Synthesis of ellagitannin natural products

Pouységu, Laurent; Deffieux, Denis; Malik, G. M.; Natangelo, Anna; Quideau, Stéphane

doi:10.1039/c0np00058b

Cited by 78 publications

(45 citation statements)

References 90 publications

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“…4,9) Due to their pharmaceutical potentials, extensive efforts have been devoted to their synthesis. 4,9) The structure is basically composed of a central sugar core, typically D-glucose, to which are esterified gallic acid (3,4,5-trihydroxybenzoic acid) and hexahydroxy diphenoic acid (HHDP). Among ellagitannins, we chose tellimagrandin II (1) (eugeniin), 10) and its regioisomeric natural product, pterocarinin C (2) 11) ( Fig.…”

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confidence: 99%

Total Synthesis of Ellagitannins <i>via</i> Sequential Site-Selective Functionalization of Unprotected D-Glucose

et al. 2017

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A short-step total synthesis of the natural glycosides pterocarinin C and tellimagrandin II (eugeniin) has been performed by sequential and site-selective functionalization of free hydroxy groups of unprotected Dglucose. The key reactions are β-selective glycosidation of a gallic acid derivative using unprotected D-glucose as a glycosyl donor and catalyst-controlled site-selective introduction of a galloyl group into the inherently less reactive hydroxy group of the glucoside.

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Total Synthesis of Ellagitannins <i>via</i> Sequential Site-Selective Functionalization of Unprotected D-Glucose

et al. 2017

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“…Gallotannins have a core of β -penta-O-galloyl-D-glucopyranose to which several other galloyl ester groups are linked despite fashion. Ellagitannins are characterized by the presence of two C–C-coupled galloyl ester groups at the 2,3-and/or 4,6-positions of a 4 C1-glucopyranose [3]. …”

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confidence: 99%

Sweet Chestnut (Castanea sativaMill.) Bark Extract: Cardiovascular Activity and Myocyte Protection against Oxidative Damage

Chiarini

Micucci

Malaguti

et al. 2013

Oxidative Medicine and Cellular Longevity

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This work was aimed at evaluating the cardioprotective effects of Castanea sativa Mill. (CSM) bark extract characterized in its phenolic composition by HPLC-DAD-MS analysis. The study was performed using primary cultures of neonatal rat cardiomyocytes to investigate the antioxidant and cytoprotective effects of CSM bark extract and isolated guinea pig left and right atria, left papillary muscle, and aorta to evaluate its direct effect on cholinergic and adrenergic response. In cultured cardiomyocytes the CSM bark extract reduced intracellular reactive oxygen species formation and improved cell viability following oxidative stress in dose-dependent manner. Moreover, the extract decreased the contraction induced by noradrenaline (1 μM) in guinea pig aortic strips and induced transient negative chronotropic and positive inotropic effects without involvement of cholinergic or adrenergic receptors in the guinea pig atria. Our results indicate that CSM bark extract exhibits antioxidant activity and might induce cardioprotective effect.

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“…The family of ellagitannins, which consists of bioactivity-and structure-rich polyphenols 5,6 , has been found to contain more than 1,000 natural products to date 7 . The most basic ellagitannins consist of a glucose core with esterified galloyl and hexahydroxydiphenoyl (HHDP) groups (Fig.…”

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A unified strategy for the synthesis of highly oxygenated diaryl ethers featured in ellagitannins

et al. 2014

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Ellagitannins are a family of polyphenols containing more than 1,000 natural products. Nearly 40% of these compounds contain a highly oxygenated diaryl ether that is one of the most critical elements to their structural diversity. Here, we report a unified strategy for the synthesis of highly oxygenated diaryl ethers featured in ellagitannins. The strategy involves oxa-Michael addition of phenols to an orthoquinone building block, with subsequent elimination and reductive aromatization. The design of the building block-a halogenated orthoquinone monoketal of gallal-reduces the usual instability of orthoquinone and controls addition/elimination. Reductive aromatization is achieved with perfect chemoselectivity in the presence of other reducible functional groups. This strategy enables the synthesis of different diaryl ethers. The first total synthesis of a natural ellagitannin bearing a diaryl ethers is performed to demonstrate that the strategy increases the number of synthetically available ellagitannins.

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Synthesis of ellagitannin natural products

Cited by 78 publications

References 90 publications

Total Synthesis of Ellagitannins <i>via</i> Sequential Site-Selective Functionalization of Unprotected D-Glucose

Total Synthesis of Ellagitannins <i>via</i> Sequential Site-Selective Functionalization of Unprotected D-Glucose

Sweet Chestnut (Castanea sativaMill.) Bark Extract: Cardiovascular Activity and Myocyte Protection against Oxidative Damage

A unified strategy for the synthesis of highly oxygenated diaryl ethers featured in ellagitannins

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