• Polymer(Korea)
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• v.37 no.3
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• pp.347-355
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• 2013

In this study, the porous cellulose hydrogel as a carrier to enhance the skin delivery of quercetin and its glycoside, rutin known as flavonoid antioxidants was prepared and its properties were investigated. The optimum cellulose hydrogel for quercetin and rutin was made by the reaction of 2 wt% cellulose with 12% ECH. In the release test of the hydrogel containing the flavonoids, the release of quercetin was diffusion-controlled at $10{\sim}500{\mu}M$, but rutin was released by the erosion of hydrogel system at $10{\sim}50{\mu}M$. Both the encapsulation efficiency and release amount of rutin in hydrogel were higher than quercetin. However, in skin permeation experiment using Franz diffusion cell, quercetin showed higher skin permeation capacity than rutin. The hydrogel containing flavonoids showed remarkable transdermal permeation than the control group. These results suggest that porous cellulose hydrogel is potential drug delivery system to enhance transdermal permeation of water-insoluble flavonoid antioxidants.

• Journal of the Korean Magnetic Resonance Society
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• v.22 no.3
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• pp.54-63
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• 2018

Nymphaea tetragona, also known as waterlilies, is aquatic plant in the family of Nymphaeceae. Three flavonoids(3, 4, and 5) and one mixed flavonoids were separated from this plant. The mixed flavonoid consisted of two flavonoids; a well-known quercetin(1) and a new natural flavonoid(2). The latter also has two chiral centers and their configurations were established by ROESY experiment. Two glycoflavonoids were determined as isoquercetin and quercetin-3-O-${\beta}$-xyropyranosyl-($1{\rightarrow}2$)-${\beta}$-galactopyroside. The $^1H$ NMR spectra for 4 and 5 dissoloved in $DMSO-d_6$ solvent showed resonance proximity and and severely overlap in the glycoside region, hindering the determination of the configurations of the stereogenic centers of the sugar moieties. This problem was solved through the spin simulation. Here, the exact NMR parameters for the sugar moieties of 4 and 5 were listed.

• Food Science and Biotechnology
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• v.15 no.3
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• pp.424-430
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• 2006

Low molecular weight polyphenols were isolated from hot water extracts of radiata pine (Pinus radiata) bark using a Sephadex LH-20 column and characterized by $^1H$ and $^{13}C$ NMR, UV, FT-IR, and GC-MS analyses. Major compounds isolated and identified were protocatechuic acid, trans-taxifolin, and quercetin. Trans-taxifolin, an important intermediate in biosynthetic route of proanthocyanidin (PA), was isolated in large quantities and indicates that PA is a major component of radiata pine bark. Small amounts of polyphenols were identified by GC-MS analysis. The presence of p-hydroxybenzoic acid, vanillic acid, protocatechuic acid, cis- and trans-feruic acid, p-coumaric acid, trans-caffeic acid, (-)-epicatechin, (+)-catechin, trans- and cis-taxifolin, (+)-gallocatechin, and quercetin was confirmed by comparison of mass fragmentation patterns and retention times (RT) with authentic samples. In addition, the presence of astringenin, astringenin glycoside, trans- and cis-leucodelphinidin was strongly assumed from characteristic mass fragment ions due to their conjugated structure and retro Diels-Alder reaction, and also from biosynthetic route of PA. GC-MS analysis allowed us to detect small amounts of phenolic acids and flavonoids and eventually discriminate trans- and cis-configuration in the identified polyphenols.

• Journal of Microbiology and Biotechnology
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• v.9 no.5
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• pp.661-667
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• 1999

The effect of fungal elicitor and heavy metal salts on the production of flavonol glycosides in cell cultures of Ginkgo biloba was investigated. Among the fungi tested, Trichoderma longibrachiatum ATCC 52326 was found to be the most efficient in the production of flavonol glycosides. Kaempferol production from the elicited callus increased ten-fold as compared to the unelicited callus, while quercetin concentration of elicited cells was nine-fold higher than that of uneliceited cells in suspension cultures. The maximum quercetin concentration of 0.362㎎/l was obtained in 1.25㎎/l of the homogenate elicitor. Among the heavy metal salts tested, CuSO₄ showed a significant effect on quercetin accumulation, reaching to the concentration of 0.526 ㎎/l. Quercetin concentration increased to a maximum of l2-fold in response to CuSO₄ treatment as compared to that of untreated cells. The phenylalanine ammonia-lyase (PAL) activity and flavonol glycosides production simultaneously increased for 5 days of culture after fungal elicitor feeding, and their contents showed the same proportional patterns during the culture period. In contrast, PAL activity of cell cultures treated with CuSO₄ was almost constant during the culture period, although quercetin production increased remarkably.

