Venditti Alessandro, Frezza Claudio, Sciubba Fabio, Foddai Sebastiano, Serafini Mauro, Bianco Armandodoriano
Dipartimento di Chimica, Università di Roma "La Sapienza", Piazzale Aldo Moro 5, IT-00185, Roma.
Dipartimento di Biologia Ambientale, Università di Roma "La Sapienza", Piazzale Aldo Moro 5, IT-00185, Roma.
Chem Biodivers. 2017 Mar;14(3). doi: 10.1002/cbdv.201600332. Epub 2017 Mar 11.
The analysis of metabolites contained in the male cones of Wollemia nobilis was investigated for the first time in this study. Several diterpenoids of chemosystematic relevance were recognized for the first time from the genus and/or from the Araucariaceae family, namely isocupressic acid (1), acetyl-isocupressic acid (2), methyl (E)-communate (3) and sandaracopimaric acid (4). All these terpenoids are also endowed with interesting biological activities and may play a primary role in the self defence toward herbivores. The presence of a new norlabdane (norlabda-8(16)-12-dien-14,17-diol) trivially named as wollemol (5) was also recognized. Norditerpenes are scarcely distributed in Plant Kingdom and in particular in Gymnosperms and this aspect was discussed. The structure of 5 was determined by extensive NMR analysis employing mono- and bidimensional experiments. The 7-4‴-dimethoxyagathisflavone (6), a biflavonoid already recognized in Araucariaceae and W. nobilis, was also isolated from male cones together with shikimic acid (7), a biogenetic precursor of polyphenolic compounds, besides carbohydrates such as glucose (8) and saccharose (9), and arginine (10) a quite common amino acid.
本研究首次对诺和诺德松雄球果中所含代谢物进行了分析。首次从该属和/或南洋杉科中鉴定出几种具有化学分类学意义的二萜类化合物，即异柏酸（1）、乙酰异柏酸（2）、（E）-Communic酸甲酯（3）和山达海松酸（4）。所有这些萜类化合物还具有有趣的生物活性，可能在对食草动物的自我防御中起主要作用。还鉴定出一种新的降贝壳杉烷（降贝壳杉-8(16)-12-二烯-14,17-二醇），简称为沃勒醇（5）。去甲二萜在植物界，特别是裸子植物中分布稀少，并对此进行了讨论。化合物5的结构通过使用一维和二维实验的广泛核磁共振分析确定。7-4‴-二甲氧基贝壳杉黄酮（6）是一种已在南洋杉科和诺和诺德松中鉴定出的双黄酮，除了葡萄糖（8）和蔗糖（9）等碳水化合物以及相当常见的氨基酸精氨酸（10）外，还从雄球果中分离出了莽草酸（7），它是多酚类化合物的生物合成前体。
