State Key Laboratory of Magnetic Resonance and Atomic and Molecular Physics, Wuhan Centre for Magnetic Resonance, Wuhan Institute of Physics and Mathematics, Chinese Academy of Sciences, Wuhan 430071, PR China.
J Agric Food Chem. 2012 Jan 11;60(1):129-35. doi: 10.1021/jf204406u. Epub 2011 Dec 29.
Identification of new compounds especially those with new skeletons from plant kingdom has long been a vital aspect for understanding phytochemistry, plant metabolisms and discovering new bioactive compounds. In this study, we identified and isolated three novel polyphenolic compounds, origanine A-C, from a well-researched plant Origanum vulgare L. using the hyphenated LC-DAD-SPE-NMR/MS methods. Based on the combined information from UV-visible, accurate mass and 2D NMR spectra together with computational calculations, we found that these compounds all had a novel skeleton of cyclohexenetetracarboxylic acids attached with some well-known bioactive moieties including 3,4-dihydroxyphenyl, 4-(β-d-glucopyranosyloxy)benzyl alcohol (gastrodin), and 3-(3,4-dihydroxyphenyl)lactic acid (danshensu) residues. These findings provided crucial information to fill the gaps in our knowledge in terms of the plant secondary metabolism. This study also indicated the necessity for further research in plant secondary metabolism for even well-studied plants and demonstrated the powerfulness of the hyphenated LC-DAD-SPE-NMR/MS methods for comprehensive analysis of plant metabolites in particular for discovering new natural compounds.
从植物王国中鉴定新的化合物，特别是具有新骨架的化合物，一直是理解植物化学、植物代谢和发现新生物活性化合物的重要方面。在这项研究中，我们使用 LC-DAD-SPE-NMR/MS 方法从经过充分研究的植物牛至（Origanum vulgare L.）中鉴定和分离出三种新型多酚化合物，原苷 A-C。基于紫外可见、精确质量和二维 NMR 光谱以及计算计算的综合信息，我们发现这些化合物都具有环己四羧酸的新型骨架，连接着一些众所周知的生物活性部分，包括 3,4-二羟基苯基、4-(β-d-吡喃葡萄糖基氧基)苄醇（天麻素）和 3-(3,4-二羟基苯基)乳酸（丹酚酸）残基。这些发现为填补我们在植物次生代谢方面的知识空白提供了关键信息。该研究还表明，即使是研究充分的植物，也有必要进一步研究植物次生代谢，并展示了 LC-DAD-SPE-NMR/MS 方法在全面分析植物代谢物，特别是发现新天然化合物方面的强大功能。
