Inhibition of prostaglandin E2 production by flavone and its related compounds.
We have previously reported that among 12 major ingredients of Sairei-to, Scutellariae radix inhibited prostaglandin E(2) (PGE(2)) production by lipopolysaccharide (LPS)-activated mouse macrophage-like RAW264.7 cells more efficiently than other ingredients, and wogonin, a major flavonoid from Scutellariae radix, showed greater inhibitory activity and membrane permeability than baicalein and baicalin. Here the effects of six other flavonoids, with similar structures, on membrane permeability and PGE(2) production were investigated. 7-Methoxyflavone inhibited the LPS-stimulated PGE(2) production to the greatest extent, followed by flavone>wogonin (5,7-dihydroxy-8-methoxyflavone)>> 7,8-dimethoxyflavone>chrysin (5,7-dihydroxyflavone)> baicalein (5,6,7-trihydroxyflavone)>>chromone. 7-Methoxyflavone also showed the highest membrane permeability, followed by flavone>chrysin>7,8-dimethoxy-flavone>wogonin>baicalein. When PGE(2) inhibitory activity was expressed per molecule incorporated into the cells, wogonin produced the greatest inhibition, further substantiating its anti-inflammatory potency.
Department of Oral and Maxillofacial Surgery, Tokyo Medical University, Shinjyuku-ku, Tokyo, Japan.
Tadayoshi
T
Kaneko
Hiroshige
H
Chiba
Norio
N
Horie
Takao
T
Kato
Masaki
M
Kobayashi
Ken
K
Hashimoto
Kaoru
K
Kusama
Hiroshi
H
Sakagami
D000818:Animals; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*; D002460:Cell Line; D002463:Cell Membrane Permeability / Q000187:drug effects; D002851:Chromatography, High Pressure Liquid; D015232:Dinoprostone / Q000378:metabolism*; D005419:Flavonoids / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*; D017737:Macrophages, Peritoneal / Q000187:drug effects* / Q000378:metabolism; D051379:Mice; D008807:Mice, Inbred BALB C; D010936:Plant Extracts / Q000494:pharmacology; D031364:Scutellaria baicalensis / Q000737:chemistry*
D000894:Anti-Inflammatory Agents, Non-Steroidal; D005419:Flavonoids; D010936:Plant Extracts; D015232:Dinoprostone