Pharmacologically Active Ellagitannins from Terminalia myriocarpa

Marzouk, Mohamed; El‐Toumy, Sayed A.; Moharram, Fatma A.

doi:10.1055/s-2002-32549

Cited by 35 publications

(19 citation statements)

References 20 publications

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“…The suppressive effect of WP at 200 mg/kg was nearly comparable to that of curcumin, which has been previously reported to be effective in this model (20,21). Several ellagitannins of pomegranate such as methyl (S)-flavogallonate (22), punicalagin (22,23), and punicalin (23) have been reported to be hepatoprotective in a CCl 4 -induced rat liver injury model. WP contains ellagitannins (Figure 1), and thus, the hepatoprotective activity in the same model found in this study is in concordance with the previous findings.…”

Section: Discussionmentioning

confidence: 99%

Walnut Polyphenols Prevent Liver Damage Induced by Carbon Tetrachloride and d-Galactosamine: Hepatoprotective Hydrolyzable Tannins in the Kernel Pellicles of Walnut

Shimoda

Tanaka

Kikuchi

et al. 2008

J. Agric. Food Chem.

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The polyphenol-rich fraction (WP, 45% polyphenol) prepared from the kernel pellicles of walnuts was assessed for its hepatoprotective effect in mice. A single oral administration of WP (200 mg/kg) significantly suppressed serum glutamic oxaloacetic transaminase (GOT) and glutamic pyruvic transaminase (GPT) elevation in liver injury induced by carbon tetrachloride (CCl 4), while it did not suppress d-galactosamine (GalN)-induced liver injury. In order to identify the active principles in WP, we examined individual constituents for the protective effect on cell damage induced by CCl 4 and d-GalN in primary cultured rat hepatocytes. WP was effective against both CCl 4- and d-GalN-induced hepatocyte damages. Among the constituents, only ellagitannins with a galloylated glucopyranose core, such as tellimagrandins I, II, and rugosin C, suppressed CCl 4-induced hepatocyte damage significantly. Most of the ellagitannins including tellimagrandin I and 2,3- O-hexahydroxydiphenoylglucose exhibited remarkable inhibitory effect against d-GalN-induced damage. Telliamgrandin I especially completely suppressed both CCl 4- and d-GalN-induced cell damage, and thus is likely the principal constituent for the hepatoprotective effect of WP.

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Section: Discussionmentioning

confidence: 99%

Walnut Polyphenols Prevent Liver Damage Induced by Carbon Tetrachloride and d-Galactosamine: Hepatoprotective Hydrolyzable Tannins in the Kernel Pellicles of Walnut

Shimoda

Tanaka

Kikuchi

et al. 2008

J. Agric. Food Chem.

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“…For example, punicalagin ( 9 ) and punicalin ( 10 ) from Terminalia species exhibited inhibitory effects on hepatotoxicity induced by acetaminophen [75] and CCl 4 [38]. Other activities associated with the antioxidative effects of punicalagin ( 9 ) include the suppression of bleomycin-induced genotoxicity in cultured Chinese hamster ovary cells [76] and of the proliferation of H-ras-transformed NIH3T3 cells.…”

Section: Biological Activities Of Ellagitannins Found In the Myrtalesmentioning

confidence: 99%

Structural Features and Biological Properties of Ellagitannins in Some Plant Families of the Order Myrtales

Yoshida

Amakura

Yoshimura

2010

IJMS

134

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Plant tannins, including hydrolysable and condensed varieties, are well known antioxidants in medicinal plants, foods, and edible fruits. Their diverse biological properties and potential for disease prevention have been demonstrated by various in vitro and in vivo assays. A number of ellagitannins, the largest group of hydrolysable tannins, have been isolated from dicotyledoneous angiosperms and characterized. This diverse class of tannins is sub-grouped into simple ellagitannins, C-glycosidic ellagitannins, complex tannins (condensates of C-glycosidic tannins with flavan-3-ol), and oligomers up to pentamers. This review outlines and describes the chemotaxonomic significance of structural features in various types of ellagitannins found in plants belonging to the Myrtaceae, Onagraceae, and Melastomataceae families, which are all included in the order Myrtales. Any biological activities that have been reported, including antitumor and antibacterial effects as well as enzyme inhibition, are also reviewed.

