槐果碱与<i>β</i>-环糊精及其衍生物的包合行为研究

引用本文: 古捷, 杨俊丽, 鲁佳佳, 高振杰, 杨举, 苏丽娇, 陶欣, 杨丽, 杨丽娟. 槐果碱与β-环糊精及其衍生物的包合行为研究[J]. 分析化学, 2022, 50(5): 781-790. doi: 10.19756/j.issn.0253-3820.210785 shu

Citation: GU Jie, YANG Jun-li, LU Jia-jia, GAO Zhen-jie, YANG Ju, SU Li-Jiao, TAO Xin, YANG Li, YANG Li-Juan. Study on Inclusion Behavior of Sophocarpine with β-Cyclodextrin and Its Derivatives[J]. Chinese Journal of Analytical Chemistry, 2022, 50(5): 781-790. doi: 10.19756/j.issn.0253-3820.210785 shu

槐果碱与β-环糊精及其衍生物的包合行为研究

云南民族大学化学与环境学院, 云南省高校智能超分子化学重点实验室, 生物基材料绿色制备技术国家地方联合工程中心, 昆明 650500

通讯作者: 杨丽,E-mail:379090920@qq.com; 杨丽娟,E-mail:yangljyang@sina.com

基金项目:
国家自然科学基金项目（No.21762051）、云南省高校有机功能分子及材料科技创新团队项目和云南省教育厅科学研究基金项目（No.2020J0315）资助。

摘要: 以槐果碱（SOP）为客体，β-环糊精（β-CD）、羟丙基-β-环糊精（HP-β-CD）、三甲基-β-环糊精（TM-β-CD）、单-（6-乙二胺基-6-去氧）-β-环糊精（2N-β-CD）和单-（6-二乙烯三胺-6-去氧）-β-环糊精（3N-β-CD）为主体，采用饱和溶液法制备了5种主-客体包合物。通过一维和二维核磁共振（¹H NMR、2D NMR）、紫外-可见吸收光谱（UV-Vis）、X-射线粉末衍射（XRD）和扫描电镜（SEM）等分析方法对主-客体包合物进行了表征。结果表明，SOP与5种环糊精的主-客体包合比均为1∶1；包合物形成后，SOP的水溶性和稳定性均明显提高，并且包合物在酸性条件下更稳定。核磁共振分析结果表明，SOP的D环从CDs的小口端进入其空腔，而SOP的C环则贯穿在CDs的空腔内。

关键词:

English

Study on Inclusion Behavior of Sophocarpine with β-Cyclodextrin and Its Derivatives

Key Laboratory of Intelligent Supramolecular Chemistry at the University of Yunnan Province, National and Local Joint Engineering Research Center for Green Preparation Technology of Biobased Materials, School of Chemistry&Environment, Yunnan Minzu University, Kunming 650500, China

Corresponding author: YANG Li, ; YANG Li-Juan,

Received Date: 11 October 2021
Revised Date: 31 December 2021
Fund Project:
Supported by the National Natural Science Foundation of China (No.21762051), the Program for Innovative Research Team (in Science and Technology) in University of Yunnan Province and Yunnan Provincial Department of Education Science Research Fund Project (No.2020J0315).

Abstract: By using sophocarpine (SOP) as the guest, and β-cyclodextrin (β-CD), hydroxypropyl-β-cyclodextrin (HP-β-CD), trimethyl-β-cyclodextrin (TM-β-CD), mono-(6-ethanediamine-6- deoxy)-β-cyclodextrin (2N-β-CD) and mono-(6-diethylenetriamine-6- deoxy)-β-cyclodextrin (3N-β-CD) as the host, five host-guest inclusions were prepared by the saturated solution method. The host-guest inclusion complexes were characterized by one-dimensional and two-dimensional nuclear magnetic resonance (¹H NMR, 2D NMR), ultraviolet-visible spectroscopy (UV-Vis), X-ray powder diffraction (XRD) and scanning electron microscopy (SEM). The results showed that the host-guest inclusion ratios of the SOP to the five cyclodextrins were all 1:1. After the formation of inclusion complexes, the water solubility and stability of SOP were obviously increased, and the inclusion compounds were more stable under acidic conditions. Nuclear magnetic resonance analysis showed that the D ring of SOP entered its cavity from the narrow side of the CDs, while the C ring of SOP penetrated the cavity of CDs.

