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17 pages, 10826 KiB

Open AccessArticle

Palmitoylation of Metazoan Carotenoid Oxygenases

by Sheetal Uppal, Igor B. Rogozin, T.Michael Redmond and Eugenia Poliakov

Molecules 2020, 25(8), 1942; https://doi.org/10.3390/molecules25081942 - 22 Apr 2020

Cited by 5 | Viewed by 3187

Abstract

Abundant in nature, carotenoids are a class of fat-soluble pigments with a polyene tetraterpenoid structure. They possess antioxidant properties and their consumption leads to certain health benefits in humans. Carotenoid cleavage oxygenases (CCOs) are a superfamily of enzymes which oxidatively cleave carotenoids and [...] Read more.

Abundant in nature, carotenoids are a class of fat-soluble pigments with a polyene tetraterpenoid structure. They possess antioxidant properties and their consumption leads to certain health benefits in humans. Carotenoid cleavage oxygenases (CCOs) are a superfamily of enzymes which oxidatively cleave carotenoids and they are present in all kingdoms of life. Complexity of CCO evolution is high. For example, in this study we serendipitously found a new family of eukaryotic CCOs, the apocarotenoid oxygenase-like (ACOL) family. This family has several members in animal genomes and lacks the animal-specific amino acid motif PDPCK. This motif is likely to be associated with palmitoylation of some animal CCOs. We recently demonstrated that two mammalian members of the carotenoid oxygenase family retinal pigment epithelial-specific 65 kDa protein (RPE65) and beta-carotene oxygenase 2 (BCO2) are palmitoylated proteins. Here we used the acyl-resin-assisted capture (acyl-RAC) method to demonstrate protein palmitoylation and immunochemistry to localize mouse BCO2 (mBCO2) in COS7 cell line in the absence and presence of its substrate β-carotene. We demonstrate that mBCO2 palmitoylation depends on the evolutionarily conserved motif PDPCK and that metazoan family members lacking the motif (Lancelet beta-carotene oxygenase-like protein (BCOL) and Acropora ACOL) are not palmitoylated. Additionally, we observed that the palmitoylation status of mBCO2 and its membrane association depend on the presence of its substrate β-carotene. Based on our results we conclude that most metazoan carotenoid oxygenases retain the evolutionarily conserved palmitoylation PDPCK motif to target proteins to internal membranes depending on substrate status. Exceptions are in the secreted BCOL subfamily and the strictly cytosolic ancient ACOL subfamily of carotenoid oxygenases. Full article

(This article belongs to the Special Issue Carotenoids)

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17 pages, 3008 KiB

Open AccessArticle

Deciphering Pathways for Carotenogenesis in Haloarchaea

by Micaela Giani, Jose María Miralles-Robledillo, Gloria Peiró, Carmen Pire and Rosa María Martínez-Espinosa

Molecules 2020, 25(5), 1197; https://doi.org/10.3390/molecules25051197 - 6 Mar 2020

Cited by 20 | Viewed by 4792

Abstract

Bacterioruberin and its derivatives have been described as the major carotenoids produced by haloarchaea (halophilic microbes belonging to the Archaea domain). Recently, different works have revealed that some haloarchaea synthetize other carotenoids at very low concentrations, like lycopene, lycopersene, cis- and trans-phytoene, cis- [...] Read more.

