Extraction and PTP1B inhibitory activity of bromophenols from the marine red alga Symphyocladia latiuscula
Previously, we had characterized several structurally interesting brominated phenols from the marine red alga Symphyocladia latiuscula collected from various sites. However, Phytochemical investigations on this species collected from the Weihai coastline of Shandong Province remains blank. Therefore...
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| Published in | Chinese journal of oceanology and limnology Vol. 29; no. 3; pp. 686 - 690 |
|---|---|
| Main Author | |
| Format | Journal Article |
| Language | English |
| Published |
Heidelberg
SP Science Press
01.05.2011
Springer Nature B.V |
| Subjects | |
| Online Access | Get full text |
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| Abstract | Previously, we had characterized several structurally interesting brominated phenols from the marine red alga Symphyocladia latiuscula collected from various sites. However, Phytochemical investigations on this species collected from the Weihai coastline of Shandong Province remains blank. Therefore, we characterized the chemical constituents of individuals of this species collected from the region. Eight bromophenols were isolated and identified. Using detailed spectroscopic techniques and comparisons with published data, these compounds were identified as 2,3-dibromo-4,5-dihydroxybenzyl methyl ether （1）, 3,5-dibromo-4-hydroxybenzoic acid （2）, 2,3,6-tribromo-4,5-dihydroxymethylbenzene （3）, 2,3,6-tribromo-4,5-dihydroxybenzaldehyde （4）, 2,3,6-tribromo-4,5-dihydroxybenzyl methyl ether （5）, bis（2,3,6-tribromo-4,5-dihydroxyphenyl）methane （6）, 1,2-bis（2,3,6-tribromo-4,5-dihydroxyphenyl）-ethane （7）, and 1-（2,3,6-tribromo-4,5-dihydroxybenzyl）-pyrrolidin-2-one （8）, Among these compounds, 1 and 2 were isolated for the first time from S. latiuscula. Each compound was evaluated on the ability to inhibit protein tyrosine phosphatase 1B （PTP1B）, which is a potential therapeutic target in the treatment of type 2 diabetes. Bromophenols 5, 6, and 7 showed strong activities with IC50 values of 3.9, 4.3, and 3.5 μmol/L, respectively. This study provides further evidence that bromophenols are predominant among the chemical constituents of Symphyocladia, and that some of these compounds may be candidates for the development of anti-diabetes drugs. |
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| AbstractList | Previously, we had characterized several structurally interesting brominated phenols from the marine red alga Symphyocladia latiuscula collected from various sites. However, Phytochemical investigations on this species collected from the Weihai coastline of Shandong Province remains blank. Therefore, we characterized the chemical constituents of individuals of this species collected from the region. Eight bromophenols were isolated and identified. Using detailed spectroscopic techniques and comparisons with published data, these compounds were identified as 2,3-dibromo-4,5-dihydroxybenzyl methyl ether (1), 3,5-dibromo-4-hydroxybenzoic acid (2), 2,3,6-tribromo-4,5-dihydroxymethylbenzene (3), 2,3,6-tribromo-4,5-dihydroxybenzaldehyde (4), 2,3,6-tribromo-4,5-dihydroxybenzyl methyl ether (5), bis(2,3,6-tribromo-4,5-dihydroxyphenyl)methane (6), 1,2-bis(2,3,6-tribromo-4,5-dihydroxyphenyl)-ethane (7), and 1-(2,3,6-tribromo-4,5-dihydroxybenzyl)-pyrrolidin-2-one (8). Among these compounds, 1 and 2 were isolated for the first time from S. latiuscula. Each compound was evaluated on the ability to inhibit protein tyrosine phosphatase 1B (PTP1B), which is a potential therapeutic target in the treatment of type 2 diabetes. Bromophenols 5, 6, and 7 showed strong activities with IC50 values of 3.9, 4.3, and 3.5 μmol/L, respectively. This study provides further evidence that bromophenols are predominant among the chemical constituents of Symphyocladia, and that some of these compounds may be candidates for the development of anti-diabetes drugs. Previously, we had characterized several structurally interesting brominated phenols from the marine red alga Symphyocladia latiuscula collected from various