Diapolycopenedioic Acid Xylosyl Esters A, B, and C, Novel Antioxidative Glyco-C30-carotenoic Acids Produced by a New Marine Bacterium Rubritalea squalenifaciens

Shindo, Kazutoshi; Asagi, Emiko; Sano, Aya; Hotta, Eri; Minemura, Noriko; Mikami, Kanae; Tamesada, Emiko; Misawa, Norihiko; Maoka, Takashi

doi:10.1038/ja.2008.28

Cited by 53 publications

(27 citation statements)

References 16 publications

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“…[7][8][9] These studies have reported the isolation of rare carotenoids, (3R)-saproxanthin and myxol, from Flavobacteriaceae, 7 and novel glyco-C 30 carotenoids (diapolycopenedioic acid xylosyl esters A, B, and C from Rubritalea squalenifaciens 8 and methyl glucosyl-3,4-dehydroapo-8¢-lycopenoate from Planococcus maritimus 9 ).…”

Section: Introductionmentioning

confidence: 99%

Hydroxy-3,4-dehydro-apo-8′-lycopene and methyl hydroxy-3,4-dehydro-apo-8′-lycopenoate, novel C30 carotenoids produced by a mutant of marine bacterium Halobacillus halophilus

et al. 2010

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We performed the chemical mutagenesis of Halobacillus halophilus (the producer of a C 30 carotenoid, methyl glucosyl-3,4-dehydro-apo-8¢-lycopenoate) to isolate novel carotenoids that are biosynthetic intermediates of methyl glucosyl-3,4-dehydroapo-8¢-lycopenoate. As a result, we isolated two novel C 30 carotenoids, hydroxy-3,4-dehydro-apo-8¢-lycopene and methyl hydroxy-3,4-dehydro-apo-8¢-lycopenoate, which were biosynthesized through a novel 8¢-apo C 30 pathway. These carotenoids showed antioxidative activity in the 1 O 2 suppression model.

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Section: Introductionmentioning

confidence: 99%

Hydroxy-3,4-dehydro-apo-8′-lycopene and methyl hydroxy-3,4-dehydro-apo-8′-lycopenoate, novel C30 carotenoids produced by a mutant of marine bacterium Halobacillus halophilus

et al. 2010

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“…Recently we have performed the analysis of novel or rare types of carotenoids from new colored marine bacteria, which were classified to belong to a new species by the 16S rRNA analyses [7,8]. These studies have reported the isolation of rare carotenoids, (3R)-saproxanthin and myxol, from Flavobacteriaceae [7], and novel carotenoids glyco-C 30 -carotenoic acids (diapolycopenedioic acid xylosyl esters A, B, and C) from Rubritalea squalenifaciens [8].…”

Section: Introductionmentioning

confidence: 99%

“…These studies have reported the isolation of rare carotenoids, (3R)-saproxanthin and myxol, from Flavobacteriaceae [7], and novel carotenoids glyco-C 30 -carotenoic acids (diapolycopenedioic acid xylosyl esters A, B, and C) from Rubritalea squalenifaciens [8]. This time, we have found a novel carotenoioic acid ester produced by a marine bacterium Planococcus maritimus, and describe its structural determination (including the absolute configurations) as methyl glucosyl-3,4-dehydroapo-8'-lycopenoate, its antioxidative activity included.…”

Section: Introductionmentioning

confidence: 99%

Methyl Glucosyl-3,4-dehydro-apo-8′-lycopenoate, a Novel Antioxidative Glyco-C30-carotenoic Acid Produced by a Marine Bacterium Planococcus maritimus

et al. 2008

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Planococcus maritimus strain iso-3 was isolated from an intertidal sediment sample from the Clyde estuary in the UK. A novel red pigment glyco-carotenoic acid ester, methyl glucosyl-3,4-dehydro-apo-8Ј-lycopenoate has been isolated from this marine bacterium using chromatographic methods. The structure of methyl glucosyl-3,4-dehydro-apo-8Ј-lycopenoate was determined to be methyl 1-(b -D-glucopyranosyloxy)-3,4-didehydro-1,2-dihydro-8Ј-apo-y -caroten-8Ј-oate by the degradation experiment and the spectroscopic analyses. The methyl glucosyl-3,4-dehydro-apo-8Ј-lycopenoate showed potent antioxidative activity in the 1 O 2 suppression model.

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“…), Rubritella squalenifaciens (Shindo et al . ,, ), Planococcus maritimus (Shindo et al . ) and Halobacillus halophilus (Köcher et al .…”

Section: Introductionmentioning

confidence: 99%

Biosynthesis of a novel C30 carotenoid in Bacillus firmus isolates

et al. 2012

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Aims Pigmented Bacillus spp. with probiotic properties have been isolated. In the yellow‐/orange‐coloured strains, the carotenoid pigments present have been characterized. In contrast, the carotenoids present in the Bacillus isolates coloured red await identification. The present article reports progress on the elucidation of the pigment biosynthetic pathway in these red‐pigmented Bacillus firmus strains. Methods and Results A combination of UV/Vis, chromatographic and mass spectrometry (MS) has revealed the properties of the predominant pigment and the end‐point carotenoid of the pathway to be methyl 4,4′‐diapolycopene‐dioate after transmethylation. The diglycosyl ester of 4,4′‐diapolycopene‐dioate persists in vivo prior to chemical treatment. Different mutants and inhibitor treatment were employed to establish the C30 biosynthesis pathway with all precursors and intermediates to 4,4′‐diapolycopene‐dioate detected, which include 4,4′‐diapophytene and all desaturation intermediates to 4,4′‐diapolycopene and 4,4′‐diapolycopene‐dialdehyde. To cultures synthesizing the 4,4′‐diapolycopene‐dioate derivative and those in which its formation was inhibited, oxidative stress was induced by peroxide treatment. Conditions that decreased the growth rate of the pigmented cells by only 30% caused a complete growth inhibition of the culture devoid of the 4,4′‐diapolycopene‐dioate derivative. Conclusion This finding demonstrates the diversity of C30 carotenoid biosynthesis in Bacillus species and the antioxidative function of the 4,4′‐diapolycopene‐dioate derivative in B. firmus cells. Significance and Impact of the Study It could be shown that the C30 4,4′‐diapolycopene‐dioate derivatives protect pigmented B. firmus from peroxidative reactions. Under oxidative conditions, this can be an ecological advantage over nonpigmented (=noncarotenogenic) strains that are equally abundant.

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Diapolycopenedioic Acid Xylosyl Esters A, B, and C, Novel Antioxidative Glyco-C30-carotenoic Acids Produced by a New Marine Bacterium Rubritalea squalenifaciens

Cited by 53 publications

References 16 publications

Hydroxy-3,4-dehydro-apo-8′-lycopene and methyl hydroxy-3,4-dehydro-apo-8′-lycopenoate, novel C30 carotenoids produced by a mutant of marine bacterium Halobacillus halophilus

Hydroxy-3,4-dehydro-apo-8′-lycopene and methyl hydroxy-3,4-dehydro-apo-8′-lycopenoate, novel C30 carotenoids produced by a mutant of marine bacterium Halobacillus halophilus

Methyl Glucosyl-3,4-dehydro-apo-8′-lycopenoate, a Novel Antioxidative Glyco-C30-carotenoic Acid Produced by a Marine Bacterium Planococcus maritimus

Biosynthesis of a novel C30 carotenoid in Bacillus firmus isolates

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