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Characteristic oxidation behavior of β-cyclocitral from the cyanobacterium Microcystis

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Abstract

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.

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References

  • Arii S, Tsuji K, Tomita K, Hasegawa M, Bober B, Harada K-I (2015) Blue color formation of cyanobacteria during lysis process under natural conditions. Appl Environ Microbiol 81(8):2667–2675

    Article  CAS  Google Scholar 

  • Chorus I, Bartram J (1999) Toxic cyanobacteria in water. E & FN Spon, London

    Book  Google Scholar 

  • Fallon RD, Brook TD (1979) Lytic organisms and photooxidative effects: influence on blue-green algae cyanobacteria in Lake Mendota. Wisconsin Appl Environ Microbiol 38(3):499–505

    CAS  Google Scholar 

  • Fujise D, Tsuji K, Fukusima N, Kawai K, Harada K-I (2010) Analytical aspects of cyanobacterial volatile organic compounds for investigation of their production behavior. J Chromatogr A 1217(39):6122–6125

    Article  CAS  Google Scholar 

  • Harada K-I, Tsuji K, Ohta A, Takayanagi K, Tamaki S, Suzuki T, Ito E, Fujii K (2007) Isolation of a lytic bacterium against cyanobacteria and its active compounds. J Res Inst Meijo Univ 6:17–28

    CAS  Google Scholar 

  • Harada K-I, Ozaki K, Tsuzuki S, Kato H, Hasegawa M, Kuroda EK, Arii S, Tsuji K (2009) Blue color formation of cyanobacteria with β-cyclocitral. J Chem Ecol 35(11):1295–1301

    Article  CAS  Google Scholar 

  • Hashimoto EH, Kato H, Kawasaki Y, Nozawa Y, Tsuji K, Hirooka EY, Harada K-I (2009) Further investigation of microbial degradation of microcystin using advanced Marfey’s Method. Chem Res Toxicol 22:391–398

    Article  CAS  Google Scholar 

  • Leisch H, Morley K, Lau PCK (2011) Baeyer-Villiger monooxygenase: more than just green chemistry. Chem Rev 111(7):4165–4222

    Article  CAS  Google Scholar 

  • Nozawa Y, Kawashima A, Hashimoto EH, Kato H, Harada K-I (2009) Application of log D for the prediction of hydrophobicity in advanced Marfey’s Method. J Chromatogr A 1216(18):3807–3811

    Article  CAS  Google Scholar 

  • Ozaki K, Ohta A, Iwata C, Horikawa A, Tsuji K, Ito E, Ikai Y, Harada K-I (2008) Lysis of cyanobacteria with volatile organic compounds. Chemosphere 71(8):1531–1538

    Article  CAS  Google Scholar 

  • Sigee DC (2005) Freshwater microbiology: biodiversity and dynamic interactions of microorganisms in aquatic environment. John Wiley and Sons, Inc., Chichester, UK

    Google Scholar 

  • Sigee DC, Glenn R, Andrews MJM, Bellinger EG, Butler RD, Epton HA, Hendry RD (1999) Biological control of cyanobacteria: principles and possibilities. Hydrobiologia 395–396:161–172

    Article  Google Scholar 

  • Uchida H, Kouchiwa T, Watanabe K, Kawasaki A, Hodoki Y, Ohtani I, Yamamoto Y, Suzuki M, Harada K-I (1998) A coupled assay system for the lysis of cyanobacteria. J Water Treat Biol 34(1):67–75

    Article  Google Scholar 

  • Watanabe MF, Harada K-I, Carmichael WW, Fujiki H (1996) Toxic microcystis. CRC Press, Boca Raton, FL

    Google Scholar 

  • Wu ZX, Gan NQ, Huang Q, Song LR (2006) Response of Microcystis to copper stress: do phenotypes of Microcystis make a difference in stress tolerance? Environ Pollu 147(2):324–330

    Article  Google Scholar 

Download references

Acknowledgments

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.

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Authors and Affiliations

  1. Aichi Prefectural Institute of Public Health, Tsujimachi, Kita, Nagoya, 462-8576, Japan

    Koji Tomita

  2. Graduate School of Environmental and Human Science and Faculty of Pharmacy, Meijo University, 150 Yagotoyama Tempaku, Nagoya, 468-8503, Japan

    Koji Tomita, Masateru Hasegawa, Suzue Arii, Beata Bober & Ken-ichi Harada

  3. Kanagawa Prefectural Institute of Public Health, Shimomachiya, Chigasaki, Kanagawa, 253-0087, Japan

    Kiyomi Tsuji

  4. Department of Plant Physiology and Development, Jagiellonian University, Gronostajowa 7, 30-387, Krakow, Poland

    Beata Bober

Authors
  1. Koji Tomita
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  2. Masateru Hasegawa
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  3. Suzue Arii
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  4. Kiyomi Tsuji
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  5. Beata Bober
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  6. Ken-ichi Harada
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Correspondence to Koji Tomita.

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Responsible editor: Philippe Garrigues

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Tomita, K., Hasegawa, M., Arii, S. et al. Characteristic oxidation behavior of β-cyclocitral from the cyanobacterium Microcystis . Environ Sci Pollut Res 23, 11998–12006 (2016). https://doi.org/10.1007/s11356-016-6369-y

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  • DOI: https://doi.org/10.1007/s11356-016-6369-y

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