|
|
|
|
|
|
Study of Stereoselective Interaction Between Ginsenoside Rh2 and Serum Albumin by Spectroscopic Methods and Molecular Docking |
LI Hong1, XU Qian1, ZHENG Xiao-li1, XU Hui1*, CHEN Geng2, MENG Qing-guo1* |
1. School of Pharmacy, Key Laboratory of Molecular Pharmacology and Drug Evaluation (Yantai University), Ministry of Education, Collaborative Innovation Center of Advanced Drug Delivery System and Biotech Drugs in Universities of Shandong, Yantai University, Yantai 264005, China
2. School of Chemistry and Chemical Engineering, Yantai University, Yantai 264005, China |
|
|
Abstract Stereochemistry plays an important role in the interactions between functional bio-macromolecules and exogenous small-molecule drugs. Ginsenoside Rh2 is an effective constituent of ginseng with chirality of hydroxyl group at carbon-20, which has been found closely related to its multiple biological effects such as anti-tumor activity. However, the stereoselectivity of ginsenoside Rh2 interacting with serum albumin (SA), a vital drug carrier in the body, has been rarely reported. In the present study, interactions between SA and the C-20 eipmers of ginsenoside Rh2 were investigated under simulative physiological condition by molecular docking method and spectroscopic analyses, including UV absorption, fluorescence and synchronous fluorescence spectroscopy. Results showed that both 20S- and 20R-Rh2 could form 1∶1 type non-covalent complex with SA mainly via hydrogen bond and hydrophobic forces. According to the influence on spectra of SA, both epimers led to some increase in hydrophobicity for the light emitting residues of SA, as well as the change in micro-environment around some residues (including tyrosine and tryptophan) responsible for intrinsic fluorescence of SA, and fluorescence quenching mainly by a static mode. However, 20S-Rh2 displayed relatively larger binding constant and free energy in contrast with 20R-Rh2, suggesting stereoselective characteristics of the eipmers. The stereo-selectivity of ginsenoside Rh2 interacted with serum albumin may be related with stereochemistry of C-20.
|
Received: 2018-01-24
Accepted: 2018-05-06
|
|
Corresponding Authors:
XU Hui, MENG Qing-guo
E-mail: xuhui33@sina.com; qinggmeng@163.com
|
|
[1] Nakagawa T, Ubukata T, Yokoyama Y. Journal of Photochemistry and Photobiology C, 2017, 5(2): 22.
[2] Chai T, Cui F, Mu X, et al. Environmental Pollution, 2016, 3(15): 66.
[3] WU Yun-jian, CUI Ying-lu, ZHENG Qing-chuan, et al(吴云剑, 崔颖璐, 郑清川,等). Chemical Journal of Chinese Universities(高等学校化学学报), 2014, 35(12): 2605.
[4] Rulcova A, Prokopova I, Krausova L, et al. Journal of Chromatography A, 2015, 1377(6): 106.
[5] Zhang J, Zhou F, Niu F, et al. PLoS ONE, 2012, 7(4): 57.
[6] Motealleh A, Hermes H, Jose J, et al. Biology and Medicine, 2018, 14(2): 247.
[7] CAO Man, ZHANG Jie, ZHAO Yang, et al(曹 满, 张 洁, 赵 阳,等). World Science and Technology/Modernization of Traditional Chinese Medicine and Materia Medica(世界科学技术—中医药现代化), 2012, 14(6): 2205.
[8] Yang J, Li X, Sun T, et al. Steroids, 2016, 106(3): 26.
[9] Lv Q, Rong N, Liu L J, et al. Planta Medica, 2016, 82(8): 705.
[10] Mi J, Kwan C, Hwa Y. Journal of Pharmacopuncture, 2016, 19(3): 213.
[11] Zhang J, Zhou F, Niu F, et al. Plos One, 2012, 7(4): 57.
[12] Kim D, Yu F Z, Ji S K, et al. Drug Metabolism & Pharmacokinetics, 2017, 32(1): S55.
[13] Kim D, Zheng Y F, Min J M, et al. Toxicology Letters, 2016, 59 (2): 1.
[14] CAO Tuan-wu, ZHOU Kun, HUANG Wen-bing, et al. (曹团武, 周 坤, 黄文兵,等). Analytical Chemistry(分析化学), 2017, 45(5): 700.
[15] Sastry G M, Adzhigirey M, Day T, et al. Journal of Computer-Aided Molecular Design, 2013, 27(2): 221.
[16] Park K, Cho A E. Journal of Ginseng Research, 2017, 41(4): 534.
[17] Subhani S, Jamil K. Biomedicine & Pharmacotherapy, 2015, 73(3): 65.
[18] Lin Y J, Li Y, Song Z J, et al. J Ginseng Res, 2017, 41(3): 330.
[19] ClaraRàfols. Amézqueta S. Journal of Pharmaceutical and Biomedical Analysis, 2018, 150(2): 452.
[20] WANG Yi-run, HUANG Fang, LIU Ying(王艺润, 黄 芳, 刘 颖). Spectroscopy and Spectral Analysis(光谱学与光谱分析), 2017, 37(4): 1205.
[21] WANG Yong-gang, YANG Guang-rui, MA Xue-qing, et al(王永刚, 杨光瑞, 马雪青,等). Spectroscopy and Spectral Analysis(光谱学与光谱分析), 2017, 37(8): 2474.
