Mass Spectrometric Studies of Carotenoids. 2. A Survey of Fragmentation Reactions.

Enzell, Curt R.; Francis, George W.; Liaaen‐Jensen, S.; Schultes, Richard Evans; Lindberg, Alf A.; Jansen, Gert; Lamm, Bo; Samuelsson, Benny

doi:10.3891/acta.chem.scand.23-0727

Cited by 121 publications

(50 citation statements)

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“…4A). This type of fragmentation had been previously observed [8,18]. By the same token, the two ion peaks m/z 742 and m/z 509 detected in the spectrum of the deoxymyxoxanthophyll spectrum (Fig.…”

Section: Nature Of the Myxoxanthophyll-like Compound In The Acrtr Strainmentioning

confidence: 63%

The zeaxanthin biosynthesis enzyme ²‐carotene hydroxylase is involvedin myxoxanthophyll synthesis in Synechocystis sp. PCC 6803

Lagarde

Vermaas

1999

FEBS Letters

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Section: Nature Of the Myxoxanthophyll-like Compound In The Acrtr Strainmentioning

confidence: 63%

The zeaxanthin biosynthesis enzyme ²‐carotene hydroxylase is involvedin myxoxanthophyll synthesis in Synechocystis sp. PCC 6803

Lagarde

Vermaas

1999

FEBS Letters

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“…By comparing the fragmentation patterns of compounds 3 and 4 from LC-MS, MS-MS (1,8), and NMR spectroscopic analyses, we propose that the five CDBs extend from the penultimate isoprenoid unit of the octaprenyl tail of compounds 1 and 2 (structures 1 and 2) as shown in Fig. 2.…”

Section: In Vivo Activity Of Carotenoid Desaturase Enzymes On Uqsmentioning

confidence: 99%

“…S1 in the supplemental material). In comparison with fragmentation patterns of carotenoid compounds (1,8), we propose that compound 17 is a 10-CDB-containing 2-pentaprenylphenol derivative (structure 17 is shown in Fig. 2).…”

Section: In Vivo Activity Of Carotenoid Desaturase Enzymes On Uqsmentioning

confidence: 99%

Biosynthesis of Ubiquinone Compounds with Conjugated Prenyl Side Chains

Lee

Salomon

Mijts

et al. 2008

Appl Environ Microbiol

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Enzymatic steps from two different biosynthetic pathways were combined in Escherichia coli, directing the synthesis of a new class of biomolecules-ubiquinones with prenyl side chains containing conjugated double bonds. This was achieved by the activity of a C 30 carotenoid desaturase, CrtN, from Staphylococcus aureus, which exhibited an inherent flexibility in substrate recognition compared to other carotenoid desaturases. By utilizing the known plasticity of E. coli's native ubiquinone biosynthesis pathway and the unusual activity of CrtN, modified ubiquinone structures with prenyl side chains containing conjugated double bonds were generated. The side chains of the new structures were confirmed to have different degrees of desaturation by mass spectrometry and nuclear magnetic resonance analysis. In vivo 14 C labeling and in vitro activity studies showed that CrtN desaturates octaprenyl diphosphates but not the ubiquinone compounds directly. Antioxidant properties of conjugated side chain ubiquinones were analyzed in an in vitro ␤-carotene-linoleate model system and were found to be higher than the corresponding unmodified ubiquinones. These results demonstrate that by combining pathway steps from different branches of biosynthetic networks, classes of compounds not observed in nature can be synthesized and structural motifs that are functionally important can be combined or enhanced.

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“…2; the shape of the spectrum was similar to that of spheroidenone (Takaichi et al, 1991). Furthermore, this carotenoid was identified as spheroidenone by comparing the mass spectra with those given in the literature (Enzell et al, 1969). The mass spectra of this carotenoid obtained in the positive ion mode (Table 1) Fig.…”

Section: Structure Elucidation Of Major Carotenoidsmentioning

confidence: 91%

Identification and antioxidant activity of carotenoids from superfine powder of Rhodobacter sphaeroides

Kong

Bo-di

et al. 2017

Emir J Food Agric

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The interest in carotenoids from the natural-antioxidant point of view has recently risen sharply because of their substantial health benefits. Here, we report the identification and antioxidant activity of carotenoids extracted by superfine grinding from Rhodobacter sphaeroides 3757 which is a species of photosynthetic bacteria. After separation and purification by silica gel column chromatography and reversed-phase high performance liquid chromatography (RP-HPLC), the four major carotenoids from the superfine powder of R. sphaeroide 3757 were identified as bixin, hydroxyspheroidenone, 3,3¢,4¢-tetrahydrospirilloxanthin-20-al, and spheroidenone by reversed phase - high performance liquid chromatography - atmospheric pressure chemical ionization - mass spectrometry (RP-HPLC-APCI-MS). The antioxidant activity of the carotenoids extracted after superfine grinding of dry biomass of R. sphaeroide 3757 was higher than that after ultrasonic treatment. When the ratio solvent-to-solid was 30, 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical-scavenging activity, reducing power, and lipid peroxidation inhibitory activity of the extracts after superfine grinding were 74.0% ± 3.1%, 0.497 ± 0.022, and 77.6% ± 3.2%, respectively. By contrast, the extracts after ultrasonic treatment, these numbers were 61.0% ± 2.5%, 0.328 ± 0.014, and 55.2% ± 2.3%, respectively. These results indicate that carotenoids from R. sphaeroide 3757 show a significant antioxidant activity in vitro in a concentration-dependent manner, and that superfine grinding is the optimal extraction method. We hope to provide scientific guidance for commercial production of natural- antioxidant and functional food from carotenoids of R. sphaeroide.

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Mass Spectrometric Studies of Carotenoids. 2. A Survey of Fragmentation Reactions.

Cited by 121 publications

References 0 publications

The zeaxanthin biosynthesis enzyme ²‐carotene hydroxylase is involvedin myxoxanthophyll synthesis in Synechocystis sp. PCC 6803

The zeaxanthin biosynthesis enzyme ²‐carotene hydroxylase is involvedin myxoxanthophyll synthesis in Synechocystis sp. PCC 6803

Biosynthesis of Ubiquinone Compounds with Conjugated Prenyl Side Chains

Identification and antioxidant activity of carotenoids from superfine powder of Rhodobacter sphaeroides

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