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J Lipid Res. 2015 Apr;56(4):909-19. doi: 10.1194/jlr.M057919. Epub 2015 Feb 14.

Resveratrol and para-coumarate serve as ring precursors for coenzyme Q biosynthesis.

Author information

1
Department of Chemistry and Biochemistry and the Molecular Biology Institute, University of California, Los Angeles, CA 90095-1569.
2
Departments of Microbiology, Immunology, and Molecular Genetics University of California, Los Angeles, CA 90095-1569.
3
Departments of Microbiology, Immunology, and Molecular Genetics University of California, Los Angeles, CA 90095-1569 Molecular and Medical Pharmacology, University of California, Los Angeles, CA 90095-1569.

Abstract

Coenzyme Q (Q or ubiquinone) is a redox-active polyisoprenylated benzoquinone lipid essential for electron and proton transport in the mitochondrial respiratory chain. The aromatic ring 4-hydroxybenzoic acid (4HB) is commonly depicted as the sole aromatic ring precursor in Q biosynthesis despite the recent finding that para-aminobenzoic acid (pABA) also serves as a ring precursor in Saccharomyces cerevisiae Q biosynthesis. In this study, we employed aromatic (13)C6-ring-labeled compounds including (13)C6-4HB, (13)C6-pABA, (13)C6-resveratrol, and (13)C6-coumarate to investigate the role of these small molecules as aromatic ring precursors in Q biosynthesis in Escherichia coli, S. cerevisiae, and human and mouse cells. In contrast to S. cerevisiae, neither E. coli nor the mammalian cells tested were able to form (13)C6-Q when cultured in the presence of (13)C6-pABA. However, E. coli cells treated with (13)C6-pABA generated (13)C6-ring-labeled forms of 3-octaprenyl-4-aminobenzoic acid, 2-octaprenyl-aniline, and 3-octaprenyl-2-aminophenol, suggesting UbiA, UbiD, UbiX, and UbiI are capable of using pABA or pABA-derived intermediates as substrates. E. coli, S. cerevisiae, and human and mouse cells cultured in the presence of (13)C6-resveratrol or (13)C6-coumarate were able to synthesize (13)C6-Q. Future evaluation of the physiological and pharmacological responses to dietary polyphenols should consider their metabolism to Q.

KEYWORDS:

antioxidants; isoprenoids; lipids/chemistry; mass spectrometry; mitochondria; plant polyphenols; stilbene; ubiquinone

PMID:
25681964
PMCID:
PMC4373747
DOI:
10.1194/jlr.M057919
[Indexed for MEDLINE]
Free PMC Article

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