DNA Topoisomerase Inhibitor Acutissimin A and Other Flavano‐Ellagitannins in Red Wine

Quideau, Stéphane; Jourdes, Michaël; Saucier, Cédric; Glories, Yves; Pardon, Patrick; Baudry, Christian

doi:10.1002/anie.200352089

Cited by 79 publications

(56 citation statements)

References 14 publications

(10 reference statements)

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“…The crude product was dissolved in 1 M hydrochloric acid and purified by CC (500 mg of Sephadex LH-20, H 2 O to MeOH) to afford 2 (9.2 mg, 97% yield) as a pale yellow syrup. 1 H NMR, 13 C NMR, HRMS and optical rotation data for 2 were in agreement with those previously reported 57 .…”

Section: Synthesis Of Compound 44supporting

confidence: 90%

“…Furthermore, disorders of the routine patterns in uniting the component parts frequently appear in higher ellagitannins. In addition, the family includes numerous component parts, including overoxidation 8,9 , modifications of the HHDP group 10 , conjugation with other natural constituents [11][12][13] and production of the highly oxygenated diaryl ethers. Among these factors conferring structural diversity, the production of highly oxygenated diaryl ethers, C-O digallates, is the most significant.…”

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confidence: 99%

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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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Section: Synthesis Of Compound 44supporting

confidence: 90%

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confidence: 99%

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

et al. 2014

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“…[48] One report also indicates that both Catechin and Quercetin can reduce with alpha-amylase and subsequently decrease the blood glucose level in mice after oral starch [64] as foregoing is similar to the efficacy results of natural compounds when compared to Acarbose. In one study has demonstrated that many polyphenolic compounds display a role alpha-amylase inhibitory activity [65] such as Catechin and Rutin [14] while Quercetin is bioflavonoid that has been used for relieving hyperglycemia activity to lead glucose homeostasis. [66] The alkaloids exhibited inhibitory activity against alpha-glucosidase, aldose reductase, alpha-amylase, and lipase.…”

Section: Discussionmentioning

confidence: 99%

Potent Natural Inhibitors of Alpha-Glucosidase and Alpha-Amylase against Hyperglycemia <em>in Vitro </em>and <em>in Vivo</em>

Riyaphan¹,

Jhong²,

Tsai³

et al. 2017

Preprint

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“…Hydrolysable tannins are subdivided into gallotannins, derived from gallic acid [2] units linked to a sugar moiety), while condensed tannins are complex polymers, where the building blocks are usually catechins and flavonoids (51). Tannins could cause several effects on the biological system because they are potential metal ion chelators and protein precipitation agents forming insoluble complexes with proteins, as well as biological oxidants (52). Tannic acid and tannin-rich nonalcoholic components of red wine have been shown to reduce serum glucose levels after starch-rich meals in a study of patients with non-insulin dependent diabetes mellitus (53).…”

Section: Phytoconstituents With -Amylase Inhibitory Activitymentioning

confidence: 99%

α-Amylase Inhibitors: A Review of Raw Material and Isolated Compounds from Plant Source

et al. 2012

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-Inhibition of α-amylase, enzyme that plays a role in digestion of starch and glycogen, is considered a strategy for the treatment of disorders in carbohydrate uptake, such as diabetes and obesity, as well as, dental caries and periodontal diseases. Plants are an important source of chemical constituents with potential for inhibition of α-amylase and can be used as therapeutic or functional food sources. A review about crude extracts and isolated compounds from plant source that have been tested for α-amylase inhibitory activity has been done. The analysis of the results shows a variety of crude extracts that present α-amylase inhibitory activity and some of them had relevant activity when compared with controls used in the studies. Amongst the phyto-constituents that have been investigated, flavonoids are one of them that demonstrated the highest inhibitory activities with the potential of inhibition related to number of hydroxyl groups in the molecule of the compound. Several phyto-constituents and plant species as α-amylase inhibitors are being reported in this article. Majority of studies have focused on the anti-amylase phenolic compounds.

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DNA Topoisomerase Inhibitor Acutissimin A and Other Flavano‐Ellagitannins in Red Wine

Cited by 79 publications

References 14 publications

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

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

Potent Natural Inhibitors of Alpha-Glucosidase and Alpha-Amylase against Hyperglycemia <em>in Vitro </em>and <em>in Vivo</em>

α-Amylase Inhibitors: A Review of Raw Material and Isolated Compounds from Plant Source

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