Ellagitannin Chemistry

Quideau, Stéphane; Feldman, Ken S.

doi:10.1021/cr940716a

Cited by 264 publications

(208 citation statements)

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“…Masses below m/z 1,217.1 correspond to known pomegranate ellagitannin structures (Table II), such as punicalin (m/z 914.5), pedunculagin (m/z 916.5) and punicalagin (m/z 1,217.1), as described by the work of Tanaka et al 30 -32 The higher masses correspond to structures of oligomeric ellagitannins, in which 2-5 core glucose units are crosslinked by dehydrodigalloyl units (Table II). Tentative structural assignments are based on predictive equations generated using the molecular mass of known ellagitannin monomeric units 33 as shown in Table II …”

Section: Discussionmentioning

confidence: 99%

Anthocyanin‐ and hydrolyzable tannin‐rich pomegranate fruit extract modulates MAPK and NF‐κB pathways and inhibits skin tumorigenesis in CD‐1 mice

Afaq

Saleem

Krueger

et al. 2004

Intl Journal of Cancer

418

305

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Chemoprevention has come of age as an effective cancer control modality; however, the search for novel agent(s) for the armamentarium of cancer chemoprevention continues. We argue that agents capable of intervening at more than one critical pathway in the carcinogenesis process will have greater advantage over other single-target agents. Pomegranate fruit extract (PFE) derived from the tree Punica granatum possesses strong antioxidant and antiinflammatory properties. Pomegranate fruit was extracted with acetone and analyzed based on matrix-assisted laser desorption/ionization time-of-flight mass spectrometry and found to contain anthocyanins, ellagitannins and hydrolyzable tannins. We evaluated whether PFE possesses antitumor-promoting effects. We first determined the effect of topical application of PFE to CD-1 mice against 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced conventional markers and other novel markers of skin tumor promotion. We found that topical application of PFE (2 mg/mouse) 30 min prior to TPA (3.2 nmole/mouse) application on mouse skin afforded significant inhibition, in a time-dependent manner, against TPA-mediated increase in skin edema and hyperplasia, epidermal ornithine decarboxylase (ODC) activity and protein expression of ODC and cyclooxygenase-2. We also found that topical application of PFE resulted in inhibition of TPA-induced phosphorylation of ERK1/2, p38 and JNK1/2, as well as activation of NF-B and IKK␣ and phosphorylation and degradation of I B␣. We next assessed the effect of skin application of PFE on TPA-induced skin tumor promotion in 7,12-dimethylbenz(a)anthracene-initiated CD-1 mouse. The animals pretreated with PFE showed substantially reduced tumor incidence and lower tumor body burden when assessed as total number of tumors per group, percent of mice with tumors and number of tumors per animal as compared to animals that did not receive PFE. In TPA-treated group, 100% of the mice developed tumors at 16 weeks on test, whereas at this time in PFE-treated group, only 30% mice exhibited tumors. Skin application of PFE prior to TPA application also resulted in a significant delay in latency period from 9 to 14 weeks and afforded protection when tumor data were considered in terms of tumor incidence and tumor multiplicity. The results of our study provide clear evidence that PFE possesses antiskintumor-promoting effects in CD-1 mouse. Because PFE is capable of inhibiting conventional as well as novel biomarkers of TPAinduced tumor promotion, it may possess chemopreventive activity in a wide range of tumor models. Thus, an in-depth study to define active agent(s) in PFE capable of affording antitumorpromoting effect is warranted.

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Section: Discussionmentioning

confidence: 99%

Anthocyanin‐ and hydrolyzable tannin‐rich pomegranate fruit extract modulates MAPK and NF‐κB pathways and inhibits skin tumorigenesis in CD‐1 mice

Afaq

Saleem

Krueger

et al. 2004

Intl Journal of Cancer

418

305

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“…ETs are esters of hexahydroxydiphenic acid (HHDP: 6,6 0 -dicarbonyl-2,2 0 ,3,3 0 ,4,4 0 -hexahydroxybiphenyl moiety) and a polyol usually glucose or quinic acid (Quideau & Feldman, 1996). A key feature of ETs is their ability to release the bislactone, EA, which is formed from the hydrolytic release of HHDP esters groups, which undergo rapid, facile and unavoidable lactonization.…”

Section: Hydrolyzable Tannins (Ets Gts and Ea)mentioning

confidence: 99%

Identification of phenolic compounds in strawberries by liquid chromatography electrospray ionization mass spectroscopy

et al. 2006

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Strawberry (Fragaria x ananassa Duch.) fruits contain phenolic compounds that have antioxidant, anticancer, antiatherosclerotic and anti-neurodegenerative properties. Identification of food phenolics is necessary since their nature, size, solubility, degree and position of glycosylation and conjugation influence their absorption, distribution, metabolism and excretion in humans. Freezedried whole strawberry fruit powder and strawberry fruit extracts were analyzed by liquid chromatography electrospray ionization mass spectrometry (LC-ESI-MS) methods. Phenolics were identified as ellagic acid (EA), EA-glycosides, ellagitannins, gallotannins, anthocyanins, flavonols, flavanols and coumaroyl glycosides. The anthocyanidins were pelargonidin and cyanidin, found predominantly as their glucosides and rutinosides. The major flavonol aglycons were quercetin and kaempferol found as their glucuronides and glucosides. LC-ESI-MS/MS methods differentiated EA from quercetin conjugates since both aglycons have identical molecular weights (302 g/mol). The identification of strawberry phenolics is necessary to generate standardized materials for in vitro and in vivo studies and for the authentication of strawberry-based food products.

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“…[1,7] Hundreds of purified ellagitannins have been characterized and biologically evaluated as active constituents of plant extracts used in traditional medicine. [7,8] Yet the potential of ellagitannin-based drugs has so far remained untapped, even though pyrogallol-type biaryl and teraryl units (Scheme 1) confer onto this tannin class rigid and stereochemically defined motifs which are well-suited for specific interactions with proteins. [7,9,10] The work presented herein concerns the formation in red wine of acutissimin A (4 a) and related flavano-ellagitannins from flavan-3-ols and C-glycosidic ellagitannins such as (À)-vescalagin (1 a) and its C-1 epimer (À)-castalagin (1 b) that feature an unusual open-chain glucose core C À C-linked to a galloyl-derived teraryl unit (Scheme 1).…”

mentioning

confidence: 99%

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

et al. 2003

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Ellagitannin Chemistry

Abstract: ContentsI. Introduction 475 A. Structural Description 476 B. Biosynthesis 480 C. Biological Activity 481 D. Problems for Synthesis 483 II. Strategies and Results 483 A.

Cited by 264 publications

References 216 publications

Anthocyanin‐ and hydrolyzable tannin‐rich pomegranate fruit extract modulates MAPK and NF‐κB pathways and inhibits skin tumorigenesis in CD‐1 mice

Anthocyanin‐ and hydrolyzable tannin‐rich pomegranate fruit extract modulates MAPK and NF‐κB pathways and inhibits skin tumorigenesis in CD‐1 mice

Identification of phenolic compounds in strawberries by liquid chromatography electrospray ionization mass spectroscopy

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

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