweed due to the presence of an allenic bond in its structure. Its chemical composition consists of a central core that is cyclic, many conjugated double bonds, and several functional groups. Fucoxanthin plays a critical role in photosynthesis, absorbing light energy and transferring it to chlorophyll a. It has been demonstrated to have a variety of health advantages as well as protective effects against conditions including diabetes, liver cirrhosis, obesity, and malignant cancer, etc. Therefore, fucoxanthin can be employed as a strong pharmaceutical and dietary components to stop the spread of a wide array of infectious disorders. The present review focuses on the most recent research related to the pharmaceutical properties of fucoxanthin including antibacterial, antioxidant, anti-inflammatory, skin-protective, anti-obesity, anti-diabetic, and other qualities, including bioavailability and stability traits. This review seeks to support future biochemical research in order to create new pharmaceutical and dietary supplements that work with fucoxanthin and its many metabolites.
... The pigment chromatographic profiles showed the presence of xanthophylls including fucoxanthin, capsanthin, violaxanthin, zeaxanthin and cryptoxanthin in the different extracts corresponding to the winter season. In particular, violaxanthin and fucoxanthin have been previously described in brown algae (Pangestuti and Kim 2011;Rajauria and Abu-Ghannam 2013;Becerra 2016;Rajauria 2019). Several studies have shown that the administration of fucoxanthin obtained from U. pinnatifida to mice together with water significantly reduces the viability of prostate cancer cell lines, as well as the percentages of tumor-bearing mice and tumors in individuals (Hold and Kraan 2011). ...
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The alga Undaria pinnatifida is able to synthesize a great variety of bioactive metabolites of pharmaceutical and other industrial interest. However, this species has not yet been comprehensively studied in the Golfo San Jorge region (Chubut, Patagonia Argentina). Thus, in the present study, U. pinnatifida was collected at Golfo San Jorge, seasonally extracted and the chemical profile and biological activity evaluated by different techniques. The results showed that U. pinnatifida fundamentally biosynthesizes phenolic acids (caffeic and ferulic acids), flavonols and flavanol glycosides (quercetin, cacticin, quercitrin), carbohydrates, tannins, lipids, saponins, quinones, steroids, triterpenes and cardiotonic glycosides (of the k-strophanthoside, sciloriside, adynerin and convalatoxin types), with differences according to the season. The extracts also showed moderate antioxidant activity by the DPPH method and outstanding cytotoxic activity by the Artemia salina test. Based on the results obtained, U. pinnatifida can be considered as a potential source of bioactive molecules. Variations in the metabolites were observed throughout the seasons; particularly in the winter season, flavonoids were present in hexane and chloroform extracts, but not in methanol; tannins and other phenolic derivatives in the three winter extracts. This shows the importance of conducting seasonal studies to determine the best season for collection based on the metabolites to be studied.
... Das várias técnicas espectrométricas utilizadas para a identificação da fucoxantina, os infravermelhos com transformada de Fourier (FTIR) são utilizados na região de 500 a 4000 cm −1 para caracterizar a fracção purificada obtida a partir de extractos de H. elongata. Este mesmo estudo, foi completado com um detector UV-visível acoplado ao DAD (190 a 600 nm) fornecendo resultados de espectroscopia [117]. As técnicas de RMN são também ferramentas muito úteis para a identificação e determinação estrutural de fucoxantina e dos seus subprodutos. ...
... Para separar os lipídos neutros, pode-se usar a última solução e, para os polares, clorofórmio/acetona/metanol/ácido acético/água (50:20:10:10:5, v:v:v:v:v) [125]. Da mesma forma, outro trabalho usou clorofórmio/éter dietílico/n-hexano/ácido acético (10:3:1:1, v:v:v:v) para obter um extracto purificado de fucoxantina [117]. Outro método de purificação utilizado baseia-se em sistemas bifásicos aquosos de sal, mas este processo necessita de etapas adicionais de purificação. ...
