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pH Stability and Antioxidant Power of CycloDOPA and Its Derivatives

CycloDOPA (leukodopachrome), a well known metabolite of tyrosine, is a precursor of melanine in mammalian organisms and of the pigment betalain in plants. However, the isolation of cycloDOPA from natural sources has not been widely reported. In the present work, the stabilities of cycloDOPA and cycl...

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Autores principales: Nakagawa, Shiori, Tachrim, Zetryana Puteri, Kurokawa, Natsumi, Ohashi, Fumina, Sakihama, Yasuko, Suzuki, Takeyuki, Hashidoko, Yasuyuki, Hashimoto, Makoto
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2018
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6222597/
https://www.ncbi.nlm.nih.gov/pubmed/30081515
http://dx.doi.org/10.3390/molecules23081943
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author Nakagawa, Shiori
Tachrim, Zetryana Puteri
Kurokawa, Natsumi
Ohashi, Fumina
Sakihama, Yasuko
Suzuki, Takeyuki
Hashidoko, Yasuyuki
Hashimoto, Makoto
author_facet Nakagawa, Shiori
Tachrim, Zetryana Puteri
Kurokawa, Natsumi
Ohashi, Fumina
Sakihama, Yasuko
Suzuki, Takeyuki
Hashidoko, Yasuyuki
Hashimoto, Makoto
author_sort Nakagawa, Shiori
collection PubMed
description CycloDOPA (leukodopachrome), a well known metabolite of tyrosine, is a precursor of melanine in mammalian organisms and of the pigment betalain in plants. However, the isolation of cycloDOPA from natural sources has not been widely reported. In the present work, the stabilities of cycloDOPA and cycloDOPA methyl ester at various pH levels were studied. Both compounds were stable under acidic conditions. By contrast, both compounds were unstable when the pH was shifted from neutral to basic to form indole derivatives as major products. Based on the pH stability, cycloDOPA and its derivatives were subjected to the DPPH radical scavenging assay for the first time.
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spelling pubmed-62225972018-11-13 pH Stability and Antioxidant Power of CycloDOPA and Its Derivatives Nakagawa, Shiori Tachrim, Zetryana Puteri Kurokawa, Natsumi Ohashi, Fumina Sakihama, Yasuko Suzuki, Takeyuki Hashidoko, Yasuyuki Hashimoto, Makoto Molecules Article CycloDOPA (leukodopachrome), a well known metabolite of tyrosine, is a precursor of melanine in mammalian organisms and of the pigment betalain in plants. However, the isolation of cycloDOPA from natural sources has not been widely reported. In the present work, the stabilities of cycloDOPA and cycloDOPA methyl ester at various pH levels were studied. Both compounds were stable under acidic conditions. By contrast, both compounds were unstable when the pH was shifted from neutral to basic to form indole derivatives as major products. Based on the pH stability, cycloDOPA and its derivatives were subjected to the DPPH radical scavenging assay for the first time. MDPI 2018-08-03 /pmc/articles/PMC6222597/ /pubmed/30081515 http://dx.doi.org/10.3390/molecules23081943 Text en © 2018 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Nakagawa, Shiori
Tachrim, Zetryana Puteri
Kurokawa, Natsumi
Ohashi, Fumina
Sakihama, Yasuko
Suzuki, Takeyuki
Hashidoko, Yasuyuki
Hashimoto, Makoto
pH Stability and Antioxidant Power of CycloDOPA and Its Derivatives
title pH Stability and Antioxidant Power of CycloDOPA and Its Derivatives
title_full pH Stability and Antioxidant Power of CycloDOPA and Its Derivatives
title_fullStr pH Stability and Antioxidant Power of CycloDOPA and Its Derivatives
title_full_unstemmed pH Stability and Antioxidant Power of CycloDOPA and Its Derivatives
title_short pH Stability and Antioxidant Power of CycloDOPA and Its Derivatives
title_sort ph stability and antioxidant power of cyclodopa and its derivatives
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6222597/
https://www.ncbi.nlm.nih.gov/pubmed/30081515
http://dx.doi.org/10.3390/molecules23081943
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