Bacterioruberin and its derivatives have been described as the major carotenoids produced by haloarchaea (halophilic microbes belonging to the Archaea domain). Recently, different works have revealed that some haloarchaea synthetize other carotenoids at very low concentrations, like lycopene, lycopersene, cis- and trans-phytoene, cis- and trans-phytofluene, neo-β-carotene, and neo-α-carotene. However, there is still controversy about the nature of the pathways for carotenogenesis in haloarchaea. During the last decade, the number of haloarchaeal genomes fully sequenced and assembled has increased significantly. Although some of these genomes are not fully annotated, and many others are drafts, this information provides a new approach to exploring the capability of haloarchaea to produce carotenoids. This work conducts a deeply bioinformatic analysis to establish a hypothetical metabolic map connecting all the potential pathways involved in carotenogenesis in haloarchaea. Special interest has been focused on the synthesis of bacterioruberin in members of the Haloferax genus. The main finding is that in almost all the genus analyzed, a functioning alternative mevalonic acid (MVA) pathway provides isopentenyl pyrophosphate (IPP) in haloarchaea. Then, the main branch to synthesized carotenoids proceeds up to lycopene from which β-carotene or bacterioruberin (and its precursors: monoanhydrobacterioriberin, bisanhydrobacterioruberin, dihydrobisanhydrobacteriuberin, isopentenyldehydrorhodopsin, and dihydroisopenthenyldehydrorhodopsin) can be made. Full article

(This article belongs to the Special Issue Carotenoids)

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16 pages, 3003 KiB

Open AccessArticle

Isotonic Beverage Pigmented with Water-Dispersible Emulsion from Astaxanthin Oleoresin

by Pedro Cerezal Mezquita, Carolina Espinosa Álvarez, Jenifer Palma Ramírez, Waldo Bugueño Muñoz, Francisca Salinas Fuentes and María del Carmen Ruiz-Domínguez

Molecules 2020, 25(4), 841; https://doi.org/10.3390/molecules25040841 - 14 Feb 2020

Cited by 9 | Viewed by 4767

Abstract

Astaxanthin is a powerful antioxidant, because it neutralizes free radicals and plays a vital role in the prevention of human diseases. The objective of this work was to develop an isotonic beverage (IB) of orange-red color, using an astaxanthin oleoresin emulsion (AOE) that [...] Read more.

Astaxanthin is a powerful antioxidant, because it neutralizes free radicals and plays a vital role in the prevention of human diseases. The objective of this work was to develop an isotonic beverage (IB) of orange-red color, using an astaxanthin oleoresin emulsion (AOE) that is dispersible in water. This was carried out in order to simulate the color of commercial isotonic beverages (CIB) prepared from artificial pigments. The size of the AOE micelles ranged from 0.15 to 7.60 µm². The color difference (ΔE) was similar for the samples exposed to dark as well as light conditions. The samples subjected to light stress showed pigment degradation after seven days, followed by a decrease in the concentration of astaxanthin; whereas, the samples exposed to dark conditions remained stable for seven days and then showed a decrease in the concentration of astaxanthin (this decrease ranged from 65% to 76% when compared to the initial content) after a period of 91 days. For the astaxanthin oleoresin (AO) and AOE, the oxygen radical absorbance capacity (ORAC) values reached 5224 and 1968 µmol of trolox equivalents (TE)/100 g, respectively. When exposed to light conditions, the addition of AOE in the IB led to its rapid degradation, while it remained stable in the samples exposed to the dark conditions. Full article

(This article belongs to the Special Issue Carotenoids)

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21 pages, 2485 KiB

Open AccessArticle

Study on the Synthesis, Antioxidant Properties, and Self-Assembly of Carotenoid–Flavonoid Conjugates

by Ildikó Línzembold, Dalma Czett, Katalin Böddi, Tibor Kurtán, Sándor Balázs Király, Gergely Gulyás-Fekete, Anikó Takátsy, Tamás Lóránd, József Deli, Attila Agócs and Veronika Nagy

Molecules 2020, 25(3), 636; https://doi.org/10.3390/molecules25030636 - 1 Feb 2020

Cited by 10 | Viewed by 3834

Abstract

Flavonoids and carotenoids possess beneficial physiological effects, such as high antioxidant capacity, anticarcinogenic, immunomodulatory, and anti-inflammatory properties, as well as protective effects against UV light. The covalent coupling of hydrophobic carotenoids with hydrophilic flavonoids, such as daidzein and chrysin, was achieved, resulting in [...] Read more.

