Phytochemical analysis of methanol extracts of Ginkgo biloba leaves resulted in the isolation of a novel diarylpentanoid, ginkgobilol (1) and a known diarylpentanoid analog (2). The structure of the new compound was elucidated by analyzing NMR spectroscopic data and HR-ESIMS, and the absolute configuration was determined using gauge-including atomic orbital NMR chemical shift calculations, followed by DP4+ analysis and specific rotation value. Diarylpentanoids comprise two aromatic rings linked by a five-carbon bridge; these are relatively unique examples in natural products. To the best of our knowledge, the present study is the first to report the presence of diarylpentanoids in G. biloba. Compound 2 increased alkaline phosphatase (ALP) production in C3H10T1/2, a murine mesenchymal stem cell line, in a dose-dependent manner. The promotion of osteogenic differentiation by the active compound 2 mediated by induction of transcriptional ALP and osteopontin (OPN) gene expression was confirmed using quantitative real time polymerase chain reaction, thus indicating its remarkable bone formation activity.

银杏叶甲醇提取物的植物化学分析导致分离出一种新型的二芳基戊烷，银杏酚（1）和一种已知的二芳基戊烷类似物（2）。通过分析NMR光谱数据和HR-ESIMS阐明了新化合物的结构，并使用包括轨距在内的原子轨道NMR化学位移计算，随后的DP4 +分析和比旋值确定了绝对构型。二芳基戊烷包括由五个碳桥连接的两个芳环；这些是天然产品中相对独特的例子。据我们所知，本研究是第一个报道银杏叶中存在二芳基戊烷类化合物的研究。化合物2C3H10T1 / 2（一种小鼠​​间充质干细胞系）以剂量依赖性方式增加了碱性磷酸酶（ALP）的产生。使用定量实时聚合酶链反应证实了由转录ALP和骨桥蛋白（OPN）基因表达的诱导介导的活性化合物2促进成骨细胞分化，从而表明其显着的骨形成活性。