• Journal of the Korean Society of Food Science and Nutrition
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• v.25 no.1
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• pp.76-79
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• 1996

생강나무 (Libdera obtusiloba BL.)의 페놀성 화합물들을 분리하기 위하여 잎고 줄기의 MeOH 엑스로부터 계통 분획한 EtOAc 분획물은 silica gel column chro-matography로 분리하여 2종의 화합물을 얻었다. IR, UV,$^1H-NMR$, $^13C-NMR$ 등의 분석을 행하여 화학구조를 밝힌 결과 이들 화합물의 화학구조는 잎에서 $quer-cetin-3-O-\alpha-L-rhamnopyranoside(quercitrin),$ 줄기에서는 quercetin $3-O-\beta-D-galactoyranoside(hyperoside)로$ 각각 결정하였다. 이 화합물들은 생강나무에서 처음으로 분리하였다.

• Journal of the Society of Cosmetic Scientists of Korea
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• v.16 no.1
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• pp.1-17
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• 1990

The major flavonoid component of Ginseng leaf is trifolin, a glycoside of kaempferol. To evaluate the antioxidative properties of trifolin and kaempferol on cellular membranes, we compared them with the other flavonoids through the 102-Induced photohemolysis of rabbit erythrocytes. All the flavonoid aglycones including kaempferol, quercetin and baicalein protected effectively the cells from the 102-caused damage in a dose- dependent manner, by scavenging 102 and free radicals in the cellular membranes. The solubilization of the flavonoid aglycones into micelles or erythrocyte membranes was deduced from spectro-photometric and microscopic observations. The flavonoid glycosides were not protective or less protective than their corresponding aglycones, and trifolin was the only glycoside that exhibited a solubilization into the membranes and a significant protection against the photohemolysis. We also tested some phenolic compounds contained in Ginseng, and found that they did not prevent the photohemolysis so effectively as kaempferol or trifolin.

• Journal of Life Science
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• v.29 no.12
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• pp.1371-1377
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• 2019

Oxidative stress induced by the over-production of reactive oxygen species (ROS) in the brain is the most common cause of neurodegenerative diseases such as Alzheimer's. In the present study, we investigated the protective effects of flavonoids and their glycosides, namely kaempferol, kaempferol-3-O-glucoside, quercetin, and quercetin-3-β-D-glucoside, against H₂O₂-induced oxidative stress in the C6 glial cells. The H₂O₂-treated glial cells exhibited decreased cell viability and increased ROS production when compared with normal cells. However, cells treated with each of the four flavonoids/glycosides demonstrated significantly increased viability and suppressed ROS production when compared with the H₂O₂-treated control group. These results indicate that flavonoids/glycosides attenuate oxidative stress induced by H₂O₂ in C6 glial cells. To confirm the protective molecular mechanisms, we measured pro-inflammatory factors such as inducible nitric oxide synthase, cyclooxygenase-2, and interleukin-1β. H₂O₂ treatment was seen to elevate these factors and decrease IκB-α in the C6 glial cells, while the flavonoids/glycosides induced a down-regulation of the pro-inflammatory factors and increased IκB-α, indicating a neuroprotective effects through attenuation of the inflammation. In particular, quercetin and its glycoside showed a higher neuroprotective effect than the kaempferol treatments. These results suggest that these flavonoids and their glycosides could be promising therapeutic agents for neurodegenerative diseases via the attenuation of oxidative stress.

• Proceedings of the Ginseng society Conference
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• 1990.06a
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• pp.49-57
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• 1990

It has been well known that extended exposure to reactive oxygens causes severe damage to susceptible biomolecules. In this study, the effects of flavonoids including trifling and kaempferol from Ginseng leaves on single oxygen induced photohemolysis of erythrocytes and free radical scavenging activities were investigated . Each flavonoid aglycone (5-50UM) such as kaempferol, quercetin or baicalein exhibited a high protective effect against the photohemolysis. They protected the cells by scavenging 102 and free radicals. Although the free radical scavenging activities of the flavonoid glycosides were not much lower than those of their corresponding aglycones, their insolubility into lipid bilayers of membrane made them less effective in preventing the photohemolysis induced by 1O2. The 102 and free radical scavenging activities of flavonoids were estimated by the decomposition of the flavonoid by 1O2 and the bleaching of free radicals by the flavonoid, respectively. The solubilization of the flavonoid into micelle or erythrocytes was deduced from spectrophotometric and microscopic observations. The cooperation of L-ascorbic acid and a flavonoid, and a possible involvement of lipoxygenase or cyclooxygenase in the photohemolysis mechanism were discussed. Keywords Panax ginseng C.A Meyer, ginseng leaves, flavonoids, singe1 oxygen, Photohemolysis.

