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)

• 宮下 裕幸

  熊本大院薬

• 甲斐 友樹

  熊本大院薬

• 野原 稔弘

  崇城大薬

• 池田 剛

  熊本大院薬

書誌事項

タイトル別名

• P-68 Synthesis of chacotriosyl derivatives originated from Solanaceous steroidal glycosides having anti-tumor activity(Poster Presentation)

抄録

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.

収録刊行物

• 天然有機化合物討論会講演要旨集

  天然有機化合物討論会講演要旨集 50 (0), 743-748, 2008

  天然有機化合物討論会実行委員会

詳細情報

• CRID: 1390001206078455680
• NII論文ID: 110007066688
• DOI: 10.24496/tennenyuki.50.0_743
• ISSN: 24331856
• 本文言語コード: ja
• データソース種別:
  • JaLC
  • CiNii Articles
• 抄録ライセンスフラグ: 使用不可