Prinz Sonja, Ringl Alexandra, Huefner Antje, Pemp Enne, Kopp Brigitte
Department of Pharmacognosy, University of Vienna, Althanstrasse 14, A-1090 Vienna.
Chem Biodivers. 2007 Dec;4(12):2920-31. doi: 10.1002/cbdv.200790241.
In our chemotaxonomic investigation of pharmaceutically relevant Crataegus species, the qualitative and quantitative flavonoid fingerprint of Crataegus monogyna and C. pentagyna is presented. Six flavonoids were identified as vitexin-2''-O-rhamnoside (1), vitexin (2), isovitexin (3), rutin (4), hyperoside (5), and isoquercitrin (6). Besides the verification of the main compounds isoorientin (7) and orientin (8) in C. pentagyna, further four flavonoids were isolated and identified as isoorientin-2''-O-rhamnoside (9), orientin-2''-O-rhamnoside (10), isovitexin-2''-O-rhamnoside (11), and 8-methoxykaempferol-3-O-glucoside (12) by means of 1D- and 2D-NMR, MS, and UV analyses. Compound 12 was isolated for the first time from C. pentagyna. In contrast to C. pentagyna, C. monogyna samples were predominated by 4'''-acetylvitexin-2''-O-rhamnoside (13), which was missing in C. pentagyna. Hence, 13 represents an interesting compound for chemotaxonomy of C. monogyna, whereas the main flavonoids 7, 8, and 12 could be proposed as markers for C. pentagyna. The absence of 7, 8, 12, and 13 in C. laevigata offers an appropriate tool for additional differentiation from C. monogyna and C. pentagyna, and for sample identification and quality control of the three main Crataegus species used in European phytotherapy.
在我们对具有药学相关性的山楂属植物进行的化学分类学研究中，展示了山楂和五角山楂的定性和定量类黄酮指纹图谱。鉴定出六种黄酮类化合物，分别为牡荆素 -2''-O-鼠李糖苷（1）、牡荆素（2）、异牡荆素（3）、芦丁（4）、金丝桃苷（5）和异槲皮苷（6）。除了验证五角山楂中的主要化合物异荭草素（7）和荭草素（8）外，还通过一维和二维核磁共振、质谱和紫外分析分离并鉴定出另外四种黄酮类化合物，分别为异荭草素 -2''-O-鼠李糖苷（9）、荭草素 -2''-O-鼠李糖苷（10）、异牡荆素 -2''-O-鼠李糖苷（11）和8-甲氧基山奈酚 -3-O-葡萄糖苷（12）。化合物12首次从五角山楂中分离得到。与五角山楂不同，山楂样品中主要成分是4'''-乙酰基牡荆素 -2''-O-鼠李糖苷（13），而五角山楂中没有该成分。因此，13是山楂化学分类学中一种有趣的化合物，而主要黄酮类化合物7、8和12可作为五角山楂的标志物。光叶山楂中不存在7、8、12和13，这为其与山楂和五角山楂的进一步区分，以及欧洲植物疗法中使用的三种主要山楂属物种的样品鉴定和质量控制提供了合适的工具。
