Environmental Science and Pollution Research

, Volume 23, Issue 12, pp 11998–12006 | Cite as

Characteristic oxidation behavior of β-cyclocitral from the cyanobacterium Microcystis

  • Koji TomitaEmail author
  • Masateru Hasegawa
  • Suzue Arii
  • Kiyomi Tsuji
  • Beata Bober
  • Ken-ichi Harada
Research Article


The cyanobacterium Microcystis produces volatile organic compounds such as β-cyclocitral and 3-methyl-1-butanol. The lysis of cyanobacteria involving the blue color formation has been occasionally observed in a natural environment. In this study, we focused on the oxidation behavior of β-cyclocitral that contributed to the blue color formation in a natural environment and compared β-cyclocitral with a structurally related compound concerning its oxidation, acidification, and lytic behavior. The oxidation products of β-cyclocitral were identified by the addition of β-cyclocitral in water, in which 2,2,6-trimethylcyclohex-1-ene-1-yl formate and 2,2,6-trimethylcyclohexanone were structurally characterized. That is, β-cyclocitral was easily oxidized to produce the corresponding carboxylic acid and the enol ester in water without an oxidizing reagent, suggesting that this oxidation proceeded according to the Baeyer-Villiger oxidation. The oxidation behavior of β-cyclocitral in a laboratory was different from that in the natural environment, in which 2,2,6- trimethylcyclohexanone was detected at the highest amount in the natural environment, whereas the highest amount in the laboratory was β-cyclocitric acid. A comparison of β-cyclocitral with structurally similar aldehydes concerning the lytic behavior of a Microcystis strain and the acidification process indicated that only β-cyclocitral was easily oxidized. Furthermore, it was found that a blue color formation occurred between pH 5.5 and 6.5, suggesting that chlorophyll a and β-carotene are unstable and decomposed, whereas phycocyanin was stable to some extent in this range. The obtained results of the characteristic oxidation behavior of β-cyclocitral would contribute to a better understanding of the cyanobacterial life cycle.


β-cyclocitral Oxidation Acidification Cyanobacteria Blue color formation Lysis 



We acknowledge Drs. Atsushi Miyachi and Andrea Roxanne J. Anas and Mr. Kohei Kawai for measurement of the high-resolution mass spectral data, NMR measurement, and technical assistance, respectively, in this study.

Supplementary material

11356_2016_6369_MOESM1_ESM.pdf (617 kb)
ESM 1 (PDF 617 kb)


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Copyright information

© Springer-Verlag Berlin Heidelberg 2016

Authors and Affiliations

  • Koji Tomita
    • 1
    • 2
    Email author
  • Masateru Hasegawa
    • 2
  • Suzue Arii
    • 2
  • Kiyomi Tsuji
    • 3
  • Beata Bober
    • 2
    • 4
  • Ken-ichi Harada
    • 2
  1. 1.Aichi Prefectural Institute of Public HealthNagoyaJapan
  2. 2.Graduate School of Environmental and Human Science and Faculty of PharmacyMeijo UniversityNagoyaJapan
  3. 3.Kanagawa Prefectural Institute of Public HealthChigasakiJapan
  4. 4.Department of Plant Physiology and DevelopmentJagiellonian UniversityKrakowPoland

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