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In recent decades, numerous marine organisms have been shown to be a promising source of compounds of interest to the food industry, such as vitamins, minerals, polyunsaturated fatty acids, peptides, phenolic compounds, pigments, etc. Algae are among these organisms and have been used as food and traditional remedies, initially in Asian countries but are currently used all around the world. In addition to its good nutritional values, the presence of bioactive compounds has drawn the attention of different areas of research and several industries with the aim of promoting its application as a sustainable raw material for the obtention of new ingredients. Taking this into account, the general objective of this doctoral thesis was to explore the potential of macroalgae from the Galician coastline as a source of bioactives, which resulted as a final purpose to define the optimal conditions for different methodologies for the extraction of fucoxanthin from Undaria pinnatifida. In an initial screening stage, eight species of macroalgae were considered as possible sources of active compounds: Ulva rigida and Codium tomentosum from the Cholophyta group (green algae), Palmaria palmata and Porphyra purpurea from the Rodophyta group (red algae) and Himanthalia elongata, Laminaria ochroleuca, S. latissima and U. pinnatifida from the Ochrophyta group (brown algae), which are widely present on the Galician coastline and are currently used in the food industry. The chemical composition, nutritional analysis and antioxidant and anti-inflammatory properties of these species were analyzed, revealing a great variability between species and groups. However, the four species of brown algae showed a higher extraction yield, which is a fundamental parameter for the design of subsequent industrial processes. Based on this, brown algae were selected as the study group for future analyses. In a second stage, it was decided to assess the potential of algae group as a source of bioactive compounds. For this a few more species of brown algae were added to the ones previously used, whose use is not currently widespread, in order to increase the range of evaluation. The added species were Ascophyllum nodosum, Bifurcaria bifurcata, Fucus spiralis, Pelvetia canaliculata and Sargassum muticum, which are all species you can also find in the Galician coastline. In this study, the pigment composition and biological properties of these nine species of brown algae was carried out, using different solvents (ethanol, acetone, hexane, chloroform and ethyl acetate), in order to evaluate the suitability of each one and select the most appropriate. The pigment analysis showed the presence of a wide variety of pigments, highlighting fucoxanthin, which was found in large quantities in all studied species but specially in U. pinnatifida. This carotenoid has gained relevance for a few decades, due to its numerous biological properties, corroborated both in vitro and in vivo. In fact, it has been considered as a functional ingredient for the development of various nutraceutical products, so this molecule was selected as the target compound and the algae U. pinnatifida as the principal extraction matrix. Additionally, ethanol and acetone were able to obtain higher yields, and they are both suitable to be used in the food industry, so they were chosen as extraction solvents. Once the target compound, matrix, and extraction solvents had been selected, the next step was to design a rapid method HPLC-DAD to quantify fucoxanthin from a large number of samples, in a simple way. This method was used for the optimization stage of the fucoxanthin extraction methods. Firstly, two kinetic studies were carried out to compare the efficiency of both solvents in fucoxanthin extraction. Based on the results, the most efficient solvent for its extraction was ethanol, which is considered a green solvent, suitable for the development of respectable industrial processes with the environment. Next, the extraction of fucoxanthin from U. pinnatifida was also carried out using innovative extraction techniques as MAE and UAE. This, methodology was used to determine on a laboratory scale, the conditions that allowed the best fucoxanthin extraction performance based on the previously selected factors. In the optimization, variables like power, extraction time and solvent concentration were evaluated, using a response surface methodology. This procedure was used with two different technologies: MAE and UAE, to contrast its effectiveness, and they were compared with a conventional method using a standard SAE. The results showed that through UAE technology the obtained yield was much higher than the one obtained with conventional techniques and also the ones reported in literature. Lastly, once the best conditions for extraction were determined and the kinetic of fucoxanthin’s extraction was known, the results were discussed with an algae factory and a pilot plant was designed, according to their preferences and specifications, to obtain extracts rich in fucoxanthin at a larger scale. In the pilot plant designed, the alga is washed, desiccated and pulverized preparing it to the extraction in an industrial reactor. After the extraction, the content is filtered, obtaining an extract rich in fucoxanthin, which is finally dehydrated and stored. The final extract was later incorporated into a food product with added nutritional value.
... In addition, [47] proved that the optimum separation of fucoxanthin from the crude extract using TLC occurs when Rf values are between 0.3 and 0.5. In the same way, Rajauria and Abu-Ghannam [48] demonstrated that fucoxanthin extracted from the brown seaweed Himanthalia elongate has an intense orange color bond after TLC migration at Rf = 0.36. ...
... The obtained results showed that the MIC of the purified fucoxanthin against L. monocytogenes was 1.25 ± 0.05 mg/mL. Rajauria and Abu-Ghannam [48] reported that the antimicrobial activity of purified fucoxanthin from Himanthalia elongate against L. monocytogenes was 1 mg/mL. It have been reported that fucoxanthin has an important antibacterial activity mainly against aerobic bacteria at concentrations ranging from 10 to 250 µg/mL, while, weak activities against anaerobic bacteria using doses greater than 1000 µg/mL [48]. ...