sites. However, Phytochemical investigations on this species collected from the Weihai coastline of Shandong Province remains blank. Therefore, we characterized the chemical constituents of individuals of this species collected from the region. Eight bromophenols were isolated and identified. Using detailed spectroscopic techniques and comparisons with published data, these compounds were identified as 2,3-dibromo-4,5-dihydroxybenzyl methyl ether （1）, 3,5-dibromo-4-hydroxybenzoic acid （2）, 2,3,6-tribromo-4,5-dihydroxymethylbenzene （3）, 2,3,6-tribromo-4,5-dihydroxybenzaldehyde （4）, 2,3,6-tribromo-4,5-dihydroxybenzyl methyl ether （5）, bis（2,3,6-tribromo-4,5-dihydroxyphenyl）methane （6）, 1,2-bis（2,3,6-tribromo-4,5-dihydroxyphenyl）-ethane （7）, and 1-（2,3,6-tribromo-4,5-dihydroxybenzyl）-pyrrolidin-2-one （8）, Among these compounds, 1 and 2 were isolated for the first time from S. latiuscula. Each compound was evaluated on the ability to inhibit protein tyrosine phosphatase 1B （PTP1B）, which is a potential therapeutic target in the treatment of type 2 diabetes. Bromophenols 5, 6, and 7 showed strong activities with IC50 values of 3.9, 4.3, and 3.5 μmol/L, respectively. This study provides further evidence that bromophenols are predominant among the chemical constituents of Symphyocladia, and that some of these compounds may be candidates for the development of anti-diabetes drugs. Previously, we had characterized several structurally interesting brominated phenols from the marine red alga Symphyocladia latiuscula collected from various sites. However, Phytochemical investigations on this species collected from the Weihai coastline of Shandong Province remains blank. Therefore, we characterized the chemical constituents of individuals of this species collected from the region. Eight bromophenols were isolated and identified. Using detailed spectroscopic techniques and comparisons with published data, these compounds were identified as 2,3-dibromo-4,5-dihydroxybenzyl methyl ether ( 1 ), 3,5-dibromo-4-hydroxybenzoic acid ( 2 ), 2,3,6-tribromo-4,5-dihydroxymethylbenzene ( 3 ), 2,3,6-tribromo-4,5-dihydroxybenzaldehyde ( 4 ), 2,3,6-tribromo-4,5-dihydroxybenzyl methyl ether ( 5 ), bis(2,3,6-tribromo-4,5-dihydroxyphenyl)methane ( 6 ), 1,2-bis(2,3,6-tribromo-4,5-dihydroxyphenyl)-ethane ( 7 ), and 1-(2,3,6-tribromo-4,5-dihydroxybenzyl)-pyrrolidin-2-one ( 8 ). Among these compounds, 1 and 2 were isolated for the first time from S. latiuscula. Each compound was evaluated on the ability to inhibit protein tyrosine phosphatase 1B (PTP1B), which is a potential therapeutic target in the treatment of type 2 diabetes. Bromophenols 5 , 6 , and 7 showed strong activities with IC50 values of 3.9, 4.3, and 3.5 μmol/L, respectively. This study provides further evidence that bromophenols are predominant among the chemical constituents of Symphyocladia , and that some of these compounds may be candidates for the development of anti-diabetes drugs. Previously, we had characterized several structurally interesting brominated phenols from the marine red alga Symphyocladia latiuscula collected from various sites. However, Phytochemical investigations on this species collected from the Weihai coastline of Shandong Province remains blank. Therefore, we characterized the chemical constituents of individuals of this species collected from the region. Eight bromophenols were isolated and identified. Using detailed spectroscopic techniques and comparisons with published data, these compounds were identified as 2,3-dibromo-4,5-dihydroxybenzyl methyl ether (1), 3,5-dibromo-4-hydroxybenzoic acid (2), 2,3,6-tribromo-4,5-dihydroxymethylbenzene (3), 2,3,6-tribromo-4,5-dihydroxybenzaldehyde (4), 2,3,6-tribromo-4,5-dihydroxybenzyl methyl ether (5), bis(2,3,6-tribromo-4,5-dihydroxyphenyl)methane (6), 1,2-bis(2,3,6-tribromo-4,5-dihydroxyphenyl)-ethane (7), and 1-(2,3,6-tribromo-4,5-dihydroxybenzyl)-pyrrolidin-2-one (8). Among these compounds, 1 and 2 were isolated for the first time from S. latiuscula. Each compound was evaluated on the ability to inhibit protein tyrosine phosphatase 1B (PTP1B), which is a potential therapeutic target in the treatment of type 2 diabetes. Bromophenols 5, 6, and 7 showed strong activities with IC50 values of 3.9, 4.3, and 3.5 mu mol/L, respectively. This study provides further evidence that bromophenols are predominant among the chemical constituents of Symphyocladia, and that some of these compounds may be candidates for the development of anti-diabetes drugs. |
