Structures and Biogenesis of Rhoipteleanins, Ellagitannins Formed by Stereospecific Intermolecular C-C Oxidative Coupling, Isolated from Rhoiptelea chiliantha
Bibliographic Information
- Other Title
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- Structures and Biogenesis of Rhoiptelea
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Abstract
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.
Journal
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- Chemical and Pharmaceutical Bulletin
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Chemical and Pharmaceutical Bulletin 45 (12), 1915-1921, 1997
The Pharmaceutical Society of Japan
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Details 詳細情報について
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- CRID
- 1390282679154121216
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- NII Article ID
- 130003773687
- 110003662819
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- NII Book ID
- AA00602100
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- ISSN
- 13475223
- 00092363
- http://id.crossref.org/issn/00092363
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- NDL BIB ID
- 4371057
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- Text Lang
- en
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- Data Source
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- JaLC
- NDL
- Crossref
- CiNii Articles
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- Abstract License Flag
- Disallowed
