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Isolation and Structural Determination of Two Novel Phlorotannins from the Brown Alga Ecklonia kurome Okamura, and Their Radical Scavenging Activities

Two novel phlorotannins with a molecular weight of 974, temporarily named 974-A and 974-B, were isolated from the polyphenol powder prepared from the edible marine brown alga Ecklonia kurome Okamura, and their chemical structures were determined by spectroscopic method. The isolated yield of the tot...

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Autores principales: Yotsu-Yamashita, Mari, Kondo, Sawako, Segawa, Shinya, Lin, Yi-Chin, Toyohara, Haruhiko, Ito, Hisatomi, Konoki, Keiichi, Cho, Yuko, Uchida, Takafumi
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2013
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3564165/
https://www.ncbi.nlm.nih.gov/pubmed/23334528
http://dx.doi.org/10.3390/md11010165
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author Yotsu-Yamashita, Mari
Kondo, Sawako
Segawa, Shinya
Lin, Yi-Chin
Toyohara, Haruhiko
Ito, Hisatomi
Konoki, Keiichi
Cho, Yuko
Uchida, Takafumi
author_facet Yotsu-Yamashita, Mari
Kondo, Sawako
Segawa, Shinya
Lin, Yi-Chin
Toyohara, Haruhiko
Ito, Hisatomi
Konoki, Keiichi
Cho, Yuko
Uchida, Takafumi
author_sort Yotsu-Yamashita, Mari
collection PubMed
description Two novel phlorotannins with a molecular weight of 974, temporarily named 974-A and 974-B, were isolated from the polyphenol powder prepared from the edible marine brown alga Ecklonia kurome Okamura, and their chemical structures were determined by spectroscopic method. The isolated yield of the total of 974-A and 974-B was approximately 4% (w/w) from the polyphenol powder. In 974-A, the carbon at the C2′ position in the A ring of phlorofucofuroeckol-A forms a C–C bond with the carbon at the C2″ position of the C ring of triphloretol-B, while in 974-B, phlorofucofuroeckol-B and triphloretol-B form a C–C bond in the same manner as in 974-A. These structures were supported by high resolution-MS/MS data. To evaluate the antioxidant activities, the 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging assay and intracellular radical scavenging assay, using 2′,7′-dichlorofluorescin diacetate (DCFH-DA), were performed for 974-A, 974-B, and four known phlorotannins. The results of the DPPH assay showed that the IC(50) values of 974-A, 974-B, phlorofucofuroeckol-A, and dieckol were significantly smaller than those of phlorofucofuroeckol-B, phloroglucinol, α-tocopherol, and ascorbic acid. Furthermore, the DCFH-DA assay suggested that 974-A, 974-B, and dieckol reduce intracellular reactive oxygen species most strongly among the tested compounds.
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spelling pubmed-35641652013-02-11 Isolation and Structural Determination of Two Novel Phlorotannins from the Brown Alga Ecklonia kurome Okamura, and Their Radical Scavenging Activities Yotsu-Yamashita, Mari Kondo, Sawako Segawa, Shinya Lin, Yi-Chin Toyohara, Haruhiko Ito, Hisatomi Konoki, Keiichi Cho, Yuko Uchida, Takafumi Mar Drugs Article Two novel phlorotannins with a molecular weight of 974, temporarily named 974-A and 974-B, were isolated from the polyphenol powder prepared from the edible marine brown alga Ecklonia kurome Okamura, and their chemical structures were determined by spectroscopic method. The isolated yield of the total of 974-A and 974-B was approximately 4% (w/w) from the polyphenol powder. In 974-A, the carbon at the C2′ position in the A ring of phlorofucofuroeckol-A forms a C–C bond with the carbon at the C2″ position of the C ring of triphloretol-B, while in 974-B, phlorofucofuroeckol-B and triphloretol-B form a C–C bond in the same manner as in 974-A. These structures were supported by high resolution-MS/MS data. To evaluate the antioxidant activities, the 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging assay and intracellular radical scavenging assay, using 2′,7′-dichlorofluorescin diacetate (DCFH-DA), were performed for 974-A, 974-B, and four known phlorotannins. The results of the DPPH assay showed that the IC(50) values of 974-A, 974-B, phlorofucofuroeckol-A, and dieckol were significantly smaller than those of phlorofucofuroeckol-B, phloroglucinol, α-tocopherol, and ascorbic acid. Furthermore, the DCFH-DA assay suggested that 974-A, 974-B, and dieckol reduce intracellular reactive oxygen species most strongly among the tested compounds. MDPI 2013-01-18 /pmc/articles/PMC3564165/ /pubmed/23334528 http://dx.doi.org/10.3390/md11010165 Text en © 2013 by the authors; licensee MDPI, Basel, Switzerland. http://creativecommons.org/licenses/by/3.0/ This article is an open-access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
Yotsu-Yamashita, Mari
Kondo, Sawako
Segawa, Shinya
Lin, Yi-Chin
Toyohara, Haruhiko
Ito, Hisatomi
Konoki, Keiichi
Cho, Yuko
Uchida, Takafumi
Isolation and Structural Determination of Two Novel Phlorotannins from the Brown Alga Ecklonia kurome Okamura, and Their Radical Scavenging Activities
title Isolation and Structural Determination of Two Novel Phlorotannins from the Brown Alga Ecklonia kurome Okamura, and Their Radical Scavenging Activities
title_full Isolation and Structural Determination of Two Novel Phlorotannins from the Brown Alga Ecklonia kurome Okamura, and Their Radical Scavenging Activities
title_fullStr Isolation and Structural Determination of Two Novel Phlorotannins from the Brown Alga Ecklonia kurome Okamura, and Their Radical Scavenging Activities
title_full_unstemmed Isolation and Structural Determination of Two Novel Phlorotannins from the Brown Alga Ecklonia kurome Okamura, and Their Radical Scavenging Activities
title_short Isolation and Structural Determination of Two Novel Phlorotannins from the Brown Alga Ecklonia kurome Okamura, and Their Radical Scavenging Activities
title_sort isolation and structural determination of two novel phlorotannins from the brown alga ecklonia kurome okamura, and their radical scavenging activities
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3564165/
https://www.ncbi.nlm.nih.gov/pubmed/23334528
http://dx.doi.org/10.3390/md11010165
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