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Keywords = loroxanthin

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23 pages, 1840 KiB  
Review
Distribution, Biosynthesis, and Function of Carotenoids in Oxygenic Phototrophic Algae
by Shinichi Takaichi
Mar. Drugs 2025, 23(2), 62; https://doi.org/10.3390/md23020062 - 31 Jan 2025
Cited by 1 | Viewed by 1817
Abstract
For photosynthesis, oxygenic phototrophic organisms necessarily contain not only chlorophylls but also carotenoids. Various carotenoids have been identified in algae and taxonomic studies of algae have been conducted. In this review, the relationship between the distribution of chlorophylls and carotenoids and the phylogeny [...] Read more.
For photosynthesis, oxygenic phototrophic organisms necessarily contain not only chlorophylls but also carotenoids. Various carotenoids have been identified in algae and taxonomic studies of algae have been conducted. In this review, the relationship between the distribution of chlorophylls and carotenoids and the phylogeny of sea and freshwater oxygenic phototrophs, including cyanobacteria, red algae, brown algae, and green algae, is summarized. These phototrophs contain division- or class-specific chlorophylls and carotenoids, such as fucoxanthin, peridinin, diadinoxanthin, and siphonaxanthin. The distribution of β-carotene and its derivatives, including β-carotene, zeaxanthin, violaxanthin, neoxanthin, diadinoxanthin, fucoxanthin, and peridinin (β-branch carotenoids), are limited to divisions of a part of Rhodophyta, Cryptophyta, Heterokontophyta, Haptophyta, and Dinophyta. Meanwhile, the distribution of α-carotene and its derivatives, such as lutein, loroxanthin, and siphonaxanthin (α-branch carotenoids), are limited to divisions of a part of Rhodophyta (macrophytic type), Cryptophyta, Euglenophyta, Chlorarachniophyta, and Chlorophyta. In addition, carotenogenesis pathways are also discussed based on the chemical structures of carotenoids and the known characteristics of carotenogenesis enzymes in other organisms. The specific genes and enzymes for carotenogenesis in algae are not yet known. Most carotenoids bind to membrane-bound pigment-protein complexes, such as reaction centers and light-harvesting complexes. Some carotenoids function in photosynthesis and are briefly summarized. Water-soluble peridinin-chlorophyll a-protein (PCP) and orange carotenoid protein (OCP) have also been characterized. This review is a summary and update from the previous review on the distribution of major carotenoids, primary carotenogenesis pathways, and the characteristics of carotenogenesis enzymes and genes. Full article
(This article belongs to the Special Issue Recent Advances in Marine-Derived Pigments)
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12 pages, 1471 KiB  
Article
CRISPR/Cas9-Mediated Knockout of the Lycopene ε-Cyclase for Efficient Astaxanthin Production in the Green Microalga Chlamydomonas reinhardtii
by Jacob Sebastian Kneip, Niklas Kniepkamp, Junhwan Jang, Maria Grazia Mortaro, EonSeon Jin, Olaf Kruse and Thomas Baier
Plants 2024, 13(10), 1393; https://doi.org/10.3390/plants13101393 - 17 May 2024
Cited by 17 | Viewed by 6863
Abstract
Carotenoids are valuable pigments naturally occurring in all photosynthetic plants and microalgae as well as in selected fungi, bacteria, and archaea. Green microalgae developed a complex carotenoid profile suitable for efficient light harvesting and light protection and harbor great capacity for carotenoid production [...] Read more.