Key words:

1. [1]
  LU Y, XU D, LIU J Y, GU L N. Int. Immunopharmacol., 2019, 70:180-186.LU Y, XU D, LIU J Y, GU L N. Int. Immunopharmacol., 2019, 70:180-186.
2. [2]
  DENG X X, WANG R Z, WU X L, GAO Q X, HAN L, GAO X J, ZHAO S P, CHEN W B, ZHOU R G, LI Z Y, BAI C G. J. Ethnopharmacol., 2019, 248:112172.DENG X X, WANG R Z, WU X L, GAO Q X, HAN L, GAO X J, ZHAO S P, CHEN W B, ZHOU R G, LI Z Y, BAI C G. J. Ethnopharmacol., 2019, 248:112172.
3. [3]
  ZHI W B, DU X, LI Y, WANG C L, SUN T T, ZONG S Y, LIU Q Q, HU K, LIU Y, ZHANG H. Int. Immunopharmacol., 2021, 96:107348.ZHI W B, DU X, LI Y, WANG C L, SUN T T, ZONG S Y, LIU Q Q, HU K, LIU Y, ZHANG H. Int. Immunopharmacol., 2021, 96:107348.
4. [4]
  ZOU F, WANG L, LIU H, WANG W, HU L L, XIONG X Y, WU L J, SHEN Y F, YANG R Q. Front. Pharmacol., 2019, 10:1219.ZOU F, WANG L, LIU H, WANG W, HU L L, XIONG X Y, WU L J, SHEN Y F, YANG R Q. Front. Pharmacol., 2019, 10:1219.
5. [5]
  SUN X T, YANG Y L, LIU T, HUANG H, KUANG Y, CHEN L. J. Ethnopharmacol., 2021, 273:113998.SUN X T, YANG Y L, LIU T, HUANG H, KUANG Y, CHEN L. J. Ethnopharmacol., 2021, 273:113998.
6. [6]
  MA Q H, REN M Y, LUO J P. J. Ethnopharmacol., 2021, 264:112800.MA Q H, REN M Y, LUO J P. J. Ethnopharmacol., 2021, 264:112800.
7. [7]
  LIU W, ZHANG B L, CHEN G, WU W J, ZHOU L, SHI Y, ZENG Q, LI Y Q, SUN Y W, DENG X M, WANG F. Mol. Ther., 2017, 25(9):2129-2139.LIU W, ZHANG B L, CHEN G, WU W J, ZHOU L, SHI Y, ZENG Q, LI Y Q, SUN Y W, DENG X M, WANG F. Mol. Ther., 2017, 25(9):2129-2139.
8. [8]
  WANG Q, XU J N, LI X, ZHANG D W, HAN Y, ZHANG X. J. Sep. Sci., 2017, 40(13):2688-2693.WANG Q, XU J N, LI X, ZHANG D W, HAN Y, ZHANG X. J. Sep. Sci., 2017, 40(13):2688-2693.
9. [9]
  ZHANG P P, WANG P Q, QIAO C P, ZHANG Q. Cancer. Lett., 2016, 376(1):95-103.ZHANG P P, WANG P Q, QIAO C P, ZHANG Q. Cancer. Lett., 2016, 376(1):95-103.
10. [10]
  WANG Q L, WANG T, ZHU L, HE N N, DUAN C Y, DENG W L, ZHANG H P, ZHANG X T. Biol. Pharm. Bull., 2019:42(11):1830-1838.WANG Q L, WANG T, ZHU L, HE N N, DUAN C Y, DENG W L, ZHANG H P, ZHANG X T. Biol. Pharm. Bull., 2019:42(11):1830-1838.
11. [11]
  MA Hu-Qiang, MU Jun, LIU Yang, DING Teng, TIAN Huan, WANG Chun-Liu, LI Ye, LIU Feng. Northwest Pharm. J., 2019, 34(1):84-87. 马虎强, 穆珺, 刘洋, 丁腾, 田欢, 王春柳, 李晔, 刘峰. 西北药学杂志, 2019, 34(1):84-87.
12. [12]
  LIU Z J, YE L, XI J N, WANG J, FENG Z G. Prog. Polym. Sci., 2021, 118:101408.LIU Z J, YE L, XI J N, WANG J, FENG Z G. Prog. Polym. Sci., 2021, 118:101408.
13. [13]
  ZHOU J Y, XU H A, TONG Z Z, YANG Y H, JIANG G H. Sci. Eng. Compos. Mater., 2018, 89(8):237-244.ZHOU J Y, XU H A, TONG Z Z, YANG Y H, JIANG G H. Sci. Eng. Compos. Mater., 2018, 89(8):237-244.
14. [14]
  YANG Yun-Han, BAO Qiu-Lian, GU Jie, GAO Zhen-Jie, LU Jia-Jia, YANG Ju, YANG Li-Juan. Chin. J. Anal. Chem., 2021, 49(5):768-778. 杨云汉, 保秋连, 古捷, 高振杰, 鲁佳佳, 杨举, 杨丽娟. 分析化学, 2021, 49(5):768-778.
15. [15]
  MOHAMADHOSEINI M, MOHAMADNIA Z. Coord. Chem. Rev., 2020, 432(4):213711.MOHAMADHOSEINI M, MOHAMADNIA Z. Coord. Chem. Rev., 2020, 432(4):213711.
16. [16]
  DU Yao, ZHOU Shu-Ya, YANG Yun-Han, YANG Jun-Li, CHEN Wen, YANG Li-Juan. Chin. J. Anal. Chem., 2019, 47(3):371-379. 杜瑶, 周树娅, 杨云汉, 杨俊丽, 陈文, 杨丽娟. 分析化学, 2019, 47(3):371-379.
17. [17]
  ZHAO Fang, ZHAO Xue-Qiu, CHANG Qing, WANG Shu-Hui, DU Yao, YANG Li-Juan. Chin. J. Anal. Chem., 2017, 45(10):1547-1555. 赵芳, 赵雪秋, 常清, 王淑慧, 杜瑶, 杨丽娟. 分析化学, 2017, 45(10):1547-1555.
