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The Formation of Lipid Hydroperoxide-Derived Amide-Type Lysine Adducts on Proteins: A Review of Current Knowledge

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Lipid Hydroperoxide-Derived Modification of Biomolecules

Part of the book series: Subcellular Biochemistry ((SCBI,volume 77))

Abstract

Lipid peroxidation is an important biological reaction. In particular, polyunsaturated fatty acid (PUFA) can be oxidized easily. Peroxidized lipids often react with other amines accompanied by the formation of various covalent adducts. Novel amide-type lipid-lysine adducts have been identified from an in vitro reaction mixture of lipid hydroperoxide with a protein, biological tissues exposed to conditions of oxidative stress and human urine from a healthy person. In this chapter, the current knowledge of amide type adducts is reviewed with a focus on the evaluation of functional foods and diseases with a history of discovery of hexanoyl-lysine (HEL). Although there is extensive research on HEL and other amide-type adducts, the mechanism of generation of the amide bond remains unclear. We have found that the decomposed aldehyde plus peroxide combined with a lysine moiety does not fully explain the formation of the amide-type lipid-lysine adduct that is generated by lipid hydroperoxide. Singlet oxygen or an excited state of the ketone generated from the lipid hydroperoxide may also contribute to the formation of the amide linkage. The amide-adducts may prove useful not only for the detection of oxidative stress induced by disease but also for the estimation of damage caused by an excess intake of PUFA.

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Abbreviations

PUFA:

Polyunsaturated fatty acid

HEL:

Hexanoyl-lysine

13-HPODE:

13-hydroperoxyoctadecadienoic acid

BGK:

Benzoyl-glycyl-L-lysine

LC/MS/MS:

Liquid chromatography tandem mass spectrometry

SUL:

Succinyl-lysine

GLL:

Glutary-lysine

AZL:

Azelayl-lysine

PRL:

Propanoyl-lysine

HHE:

4-hydroxy-2-hexenal

DHA:

Docosahexaenoic acid

KLH:

Keyhole limpet hemocyanin

BSA:

Bovine serum albumin

HEEA:

Hexanoyl-ethanolamine

8OxodG/8OHdG:

8-oxo-deoxyguanosine

MRM:

Multiple reaction monitoring

LDL:

Low-density lipoprotein

MDA:

Malondialdehyde

CML:

Carboxymethyllysine

ACR:

Acrolein

CPT I:

Carnitine palmitoyltransferase I

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Acknowledgments

I would like to sincerely thank Professor Toshihiko Osawa for his encouragement during this study. I appreciate Professor Sayuri Miyamoto for her valuable comments. I express my thanks to Mr. Akihiro Yoshida (Nakatsugawa Municipal Hospital) and Dr. Michitaka Naito (Sugiyama-Jyogakuen University) for kindly providing the urine samples.

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  1. School of Human Science and Environment, University of Hyogo, Himeji, Hyogo, Japan

    Yoji Kato

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  1. School of Human Science & Environment, University of Hyogo, Himeji, Hyogo, Japan

    Yoji Kato

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Kato, Y. (2014). The Formation of Lipid Hydroperoxide-Derived Amide-Type Lysine Adducts on Proteins: A Review of Current Knowledge. In: Kato, Y. (eds) Lipid Hydroperoxide-Derived Modification of Biomolecules. Subcellular Biochemistry, vol 77. Springer, Dordrecht. https://doi.org/10.1007/978-94-007-7920-4_2

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