Flavonoids and carotenoids possess beneficial physiological effects, such as high antioxidant capacity, anticarcinogenic, immunomodulatory, and anti-inflammatory properties, as well as protective effects against UV light. The covalent coupling of hydrophobic carotenoids with hydrophilic flavonoids, such as daidzein and chrysin, was achieved, resulting in new amphipathic structures. 7-Azidohexyl ethers of daidzein and chrysin were prepared in five steps, and their azide-alkyne [4 + 2] cycloaddition with pentynoates of 8′-apo-β-carotenol, zeaxanthin, and capsanthin afforded carotenoid–flavonoid conjugates. The trolox-equivalent antioxidant capacity against ABTS^•+ radical cation and self-assembly of the final products were examined. The 1:1 flavonoid–carotenoid hybrids generally showed higher antioxidant activity than their parent flavonoids but lower than that of the corresponding carotenoids. The diflavonoid hybrids of zeaxanthin and capsanthin, however, were found to exhibit a synergistic enhancement in antioxidant capacities. ECD (electronic circular dichroism) and UV-vis analysis of zeaxanthin–flavonoid conjugates revealed that they form different optically active J-aggregates in acetone/water and tetrahydrofuran/water mixtures depending on the solvent ratio and type of the applied aprotic polar solvent, while the capsanthin derivatives showed no self-assembly. The zeaxanthin bis-triazole conjugates with daidzein and with chrysin, differing only in the position of a phenolic hydroxyl group, showed significantly different aggregation profile upon the addition of water. Full article

(This article belongs to the Special Issue Carotenoids)

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10 pages, 1311 KiB

Open AccessArticle

α-Ionone, an Apocarotenoid, Induces Plant Resistance to Western Flower Thrips, Frankliniella occidentalis, Independently of Jasmonic Acid

by Mika Murata, Tetsuya Kobayashi and Shigemi Seo

Molecules 2020, 25(1), 17; https://doi.org/10.3390/molecules25010017 - 19 Dec 2019

Cited by 23 | Viewed by 3621

Abstract

Apocarotenoids, such as β-cyclocitral, α-ionone, β-ionone, and loliolide, are derived from carotenes via chemical or enzymatic processes. Recent studies revealed that β-cyclocitral and loliolide play an important role in various aspects of plant physiology, such as stress responses, plant growth, and herbivore resistance. [...] Read more.

Apocarotenoids, such as β-cyclocitral, α-ionone, β-ionone, and loliolide, are derived from carotenes via chemical or enzymatic processes. Recent studies revealed that β-cyclocitral and loliolide play an important role in various aspects of plant physiology, such as stress responses, plant growth, and herbivore resistance. However, information on the physiological role of α-ionone is limited. We herein investigated the effects of α-ionone on plant protection against herbivore attacks. The pretreatment of whole tomato (Solanum lycopersicum) plants with α-ionone vapor decreased the survival rate of western flower thrips (Frankliniella occidentalis) without exhibiting insecticidal activity. Exogenous α-ionone enhanced the expression of defense-related genes, such as basic β-1,3-glucanase and basic chitinase genes, in tomato leaves, but not that of jasmonic acid (JA)- or loliolide-responsive genes. The pretreatment with α-ionone markedly decreased egg deposition by western flower thrips in the JA-insensitive Arabidopsis (Arabidopsis thaliana) mutant coi1-1. We also found that common cutworm (Spodoptera litura) larvae fed on α-ionone-treated tomato plants exhibited a reduction in weight. These results suggest that α-ionone induces plant resistance to western flower thrips through a different mode of action from that of JA and loliolide. Full article

(This article belongs to the Special Issue Carotenoids)

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19 pages, 1130 KiB

Open AccessArticle

The Profile of Carotenoids and Other Bioactive Molecules in Various Pumpkin Fruits (Cucurbita maxima Duchesne) Cultivars

by Bartosz Kulczyński and Anna Gramza-Michałowska

Molecules 2019, 24(18), 3212; https://doi.org/10.3390/molecules24183212 - 4 Sep 2019

Cited by 60 | Viewed by 8557

Abstract

Bioactive compounds are significant to human nutrition. They are beneficial to health as they inhibit the development of numerous diseases of affluence. Scientists continuously search for natural sources of these components. At present, the chemical composition of various plants is under investigation. Many [...] Read more.

