Structural revisions of macrocyclic ellagitannin dimers bridged by two hexahydroxydiphenoyl groups

IF 2.2 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron Pub Date : 2025-05-27 DOI:10.1016/j.tet.2025.134751

Ryo Ohtsuka, Yosuke Matsuo, Yoshinori Saito, Koji Yamada, Takashi Tanaka, Fumika Yakushiji

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Abstract

Ellagitannin dimers, 1,1′;2,2′-diHHDP-diglucose and 3,3′;4,4′-diHHDP-6,6′-digalloyl-diglucose, were recently isolated from the wood of the sweet chestnut (Castanea sativa Mill.). These compounds were originally reported to possess unprecedented macrocyclic dimeric structures bridged by two hexahydroxydiphenoyl (HHDP) groups. However, a reinvestigation of their spectroscopic data revealed that these compounds correspond to known ellagitannin monomers, namely 2,3-O-(S_a)-HHDP-d-glucopyranose and gemin D (3-O-galloyl-4,6-O-(S_a)-HHDP-d-glucopyranose), respectively. A comparison of the originally reported NMR data for 1,1′;2,2′-diHHDP-diglucose and 3,3′;4,4′-diHHDP-6,6′-digalloyl-diglucose with those of authentic 2,3-O-(S_a)-HHDP-d-glucopyranose and gemin D, combined with DFT-based NMR chemical shift calculations, unequivocally confirmed these structural revisions.

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两个六羟基二酚基团桥接的大环鞣花单宁二聚体的结构修正

鞣花丹素二聚体1,1 ';2,2 ' -二羟色胺-二葡萄糖和3,3 ';4,4 ' -二羟色胺-6,6 ' -二丙二糖是最近从甜栗木中分离得到的。这些化合物最初被报道具有前所未有的由两个六羟基二酚（HHDP）基团桥接的大环二聚体结构。然而，对他们的光谱数据的重新研究表明，这些化合物分别对应于已知的鞣花单宁单体，即2,3- o -(Sa)- hhp - D -葡萄糖醛酸和gemin D （3-O-没食子酰基-4,6- o -(Sa)- hhp - D -葡萄糖醛酸）。将最初报道的1,1 ';2,2 ' - dihhdp -二葡萄糖和3,3 ';4,4 ' - dihhdp -6,6 ' -二醛基二葡萄糖与真实的2,3- o -(Sa)- hhdp - D -葡萄糖和gemin D的核磁共振数据进行比较，结合基于dft的核磁共振化学位移计算，明确证实了这些结构修正。

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来源期刊

Tetrahedron 化学-有机化学

CiteScore

3.90

自引率

4.80%

发文量

439

审稿时长

34 days

期刊介绍： Tetrahedron publishes full accounts of research having outstanding significance in the broad field of organic chemistry and its related disciplines, such as organic materials and bio-organic chemistry. Regular papers in Tetrahedron are expected to represent detailed accounts of an original study having substantially greater scope and details than that found in a communication, as published in Tetrahedron Letters. Tetrahedron also publishes thematic collections of papers as special issues and ''Reports'', commissioned in-depth reviews providing a comprehensive overview of a research area.