... Rajauria and Abu-Ghannam [48] reported that the antimicrobial activity of purified fucoxanthin from Himanthalia elongate against L. monocytogenes was 1 mg/mL. It have been reported that fucoxanthin has an important antibacterial activity mainly against aerobic bacteria at concentrations ranging from 10 to 250 µg/mL, while, weak activities against anaerobic bacteria using doses greater than 1000 µg/mL [48]. According to literature, natural compounds which have MIC above 1000 µg/mL were considered to have poor antibacterial activity [61,62]. ...
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... Previous research has found that seaweed has an antioxidant capability that might be utilised to generate biopharmaceuticals with extensive medicinal uses [27]. Seaweeds are known as an important source of carotenoids [28], alginates [10] and phenolic compounds [29]. It has been demonstrated that brown algae contain more polyphenols than red and green algae. ...
... The quantified amounts of phytochemicals found in H. elongata has been reported in Table 1 [20] 0.14 ± 0.02 g/g DW Dried sample Acid and enzymatic hydrolysis Reverse-phase HPLC [20] In a different study, TLC bioautography was used to extract several compounds from H. elongata in order to investigate their potential anti-inflammatory and antibacterial effects on Listeria monocytogenes bacterium. [28]. The It was also clear that among other seaweed species and specific nutritional/bioactive components, H. elongata had the greatest total phenolic concentration (14.0 g/kg) [11]. ...
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Himanthalia elongata is a brown seaweed containing several nutritional compounds and bioactive substances including antioxidants, dietary fibre, vitamins, fatty acids, amino acids, and macro- and trace- elements. A variety of bioactive compounds including phlorotannins, flavonoids, dietary fucoxanthin, hydroxybenzoic acid, hydroxycinnamic acid, polyphenols and carotenoids are also present in this seaweed. Multiple comparative studies were carried out between different seaweed species, wherein H. elongata was determined to exhibit high antioxidant capacity, total phenolic content, fucose content and potassium concentrations compared to other species. H. elongata extracts have also shown promising anti-hyperglycaemic and neuroprotective activities. H. elongata is being studied for its potential industrial food applications. In new meat product formulations, it lowered sodium content, improved phytochemical and fiber content in beef patties, improved properties of meat gel/emulsion systems, firmer and tougher with improved water and fat binding properties. This narrative review provides a comprehensive overview of the nutritional composition, bioactive properties, and food applications of H. elongata.
... Antilisterial activity was reported testing chemical standard and purified fucoxanthin (1 mg mL −1 ) from Himanthalia elongata (Rajauria and Abu-Ghannam 2013). No more references testing antimicrobial activity of fucoxanthin against L. monocytogenes have been found in literature, however, other works have also reported activity of both commercial and purified fucoxanthin against other Gram-positive and Gram-negative target strains by disk diffusion and microdilution methods, with the effect stronger against Gram-positive strains (Karpinski and Adamczak 2019;Liu et al. 2019). ...
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The objective of this work was to assess the antimicrobial effect of crude extracts and non-polar and mid-polar subfractions of the brown macroalga Ericaria selaginoides, using a mid-polarity extraction medium. The activity was evaluated through challenge testing against Listeria monocytogenes in Catalan “mató” (fresh cheese) selected as a food matrix. Three concentrations were tested, representing 2 ×, 4 × and 10 × Minimum Bactericidal Concentration values obtained for crude extract in previous in vitro assays. Ericaria selaginoides extracts inhibited L. monocytogenes growth in a dose-dependent manner. Intermediate concentrations of the three extracts were able to notably reduce the growth rate of the pathogen. Highest concentration of crude extract and non-polar subfraction were able to completely inhibit the growth of L. monocytogenes during the 10 days of storage at 8 °C. Moreover, a slight listericidal effect was observed in presence of the non-polar subfraction, reducing the L. monocytogenes level by ca. 3 log after 10 days of refrigerated storage. These results prove the potential of E. selaginoides extracts as a source of valuable antimicrobial compounds that can be used as natural food ingredients to develop safer fresh dairy food.
