Profiling of the molecular weight and structural isomer abundance of macroalgae-derived phlorotannins.
Profiling of the molecular weight and structural isomer abundance of macroalgae-derived phlorotannins.
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DOI：
10.3390/md13010509
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发表时间：
2015-01-16
期刊：
影响因子：
5.4
通讯作者：
Smyth TJ
中科院分区：
文献类型：
--
作者：
Heffernan N;Brunton NP;FitzGerald RJ;Smyth TJ
间苯三酚是一组大型藻类特有的间苯三酚(1，3，5-三羟基苯)的复杂聚合物。这些酚类化合物是褐藻细胞壁不可或缺的结构成分，但也具有许多次生生态作用，如抵御紫外线辐射和抵御放牧。本研究采用超高效液相色谱(UPLC)与串联质谱仪(TMS)相结合的方法，研究了从爱尔兰沿海捕捞的大型藻类(锯齿褐藻、微囊藻、细长毛藻和节节胞藻)中提取的邻苯二甲酸单宁的异构体复杂性和差异。用抗氧化活性和总酚含量分析作为生产邻苯二甲酸单宁组分的指标，通过分子量截断透析和随后的闪蒸层析来描述这些大型藻类中的邻氯单宁异构体。利用具有多反应监测(MRM)的UPLC-MS对这些馏分进行了分析，并测定了3至16个单体的比分子质量间邻苯二甲酸单宁的异构化程度。大多数低分子量(LMW)间苯三酚的相对分子质量范围相当于4-12个间苯三酚单体。每种大型藻类内的异构化程度不同，导致特定相对分子质量的邻苯二甲酸异构体的数量有很大不同。泡囊镰刀菌在一个特定分子质量上的异构体数量最多，为61个，相当于12个间苯三酚单位(PGU)。这些结果突出了这些提取物的复杂性，并强调了这些化合物的结构阐明所涉及的挑战。
Phlorotannins are a group of complex polymers of phloroglucinol (1,3,5-trihydroxybenzene) unique to macroalgae. These phenolic compounds are integral structural components of the cell wall in brown algae, but also play many secondary ecological roles such as protection from UV radiation and defense against grazing. This study employed Ultra Performance Liquid Chromatography (UPLC) with tandem mass spectrometry to investigate isomeric complexity and observed differences in phlorotannins derived from macroalgae harvested off the Irish coast (Fucus serratus, Fucus vesiculosus, Himanthalia elongata and Cystoseira nodicaulis). Antioxidant activity and total phenolic content assays were used as an index for producing phlorotannin fractions, enriched using molecular weight cut-off dialysis with subsequent flash chromatography to profile phlorotannin isomers in these macroalgae. These fractions were profiled using UPLC-MS with multiple reaction monitoring (MRM) and the level of isomerization for specific molecular weight phlorotannins between 3 and 16 monomers were determined. The majority of the low molecular weight (LMW) phlorotannins were found to have a molecular weight range equivalent to 4–12 monomers of phloroglucinol. The level of isomerization within the individual macroalgal species differed, resulting in substantially different numbers of phlorotannin isomers for particular molecular weights. F. vesiculosus had the highest number of isomers of 61 at one specific molecular mass, corresponding to 12 phloroglucinol units (PGUs). These results highlight the complex nature of these extracts and emphasize the challenges involved in structural elucidation of these compounds.
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