A chemical study of β-carotene oxidation by ozone in an organic model system and the identification of the resulting products

Benevides, Clícia Maria de Jesus; Veloso, Márcia Cristina da Cunha; Pereira, Pedro Afonso de Paula; Andrade, Jaílson Bittencourt de

doi:10.1016/j.foodchem.2010.11.082

Cited by 39 publications

(15 citation statements)

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“…Continued oxidation yields shorter apocarotene-dialdehydes of various chain lengths among which the shortest dialdehydes methylglyoxal and glyoxal cannot be oxidized further and represent possible terminal products of carotenoid oxidation ( Fig 7 ). Confirmatory, β-apocarotenals, apocarotene-dialdehydes, glyoxal and methylglyoxal are oxidatively generated from β-carotene after treatment with ozone in vitro [ 104 ]. Interestingly, we found increased levels of these metabolites in correlation with high β-carotene amounts which confirms that oxidative β-carotene decomposition occurs also in vivo and suggests short dialdehydes as putative end-product ( Fig 8 ).…”

Section: Discussionmentioning

confidence: 99%

Establishment of an Arabidopsis callus system to study the interrelations of biosynthesis, degradation and accumulation of carotenoids

et al. 2018

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The net amounts of carotenoids accumulating in plant tissues are determined by the rates of biosynthesis and degradation. While biosynthesis is rate-limited by the activity of PHYTOENE SYNTHASE (PSY), carotenoid losses are caused by catabolic enzymatic and non-enzymatic degradation. We established a system based on non-green Arabidopsis callus which allowed investigating major determinants for high steady-state levels of β-carotene. Wild-type callus development was characterized by strong carotenoid degradation which was only marginally caused by the activity of carotenoid cleavage oxygenases. In contrast, carotenoid degradation occurred mostly non-enzymatically and selectively affected carotenoids in a molecule-dependent manner. Using carotenogenic pathway mutants, we found that linear carotenes such as phytoene, phytofluene and pro-lycopene resisted degradation and accumulated while β-carotene was highly susceptible towards degradation. Moderately increased pathway activity through PSY overexpression was compensated by degradation revealing no net increase in β-carotene. However, higher pathway activities outcompeted carotenoid degradation and efficiently increased steady-state β-carotene amounts to up to 500 μg g-1 dry mass. Furthermore, we identified oxidative β-carotene degradation products which correlated with pathway activities, yielding β-apocarotenals of different chain length and various apocarotene-dialdehydes. The latter included methylglyoxal and glyoxal as putative oxidative end products suggesting a potential recovery of carotenoid-derived carbon for primary metabolic pathways. Moreover, we investigated the site of β-carotene sequestration by co-localization experiments which revealed that β-carotene accumulated as intra-plastid crystals which was confirmed by electron microscopy with carotenoid-accumulating roots. The results are discussed in the context of using the non-green calli carotenoid assay system for approaches targeting high steady-state β-carotene levels prior to their application in crops.

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Section: Discussionmentioning

confidence: 99%

Establishment of an Arabidopsis callus system to study the interrelations of biosynthesis, degradation and accumulation of carotenoids

et al. 2018

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“…The oxidation of carotenoids leads to the formation of trace quantities of several compounds with a low molecular weight. Depending on the concentration of ozone, the percentage decay of β-carotene increases, possibly due to the Criegee mechanism (Benevides et al, 2011).…”

Section: Iodine Value (Iv)mentioning

confidence: 99%

Chemical and structural variations in hazelnut and soybean oils after ozone treatments

