著者

藤田 勇三郎 上原 郁恵 森本 泰子 中嶋 真由美 波多野 力 奥田 拓男

出版者

公益社団法人 日本薬学会

雑誌

藥學雜誌 (ISSN:00316903)

巻号頁・発行日

vol.108, no.2, pp.129-135, 1988

被引用文献数

38

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Inhibitory effects of caffeoylquinic acids isolated from leaves of Artemisia species and other related compounds on the lipoxygenase dependent peroxidation of linoleic acid were studied by kinetic and electron spin resonance(ESR) measurements. The order of inhibition activity was as follows : 3, 5-dicaffeoylquinic acid (ID<SUB>5</SUB>0=2.0&times;10<SUP>-</SUP>5 M)=rosmarinic acid > geraniin (2.8&times;10<SUP>-</SUP>5 M)>&alpha;-tocopherol (3.7&times;10<SUP>-</SUP>5 M)>chlorogenic acid (7.5&times;10<SUP>-</SUP>5 M)=caffeic acid>ferulic acid (2.5&times;10<SUP>-</SUP>4 M). This order coincided well with that obtained from the measurement of radical scavenging activities of these compounds against 1, 1-diphenyl-2-picryl hydrazyl. The inhibition profile of these compounds on lipid peroxidation in the lipoxygenase system was quite similar to those obtained previously in the biological systems of rat liver mitochondria and microsomes. In the separate ESR measurements in alkaline dimethyl sulfoxide solution, all caffeoyl-quinic acids exhibited relatively stable ESR signals assigned as a radical derived from the one-electron oxidation of dihydroxyphenyl group. From these results, it was concluded that the radical scavenging mechanism is commonly operative in both chemical and biological peroxidation systems.

著者

藤田 勇三郎 上原 郁恵 森本 泰子 中嶋 真由美 波多野 力 奥田 拓男

出版者

公益社団法人日本薬学会

雑誌

薬学雑誌 (ISSN:00316903)

巻号頁・発行日

vol.108, no.2, pp.p129-135, 1988-02

被引用文献数

7

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Inhibitory effects of caffeoylquinic acids isolated from leaves of Artemisia species and other related compounds on the lipoxygenase dependent peroxidation of linoleic acid were studied by kinetic and electron spin resonance(ESR) measurements. The order of inhibition activity was as follows : 3,5-dicaffeoylquinic acid (ID_50=2.0×10^-5 M)=rosmarinic acid > geraniin (2.8×10^-5 M)>α-tocopherol (3.7×10^-5 M)>chlorogenic acid (7.5×10^-5 M)=caffeic acid>ferulic acid (2.5×10^-4 M). This order coincided well with that obtained from the measurement of radical scavenging activities of these compounds against 1,1-diphenyl-2-picryl hydrazyl. The inhibition profile of these compounds on lipid peroxidation in the lipoxygenase system was quite similar to those obtained previously in the biological systems of rat liver mitochondria and microsomes. In the separate ESR measurements in alkaline dimethyl sulfoxide solution, all caffeoyl-quinic acids exhibited relatively stable ESR signals assigned as a radical derived from the one-electron oxidation of dihydroxyphenyl group. From these results, it was concluded that the radical scavenging mechanism is commonly operative in both chemical and biological peroxidation systems.

著者

船越 仁 羽場 かおり 小原 加奈江 谷口 博美 玉懸 敬悦 藤田 勇三郎

出版者

公益社団法人 日本化学会

雑誌

日本化学会誌(化学と工業化学) (ISSN:03694577)

巻号頁・発行日

vol.1989, no.9, pp.1516-1522, 1989-09-10 (Released:2011-05-30)

参考文献数

6

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光照射によって生じたジメチン型メロシアニン(MD)の光異性体が,安定体にもどる速度過程を4種の誘導体について測定し,熱異性化速度定数(ka),活性化エネルギー(Ea)に対する複素環効果とプロトンの触媒作用の機構について調べた。kdは複素環の種類,とくに硫黄の導入数によって5ケタもの差となって現われた。溶媒の種類およびpHの変化によって島はいちじるしく変わるが,Eaはほとんど変わらないこと,Arrheniusの頻度因子はほとんど複素環効果を示さないことなどから,異性化の中間体としてプロトン化メロシアニンが重要な役割を果たしており,かつ,活性化エネルギーはプロトン移動過程の障壁ではなくプロトン付加体の内部回転の障壁を反映しているという結論を得た。メロシアニンの熱異性化速度はプロトン性非水溶媒における潜在的プロトン活動度の定量化に役立つと提案し,純メタノールの塩酸等価水素イオン濃度として2×10-6mol・dm-3を得た。

著者

波多野 力 枝松 礼 平松 緑 森 昭胤 藤田 勇三郎 安原 多恵子 吉田 隆志 奥田 拓男

出版者

公益社団法人日本薬学会

雑誌

Chemical & pharmaceutical bulletin (ISSN:00092363)

巻号頁・発行日

vol.37, no.8, pp.2016-2021, 1989-08-25

被引用文献数

14 532

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The scavenging effects of twenty-five tannins including low-molecular polyphenols on the superoxide anion radical (O_2^-) generated in the hypoxanthine-xanthine oxidase system were estimated by electron spin resonance (ESR) measurements of the adducts formed by 5,5-dimethyl-1-pyrroline-N-oxide (DMPO) and the radical. The scavenging effects of tannins and related polyphenols having ortho-trihydroxyl (pyrogallol) structure [galloyl, hexahydroxydiphenoyl (HHDP) groups in hydrolyzable tannins, galloyl group in acylated proanthocyanidins, and the B-ring of some flavan-3-ols] were stronger than the effects of unacylated proanthocyanidins. The effects of tannins and related polyphenols on the superoxide anion radical were also compared with those on the 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical. Each tannin in an ethanol solution of DPPH radical reduced the intensity of the signal of the DPPH radical, and gave a weak signal assignable to a radical derived from that tannin, in a similar way to the appearance of the signal of dl-α-tocopherol radical, accompanied with reduction of the signal of DPPH radical, in a mixture of dl-α-tocopherol and the DPPH radical. In contrast to the case of the superoxide anion radical, the effects of unacylated proanthocyanidins on DPPH radical were comparable with those of the other types of tannins. The scavenging effects of all of the tannins and related polyphenols tested in the experiments on DPPH radical were stronger than that of dl-α-tocopherol.