| Author | 刘旭 李晓明 高立信 崔传明 李春顺 李佳 王斌贵 |
| AuthorAffiliation | Key Laboratory of Experimental Marine Biology, Institute of Oceanology, Chinese Academy of Sciences, Qingdao 266071 China Graduate University of Chinese Academy of Sciences, Beijing 100049, China National Center for Drug Screening, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China |
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| Keywords | Rhodomelaceae marine alga protein tyrosine phosphatase 1B (PTP1B) bromophenol |
| Language | English |
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| Notes | LIU Xu, LI Xiaoming, GAO Lixin, CUI Chuanming, LI Chunshun, LI Jia , WANG Bingui （1 Key Laboratory of Experimental Marine Biology, Institute of Oceanology, Chinese Academy of Sciences, Qingdao 266071 China 2 Graduate University of Chinese Academy of Sciences, Beijing 100049, China 3 National Center for Drug Screening, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China ） marine alga; Rhodomelaceae; Symphyocladia latiuscula; bromophenol; protein tyrosine phosphatase 1B （PTP1B） 37-1150/P Previously, we had characterized several structurally interesting brominated phenols from the marine red alga Symphyocladia latiuscula collected from various sites. However, Phytochemical investigations on this species collected from the Weihai coastline of Shandong Province remains blank. Therefore, we characterized the chemical constituents of individuals of this species collected from the region. Eight bromophenols were isolated and identified. Using detailed spectroscopic techniques and comparisons with published data, these compounds were identified as 2,3-dibromo-4,5-dihydroxybenzyl methyl ether （1）, 3,5-dibromo-4-hydroxybenzoic acid （2）, 2,3,6-tribromo-4,5-dihydroxymethylbenzene （3）, 2,3,6-tribromo-4,5-dihydroxybenzaldehyde （4）, 2,3,6-tribromo-4,5-dihydroxybenzyl methyl ether （5）, bis（2,3,6-tribromo-4,5-dihydroxyphenyl）methane （6）, 1,2-bis（2,3,6-tribromo-4,5-dihydroxyphenyl）-ethane （7）, and 1-（2,3,6-tribromo-4,5-dihydroxybenzyl）-pyrrolidin-2-one （8）, Among these compounds, 1 and 2 were isolated for the first time from S. latiuscula. Each compound was evaluated on the ability to inhibit protein tyrosine phosphatase 1B （PTP1B）, which is a potential therapeutic target in the treatment of type 2 diabetes. Bromophenols 5, 6, and 7 showed strong activities with IC50 values of 3.9, 4.3, and 3.5 μmol/L, respectively. This study provides further evidence that bromophenols are predominant among the chemical constituents of Symphyocladia, and that some of these compounds may be candidates for the development of anti-diabetes drugs. ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 14 content type line 23 |
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| Snippet | Previously, we had characterized several structurally interesting brominated phenols from the marine red alga Symphyocladia latiuscula collected from various... Previously, we had characterized several structurally interesting brominated phenols from the marine red alga Symphyocladia latiuscula collected from various... |
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| SubjectTerms | Algae Bromination Constituents Diabetes Diabetes mellitus (non-insulin dependent) Drug development Earth and Environmental Science Earth Sciences Ethane Marine Marine biology Oceanography p-Hydroxybenzoic acid Pharmacology Phenols Phosphatase Protein-tyrosine-phosphatase Proteins R&D Research & development Spectroscopic techniques Symphyocladia latiuscula Therapeutic targets Tyrosine 二羟基苯基 二羟基苯甲醛 化学成分特征 抑制活性 提取 植物化学物质 海洋红藻 蛋白酪氨酸磷酸酶 |
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| Title | Extraction and PTP1B inhibitory activity of bromophenols from the marine red alga Symphyocladia latiuscula |
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