New cytotoxic oleanane-type triterpenoids from the cones of Liquidamber styraciflua.
Two new oleanane-type triterpenoids (1 and 2), together with two known compounds, 6beta-hydroxy-3-oxo-lup-20(29)-en-28-oic acid (3) and 3,11-dioxoolean-12-en-28-oic acid (4), were isolated from the stem bark of Liquidamber styraciflua. The structures of 1 and 2 were determined to be 25-acetoxy-3alpha-hydroxyolean-12-en-28-oic acid (1) and 3alpha,25-dihydroxyolean-12-en-28-oic acid (2) on the basis of spectroscopic methods and chemical conversion. Compound 1 showed strong cytotoxicity against a disease-oriented panel of 39 human cancer cell lines, although compounds 2, 3, and 4 showed weaker activity compared to 1.
Sakai
Kuniyoshi
K
Department of Medicinal Chemistry, Osaka University of Pharmaceutical Sciences, 4-20-1 Nasahara, Takatsuki, Osaka 569-1094, Japan.
Fukuda
Yuko
Y
Matsunaga
Shunyo
S
Tanaka
Reiko
R
Yamori
Takao
T
D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D029201:Hamamelidaceae / Q000737:chemistry*; D006801:Humans; D007564:Japan; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D009828:Oleanolic Acid / Q000031:analogs & derivatives / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D010946:Plants, Medicinal / Q000737:chemistry*; D014315:Triterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D014407:Tumor Cells, Cultured
C488647:25-acetoxy-3alpha-hydroxyolean-12-en-28-oic acid; C488648:3alpha,25-dihydroxyolean-12-en-28-oic acid; D000972:Antineoplastic Agents, Phytogenic; D014315:Triterpenes; D009828:Oleanolic Acid