Bioactive compounds are significant to human nutrition. They are beneficial to health as they inhibit the development of numerous diseases of affluence. Scientists continuously search for natural sources of these components. At present, the chemical composition of various plants is under investigation. Many researchers are interested in pumpkin (Cucurbita L. spp.). Different organs of this plant (pulp, seeds, flowers, leaves, shoots, roots) are consumed almost all over the world. They contain large amounts of bioactive compounds. Pumpkin pulp is used to prepare various dishes. It is also widely used in the food industry for the production of pastries, baked goods, juices, jams, marinades, and baby food. The content of carotenoids in the pumpkin has been documented in a large number of publications. However, so far there has been no complex analysis of the profile of other bioactive compounds. This article analyses 11 pumpkin cultivars of the Cucurbita maxima Duchesne species. It compares the chemical composition of the pulp and analyses the content of bioactive compounds such as carotenoids, polyphenols (flavonols and phenolic acids), tocopherols, minerals (K, Ca, Mg, Na, Fe, Zn, Cu, Mn), vitamins (C, B1, folates). In view of available information, the study provides an innovative approach. The analysis showed high diversity in the concentration of individual components between the cultivars. The research proved that pumpkin pulp was not only a source of carotenoids but also other bioactive compounds. Full article

(This article belongs to the Special Issue Carotenoids)

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16 pages, 3401 KiB

Open AccessArticle

Optimization and Formulation of Fucoxanthin-Loaded Microsphere (F-LM) Using Response Surface Methodology (RSM) and Analysis of Its Fucoxanthin Release Profile

by Irwandi Jaswir, Dedi Noviendri, Muhammad Taher, Farahidah Mohamed, Fitri Octavianti, Widya Lestari, Ali Ghufron Mukti, Sapta Nirwandar and Bubaker B. Hamad Almansori

Molecules 2019, 24(5), 947; https://doi.org/10.3390/molecules24050947 - 7 Mar 2019

Cited by 27 | Viewed by 4837

Abstract

Fucoxanthin has interesting anticancer activity, but is insoluble in water, hindering its use as a drug. Microencapsulation is used as a technique for improving drug delivery. This study aimed to formulate fucoxanthin-loaded microspheres (F-LM) for anticancer treatment of H1299 cancer cell lines and [...] Read more.

Fucoxanthin has interesting anticancer activity, but is insoluble in water, hindering its use as a drug. Microencapsulation is used as a technique for improving drug delivery. This study aimed to formulate fucoxanthin-loaded microspheres (F-LM) for anticancer treatment of H1299 cancer cell lines and optimize particle size (PS) and encapsulation efficiency (EE). Using response surface methodology (RSM), a face centered central composite design (FCCCD) was designed with three factors: Polyvinylalcohol (PVA), poly(d,l-lactic-co-glycolic acid) (PLGA), and fucoxanthin concentration. F-LM was produced using a modified double-emulsion solvent evaporation method. The F-LM were characterized for release profile, release kinetics, and degradation pattern. Optimal F-LM PS and EE of 9.18 µm and 33.09%, respectively, with good surface morphology, were achieved from a 0.5% (w/v) PVA, 6.0% (w/v) PLGA, 200 µg/mL fucoxanthin formulation at a homogenization speed of 20,500 rpm. PVA concentration was the most significant factor (p < 0.05) affecting PS. Meanwhile, EE was significantly affected by interaction between the three factors: PVA, PLGA, and fucoxanthin. In vitro release curve showed fucoxanthin had a high burst release (38.3%) at the first hour, followed by a sustained release stage reaching (79.1%) within 2 months. Release kinetics followed a diffusion pattern predominantly controlled by the Higuchi model. Biodegradability studies based on surface morphology changes on the surface of the F-LM, show that morphology changed within the first hour, and F-LM completely degraded within 2 months. RSM under FCCCD design improved the difference between the lowest and highest responses, with good correlation between observed and predicted values for PS and EE of F-LM. Full article

