58(P-35) 海洋産抗腫瘍性物質アプリロニンA関連化合物の合成と生物活性(ポスター発表の部)

• 末永 聖武

  筑波大数理物質

• 黒田 武史

  筑波大数理物質

• 半田 知久

  筑波大数理物質

• 宮 沙織

  筑波大数理物質

• 兼松 憲吾

  名大

• 坂倉 彰

  筑波大数理物質

• 山田 靜之

  名大

• 木越 英夫

  筑波大数理物質

• 平田 邦生

  JASRI SPring-8

• 高田 昌樹

  JASRI SPring-8

• 加藤 健一

  JASRI SPring-8

• 村岡 真

  JASRI SPring-8

• 山本 雅貴

  JASRI SPring-8:理研

• 田中 宏志

  島根大総合理工

書誌事項

タイトル別名

• 58(P-35) Synthesis and Biological Activities of Aplyronine A and the Related Compounds

抄録

Aplyronine A (1) is a potent antitumor macrolide isolated from the sea hare Aplysia kurodai, and mycalolide B (2) is a cytotoxic and antifungal macrolide isolated from a sponge of the genus Mycale. These macrolides interact with actin, one of the major proteins in cytoskeleton. We achieved total synthesis of aplyronine A (1) and its analogs and investigated the structure-activity relationships. We improved the synthesis of the side chain portion of aplyronine A (1) by using the Paterson aldol reaction and subsequent stereoselective reduction with Me_4NBH(OAc)_3 as key steps. The synthetic analogs 3 and 4 that only consists of the side chain part of aplyronine A (1) and mycalolide B (2) turned out to exhibit a strong actin depolymerizing activity, considering the size of the molecule. This result revealed that the side chain portion in aplyronine A (1) and mycalolide B (2) was responsible for the potent activity of 1 and 2. Analysis of the interaction of aplyronine analogs, such as 30 and 31, with actin by a photoaffinity labeling method has been carried out. Crystallization and X-ray structure analysis of actin complex with aplyronine A (1) also are in progress.

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 46 (0), 323-328, 2004

  天然有機化合物討論会実行委員会

詳細情報

• CRID: 1390001206078348928
• NII論文ID: 110006682439
• DOI: 10.24496/tennenyuki.46.0_323
• 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