核磁共振实验结合量子化学计算研究3/4/5-O-阿魏酰奎宁酸三维结构
收稿日期: 2024-04-30
网络出版日期: 2024-05-24
基金资助
中原工学院科研团队发展项目(K2022TD002);黑龙江省博士后基金项目(LBH-Z19030);河南省科技攻关项目(232102311049)
Three-Dimensional Structures of 3/4/5-O-feruloylquinic Acids by NMR Spectroscopy and Quantum Chemistry Calculation
Received date: 2024-04-30
Online published: 2024-05-24
3/4/5-O-阿魏酰奎宁酸（3/4/5-O-feruloylquinic acid, 3/4/5-O-FQA）具有抗氧化活性，对预防多种疾病和维持人体健康有益，然而其准确三维结构尚不清楚．本文采用核磁共振波谱技术，结合量子化学理论计算方法，研究了3/4/5-O-FQA分别在气相、D2O溶液和DMSO-d6溶液中的三维结构．结果表明，3-O-FQA在D2O和DMSO-d6两种溶液中的三维结构存在差异，主要表现在酯化位H-3位置处二面角τ (H3C3O1C9的不同，相差4.147°．这些结构差异导致了3-O-FQA在两种溶液中的1H 核磁共振谱图中H-3质子裂分方式不同．该工作给出了3/4/5-O-FQA的精确结构信息，能够为进一步研究其性质和应用价值提供参考和帮助．
关键词： 三维结构; 核磁共振; 量子化学计算; 化学位移; 3/4/5-O-阿魏酰奎宁酸
张佳钰 , 聂文博 , 涂朝 , 郑利敏 , 王艳 , 杨春升 . 核磁共振实验结合量子化学计算研究3/4/5-O-阿魏酰奎宁酸三维结构[J]. 波谱学杂志, 2025 , 42(1) : 47 -55 . DOI: 10.11938/cjmr20243115
3/4/5-O-feruloylquinic acids (3/4/5-O-FQA) have antioxidant activity, which is beneficial to disease prevention and human health maintenance, however, their exact 3D structures are still unknown. In the present work, the structures of 3/4/5-O-FQA in gas phase, D2O solution and DMSO-d6 solution are investigated respectively using 1H nuclear magnetic resonance (NMR) spectroscopy combined with quantum chemistry calculation. We observed a difference of 4.147° in dihedral angle τ (H3C3O1C9) on the esterification site H-3 for 3-O-FQA in D2O and DMSO-d6 solutions, which can explain the difference on 1H NMR spectra for H-3 atom of 3-O-FQA in the two solutions. This work presents the 3D structures of 3/4/5-O-FQA, offering valuable insights for further studies on their properties and potential applications.
| [1] | YUAN B, LU M, ESKRIDGE K M, et al. Extraction, identification, and quantification of antioxidant phenolics from hazelnut (Corylus avellana L.) shells[J]. Food Chem, 2018, 244(1): 7-15. |
| [2] | ZHOU X, PAK S J, LI D, et al. Bamboo shoots modulate gut microbiota, eliminate obesity in high-fat-diet-fed mice and improve lipid metabolism[J]. Foods, 2023, 12(7): 1380-1396. |
| [3] | WANG Y L, CHEN J, WANG D M, et al. A systematic review on the composition, storage, processing of bamboo shoots: Focusing the nutritional and functional benefits[J]. J Funct Foods, 2020, 71(10): 4015-4030. |
| [4] | DOKLI I, NAVARINI L, HAMER?AK Z. Syntheses of 3-, 4-, and 5-O-feruloylquinic acids[J]. Tetrahedron: Asymmetry, 2013, 24(13-14): 785-790. |
| [5] | MORISHITA H, IWAHASHI H, KIDO R. 4-O-feruloylquinic acid from green coffee beans[J]. Phytochemistry, 1986, 25(6): 1496-1497. |
| [6] | MORISHITA H, IWAHASHI H, OSAKA N, et al. Chromatographic separation and identification of naturally occurring chlorogenic acids by 1H nuclear magnetic resonance spectroscopy and mass spectrometry[J]. J Chromatogr A, 1984, 315(1): 253-260. |
