3-Geranyl-4-hydroxy-5-(3'-methyl-2'-butenyl)benzoic acid as an anti-inflammatory compound from Myrsine seguinii.
Bioassay-guided isolation of anti-inflammatory compounds from the methanol extract of Myrsine seguinii yielded an anti-inflammatory compound (1). The structure of compound 1 was elucidated to be 3-geranyl-4-hydroxy-5-(3'-methyl-2'-butenyl)benzoic acid on the basis of its spectroscopic data. Compound 1 strongly suppressed 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced inflammation on mouse ears at a dose of 500 micrograms (inhibitory effect (IE): 65%). The acetate and the methyl ether of 1 showed moderate activity at a 500-microgram application, with IE 38% and 27%, respectively. However, the methyl ester and the dimethyl derivative of 1 did not show activity at the same dose. The related compounds of 1, o-, m- and p-hydroxybenzoic acids also did not exhibit notable activity. These results indicate that the carboxylic acid and lipophilic terpene moieties of 1 were significant structural features for anti-inflammatory activity.
Dong
M
M
United Graduate School of Agricultural Science, Gifu University, Japan.
Nagaoka
M
M
Miyazaki
S
S
Iriye
R
R
Hirota
M
M
D000818:Animals; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D001565:Benzoates / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D004487:Edema / Q000139:chemically induced / Q000517:prevention & control; D007249:Inflammation / Q000139:chemically induced / Q000517:prevention & control; D009682:Magnetic Resonance Spectroscopy; D019684:Magnoliopsida / Q000737:chemistry*; D051379:Mice; D010946:Plants, Medicinal / Q000737:chemistry*; D013729:Terpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D013755:Tetradecanoylphorbol Acetate / Q000633:toxicity
C401930:3-geranyl-4-hydroxy-5-(3'-methyl-2'-butenyl)benzoic acid; D000894:Anti-Inflammatory Agents, Non-Steroidal; D001565:Benzoates; D013729:Terpenes; D013755:Tetradecanoylphorbol Acetate