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Oxidative Pattern from Fluorescent Light Exposition of Crystalline Cholesterol

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Abstract

The photo-oxidation of crystalline cholesterol in the presence of hematoporphyrin was kinetically studied. Samples were exposed to fluorescent light at 12 °C for 48 h (Test-A) and 21 days (Test-B). A method based on aminopropyl solid-phase extraction (SPE), followed by GC-MS analysis was employed for the identification and quantification of cholesterol oxidative compounds (COPs). In early stages of photo-oxidation (Test-A), a hyperbolic behavior on peroxides value was found, but not quantifiable secondary products were detected. In Test-B, 58 % of cholesterol was remained after exposure, due probably to exhaustion of hematoporphyrin and/or physical state of sample. Type II photo-oxidation seemed to be quantitatively predominant, in respect to Type I. 3,6-dione and 6β-OH generated in highest amount, following by 5,6α-epoxy and 7α-OH. Oxidative pattern shows the formation of other minor compounds, such as 7-ketostanol, 6-ketostanol and 4β-OH. This last one was previously attributed only to enzymatic oxidation. Finally, the relationship between 7-keto and 25-OH were strongly shifted toward the side-chain product, due probably to the exposure of aliphatic chain in crystalline cholesterol. These results confirm the crucial importance of physical state of cholesterol during photo-oxidation, giving an interesting and more complex degradation behavior.

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Abbreviations

7α-OH:

7α-hydroxycholesterol

7β-OH:

7β-hydroxycholesterol

5,6α-epoxy:

5,6α-epoxycholesterol

5,6β-epoxy:

5,6β-epoxycholesterol

4β-OH:

4β-hydroxycholesterol

6β-OH:

6β-hydroxycholesterol

7-ketostanol:

7-ketocholestanol

6-ketostanol:

6-ketocholestanol

3,6-dione:

5α-cholestestan-3,6-dione

7-keto:

7-ketocholesterol

25-OH:

25-hydroxycholesterol

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Acknowledgment

We thank Stefano Savioli and Mara Mandrioli (University of Bologna) for their technical support and assistance during sample analysis, and Carlo Barnaba (ITESO) for manuscript revision.

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Authors and Affiliations

  1. Departamento de Procesos Tecnológicos e Industriales, Instituto Tecnológico de Estudios Superiores de Occidente (ITESO), Periférico Sur Manuel Gómez Morín 8585, 45604, Tlaquepaque, Jal, Mexico

    Ilce Gabriela Medina-Meza

  2. Dipartimento di Scienze degli Alimenti, Università di Bologna, viale Fanin 40, 40127, Bologna, Italy

    María Teresa Rodríguez-Estrada & Giovanni Lercker

  3. UNIDA, Instituto Tecnológico de Veracruz, M.A. de Quevedo 2779, Veracruz, Ver., 91897, Mexico

    Hugo Sergio García

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  1. Ilce Gabriela Medina-Meza
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  2. María Teresa Rodríguez-Estrada
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  3. Hugo Sergio García
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  4. Giovanni Lercker
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Correspondence to Ilce Gabriela Medina-Meza.

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Medina-Meza, I.G., Rodríguez-Estrada, M.T., García, H.S. et al. Oxidative Pattern from Fluorescent Light Exposition of Crystalline Cholesterol. Food Biophysics 7, 209–219 (2012). https://doi.org/10.1007/s11483-012-9259-y

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