• Biomolecules & Therapeutics
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• v.21 no.6
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• pp.442-446
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• 2013

Here in this study, we isolated 1,2,3,4,6-penta-O-galloyl-${\beta}$-D-glucose (PGG) from Curcuma longa L. and elucidated the lifespan-extending effect of PGG using Caenorhabditis elegans model system. In the present study, PGG demonstrated potent lifespan extension of worms under normal culture condition. Then, we determined the protective effects of PGG on the stress conditions such as thermal and oxidative stress. In the case of heat stress, PGG-treated worms exhibited enhanced survival rate, compared to control worms. In addition, PGG-fed worms lived longer than control worms under oxidative stress induced by paraquat. To verify the possible mechanism of PGG-mediated increased lifespan and stress resistance of worms, we investigated whether PGG might alter superoxide dismutase (SOD) activities and intracellular ROS levels. Our results showed that PGG was able to elevate SOD activities of worms and reduce intracellular ROS accumulation in a dose-dependent manner.

• Journal of the Korean Wood Science and Technology
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• v.44 no.4
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• pp.559-570
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• 2016

The EtOAc and $H_2O$ soluble fractions of Katsura tree (Cercidiphyllum japonicum Sieb. Et Zucc) bark extracts were chromatographed on a Sephadex LH-20 column with various aqueous MeOH. Gallic acid (1), methyl galate (2), kurigalin (3), 1,2,3,6-tetra-O-galloyl-${\beta}$-D-glucose (4) and 1,2,3,4,6-penta-O-galloyl-${\beta}$-D-glucose (5) were isolated from EtOAc fraction. Isocorilagin (6) and methyl galate (2) were separated from $H_2O$ fraction. The structure determination was done by $^1H$ and $^{13}C$ NMR. Of these isolated compounds, methyl galate (2), kurigalin (3) and isocorilagin (6) were isolated, for the first time, from the bark extracts of Cercidiphyllum japonicum.

• Preventive Nutrition and Food Science
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• v.2 no.4
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• pp.285-290
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• 1997

Previously, a 50% aqueous methanol extract of Galla rhois was shown to be the most potent tyrosinase inhibition activity with an {TEX}$IC_{50}${/TEX}(the concentration causing 50% inhibition of tyrosinase activity) of 0.2mg/ml of 205 crude drug extracts. To isolate tyrosinase inhibitors, the methanol extract was evaporated to a small volume in vacuo, and then partitioned stepwise with benzene and ethyl acetate(EtOAc). the EtOAc fraction was solubilized in 10% MeOH solution, and then fractionated successively by Diaion HP-20 and Sephadex LH-20 column chromatography, and preparative HPLC. Three phenolic compounds were isolated, and characterized as gallic acid(GA), methyl gallate(MG) and 1,2,3,4,6-penta-O-galloyl-$\beta$-D-glucose(PGG) by UV, IR, {TEX}${1}^H${/TEX}-&{TEX}${13}^C${/TEX}-NMR, and FAB-MS spectroscopy, PGG({TEX}$IC_{50}${/TEX}=50$\mu\textrm{g}$/ml) showed a considerable inhibitory effect against mushroom tyrosinase, while GA({TEX}$IC_{50}${/TEX}=1.6mg/ml) and MG({TEX}$IC_{50}${/TEX}=234$\mu\textrm{g}$/ml) did not show an appreciable effect. Meanwhile, MG inhibited greatly melanogenesis in a murine melanocyte cell line, Mel-Ab. MG and PGG showed typical noncompetitive inhibition patterns against mushroom tyrosinase. These results suggest that PGG and MG may be potentially useful as either anti-browning or anti-melanogenic agents in foods and cosmetics.

• Journal of the Korean Society of Food Science and Nutrition
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• v.46 no.4
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• pp.409-416
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• 2017

1,2,3,4,6-Penta-O-galloyl-${\beta}$-D-glucose (PGG) is a gallotannin isolated from Galla Rhois. In a previous study, PGG was shown to suppress the allergic response by attenuating immunoglobulin E production both in vitro and in vivo. However, the effect of PGG on bacteria-induced inflammation at physiological concentration remains unclear. Therefore, the aim of this study was to investigate the effect of PGG on lipopolysaccharide (LPS)-stimulated macrophages. PGG inhibited release of nitric oxide (NO) and prostaglandin $E_2$ by alleviating protein expression of inducible NO synthase and cyclooxygenase-2 in LPS-treated RAW264.7 cells. Furthermore, PGG suppressed the release of interleukin-6 and tumor necrosis factor-${\alpha}$ induced by LPS. Further study indicated that PGG blocked translocation of the p65 subunit of nuclear factor-${\kappa}B$ from the cytosol into the nucleus, which is one of the underlying mechanisms of the anti-inflammatory action of PGG. Collectively, these data suggest that PGG might be useful for the treatment of inflammatory disease.

• Molecules and Cells
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• v.38 no.11
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• pp.982-990
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• 2015

Exposure of the skin to ultraviolet radiation can cause skin damage with various pathological changes including inflammation. In the present study, we identified the skin-protective activity of 1,2,3,4,6-penta-O-galloyl-${\beta}$-D-glucose (pentagalloyl glucose, PGG) in ultraviolet B (UVB) radiation-induced human dermal fibroblasts and mouse skin. PGG exhibited antioxidant activity with regard to intracellular reactive oxygen species (ROS) generation as well as ROS and reactive nitrogen species (RNS) scavenging. Furthermore, PGG exhibited anti-inflammatory activity, inhibiting the activation of nuclear factor-kappaB (NF-${\kappa}B$) and mitogen-activated protein kinase (MAPK) signaling, resulting in inhibition of the expression of pro-inflammatory mediators. Topical application of PGG followed by chronic exposure to UVB radiation in the dorsal skin of hairless mice resulted in a significant decrease in the progression of inflammatory skin damages, leading to inhibited activation of NF-${\kappa}B$ signaling and expression of pro-inflammatory mediators. The present study demonstrated that PGG protected from skin damage induced by UVB radiation, and thus, may be a potential candidate for the prevention of environmental stimuli-induced inflammatory skin damage.

