• 약학회지
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• 제45권2호
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• pp.214-219
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• 2001

Nineteen hydrolysable tannins isolated from the Euphorbia helioscopia (Euphorbiaceae) were tested for the inhibitory effect on mushroom tyrosinase activity in vitro. Inhibitory effect of gallotannin group exhibited more potent than that of phenolcarboxylic acid and ellagitannin groups against the enzyme activity. The inhibitory activity by pentagalloyl glucose on mushroom tyrosinase was more potent ($IC_{50}$/, 4.9 $\mu$M) than that of kojic acid ($IC_{50}$/, 8.7 $\mu$M).

• 생명과학회지
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• 제27권3호
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• pp.325-333
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• 2017

심혈관계 질환은 질환별 사망률 순위에 있어서 세계에서는 1위이며, 우리나라에서는 2위인 질병이다. 심혈관계 질환 발생의 주 위험 요인인 콜레스테롤은 HMG-CoA reductase에 의해 간에서 신생합성이 조절된다. 현재 고콜레스테롤혈증 치료에 statin이 널리 사용되고 있지만 광범위한 부작용이 보고되고 있어서 이를 대체하거나 보조할 수 있는 천연물 유래의 기능성 물질 개발이 필요한 실정이다. 따라서 본 연구에서는 혈장 콜레스테롤 감소 활성을 가지는 물질을 발굴하고자 71종의 페놀 및 그와 관련된 화합물들을 대상으로 10ug/ml 농도에서 HMG-CoA reductase 저해 활성을 탐색하였다. 그 결과, 1,4-naphthoquinone의 HMG-CoA reductase 저해율이 99.4%로 가장 높았고, 다음으로 plumbagin 91.4%, pentagalloyl ${\beta}-D-glucose$ 46.6%, 2,4-dihydroxybenzoic acid 40.9%, shikonin 37.7%, 1,2-naphthoquinone 36.6%, trans-cinnamic acid 32.0%, acetonylgeraniin 30.2%, benzoic acid 28.5%, geraniin 28.3%, gentisic acid 22.3%의 순이었다. $IC_{50}$값을 계산한 결과, 1,4-naphthoquinone가 $2.1{\mu}g/ml$로 가장 낮았으며, plumbagin과 pentagalloyl ${\beta}-D-glucose$은 각각 $5.8{\mu}g/ml$과 $13.1{\mu}g/ml$으로 나타났다. 1,4-naphthoquinone과 plumbagin의 경우, $5{\mu}g/ml$에서도 각각 90.3%와 43.3%의 저해율을 나타내었다.

• Natural Product Sciences
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• 제24권4호
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• pp.272-283
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• 2018

The root-knot nematode, Meloidogyne incognita caused a serious damage to many plants. The phenolic components of the leaves of Schinus terebinthifolius were investigated as potential nematicidal agents for M. incognita. Nine compounds were isolated and characterized as viz., 1,2,3,4,6-pentagalloyl glucose (1), kaempferol-3-O-${\alpha}$-L-rhamnoside (Afzelin) (2), quercetin-3-O-${\alpha}$-L-rhamnoside (Quercetrin) (3), myricetin (4), myricetin-3-O-${\alpha}$-L-rhamnoside (Myricetrin) (5), methylgallate (6), protocatechuic acid (7), quercetin (8), and gallic acid (9) using nuclear magnetic resonance (NMR) spectroscopy. Compound 1 showed pronounced nematicidal activity compared to Oxamyl as a positive control. It showed the lowest eggs-hatchability (34%) and the highest mortality in nematode population (21% after 72 hours of treatment) at a concentration of $200{\mu}g/mL$. It exhibited the best suppressed total nematode population, root galling and number of eggmasses in infected tomato plants. The total carbohydrates and proteins were also significantly induced by 1 with reduction in total phenolics and increase in defense-related proteins. Thus, compound 1 could be a promising, more safe and effective natural nematicidal agent for the control of root-knot nematodes.

• Natural Product Sciences
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• 제21권3호
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• pp.162-169
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• 2015

Hamamelis japonica (Hamamelidaceae), widely known as Japanese witch hazel, is a deciduous flowering shrub that produces compact clumps of yellow or orange-red flowers with long and thin petals. As a part of our ongoing search for phenolic constituents from this plant, eleven phenolic constituents including six flavonol glycosides, a chalcone glycoside, two coumaroyl flavonol glycosides and two galloylated compounds were isolated from the flowers. Their structures were elucidated as methyl gallate (1), myricitrin (2), hyperoside (3), isoquercitrin (4), quercitrin (5), spiraeoside (6), kaempferol 4'-O-β-glucopyranoside (7), chalcononaringenin 2'-O-β-glucopyranoside (8), trans-tiliroside (9), cis-tiliroside (10), and pentagalloyl-O-β-D-glucose (11), respectively. These structures of the compounds were identified on the basis of spectroscopic studies including the on-line LCNMR-MS and conventional NMR techniques. Particularly, directly coupled LC-NMR-MS afforded sufficient structural information rapidly to identify three flavonol glycosides (2 - 4) with the same molecular weight in an extract of Hamamelis japonica flowers without laborious fractionation and purification step. Cytotoxic effects of all the isolated phenolic compounds were evaluated on HCT116 human colon cancer cells, and pentagalloyl-O-β-D-glucose (11) was found to be significantly potent in inhibiting cancer cell growth.

• Applied Biological Chemistry
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• 제42권2호
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• pp.170-175
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• 1999

국내 식물자원으로부터 천연 항산화물질을 탐색하기 위하여 항산화활성이 기대되는 38종의 식물을 MeOH 수용액으로 추출한 후, EtOAc와 물로 분배, 추출하였다. 각 추출물에 대하여 DPPH radical 소거활성을 검정하였고, 이중에 작약을 포함한 13종의 식물에서 활성이 확인되었다. 작약뿌리로부터 항산화물질을 분리하기 위하여 80% MeOH 수용액으로 추출, 농축하였고, 이를 EtOAc, n-BuOH 및 물로 계통분획하였다. 활성이 확인된 n-BuOH과 EtOAc층에 대하여 활성을 추적해가며 column chromatography를 반복하여 3종의 활성물질을 분리하였다. 이들의 화학구조를 NMR 등의 spectral data를 해석하여 (+)-catechin, $1,2,3,4-tetragalloyl-6-digalloyl-{\beta}-D-glucose$ 및 $1,2,3,4,6-pentagalloyl-{\beta}-D-glucose$로 동정하였다.

• 생약학회지
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• 제36권1호통권140호
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• pp.9-16
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• 2005

Twenty eight compounds were isolated from the whole plant of Euphorbia jolkinii and evaluated for inhibitory effect on $5{\alpha}-reductase$ activity. Among the tested compounds, 1-desgalloyl eugeniin, hippomanin A, euphorbin D, exocoecarianin, rugosin E, and pentagalloyl glucose showed potent inhibitory effect on the enzyme activity. The inhibitory potency of rugosin E and euphorbin D, which are dimeric ellagitannins on $5{\alpha}-reductase$ activity, was 7-to 8-fold stronger than that of ${\gamma}-linolenic$ acid.

• Molecules and Cells
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• 제38권11호
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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.