The Chemistry of Novel Xanthophyll Carotenoids

Jackson, Henry L.; Braun, Cristi L.; Ernst, Hansgeorg

doi:10.1016/j.amjcard.2008.02.008

Cited by 126 publications

(81 citation statements)

References 31 publications

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“…Many other xanthophyll carotenoids have been identified in some plants tissues and these include the highly valued ketocarotenoids (e.g. astaxanthin, capsanthin, capsorubin and canthaxanthin) and their biosynthesis has been reviewed elsewhere (Giuliano et al 2008;Jackson et al 2008).…”

Section: Carotenoid Biosynthesis and Regulationmentioning

confidence: 99%

Carotenoids in nature: insights from plants and beyond

Cazzonelli

2011

Functional Plant Biol.

446

245

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Abstract. Carotenoids are natural isoprenoid pigments that provide leaves, fruits, vegetables and flowers with distinctive yellow, orange and some reddish colours as well as several aromas in plants. Their bright colours serve as attractants for pollination and seed dispersal. Carotenoids comprise a large family of C 40 polyenes and are synthesised by all photosynthetic organisms, aphids, some bacteria and fungi alike. In animals carotenoid derivatives promote health, improve sexual behaviour and are essential for reproduction. As such, carotenoids are commercially important in agriculture, food, health and the cosmetic industries. In plants, carotenoids are essential components required for photosynthesis, photoprotection and the production of carotenoid-derived phytohormones, including ABA and strigolactone. The carotenoid biosynthetic pathway has been extensively studied in a range of organisms providing an almost complete pathway for carotenogenesis. A new wave in carotenoid biology has revealed implications for epigenetic and metabolic feedback control of carotenogenesis. Developmental and environmental signals can regulate carotenoid gene expression thereby affecting carotenoid accumulation. This review highlights mechanisms controlling (1) the first committed step in phytoene biosynthesis, (2) flux through the branch to synthesis of a-and b-carotenes and (3) metabolic feedback signalling within and between the carotenoid, MEP and ABA pathways.

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Section: Carotenoid Biosynthesis and Regulationmentioning

confidence: 99%

Carotenoids in nature: insights from plants and beyond

Cazzonelli

2011

Functional Plant Biol.

446

245

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“…Nowadays, a large proportion of commercial astaxanthin is produced synthetically 18 . This synthesis starts with a C-9 unit, ketoisophorone, which is obtained from petroleum feedstocks 19,20 . However, the growing demand for natural feeds and the high cost of synthetic pigments have led to the search of natural sources of astaxanthin, such as microalgae, yeasts and crustacean by-products [13][14][15]17,21,22 .…”

Section: Introductionmentioning

confidence: 99%

Astaxanthin: structural and functional aspects

Seabra

Pedrosa

2010

Rev. Nutr.

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1 Article based on L.M.J. SEABRA' s thesis project entitled "Litopenaeus vannamei shrimp: components of nutritional importance in meat and processing waste. A B S T R A C TAstaxanthin, a carotenoid belonging to the xanthophyll class, has stirred great interest due to its antioxidant capacity and its possible role in reducing the risk of some diseases. Astaxanthin occurs naturally in microalgae, such as Haematococcus pluvialis and the yeast Phaffia rhodozyma, and has also been considered to be the major carotenoid in salmon and crustaceans. Shrimp processing waste, which is generally discarded, is also an important source of astaxanthin. The antioxidant activity of astaxanthin has been observed to modulate biological functions related to lipid peroxidation, having beneficial effects on chronic diseases such as cardiovascular disease, macular degeneration and cancer. Researches have shown that both astaxanthin obtained from natural sources and its synthetic counterpart produce satisfactory effects, but studies in humans are limited to natural sources. There is no established nutritional recommendation regarding astaxanthin daily intake but most studies reported beneficial results from a daily intake of 4mg. Thus, this review discusses some aspects of the carotenoid astaxanthin, highlighting its chemical structure and antioxidant activity, and some studies that report its use in humans.Indexing terms: Antioxidants. Astaxanthin. Carotenoids. Chronic diseases. R E S U M O