Carotenoids are valuable pigments naturally occurring in all photosynthetic plants and microalgae as well as in selected fungi, bacteria, and archaea. Green microalgae developed a complex carotenoid profile suitable for efficient light harvesting and light protection and harbor great capacity for carotenoid production through the substantial power of the endogenous 2-C-methyl-D-erythritol 4-phosphate (MEP) pathway. Previous works established successful genome editing and induced significant changes in the cellular carotenoid content in Chlamydomonas reinhardtii. This study employs a tailored carotenoid pathway for engineered bioproduction of the valuable ketocarotenoid astaxanthin. Functional knockout of lycopene ε-cyclase (LCYE) and non-homologous end joining (NHEJ)-based integration of donor DNA at the target site inhibit the accumulation of α-carotene and consequently lutein and loroxanthin, abundant carotenoids in C. reinhardtii without changes in cellular fitness. PCR-based screening indicated that 4 of 96 regenerated candidate lines carried (partial) integrations of donor DNA and increased ß-carotene as well as derived carotenoid contents. Iterative overexpression of CrBKT, PacrtB, and CrCHYB resulted in a 2.3-fold increase in astaxanthin accumulation in mutant ΔLCYE#3 (1.8 mg/L) compared to the parental strain UVM4, which demonstrates the potential of genome editing for the design of a green cell factory for astaxanthin bioproduction. Full article
(This article belongs to the Special Issue Microalgae Photobiology, Biotechnology, and Bioproduction)
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18 pages, 2281 KiB  
Article
Comprehensive Analysis of Lutein and Loroxanthin in Scenedesmus obliquus: From Quantification to Isolation
by Ayşegül Erdoğan, Ayça Büşra Karataş, Dilan Demir, Zeliha Demirel, Merve Aktürk, Öykü Çopur, Ali Çağır and Meltem Conk-Dalay
Molecules 2024, 29(6), 1228; https://doi.org/10.3390/molecules29061228 - 9 Mar 2024
Cited by 3 | Viewed by 2718
Abstract
Carotenoids are hydrophobic pigments produced exclusively by plants, fungi, and specific microbes. Microalgae are well suited for the production of valuable carotenoids due to their rapid growth, efficient isoprenoid production pathway, and ability to store these compounds within their cells. The possible markets [...] Read more.
Carotenoids are hydrophobic pigments produced exclusively by plants, fungi, and specific microbes. Microalgae are well suited for the production of valuable carotenoids due to their rapid growth, efficient isoprenoid production pathway, and ability to store these compounds within their cells. The possible markets for bio-products range from feed additives in aquaculture and agriculture to pharmaceutical uses. The production of carotenoids in microalgae is affected by several environmental conditions, which can be utilized to enhance productivity. The current study focused on optimizing the extraction parameters (time, temperature, and extraction number) to maximize the yield of carotenoids. Additionally, the impact of various nitrogen sources (ammonia, nitrate, nitrite, and urea) on the production of lutein and loroxanthin in Scenedesmus obliquus was examined. To isolate the carotenoids, 0.20 g of biomass was added to 0.20 g of CaCO3 and 10.0 mL of ethanol solution containing 0.01% (w/v) pyrogallol. Subsequently, the extraction was performed using an ultrasonic bath for a duration of 10 min at a temperature of 30 °C. This was followed by a four-hour saponification process using a 10% methanolic KOH solution. The concentration of lutein and loroxanthin was measured using HPLC–DAD at 446 nm, with a flow rate of 1.0 mL/min using a Waters YMC C30 Carotenoid column (4.6 × 250 mm, 5 μm). The confirmation of carotenoids after their isolation using preparative chromatography was achieved using liquid chromatography–tandem mass spectrometry (LC–MS/MS) with an atmospheric pressure chemical ionization (APCI) probe and UV–vis spectroscopy. In summary, S. obliquus shows significant promise for the large-scale extraction of lutein and loroxanthin. The findings of this study provide strong support for the application of this technology to other species. Full article
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11 pages, 1852 KiB  
Article
Total Synthesis of Loroxanthin
by Yumiko Yamano, Mari Tanabe, Atsushi Shimada and Akimori Wada
Mar. Drugs 2022, 20(11), 658; https://doi.org/10.3390/md20110658 - 24 Oct 2022
Cited by 1 | Viewed by 2160
Abstract
The first total synthesis of loroxanthin (1) was accomplished by Horner-Wadsworth-Emmons reaction of C25-apocarotenal 8 having a silyl-protected 19-hydroxy moiety with C15-phosphonate 25 bearing a silyl-protected 3-hydroxy-ε-end group. Preparation of apocarotenal 8 was achieved via Stille coupling [...] Read more.
