Skin permeation and comparative evaluation of gentisic acid ester derivatives as skin-lightening agents

Shun, Nan; Abraham, Marion; Choi, Myeong Jun; Kim, Jung Sun

doi:10.1016/s1773-2247(14)50034-2

Journal of Drug Delivery Science and Technology

2014

DOI: 10.1016/s1773-2247(14)50034-2

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Skin permeation and comparative evaluation of gentisic acid ester derivatives as skin-lightening agents

Nan Shun

Marion Abraham

Myeong Jun Choi

et al.

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Cited by 2 publications

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Maleylpyruvic Acid-Inducible Gene Expression System and Its Application for the Development of Gentisic Acid Biosensors

Kutraite,

Augustiniene,

Malys

2024

Anal. Chem.

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Gentisic acid is a secondary plant metabolite, known for its health benefits, not only widely used as a supplement but also implicated as a potential biomarker for cancer-associated metabolism alterations. To advance bioproduction and detection of this compound or its derivatives, cell-based approaches have become of interest in recent years. However, the lack of tools for high-throughput gentisic acid monitoring and compound-metabolizing organism screening limits the progress in this area. Here, we analyzed the gene cluster responsible for gentisic acid metabolism in Cupriavidus necator H16. The transcriptional regulator GtdR-based inducible gene expression system CnGtdR/P gtdA was elucidated, showing that it was activated when C. necator cells were subjected to gentisic acid. Subsequently, a 3maleylpyruvic acid was identified as a primary inducer for this inducible system. Furthermore, genes gtdA and gtdT, encoding for gentisate 1,2-dioxygenase and MFS transporter, were shown to be essential for inducible system activation in the presence of gentisic acid with GtdA enabling conversion of this phenolic acid into the inducer. The CnGtdRAT/P gtdA -based inducible system was employed to develop a whole-cell biosensor for the intracellular and extracellular detection of gentisic acid. The potential of the 3-maleylpyruvic acid-inducible system was demonstrated by its application in metabolic pathway research, detection of highly unstable 3-maleylpyruvic acid, and development of biosensors for the intracellular or extracellular determination of gentisic acid. In addition, the utility of the biosensor was emphasized by its application for detection of gentisic acid as a potential biomarker for cancer in urine samples.

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Maleylpyruvic Acid-Inducible Gene Expression System and Its Application for the Development of Gentisic Acid Biosensors

Kutraite,

Augustiniene,

Malys

2024

Anal. Chem.

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Divergent Synthesis of Natural Benzyl Salicylate and Benzyl Gentisate Glucosides

et al. 2020

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Herein is reported the first total synthesis of benzyl salicylate and benzyl gentisate glucosides present in various plant species, in particular the Salix genus, such as Populus balsamifera and P. trichocarpa. The method permits the synthesis of several natural phenolic acid derivatives and their glucosides starting from salicylic or gentisic acid. The divergent approach afforded access to three different acetylated glucosides from a common synthetic intermediate. The key step in the total synthesis of naturally occurring glycosidesthe selective deacetylation of the sugar moietywas achieved in the presence of a labile benzyl ester group by employing mild deacetylation conditions. The protocol permitted synthesis of trichocarpine (4 steps, 40% overall yield), isotrichocarpine (3 steps, 51% overall yield), trichoside (6 steps, 40% overall yield), and deoxytrichocarpine (3 steps, 42% overall yield) for the first time (>95% purity). Also, the optimized mild deacetylation conditions allowed synthesis of 2-O-acetylated derivatives of all four glycosides (5−17% overall yield, 90−95% purity), which are rare plant metabolites.

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Skin permeation and comparative evaluation of gentisic acid ester derivatives as skin-lightening agents

Cited by 2 publications

References 15 publications

Maleylpyruvic Acid-Inducible Gene Expression System and Its Application for the Development of Gentisic Acid Biosensors

Maleylpyruvic Acid-Inducible Gene Expression System and Its Application for the Development of Gentisic Acid Biosensors

Divergent Synthesis of Natural Benzyl Salicylate and Benzyl Gentisate Glucosides

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