Isolation and Structural Determination of Two Novel Phlorotannins from the Brown Alga Ecklonia kurome Okamura, and Their Radical Scavenging Activities
作者:Mari Yotsu-Yamashita、Sawako Kondo、Shinya Segawa、Yi-Chin Lin、Haruhiko Toyohara、Hisatomi Ito、Keiichi Konoki、Yuko Cho、Takafumi Uchida
DOI:10.3390/md11010165
日期:——
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 IC50 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.
从食用海洋褐藻 Ecklonia kurome Okamura 制备的多酚粉中分离出两种分子量为 974 的新型绿单宁,暂命名为 974-A 和 974-B,并通过光谱法确定了它们的化学结构。从多酚粉末中分离出的 974-A 和 974-B 总产率约为 4%(重量比)。在 974-A 中,氯琥珀酰猕猴桃酚-A 的 A 环 C2′ 位的碳与三佛手醇-B 的 C 环 C2″ 位的碳形成了一个 C-C 键,而在 974-B 中,氯琥珀酰猕猴桃酚-B 和三佛手醇-B 以与 974-A 相同的方式形成了一个 C-C 键。这些结构得到了高分辨率-MS/MS 数据的支持。为了评估抗氧化活性,对 974-A、974-B 和四种已知的绿单宁进行了 2,2-二苯基-1-苦基肼(DPPH)自由基清除试验和使用 2′,7′-二氯荧光素二乙酸酯(DCFH-DA)的细胞内自由基清除试验。DPPH 试验结果表明,974-A、974-B、氯氟呋喃eckol-A 和二酮醇的 IC50 值明显小于氯氟呋喃eckol-B、氯葡萄糖醇、α-生育酚和抗坏血酸。此外,DCFH-DA 分析表明,在受测化合物中,974-A、974-B 和 dieckol 对细胞内活性氧的减少作用最强。