Abstract：
Ten C-geranylated flavonoids, along with three known analogues, were isolated from the leaves of Artocarpus communis. The chemical structures of these compounds were unambiguously determined via comprehensive spectroscopic analysis, single-crystal X-ray diffraction experiments, and quantum chemical electronic circular dichroism calculations. Structurally, artocarones A-I (1-9) represent a group of unusual, highly modified C-geranylated flavonoids, in which the geranyl chain is cyclised with the ortho-hydroxy group of flavonoids to form various heterocyclic scaffolds. Notably, artocarones E and G-I (5 and 7-9) feature a 6H-benzo[c]chromene core that is hitherto undescribed in C-geranylated flavonoids. Artocarone J (10) is the first example of C-9-C-16 connected C-geranylated aurone. Meanwhile, the plausible biosynthetic pathways for these rare C-geranylated flavonoids were also proposed. Notably, compounds 1, 2, 4, 8, 11, and 12 exhibited promising in vitro inhibitory activities against respiratory syncytial virus and herpes simplex virus type 1.
摘要：
十个C-香叶黄酮,连同三个已知的类似物，是从Artocarpuscommunis的叶子中分离出来的。通过全面的光谱分析明确确定了这些化合物的化学结构，单晶X射线衍射实验，和量子化学电子圆二色性计算。在结构上,artocaronesA-I（1-9）代表一组不寻常的，高度修饰的C-香叶黄酮，其中香叶烷基链与类黄酮的邻羟基环化以形成各种杂环支架。值得注意的是,artocaronesE和G-I（5和7-9）具有6H-苯并[c]色烯核心，迄今未在C-香叶化类黄酮中描述。ArtocaroneJ（10）是C-9-C-16连接的C-香叶化金龙的第一个例子。同时,还提出了这些稀有C-香叶黄酮的合理生物合成途径。值得注意的是,化合物1、2、4、8、11和12对呼吸道合胞病毒和单纯疱疹病毒1型具有良好的体外抑制活性。
