Synthesis of Enantiomerically Pure Unusual Ellagitannins 1,4,6-Tri-O-galloyl-2,3-(R)-hexahydroxydiphenoyl-β-<scp>d</scp>-glucopyranoside and 4,6-Di-O-galloyl-2,3-(R)-hexahydroxydiphenoyl-<scp>d</scp>-glucoside. The Proposed Chemical Structures for Cercidinin A and B Must Be Revised

Khanbabaee, Karamali; Lötzerich, Kerstin

doi:10.1021/jo9805302

Cited by 31 publications

(22 citation statements)

References 17 publications

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“…also took advantage of this strategy to synthesize unusual ( R )‐HHDP‐based ellagitannins such as pariin M and mahtabin A (Figure 22). 157e More recently, they achieved two other total syntheses of pedunculagin (Figure 22), the bis‐( S )‐HHDP‐bearing ellagitannin first synthesized by the Feldman research group,154d by relying on either a stepwise or a one‐step twofold HHDP bisesterification strategy 157f…”

Section: How To Access Polyphenols?mentioning

confidence: 99%

Plant Polyphenols: Chemical Properties, Biological Activities, and Synthesis

et al. 2011

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Eating five servings of fruits and vegetables per day! This is what is highly recommended and heavily advertised nowadays to the general public to stay fit and healthy! Drinking green tea on a regular basis, eating chocolate from time to time, as well as savoring a couple of glasses of red wine per day have been claimed to increase life expectancy even further! Why? The answer is in fact still under scientific scrutiny, but a particular class of compounds naturally occurring in fruits and vegetables is considered to be crucial for the expression of such human health benefits: the polyphenols! What are these plant products really? What are their physicochemical properties? How do they express their biological activity? Are they really valuable for disease prevention? Can they be used to develop new pharmaceutical drugs? What recent progress has been made toward their preparation by organic synthesis? This Review gives answers from a chemical perspective, summarizes the state of the art, and highlights the most significant advances in the field of polyphenol research.

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Section: How To Access Polyphenols?mentioning

confidence: 99%

Plant Polyphenols: Chemical Properties, Biological Activities, and Synthesis

et al. 2011

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“…Et ZUCC by Nishioka and first given the structures (a R )- 16 and (a R )- 17 ( Figure 9 ), respectively [ 38 ]. Khanbabaee synthesized (a R )- 16 and (a R )- 17 in 1998, but the synthesized compounds were different from natural cercidinin A and B [ 39 ]. Following the result, Kouno revised the structure to 18 [ 40 ].…”

Section: Structural Revision In Ellagitanninsmentioning

confidence: 99%

Structural Revisions in Natural Ellagitannins

et al. 2018

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Ellagitannins are literally a class of tannins. Triggered by the oxidation of the phenolic parts on β-pentagalloyl-d-glucose, ellagitannins are generated through various structural conversions, such as the coupling of the phenolic parts, oxidation to highly complex structures, and the formation of dimer and lager analogs, which expand the structural diversity. To date, more than 1000 natural ellagitannins have been identified. Since these phenolic compounds exhibit a variety of biological activities, ellagitannins have potential applications in medicine and health enhancement. Within the context of identifying suitable applications, considerations need to be based on correct structural features. This review describes the structural revisions of 32 natural ellagitannins, namely alnusiin; alnusnin A and B; castalagin; castalin; casuarinin; cercidinin A and B; chebulagic acid; chebulinic acid; corilagin; geraniin; isoterchebin; nobotanin B, C, E, G, H, I, J, and K; punicalagin; punicalin; punigluconin; roxbin B; sanguiin H-2, H-3, and H-6; stachyurin; terchebin; vescalagin; and vescalin. The major focus is on the outline of the initial structural determination, on the processes to find the errors in the structure, and on the methods for the revision of the structure.

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“…Mit der gleichen Strategie synthetisierte die Gruppe von Khanbabaee auch ungewöhnliche Ellagtannine mit R ‐HHDP‐Einheiten wie Pariin M und Mahtabin A (Abbildung 22). 157e Später gelang ihnen eine weitere Totalsynthese des Ellagtannins Pedunculagin mit Bis‐ S ‐HHDP‐Einheiten (Abbildung 22), das zuerst von der Feldman‐Gruppe synthetisiert worden war 154d. Sie wählten hierfür entweder eine stufenweise oder eine einstufige Zweifachveresterung von HHDP‐Einheiten 157f.…”

Section: Wie Kommt Man Zu Polyphenolen?unclassified

Pflanzliche Polyphenole: chemische Eigenschaften, biologische Aktivität und Synthese

et al. 2011

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Fünf Portionen Obst und Gemüse am Tag! Das ist nach heutigen Maßgaben nötig, um fit und gesund zu bleiben, das wird überall empfohlen und ebenso heftig beworben. Regelmäßig grüner Tee, ab und zu Schokolade sowie der Genuss von ein paar Gläschen Rotwein am Tag sollen zusätzlich lebensverlängernd wirken. Warum? Eine vollständige Antwort darauf kann die Wissenschaft noch nicht geben, aber eine bestimmte Klasse von natürlichen Substanzen, die in Obst und Gemüse vorkommt, gilt allgemein als besonders gesundheitsfördernd: die Polyphenole! Was aber sind diese pflanzlichen Stoffe genau? Welche physikalisch‐chemischen Eigenschaften haben sie? Wie entfalten sie ihre biologische Wirkung? Können sie wirklich der Vorbeugung von Krankheiten dienen? Können aus ihnen neue Arzneimittel entwickelt werden? Wie weit ist die organische Synthese, um sie herzustellen? Dieser Aufsatz gibt einige Antwort aus der chemischen Perspektive, fasst den aktuellen Stand der Dinge zusammen und stellt die wichtigsten Fortschritte in der Polyphenolforschung vor.

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Synthesis of Enantiomerically Pure Unusual Ellagitannins 1,4,6-Tri-O-galloyl-2,3-(R)-hexahydroxydiphenoyl-β-d-glucopyranoside and 4,6-Di-O-galloyl-2,3-(R)-hexahydroxydiphenoyl-d-glucoside. The Proposed Chemical Structures for Cercidinin A and B Must Be Revised

Cited by 31 publications

References 17 publications

Plant Polyphenols: Chemical Properties, Biological Activities, and Synthesis

Plant Polyphenols: Chemical Properties, Biological Activities, and Synthesis

Structural Revisions in Natural Ellagitannins

Pflanzliche Polyphenole: chemische Eigenschaften, biologische Aktivität und Synthese

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