• Journal of Ginseng Research
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• v.14 no.2
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• pp.191-199
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• 1990

It has been well known that extended exposure to reactive oxygens causes severe damage to susceptible biomolecules. In this study, the effects of flavonoids including trifolin and kaempferol from Ginseng leaves on singlet oxygen induced photohemolysis of erythrocytes and free radical scavenging activities were investigated. Each flavonoid aglycone (5-50$\mu$M) such as kaempferol, quercetin or baicalein exhibited a high protective effect against the photohemolysis. They protected the cells by scavenging $^1O_2$ and free radicals Although the free radical scavenging activities of the flavonoid glycosides were not much lower than those of their corresponding aglycones, their insolubility into lipid bilayers of membrane made them less effective in preventing the photohemolysis induced by $^1O_2$. The $^1O_2$ and free radical scavenging activities of flavonoids were estimated by the decomposition of the flavonoid by $^1O_2$ and the bleaching of free radicals by the flavonoid, respectively. The solubilization of the flavonoid into micells or erythrocytes was deduced from spectrophotometric and microscopic observations. The cooperation of L-ascorbic acid and a flavonoid, and a possible involvement of lipoxygenase or cyclooxygenase in the photohemolysis mechanism were discussed.

• Biomolecules & Therapeutics
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• v.15 no.1
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• pp.46-51
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• 2007

Bioassay-directed chromatographic fractionation of an ethyl acetate extract from leaves of sweet potato (Ipomoea batatas L.) afforded six quinic acid derivatives: 3,5-epi-dicaffeoylquinic acid (1), 3,5-dicaffeoylquinic acid (2), methyl 3,5-O-dicaffeoylquinate (3), methyl 3,4-dicaffeoylquinate (4), methyl 4,5-dicaffeoylquinic acid (5),4,5-dicaffeoylquinate (6), and two phenolic compounds: caffeic acid (7) and caffeic acid methyl ester (8) together with three flavonoids: quercetin 3-O-${\beta}$-D-glucopyranoside (9), quercetin 3-O-${\beta}$-D-glucopyranoside, isoquercitrin (10) and kaempferol 3-O-${\beta}$-D-glucopyranoside (11). The structures of these compounds were elucidated by the aid of spectroscopic methods. These compounds were assessed for antioxidant activities using three different cell-free bioassay systems. All isolates except 11 showed potent DPPH and superoxide anion radicals scavenging, and lipid peroxidation inhibitory activities. 3,5-epi-DCQA (1) and methyl quinates (3-5) along with flavonoide 9 were isolated for the first time from this plant.

• Korean Journal of Pharmacognosy
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• v.42 no.2
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• pp.138-143
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• 2011

A high performance liquid chromatography (HPLC) method was developed for simultaneous determination of two major flavonoid glycosides (poncirin and nanringin) in Poncirus trifoliata Raf. by different harvesting times and locations for two years. A SunFire $C_{18}$ column (4.6 mm${\times}$250 mm, 5 ${\mu}M$) was used at $40^{\circ}C$ for the determination of poncirin and naringin. The mobile phase using gradient flow consisted of two solvent systems. Solvent A was 1.0% (v/v) aqueous acetic acid and solvent B was acetonitrile with 1.0% (v/v) acetic acid. Flow rate was 1.0 mL/min and injection volume was 10 ${\mu}l$. The chromatogram was monitored by photodiode array (PDA) detection at 280 nm for the identification of two flavonoid glycosides in P. trifoliata. The contents of the two components in P. trifoliata ranged from 0.32~13.02%.