• Applied Chemistry for Engineering
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• v.26 no.2
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• pp.165-172
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• 2015

Quercetin and its glycoside, rutin, are flavonoids, which are well known as natural antioxidants. In this study, cationic liposomes loaded with flavonoids (quercetin or rutin) were investigated for their effects on cell and skin permeability, and protective effects against UVA. The particle size of the empty cationic liposomes was in the range of 100~130 nm, and the zeta potential was + 33.05 mV. The entrapment efficiency of 0.5R/CL was higher than that of 0.5 Q/CL. The cellular uptake of the cationic liposomes was five-fold higher than that of liposomes. The skin permeability of quercetin and rutin was investigated using Franz diffusion cells. Compared to the initial loading dose, the amount of quercetin or rutin delivered to the skin by cationic liposomes was higher than that delivered by conventional liposomes or phosphate-buffered saline. From the protective effect of cationic liposomes against UVA ($25J/cm^2$), we found that the cell viability in cationic liposomes containing flavonoids was higher than that of using UVA irradiation only. These results indicate that cationic liposomes provide enhanced delivery of flavonoids (quercetin and rutin) into the skin and may be used for antiaging and antioxidant cosmetics.

• Korean journal of food and cookery science
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• v.25 no.1
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• pp.31-38
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• 2009

The noodle is one of the most popular meal as a main dish in Korea and onions are reported to contain high levels of flavonoids such as quercetin, aglycone, and quercetin 4-glycoside. This study was conducted to develop the wet noodle with onion juice and to examine the cooking quality, textural properties of it. Five sensory attributes such as gloss, chewiness, adhesiveness, odor, and taste were used for sensory evaluations. Optimal amount of onion(149.5 g) and salt (6.5 g) satisfied target sensory score(7.0) was suggested by response surface methodology. The wet noodle with optimal amount of onion juice and salt was tasted by 100 consumer and showed high score(6.67) in overall acceptability. Cooking quality was measured through absorption of water, volume, degree of turbidity. The volume, water absorption, and cooking water turbidity of cooked wet noodle with onion juice(experimental noodle) were significantly(p<0.01) higher than the control one. Texture profile analysis of experimental noodle showed a lower score of hardness, adhesiveness, springiness, and chewiness. However, it appeared that the experimental noodle showed higher score for cohesiveness than the control noodle.

• Archives of Pharmacal Research
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• v.27 no.7
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• pp.751-756
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• 2004

Flavonoids have been demonstrated to exhibit a wide range of biological activities including anti-inflammatory and neuroprotective actions. Although a significant amount of flavonoids has been identified to be present as glycosides in medicinal plants, determinations of the biological activities of flavonoids were mainly carried out with aglycones of flavonoids. Therefore, the exact role of the glycosidation of flavonoid aglycones needs to be established. In an attempt to understand the possible role of glycosidation on the modulation of the biological activities of flavonoids, diverse glycosides of kaempferol, quercetin, and aromadendrin were examined in terms of their anti-inflammatory activity determined with the suppression of lipopolysaccharide (LPS)-induced nitric oxide (NO) production in BV2 microglial cells. The results indicated that glycosidation of aglycones attenuated the suppressive activity of aglycones on LPS-induced NO production. Although attenuated, some of glycosides, depending on the position and degree of glycosidation, maintained the inhibitory capability of LPS-induced NO production. These findings suggest that glycosidation of flavonoid aglycones should be considered as an important modulator of the biological activities of flavonoids.

• Korean Journal of Food Science and Technology
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• v.53 no.1
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• pp.40-45
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• 2021

Prior studies of physiologically active substances in grapes have focused only on the fruit, pericarp, and branches, as well as the pulp and seeds. The present study assessed the changes in quercetin-3-O-glucuronide (Q3OG) and flavonol glycoside content using grape leaves from Vitis labruscana B. and V. coignetiae at different growth stages and provided basic data for quality control. Content analysis showed that both varieties differed in Q3OG and flavonol glycoside content by growth stage, and the components were found to be high in the order of fruit, maturation, and coloration. Also, Vitis labruscana B. has a better vascular relaxation effect than Vitis coignetiae. These results suggest that in the use of grape leaves as a functional raw material, Q3OG and flavonol glycosides can be used as indicator components. In addition, if raw materials for each growth stage are mixed in a particular ratio, it will be a way to manage the specific efficacy and content of indicator components.