• Korean Journal of Pharmacognosy
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• v.39 no.1
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• pp.28-36
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• 2008

From the 70% EtOH extract of Paeonia lactiflora roots (Paeoniaceae), fourteen phenolic and related compounds were isolated. They were identified as ${\alpha}-tocopherol$ (1), dioctylphthalate (2), ${\alpha}-tocospiro$ B (3), paeonol (4), 3,3'-di-O-methylellagic acid(5), 3,4'-di-O-methylellagic acid (6), benzoic acid (7), aromadendrin (8), p-hydroxybenzoic acid (9), (+)-catechin (10), gallic acid (11), nicotinamide (12), methyl gallate (13) and $1,2,3,4,6-penta-O-galloyl-{\beta}-D-glucose$ (14) by spectroscopic methods. Among these compounds, 1-3, 5, 6, 8 and 12 were isolated for the first time from this plant.

• Korean Journal of Pharmacognosy
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• v.23 no.4
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• pp.211-217
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• 1992

Seven hydrolysable tannins and two related compounds have been isolated from the acetone-water(4 : 1) soluble portion of the aerial parts of Euphorbia ebracteolata(Euphorbiaceae). Seven hydrolysable tannins have been determined as 3-O-galloyl-shikimic acid, 1, 3, 4, 6-tetra-O- and $1,\;2,\;3,\;4,\;6-penta-O-galloyl-{\beta}-D-glucose$, corilagin, tercatain, punicafolin and geraniin and two related compounds determinedasgallicacidandellagicacidonthebasisof spectral data and physico-chemical evidence.

• Korean Journal of Pharmacognosy
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• v.40 no.3
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• pp.229-232
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• 2009

The ethanol (EtOH) extract of the branches of Cotinus coggygria (Anacardiaceae) exhibited a significant inhibition on the yeast $\alpha$-glucosidase, one of the key enzymes related with diabetes mellitus, in a dose dependent manner, in vitro. The intensive phytochemical survey of the EtOH extract of the species by way of bioactivity-guided fractionation resulted in the isolation of 1,2,3,4,6-penta-O-galloyl-$\beta$-D-glucose (1) as an active principle responsible for the inhibition on $\alpha$-glucosidase, together with two related components 2 and 3. Compound 1 demonstrated a strong inhibition on the yeast $\alpha$-glucosidase, in vitro and $IC_{50}$ value was calculated as 0.96 mg/ml, when that of a reference drug, acarbose was estimated as 5.3 mg/ml. On the other hand, other related constituents of the species, 1,2,3,6-tetra-O-galloyl-$\beta$-D-glucose (2) and gallic acid (3) were exhibited relatively poor inhibition upon the yeast $\alpha$-glucosidase, respectively.

• Journal of Life Science
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• v.26 no.11
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• pp.1320-1329
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• 2016

The present study examined the cytotoxic effects of 1, 2, 3, 4, 6-penta-O-galloyl-${\beta}$-D-glucose (PGG), known as the pentahydroxy gallic acid ester of glucose, in the various human cancer cell lines (A-549, MDA-MB-231, U87-MG, MCF-7 and PANC-1), normal MRC-5 fetal fibroblasts, and dental papilla tissue- derived mesenchymal stem cells (DPSCs). Significantly (p<0.05) lower half maximal inhibitory concentration ($IC_{50}$) values were observed in the A-549 and MDA-MB-231 cells showing a high proliferation capacity, compared with other cancer and normal cell lines with a relatively low proliferation capacity. The population doubling time (PDT) was significantly (p<0.05) higher in the $10{\mu}M$ PGG-treated cell lines than those of untreated control cell lines. The present study demonstrated that the $IC_{50}$ value increases proportionally to the extending PDT. A high cell number with senescence-associated ${\beta}-galactosidase$ activity was also observed in the $10{\mu}M$ PGG-treated cells compared with those of untreated control cells. Moreover, the level of telomerase activity was significantly (p<0.05) decreased with $10{\mu}M$ PGG treatment, especially in A-549 and MDA-MB-231 cells showing a high proliferation capacity. Based on these observations, PGG could serve as a potent agent for cancer chemotherapy, as its treatment was more effective in cells with a high proliferation capacity.

• Natural Product Sciences
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• v.10 no.5
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• pp.223-227
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• 2004

This study was carried out to investigate inhibitory effect of extracts from the root of Paeonia lactiflora on postprandial hyperglycemia. Organic solvent (hexane, ethyl acetate, butanol, aqueous) extracts from the crude drug were fractionated by high performance liquid chromatography. These fractions were examined to evaluate ${\alpha}-glucosidase$ (EC 3. 2. 1. 20) inhibition by microplate colorimetric assay. Among the fractions examined, the ethyl acetate fraction from the roots of Paeonia lactiflora showed potent inhibitory effects on ${\alpha}-glucosidase$. Therefore, further fractionation of the fraction was carried out to isolate the active principles. Finally, we isolated and Purified 1,2,3,4,6-penta-O-galloyl-beta-D-glucose (PGG) as a active principle by activity-guided fractionation. These results suggest that the extract from the root of Paeonia lactiflora can be used as a new nutraceutial for inhibition on postprandial hyperglycemia and PGG might be a candidate for developing an ${\alpha}-glucosidase$ inhibitor.