Antibacterial triterpenoid acids from Dillenia papuana.
Three new oleanene-type triterpenoids, dillenic acids A [1], B [2], and C [3], and two known compounds, 3-oxoolean-1,12-dien-30-oic acid [4] (a new natural product) and the lupene derivative betulinaldehyde, have been isolated from the Papua New Guinean medicinal plant Dillenia papuana. The structures of the new compounds were elucidated as 2 alpha-hydroxy-3-oxoolean-12-en-30-oic acid, 2-oxo-3 beta-hydroxyolean-12-en-30-oic acid and 1 alpha-hydroxy-3-oxoolean-12-en-30-oic acid. The 1H- and 13C-nmr data of all new compounds were assigned unambiguously using a variety of 2D nmr experiments including 1H-1H-COSY, HMQC, HMBC, and NOESY experiments. Of these compounds, 1-4 showed antibacterial activities against Bacillus subtilis, Escherichia coli, and Micrococcus luteus.
Nick
A
A
Department of Pharmacy, Swiss Federal Institute of Technology (ETH) Zurich.
Wright
A D
AD
Sticher
O
O
Rali
T
T
D000900:Anti-Bacterial Agents / Q000302:isolation & purification* / Q000494:pharmacology; D001412:Bacillus subtilis / Q000187:drug effects; D004926:Escherichia coli / Q000187:drug effects; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D016982:Micrococcus luteus / Q000187:drug effects; D009512:New Guinea; D009828:Oleanolic Acid / Q000031:analogs & derivatives* / Q000302:isolation & purification / Q000494:pharmacology; D018515:Plant Leaves / Q000737:chemistry; D018547:Plant Stems / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*; D013055:Spectrophotometry, Infrared; D014197:Trees / Q000737:chemistry
D000900:Anti-Bacterial Agents; C091080:dillenic acid A; C091082:dillenic acid B; C091083:dillenic acid C; D009828:Oleanolic Acid