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“…Carotenoids are natural pigments synthesized by bacteria, fungi, algae, and plants, and more than 750 different carotenoids have been isolated from natural sources (17). They possess important biological functions as protectants against light and oxygen excess in photosynthetic processes (32,38), and they have been proposed to reduce the risk of certain cancers, cardiovascular disease, and Alzheimer disease due to their antioxidative properties (20,46).…”

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confidence: 99%

Biosynthetic Pathway for γ-Cyclic Sarcinaxanthin in Micrococcus luteus : Heterologous Expression and Evidence for Diverse and Multiple Catalytic Functions of C ₅₀ Carotenoid Cyclases

et al. 2010

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We report the cloning and characterization of the biosynthetic gene cluster (crtE, crtB, crtI, crtE2, crtYg, crtYh, and crtX) of the ␥-cyclic C 50 carotenoid sarcinaxanthin in Micrococcus luteus NCTC2665. Expression of the complete and partial gene cluster in Escherichia coli hosts revealed that sarcinaxanthin biosynthesis from the precursor molecule farnesyl pyrophosphate (FPP) proceeds via C 40 lycopene, C 45 nonaflavuxanthin, C 50 flavuxanthin, and C 50 sarcinaxanthin. Glucosylation of sarcinaxanthin was accomplished by the crtX gene product. This is the first report describing the biosynthetic pathway of a ␥-cyclic C 50 carotenoid. Expression of the corresponding genes from the marine M. luteus isolate Otnes7 in a lycopene-producing E. coli host resulted in the production of up to 2.5 mg/g cell dry weight sarcinaxanthin in shake flasks. In an attempt to experimentally understand the specific difference between the biosynthetic pathways of sarcinaxanthin and the structurally related -cyclic decaprenoxanthin, we constructed a hybrid gene cluster with the ␥-cyclic C 50 carotenoid cyclase genes crtYg and crtYh from M. luteus replaced with the analogous -cyclic C 50 carotenoid cyclase genes crtYe and crtYf from the natural decaprenoxanthin producer Corynebacterium glutamicum. Surprisingly, expression of this hybrid gene cluster in an E. coli host resulted in accumulation of not only decaprenoxanthin, but also sarcinaxanthin and the asymmetric -and ␥-cyclic C 50 carotenoid sarprenoxanthin, described for the first time in this work. Together, these data contributed to new insight into the diverse and multiple functions of bacterial C 50 carotenoid cyclases as key catalysts for the synthesis of structurally different carotenoids.

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The Chemistry of Novel Xanthophyll Carotenoids

Cited by 126 publications

References 31 publications

Carotenoids in nature: insights from plants and beyond

Carotenoids in nature: insights from plants and beyond

Astaxanthin: structural and functional aspects

Biosynthetic Pathway for γ-Cyclic Sarcinaxanthin in Micrococcus luteus : Heterologous Expression and Evidence for Diverse and Multiple Catalytic Functions of C ₅₀ Carotenoid Cyclases

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The Chemistry of Novel Xanthophyll Carotenoids

Cited by 126 publications

References 31 publications

Carotenoids in nature: insights from plants and beyond

Carotenoids in nature: insights from plants and beyond

Astaxanthin: structural and functional aspects

Biosynthetic Pathway for γ-Cyclic Sarcinaxanthin in Micrococcus luteus : Heterologous Expression and Evidence for Diverse and Multiple Catalytic Functions of C 50 Carotenoid Cyclases

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Biosynthetic Pathway for γ-Cyclic Sarcinaxanthin in Micrococcus luteus : Heterologous Expression and Evidence for Diverse and Multiple Catalytic Functions of C ₅₀ Carotenoid Cyclases