Lists of Natural Carotenoids

Straub, Otto

doi:10.1007/978-3-0348-5831-1_12

Cited by 19 publications

(7 citation statements)

References 669 publications

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“…A variety of authentic carotenoid pigments were obtained from commercial sources or were isolated from well-documented natural sources, as follows (see Straub, 1971 for structures; see also Appendix A for certain structures designated by roman numerals): 0-carotene (XXII; /3,/3-carotene) was purchased from Carl Roth Laboratories, West Germany; echinenone (XXVIII; j3,0-caroten-4-one) and canthaxanthin (XXIX; /3,/3-carotene-4,4'-dione) were the generous gifts of F. Hoffman-LaRoche, Basel, Switzerland; isocryptoxanthin (XXX; j3,/3-caroten-4-ol) and isozeaxanthin (jß,/3-carotene-4,4'-diol) were prepared by the borohydride reduction of echinenone and canthaxanthin, respectively; lutein (^.L-carotene-S, 3'-diol) and violaxanthin (zeaxanthin diepoxide; 5,6,5',6'-diepoxy-5,6,5',6'-tetrahydro-ß.ß-carotene-3,3'-diol) were isolated from common spinach (Spinacea oleracea); and trans-and cis-fucoxanthin (XXXV;5,3',6,7,8,5',6'-hexa-hydro-jS,|3-caroten-8-one-3'-acetate) were isolated from the brown alga Sargassum sp., obtained locally.…”

Section: Methodsmentioning

confidence: 99%

Geochemistry of Tetrapyrrole, Tetraterpenoid, and Perylene Pigments in Sediments from the Gulf of California: Deep Sea Drilling Project Leg 64, Sites 474, 477, 479, and 481, and Scripps Institution of Oceanography Guaymas Basin Survey Cruise Leg 3, Sites 10G and 18G

Baker¹,

Louda²

1982

Initial Reports of the Deep Sea Drilling Project

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Results and discussion cover pigment analyses of 36 sediment samples recovered by Deep Sea Drilling Project Leg 64, and six samples from the Leg 64 site-survey cruise in the Guaymas Basin (Scripps Institution of Oceanography, Leg 3). Pigments investigated were tetrapyrroles, tetraterpenoids, and the PAH compound perylene.Traces of mixed nickel and copper ETIO-porphyrins were ubiquitous in all sediment samples, except for the very surface (i.e., <2 m sub-bottom), and their presence is taken as an indication of minor influxes of previously oxidized allochthonous (terrestrial) organic matter.Phorbides and chlorins isolated from Site 479 sediment samples (i.e., the oxygen-minimum locale, northeast of the Guaymas Basin) well represent the reductive diagenesis ("Treibs Scheme"; see Treibs, 1936) of chlorophyll derivatives. Three forms of pheophytin-a, plus a variety of phorbides, were found to give rise to freebase porphyrins, nickel phylloerythrin, and nickel porphyrins, with increasing depth of burial (increasing temperature).Sediments from Sites 481, 10G, and 18G yielded chlorophyll derivatives characteristic of early oxidative alterations. Included among these pigments are allomerized pheophytin-a, purpurin-18, and chlorin-p 6 .The high thermal gradient imposed upon the late Quaternary sediments of Site 477 greatly accelerated chlorophyll diagenesis in the adjacent overlying sediments, that is, the production of large quantities of free-base desoxophylloerythroetioporphyrin (DPEP) occurred in a section (477-7-5) presently only 49.8 meters sub-bottom. Present depth and age of these sediments are such that only chlorins and phorbides would be expected.Carotenoid (i.e., tetraterpenoids) concentrations were found to decrease rapidly with increasing sub-bottom depth. Less deeply buried sediments (e.g., 0-30 m) yielded mixtures of carotenes and oxygen-substituted carotenoids. Oxygencontaining (oxy-, oxo-, epoxy-) carotenoids were found to be lost preferentially with increased depth of burial.Early carotenoid diagenesis is suggested as involving interacting reductions and dehydrations whereby dehydro-, didehydro-, and retro-carotenes are generated. Destruction of carotenoids as pigments may involve oxidative cleavage of the isoprenoid chain through epoxy intermediates, akin to changes in the senescent cells of plants.Perylene was found to be a common component of the extractable organic matter from all sediments investigated. The generation of alkyl perylenes was found to parallel increases in the existing thermal regime at all sites. Igneous sills and sill complexes within the sediment profile of Site 481 altered (i.e., scrambled) the otherwise straightforward thermally induced alkylation of perylene.The degree of perylene alkylation is proposed as an indicator of geothermal stress for non-contemporaneous marine sediments.

