title: Biological activity of oleanane triterpene derivatives obtained by chemical derivatization.
abstract: Nine new derivatives of oleanane triterpenoids isolated from Fatsia polycarpa Hayata were synthesized through chemical transformations. Acetylation was effected by reaction with acetic anhydride in pyridine to afford compounds 1-5, while compound 6 was obtained using 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC·HCl) in CH2Cl2. The others derivatives 7-9 were obtained in reactions of the corresponding triterpenoids with EDC·HCl, 4-N,N-dimethylaminopyridine hydrochloride and 4-N,N-dimethylaminopyridine in CH2Cl2. The structures of 1-9 were elucidated from extensive spectroscopic and HRESIMS data, while the structure of 9 was further confirmed by X-ray diffraction analysis. The cytotoxic, anti-hepatitis B virus (HBV), antibacterial, hypoglycaemic and Wnt signaling activities of these derivatives were evaluated in vitro.
authors.affiliation: Department of Life Sciences, National University of Kaohsiung, Kaohsiung 811, Taiwan. choumasa@mail.cmu.edu.tw.
authors.forename: Shi-Yie
authors.initials: SY
authors.lastname: Cheng
authors.forename: Chao-Min
authors.initials: CM
authors.lastname: Wang
authors.forename: Hsueh-Ling
authors.initials: HL
authors.lastname: Cheng
authors.forename: Hui-Jye
authors.initials: HJ
authors.lastname: Chen
authors.forename: Yuan-Man
authors.initials: YM
authors.lastname: Hsu
authors.forename: Yu-Chi
authors.initials: YC
authors.lastname: Lin
authors.forename: Chang-Hung
authors.initials: CH
authors.lastname: Chou
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000494:pharmacology; D000998:Antiviral Agents / Q000138:chemical synthesis / Q000494:pharmacology; D027481:Araliaceae / Q000737:chemistry; D005947:Glucose / Q000378:metabolism; D006090:Gram-Negative Bacteria / Q000187:drug effects; D006094:Gram-Positive Bacteria / Q000187:drug effects; D056945:Hep G2 Cells; D006515:Hepatitis B virus / Q000187:drug effects; D006801:Humans; D007004:Hypoglycemic Agents / Q000138:chemical synthesis / Q000494:pharmacology; D020128:Inhibitory Concentration 50; D008826:Microbial Sensitivity Tests; D008958:Models, Molecular; D008968:Molecular Conformation; D009828:Oleanolic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology*; D060449:Wnt Signaling Pathway / Q000187:drug effects
chemical_list: D000900:Anti-Bacterial Agents; D000998:Antiviral Agents; D007004:Hypoglycemic Agents; D009828:Oleanolic Acid; D005947:Glucose