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“…The loss of the two oxygen molecules {483-451} at MS 3 , gave a fragmentation ion at m/z 433. Also, the spectra was devoid of the fragment of [M-H-CO2] -, which corresponds to a methyl ester molecule [53]. Therefore, and according to previous investigations [36,54], compound (5)…”

Section: Lc-ms and Lc-ms/ms Resultsmentioning

confidence: 66%

LC-MS/MS Tandem Mass Spectrometry for Analysis of Phenolic Compounds and Pentacyclic Triterpenes in Antifungal Extracts of <em>Terminalia brownii</em> (Fresen)

Salih

Fyhrquist

Abdalla

et al. 2017

Preprint

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Decoctions, macerations and fumigations of the stem bark and wood of Terminalia brownii Fresen. are used in traditional medicine for fungal infections and as pesticides on field crops and in traditional granaries in Sudan. In addition, T. brownii is commonly used for protecting wooden houses and furniture. Therefore, using agar disc diffusion and macrodilution methods, eight extracts of various polarities from the stem wood and bark were screened for their growth inhibitory effects against filamentous fungi commonly causing fruit, vegetable and grain decay, as well as infections in the immunocompromised host. Ethyl acetate extracts of the stem wood and bark gave the best antifungal activities, with MIC values of 250 µg/ml against Nattrassia mangiferae and Fusarium verticillioides, and 500 µg/ml against Aspergillus niger and Aspergillus flavus. Aqueous extracts gave almost as potent effects as the ethyl acetate extracts against the Aspergillus and Fusarium strains, and were slightly more active than the ethyl acetate extracts against Nattrassia mangiferae. Thin layer chromatography, RP-HPLC-DAD and tandem mass spectrometry (LC-MS/MS), were employed to identify the chemical constituents in the ethyl acetate fractions of the stem bark and wood. The stem bark and wood were found to have a similar qualitative composition of polyphenols and triterpenoids, but differed quantitatively from each other. The stilbene derivatives, cis- (3) and trans- (4) resveratrol-3-O-β-galloylglucoside, were identified for the first time in T. brownii. Moreover, methyl-(S)-flavogallonate (5), quercetin-7-β-O-di-glucoside (8), quercetin-7-O-galloyl-glucoside (10), naringenin-4`-methoxy-7-pyranoside (7), 5,6-dihydroxy-3`,4`,7-tri-methoxy flavone (12), gallagic acid dilactone (terminalin) (6), a corilagin derivative (9) and two oleanane type triterpenoids (1) and (2) were characterized. Our results justify the traditional uses of macerations and decoctions of T. brownii stem wood and bark for crop and wood protection and demonstrate that standardized extracts could have uses for the eco-friendly control of plant pathogenic fungi in African agroforestry systems. Likewise, our results justify the traditional uses of these preparations for the treatment of skin infections caused by filamentous fungi.

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Pharmacologically Active Ellagitannins from Terminalia myriocarpa

Cited by 35 publications

References 20 publications

Walnut Polyphenols Prevent Liver Damage Induced by Carbon Tetrachloride and d-Galactosamine: Hepatoprotective Hydrolyzable Tannins in the Kernel Pellicles of Walnut

Walnut Polyphenols Prevent Liver Damage Induced by Carbon Tetrachloride and d-Galactosamine: Hepatoprotective Hydrolyzable Tannins in the Kernel Pellicles of Walnut

Structural Features and Biological Properties of Ellagitannins in Some Plant Families of the Order Myrtales

LC-MS/MS Tandem Mass Spectrometry for Analysis of Phenolic Compounds and Pentacyclic Triterpenes in Antifungal Extracts of <em>Terminalia brownii</em> (Fresen)

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