Isolation and Identification of 4, 4’-Diapolycopene-4,4’-dioic Acid Produced by Bacillus firmus GB1 and its Singlet Oxygen Quenching Activity

Ayako Osawa; Kanoko Iki; Gerhard Sandmann; Kazutoshi Shindo

doi:10.5650/jos.62.955

Chemistry and Organic Synthesis

Isolation and Identification of 4, 4’-Diapolycopene-4,4’-dioic Acid Produced by Bacillus firmus GB1 and its Singlet Oxygen Quenching Activity

Ayako Osawa, Kanoko Iki, Gerhard Sandmann, Kazutoshi Shindo

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Keywords: 4,4’-diapolycopene-4,4’-dioic acid, Bacillus firmus GB1, polystyrenic synthetic adsorbent, ¹O₂ quenching activity

JOURNAL FREE ACCESS

2013 Volume 62 Issue 11 Pages 955-960

DOI https://doi.org/10.5650/jos.62.955

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Abstract

We succeeded in purifying the carotenoid produced by Bacillus firmus GB1 using chromatography on polystyrenic synthetic adsorbents, and identified it as 4,4’-diapolycopene-4,4’-dioic acid by HRESI-MS and NMR analyses of it and its dimethylester. In addition, we clarified the singlet oxygen (¹O₂) quenching activities of 4,4’-diapolycopene-4,4’-dioic acid and its methyl esters (mono and dimethyl ester). Their IC₅₀ values were 5.8 μM, 6.0 μM, and 6.2 μM, respectively. To our knowledge, this is the first report concerning the isolation and antioxidative activity of 4,4’-diapolycopene-4,4’-dioic acid, a product of the C30 carotenoid biosynthesis pathway.

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