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

波多野 力 貴良 礼子 安原 多恵子 奥田 拓男

出版者

天然有機化合物討論会実行委員会

雑誌

天然有機化合物討論会講演要旨集

巻号頁・発行日

vol.30, pp.292-299, 1988

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1)Four new hydrolyzable tannins, liquidambin (3), isorugosin A (12), isorugosin B (9) and isorugosin D (13), were isolated from the leaves of Liquidambar formosana. 2) Liquidambin (3), which could be a biogenetic precursor of C-glucosidic tannins, was isolated as an equilibrium mixture. The equilibration was found to be due to hydration of the aldehyde group at C-1 of the glucose residue in 3. 3) Isorugosin D (13), biogenetically producible from two molecules of tellimagrandin II (17), had a valoneoyl group of the orientation different from that of rugosin D (6). Isorugosins A (12) and B (9), monomeric tannins from the same plant, were isomers of rugosins A (4) and B (5) concerning the orientation of valoneoyl group. 4) Rugosins A (4), B (5) and D (6) were absent in L. formosana, and isorugosins A (12), B (9) and D (13) have not been found in Rosa rugosa and Coriaria japonica, which contain 4, 5 and 6. The C-O oxidative coupling in the formation of valoneoyl group in L. formosana, therefore will have been effected by an enzyme different from that of R. rugosa and C. japonica. 5) Cornusiin A, a major component of the fruits of Cornus officinalis, should be formulated as 19, on the basis of the chemical conversion of 19 to isorugosin B (9). Structures of camptothins A and B, which were isolated from the leaves of Camptotheca acuminata, and that of cornusiin C from the Cornus and Camptotheca species, were determined to be 20, 21 and 22, respectively.

著者

木村 善行 奥田 拓道 奥田 拓男 吉田 隆志 波多野 力 有地 滋

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.31, no.7, pp.2501-2506, 1983-07-25

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The effects of various tannins and related compounds on the actions of adrenocorticotropic hormone (ACTH) and insulin in fat cells isolated from rats were investigated. Hydrolyzable tannins such as geraniin, mallotusinic acid, chebulinic acid and chebulagic acid enhanced the ACTH-induced lipolysis at the concentration of 20 μg/ml or 5 μg/ml. On the other hand, these hydrolyzable tannins had no effect on the insulin-stimulated lipogenesis from glucose. Condensed tannins such as Ss-tannin 1 and RSF-tannin H showed weak inhibitory effects on the ACTH-induced lipolysis, while they enhanced the insulin-stimulated lipogenesis from glucose. Based on these results, the relationship between the structures and physiological actions of these tannins is discussed.

著者

奥田 拓男 毛利 和子 寺山 香代子 樋口 恵子 波多野 力

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.99, no.5, pp.543-545, 1979

被引用文献数

10

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Geraniin was isolated from herbs of Geranium carolinianum, G. wilfordii, G. wilfordii var. hastatum, G. sibiricum var. glabrius, G. tripartitum, and G. yoshinoi, and also from root bark of Triadica sebifera. The isolations were improved by application of droplet counter-current chromatography. Hyperin was isolated from G. carolinianum, and quercetin from G. yoshinoi.

著者

木村 善行 奥田 拓道 毛利 和子 奥田 拓男 有地 滋

出版者

公益社団法人 日本栄養・食糧学会

雑誌

日本栄養・食糧学会誌 (ISSN:02873516)

巻号頁・発行日

vol.37, no.3, pp.223-232, 1984-06-12 (Released:2010-02-22)

参考文献数

13

被引用文献数

6 7

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1) コーンオイルに酸素を注入しながら180℃, 1時間加温して過酸化させた後, ラットに強制的に1週間経口投与すると血清中のGOT, GPT中性脂肪の遊離脂肪酸および過酸化脂質の上昇, 肝臓中の総コレステロール, 中性脂肪および過酸化脂質の蓄積が認められた。2) 過酸化コーンオイルとともに緑茶の各分画エキスを日常摂取量の約10~20倍量投与した場合, 体重の増減は見られず, 血清中のGPT, 遊離脂肪酸および過酸化脂質の上昇が軽度抑制され, 肝臓中の中性脂肪の蓄積も軽度抑制された。血清中の総コレステロール, 中性脂肪, 動脈硬化指数, GOTおよび肝臓中の総コレステロール, 過酸化脂質については過酸化コーンオイル投与群に比較して有意な差は認められなかった。3) 過酸化コーンオイル投与ラットにウーロン茶の各分画エキスを日常摂取量の約10~20倍量投与すると, 体重には変化はなく, 血清中の遊離脂肪酸および中性脂肪の上昇が軽度抑制され, 肝臓中の総コレステロールおよび過酸化脂質の蓄積が軽度抑制された。血清中の高比重リポタンパクコレステロール, 過酸化脂質, GOT, GPTおよび肝臓中の中性脂肪については過酸化コーンオイル投与群と比較して有意な差は認められなかった。4) 過酸化コーンオイル投与ラットに紅茶の各分画エキスを日常摂取量の約10~20倍量投与すると, 体重の変化は認められず, 血清中の遊離脂肪酸および過酸化脂質の上昇が軽度抑制された。血清中の高比重リポタンパクコレステロール, 総コレステロール, 中性脂肪, GPTおよび肝臓中の過酸化脂質については過酸化コーンオイル投与群に比較して有意な差は認められなかった。

著者

奥田 拓男 毛利 和子 寺山 香代子 樋口 恵子 波多野 力

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.99, no.5, pp.p543-545, 1979-05

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Geraniin was isolated from herbs of Geranium carolinianum, G. wilfordii, G. wilfordii var. hastatum, G. sibiricum var. glabrius, G. tripartitum, and G. yoshinoi, and also from root bark of Triadica sebifera. The isolations were improved by application of droplet counter-current chromatography. Hyperin was isolated from G. carolinianum, and quercetin from G. yoshinoi.

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.