Evidence for covalent lipoyl adduction with dopaquinone following tyrosinase-catalyzed oxidation

Biochemical and Biophysical Research Communications
Kentaro Tsuji-NaitoTakao Tehara

Abstract

Previous studies have examined the conjugation of sulfhydryl compounds such as L-cysteine and glutathione with DOPA-quinone following the oxidation of tyrosine and DOPA by tyrosinase. These covalent reactions play a key role in the regulation and metabolism of pigment cells. We report on the first direct evidence for the formation of lipoyl adducts in reactions of thiol groups with DOPA-quinone in dihydrolipoic acid (6,8-dimercaptooctanoic acid [DHLA]). Incubating DHLA with DOPA-quinone followed by tyrosinase-catalyzed oxidation resulted in the three products predicted by HPLC-UV and LC-ESI(-)-MS analyses for DHLA DOPA conjugates. In the current study, we identified 5-S-lipoyl-DOPA among the principal products isolated by HPLC and characterized by FAB(-)-MS, ESI(-)-MS/MS, and 1H NMR, 2D-COSY studies. Collectively, these results suggest that DHLA undergoes sulfhydryl conjugation with DOPA-quinone, pointing to the involvement of thiol-reactive metabolites.

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Citations

Oct 5, 2013·European Journal of Medicinal Chemistry·Chichong LuKyu Yun Chai
Dec 22, 2012·Journal of Agricultural and Food Chemistry·Lucia PanzellaMarco d'Ischia
Jun 25, 2013·Journal of Agricultural and Food Chemistry·Alessandro VendittiFabiana Antognoni
Nov 6, 2007·Biological & Pharmaceutical Bulletin·Ji-Hoon YoonJae-Kwan Hwang
May 3, 2008·Biological & Pharmaceutical Bulletin·Yumi ChoJae-Kwan Hwang
Aug 2, 2008·Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan·Mitsuo MatsukiTatsuji Matsumoto
Nov 7, 2006·Pigment Cell Research·Francisco SolanoGhanem Ghanem
Jun 14, 2008·The Journal of Pharmacy and Pharmacology·Jin-Hwa KimHyeong-Bae Pyo
Oct 30, 2010·Phytotherapy Research : PTR·Chan Woo LeeJae Kwan Hwang
Jul 19, 2012·Chembiochem : a European Journal of Chemical Biology·Marcus J C Long, Lizbeth Hedstrom
Jul 26, 2018·International Journal of Molecular Sciences·Raffaella MicilloConchi Olivares
Jun 13, 2018·Journal of Clinical Biochemistry and Nutrition·Yoji Kato, Naoko Suga

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