47(P-13) Tomato成熟果実のステロイドアルカロイド配糖体(ポスター発表の部)
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概要
- 論文の詳細を見る
Recently, we reported the first isoaltion of steroidal alkaloid glycosides, Esculeosides A (1) and B (2) from the ripe tomato, Lycopersicon esculentum MILL., fruits. From the pink color type, a spirosoalne-type, Esculeoside A (1), while, from the red color type, a solanocapsine-type, Esculeoside B (2) were obtained. Esculeoside A (1) showed anti-proliferation activity against MCF7 and B16F2F. Moreover, Esculeogenin A (3) showed anti-HSV-1 activity. Successively, in this time, we have characterized the structure of the sapogenol of Esculeoside B (2), named Esculeogenin B (5), as (5S,22S,23R,25S)-22,26-epimino-16β,23-epoxy-3β,23,27-trihydroxycholestane, obtained by enzymatic hydrolysis with β-glucosidase and tomatinase of 2. As minor components, Lycoperoside F (7) corresponding to a 22βN stereo-isomer of 1 and a pregnane glycoside (10) have been isolated and characterized as 3-O-β-lycotetraosyl (5S,22R,23R,25S)- 23-acetoxy-3β,27-dihydroxyspirosolane 27-O-β-D-glucopyranoside and (5α)-pregna-16-en-3β-ol- 20-one 3-0-13-lycotetraoside, respectively. Moreover, interconversion of Isoesculeogenin A (8) into Esculeogenin B (5) has been attained by refluxing with aq. pyridine. In addition, we have found an unique reaction that Esculeogenin A (3) was partially converted to a (5α)-pregna-3β,16β-diol-20-one (9) by refluxing with aq. pyridine. Furthermore, it has been shown that Esculeosides A (1) and B (2) could control AcLDL-induced cholesteryl ester accumulation, suggesting them to have a possibility for preventing atherosclerosis. As regards with this mechanism, based on the fact that the endocytic uptake and degradation of <125>^I-Ac-LDL with human macropharges decreased, it has been suggested that Esculeosides A and B might restrain the appearance of the scavenging receptor.
- 天然有機化合物討論会の論文
- 2004-10-01
著者
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野原 稔弘
熊本大学薬学部
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野原 稔弘
熊本大学 医薬
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野原 稔弘
崇城大薬
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小野 政輝
九州東海大農学部
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野原 稔弘
熊本大薬
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藤原 章雄
熊本大学大学院医学薬学研究部細胞病理学分野
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藤原 章雄
熊本大院医薬研
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松下 さやか
熊本大院医薬研
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吉崎 美穂
熊本大院医薬研
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池田 剛
熊本大院医薬研
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野原 稔弘
熊本大院医薬研
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小野 政輝
九州東海大農
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野原 稔弘
熊本大 大学院 医学薬学研究部
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池田 剛
熊本大院薬
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野原 稔弘
能本大学薬学部
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藤原 章雄
熊本大院薬
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