Laboratoire d'Études et de Recherche sur le Matériau Bois, EA4370 USC INRA, Université de Lorraine, Faculté des Sciences et Technologies , Boulevard des Aiguillettes, 54506 Vandœuvre-lès-Nancy, France.
J Nat Prod. 2017 Jun 23;80(6):1783-1790. doi: 10.1021/acs.jnatprod.6b01124. Epub 2017 Jun 7.
The lignan 7'-hydroxymatairesinol (1), extracted from the knotwoods of fir (Abies alba), spruce (Picea abies), and Douglas fir (Pseudotsuga menziesii), exhibited unexpected reactivity when esterification reactions were attempted on the hydroxy group at position C-7'. To circumvent the rapid intramolecular cyclization procedure, leading quantitatively to the lignan conidendrin (7), a simple strategy for 7'-esterification of 1 under mild conditions (three steps, up to 80% overall yield) was developed. Compared to hydroxymatairesinol (1) (log K' = 1.49), the derivatives (2-5) had increased lipophilicity with log K' > 3.1, as determined by a UHPLC method. Compounds 1-5 exhibited potent antioxidant properties in the same range as the standards ascorbic acid and α-tocopherol (IC = 20-25 μM) and higher than that of BHT using a DPPH radical-scavenging assay.
从枞木（Abies alba）、云杉（Picea abies）和花旗松（Pseudotsuga menziesii）的节木中提取的木脂素 7'-羟基马泰瑞醇（1），在尝试对 C-7'位羟基进行酯化反应时表现出出乎意料的反应性。为了避免导致木脂素 conidendrin（7）定量生成的快速分子内环化过程，开发了一种在温和条件下进行 7'-酯化的简单策略（三步，总收率高达 80%）。与羟基马泰瑞醇（1）（log K' = 1.49）相比，衍生物（2-5）的亲脂性增加，log K' > 3.1，这是通过 UHPLC 方法确定的。在 DPPH 自由基清除测定中，化合物 1-5 表现出与抗坏血酸和 α-生育酚（IC = 20-25 μM）标准品相当的强大抗氧化性能，且高于 BHT。
