Johan Gadolin Process Chemistry Centre, Laboratory of Organic Chemistry, Åbo Akademi University, Piispankatu 8, FIN-20500 Turku, Finland.
Molecules. 2019 Jan 9;24(2):220. doi: 10.3390/molecules24020220.
Lignans, neolignans, norlignans and norneolignans constitute a large class of phenolic natural compounds. 9-Norlignans, here defined to contain a β⁻β' bond between the two phenylpropanoid units and to lack carbon number 9 from the parent lignan structure, are the most rarely occurring compounds within this class of natural compounds. We present here an overview of the structure, occurrence and biological activity of thirty-five 9-norlignans reported in the literature to date. In addition, we report the semisynthetic preparation of sixteen 9-norlignans using the natural lignan hydroxymatairesinol obtained from spruce knots, as starting material. 9-Norlignans are shown to exist in different species and to have various biological activities, and they may therefore serve as lead compounds for example for the development of anticancer agents. Hydroxymatairesinol is shown to be a readily available starting material for the preparation of norlignans of the imperanene, vitrofolal and noralashinol family.
木脂素、新木脂素、降木脂素和降新木脂素构成了一大类酚类天然化合物。9-降木脂素，在这里被定义为两个苯丙素单元之间含有β-β'键，并且缺少母木质素结构中的 9 号碳，是该天然化合物类中最罕见的化合物。本文综述了迄今为止文献中报道的 35 种 9-降木脂素的结构、存在和生物活性。此外，我们还报告了使用从云杉节中获得的天然木质素羟马泰瑞醇作为起始原料，通过半合成方法制备了 16 种 9-降木脂素。9-降木脂素存在于不同的物种中，具有多种生物活性，因此它们可以作为先导化合物，例如用于开发抗癌药物。羟马泰瑞醇被证明是制备异戊烯基、维生素和noralashinol 家族的降木脂素的易得起始原料。
