Register      Login
Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
Shopping Cart: ( empty )
You are here: Home > Journals > CH > CH15194
RESEARCH ARTICLE
Contents Vol 69(2)

Host–Guest Inclusion System of Luteolin with Polyamine-β-cyclodextrin: Preparation, Characterisation, Anti-oxidant and Anti-cancer Activity

Manshuo Liu A , Rongqiang Liao A , Yulin Zhao B and Bo Yang A C
+ Author Affiliations
- Author Affiliations

A Faculty of Life Science and Technology, Kunming University of Science and Technology, Kunming 650500, China.

B Faculty of Chemical Engineering, Kunming University of Science and Technology, Kunming 650500, China.

C Corresponding author. Email: yangb_2015@163.com

Australian Journal of Chemistry 69(2) 174-182 https://doi.org/10.1071/CH15194
Submitted: 16 April 2015  Accepted: 30 June 2015   Published: 7 August 2015

Abstract

The characterisation, inclusion complexation behaviours, and binding ability of inclusion complexes of luteolin (LU) with four polyamine-modified β-cyclodextrins (NH2-βCD, EN-βCD, DETA-βCD, TETA-βCD; where EN = ethylenediamine; DETA = diethylenediamine; TETA = triethylenetetramine) were investigated in both the solid and solution forms by photoluminescence spectroscopy, 1H and 2D NMR spectroscopy, differential scanning calorimetry, X-ray diffraction, and scanning electron microscopy. The results showed that the water solubility, and the anti-oxidant activity and anti-cancer activity of LU were significantly increased in the inclusion complex with polyamine-β-cyclodextrin. The LU/CDs complex will be useful for its application as herbal medicine or healthcare product.


References

[1]  M. Lopez-Lazaro, Mini-Rev. Med. Chem. 2009, 9, 31.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXks1Srt7Y%3D&md5=a35ab8ba71c0a7e93bbf8d8a7439438fCAS | 19149659PubMed |

[2]  G. Seelinger, I. Merfort, C. M. Schempp, Planta Med. 2008, 74, 1667.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXit1Ol&md5=ae59fdf5dcd24e80f4c588d71f80d07aCAS | 18937165PubMed |

[3]  H. Sakagami, S. Amano, H. Kikuchi, Y. Nakamura, R. Kuroshita, S. Watanabe, K. Satoh, H. Hasegawa, A. Nomura, T. Kanamoto, S. Terakubo, H. Nakashima, S. Taniguchi, T. Ohizumi, In Vivo 2008, 22, 471.
         | 18712174PubMed |

[4]  C. S. Ong, J. Zhou, C. N. Ong, H. M. Shen, Cancer Lett. 2010, 98, 7.

[5]  H. Ueda, C. Yamazaki, M. Yamazaki, Biol. Pharm. Bull. 2002, 25, 1197.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD38Xnt1entL0%3D&md5=6979b7a85e8bc087673f4cc508a630a8CAS | 12230117PubMed |

[6]  P. H. Liao, L. M. Hung, Y. H. Chen, Y. H. Kuan, F. B. Zhang, R. H. Lin, Circ. J. 2011, 75, 443.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXisVamsbw%3D&md5=aa890c5722f5ff654ad05a81f4fae15bCAS | 21178298PubMed |

[7]  D. A. Moreno, Life Sci. 2006, 78, 2797.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XjvValsb8%3D&md5=f62aad5943acb57cbabce48b2b63b729CAS | 16337240PubMed |

[8]  O. Farombi, O. Owoeye, Int. J. Environ. Res. Public Health 2011, 8, 2533.
         | Crossref | GoogleScholarGoogle Scholar |

[9]  K. Uekama, F. Hirayama, T. Irie, Chem. Rev. 1998, 98, 2045.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1cXksV2itr0%3D&md5=dfa9a0de6e238981bd90f25b7723e4f6CAS | 11848959PubMed |

