Extraction and PTP1B inhibitory activity of bromophenols from the marine red alga Symphyocladia latiuscula

• Published in: Chinese journal of oceanology and limnology Vol. 29; no. 3; pp. 686 - 690
• Main Author: 刘旭 李晓明 高立信 崔传明 李春顺 李佳 王斌贵
• Format: Journal Article
• Language: English
• Published: Heidelberg SP Science Press 01.05.2011; Springer Nature B.V
• Subjects: 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; INW, China, People's Rep., Shandong Prov; INW, China, People's Rep., Shandong Prov., Weihai; Rhodomelaceae; marine alga; protein tyrosine phosphatase 1B (PTP1B); bromophenol
• ISSN: 0254-4059; 2096-5508; 1993-5005; 2523-3521
• DOI: 10.1007/s00343-011-0136-1

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.