Register      Login
Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

Synthesis of Carbohydrate-based Natural Products from Leonurus japonicus and their Biological Evaluation as Anti-oxidants

Evette Clayton A , Mitchell Hattie A , Aleksandra W. Debowski A and Keith A. Stubbs A B
+ Author Affiliations
- Author Affiliations

A School of Chemistry and Biochemistry, The University of Western Australia, 35 Stirling Highway, Crawley, WA 6009, Australia.

B Corresponding author. Email: keith.stubbs@uwa.edu.au

Australian Journal of Chemistry 67(10) 1461-1470 https://doi.org/10.1071/CH13621
Submitted: 11 November 2013  Accepted: 5 December 2013   Published: 17 January 2014

Abstract

Natural products are important materials that have found a wide variety of uses, especially in medicine. Traditional Chinese medicine (TCM) has especially taken advantage of natural products and compounds found in Leonurus, a species of herb used extensively in TCM to treat various ailments. Herein we describe the synthesis of three natural products from Leonurus japonicus and our investigation of their hepatoprotective properties.


References

[1]  D. J. Newman, G. M. Cragg, K. M. Snader, J. Nat. Prod. 2003, 66, 1022.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXksVylu7g%3D&md5=09bd9d34b64854a43de80c2a2522ed06CAS | 12880330PubMed |

[2]  R. Graziose, M. A. Lila, I. Raskin, Curr. Drug Discov. Technol. 2010, 7, 2.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXlt1Grur0%3D&md5=b0124b3edc4d0bfbf861fa914752d860CAS | 20156139PubMed |

[3]  B. K. H. Tan, J. Vanitha, Curr. Med. Chem. 2004, 11, 1423.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXktlOgt7Y%3D&md5=2b8c6ad03da9daad152c4840559723beCAS |

[4]  S. O. Oyedemi, M. T. Yakubu, A. J. Afolayan, J. Med. Plant. Res 2011, 5, 119.
         | 1:CAS:528:DC%2BC3MXitFygtrk%3D&md5=f4d87524fd5a9588b89da07a32c3a60aCAS |

[5]  X. H. Liu, L. L. Pan, Y. Z. Zhu, Clin. Exp. Pharmacol. P. 2012, 39, 274.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XjsVOjurw%3D&md5=5f14edab681c0f7ed730b3418c419829CAS |

[6]  Y. Li, Z. Chen, Z. Feng, Y. Yang, J. Jiang, P. Zhang, Carbohyd. Res. 2012, 348, 42.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XhtFKqu7s%3D&md5=53e1dfa4b9bf88799dcbbb395b6423c1CAS |

[7]  H. I. Duynstee, M. C. de Koning, H. Ovaa, G. A. van der Marel, J. H. van Boom, Eur. J. Org. Chem. 1999, 2623.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1MXmtlKltrs%3D&md5=152314225f21397ee27056ca877af29fCAS |

[8]  H. Kobayashi, H. Karasawa, T. Miyase, S. Fukushima, Chem. Pharm. Bull. 1985, 33, 1452.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL2MXks1yhsbk%3D&md5=5bb550976578ea10385d5da1123f338bCAS |

[9]  G. Gu, Y. Zhao, Z. Guo, Carbohyd. Res. 2013, 380, 174.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXhsFKktLvP&md5=95a04a2644bb3072acc2c782788af41aCAS |

[10]  M. Ota, K. Takahashi, H. Kofujita, J. Wood Sci. 1998, 44, 320.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1cXmtFOitbY%3D&md5=2f7470c4c7e5b89b9110af4ccc07636fCAS |

[11]  M. Izumi, K. Fukase, S. Kusumoto, Biosci. Biotech. Bioch. 2002, 66, 211.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD38Xht1Sksrw%3D&md5=729b9c43fe7fec76cf4cb3eba07235aeCAS |

[12]  G. Huang, X. Mei, M. Liu, Carbohydr. Res. 2005, 340, 603.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXhs1aitbY%3D&md5=d485476beb7ba57b6860adf247ea6f9eCAS | 15721330PubMed |