The first total synthesis of loroxanthin (1) was accomplished by Horner-Wadsworth-Emmons reaction of C25-apocarotenal 8 having a silyl-protected 19-hydroxy moiety with C15-phosphonate 25 bearing a silyl-protected 3-hydroxy-ε-end group. Preparation of apocarotenal 8 was achieved via Stille coupling reaction of alkenyl iodide 10 with alkenyl stananne 9, whereas phosphonate 25 was prepared through treatment of ally alcohol 23 with triethyl phosphite and ZnI2. The ally alcohol 23 was derived from the known (3R,6R)-3-hydroxy C15-aldehyde 20, which was obtained by direct optical resolution of racemate 20 using a semi-preparative chiral HPLC column. Full article
(This article belongs to the Special Issue Nutraceutical and Pharmaceutical Applications of Marine Carotenoids)
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15 pages, 930 KiB  
Article
Impact of Light Stress on the Synthesis of Both Antioxidants Polyphenols and Carotenoids, as Fast Photoprotective Response in Chlamydomonas reinhardtii: New Prospective for Biotechnological Potential of This Microalga
by Cecilia Faraloni, Tiziana Di Lorenzo and Alessandra Bonetti
Symmetry 2021, 13(11), 2220; https://doi.org/10.3390/sym13112220 - 20 Nov 2021
Cited by 23 | Viewed by 3544
Abstract
The aim of this study was to investigate the potential role of the microalga Chlamydomonas reinhardtii as an antioxidant source of enriched biomass. This microalga is a model organism deeply investigated for physiological studies, particularly considering carotenoid synthesis in response to stress, to [...] Read more.
The aim of this study was to investigate the potential role of the microalga Chlamydomonas reinhardtii as an antioxidant source of enriched biomass. This microalga is a model organism deeply investigated for physiological studies, particularly considering carotenoid synthesis in response to stress, to counteract the effects of the formation of free radicals. Less attention has been paid to the profile characterization of other antioxidant compounds, such as polyphenols, which can be synthesized, concomitantly with carotenoids, under photooxidative stress, especially high light. The cultures of C. reinhardtii were exposed to three different light intensities, 70, 800 and 1500 µmoles photons m−2 s−1. The increasing light intensity symmetrically induced the increasing accumulation of both carotenoids and phenolic compounds. The results showed that exposure to high light intensities caused the accumulation of electrons in the electron transport chain, with a reduction in photosynthetic activity. In the same cultures, high light intensity induced the strong increment of polyphenols such as gallic, chlorogenic and coumaric acids, which resulted 6.2-fold, 4-fold and 3.7-fold higher, respectively, than in cells exposed to the lowest intensities. As expected, at the highest light intensity, the strong induction of the xanthophyll cycle and the largest increment of loroxanthin, lutein, α-carotene and ß-carotene could be detected. Antioxidant properties doubled with respect to the initial time, both in acetone and methanol cellular extracts of these cultures, revealing a new potential role for biotechnological application of this microalga. Full article
(This article belongs to the Special Issue Photosynthetic Microorganisms: Cultivation and Application)
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18 pages, 764 KiB  
Review
Carotenoids in Algae: Distributions, Biosyntheses and Functions
by Shinichi Takaichi
Mar. Drugs 2011, 9(6), 1101-1118; https://doi.org/10.3390/md9061101 - 15 Jun 2011
Cited by 652 | Viewed by 31664
Abstract
For photosynthesis, phototrophic organisms necessarily synthesize not only chlorophylls but also carotenoids. Many kinds of carotenoids are found in algae and, recently, taxonomic studies of algae have been developed. In this review, the relationship between the distribution of carotenoids and the phylogeny of [...] Read more.
For photosynthesis, phototrophic organisms necessarily synthesize not only chlorophylls but also carotenoids. Many kinds of carotenoids are found in algae and, recently, taxonomic studies of algae have been developed. In this review, the relationship between the distribution of carotenoids and the phylogeny of oxygenic phototrophs in sea and fresh water, including cyanobacteria, red algae, brown algae and green algae, is summarized. These phototrophs contain division- or class-specific carotenoids, such as fucoxanthin, peridinin and siphonaxanthin. The distribution of α-carotene and its derivatives, such as lutein, loroxanthin and siphonaxanthin, are limited to divisions of Rhodophyta (macrophytic type), Cryptophyta, Euglenophyta, Chlorarachniophyta and Chlorophyta. In addition, carotenogenesis pathways are discussed based on the chemical structures of carotenoids and known characteristics of carotenogenesis enzymes in other organisms; genes and enzymes for carotenogenesis in algae are not yet known. Most carotenoids bind to membrane-bound pigment-protein complexes, such as reaction center, light-harvesting and cytochrome b6f complexes. Water-soluble peridinin-chlorophyll a-protein (PCP) and orange carotenoid protein (OCP) are also established. Some functions of carotenoids in photosynthesis are also briefly summarized. Full article
(This article belongs to the Special Issue Marine Carotenoids (Special Issue))
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