... Fucoxanthin is an oxygenated derivative of carotene; 40 its ultraviolet−visible spectroscopy absorption peak is usually between 440 and 470 nm and is widely reported as around 450 nm. 41 Different from common carotenoids, the molecular structure of fucoxanthin contains carbonyl, hydroxyl, carboxyl, and other groups as well as special structures such as allene bonds, conjugated double bonds, and monoepoxy groups. Due to the existence of these special functional groups, fucoxanthin is prone to oxidation and isomerization. ...
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The prevalence of neurodegenerative, cerebrovascular, and psychiatric diseases and other neurological disorders has increased dramatically worldwide. Fucoxanthin is an algal pigment with many biological functions, and there is rising evidence that fucoxanthin plays a preventive and therapeutic role in neurological disorders. This review focuses on the metabolism, bioavailability, and blood-brain barrier penetration of fucoxanthin. Furthermore, the neuroprotective potential of fucoxanthin in neurodegenerative diseases, cerebrovascular diseases, and psychiatric diseases as well as other neurological disorders such as epilepsy, neuropathic pain, and brain tumors by acting on multiple targets will be summarized. The multiple targets include regulating apoptosis, reducing oxidative stress, activating the autophagy pathway, inhibiting Aβ aggregation, improving dopamine secretion, reducing α-synuclein aggregation, attenuating neuroinflammation, modulating gut microbiota, and activating brain-derived neurotrophic factor, etc. Additionally, we look forward to brain-targeted oral transport systems due to the low bioavailability and blood-brain barrier permeability of fucoxanthin. We also propose exploring the systemic mechanisms of fucoxanthin metabolism and transport through the gut-brain process and envision new therapeutic targets for fucoxanthin to act on the central nervous system. Finally, we propose dietary fucoxanthin delivery interventions to achieve preventive effects on neurological disorders. This review provides a reference for the application of fucoxanthin in the neural field.
... Then, the plate was removed, the solvent evaporated at RT, and observed under visible light. The identification of the constituents was obtained by calculating the retention factor (Rf) as follows: Rf = compound migration distance (cm)/distance travelled by the eluent, and by comparison with the literature (Balasubramaniam et al., 2020;Cotas et al., 2019;Rajauria and Abu-Ghannam, 2013). All the experimental and environmental parameters were carefully controlled (chamber, reagents, environment conditions) to avoid their influence in the velocity of elution. ...
... After the TLC analyses, and considering the type of technique, the most concentrated pigments were isolated and solubilised in methanol according to Rajauria and Abu-Ghannam (2013), for further validation and quantification. The quantitative and qualitative analyses of those pigments were performed by UV-Vis (GBC Scientific Equipment Ltd. Cintra 101), with scanning from 400 to 800 nm; fucoxanthin quantification was performed by spectrophotometry (considering 445, 663 and 750 nm) following the equations described in the study of Wang et al. (2018). ...
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The present study aims to assess the potential exploitation of marine macroalgae waste using a cascade biorefinery approach. For that, biomass was collected from a northern Portugal beach, two different drying processes were employed (freeze-drying (FD) and sun-drying (SD)) and cascade extractions were conducted to obtain several extracts (fatty acids, pigments, polysaccharides) and a final extraction residue that were further characterised. The results show that the drying process affects the most sensitive compounds – e.g., pigments (fucoxanthin only detected in FD samples: raw biomass (1.1 mg.L−1) and polar cascade extract (1.5 mg.L−1)) – due to degradation processes, whereas the polymers, sugars and minerals are not affected. Carbohydrates, the prevailing compounds in marine macroalgae waste, are mainly composed by galactose and glucose. By comparing with the use of raw biomass, cascade extractions have a higher impact in the concentrations of monosaccharides and uronic acids (results from 28 up to 130 mg g−1; about fourfold and threefold higher for FD and SD extracts, respectively) and total minerals (results from 2417 up to 4507 mg.100 g−1; 1.6 and 1.4 higher for FD and SD final residues, respectively). This was not observed for the non-polar extracts due to the different extraction procedures and the low lipid content (maximum of 9.96 mg of fatty acids per gram, in the SD raw biomass). The mineral fraction was mainly composed by calcium, potassium, sodium and magnesium. The presence of alginic acid and other sulphated polymers and the low content of red seaweed polymers reflects the fact that the biomass is mainly composed by brown species. Taking into account the objective of exploring the full use of marine macroalgae waste to obtain diverse products with economic and environment advantages, also considering product quality increase and the absence of final residues, the application of the cascade process seems to be the most desirable route. The freeze-drying process should be further explored.