[10]  A. T. M. Serajuddin, J. Pharm. Sci. 1999, 88, 1058.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1MXltl2jtbk%3D&md5=5ae411e31dd5d4b6532ab456222c8886CAS |

[11]  M. V. Rekharsky, Y. Inoue, Chem. Rev. 1998, 98, 1875.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1cXksV2itbg%3D&md5=06dfa1b30a3025e1f73c7b324f62e06cCAS | 11848952PubMed |

[12]  S. D. Tommasini, R. Raneri, M. L. Ficarra, R. Calabrò, P. Ficarra, J. Pharm. Biomed. Anal. 2004, 35, 379.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXivVWrtLw%3D&md5=e2af81b885ede6db891c74a082055f3eCAS |

[13]  L. Koontz, J. E. Marcy, S. E. Duncan, J. Agric. Food Chem. 2009, 57, 1162.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXhtFOktb8%3D&md5=47d45b9287c5123f022f23790033ab65CAS |

[14]  C. Jullian, L. Moyano, C. Yanez, Spectrochim. Acta, Part A 2007, 67, 230.
         | Crossref | GoogleScholarGoogle Scholar |

[15]  S. X. Ma, C. Wen, D. Y. Xiao, J. Pharm. Biomed. Anal 2012, 67–68, 193.
         | Crossref | GoogleScholarGoogle Scholar | 22633603PubMed |

[16]  Y. Liu, G. S. Chen, L. Li, H. Y. Zhang, D. X. Cao, Y. J. Yuan, J. Med. Chem. 2003, 46, 4634.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXnsVehtr0%3D&md5=0f433745c7ce4c03d70037b9a1cfadf0CAS | 14561082PubMed |

[17]  Y. Zhao, Y. C. Yang, H. Shi, H. Y. Zhu, R. Huang, C. M. Chi, Y. Zhao, Helv. Chim. Acta 2010, 93, 1136.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXnvVOju7w%3D&md5=e825a76ab03aedea4ea4c72ff90e6fd0CAS |

[18]  Y. Liu, G. S. Chen, Y. Chen, F. Ding, Org. Biomol. Chem. 2005, 3, 2519.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXlvVSksLs%3D&md5=786532c99571d18b69cb03536ba0f9a1CAS | 15999183PubMed |

[19]  J. Bügler, N. A. J. M. Sommerdijk, A. J. W. G. Visser, A. van Hoek, R. J. M. Nolte, J. F. J. Engbersen, D. N. Reinhoudt, J. Am. Chem. Soc. 1999, 121, 28.
         | Crossref | GoogleScholarGoogle Scholar |

[20]  H. M. Kim, H. W. Kim, S. H. Jung, Bull. Korean Chem. Soc. 2008, 29, 590.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXlt1OjurY%3D&md5=939dc1ee5fbe9342b3d13debc11eca03CAS |

[21]  B. Liu, Food Chem. 2013, 141, 900.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXps1Ggtb0%3D&md5=b8590571732cf53eb9d2c1bfda554879CAS | 23790865PubMed |

[22]  X. M. Yang, Y. L. Zhao, Y. J. Chen, X. L. Liao, C. Z. Gao, D. Xiao, Q. X. Qin, D. Yi, B. Yang, Mater. Sci. Eng., C 2013, 33, 2386.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXjtlamtLk%3D&md5=e24b71346fdaf659f795e708bbcccd58CAS |

[23]  Y. Inoue, K. Yamamoto, T. Wada, S. Everitt, X. M. Gao, Z. J. Hou, L. H. Tong, S. K. Jiang, H. M. Wu, J. Chem. Soc. 1988, 21, 807.