18. [18]
  ZHAO Fang, YANG Yun-Han, ZHAO Xue-Qiu, YANG Jun-Li, YANG Li, YE Yan-Qing, CHEN Wen, YANG Li-Juan. Chin. Tradit. Herbal Drugs, 2018, 49(15):3609-3618. 赵芳, 杨云汉, 赵雪秋, 杨俊丽, 杨丽, 叶艳青, 陈文, 杨丽娟. 中草药, 2018, 49(15):3609-3618.
19. [19]
  YANG Yun-Han, ZHAO Xue-Qiu, DU Yao, YANG Jun-Li, CHEN Wen, LI Yan-Hua, YANG Li-Juan, CHUAN Yong-Ming. Chin. Tradit. Herbal Drugs, 2019, 50(2):352-362. 杨云汉, 赵雪秋, 杜瑶, 杨俊丽, 陈文, 李燕华, 杨丽娟, 钏永明. 中草药, 2019, 50(2):352-362.
20. [20]
  PRIYA A S, BALAKRISHNAN S B, VEERAKANELLORE G B, STALIN T. J. Mol. Struct., 2018, 1160:1-8.PRIYA A S, BALAKRISHNAN S B, VEERAKANELLORE G B, STALIN T. J. Mol. Struct., 2018, 1160:1-8.
21. [21]
  JIA S Y, TANG D Y, PENG J, SUN Z J, YANG Y. Carbohydr. Polym., 2019, 208:486-494.JIA S Y, TANG D Y, PENG J, SUN Z J, YANG Y. Carbohydr. Polym., 2019, 208:486-494.
22. [22]
  MOHANDOSS S, EDISON T N J I, ATCHUDAN R, PALANISAMY S, PRABHU N M, NAPOLEON A A, YOU S G, LEE Y R. J. Mol. Liq., 2020, 319:114358.MOHANDOSS S, EDISON T N J I, ATCHUDAN R, PALANISAMY S, PRABHU N M, NAPOLEON A A, YOU S G, LEE Y R. J. Mol. Liq., 2020, 319:114358.
23. [23]
  KRZAK A, BILEWICZ R. Bioelectrochemistry, 2020, 136:107587.KRZAK A, BILEWICZ R. Bioelectrochemistry, 2020, 136:107587.
24. [24]
  SKUREDINA A A, LE-DEYGEN I M, BELOGUROVA N G, KUDRYASHOVA E V. Carbohydr. Res., 2020, 498:108183.SKUREDINA A A, LE-DEYGEN I M, BELOGUROVA N G, KUDRYASHOVA E V. Carbohydr. Res., 2020, 498:108183.
25. [25]
  ROJAS-AGUIRRE Y, TORRES-MENA M A, LÓPE-MÉNDEZ L J, AlCARAZ-ESTRADA S L, GUADARRAMA P, URUCHA-ORT'Z J M. Carbohydr. Polym., 2019, 223:115113.ROJAS-AGUIRRE Y, TORRES-MENA M A, LÓPE-MÉNDEZ L J, AlCARAZ-ESTRADA S L, GUADARRAMA P, URUCHA-ORT'Z J M. Carbohydr. Polym., 2019, 223:115113.
26. [26]
  LIU Y Y, FAN X D, ZHAO Y B. J. Polym. Sci. Part A:Polym. Chem., 2005, 43(16):3516-3524.LIU Y Y, FAN X D, ZHAO Y B. J. Polym. Sci. Part A:Polym. Chem., 2005, 43(16):3516-3524.
27. [27]
  JIANG H M, YANG H, ZHANG S F. J. Inclusion Phenom. Macrocyclic Chem., 2012, 73(1-4):415-421.JIANG H M, YANG H, ZHANG S F. J. Inclusion Phenom. Macrocyclic Chem., 2012, 73(1-4):415-421.
28. [28]
  YANG K, CHANG Y C, WEN J, LU Y C, PEI Y X, CAO S P, WANG F, PEI Z C. Chem. Mater., 2016, 28(7):1990-1993.YANG K, CHANG Y C, WEN J, LU Y C, PEI Y X, CAO S P, WANG F, PEI Z C. Chem. Mater., 2016, 28(7):1990-1993.
29. [29]
  MONTASSIER P, DUCHÊNE D, POELMAN M. C. Int. J. Pharm., 1997, 153(2):199-209.MONTASSIER P, DUCHÊNE D, POELMAN M. C. Int. J. Pharm., 1997, 153(2):199-209.
30. [30]
  JIN Wen, LI Fei-Yang, HUANG Yu-Rong, YANG Hui-Wen, CHI Shao-Ming, ZHU Hong-You, LEI Ze, ZHAO Yan. Chin. J. Anal. Chem., 2019, 47(8):1235-1242. 晋文, 李飞杨, 黄宇蓉, 杨惠文, 迟绍明, 朱洪友, 雷泽, 赵焱. 分析化学, 2019, 47(8):1235-1242.
31. [31]
  CASO J V, RUSSO L, PALMIERI M, MALGIERI G, GALDIERO S, FALANGA A, ISERNIA C, IACOVINO R. Amino Acids, 2015, 47(10):2215-2227.CASO J V, RUSSO L, PALMIERI M, MALGIERI G, GALDIERO S, FALANGA A, ISERNIA C, IACOVINO R. Amino Acids, 2015, 47(10):2215-2227.
32. [32]
  MELO C D O, RODRIGUES M S D S, SILVA M V S D, MARCELINO H R, MOURA R O D, OLIVEIRA E E. J. Mol. Struct., 2020:128945.MELO C D O, RODRIGUES M S D S, SILVA M V S D, MARCELINO H R, MOURA R O D, OLIVEIRA E E. J. Mol. Struct., 2020:128945.

