• Archives of Pharmacal Research
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• 제19권3호
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• pp.231-234
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• 1996

Two acetophenone glycosides, 2, 4-dihydroxy-6-methoxy acetophenone $4-O-\beta-D-glucopyranoside(I)$, 2, 4, 6-trihydroxy acetophenone $2-O-\beta-D-glucopyranoside(II)$, together with coniferin(III) were isolated from the aerial parts of Artemisia stolonifera (Max.) Kom. The structures of the compounds were elucidated on the basis of spectroscopic evidence. Compound IIwas also confirmed as a new phenolic glycoside from natural sources. In addition, compound I induced cytostatic activity of macrophasges, while compounds II and III did not.

• 생명과학회지
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• 제24권8호
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• pp.873-879
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• 2014

소나무(Pinus densiflora)의 잎의 성분을 분리하여 항트롬빈 활성을 조사하였다. 잎은 70% ethanol로 3회 추출하였으며, 그 추출물은 순차적으로 chloroform과 n-buthanol로 분획하였다. n-buthanol 분획으로부터 얻은 수용성 분획을 MPLC와 HPLC에 의해 분리하였다. 분리한 compound를 $^1H-$과 $^{13}C-NMR$로 동정한 결과 2, 3-dihydro-7-hydroxyl-3-hydroxymethyl-2-(4'-hydroxyl-3-methoxyphenyl)-5-benzofuranpropanol-3-O-${\alpha}$-rhamnopyranoside(a neolignan glycoside)와 2, 3-dihyro-3-hydroxymethyl-7-methoxy-2-(4'-hydroxyphenyl-3'-methoxy)-5-benxofuran propanol 4'-O-${\alpha}$-rhamnopyranoside (icariside $E_4$)의 neolignan 구조임을 확인하였다. 트롬빈 저해활성은 분리된 neolignan glycoside와 icariside $E_4$을 작용하여 혈장안에서 응고시간으로 측정하였다. 그 결과, neolignan glycoside의 응고시간이 icariside $E_4$보다 4배 이상 지연하였다. 저해활성은 neolignan glycoside의 농도가 증가함에 따라 그 시간이 지연되는 것을 확인하였다. 더 나아가 지연기전을 확인하기 위해 thrombin과 순수한 fibrinogen를 반응하였다. 그 결과, 트롬빈과 순수한 피브리노겐의 작용에 의해 응고시간은 지연되었으며, 이는 neolignan glycoside가 피브린형성에 주요한 트롬빈의 활성을 직접 저해하는 것으로 사료된다.

• Archives of Pharmacal Research
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• 제28권11호
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• pp.1236-1238
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• 2005

A new phenolic glycoside, ophiopojaponin D (1), together with two known compounds, was isolated from the tubers of a famous traditional Chinese herb-Ophiopogon japonicus Ker-Gawl. The spectroscopic and chemical data revealed their structures to be 3-tetradecyloxy-4­hydroxy-allylbenzene-4-O-$\alpha$-L-rhamnopyranosyl (1$\rightarrow$6)-$\beta$-D-glucopyranoside (1), 3, 4-dihy-droxy-allylbenzene-4-O-$\alpha$-L-rhamnopyranosyl (1$\rightarrow$6)-$\beta$-D-glucopyranoside (2) and L-pyro­glutamic acid (3).

• Natural Product Sciences
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• 제16권4호
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• pp.233-238
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• 2010

