Capsanthin

Capsorubin (3,3 -dibydroxy-K,K-carotene-6,6 dione) [470-38-2] M 604.9, m 218", X.max 468, 503 nm, in bexane. Possible impurities zeaxanthin and capsanthin. Purified by chromatography on a column of CaC03 or MgO. Crystd from benzene/pet ether or CS2. 

Food (3-Carotene a-Carotene Lutein Lycopene (3-Cryptoxantlun Zeaxanthin Capsanthin ... 

Capsicum annuum fruit Capsanthin, capsorubin (paprika) Food colouring... 

Carotenoids are also present in animal products such as eggs, lobsters, greyflsh, and various types of hsh. In higher plants, they occur in photosynthetic tissues and choloroplasts where their color is masked by that of the more predominant green chlorophyll. The best known are P-carotene and lycopene but others are also used as food colorants a-carotene, y-carotene, bixin, norbixin, capsanthin, lycopene, and P-apo-8 -carotenal, the ethyl ester of P-apo-8-carotenic acid. These are Upid-soluble compounds, but the chemical industry manufactures water-dispersible preparations by formulating coUoid suspensions by emulsifying the carotenoids or by dispersing them in appropriate colloids. ... 

Most of this amount is in the form of fucoxanthin in various algae and in the three main carotenoids of green leaves lutein, violaxanthin, and neoxanthin. Others produced in much smaller amounts but found widely are p-carotene and zeaxanthin. The other pigments found in certain plants are lycopene and capsanthin (Figure 2.2.1). Colorant preparations have been made from all of these compounds and obviously the composition of a colorant extract reflects the profile of the starting material. Carotenoids are probably the best known of the food colorants derived from natural sources. ... 

Thonsands of paprika varieties belong to the Capsicum genns and they vary widely in their sizes, shapes, colors, flavors, and pungency levels. The major carotenoids fonnd in red paprika are capsanthin and capsornbin, which posses k end gronp. Yellow pigments such as lutein, zeaxanthin, violaxanthin, and 3-carotene... 

FIGURE 4.2.2 Structures of carotenoids found in paprika (capsanthin and capsombin), saffron and gardenia (crocetin derivatives), and annatto (bixin and norbixin). 

Lutein, zeaxanthin, and capsanthin/capsorubin from marigold, wolfberry, and red pepper, respectively... 

FIGURE 5.3.3B Oxidation to ketocarotenoids, capsorubin, and capsanthin. Enzyme abbreviations and enzyme activities are defined in Table 5.3.1. 

Physiologically, violaxanthin is an important component of the xanthophyU cycle a high light stress-induced de-epoxidation of the violaxanthin pool to the more photoprotective zeaxanthin is mediated by violaxanthin de-epoxidase (VDE). Violaxanthin and neoxanthin, an enzymatically (NXS)-produced structural isomer, are the precursors for the abscisic acid (ABA) biosynthetic pathway (Figure 5.3.1, Pathway 4 and Figure 5.3.2). In non-photosynthetic tissues, namely ripe bell peppers, antheraxanthin and violaxanthin are precursors to the red pigments, capsanthin and capsorubin, respectively (Figure 5.3.3B). 

Astaxanthin, capsanthin, lutein, zeaxanthin, canthaxanthin, P-cryptoxanthin, echinenone, 15-cis-P-carotene, 13-cis- P-carotene, a-carotene, all-ircms P-carotene, 9-cis-P-carotene, 5-carotene, lycopene... 

Traditionally, carotenoid standards are prepared in each laboratory using the best sources of each individual carotenoid, for example, violaxanthin from spinach, antheraxanthin from potatoes, capsanthin and capsorubin from paprika, a- and P-carotene from carrots, and lycopene from tomatoes. 

Bikadi Z, Zsila F, Deli J, Mady G, and Simonyi M. 2002. The supramolecular structure of self-assembly formed by capsanthin derivatives. Enantiomer 7 67-76. 

