Triterpene compounds isolated from Acer mandshuricum and their anti-inflammatory activity.
In our preliminary screening study on the anti-inflammatory activity, a new triterpene compound, aceranol acetate (1), was isolated along with five known compounds: beta-amyrin acetate (2); glutinol acetate (3); friedelin (4); glutinol (5); (3beta)-d-glucopyranoside-stigmast-5-en-3-yl (6), from the stems and leaves of Acer mandshuricum. The structure of the new triterpene was determined to be 5alpha,6alpha-epidioxy-5beta,6beta-epoxy-9,13-dimethyl-25,26-dinoroleanan-3beta-ol acetate by spectroscopic studies. Compounds 2-6 were isolated from this plant for the first. Five triterpene compounds (1-5) showed significant cytotoxic activity with GI(50) in the range of 11.1-17.9microM, whereas steroid compound (6) exhibited moderate activity against four human cancer cell lines (HL-60, SK-OV-3, A549, and HT-29). Furthermore, the anti-inflammatory effects of compounds 1-6 in the non-cytotoxic concentrations (1-100nM) were evaluated for the inhibitory activity of TNF-alpha secretion in the lipopolysaccharide (LPS)-stimulated murine RAW264.7 macrophage cell line. Among the compounds tested, compound 2 showed the strongest anti-inflammatory activity with the inhibition rate up to 38.40% at the concentration of 100nM, whereas other five compounds (2-6) exhibited moderate activity.
Ding
Yan
Y
College of Pharmacy, Chungnam National University, Daejeon 305-764, Republic of Korea.
Liang
Chun
C
Kim
Jun Ho
JH
Lee
Young-Mi
YM
Hyun
Jae-Hee
JH
Kang
Hee-Kyoung
HK
Kim
Jeong-Ah
JA
Min
Byung Sun
BS
Kim
Young Ho
YH
D031002:Acer / Q000737:chemistry*; D000818:Animals; D000893:Anti-Inflammatory Agents / Q000737:chemistry* / Q000302:isolation & purification / Q000633:toxicity; D045744:Cell Line, Tumor; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D008070:Lipopolysaccharides / Q000633:toxicity; D051379:Mice; D009828:Oleanolic Acid / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification / Q000633:toxicity; D010946:Plants, Medicinal / Q000737:chemistry; D014315:Triterpenes / Q000737:chemistry* / Q000302:isolation & purification / Q000633:toxicity; D014409:Tumor Necrosis Factor-alpha / Q000378:metabolism
D000893:Anti-Inflammatory Agents; D008070:Lipopolysaccharides; D014315:Triterpenes; D014409:Tumor Necrosis Factor-alpha; C549574:aceranol acetate; D009828:Oleanolic Acid; C000265:beta-amyrin acetate