In order to facilitate the quality control of Artemisia capillaris, a simple, accurate and reliable HPLC method was developed for the simultaneous determination of the six bioactive compounds: scopolin (1), chlorogenic acid (2), 2,4-dihydroxy-6-methoxyacetophenone 4-glycoside (3), hyperoside (4), isorhamnetin 3-Orobinobioside (5), and scoparone (6), which were selected as the chemical markers of A. capillaris. Separation was achieved on an Agilent Eclipse XDB-C18 column with a gradient solvent system of 0.1% trifluoroacetic acid aqueous-acetonitrile at a flow-rate of 1.0 mL/min and detected at 254 nm. All six calibration curves showed good linearity ($R^2$ > 0.998). A simple reversed phase HPLC method was developed for extracting pharmacologically active compounds scopolin, chlorogenic acid, 2,4-dihydroxy-6-methoxyacetophenone 4-glycoside, hyperoside, isorhamnetin 3-O-robinobioside, and scoparone from A. capillaris using a binary gradient of acetonitrile : 0.1% trifluoroacetic acid with UV detection at 254 nm. The scopolin (1), chlorogenic acid (2), 2,4-dihydroxy-6-methoxyacetophenone 4-glycoside (3), hyperoside (4), isorhamnetin 3-O-robinobioside (5), and scoparone (6) contents of the herb of A. capillaris collected from fifteen district markets in Korea were 0.00~0.90 mg/g, 0.06~7.29 mg/g, 0.06~0.91 mg/g, 0.07~5.05 mg/g, 0.42~13.11 mg/g, and 1.11~29.82 mg/g, respectively. The results demonstrated that this method is simple and reliable for the quality control of A. capillaris.

• Food Science and Biotechnology
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• 제14권1호
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• pp.58-63
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• 2005

Ethyl acetate-soluble neutral fraction of hot water extracts from the aerial parts of Angelica keiskei showed a 1, 1-diphenyl-2-picrylhydrazyl (DPPH) radical-scavenging activity. Six antioxidative compounds were purified and isolated by various chromatographic procedures. Based on the analyses of FAB-MS and NMR, the isolated compounds were structurally elucidated as luteolin 7-O-${\beta}$-D-glucopyranoside (1), quercetin 3-O-${\beta}$-D-galactopyranoside (2), quercetin 3-O-${\beta}$-D-glucopyranoside (3), quercetin 3-O-${\alpha}$-D-arabinopyranoside (4), kaempferol 3-O-${\alpha}$-D-arabinopyranoside (5), and luteolin 7-O-rutinoside (6). The glycosides of flavonols and luteolin showed DPPH radical-scavenging activity. One molecule of 2, 3, 4, 6, 1, and 5 scavenged 4.2, 4.2, 4.1, 2.5, 2.2, and 1.4 molecules of DPPH radical, respectively.

• Natural Product Sciences
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• 제15권4호
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• pp.192-197
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• 2009

Chemical investigation of the aerial parts of Artemisia iwayomogi has afforded five glycoside compounds. Their chemical structures were characterized by spectroscopic methods to be turpinionoside A (1), (Z)-3-hexenyl O-${\alpha}$-arabinopyranosyl-(1${\rightarrow}$6)-O-${\beta}$-D-glucopyranoside (2), (Z)-5'-hydroxyjasmone 5'-O-${\beta}$-Dglucopyranoside (3), (-)-syringaresinol-4-O-${\beta}$-D-glucopyranoside (4), and methyl 3,5-di-O-caffeoyl quinate (5). All of them were isolated for the first time from Artemisia species. The effect of compounds 1 - 5 on the function of osteoblastic MC3T3-E1 cells was examined by checking the cell viability, alkaline phosphatase (ALP) activity, collagen synthesis, and mineralization. Turpinionoside A (1) significantly increased the function of osteoblastic MC3T3-E1 cells. Cell viability, ALP activity, collagen synthesis, and mineralization were increased up to 117.2% (2 ${\mu}M$), 110.7% (0.4 ${\mu}M$), 156.0% (0.4 ${\mu}M$), and 143.0 % (2 ${\mu}M$), respectively.

• Horticulture, Environment, and Biotechnology : HEB
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• 제59권6호
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• pp.909-917
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• 2018

