Structure-activity relationship of polyphenols on inhibition of chemical mediator release from rat peritoneal exudate cells.
The effect of phenolic compounds in foodstuffs on histamine and leukotriene B4 (LTB4) release from rat peritoneal exudate cells and their antioxidative activity were examined to assess their antiallergenic activities. Among them, triphenols such as pyrogallol and gallic acid inhibited histamine release from the cells, but diphenols did not. On the other hand, o- and p-diphenols such as catechol and hydroquinone with strong antioxidative activity inhibited LTB4 release as strongly as pyrogallol, but an m-derivative resorcinol with weak antioxidative activity did not. Though carboxylated compounds and their noncarboxylated counterparts were antioxidative, the former exerted a much weaker inhibitory effect on the LTB4 release than the latter. In flavonols, only myricetin with a triphenolic B ring strongly inhibited histamine release, but all flavonols strongly suppressed LTB4 release irrespective of the number of OH groups in the B ring. Among flavonoids with an o-diphenolic B ring, flavonol and flavone with a C4-carbonyl group strongly inhibited LTB4 release, whereas the activity of anthocyan without C4-carbonyl was much weaker than the above compounds. These results suggest that triphenolic structure is essential for the inhibition of histamine release. On the other hand, antioxidative activity and membrane permeability of phenolic compounds seemed to be essential for the inhibition of LTB4 release. In addition, the C4-carbonyl group seemed to be important for strongly inhibiting LTB4 release.
Yamada
K
K
Department of Food Science and Technology, Faculty of Agriculture, Kyushu University, Japan.
Shoji
K
K
Mori
M
M
Ueyama
T
T
Matsuo
N
N
Oka
S
S
Nishiyama
K
K
Sugano
M
M
D000818:Animals; D000975:Antioxidants / Q000494:pharmacology; D015764:Bepridil / Q000031:analogs & derivatives / Q000494:pharmacology; D001713:Biphenyl Compounds; D002084:Butylated Hydroxytoluene / Q000494:pharmacology; D005122:Exudates and Transudates; D005419:Flavonoids / Q000494:pharmacology; D005609:Free Radicals; D006636:Histamine Release; D007975:Leukotriene B4 / Q000378:metabolism*; D008297:Male; D010537:Peritoneum / Q000166:cytology; D010636:Phenols / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*; D010851:Picrates; D011108:Polymers / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*; D051381:Rats; D017208:Rats, Wistar; D013329:Structure-Activity Relationship; D014810:Vitamin E / Q000494:pharmacology
D000975:Antioxidants; D001713:Biphenyl Compounds; D005419:Flavonoids; D005609:Free Radicals; D010636:Phenols; D010851:Picrates; D011108:Polymers; D014810:Vitamin E; D007975:Leukotriene B4; D002084:Butylated Hydroxytoluene; D015764:Bepridil; C004931:1,1-diphenyl-2-picrylhydrazyl