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Applied Microbiology and Biotechnology

, Volume 97, Issue 19, pp 8479–8486 | Cite as

3-β-Glucosyl-3′-β-quinovosyl zeaxanthin, a novel carotenoid glycoside synthesized by Escherichia coli cells expressing the Pantoea ananatis carotenoid biosynthesis gene cluster

  • Seon-Kang Choi
  • Ayako Osawa
  • Takashi Maoka
  • Jun-ichiro Hattan
  • Kei Ito
  • Ai Uchiyama
  • Mai Suzuki
  • Kazutoshi Shindo
  • Norihiko MisawaEmail author
Biotechnological products and process engineering

Abstract

Escherichia coli cells that express the full six carotenoid biosynthesis genes (crtE, crtB, crtI, crtY, crtZ, and crtX) of the bacterium Pantoea ananatis have been shown to biosynthesize zeaxanthin 3,3′-β-d-diglucoside. We found that this recombinant E. coli also produced a novel carotenoid glycoside that contained a rare carbohydrate moiety, quinovose (chinovose; 6-deoxy-d-glucose), which was identified as 3-β-glucosyl-3′-β-quinovosyl zeaxanthin by chromatographic and spectroscopic analyses. The chirality of the aglycone of these zeaxanthin glycosides had been shown to be 3R,3′R, in which the hydroxyl groups were formed with the CrtZ enzyme. It was here demonstrated that zeaxanthin synthesized from β-carotene with CrtR or CYP175A1, the other hydroxylase with similar catalytic function to CrtZ, possessed the same stereochemistry. It was also suggested that the singlet oxygen-quenching activity of zeaxanthin 3,3′-β-d-diglucoside, which has a chemical structure close to the new carotenoid glycoside, was superior to that of zeaxanthin.

Keywords

Pantoea ananatis 3-Glucosyl-3′-quinovosyl zeaxanthin crtX crtR CYP175A1 

Notes

Acknowledgments

The authors are grateful to the Marine Biotechnology Institute (MBI), Kamaishi-shi, Iwate, Japan (closed on June 30, 2008), since this work was initially in part performed here. S.K.C. thanks Mr. Satoru Matsuda of MBI for HPLC analyses.

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Copyright information

© Springer-Verlag Berlin Heidelberg 2013

Authors and Affiliations

  • Seon-Kang Choi
    • 1
  • Ayako Osawa
    • 2
  • Takashi Maoka
    • 3
  • Jun-ichiro Hattan
    • 4
  • Kei Ito
    • 2
  • Ai Uchiyama
    • 2
  • Mai Suzuki
    • 2
  • Kazutoshi Shindo
    • 2
  • Norihiko Misawa
    • 4
    Email author
  1. 1.Tongyang Life Science CorpSeoulSouth Korea
  2. 2.Department of Food and NutritionJapan Women’s UniversityTokyoJapan
  3. 3.Research Institute for Production DevelopmentKyotoJapan
  4. 4.Research Institute for Bioresources and BiotechnologyIshikawa Prefectural UniversityIshikawaJapan

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