Quercetin and its glycoside derivatives were identified and quantified using high-performance liquid chromatograph (HPLC) and liquid chromatograph/mass spectrometer/mass spectrometer (LC/MS/MS) in the leaves, flowers, and fruits of 22 Malus genotypes. In all genotypes, small amounts of quercetin aglycone were present, with water-soluble glycoside forms were the most abundant in different Malus plant tissues, including quercetin-3-galactoside, quercetin-3-rutinoside, quercetin-3-glucoside, quercetin-3-xyloside, quercetin-3-arabinoside, and quercetin-3-rhamnoside. Among these six quercetin glycosides, quercetin-3-galactoside was the common form in Malus plants, except in the leaves and flowers of M. ceracifolia and M. magdeburgensis, and in the fruits of M. micromalus 'Haihong Fruit', where there was a higher concentration of quercetin3-glucoside. Among the different tissues tested, leaves contained the highest concentration of quercetin and its glycosides, while fruits contained the lowest concentrations of these compounds. Among the genotypes we analyzed, no specific genotype consistently contained the highest concentration of quercetin and its glycoside derivatives. M. domestica 'Honeycrisp' had the highest total compound concentration (approximately $1600mg\;kg^{-1}$), whereas M. hupehensis contained the lowest in its fruits. In contrast, the concentration of total quercetin and its glycosides was more than $5000mg\;kg^{-1}$ in the leaves of eight genotypes and greater than $2500mg\;kg^{-1}$ in the flowers of seven species. In general, the concentration of quercetin and its glycoside derivatives depended on the species and tissue type. These results may provide useful information for the evaluation and selection of edible Malus fruits and the materials for quercetin glycoside extraction.

• Biomolecules & Therapeutics
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• 제17권4호
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• pp.412-417
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• 2009

In the course of screening for antioxidant compounds by measuring the radical scavenging effect on DPPH (1,1-diphenyl- 2-picrylhydrazyl), a total extract of the twigs of Vitex rotundifolia (Verbenaceae) was found to show potent antioxidant activity. Subsequent activity-guided fractionation of the methanolic extract led to the isolation of three iridoid compounds, 10-O-vanilloylaucubin (1), 10-O-p-hydroxybenzoylaucubin (2) and aucubin (3), two C-glycoside flavones, vitexin (4) and orientin (5), and a quinic acid derivative, 3,4-di-O-caffeoylquinic acid (6). Their structures were elucidated by spectroscopic studies. Among them, compounds 5 and 6 showed the significant antioxidative effects on DPPH free radical scavenging test. In riboflavin-NBT-light and xanthine-NBT-xanthine oxidase systems, compounds 5 and 6 exhibited the formation of the blue formazan in a dose-dependent manner. Compounds 5 and 6 showed better superoxide quenching activities than vitamin C.

• 대한약학회:학술대회논문집
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• 대한약학회 2003년도 Proceedings of the Convention of the Pharmaceutical Society of Korea Vol.2-2
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• pp.200.4-201
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• 2003

Ten compounds were isolated from the methanolic extract of the whole plants of Diodia teres through repeated silica gel and Sephadex LH-20 column chromatography. Their chemical structures were elucidated as three iridoid glycosides, a coumarin glycoside, and six flavonoids by spectroscopic analysis. These compounds were isolated for the first time from D. teres.

• Journal of Microbiology and Biotechnology
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• 제33권12호
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• pp.1606-1614
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• 2023

Biochemical gut metabolism of dietary bioactive compounds is of great significance in elucidating health-related issues at the molecular level. In this study, a human gut bacterium cleaving C-C glycosidic bond was screened from puerarin conversion to daidzein, and a new, gram-positive C-glycoside-deglycosylating strain, Dorea sp. MRG-IFC3, was isolated from human fecal sample under anaerobic conditions. Though MRG-IFC3 biotransformed isoflavone C-glycoside, it could not metabolize other C-glycosides, such as vitexin, bergenin, and aloin. As evident from the production of the corresponding aglycons from various 7-O-glucosides, MRG-IFC3 strain also showed 7-O-glycoside cleavage activity; however, flavone 3-O-glucoside icariside II was not metabolized. In addition, for mechanism study, C-glycosyl bond cleavage of puerarin by MRG-IFC3 strain was performed in D₂O GAM medium. The complete deuterium enrichment on C-8 position of daidzein was confirmed by ¹H NMR spectroscopy, and the result clearly proved for the first time that daidzein is produced from puerarin. Two possible reaction intermediates, the quinoids and 8-dehydrodaidzein anion, were proposed for the production of daidzein-8d. These results will provide the basis for the mechanism study of stable C-glycosidic bond cleavage at the molecular level.