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New Dimeric Phenolic Conjugates from the Wood of Tamarix tetragyna

  • Hussein, Sahar A.M.
    • Natural Product Sciences
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    • v.3 no.2
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    • pp.127-134
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    • 1997
  • Two new dimeric phenolic conjugates, 2,3-di-O-dehydrodigallicmonocarboxyl-$({\alpha},{\beta})$-$^4C_1$-glucopyranose and ellagic acid 3,3'-dimethylether-4-0-$SO_3K$ were isolated from the debarked heart wood of Tamarix tetragyna (Tamaricaceae) along with the known phenolic compounds, isoferulic acid, ferulic acid, gallic acid, gallic acid 4-methyl ether, syringic acid, ellagic acid 3,3'-dimethyl ether and ellagic acid. All structures were determined mostly by ESI-MS, ID and 2D-NMR spectroscopy.

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Ellagic acid, a functional food component, ameliorates functionality of reverse cholesterol transport in murine model of atherosclerosis

  • Sin-Hye Park;Min-Kyung Kang;Dong Yeon Kim;Soon Sung Lim;Il-Jun Kang;Young-Hee Kang
    • Nutrition Research and Practice
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    • v.18 no.2
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    • pp.194-209
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    • 2024
  • BACKGROUND/OBJECTIVES: High levels of plasma low-density lipoprotein (LDL) cholesterol are an important determinant of atherosclerotic lesion formation. The disruption of cholesterol efflux or reverse cholesterol transport (RCT) in peripheral tissues and macrophages may promote atherogenesis. The aim of the current study was to examine whether bioactive ellagic acid, a functional food component, improved RCT functionality and high-density lipoprotein (HDL) function in diet-induced atherogenesis of apolipoproteins E (apoE) knockout (KO) mice. MATERIALS/METHODS: Wild type mice and apoE KO mice were fed a high-cholesterol Paigen diet for 10 weeks to induce hypercholesterolemia and atherosclerosis, and concomitantly received 10 mg/kg ellagic acid via gavage. RESULTS: Supplying ellagic acid enhanced induction of apoE and ATP-binding cassette (ABC) transporter G1 in oxidized LDL-exposed macrophages, facilitating cholesterol efflux associated with RCT. Oral administration of ellagic acid to apoE KO mice fed on Paigen diet improved hypercholesterolemia with reduced atherogenic index. This compound enhanced the expression of ABC transporters in peritoneal macrophages isolated from apoE KO mice fed on Paigen diet, indicating increased cholesterol efflux. Plasma levels of cholesterol ester transport protein and phospholipid transport protein involved in RCT were elevated in mice lack of apoE gene, which was substantially reduced by supplementing ellagic acid to Paigen diet-fed mice. In addition, ellagic acid attenuated hepatic lipid accumulation in apoE KO mice, evidenced by staining of hematoxylin and eosin and oil red O. Furthermore, the supplementation of 10 mg/kg ellagic acid favorably influenced the transcriptional levels of hepatic LDL receptor and scavenger receptor-B1 in Paigen diet-fed apoE KO mice. CONCLUSION: Ellagic acid may be an athero-protective dietary compound encumbering diet-induced atherogenesis though improving the RCT functionality.

Dietary ellagic acid blocks inflammation-associated atherosclerotic plaque formation in cholesterol-fed apoE-deficient mice

  • Sin-Hye Park;Min-Kyung Kang;Dong Yeon Kim;Soon Sung Lim;Young-Hee Kang
    • Nutrition Research and Practice
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    • v.18 no.5
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    • pp.617-632
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    • 2024
  • BACKGROUND/OBJECTIVES: Atherosclerosis particularly due to high circulating level of low-density lipoprotein is a major cause of cardiovascular diseases. Ellagic acid is a natural polyphenolic compound rich in pomegranates and berries. Our previous study showed that ellagic acid improved functionality of reverse cholesterol transport in murine model of atherosclerosis. The aim of this study is to investigate whether ellagic acid inhibited inflammation-associated atherosclerotic plaque formation in cholesterol-fed apolipoprotein E (apoE)-knockout (KO) mice. MATERIALS/METHODS: Wild type mice and apoE-KO mice were fed a cholesterol-rich Paigen diet for 10 weeks to induce severe atherosclerosis. Concurrently, 10 mg/kg ellagic acid was orally administered to the apoE-KO mice. Plaque lesion formation and lipid deposition were examined by staining with hematoxylin and eosin, Sudan IV and oil red O. RESULTS: The plasma leukocyte profile of cholesterol-fed mice was not altered by apoE deficiency. Oral administration of ellagic acid attenuated plaque lesion formation and lipid deposition in the aorta tree of apoE-KO mice. Ellagic acid substantially reduced plasma levels of soluble vascular cell adhesion molecule and interferon-γ in Paigen diet-fed apoE-KO mice. When 10 mg/kg ellagic acid was administered to cholesterol-fed apoE-KO mice, the levels of CD68 and MCP-1 were strongly reduced in aorta vessels. The protein expression level of nitric oxide synthase-2 (NOS2) in the aorta was highly enhanced by supplementation of ellagic acid to apoE-KO mice, but the expression level of heme oxygenase-1 (HO-1) in the aorta was reduced. Furthermore, ellagic acid diminished the increased aorta expression of the inflammatory adhesion molecules in cholesterol-fed apoE-KO mice. The treatment of ellagic acid inhibited the scavenger receptor-B1 expression in the aorta of apoE-KO mice, while the cholesterol efflux-related transporters were not significantly changed. CONCLUSION: These results suggest that ellagic acid may be an atheroprotective compound by attenuating apoE deficiency-induced vascular inflammation and reducing atherosclerotic plaque lesion formation.