[13]  M. G. Donahue, J. N. Johnston, Bioorg. Med. Chem. Lett. 2006, 16, 5602.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XhtVSis73P&md5=db9df92e32cf1bda21b2ceed82506af0CAS | 16935501PubMed |

[14]  R. R. Schmidt, J. Michel, M. Roos, Liebigs Ann. Chem. 1984, 1343.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL2cXlsFahs70%3D&md5=e59c67c5fee167c61b668427e8b4e3f9CAS |

[15]  L. Ban, M. Mrksich, Angew. Chem. Int. Ed. 2008, 47, 3396.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXmtlajsLg%3D&md5=e22415b1a97f2873458e3a07a932e216CAS |

[16]  S. G. Mills, A. Ali, C. Smith, Prodrugs of Oxolidinone CETP inhibitors 2010, WO2010/039474.

[17]  J. Zhang, F. Kong, Tetrahedron 2003, 59, 1429.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXhtFCktr8%3D&md5=9539939fa34156f572c7953a4863c1c6CAS |

[18]  R. K. Jain, C. F. Piskorz, B. Huang, R. D. Locke, H. Han, A. Koenig, A. Varki, L. Khushi, Glycobiology 1998, 8, 707.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1cXksFClu78%3D&md5=edd19d2e683b7cff299d881e3709439eCAS | 9621111PubMed |

[19]  T. Murakami, H. Matsuda, M. Inadzuki, K. Hirano, M. Yoshikawa, Chem. Pharm. Bull. 1999, 47, 1717.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3cXit1Kr&md5=09b336ee9fc0958f778eea84a665f1feCAS |

[20]  M. J. Czaja, Semin. Liver Dis. 2007, 27, 378.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXhtl2gsrvN&md5=711236a6fcda491436f5a1b170aa37f9CAS | 17979074PubMed |

[21]  B. Halliwell, Lancet 1994, 344, 721.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2cXmsFamurg%3D&md5=24c5ea7c958524c19d38cb43032b3144CAS | 7915779PubMed |

[22]  H. E. Poulsen, H. Prieme, S. Loft, Eur. J. Cancer Prev. 1998, 7, 9.
         | 1:STN:280:DyaK1c7ntVOqtA%3D%3D&md5=201854d78890dcf80e996e4503c5d95eCAS | 9511847PubMed |

[23]  O. Akyol, H. Herken, E. Uz, E. Fadillioglu, S. Unal, S. Sogut, H. Ozyurt, H. A. Savas, Prog. Neuro.-Psychoph 2002, 26, 995.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD38XmsVCiuro%3D&md5=de3494d9a9a88c1494bdcb02dac2df4cCAS |

[24]  M. J. Czaja, Antioxid. Redox Sign. 2002, 4, 759.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXhtVals7w%3D&md5=aba9663f33375a59729139247eae3721CAS |

[25]  X. Chen, Z. Zhong, Z. Xu, L. Chen, Y. Wang, Pharmacol. Rep. 2011, 63, 724.
         | 1:CAS:528:DC%2BC3MXhsFyksLzE&md5=bf5b431bf78541bf973d2ca042967fa8CAS | 21857083PubMed |

[26]  G. E. Henry, R. A. Momin, M. G. Nair, D. L. Dewitt, J. Agric. Food Chem. 2002, 50, 2231.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD38XhtlOkt7w%3D&md5=dd3cb6bcdb81730539d716fa7fdc3e5aCAS | 11929276PubMed |

[27]  Z. Jia, H. Zhu, J. Li, X. Wang, H. Misra, Y. Li, Spinal Cord 2012, 50, 264.
         | Crossref | GoogleScholarGoogle Scholar | 1:STN:280:DC%2BC38zmtlyhtA%3D%3D&md5=58d0c9d4e130c02ef951b8d5a781705eCAS | 21987065PubMed |