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Nupharanin, the first ellagitannin with 1,4-dehydrohexahydroxydiphenoyl-α-d-glucopyranose from Nuphar japonicum


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Title: Nupharanin, the first ellagitannin with 1,4-dehydrohexahydroxydiphenoyl-α-d-glucopyranose from Nuphar japonicum
Authors: Orejola, Joanna J. / Era, Manami / Matsuo, Yosuke / Saito, Yoshinori / Tanaka, Takashi
Issue Date: 18-Apr-2020
Publisher: Elsevier Ltd.
Citation: Tetrahedron, 76(21), art.no.131204; 2020
Abstract: Nupharanin (1), the first ellagitannin with dehydrohexahydroxydiphenoyl esters at the 1,4-positions of a-D-glucose, was isolated from the fresh rhizome of Nuphar japonicum. Based on spectroscopic evidence,the structure was determined to be 1,4-(S)-dehydrohexahydroxydiphenoyl-2-galloyl-3,6-(R)-hexahydroxydiphenoyl- a-D-glucopyranose. The structure was supported by spectroscopic studies of acetonyl derivatives of 1 and its partial hydrolysate. In addition, unusual oxidative cleavage of the hydrated cyclohexenetrione ring of 1 was observed on moderate heating at 50 C in pH 6 buffer.
Keywords: Nuphar japonicum / Nymphaceae / Nupharanin / Dehydrohexahydroxydiphenoyl / Ellagitannin
URI: http://hdl.handle.net/10069/39991
ISSN: 00404020
DOI: 10.1016/j.tet.2020.131204
Rights: © 2020 Elsevier Ltd. This manuscript version is made available under the CC-BY-NC-ND 4.0 license http://creativecommons.org/licenses/by-nc-nd/4.0/
Type: Journal Article
Text Version: author
Appears in Collections:Articles in academic journal

Citable URI : http://hdl.handle.net/10069/39991

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