Ellagic Acid Exerts Anti-proliferation Effects via Modulation of Tgf-Β/Smad3 Signaling in MCF-7 Breast Cancer Cells

  • Zhang, Tao;Chen, Hong-Sheng;Wang, Li-Feng;Bai, Ming-Han;Wang, Yi-Chong;Jiang, Xiao-Feng;Liu, Ming
    • Asian Pacific Journal of Cancer Prevention
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    • v.15 no.1
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    • pp.273-276
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    • 2014
  • Ellagic acid has been shown to inhibit tumor cell growth. However, the underlying molecular mechanisms remain elusive. In this study, our aim was to investigate whether ellagic acid inhibits the proliferation of MCF-7 human breast cancer cells via regulation of the TGF-${\beta}$/Smad3 signaling pathway. MCF-7 breast cancer cells were transfected with pEGFP-C3 or pEGFP-C3/Smad3 plasmids, and treated with ellagic acid alone or in combination with SIS3, a specific inhibitor of Smad3 phosphorylation. Cell proliferation was assessed by MTT assay and the cell cycle was detected by flow cytometry. Moreover, gene expression was detected by RT-PCR, real-time PCR and Western blot analysis. The MTT assay showed that SIS3 attenuated the inhibitory activity of ellagic acid on the proliferation of MCF-7 cells. Flow cytometry revealed that ellagic acid induced G0/G1 cell cycle arrest which was mitigated by SIS3. Moreover, SIS3 reversed the effects of ellagic acid on the expression of downstream targets of the TGF-${\beta}$/Smad3 pathway. In conclusion, ellagic acid leads to decreased phosphorylation of RB proteins mainly through modulation of the TGF-${\beta}$/Smad3 pathway, and thereby inhibits the proliferation of MCF-7 breast cancer cells.

Modifying Effects of Ellagic Acid in Food on Carcinogenesis (식품 중 Ellagic acid의 발암수식효과)

  • 장동덕;신동환;홍충만;조재천;한정희
    • Journal of Food Hygiene and Safety
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    • v.13 no.1
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    • pp.29-33
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    • 1998
  • The effect of ellagic acid (EA) on hepatocarcinogenesis induced by diethylnitrosamine (DEN), and promoted by phenobarbital (PB), and hepatectomized partially was investigated in male Wi star rats. All rats were injected 200 mg of DEN intraperitoneally, received 0.05 % of PB in drinking water at week 2, and hepatectomized 2/3 of liver at week 3. Rats of group 2, 3 and 4 were fed diet containing 400ppm EA for 1 week before DEN administration, for 9 weeks from beginning of experiment to sacrifice and for 6 weeks from PB treatment to sacrifice respectively. Rats of group 5, 6 and 7 were fed 800 ppm EA in the same manner as group 2, 3 and 4. Animals were killed at 8 weeks after DEN administration. The number and area of preneoplastic lesions were quantified the glutathione-S-transferase placental-form (GST-P) positive foci using immunohistochemical method. Decrease of number and area of the positive foci was observed in the rats fed 400 ppm EA for 9 weeks. In addition, the reduction of the foci can examine in all group fed 800 ppm EA. In conclusion, EA inhibited the hepatocarcinogenesis induced by DEN when it was administrated 800 ppm.

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(PIM-co-Ellagic Acid)-based Copolymer Membranes for High Performance CO2 Separation ((PIM-co-Ellagic Acid)-기반의 이산화탄소 분리막의 개발)

  • Hossain, Iqubal;Husna, Asmaul;Kim, Dongyoung;Kim, Tae-Hyun
    • Membrane Journal
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    • v.30 no.6
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    • pp.420-432
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    • 2020
  • Random copolymers made of both 'polymer of intrinsic microporosity (PIM-1)' and Ellagic acid were prepared for the first time by a facile one-step polycondensation reaction. By combining the highly porous and contorted structure of PIM (polymers with intrinsic microporosity) and flat-type hydrophilic ellagic acid, the membranes obtained from these random copolymers [(PIM-co-EA)-x] showed high CO2 permeability (> 4516 Barrer) with high CO2/N2 (> 23~26) and CO2/CH4 (> 18~19) selectivity, that surpassed the Robeson upper bound (2008) for both pairs of the gas mixture. Incorporation of flat-type ellagic acid into the PIM-1 not only enhances the gas permeability by disturbing the kinked structure of PIM-1 but also increases the selectivity of CO2 over N2 and CH4, due to an increase of rigidity and polarity in the resultant copolymer membranes.