| [7] | FRANK O, ZEHENTBAUER G, HOFMANN T. Bioresponse-guided decomposition of roast coffee beverage and identification of key bitter taste compounds[J]. Eur Food Res Technol, 2006, 222(5): 492-508. |
| [8] | IWAI K, KISHIMOTO N, KAKINO Y, et al. In vitro antioxidative effects and tyrosinase inhibitory activities of seven hydroxycinnamoyl derivatives in green coffee beans[J]. J Agric Food Chem, 2004, 52(15): 4893-4898. |
| [9] | PARK J B. Isolation and quantification of major chlorogenic acids in three major instant coffee brands and their potential effects on H2O2-induced mitochondrial membrane depolarization and apoptosis in PC-12 cells[J]. Food Funct, 2013, 4(11): 1632-1638. |
| [10] | ALOSO-SALCES R M, SERRA F, RENIERO F, et al. Botanical and geographical characterization of green coffee (Coffea arabica and Coffea canephora): chemometric evaluation of phenolic and methylxanthine contents[J]. J Agric Food Chem, 2009, 57(10): 4224-4235. |
| [11] | JAISWAL R, PATRAS M A, ERAVUCHIRA P J, et al. Profile and characterization of the chlorogenic acids in green Robusta coffee beans by LC-MSn: Identification of seven new classes of compounds[J]. J Agric Food Chem, 2010, 58(15): 8722-8737. |
| [12] | SPIELBAUER B, STAHL F. Impact of microarray technology in nutrition and food research[J]. Mol Nutr Food Res, 2005, 49(10): 908-917. |
| [13] | AO X L, YAN J L, LIU S L, et al. Extraction, isolation and identification of four phenolic compounds from Pleioblastus amarus shoots and their antioxidant and anti-inflammatory properties in vitro[J]. Food Chem, 2022, 374(13): 1743-1751. |
| [14] | MA C Z, CHEN P D, ZHANG L, et al. Analysis of compounds in Imperata cylindrical (Beauv. ) by UPLC-ESI-MS[J]. Chin Tradit Pat Med, 2010, 32(4): 4-7. |
| 马长振, 陈佩东, 张丽, 等. UPLC-ESI-MSn法分析白茅根中的化学成分[J]. 中成药, 2010, 32(4): 4-7. | |
| [15] | 邓安珺. 小果博落回和土蜜树化学成分研究[D]. 中国协和医科大学, 2008. |
| [16] | WOLINSKI K., HILTON J. F., and PULAY P. Efficient implementation of the gauge-independent atomic orbital method for NMR chemical shift calculations[J]. J Am Chem Soc, 1990, 112(23):8251-8260 |
| [17] | FRISCH M J, TRUCKS G W, SCHLEGEL H B, et al. Gaussian 09 revision d.01[CP]. Gaussian Inc, Wallingford, 2009. |
| [18] | MA K Y, QIAO W C, WANG X L, et al. A solid-state NMR study of dimethylamine cation-doped MAPbBr3 perovskite materialss[J]. Chinese J Magn Reson, 2020, 37(1): 67-75. |
| 马开阳, 乔文成, 王雪璐, 等. 二甲基胺阳离子掺杂甲胺铅溴钙钛矿材料的固体NMR研究[J]. 波谱学杂志, 2023, 40(1):10-21. | |
| [19] | SHEN C Z, ZHANG L L, LI X, et al. Hydrothermal crystallization of niobium oxide nanorods studied by 93Nb nuclear magnetic resonance[J]. Chinese J Magn Reson, 2023, 40(4): 376-384. |
| 申长志, 张琳琳, 李新, 等. 93Nb核磁共振研究铌酸纳米棒的水热晶化机理[J]. 波谱学杂志, 2023, 40(4): 376-384. |
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