Structures and Biogenesis of Rhoipteleanins, Ellagitannins Formed by Stereospecific Intermolecular C-C Oxidative Coupling, Isolated from Rhoiptelea chiliantha

• TANAKA Takashi

• JIANG Zhi-Hong

• KOUNO Isao

書誌事項

タイトル別名

• Structures and Biogenesis of Rhoiptelea

抄録

Seven novel ellagitannins named rhoipteleanin A-G were isolated from the fruits of Rhoiptelea chiliantha and their structures were unequivocally established on the basis of spectroscopic and chemical evidence. In the molecules of rhoipteleanin A-F, (S, S)-flavogallonyl esters spanned two glucopyranose moieties; hence, these tannins represent the first dimeric ellagitannins generated by stereospecific intermolecular C-C oxidative coupling between the galloyl and hexahydroxydiphenoyl groups. The change in the ¹H-NMR chemical shifts of specific proton signals of 1(β)-O-galloylpedunculagin, the biogenetic precursor of rhoipteleanin A, in dueterium oxide at various concentrations suggested that the stereochemically regulated hydrophobic interaction between two molecules of the precursor restricts the intermolecular C-C coupling to S-biphenyl bond formation.

収録刊行物

• ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ

  ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ 45 (12), 1915-1921, 1997

  公益社団法人 日本薬学会

キーワード

• tannin
• Rhoiptelea chiliantha
• Rhoipteleaceae
• polyhenol
• hydrophobic association

詳細情報

• CRID: 1390282679154121216
• NII論文ID: 130003773687
• NII論文ID: 110003662819
• NII書誌ID: AA00602100
• DOI: 10.1248/cpb.45.1915
• ISSN: 13475223
• ISSN: 00092363
• ISSN: http://id.crossref.org/issn/00092363
• NDL書誌ID: 4371057
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I4371057
• Web Site: http://www.jstage.jst.go.jp/article/cpb1958/45/12/45_12_1915/_pdf
• 本文言語コード: en
• データソース種別:
  • JaLC
  • NDL
  • Crossref
  • CiNii Articles
• 抄録ライセンスフラグ: 使用不可