Capsorubin

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. 

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

Fruits are yet more prodigious than flowers in their synthetic abilities. More than 70 characteristic carotenoids have been described and classified as those with minimal quantities, higher quantities, and specific carotenoids, for example, capsan-thin and capsorubin in pepper fruits. 

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). 

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. 

Capsandiin, capsorubin, paprika, paprika E 160c Paprika (Capsicum annum L) reddish (carmine) orange 0... 

FIGURE 3.9 Number of capsorubin (3.48) molecules in small oligomers. Reaching a decamer, the absorbance converts to a constant value. (From Mayer, B., Diisseldorf, unpublished.)... 

Devasagayam, T.P.A., Werner, T., Ippendorf, H., Martin H.-D., and Sies, H. 1992. Synthetic carotenoids, novel polyene polyketones and new capsorubin isomers as efficient quenchers of singlet molecular oxygen. 

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... 

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. 2.9. Separation of carotenoid pigments by reversed-phase (I) and normal-phase (II) HPLC. The relative areas of carotenoids (retention time) are shown for latoxanthin (9.7), capsorubin (11.4), neoxanthin...

Fig. 2.26. Reversed-phase HPLC separation of (a) Sobrasada sausage extract and (b) saponified Sobrasade sausage extact in an ODS column at maximum absorbances at each point in time. Peak identification 1 - 2, 4 - 6, 8, 12, 14-17 = unidentified free 3 = capsorubin 7 = violaxanthin 9 = capsanthin 10 = anteraxanthin 11 = cw-capsanthin 13 = lutein and zeaxanthin 18 = cantaxanthin, internal standard 19 = cryptoxanthin 20, 24, 25, 28 = unidentified monoester 21 = /J-cryptoxanthin 22 = capsorubin monoester 23, 26, 27, 29 = capsanthin monoester 30, 31 = lutein-zeaxanthin monoester 32 = /1-carotene 33 = cis-f)-carotene 34, 37, 39, 41, 43 = capsanthin diester 35 = capsorubin diester 36, 38, 40, 42, 44 = unidentified diester. Reprinted with permission from J. Oliver et al. [56],...

Pigments capsorubin Flavors linalool, 3-carene, 2,3-butanedione Placenta. capsaicinoids... 

Fig. 8.2 Carotene and xanthophyll biosynthetic pathways in Capsicum. Isopentenyl pyrophosphate (IPP) phytoene synthase (PSY) lycopene fi-cyclase (LCYB) lycopene e-cyclase (LCYE) P-carotene hydroxylase (CrtZ-2) zeaxanthin epoxidase (Ze) and capsanthin-capsorubin synthase (CCS)...

Fig. 8.3 UPLC analysis of Cupi/cMm-lyoplrilizEd pericarp carotenoids. Carotenoids detected by absorption at 454 nm, following separation on a waters acquity C18 1.8 xm HSS particle, 2.1 x 100 mm column resolved with 10% isopropanol (v/v) (a) and 100% acetonitrile (b). The solvent profile included two linear phases (0-3 min at 75% (b) 3-11 min from 95 to 100%) flow rate of 0.75 mL/min. (a) Standards (each at 100 ppm) capsorubin (1.7 min), capsanthin (2.08 min), antherxanthm (2.69 min), zeaxanthin (2.97 min), f -cryptoxanthin (4.86 min), and P-carotene (8.15 min), (b) Valencia pericarp extract, (c) NuMex Sunset pericarp extract...

Lefebvre V, Kuntz M, Camara B, PaUoix A (1998) The capsanthin-capsorubin synthase gene a candidate gene for the y locus controlling the red fruit colour in pepper. Plant Mol Biol 36 785-789... 

Lang YQ, Yanagawa S, Sasanuma T, Sasakuma T (2004) Orange fruit color in Capsicum due to deletion of capsanthin-capsorubin synthesis gene. Breed Sci 54 33-39... 

Popovsky S, Paran I (2000) Molecular genetics of the y locus in pepper its relation to capsanthin-capsorubin synthase and to fruit color. Theor Appl Genet 101 86-89... 

Pathways for the biosynthesis of the cyclopentane carotenoids capsanthin [3,3 -dihydroxy- 8,K-caroten-6 -one (146)] and capsorubin [3,3 -dihydroxy-ir,K-caro-tene-6,6 -dione (147)] have been proposed from consideration of the carotenoids identified in extracts of lilies and red peppers. 

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