et al. 2018

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SUMMARY:In the present work, the effect of ozone treatments on the structural properties of soybean oil (SBO) and hazelnut oil (HO) were investigated. The study presents the findings and results about the oxidation of HO and SBO with ozone, which has not been fully studied previously. The HO and SBO were treated with ozone gas for 1, 5, 15, 30, 60, 180 and 360 min. The ozone reactivity with the SBO and HO during the ozone treatment was analyzed by 1 H, 13 C NMR, FTIR and GC. The iodine value, viscosity and color variables (L*, a* and b*) of untreated and ozone treated oils were determined. Reaction products were identified according to the Criegee mechanism. New signals at 5.15 and 104.35 ppm were assigned to the ring protons of 1,2,4-trioxolane (secondary ozonide) in the ozonated oils in 1 H and 13 C NMR, respectively. Ozonated oils exhibited peaks at 9.75 and 2.43 ppm in 1 H and NMR, which corresponded to the aldehydic proton and α-methylene group and to the carbonyl carbon, respectively. The peak at 43.9 ppm in 13 C NMR was related to the α-methylene group and to the carbonyl carbon. The new signals formed in the ozonation process gradually increased with respect to ozone treatment time. After 360 min of ozone treatment, the carbon-carbon double bond signal, which belongs to the unsaturated fatty acids, disappeared completely in the spectrum. An increase in viscosity, a decrease in iodine value and a dramatic reduction in b* of the oil samples on (+) axis were observed with increased ozone treatment time. KEYWORDS: FTIR; GC; Hazelnut oil; NMR; Ozone; Soybean oil; Viscosity RESUMEN:Variaciones químicas y estructurales de aceites de avellana y soja después de tratamientos con ozono. En el presente trabajo se investigó el efecto de tratamientos con ozono sobre las propiedades estructurales de aceites de soja (SBO) y avellana (HO). El estudio muestra hallazgos y resultados sobre la oxidación de HO y SBO con ozono que no se habían presentado previamente. Los aceites HO y SBO son tratados con ozono gaseoso durante 1, 5, 15, 30, 60, 180 y 360 min. La reactividad del ozono con SBO y HO durante el tratamiento se analizó mediante 1 H, 13 C NMR, FTIR y GC. Se midieron las variables: índice de yodo, viscosidad y color (L *, a * y b *) de los aceites no tratados y tratados con ozono. Los productos de reacción se identificaron de acuerdo con el mecanismo de Criegee. Se asignaron nuevas señales a 5,15 y 104,35 ppm a los anillos protónicos de 1,2,4-trioxolano (ozónido secundario) en aceites ozonizados en 1 H y 13 C RMN, respectivamente. Los aceites ozonizados también mostraron picos a 9,75 y 2,43 ppm en 1 H NMR correspondientes al protón aldehídico y al grupo α-metileno, respectivamente. El pico a 43,9 ppm en 13 C RMN se relacionó con el C carbonilo del grupo α-metileno. Las nuevas señales formadas en el proceso de ozonización aumentaron gradualmente con respecto al tiempo de tratamiento con ozono. Después de un tratamiento de 360 minutos con ozono, la señal del doble enlace C=C que pertenece a los ácidos grasos insaturados ...

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“…Another subclass is that of secocarotenoids, in which a bond between two adjacent carbon atoms except between C(I) and C(6) in a ring has been broken [3,5]. The semi-β-carotenone (C 40 H 56 O 6 ) is an example identified as the product of β-carotene (C 40 H 56 ) oxidation in permanganate solutions [20].…”

Section: Structure Biosynthesis Synthesis and Applicationmentioning

confidence: 99%

Introductory Chapter: Carotenoids - A Brief Overview on Its Structure, Biosynthesis, Synthesis, and Applications

Fernandes¹,

Nascimento²,

Jacob‐Lopes³

et al. 2018

Progress in Carotenoid Research

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Currently, 1178 natural carotenoids have been properly characterized and reported in the literature, which present a huge structural diversity and physicochemical properties. This number comprises a wide distribution of these biomolecules in approximately 700 source organisms including plants, bacteria, fungi, and algae. Besides having a wide applicability as natural dyes, some carotenoids such as β-carotene already have another well-established application such as provitamin A activity. However, due to the structural diversity of these molecules, there are still numerous biochemical and physiological functions to be associated with this class of compounds. Accordingly, these characteristics enable a wide applicability, what drives the global carotenoid market. Thus, with the primary objective of addressing aspects regarding to basic science and applied carotenoid technology, a comprehensive description of the biology, biochemistry, and chemistry of these compounds will be described in this chapter.

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A chemical study of β-carotene oxidation by ozone in an organic model system and the identification of the resulting products

Cited by 39 publications

References 28 publications

Establishment of an Arabidopsis callus system to study the interrelations of biosynthesis, degradation and accumulation of carotenoids

Establishment of an Arabidopsis callus system to study the interrelations of biosynthesis, degradation and accumulation of carotenoids

Chemical and structural variations in hazelnut and soybean oils after ozone treatments

Introductory Chapter: Carotenoids - A Brief Overview on Its Structure, Biosynthesis, Synthesis, and Applications

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