• 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.

• Natural Product Sciences
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• 제3권1호
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• pp.8-10
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• 1997

A new flavonol glycoside, quercetin 3-rhamnosyl $(1{\rightarrow}3)$ galactoside [5] was isolated from the leaves of M. africana. The known compounds kaempferol 3-rutinoside [1], 3'-O-methylquercetin 3-rutinoside [2], quercetin 3-rutinoside [3], and quercetin 3-rhamnosyl $(1{\rightarrow}6)$ galactoside [4] were also isolated for the first time from this plant. Their structures were determined by chemical and spectroscopic methods.

• 생약학회지
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• 제37권1호통권144호
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• pp.42-47
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• 2006

The contents of quercetin glyciside in Saururus chinensis Baill was higher in the 2nd year, 1st year and 3rd year in leaves, and in the 1st year, 3rd year and 2nd year in stems in that orders. Content of lignans in the rhizome was not significantly different cultivated years. The total phenolics, quercetin glycoside and EDA of plant parts were higher in order of flower, leaf and chopping sample. The total phenolics and EDA of stem were much lower than parts and quercetin glycoside was not detected.

• 한국약용작물학회지
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• 제14권3호
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• pp.143-147
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• 2006

삼백초(三白草) 재배에 있어서 토성에 따른 생육과 유효성분을 분석하여 안정적인 재배법을 확립하고 고품질 삼백초를 생산하고자 시험을 수행한 결과를 요약하면 다음과 같다. 가. 삼백초의 절수와 엽수, 분지수는 토성 간 차이가 없었으며, 주당 줄기와 잎의 무게는 사양토가 가장 많고, 양토, 식양토, 사토의 순으로 무거웠다. 직경 5mm이하 뿌리는 토성 간차이가 없었으나, $5.1{\sim}10.9\;mm$의 굵기는 사양토, 양토 그리고 식양토에서 $437{\sim}465\;g$로 차이가 없었고, 11 mm이상은 식양토가 많았다. 건물율은 $19.1{\sim}20.8%$로 차이가 없었다. 나. 잎의 quercetin-glycoside 함량은 양토와 사양토에서 $219.3{\sim}222.4\;mg/100\;g$로 가장 높았으며, quercitrin>rutin>isoquercitrin>hyperin의 순으로 높았다. 줄기는 사토와 사양토가 각각 14.8 mg/100 g과 12.4 mg/100 g로 가장 많았으며, quercetin-glycoside 중 rutin이 가장 높았다. 다. 뿌리의 lignans 함량은 식양토, 양토, 사앙토, 사토의 순으로 높은 경향이었으며, lignans 관련 물질 중 manassatin B가 가장 많았다.

• 생약학회지
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• 제24권1호
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• pp.47-53
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• 1993

The seasonal variations of the major six flavonol glycosides(kaempferol 2,6-dirhamnosyl glucoside, quercetin 3-O-rutinoside, kaempferol 3-O-rutinoside, isorhamnetin 3-O-rutinoside, quercetin 3-O-coumaroyl glucorhamnoside and kaempferol 3-O-coumaroyl glucorhamnoside) in Ginkgo biloba leaves were investigated. The contents were determined by HPLC on reversed phase $C_{18}$ column. This result showed that the percentage of six flavonol glycosides decreased during the season from 1.57% in May to 0.39% in November. The content of each flavonol glycoside indicated a similar tendency to decrease. However, the contents of rutinosides of kaempferol, quercetin and isorhamnetin fluctuated markedly than those of coumaroyl glucorhamnosides of kaempferol and quercetin and kaempferol 2,6-dirhamnosyl glucoside.

• 한국약용작물학회지
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• 제13권6호
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• pp.250-254
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• 2005

Night-break, 일장조절, 월동가온 실험으로부터 얻어진 바위솔에 포함된 flavonol glycoside, $kaempferol-3-O-{\beta}-D-glucoside$(1), $kaempferol-3-O-{\beta}-D-glactoside$ (2), $kaempferol-3-O-{\beta}-D-rhamnoside$ (3), $quercetin-3-O-{\beta}-D-glucoside$ (4) and $quercetin-3-O-{\alpha}-D-rhamnoside$ (5)의 함량이 분석되었으며 자연산 바위솔의 함량과 비교되었다. 월동가온 시험에서 얻은 flavonol glycoside 1-5의 함량은 자연산보다 감소하였으며 일장조절 실험 및 night-break 시험에서 얻은 flavonol glycoside 함량은 조사한 빛의 양이 증가함에 따라 증가하였다. 월동가온은 flavonol glycoside의 생성에 부정적으로 작용하는 반면 조사되는 빛의 양의 증가와 같은 경작조건은 flayonol glycoside의 생성에 유리하다.

• Animal cells and systems
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• 제7권4호
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• pp.327-330
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• 2003

We analyzed and compared profiles of flavonols extracted from leaves and exocarps of the grape Kyoho by TLC, HPLC and UV spectrophotometry. In the exocarps, quercetin 3-O-glucoside was the main compound while isorhamnetin 3-O-glycoside (I) was present in minor amounts. In leaves, on the other hand, quercetin 3-O-glucoside and quercetin 3-O-glucoside-7-O-glucronide were the major compounds while isorhamnetin 3-O-glycoside (II) and kaempferol 3, 7-O-diglycoside were present in minor amounts.

• 약학회지
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• 제43권1호
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• pp.5-10
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• 1999

As one of the serial studies on the specific and indigenous plants of Mt. Chiri the constituents of aerial part from filipendula formosa (Rosaceae) were investigated. From of the MeOH extract, five flavonol glycosides, kaempferol-3-O-$\beta$-D-galactopyranoside, querecetin-3-O-$\beta$-D-galactopyranoside, quercetin-3-O-$\alpha$-Lrhamopyranosyl (1 6)-$\beta$-D-galactopyranoside, kaempferol-3-O-$\alpha$-L-rhamnopyranosyl (1 6)-$\beta$-D-galactopyranoside and quercetin-7-O-$\beta$-D-glucopyranosy-3-O-$\beta$-D-galactopyranoside were isolated by column chromatographic separation using Amberlite XAD-2 and Sephadex LH-20, and identified physicochemical evidences (IR, FAB-Mass, $^1H,{\;}^{13}C-NMR$).

• Natural Product Sciences
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• 제13권3호
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• pp.225-228
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• 2007

A new quercetin 3-O-trisaccharide was isolated from the leaves of Rubus crataegifolius (Rosaceae). The structure of this compound was determined as quercetin $3-O-{\alpha}-L-arabinofuranosyl-(1{\rightarrow}2)-{\beta}-D-xylopyranosyl-(1{\rightarrow}2)-{\beta}-D-galactopyranoside$ on the basis of 2D-NMR spectroscopic data. This flavonol glycoside was isolated for the first time from a natural source.

• Journal of Microbiology and Biotechnology
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• 제28권11호
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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.