(This article belongs to the Special Issue Carotenoids)

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15 pages, 2301 KiB

Open AccessArticle

Metabolic Profiling of Nine Mentha Species and Prediction of Their Antioxidant Properties Using Chemometrics

by Yun Ji Park, Seung-A Baek, Yongsoo Choi, Jae Kwang Kim and Sang Un Park

Molecules 2019, 24(2), 258; https://doi.org/10.3390/molecules24020258 - 11 Jan 2019

Cited by 37 | Viewed by 9039

Abstract

Mentha species are well recognized for their medicinal and aromatic properties. The comprehensive metabolite profiles of nine Mentha species have been determined. The extracts of these Mentha species were also screened for antioxidant and free radical scavenging activities. Forty-seven hydrophilic and seventeen lipophilic [...] Read more.

Mentha species are well recognized for their medicinal and aromatic properties. The comprehensive metabolite profiles of nine Mentha species have been determined. The extracts of these Mentha species were also screened for antioxidant and free radical scavenging activities. Forty-seven hydrophilic and seventeen lipophilic compounds were identified and quantified from the selected Mentha species. Also, eleven phenolic compounds, riboflavin and eight carotenoids were present, and their composition and content varied among the various Mentha species. The different Mentha species exhibited a range of antioxidant potencies. Horse mint especially exhibited the strongest antioxidant capacities (1,1-diphenyl-2-picryl-hydrazyl (DPPH), hydrogen peroxide, and reducing power assay) among the nine Mentha species. A difference between different samples from the same species was not observed by multivariate analysis. A high correlation between metabolites involved in closely linked biosynthetic pathways has been indicated. The projection to latent structure method, using the partial least squares (PLS) method, was applied to predict antioxidant capacities based on the metabolite profiles of Mentha leaves. According to the PLS analysis, several carotenoid contents, such as E-β-carotene, 9Z-β-carotene, 13Z-β-carotene and lutein, as well as phenolic compounds, showed a positive relationship in reducing the power of Mentha extracts. Horse mint is a good candidate because of its high antioxidant efficacy among the nine Mentha species included in the study. Full article

(This article belongs to the Special Issue Carotenoids)

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Review

Jump to: Research

28 pages, 1691 KiB

Open AccessReview

Supramolecular Carotenoid Complexes of Enhanced Solubility and Stability—The Way of Bioavailability Improvement

by A. Ligia Focsan, Nikolay E. Polyakov and Lowell D. Kispert

Molecules 2019, 24(21), 3947; https://doi.org/10.3390/molecules24213947 - 31 Oct 2019

Cited by 56 | Viewed by 5693

Abstract

Carotenoids are natural dyes and antioxidants widely used in food processing and in therapeutic formulations. However, their practical application is restricted by their high sensitivity to external factors such as heat, light, oxygen, metal ions and processing conditions, as well as by extremely [...] Read more.

Carotenoids are natural dyes and antioxidants widely used in food processing and in therapeutic formulations. However, their practical application is restricted by their high sensitivity to external factors such as heat, light, oxygen, metal ions and processing conditions, as well as by extremely low water solubility. Various approaches have been developed to overcome these problems. In particular, it was demonstrated that application of supramolecular complexes of “host-guest” type with water-soluble nanoparticles allows minimizing the abovementioned disadvantages. From this point of view, nanoencapsulation of carotenoids is an effective strategy to improve their stability during storage and food processing. Also, nanoencapsulation enhances bioavailability of carotenoids via modulating their release kinetics from the delivery system, influencing the solubility and absorption. In the present paper, we present the state of the art of carotenoid nanoencapsulation and summarize the data obtained during last five years on preparation, analysis and reactivity of carotenoids encapsulated into various nanoparticles. The possible mechanisms of carotenoids bioavailability enhancement by multifunctional delivery systems are also discussed. Full article

(This article belongs to the Special Issue Carotenoids)

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