title: Semi-synthesis of nitrogen derivatives of oleanolic acid and effect on breast carcinoma MCF-7 cells.
abstract: BACKGROUND
  Oleanolic acid is a triterpenoid that has shown in vitro cytotoxic activity against human tumour cells and is known to be present in many higher plants.
  
  
  METHODS
  Oleanolic acid is known to have some biological potential including anticancer property. Oleanolic acid was isolated from the ethyl acetate fraction of Syzygium aromaticum seed with an aim of dervitatising the functional group and evaluating the biological activities of the semi-synthesised compounds. Acylation of the alcohol functional group of the oleanolic acid afforded the opportunity of hydrazine reaction to give 3-acetoleanolic hydrazide. Further reaction of 3-acetoleanolic hydrazide with benzyladehyde, glacial acetic acid and methanol resulted in the synthesis of the corresponding 3-acetoxyoleanolic hydrazone.
  
  
  RESULTS
  The semi-synthetic oleanolic acid derivatives did not exhibit enhanced cytotoxic activity over oleanolic acid itself.
  
  
  CONCLUSIONS
  3-acetoxyoleanolic hydrazide has a potent anticancer activity.
authors: Department of Chemistry, University of Fort Hare, Alice, South Africa ooyedeji@ufh.ac.za opeoluwa_oyedeji@yahoo.co.uk.
authors: Opeoluwa O
authors: OO
authors: Oyedeji
authors: Department of Chemistry, University of Zululand, KwaDlangezwa, South Africa.
authors: Francis O
authors: FO
authors: Shode
authors: Department of Chemistry and Chemical Technology, Walter Sisulu University, Mthatha, South Africa.
authors: Adebola O
authors: AO
authors: Oyedeji
authors: Department of Chemistry and Chemical Technology, Walter Sisulu University, Mthatha, South Africa.
authors: Sandile P
authors: SP
authors: Songca
authors: Minority Health International Research Training Program, Elizabeth City State University, Elizabeth City NC, U.S.A.
authors: Ephraim T
authors: ET
authors: Gwebu
authors: Department of Chemistry, University of Alabama in Huntsville, Huntsville, AL, U.S.A.
authors: Gabrielle M
authors: GM
authors: Hill
authors: Department of Chemistry, University of Alabama in Huntsville, Huntsville, AL, U.S.A.
authors: William N
authors: WN
authors: Setzer
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D005260:Female; D006801:Humans; D061986:MCF-7 Cells; D009682:Magnetic Resonance Spectroscopy; D009584:Nitrogen; D009828:Oleanolic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology
chemical_list: D000970:Antineoplastic Agents; D009828:Oleanolic Acid; D009584:Nitrogen
keywords: 3-acetoxyoleanolic hydrazine; 3-acetoxyoleanolichydrazide; Syzygium aromaticum; breast cancer cells; oleanolic acid