光谱学与光谱分析 |
|
|
|
|
|
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.
|
Received: 2015-07-26
Accepted: 2015-11-18
|
|
Corresponding Authors:
WEI Yong-ju
E-mail: weiyju@126.com
|
|
[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.
|
[1] |
LEI Hong-jun1, YANG Guang1, PAN Hong-wei1*, WANG Yi-fei1, YI Jun2, WANG Ke-ke2, WANG Guo-hao2, TONG Wen-bin1, SHI Li-li1. Influence of Hydrochemical Ions on Three-Dimensional Fluorescence
Spectrum of Dissolved Organic Matter in the Water Environment
and the Proposed Classification Pretreatment Method[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2024, 44(01): 134-140. |
[2] |
XIA Ming-ming1, 2, LIU Jia3, WU Meng1, 2, FAN Jian-bo1, 2, LIU Xiao-li1, 2, CHEN Ling1, 2, MA Xin-ling1, 2, LI Zhong-pei1, 2, LIU Ming1, 2*. Three Dimensional Fluorescence Characteristics of Soluble Organic Matter From Different Straw Decomposition Products Treated With Calcium Containing Additives[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2024, 44(01): 118-124. |
[3] |
GU Yi-lu1, 2,PEI Jing-cheng1, 2*,ZHANG Yu-hui1, 2,YIN Xi-yan1, 2,YU Min-da1, 2, LAI Xiao-jing1, 2. Gemological and Spectral Characterization of Yellowish Green Apatite From Mexico[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2024, 44(01): 181-187. |
[4] |
SONG Yi-ming1, 2, SHEN Jian1, 2, LIU Chuan-yang1, 2, XIONG Qiu-ran1, 2, CHENG Cheng1, 2, CHAI Yi-di2, WANG Shi-feng2,WU Jing1, 2*. Fluorescence Quantum Yield and Fluorescence Lifetime of Indole, 3-Methylindole and L-Tryptophan[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2023, 43(12): 3758-3762. |
[5] |
YANG Ke-li1, 2, PENG Jiao-yu1, 2, DONG Ya-ping1, 2*, LIU Xin1, 2, LI Wu1, 3, LIU Hai-ning1, 3. Spectroscopic Characterization of Dissolved Organic Matter Isolated From Solar Pond[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2023, 43(12): 3775-3780. |
[6] |
XUE Fang-jia, YU Jie*, YIN Hang, XIA Qi-yu, SHI Jie-gen, HOU Di-bo, HUANG Ping-jie, ZHANG Guang-xin. A Time Series Double Threshold Method for Pollution Events Detection in Drinking Water Using Three-Dimensional Fluorescence Spectroscopy[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2023, 43(10): 3081-3088. |
[7] |
JIA Yu-ge1, YANG Ming-xing1, 2*, YOU Bo-ya1, YU Ke-ye1. Gemological and Spectroscopic Identification Characteristics of Frozen Jelly-Filled Turquoise and Its Raw Material[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2023, 43(09): 2974-2982. |
[8] |
YANG Xin1, 2, XIA Min1, 2, YE Yin1, 2*, WANG Jing1, 2. Spatiotemporal Distribution Characteristics of Dissolved Organic Matter Spectrum in the Agricultural Watershed of Dianbu River[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2023, 43(09): 2983-2988. |
[9] |
ZHU Yan-ping1, CUI Chuan-jin1*, CHENG Peng-fei1, 2, PAN Jin-yan1, SU Hao1, 2, ZHANG Yi1. Measurement of Oil Pollutants by Three-Dimensional Fluorescence
Spectroscopy Combined With BP Neural Network and SWATLD[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2023, 43(08): 2467-2475. |
[10] |
QIU Cun-pu1, 2, TANG Xiao-xue2, WEN Xi-xian4, MA Xin-ling2, 3, XIA Ming-ming2, 3, LI Zhong-pei2, 3, WU Meng2, 3, LI Gui-long2, 3, LIU Kai2, 3, LIU Kai-li4, LIU Ming2, 3*. Effects of Calcium Salts on the Decomposition Process of Straw and the Characteristics of Three-Dimensional Excitation-Emission Matrices of the Dissolved Organic Matter in Decomposition Products[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2023, 43(07): 2301-2307. |
[11] |
SHI Chuan-qi1, LI Yan2, HU Yu3, YU Shao-peng1*, JIN Liang2, CHEN Mei-ru1. Fluorescence Spectral Characteristics of Soil Dissolved Organic Matter in the River Wetland of Northern Cold Region, China[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2023, 43(05): 1517-1523. |
[12] |
LI Yuan-jing1, 2, CHEN Cai-yun-fei1, 2, LI Li-ping1, 2*. Spectroscopy Study of γ-Ray Irradiated Gray Akoya Pearls[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2023, 43(04): 1056-1062. |
[13] |
LIU Xia-yan1, CAO Hao-xuan1, MIAO Chuang-he1, LI Li-jun2, ZHOU Hu1, LÜ Yi-zhong1*. Three-Dimensional Fluorescence Spectra of Dissolved Organic Matter in Fluvo-Aquic Soil Profile Under Long-Term Composting Treatment[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2023, 43(03): 674-684. |
[14] |
LÜ Yang1, PEI Jing-cheng1*, ZHANG Yu-yang2. Chemical Composition and Spectra Characteristics of Hydrothermal Synthetic Sapphire[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2022, 42(11): 3546-3551. |
[15] |
ZHANG Yong-bin1, ZHU Dan-dan1, CHEN Ying1*, LIU Zhe1, DUAN Wei-liang1, LI Shao-hua2. Wavelength Selection Method of Algal Fluorescence Spectrum Based on Convex Point Extraction From Feature Region[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2022, 42(10): 3031-3038. |
|
|
|
|