Determination of Flavonoids, Tannins and Ellagic Acid in Leaves from Rubus L. Species

  • Gudej, Jan;Tomczyk, Michal
    • Archives of Pharmacal Research
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    • v.27 no.11
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    • pp.1114-1119
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    • 2004
  • This paper describes the quantitative determination of flavonoids, tannins and ellagic acid in the leaves from wild and cultivated variations of Rubus L. species (Rosaceae): raspberry (2 wild and 13 cultivars) and blackberry (3 wild and 3 cultivars). The content of flavonoids was analyzed using spectrophotometric (the Christ-M llers method) and HPLC analysis after acid hydrolysis. The content of tannins was determined by the weight method, with hide powder, described by German Pharmacopoeia 10 (DAB 10). Ellagic acid content was examined using the HPLC method after acid hydrolysis. Flavonoid content, determined using the Christ-Muller's method was higher for the blackberry leaves than for the raspberry leaves and varied between 0.46% and 1.05%. Quercetin and kaempferol were predominant in all samples analyzed using the HPLC method. The highest flavonoid content was found in the leaves of R. nessensis (1.06%); with results in all of the examined samples varying between 0.27% and 1.06%. The concentration of ellagic acid in all species was determined after acid hydrolysis and ranged from 2.06% to 6.89%. The leaves of raspberries are characterized by greater amounts of tannins (varying between 2.62% and 6.87%) than the leaves of other species. The results from this study indicate that the analyzed species are a rich source of flavonoids, ellagic acid and tannins, which may be used for the quality assessment of Rubus L. species leaves.

Unique Phenolic Sulphate Conjugates from the Flowers of Tamarix amplexicaulis

  • Souleman, Ahmed A.M.;Barakat, Heba H.;Hussein, Sahar A.M.;El-Mousallamy, Amani M.D.;Nawwar, Mahmoud A.M.
    • Natural Product Sciences
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    • v.4 no.4
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    • pp.245-252
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    • 1998
  • The unique sulphated phenolics, gallic acid 3-methyl ether 5-potassium sulphate, isoferulic acid 3-potassium sulphate, and ellagic acid 4,4'-dimethyl ether 3-potassium sulphate have been isolated from the flowers of Tamarix amplexicaulis Ehrenb. (Tamaricaceae). The hitherto unknown natural phenolic acid, gallic acid 3-methyl ether, together with the known phenolic, gallic acid, gallic acid 4-methyl ether, isoferulic acid, ferulic acid, ellagic acid, and ellagic acid 4,4'-dimethyl ether have been also separated and characterized. The structures were established by conventional methods, including electrophoretic analysis and confirmed by ESI-MS, $^1H-\;and\;^{13}C-NMR$.

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Effects of Gellan, Xanthan, and $\lambda$-Carrageenan on Ellagic Acid Sedimentation, Viscosity, and Turbidity of 'Campbell Early' Grape Juice

  • Ghafoor, Kashif;Jung, Ji-Eun;Choi, Yong-Hee
    • Food Science and Biotechnology
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    • v.17 no.1
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    • pp.80-84
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    • 2008
  • The effect of gellan (GE), xanthan (XA), and $\lambda$-carrageenan (LC) on the viscosity, sedimentation, ellagic acid content, and turbidity of grape 'Campbell Early' juice (CEJ) was investigated. CEJ samples with 0.15% each of GE, XA, and LC were tested for the above variables after 0, 5, 10, and 20 days of storage. The samples containing GE (0.15%) showed the least amount of sediment formation, the lowest ellagic acid content and turbidity, and a rise in viscosity. Sedimentation in CEJ decreased with increased viscosity due to the addition of gums which also limited the ellagic acid content and turbidity. GE was the most effective additive for the stabilization of CEJ.

Quantitative Analysis of the Three Marker Compounds in Sanguisorbae Radix by Processing Method (포제에 따른 지유의 지표성분 함량분석)

  • Seo, Chang-Seob;Kim, Jung-Hoon;Shin, Hyeun-Kyoo;Kim, Byoung-Soo
    • Korean Journal of Pharmacognosy
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    • v.46 no.4
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    • pp.342-351
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    • 2015
  • In this study, we performed quantitative determination of the three marker compounds such as gallic acid, ellagic acid, and quercetin in the 70% ethanol extracts of non-processed Sanguisorbae Radix and processed Sanguisorbae Radix using a high-performance liquid chromatography coupled with photodiode array detector. The analytical column for separation of the three compounds was used a Gemini $C_{18}$ column ($5{\mu}m$, $4.6{\times}250mm$) by the gradient elution with distilled water and acetonitrile containing 1.0% (v/v) acetic acid as mobile phase. The flow rate and injection volume were $1.0{\mu}L/min$ and $10{\mu}L$. The concentrations of gallic acid, ellagic acid, and quercetin in non-processed Sanguisorbae Radix were 0.25, 0.26, and 0.007%, respectively, while the concentrations of gallic acid, ellagic acid, and quercetin in non-processed Sanguisorbae Radix 0.14-0.55, 0.27-2.03, and 0.001-0.007%, respectively. Among the three components, the amount of the ellagic acid was increased after processing in Sanguisorbae Radix.