P-68 抗腫瘍活性ステロイド配糖体を構成する糖鎖chacotriose誘導体の合成(ポスター発表の部)
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概要
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We reported a variety of natural steroidal glycosides originated from Solanum plants, and the steroidal glycosides containing a chacotriose (α-L-rhamnopyranosyl-(1→4)-[α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranose) at the oligosaccharide moiety exhibit most potent anti-cancer and anti-herpes activities. In order to investigate the structure-activity relationships of the aglycone parts of chacotriosides, we planed to develop a synthesis method for chacotriosyl glycosides having various aglycones. At first, the protected chacotrioside 4 was synthesized from D-glucose and L-rhamnose in 5 steps 19% yield. Next, some chacotriosyl donors were synthesized from 4, and were glycosylated to some aglycone moieties (diosgenin, cholesterol, cholestanol, glycyrrhetic acid, digitoxigenin) to afford corresponding α- and β-chacotriosyl glycosides (12α-15β). In the process, it was revealed that β-glycosides could be afforded predominatly by using phosphite donor 5, while α-glycosides were obtained mainly by using a trichloroacetimidate donor 6. In addition, allyl chacotrioside 16 was simply converted to various types of double-chain neoglycolipids that mimicked glycosyl ceramides in 3 steps. In cytotoxicity tests using A549, HepG2, RAW and LLC-PK1 cell lines, chacotriosyl glycosides containing cholesterol and cholestanol at the aglycone part exhibited potent activities as same as dioscin 7 and 5-FU. Compared with the form of glycosidic bond (α/β) possessing the same aglycone, the β-glycoside tended to show more potent effect rather than α-glycoside. Furthermore, only chacotriose moiety and aglycone parts did not exhibit activity. Among these obtained chacotriosyl glycolipids, only glycolipid 24 exhibited the potent activity as same as dioscin.
- 天然有機化合物討論会の論文
- 2008-09-01
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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野原 稔弘
熊本大薬
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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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宮下 裕幸
熊本大院薬
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甲斐 友樹
熊本大院薬
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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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