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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...
Autores principales: | , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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MDPI
2013
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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. |
format | Online Article Text |
id | pubmed-3564165 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2013 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
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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