• 폴리머
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• 제37권3호
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• pp.347-355
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• 2013

본 연구에서는 항산화제인 quercetin과 그 배당체인 rutin의 피부 흡수를 증진시키기 위한 전달체로 다공성 셀룰로오스 하이드로젤을 제조하였고 그 특성을 연구하였다. Quercetin과 rutin을 위한 최적의 하이드로젤을 가교제인 12% epichlorohydrin(ECH)과 2% 셀룰로오스를 반응용액으로 하여 만들었다. 플라보노이드 함유 하이드로젤의 방출 실험에서, quercetin의 방출은 $10{\sim}500{\mu}M$ 농도에서 확산 속도에 영향을 받았으나, rutin의 경우는 비교적 낮은 농도($10{\sim}50{\mu}M$)에서 하이드로젤의 침식에 의한 방출이 지배적이었다. 플라보노이드에 대한 하이드로젤의 포집효율과 방출량은 quercetin보다도 rutin에서 모두 크게 나타났다. 하지만, Franz diffusion cell을 이용한 피부 투과 실험에서 quercetin이 rutin보다 1.2배나 더 큰 피부 투과능을 나타냈다. 플라보노이드 함유 하이드로젤은 대조군인 20% 1,3-butylene glycol phosphate buffer에서보다도 더 큰 경피 투과능을 나타내었다. 이 결과들은 난용성 항산화제인 플라보노이드의 피부 흡수 증진 전달체로서 셀룰로오스 다공성 하이드로젤이 이용 가능성이 있음을 시사한다.

• 한국자기공명학회논문지
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• 제22권3호
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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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• 제15권3호
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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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• 제9권5호
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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.

• 공업화학
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• 제26권2호
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• pp.165-172
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• 2015

쿼세틴과 쿼세틴의 배당체인 루틴은 천연 항산화제로 잘 알려진 플라보노이드이다. 본 연구에서는 플라보노이드(쿼세틴과 루틴)를 담지한 양이온 리포좀을 제조하여 세포 및 피부 투과성과 자외선(UVA)에 대한 HaCaT 세포 보호 효과를 평가하였다. 빈 양이온 리포좀의 입자 크기는 100~130 nm이며, 입자 표면 전위는 + 33.05 mV를 나타내었다. 포집효율은 루틴을 담지한 리포좀과 양이온 리포좀이 쿼세틴을 담지한 경우보다 높았다. 세포 내 이입율 비교결과, 양이온 리포좀이 일반 리포좀에 비해 약 5배 정도 높음을 확인했다. In vitro 상에서, 쿼세틴과 루틴이 용해된 PBS (phosphate-buffered saline) 수용액, 동량의 쿼세틴과 루틴을 담지한 리포좀과 양이온 리포좀의 피부투과율을 비교하였다. 양이온 리포좀에 담지하였을 경우 가장 높은 피부투과율을 보였다. 플라보노이드를 담지한 양이온 리포좀의 자외선(UVA $25J/cm^2$)에 대한 HaCaT 세포 보호 효과를 측정한 결과, 자외선만 조사한 군에 비해 플라보노이드 담지 양이온 리포좀을 처리한 군에서 높은 세포 보호 효과를 보였다. 결과적으로, 양이온 리포좀은 플라보노이드를 피부 속으로 전달하는데 있어서 매우 유용한 피부 전달 시스템임을 확인하였다. 따라서, 세포 보호 및 피부 흡수 증진 효과를 가지는 양이온 리포좀은 항노화 및 항산화 화장품 제형으로써 활용 가능성이 있음을 시사한다.

• 한국식품조리과학회지
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• 제25권1호
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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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• 제27권7호
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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.

• 한국식품과학회지
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• 제53권1호
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• pp.40-45
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• 2021

본 연구의 목적은 켐벨얼리 품종과 머루 품종의 포도 잎을 생육단계별로 채취하여 Q3OG 및 플라보놀 배당체(quercetin, kaempferol, isorhamnetin)의 함량 변화와 혈관 이완 효과를 평가하여 기능성 소재로 활용하기 위한 품질관리 기초 자료를 제공하는 것이다. 포도의 생육단계는 전엽기, 개화기, 결실기, 착색기 및 성숙기로 구분되는데, 산업적으로 포도 잎 원료 확보가 쉬운 결실기, 착색기 및 성숙기 포도 잎을 대상으로 분석했다. 시험 결과 두 품종 모두 생육단계별로 Q3OG 및 플라보놀 배당체 함량의 차이가 있었고, 결실기>성숙기>착색기 순으로 성분들의 함량이 높은 것으로 확인되었다. 생육단계별 혈관 이완 효과는 두 품종 모두 혈관 이완 효과를 보였으며 켐벨얼리 포도 잎이 머루 포도 잎보다 더 좋은 것으로 나타났다. 이는 포도잎 추출물의 기능성 소재 활용 가능성을 보여주었다. 물론, 안타깝게도 Q3OG 및 플라보놀 배당체 성분이 혈관 이완 효과를 대표하는 효능성분은 아닌 것으로 판단되지만, 착색기 포도 잎에 비하여 결실기와 성숙기에 함량이 높은 Q3OG 및 플라보놀 배당체가 지표성분으로 써의 가치는 있다고 판단된다. 따라서 포도 잎을 기능성 원료로 활용 시 Q3OG 및 플라보놀 배당체를 지표성분으로 활용하고, 각 생육단계별 포도 잎 원료를 일정 비율로 혼합하여 사용하면 일정한 효능과 지표성분 함량을 관리하는 방법이 되리라 생각한다.

• 한국약용작물학회지
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• 제19권4호
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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.

• 한국자원식물학회:학술대회논문집
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• 한국자원식물학회 2018년도 춘계학술발표회
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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.