[22] WANG Yi-lun, FANG Qing, GUO Chen-hui, et al(王一伦, 方 晴, 郭晨辉,等). Spectroscopy and Spectral Analysis(光谱学与光谱分析), 2016, 36(10): 3414.
|
[1] |
ZHANG Xiao-dan1, 2, LIU Li-li1*, YU Ying1, CHENG Wei-wei1, XU Bao-cheng1, HE Jia-liang1, CHEN Shu-xing1, 2. Activation of Epigallocatechin Gallate on Alcohol Dehydrogenase:
Multispectroscopy and Molecular Docking Methods[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2023, 43(11): 3622-3628. |
[2] |
YU De-guan1, CHEN Xu-lei1, WENG Yue-yue2, LIAO Ying-yi3, WANG Chao-jie4*. Computational Analysis of Structural Characteristics and Spectral
Properties of the Non-Prodrug-Type Third-Generation
Cephalosporins[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2023, 43(10): 3211-3222. |
[3] |
YANG Jing1, LI Li1, LIANG Jian-dan1, HUANG Shan1, SU Wei1, WEI Ya-shu2, WEI Liang1*, XIAO Qi1*. Study on the Interaction Mechanism Between Thiosemicarbazide Aryl Ruthenium Complexes and Human Serum Albumin[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2023, 43(09): 2761-2767. |
[4] |
ZHANG Ye-li1, 2, CHENG Jian-wei3, DONG Xiao-ting2, BIAN Liu-jiao2*. Structural Insight Into Interaction Between Imipenem and Metal β-Lactamase SMB-1 by Spectroscopic Analysis and Molecular Docking[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2023, 43(07): 2287-2293. |
[5] |
REN Li-lei, PENG Yu-ling, WANG Shu-jun*, ZHANG Cheng-gen, CHEN Yu, WANG Xin-tong, MENG Xiao-ning. Fluorescence Spectroscopy for Studies on the Interaction Between Three Metalloporphyrins With Human Serum Albumin[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2023, 43(03): 806-813. |
[6] |
HOU Qian-yi1, 2, DONG Zhuang-zhuang1, 2, YUAN Hong-xia1, 2*, LI Qing-shan1, 2*. A Study of the Mechanism of Binding Between Quercetin and CAV-1 Based on Molecular Simulation, Bio-Layer Interferometry and
Multi-Spectroscopy Methods[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2023, 43(03): 890-896. |
[7] |
LI Jin-zhi1, LIU Chang-jin1, 4*, SHE Zhi-yu2, ZHOU Biao2, XIE Zhi-yong2, ZHANG Jun-bing3, JIANG Shen-hua2, 4*. Antiglycation Activity on LDL of Clove Essential Oil and the Interaction of Its Most Abundant Component—Eugenol With Bovine Serum Albumin[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2023, 43(01): 324-332. |
[8] |
XU Xiao-qing1, ZHOU Qian1, SUN Jian-hua1, SUN Li-xia1, FENG Xue-zhen1, 2, XU Yong-fang1, TONG Zhang-fa1, LIAO Dan-kui1*. Study on the Inhibition Mechanism of Angiotensin Conversion Enzyme
Inhibitor Peptide Leu-Lys-Pro (LKP)[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2022, 42(07): 2107-2112. |
[9] |
WANG Jun1, WANG Zhou-li2, CHENG Jing-jing1. Interaction Between Tartrazine and Bovine Serum Albumin Using Multispectral Method and Molecular Docking[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2022, 42(03): 904-909. |
[10] |
WANG Xiao-xia1,3*, WU Hao1, NIE Zhi-hua2, MA Li-tong1,3*, CUI Jin-long1, SAI Hua-zheng1, CHENG Jian-guo1. Study on the Interaction Between Fulvic Acid and Bovine Serum Albumin by Multispectral and Molecular Docking[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2021, 41(09): 2904-2910. |
[11] |
ZHANG Chuan-ying1, PENG Xin1*, RAO Heng-jun2, QI Wei2, SU Rong-xin2, HE Zhi-min2. Spectroscopic Studies on the Interaction Between Salvianolic Acid B and Bovine Serum Albumin[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2021, 41(06): 1701-1707. |
[12] |
TUO Xun1, SONG Ji-min1, FU Hao2, LÜ Xiao-lan1*. Study on Interaction Between Hexabromocyclododecane and Bovine Serum Albumin by Spectroscopy and Computer Simulation Methods[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2021, 41(05): 1487-1492. |
[13] |
HU Jing-jing, TONG Chang-lun*. Study on the Interaction Between Carbon Quantum Dots and Human Serum Albumin by Spectroscopic Methods[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2021, 41(04): 1107-1113. |
[14] |
LI Xue1, WANG Li1, LIU Guang-xian1*, TU Zong-cai2. Effect of Urea on Glycosylation of BSA Based on Spectral Techniques[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2021, 41(02): 478-483. |
[15] |
LI Xing-xing, ZHANG Xiang, HUANG Xue-song*. Interaction Between Three Sulfur-Containing Amino Acids in Garlic and Bovine Serum Albumin Determined by Fluorescence Spectrometry[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2020, 40(11): 3483-3488. |
|
|
|
|