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Characterization of inclusion complex of vitamin E compound with 2,6-di-O-methylated β-cyclodextrin as the solubility enhancer and its kinetic determination for radical scavenging ability

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Abstract

The structure of the inclusion complex of α-tocopherol (vitamin E compound) with 2,6-di-O-methylated β-cyclodextrin (DM-β-CD) was characterized by 2D ROESY NMR measurements, suggesting that DM-β-CD includes the side-chain moiety of α-tocopherol. The inclusion complexation of DM-β-CD showed the usefulness of water solubilizer for the radical scavenging assay of vitamin E compounds in aqueous solution. Using the electron paramagnetic resonance (EPR) competitive spin trapping method, we determined the oxygen radical (RO∙) scavenging abilities of seven vitamin E compounds (tocopherols and tocotrienols), which were solubilized by DM-β-CD in water. The order of the RO∙ radical scavenging abilities for vitamin E compounds solubilized by DM-β-CD are α- > β- ≈ γ- > δ-, which is in agreement with the oxidation potential values of antioxidants. It is noted that the RO∙ radical scavenging abilities of tocotrienols are comparable to those of tocopherols. Based on the results, the mechanism of the antioxidant reaction of vitamin E compounds with the RO∙ radical is discussed.

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Acknowledgments

We thank Professor Y. Kotake of the Oklahoma Medical Research Foundation for fruitful discussions. This work was supported in part by a research grant from Japan Food Chemical Research Foundation.

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  1. Department of Chemistry, Faculty of Science, Okayama University, 3-1-1 Tsushima-naka, Kita-ku, Okayama, 700-8530, Japan

    Yoshimi Sueishi, Masashi Hori & Naoya Inazumi

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  1. Yoshimi Sueishi
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  2. Masashi Hori
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  3. Naoya Inazumi
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Correspondence to Yoshimi Sueishi.

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Sueishi, Y., Hori, M. & Inazumi, N. Characterization of inclusion complex of vitamin E compound with 2,6-di-O-methylated β-cyclodextrin as the solubility enhancer and its kinetic determination for radical scavenging ability. J Incl Phenom Macrocycl Chem 72, 467–472 (2012). https://doi.org/10.1007/s10847-011-0018-3

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