扫一扫看文章

计量

PDF下载量: 7
文章访问数: 602
HTML全文浏览量: 77

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

槐果碱与β-环糊精及其衍生物的包合行为研究

通讯作者: 杨丽,E-mail:379090920@qq.com; 杨丽娟,E-mail:yangljyang@sina.com

English

Study on Inclusion Behavior of Sophocarpine with β-Cyclodextrin and Its Derivatives

Corresponding author: YANG Li, ; YANG Li-Juan,

CCS Chemistry：嵌段共聚物自组装成 “三明治”二维有机材料，实现纳米级压力传感功能

CCS Chemistry：颜徐州、鲍哲南：你的皮肤可能是一片SPMs

CCS Chemistry：工作高效不疲劳，只须让催化剂动起来

CCS Chemistry：静电组装导向聚合- 聚电解质纳米凝胶量化制备新策略

CCS Chemistry：金黄色葡萄球菌醛基脱氢酶是如何识别特异性底物的？

计量

通讯作者: 陈斌, bchen63@163.com

中国化学会秘书处

槐果碱与β-环糊精及其衍生物的包合行为研究

通讯作者: 杨丽,E-mail:379090920@qq.com; 杨丽娟,E-mail:yangljyang@sina.com

English

Study on Inclusion Behavior of Sophocarpine with β-Cyclodextrin and Its Derivatives

Corresponding author: YANG Li, ; YANG Li-Juan,

CCS Chemistry：嵌段共聚物自组装成 “三明治”二维有机材料，实现纳米级压力传感功能

CCS Chemistry：颜徐州、鲍哲南： 你的皮肤可能是一片SPMs

CCS Chemistry：工作高效不疲劳，只须让催化剂动起来

CCS Chemistry：静电组装导向聚合- 聚电解质纳米凝胶量化制备新策略

CCS Chemistry：金黄色葡萄球菌醛基脱氢酶是如何识别特异性底物的？

计量

文章相关

通讯作者: 陈斌, bchen63@163.com

中国化学会秘书处

CCS Chemistry：颜徐州、鲍哲南：你的皮肤可能是一片SPMs