Figure 73. The carotenoid biosynthetic pathway. Enzymes are named according to the designation of their genes Ccs, capsanthin-capsorubin synthase CrtL-b, lycopene-b-cyclase CrtL-e, lycopene-e-cyclase CrtR-b, b-ring hydroxylase, CrtR-e, e-ring hydroxylase DMADP, dimethylallyl diphosphate GGDP, geranylgeranyl diphosphate Ggps, geranylgeranyl-diphosphate synthase IDP, isopentenyl diphosphate Ipi, IDP isomerase Pds, phytoene desaturase Psy, phytoene synthase Vde, violaxanthin de-epoxidase Zds, z-carotene desaturase Zep, zeaxanthin epoxidase. (From van den Berg and others 2000.)...

Caprylic/capric triglyceride, cosmetically useful lipid, 7 833t Capsanthin, 24 560 Capsicum group, 23 164-165 Capsorubin, 24 560 Capsular polysaccharides, 20 455 Capsules. See also Microencapsulation extruding, 16 446 pharmaceutical, 18 708 produced by spray drying, 16 447-448 Capsule standard platinum resistance thermometers, 24 445 Captafol, 23 629, 647 Captan, 23 628 Captiva camera, 19 307 Captive hydrogen, 13 841 Captopril, 5 148... 

Paprika contains capsombin and capsanthin (Fig. 8.3) which occur mainly as the lauric acid esters, and about 20 other carotenoid pigments. Paprika is produced in many countries which have developed their own specialties. Cayenne or cayenne pepper, produced from a different cultivar of C. annum, is usually more pungent. C. frutescens is the source of the very pungent Tabasco sauce. Paprika oleoresin is produced by solvent extraction of the ground powder. Obviously paprika supplies both flavor and color and its use is limited to those products compatible with the flavor. The recent rise in demand for tomato products in the form of pizza, salsa, etc., has increased the demand for paprika. Paprika is used in meat products, soups, sauces, salad dressings, processed cheese, snacks, confectionery and baked goods.1018... 

Pigments were separated on a normal (150 X 4 mm i.d., particle size 5 /tin) and on a microbore ODS column (150 X 2 mm i.d., particle size 4 jttm) using gradient elution. The steps of gradient elution are shown in Table 2.7. Carotenoids were detected at 440 nm. Columns were not thermostated and separations were performed at room temperature (20 2°C). The mean and the relative standard deviation of retention time and peak area were computed from three parallel measurements. The carotenoids capsanthin, zeaxanthin and j0-carotenein and the extracts were tentatively identified comparing their retention time with those of authentic standards. 

Fig. 2.3. Characteristic chromatogram of paprika paste. Detection at 450 nm. Peak identification 1 = Capsorubin 2 = 5,6-Diepikarpoxanthin 3 = Capsanthin-5,6-epoxide 4 = Capsanthin-3,6-epox-ide 5 = Violaxanthin 6 = Luteoxanthin 2 7 = Luteoxanthin 1 8 = Capsanthin 9 = Antheraxanthin 10 = Mutatoxanthin 11 = Cucurbitaxanthin A 12 = (9/9 Z)-Capsanthins 13 = (13/13 Z)-Capsanthins 14 = Zeaxanthin 15 = Nigroxanthin 16 = (9Z)-Zeaxanthin 17 = (13Z)-Zeaxanthin 18 = Cryptocapsin 19 = a-Cryptoxanthin 20 = /TCryptoxanthin 21 = (Z)-Cryptoxanthin 22 = /1-Carotene 23 = (Z)-jS-Carotene. Reprinted with permission from J. Deli et al. [27].

Fig. 2.8. Reversed-phase HPLC chromatograms (430 nm) of colour pigments of paprika powder after 56 days of storage time, a = control, b = 5 per cent GLT, c = 5 per cent HP-/3-CD. Peak indentification 1 = capsanthin 2 = zeaxanthin 3 = /3-carotene. Reprinted with permission from T. Cserhati el al. [32].

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