[24]  J. Szejtli, Chem. Rev. 1998, 98, 1743.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1cXksV2itrw%3D&md5=b331ca151b9dcb4a240623b2a2617e14CAS | 11848947PubMed |

[25]  C. Jullian, C. Cifuentes, M. Alfaro, Bioorg. Med. Chem. 2010, 18, 5025.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXoslagtb4%3D&md5=22a39c9851fc3124549577502ce3f953CAS | 20576438PubMed |

[26]  P. Thordarson, Chem. Soc. Rev. 2011, 40, 1305.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXit1Kitr4%3D&md5=8491e4ec2efae2af0f4e1b0adb089bbcCAS | 21125111PubMed |

[27]  S. Rahman, A. Zein, P. Thordarson, RSC Adv. 2015, 5, 54848.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2MXhtVWjtrjJ&md5=11bedc5d93a53b6bc981932d535c6926CAS |

[28]  Y. Liu, C. S. Chen, Y. Chen, J. Lin, Bioorg. Med. Chem. 2005, 13, 4037.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXks1Gjsrw%3D&md5=2ce73a996a9f485e6626719e98d95113CAS | 15911316PubMed |

[29]  D. Araújo, Bioorg. Med. Chem. 2008, 16, 5788.
         | Crossref | GoogleScholarGoogle Scholar |

[30]  I. Correia, N. Bezzenine, N. Ronzani, N. Platzer, J. C. Beloeil, B. T. Doan, J. Phys. Org. Chem. 2002, 15, 647.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD38Xmslyrsrg%3D&md5=1738246dd924994fd778e557113f3736CAS |

[31]  J. Wang, Y. Cao, B. Sun, C. Wang, Food Chem. 2011, 124, 1069.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXhtFOitLfJ&md5=6c4f69ad27a562de0b7affd00c3a1a35CAS |

[32]  J. Khan, A. Alexander, S. Ajazuddin, S. Saraf, Saraf, J. Pharm. Pharmacol. 2014, 66, 1451.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXhsFahurrO&md5=a51ac08e0aae6f570fecf7548b8d64f4CAS | 24934881PubMed |

[33]  Y. Kwon, H. Kim, Bull. Korean Chem. Soc. 2010, 31, 10.

[34]  R. Iacovino, F. Rapuano, Int. J. Mol. Sci. 2013, 14, 13022.
         | Crossref | GoogleScholarGoogle Scholar | 23799358PubMed |

[35]  B. J. Shen, L. H. Tong, D. S. Jin, Synth. Commun. 1991, 21, 635.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3MXkslajtLY%3D&md5=38b4904f34f604d18fc9aad2a3132bdbCAS |

[36]  Y. Liu, Y. Chen, L. Li, H. Y. Zhang, S. X. Liu, X. D. Guan, J. Org. Chem. 2001, 66, 8518.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3MXosVSqsL8%3D&md5=e63dbbb71ac28760f096255d4be08636CAS | 11735533PubMed |

[37]  S. X. Ma, W. Chen, X. D. Yang, J. Pharm. Biomed. Anal. 2012, 67–68, 193.
         | Crossref | GoogleScholarGoogle Scholar | 22633603PubMed |

[38]  L. L. Mensor, F. S. Menezes, G. G. Leitão, A. S. Reis, T. C. dos Santos, C. S. Coube, S. G. Leitão, Phytother. Res. 2001, 15, 127.
         | Crossref | GoogleScholarGoogle Scholar | 1:STN:280:DC%2BD3M7ntVajuw%3D%3D&md5=6c47c02a1e15a347548ec28e51895a8fCAS | 11268111PubMed |

[39]  C. Jullian, C. Cifuentes, M. Alfaro, S. Miranda, G. Barriga, C. Olea-Azar, Bioorg. Med. Chem. 2010, 18, 5025.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXoslagtb4%3D&md5=22a39c9851fc3124549577502ce3f953CAS | 20576438PubMed |

[40]  E. G. Haggag, A. M. Kamal, M. I. S. Abdelhady, M. M. El-Sayed, E. A. El-Wakil, S. S. Abd-El-hamed, Pharm. Biol. 2011, 49, 1103.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXhtlGlurfE&md5=94419ccc5f0c31626490d0a74faa6da8CAS | 21595573PubMed |