An undescribed labdane-like diterpene with a rare spiro-β-lactone function was identified from the ethanol extract of the male cones of the coniferous tree Wollemia nobilis. This spirolabdadienolide (IUPAC name: syn-ent-8(17),13-labdadien-19,18-olid-15-oic acid methyl ester; trivial name: wollemolide), was isolated by means of traditional and high performance chromatography techniques and structurally elucidated through NMR and MS. In addition, six further known metabolites were evidenced in the extract. Wollemolide, which may be considered an additional chemotaxonomic marker, and 4'-O-methyl-scutellarein, a simple flavonoid, had not been isolated in our previous phytochemical study on the same plant organ. This demonstrates how the molecular pattern of a plant species is in continuous movement and changes with the passing of time according to the climate of the year.

中文翻译：

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来自 Wollemia nobilis 的雄性锥体，具有罕见的螺-β-内酯功能的同-ent-labdadiene 衍生物

从针叶树 Wollemia nobilis 的雄性球果的乙醇提取物中鉴定出一种具有罕见螺-β-内酯功能的未描述的拉丹丹样二萜。这种螺二烯内酯（IUPAC 名称：syn-ent-8(17),13-labdadien-19,18-olid-15-oic酸甲酯；俗名：wollemolide）通过传统和高效色谱技术分离，并通过核磁共振和质谱进行结构阐明。此外，提取物中还证实了六种其他已知代谢物。在我们之前对同一植物器官进行的植物化学研究中，Wollemolide 和 4'-O-methyl-scutellarein（一种简单的黄酮类化合物）可能被认为是一种额外的化学分类标记物。