Differentiation- and apoptosis-inducing activities by pentacyclic triterpenes on a mouse melanoma cell line.
In a study to investigate the relationship between the chemical structure and the differentiation-inducing activity of pentacyclic triterpenes, several lupane, oleanane, and ursane triterpenes were prepared and their effects on B16 2F2 melanoma cell differentiation and growth were examined. Eleven lupane triterpenes used in this study acted on the melanoma cells as a melanogen, but no induction of melanogenesis of B16 2F2 cells by oleanane and ursane was detected. The differences at C-17 of the lupane series and acetylation of the OH group at C-3 did not markedly influence their activities. However, the ED(50) value for up-regulation of melanin biosynthesis was markedly decreased by the oxidation of the OH group at C-3 of lupeol (1). Betulinic acid (11), its methyl ester (12), lup-28-al-20(29)-ene-3beta-ol (9), and lup-28-al-20(29)-en-3-one (10) inhibited B16 2F2 cell proliferation by induction of apoptosis. These findings suggested that the carbonyl group at C-17 might be essential for the apoptotic effects of these compounds on B16 2F2 cells.
Hata
Keishi
K
Akita Research Institute of Food & Brewing (ARIF), 4-26 Sanuki, Araya-machi, Akita 010-1623, Japan.
Hori
Kazuyuki
K
Takahashi
Saori
S
D000818:Animals; D017209:Apoptosis / Q000187:drug effects; D002454:Cell Differentiation / Q000187:drug effects; D020128:Inhibitory Concentration 50; D009682:Magnetic Resonance Spectroscopy; D008546:Melanoma, Experimental / Q000473:pathology*; D051379:Mice; D015394:Molecular Structure; D010084:Oxidation-Reduction; D053978:Pentacyclic Triterpenes; D011726:Pyridinium Compounds / Q000737:chemistry; D017550:Spectroscopy, Fourier Transform Infrared; D013329:Structure-Activity Relationship; D014315:Triterpenes / Q000494:pharmacology*; D014407:Tumor Cells, Cultured / Q000187:drug effects; D000094062:Betulinic Acid; D000094042:Lupanes
D053978:Pentacyclic Triterpenes; D011726:Pyridinium Compounds; D014315:Triterpenes; D000094062:Betulinic Acid; C002503:betulin; C111019:pyridinium chlorochromate; C010480:lupeol; D000094042:Lupanes