3-O-alkylascorbic acids as free-radical quenchers: synthesis and inhibitory effect on lipid peroxidation.

doi:10.1021/JM00111A034

Paper

3-O-alkylascorbic acids as free-radical quenchers: synthesis and inhibitory effect on lipid peroxidation.

Published Jul 1, 1991 · Y. Nihro, H. Miyataka, Tadamitsu Sudo

Journal of medicinal chemistry

Q1 SJR score

64

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1

Influential Citations

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Abstract

A novel series of 3-O-alkylascorbic acids (3-RASA, 3a-n) was synthesized to act as radical scavengers for active oxygen species and free radicals, and their redox potentials and inhibitory effects on lipid peroxidation in rat liver microsomes were evaluated. The redox potentials of the 3-RASA compounds were increased by the substituent group to 90-190 mV above the potential for ascorbic acid (i.e., 3-RASA compounds were harder to oxidize). Although 3-O-dodecylascorbic acid (3c) and 3-O-(decylcarbomethyl)ascorbic acid (3i) differed in their redox potentials, they both markedly inhibited lipid peroxidation in rat liver microsomes to a similar extent (IC50 = 3.1 and 3.3 X 10(-6) M, respectively). Structure-activity relationship studies demonstrated that the anti lipid peroxidation activity of the 3-RASA compounds was markedly dependent upon their hydrophobicity.

In Vitro Study

Study Snapshot

3-O-alkylascorbic acids effectively inhibit lipid peroxidation in rat liver microsomes, with their anti-lipid peroxidation activity largely dependent on their hydrophobicity.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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3-O-alkylascorbic acids as free-radical quenchers: synthesis and inhibitory effect on lipid peroxidation.

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References

Citations

Switching Photoluminescence “On‐Off‐On” for Detection of Chromium (VI) Ion and Ascorbic Acid with N,S‐Codoped Carbon Dots

This study developed a rapid detection platform for chromium (VI) and ascorbic acid using metal-free, environmentally benign carbon dots, demonstrating a new rapid detection method in seconds.

Antiallergic Activity of 3-O-Dodecyl-l-ascorbic Acid

3-O-dodecyl-l-ascorbic acid (compound 8) shows strong inhibitory activity against antigen-stimulated degranulation and may be a candidate for antiallergic treatment.

Facile and improved synthesis of the 2-O-β-d-glucopyranosyl-l-ascorbic acid

This study successfully synthesized 2-O--d-glucopyranosyl-l-ascorbic acid (AA-2G) in five steps, with a 31.4% overall yield, and the final product is pure enough for application purposes.

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Ascorbic Acid in Skin Health

Ascorbic acid, a vitamin C, is used topically in dermatology to treat and prevent photoaging and hyperpigmentation, with potential roles in maintaining skin health and overall well-being.