Carotenoids chemical structure

Carotenoid chemical structure is usually not affected by the physical quenching. Another mechanism can occur in which a carotenoid chemically quenches singlet oxygen and is thus transformed in derived products. ... 

FIGURE 3.3.1 Chemical structures of carotenoid oxidation products occurring in nature. The compound numbers correspond to those cited in Britton, G. et al., Carotenoids Handbook ... 

Owing to their chemical structure, carotenes as polyterpenoids are hydrophobic in nature (Britton et al., 2004). Therefore, as it might be expected, the carotenes are bound within the hydrophobic core of the lipid membranes. Polar carotenoids, with the molecules terminated on one or two sides with the oxygen-bearing substitutes, also bind to the lipid bilayer in such a way that the chromophore, constituted by the polyene backbone is embedded in the hydrophobic core of the membrane. There are several lines of evidence for such a localization of carotenoids with respect to the lipid bilayers. 

Carotenoid molecules incorporated into the lipid membranes considerably interfere with both the structural and the dynamic membrane properties. Both effects are directly related to the chemical structure of carotenoid molecules. Importantly, it is the rigid, rod-like backbone of the carotenoids,... 

More than 600 different carotenoids from natural sources have been isolated and characterized. Physical properties and natural functions and actions of carotenoids are determined by their chemical properties, and these properties are defined by their molecular structures. Carotenoids consist of 40 carbon atoms (tetraterpenes) with conjugated double bonds. They consist of eight isoprenoid units j oined in such a manner that the arrangement of isoprenoid units is reversed at the center of the molecule so that the two central methyl groups are in a 1,6-position and the remaining nonterminal methyl groups are in a 1,5-position relationship. They can be acyclic or cyclic (mono- or bi-, alicyclic or aryl). Whereas green leaves contain unesterified hydroxy carotenoids, most carotenoids in ripe fruit are esterified with fatty acids. However, those of a few... 

A large variety of phytochemicals are found within agricultural commodities. This chapter focuses on four main groups phenolics, carotenoids, sterols, and alkaloids. In addition, recent research related to the health benefits of these phytochemicals will be briefly reviewed. Table 9.1 summarizes the main chemical structure and solubility in organic solvents of phytochemicals such as phenolics (flavonoids), carotenoids, sterols, and alkaloids. 

The chemical structure of some typical carotenoids is shown in Fig. 8.2. Beta-carotene occurs in nature usually associated with a number of chemically closely related pigments and extracts have been used as food colorants for many years. For example, palm oil has a high concentration of carotenoid pigments, primarily beta-carotene and about 20 others. Cmde palm oil has been used extensively as a cooking oil because of its desirable flavor and as a general... 

The success of the carotenoid extracts led to the commercialization of synthetic carotenoids, some with the same chemical structure as those in the plant extracts and others with modifications to improve their technological properties. The yellow beta-carotene was synthesized in 1950, followed by the orange beta-8-carotenal in 1962 and the red canthaxanthin in 1964. A number of others soon followed, methyl and ethyl esters of carotenoic acid, citraxanthin, zeaxanthin, astaxanthin, and recently lutein. 

Because of their versatility and simplicity, TLC methods have been frequently applied to the separation and semi-quantitative determination of carotenoid pigments in synthetic mixtures and various biological matrices. The retention of pure carotenoid standards has been measured in different TLC systems. Separations have been carried out on silica plates using three mobile phases (1) petroleum ether-acetone, 6 4 v/v (2) petroleum ether-tert-butanol 8 2 v/v, and (3) methanol-benzene-ethyl acetate 5 75 20 v/v. Carotenoids were dissolved in benzene and applied to the plates. Developments were performed in presaturated normal chambers. The chemical structure and the Rv values of the analytes measured in the three mobile phases are listed in Table 2.1. It was concluded from the retention data that mobile phase 3 is the most suitable for the separation of this set of carotenoids [13],... 

Besides the great pigment classes such as carotenoids, flavonoids, anthocyanins and chlorophylls a wide variety of other pigments have been separated, quantitated and identified by different liquid chromatograpchic techniques. The chemical structures of these pigments show high diversity. Unfortunately, in the majority of cases the biological activity of these... 

The primary chemicals of interest in chilies are capsaicinoids, namely capsaicin (0.02%) and dihydrocapsaicin (figure 8.11). Also found are flavonoids, carotenoids (capsanthin), steroid saponins (capsicidin), and ascorbic acid or vitamin C (0.2%). Capsaicin has a vanilloid chemical structure. Mechanisms of Action... 

ANNATTO FOOD COLORS. These colors are natural carotenoid colorants derived from the seed of the tropical annatto tree (Bixa nrellana). The surface of the seeds contains a highly colored resin, consisting primarily of the carotenoid bixin. The bixin is extracted from the seed by a special process to produce a pure, soluble colorant. Bixin, one of the relatively few naturally occurring cts compounds, has a chemical structure similar to the nucleus of carotene with a free and esterified carboxyl group as end groups. Its formula is CM LoCL. (See Fig. I). 

Saffron extract contains many carotenoids such as crocetin, crocetin di-glucose ester, crocetin gentiobiose glucose ester, and crocin (crocetin di-gentiobiose ester), whose chemical structures are shown in Figure 58.1. These carotenoids scavenge free radicals, especially superoxide anions, and so may protect cells from oxidative stress. Indeed, it has been demonstrated that these carotenoids are useful in sperm cryoconservation and in protecting heptocytes from toxins. 

Figure 9.38 Chemical structures of select carotenoids can be divided into two groups the carotenes (e.g., /3-carotene) which are hydrocarbons and the xanthophylls (e.g., violaxanthin, fucoxanthin) which are molecules that contain at least one oxygen atom.

Liaaen-Jensen, S., Cohen-Bazire, G. and Stanier, R.Y. 1961. Biosynthesis of carotenoids in purple bacteria A reevaluation based on considerations of chemical structure. Nature (London), 192,1168-1172. 

Figure 29-3. Chemical structures of important vitamin A species and the provitamin A carotenoid i-carotene. All-fra/w-fi-carolene (T) is the most important provitamin A carotenoid, which can be converted to all-fraws-retinal and then all-tram-retinol (If), which by definition is vitamin A. All-tram-retinol can be esterified with long-chain fatty acids to form retinyl ester (III), the storage form of vitaminA in the body.The active form of vitamin A in vision is 11-cts-retinal (TV).The transcriptionally active forms of vitaminA are all-tram-retinoic acid (V) and 9-cts-retinoic acid (VI). 13-cA-Retinoic acid (VII) has poor transcriptional regulatory activity but is used clinically as isotretinoin to treat skin diseases.

The MDR reversing action of carotenoids depended on the chemical structure of the carotenoids tested on the different cell lines. The different sensitivity of cancer cells to various carotenoids could be explained by the differences in their membrane passing properties or electronic distribution (semiconductor properties of the carotenoids). 

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