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Section: Methodsmentioning

confidence: 99%

Geochemistry of Tetrapyrrole, Tetraterpenoid, and Perylene Pigments in Sediments from the Gulf of California: Deep Sea Drilling Project Leg 64, Sites 474, 477, 479, and 481, and Scripps Institution of Oceanography Guaymas Basin Survey Cruise Leg 3, Sites 10G and 18G

Baker¹,

Louda²

1982

Initial Reports of the Deep Sea Drilling Project

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“…Lycopene (ψ,ψ-carotene), one of more than 600 carotenoids synthesized by plants and photosynthetic microorganisms [1], is a tetraterpene hydrocarbon containing 40 carbon atoms and 56 hydrogen atoms with a molecular mass of 536 (see structure in Figure 1) [2]. Lycopene is a lipophilic hydrocarbon that is soluble in chloroform, benzene and ether and practically insoluble in methanol, ethanol and water.…”

Section: Chemistry Of Lycopenementioning

confidence: 99%

Multitargeted therapy of cancer by lycopene

2008

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An acyclic, non-provitamin A carotene, lycopene is responsible for the red pigmentation of ripe tomatoes and some other edible fruits such as watermelon and papaya. Lycopene is also a potent antioxidant and scavenger of free radicals. Multiple retrospective and prospective epidemiological studies have indicated that the consumption of tomato products containing lycopene is associated with a reduced risk of prostate cancer. These epidemiological studies are supported by numerous in vitro assays using cell cultures that show anti-cancer activities and cancer chemoprevention activities of lycopene in many cell lines including prostate cancer cells. These activities include inducing apoptosis, inhibiting metastasis, preventing oxidative stress, and up-regulating the antioxidant response element so that cells can produce cytoprotective enzymes against prooxidants and electrophiles. In vivo animal studies and Phase I and II clinical trials have shown that lycopene supplements are non-toxic and that lycopene is orally bioavailable. Furthermore, lycopene is concentrated in prostate tissue and localized to the nucleus. In addition, some oxygenated metabolites of lycopene have been identified, and might be active as chemoprevention agents. The next phase of research concerning lycopene as a chemoprevention agent will be Phase II clinical trials of efficacy that are placebo-controlled, randomized and double blind. These clinical trials are required to establish the efficacy of lycopene supplementation.

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“…Thus, phytoene had Amax (petroleum ether) at 275, 285, (3,13) and ME at m/e 540 (72%, C,0H,H) with a major fragment ion at mle 403 (12%, M-137; metastable at nm/e 301, 4032/540 = 300.8) reflecting cleavage of the bisallylic bonds at C-7, 8 and C-7', 8' adjacent to the main chromophore (13,14). This Photostimulation of carotenogenesis has been reported in both photosynthetic and nonphotosynthetic organisms including Euglena (1,5,7,9).…”

Section: Resultsmentioning

confidence: 99%

“…Therefore, we selected for experimentation the photosynthetic wild type E. gracilis Z and the nonphotosynthetic mutants PR-1, -2, and -3 (8) and PR-4, all of which were derived from the wild type after being subjected to high hydrostatic pressure. The carotenes of these organisms were isolated chromatographically and identified from RF values (2), co-chromatography with authentic samples, absorption spectra (3), and mass spectra (13,14). MATERIALS Pigment Extraction.…”

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confidence: 99%