• Korean Journal of Medicinal Crop Science
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• v.19 no.4
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• pp.251-256
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• 2011

The leaves of Hippophae rhamnoides were extracted with methanol and then further fractioned with hexane, ethyl acetate, butanol and water in order to investigate biological activity. Two flavonol glycosides were isolated and identified from ethyl acetate soluble fraction, which showed the strongest antioxidant activity ($RC_{50}$ = 4.33 ${\mu}g/ml$). Isolated two compounds have shown strong free radical scavenging activity. Especially, quercetin 3-O-glucoside ($RC_{50}$ = 2.60 ${\mu}g/ml$) was more active than ${\alpha}$-tocopherol ($RC_{50}$ = 4.67 ${\mu}g/ml$). Total phenol and flavonoid contents were the highest to 4.17 and 1.14 mg/ml in the ethyl acetate soluble fraction. In addition, ethyl acetate soluble fraction was shown to the strongest ${\alpha}$-glucosidase inhibitory activity ($IC_{50}$ = 137.88 ${\mu}g/ml$) among the fractions. The results suggest that leaves of H. rhamnoides could be a potential source of natural antioxidant.

• Proceedings of the Plant Resources Society of Korea Conference
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• 2018.04a
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• pp.13-13
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• 2018

The anti-inflammatory (INF) compounds (1-15) were isolated from Agrimonia pilosa Ledeb. (APL) by activity-guided isolation technique. The isolated compounds (1-15) were identified as quercetin-7-O-rhanmoside (1), apigenin-7-O-glycoside (2), kaempferol-7-O-glycoside (3), apigenin-7-O-[6"-(butyl)-glycoside] (4), querceitn (5), kaempferol (6), apigenin (7), apigenin-7-O-[6"-(pentyl)-glycoside] (8), agrimonolide (9), agrimonolide-6-O-glucoside (10), desmethylagrimonolide (11), desmethylagrimonolide-6-O-glucoside (12), luteolin (13), vitexin (14) and isovitexin (15). Flavonoids, compound 2, 3, 11, and 14-15 have been found in APL for the first time. Furthermore, two novel flavone derivatives, compound 4 and 8, have been isolated inceptively in plant. In the no cytotoxicity concentration ranges of $0-20{\mu}M$, nitric oxide (NO) production level of 1-15 was estimated in LPS-treated Raw 264.7 macrophage cells. The flavone aglycones, 7 (apigenin, $IC_{50}=3.69{\pm}0.34{\mu}M$), 13 (luteolin, $IC_{50}=4.62{\pm}0.43{\mu}M$), 6 (kaempferol, $IC_{50}=14.43{\pm}0.23{\mu}M$) and 5 (quercetin, $IC_{50}=19.50{\pm}1.71{\mu}M$), exhibited excellent NO inhibitory (NOI) activity in dose-dependent manner. In the structure activity relationship (SAR) study of apigenin-derivatives (APD), apigenin; Api, apigenin-7-O-glucoside; Api-G, apignenin-7-O-[6"-(butyl)-glycoside]; Api-BG and apignenin-7-O-[6"-(pentyl)-glycoside]; Api-P, from APL on INF activity was investigated. The INF mediators level such as NO, INF-cytokines, NF-KB proteins, iNOS and COX-2 were sharply increased in Raw 264.7 cells by LPS. When pretreatment with APD in INF induced macrophages, NOI activity of Api was most effective than other APD with $IC_{50}$ values of $3.69{\pm}0.77{\mu}M$. And the NOI activity was declined in the following order: Api-BG ($IC_{50}=8.91{\pm}1.18{\mu}M$), Api-PG ($IC_{50}=13.52{\pm}0.85{\mu}M$) and API-G ($IC_{50}=17.30{\pm}0.66{\mu}M$). The NOI activity of two novel compounds, Api-PG and Api-BG were lower than their aglycone; Api, but more effective than Api-G (NOI: Api-PG and Api-BG). And their suppression ability on INF cytokines such as $TNF-{\alpha}$, $IL-1{\beta}$ and IL-6 mRNA showed the similar tendency. Therefore, the anti-INF mechanism study of Api-PG and Api-BG on nuclear factor-kappa B ($NF-{\kappa}B$) pathway, representative INF mechanism, was investigated and Api was used as positive control. Api-BF was more effectively prevent the than phosphorylation of $pI{\kappa}B$ kinase (p-IKK) and p65 than Api-PG in Raw 264.7 cells. In contrast, Api-PG and Api-BG were not reduced the phosphorylation of inhibitor of kappa B alpha ($I{\kappa}B{\alpha}$). Moreover, pretreatment with Api-PG and Api-BG, dose-dependently inhibited LPS-induced expression of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) mRNAs and proteins in macrophage cells, and their expression were correlated with their NOI activity. Therefore, APL can be utilized to health promote agent associated with their AIN metabolites.