• 대한한의학방제학회지
• /
• 제12권1호
• /
• pp.255-262
• /
• 2004

The inhibitory effect of the aerial parts of Fagopyrum esculentum on the 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical was examined. The n-butanol fraction from the methanol extract of title plant showed stronger inhibitory effect than other fractions on DPPH radical. Two flavonoids were isolated from n-butanol fraction having the potent activity and elucidated as quercetin-3-O-${\alpha}$-L-rhamnoside and quercetin-3-O-rutinoside on the basis of spectral evidence. The $IC_{50}$ values of these compounds on DPPH radical were 6.56 ${\mu}M$ and 8.37 ${\mu}M$, respectively.

• 한국자원식물학회지
• /
• 제30권6호
• /
• pp.618-622
• /
• 2017

Various bioactive substances are found in Loranthus tanakae, including quercetin 3-rhamnoside (1), kaempferol 3-rhamnoside (2), rhamnetin 3-rhamnoside (3), and rhamnocitrin 3-rhamnoside (4), which inhibit tyrosinase. These compounds are mainly found in the EtOAc fraction of L. tanakae extract and demonstrate higher rates of tyrosinase inhibition than ascorbic acid, which was used as a control. Our results suggest that L. tanakae extracts can be utilized in skin whitening cosmetics.

• Journal of Microbiology and Biotechnology
• /
• 제28권11호
• /
• pp.1859-1864
• /
• 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.

• 한국식품위생안전성학회지
• /
• 제11권2호
• /
• pp.115-121
• /
• 1996

In order to compare the suppressive effect of quercetin and several its glycosides, such as quercitrin (quercetin-3-rhamnoside), isoquercitrin (quercetin-3-glucoside), hyperin (quercetin-3-galactoside) and tutin (quercetin-3-rhamnosyl glucoside), on the genotoxicity by N-methyl-N-nitrosourea(MNU), in vitro sister chromatid exchange(SCE) test using mouse spleen lymphocytes and in vivo micronucleus test using mouse peripheral blood were performed. MNU-induced SCEs in vitro were not decreased by the simultaneous treatment of test compounds. Among them, quercetin and hyperin showed significant suppressive effects at high dose(10-5M). On the other hand, MNU-induced micronucleated reticulocytes(MNRETS) in vivo were significantly decreased with good dose-dependent manner in all compound tested. However, there were not significant differences between quercetin aglycone and its glycosides in the suppressive aglycone and its glycosides may act as an antigenotoxic agent in vivo and may be useful as a chemopreventive agent of alkylating agent.

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

• 생약학회지
• /
• 제29권3호
• /
• pp.163-168
• /
• 1998

Seven antioxidative compounds were isolated from chloroform and ethyl acetate extracts of the stem bark of Eucalyptus globulus (Myrtaceae). They were identified as rhamnazin (1), rhamnetin (2), naringenin (3), eriodictyol (4), quercetin (5), taxifolin (6) and dihydrokaempferol-3-rhamnoside (7) on the basis of various spectroscopic analyses. These compounds inhibited lipid peroxidation with $IC_{50}$ values of 0.08-30 ${\mu}g/ml$.

• Journal of Applied Biological Chemistry
• /
• 제54권1호
• /
• pp.47-50
• /
• 2011

본 연구에서는 천연 미백소재 탐색을 위하여 쪽(P. tinctoria) 꽃 추출물의 tyrosinase 저해활성을 검증하였으며, 쪽 꽃 추출물은 $70.8{\pm}2.2{\mu}g/mL$의 $IC_{50}$ 값을 나타내었다. LH-20 chromatography와 HPLC분석을 통해 쪽으로부터 두 개의 활성물질을 정제하였고, 이 물질들의 구조 분석은 LC-MS와 NMR 데이터 해석을 바탕으로 진행하여 두 가지 화합물은 각각 quercetin-3-Orhamnoside (Q3R), myricetin-3-O-rhamnoside (M3R)로 밝혀졌다. Q3R과 M3R은 순서대로 $47.0{\pm}0.1$, $150.5{\pm}1.6{\mu}g/mL$의 $IC_{50}$ 값을 나타내었다. 이로 미루어 보아, 쪽 꽃 추출물과 두 활성물질의 멜라닌 생합성 저해활성을 확인할 수 있었으며, 쪽 꽃추출물의 미백소재로서의 적용 가능성을 확인할 수 있었다.

• Bulletin of the Korean Chemical Society
• /
• 제32권3호
• /
• pp.981-987
• /
• 2011

The anomalous spectroscopic properties of quercetin-3-O-rhamnoside (QCRM) and quercetin-3-O-rutinoside (QCRT) in AOT reverse micelle were studied. The excited state intramolecular proton transfer (ESIPT) occurs through the strong hydrogen bond between the -OH at position 5 and the carbonyl oxygen. Because the ESIPT can only happens in the $S_1$ state and the Franck-Condon factor involved in the $S_2\;{\rightarrow}\;S_1$ internal conversion is small, the $S_2\;{\rightarrow}\;S_o$ emission alone appears. Because the molecular planarity is improved at the interior of the micelle, the excited state intramolecular charge transfer in the $S_1$ state is extended, and the excited state is more tolerable for any quenching effects in the micelle. Therefore, an $S_1\;{\rightarrow}\;S_o$ emission was newly discovered under this micelle microenvironment. For the $S_2\;{\rightarrow}\;S_o$ emission, the quantum yields increase but the quantum yield of the $S_1\;{\rightarrow}\;S_o$ emission approximately decreases as the water concentration in the micelle increases.

• 생약학회지
• /
• 제25권3호
• /
• pp.199-203
• /
• 1994

Chemical examination of the leaves of Betula platyphylla var. latifolia has led to the isolation and characterization of five flavonoid glycosides including two C-glucosyl flavonoids. The structures of these compounds were elucidated as myricetin $3-O-{\alpha}-_L-rhamnoside$ (myricitrin), $quercetin-3-O-{\beta}-_D-glucopyranoside$ (isoquercitrin), $quercetin-3-O-{\beta}-_D-glucopyranoside$ (hyperoside), $nalingenin-6-C-{\beta}-_D-glucopyranoside$ (hemiphloin) and $aromadendrin-6-C-{\beta}-_D-glucopyranosidre(6-C-glucosyldihydrokaempferol)$ on the basis of physico-chemical and spectroscopic evidences.

• Natural Product Sciences
• /
• 제9권4호
• /
• pp.245-248
• /
• 2003

A phytochemical investigation on the methanolic extract of Cosmos caudatus has led to the isolation of quercetin $3-O-{\beta}-D-arabinofuranoside$ (1), quercetin $3-O-{\beta}-D-rhamnoside$ (2), quercetin $3-O-{\alpha]-D-glucoside$ (3) and quercetin (4). These compounds were shown to be the antioxidative constituents of the plant when evaluated using the ferric thiocyanate (FTC) and thiobarbituric acid (TBA), and radical scavengers based on the 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging assays.