Chinese Journal of Magnetic Resonance >
Structural Elucidation of D-Camphor and β-Cyclodextrin Inclusion Complex
Received date: 2014-06-26
Revised date: 2015-01-08
Online published: 2015-03-05
Inclusion complex of β-cyclodextrin (β-CD) and D-camphor was prepared from saturated solution with stirring. The stoichiometric ratio of the inclusion complex was found to be 1∶1, as indicated by the 1H NMR results. XRD and FTIR spectroscopy was used to probe the intermolecular interactions between D-camphor and β-CD. 1H ROESY NMR results showed that the bicyclo[2.2.1]-2-heptanone of D-camphor was located in the cavity of β-CD, and its methyl group was partially outside. Quantum chemical calculation was used to obtain minimized binding energy and optimized structure, suggesting the
presence of hydrogen bonding.
Key words： NMR; inclusion complex; β-cyclodextrin; D-camphor
ZHU Qing-ying* , HE Pei-zhi . Structural Elucidation of D-Camphor and β-Cyclodextrin Inclusion Complex[J]. Chinese Journal of Magnetic Resonance, 2015 , 32(1) : 87 -94 . DOI: 10.11938/cjmr20150110
[1] Xiong Ying(熊颖)，Wu Xue-ru(吴雪茹), Tu Xing-ming(涂兴明), et al. Progress in pharmaceutical camphor(樟脑的药学研究进展)[J]. Lab Med Clin(检验医学与临床), 2009, 6(12): 999－1 001.
[2] Xu H, Blair N T, Clapham D E. Camphor activates and str ongly desensitizes the transient receptor potential vanilloid subtype 1 channel in a vanilloid- independent mechanism[J]. J Neurosci, 2005, 25(39) : 8 924－8 928.
[3] Liu Peng(刘朋), Nie Hong-mei(聂红梅), Xiong Wei-zheng(熊维政), et al. Assay method of compound camphor cream(复方樟脑乳膏含量测试方法研究)[J]. China Journal of Chinese Medicine(中医学报), 2014, 29(188): 71－75.
[4] Huang Shao-hua(黄少华), Bai Zheng-wu(柏正武), Feng Ji-wen(冯继文), et al. Enantiomeric discrimination of D/L-10-camphoric sulfonicAcid by β-cyclodextrins studied by NMR spectroscopy(β-环糊精手性识别D/L-樟脑磺酸的NMR研究)[J]. Chinese J Magn Reson(波谱学杂志), 2009, 26(4): 457－465.
[5] Qin Dong-yan(秦冬彦), Song Hong-tao(宋洪涛), Guo Tao(郭涛), et al. Studies on the stability of borneol-β-cyclodextrin inclusion complex(冰片-β-环糊精包合物的稳定性考察)[J]. Chinese Traditional and Herbal Drugs(中草药), 2000, 31(4): 255－257.
[6] Szejtli J. Introduction and general overview of cyclodextrin chemistry[J]. Chem Rev, 1998, 98: 1 743－1 753.
[7] Liu L, Guo Q X. Novel prediction for the driving force and guest orientation in the complexation of α and β-cyclodextrin with benzene derivatives[J]. J Phys Chem B, 1999, 103, 3 461－3 467.
[8] Schneider H J, Hacket F. NMR studies of cyclodextrins and cyclodextrin complexes[J]. Chem Rev, 1998, 98: 1 755－1 785.
[9] Zhao Bing(赵兵), Li Yi-lei(李艺蕾), Li Ming(李明), et al. An NMR study of capsaicin /β-cyclodextrin complex(辣椒碱与β-环糊精包合物的核磁共振研究)[J]. Chinese J Magn Reson(波谱学杂志), 2013, 30(4): 576－584.
[10] Li Jun-fen(李俊芬), Xu Zhi-cheng(许志成), Dong Chuan(董川). Preparation and spectroscopic study on the inclusion complexes of cryptotanshinone with β-CD(隐丹参酮与环糊精包结物的制备与光谱研究)[J]. Journal of Analytical Science (分析科学学报), 2004, 20(3): 229－232.
[11] Frisch M J, Trucks G W, Schlegel H B, et al. Gaussian 03, Revision D.01, Gaussian, Inc[CP], Wallingford, CT, 2004.
[12] Betzel C, Saenger W, Hingerty B E, et al. Circular and flip-flop hydrogen bonding in. β-cyclodextrin undecahydrate: a neutron diffraction study[J]. J Am Chem Soc, 1984, 106(24): 7 545－7 557.
[13] Yan C, Xiu Z, Li X, et al. Theoretical study for quercetin/β-cyclodextrin complexes: quantum chemical calculations based on the PM3 and ONIOM2 method[J]. J Incl Phenom Macro Chem, 2007, 58(3-4): 337－344.
/
| 〈 |
|
〉 |