Study on Fluorescence Properties of Flavanone and Its Hydroxyl Derivatives
LI Wen-hong1, 2, 3, CAO Jin-jin2, LU Rui2, CHE Cui-xia2, WEI Yong-ju1, 2*
1. College of Life Science, Hebei Normal University, Shijiazhuang 050024, China 2. College of Chemistry and Material Science，Hebei Normal University，Shijiazhuang 050024, China 3. Department of Environmental and Chemical Engineering, Hebei College of Industry and Technology, Shijiazhuang 050091, China
Abstract：Flavanone derivatives are important active ingredients of natural medicine, so the synthesis of these compounds is one of the research hotspots of organic synthesis. Nevertheless, there is little research on fluorescence properties of these compounds up to now. Fluorescence properties of flavanone and 6 kinds of hydroxyl derivatives are studied in this paper. It is found that aqueous solutions of flavanone (FV), 7-hydroxyflavanone (7HF) and 6-hydroxyflavanone (6HF) have fluorescence, but aqueous solutions of 2’-hydroxyflavanone (2’HF), 4’-hydroxyflavanone (4’HF), naringenin and pinocembrin basically have no fluorescence. In three dimensional fluorescence spectra, excitation wavelengths λex of FV are located at 235, 265 and 340 nm, emission wavelength λem is at 386 nm; λex of 7HF are at 230, 276 and 315 nm, λem is at 391 nm; λex of 6HF are at 260 and 356 nm, em is at 482 nm. Influences of pH on fluorescence of FV, 7HF and 6HF are studied, and the reasons of pH affects on fluorescence are discussed from the viewpoint of molecular structure. The UV-absorption spectra of 7HF and 6HF at different pH are studied, and the proton ionization constants (pKa) of 7HF and 6HF are determined respectively to be 7.26±0.05 and 9.90±0.02, by a pH-absorption method. Influences of solvent (methanol) on fluorescence of FV, 7HF and 6HF are studied, and find that the fluorescence of FV and 7HF in methanol are weaker than that in water, but the fluorescence of 6HF in methanol is much stronger. In ordered media (SDS, CTAB and β-CD), fluorescence of FV and 7HF decreased than that in water, but the fluorescence of 6HF enhanced in the media of β-CD or CTAB. Using quinine sulfate or L-tryptophane as reference, fluorescence quantum yields of FV and 7HF aqueous solutions are measured to be 0.057 and 0.012, respectively; fluorescence quantum yields of 6HF in methanol or in aqueous solution containing 1.62 mg·mL-1 β-CD are measured to be 0.064 or 0.012, respectively.
李文红1,2,3，曹津津2，卢 蕊2，车翠霞2，魏永巨1,2* . 黄烷酮及其羟基衍生物的荧光性质研究 [J]. 光谱学与光谱分析, 2016, 36(04): 1007-1012.
LI Wen-hong1, 2, 3, CAO Jin-jin2, LU Rui2, CHE Cui-xia2, WEI Yong-ju1, 2* . Study on Fluorescence Properties of Flavanone and Its Hydroxyl Derivatives. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2016, 36(04): 1007-1012.
[1] Moorthy N S H N, Singh R J, Singh H P, et al. Chem. Pharm. Bull., 2006, 54(10): 1384. [2] Hu Ke, Yang Yu, Tu Qiuyun, et al. European Journal of Pharmacology, 2013, 721: 96. [3] Ketabforoosh S H M E, Kheirollahi A, Safavi M, et al. Arch. Pharm. Chem. Life Sci., 2014, 347: 853. [4] Shin S Y, Kim J H, Lee J H, et al. Mol. Nutr. Food Res., 2012, 56, 761. [5] Parhiz H, Roohbakhsh A, Soltani F, et al. Phytotherapy Research，2015, 29: 323. [6] Zhao Donghai, Sui Xin, Qu Youle, et al. Asian J. Chem., 2011, 23(3): 1129. [7] Zhao Gang, Zhang Wen, Li Li, et al. Molecules, 2014, 19: 15786. [8] Javed H, Vaibhav K, Ahmed M E, et al. Journal of the Neurological Sciences, 2015, 348: 51. [9] Yousuf S, Radhika D, Enoch I V M V, et al. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2012, 98: 405. [10] Yang Zhihong, Liu Rui, Li Xiaoxiu, et al. J. Pharm. Biomed. Anal., 2009, 49: 1277. [11] ZHANG Chun-juan, MENG Zhi-fen, GUO Xue-feng, et al(张春娟，孟志芬，郭雪峰，等). Spectroscopy and Spectral Analysis(光谱学与光谱分析), 2014, 34(9): 2568. [12] Xiong Xin, Jiang Junjie, Duan Jingli, et al. Journal of Chromatographic Science, 2014, 52: 654. [13] XU Jin-gou, WANG Zun-ben (许金钩，王尊本). Fluorimetry, 3rd ed(荧光分析法，第3版). Beijing: Science Press(北京: 科学出版社), 2006. 12. [14] WU Li-jun, LOU Hong-xiang, ZHOU Jing(吴立军，娄红祥，周 晶). Natural Pharmaceutical Chemistry, 6th ed.(天然药物化学，第6版). Beijing：People’s Medical Publishing House(北京：人民卫生出版社)，2011. 197.
