Research for Natural Anti-type I Allergic Compounds with Reactive Oxygen Species Scavenging Activity

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Ninety-three compounds were isolated from the methanol or acetone extracts of six edible and medical plants, and their structures were elucidated on the basis of spectroscopic data as well as chemical evidence. Among these compounds, thirty phenolic compounds and forty-three polyphenols from tea leaves were examined for their antioxidative activity by the ferric thiocyanate method, and fifty-seven compounds showed a stronger antioxidative activity than α-tocopherol. Moreover, thirty-four antioxidants were assayed for their inhibitory effect on the activation of inactive hyaluronidase induced by compound 48/80. Twenty-one compounds indicated stronger inhibitory effect than tranilast. Especially, three compounds were identified as stronger inhibitors than disodium chromoglycate. The chemical structure and antihyaluronidase activity relationships suggested that catechol group seem to be important for the inhibitory effect. In addition, the inhibitory effect of flavonoid glycosides is less than those of the corresponding aglycone. In the case of caffeoyl quinic acid derivatives, those with free carboxyl group indicated a stronger inhibitory effect than methyl ester derivatives. Furthermore, proanthocyanidins which possess catechol group in the B-ring of upper unit showed a stronger inhibitory effect than those possess pyrogallol group in the B-ring of upper unit. Moreover, the acylation at the 3-OH in the lower unit of proanthocyanidin by galloyl group exhibited a higher inhibition. In the case of theasinensis, the inhibitory effect appeared to increase with the number of galloyl group attached to 3-OH position. From these results, flavonoids and caffeoyl quinic acid derivatives which possess catechol group and proanthocyanidins and theasinensins that possess galloyl group may be effective as an anti-type I allergic drug.