• YAKHAK HOEJI
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• v.33 no.2
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• pp.124-128
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• 1989

The drug consists of the dried entire plant of Viola diamantica (family Violaceae). It is used for the treatment of acute pyogenic diseases such as boil and carbuncles; also as tumor, high fever, tuberculosis and astringent hemostatic. Two flavonol glycosides have been isolated from the aerial parts of Viola diamantica and could be identifed as kaempferol 7-rhamnoside and kaempferol 3,7-dirhamnoside (bright yellow needle crystal, mp $225^{\circ}$, $C_{27}\;H_{30}\;O_4\;4H_2O$). Kaempferol 7-rhamnoside and kaempferol 3,7-dirhamnoside were first isolated from Viola diamantica.

• Journal of Microbiology and Biotechnology
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• v.28 no.11
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• pp.1859-1864
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• 2018

Synthesis of flavonoid glycoside is difficult due to diverse hydroxy groups in flavonoids and sugars. As such, enzymatic synthesis or biotransformation is an approach to solve this problem. In this report, we used stepwise biotransformation to synthesize two quercetin bisglycosides (quercetin 3-O-glucuronic acid 7-O-rhamnoside [Q-GR] and quercetin 3-O-arabinose 7-O-rhamnoside [Q-AR]) because quercetin O-rhamnosides contain antiviral activity. Two sequential enzymatic reactions were required to synthesize these flavonoid glycosides. We first synthesized quercetin 3-O-glucuronic acid [Q-G], and quercetin 3-O-arabinose [Q-A] from quercetin using E. coli harboring specific uridine diphopsphate glycosyltransferase (UGT) and genes for UDP-glucuronic acid and UDP-arabinose, respectively. With each quercetin 3-O-glycoside, rhamnosylation using E. coli harboring UGT and the gene for UDP-rhamnose was conducted. This approach resulted in the production of 44.8 mg/l Q-GR and 45.1 mg/l Q-AR. This stepwise synthesis could be applicable to synthesize various natural product derivatives in case that the final yield of product was low due to the multistep reaction in one cell or when sequential synthesis is necessary in order to reduce the synthesis of byproducts.

• Biomolecules & Therapeutics
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• v.24 no.4
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• pp.410-417
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• 2016

Quercetin is a flavonoid usually found in fruits and vegetables. Aside from its antioxidative effects, quercetin, like other flavonoids, has a various neuropharmacological actions. Quercetin-3-O-rhamnoside (Rham1), quercetin-3-O-rutinoside (Rutin), and quercetin-3-(2(G)-rhamnosylrutinoside (Rham2) are mono-, di-, and tri-glycosylated forms of quercetin, respectively. In a previous study, we showed that quercetin can enhance ${\alpha}7$ nicotinic acetylcholine receptor (${\alpha}7$ nAChR)-mediated ion currents. However, the role of the carbohydrates attached to quercetin in the regulation of ${\alpha}7$ nAChR channel activity has not been determined. In the present study, we investigated the effects of quercetin glycosides on the acetylcholine induced peak inward current ($I_{ACh}$) in Xenopus oocytes expressing the ${\alpha}7$ nAChR. $I_{ACh}$ was measured with a two-electrode voltage clamp technique. In oocytes injected with ${\alpha}7$ nAChR copy RNA, quercetin enhanced $I_{ACh}$, whereas quercetin glycosides inhibited $I_{ACh}$. Quercetin glycosides mediated an inhibition of $I_{ACh}$, which increased when they were pre-applied and the inhibitory effects were concentration dependent. The order of $I_{ACh}$ inhibition by quercetin glycosides was Rutin${\geq}$Rham1>Rham2. Quercetin glycosides-mediated $I_{ACh}$ enhancement was not affected by ACh concentration and appeared voltage-independent. Furthermore, quercetin-mediated $I_{ACh}$ inhibition can be attenuated when quercetin is co-applied with Rham1 and Rutin, indicating that quercetin glycosides could interfere with quercetin-mediated ${\alpha}7$ nAChR regulation and that the number of carbohydrates in the quercetin glycoside plays a key role in the interruption of quercetin action. These results show that quercetin and quercetin glycosides regulate the ${\alpha}7$ nAChR in a differential manner.