• Journal of Applied Biological Chemistry
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• 제65권4호
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• pp.247-252
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• 2022

황해쑥을 MeOH : H₂O =70:30 용매로 추출하고, 얻어진 추출물을 EtOAc n-BuOH 및 water로 용매 분획 하였다. 이 중 n-BuOH 분획으로부터 silica gel (SiO₂)과 octadecyl silica gel (ODS) column chromatography로 정제하여 4종의 화합물을 분리하였다. Nuclear magnetic resonance 및 mass spectrometry 등의 스펙트럼 데이터를 통해 화합물의 화학구조를 (2S)-naringenin (1), 3-methylkaempferol (2), 3,3'-dimethylquercetin (3), and 3,3',4'-trimethylquercetin (4) 로 구조 동정하였다. 분리한 화합물 4종은 황해쑥에서는 처음 분리동정 되었다. 본 연구를 통해 glutathione mean의 증가와 glutathione heterogeneity 감소를 보인 황해쑥 유래 화합물 1-4가 세포내 글루타티온 (GSH) 수준을 균일하게 상승시키는 효능이 있음을 확인함으로써 항산화능을 확인하였다. 이러한 결과를 바탕으로 황해쑥의 기능성 소재로 활용가능성을 확인하였다.

• Journal of Applied Biological Chemistry
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• 제66권
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• pp.272-281
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• 2023

작약 뿌리는 monoterpene glycoside계 물질을 함유하고 있으며, 이들 화합물은 항경련, 항염증, 항바이러스, 신경보호 및 진정효과를 나타내는 것으로 알려져 있다. 이번 연구에서는 작약 뿌리의 dichloromethane (CH₂Cl₂) 및 ethyl acetate (EtOAc) 가용성 분획으로부터 세포독성 물질을 탐색하고자 하였다. 그 결과, 총 13종의 화합물을 분리할 수 있었으며, 이들의 세포독성 평가를 위해 사람 유래 폐암 선암 세포주인 A549에 처리하여 세포생존율 변화를 관찰하였다. A549에 대한 세포독성은 gallic acid (8) > (2S)-naringenin (9) > methyl gallate (10) > 6'-Obenzoylpaeoniflorin (7) > palmitic acid (3) 순으로 나타났다. 특히, 7은 normal cell인 MRC-5에 대한 독성은 없는 것으로 확인되었으며, 7의 A549 및 MRC-5 세포생존율에 미치는 영향에 대한 보고는 이번이 처음이다. 향후 7에 대한 세포독성 메커니즘 및 선택성과 관련된 추가연구가 필요할 것으로 판단된다.

• Journal of Microbiology and Biotechnology
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• 제19권4호
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• pp.387-390
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• 2009

Microbial UDP-glycosyltransferases can convert many small lipophilic compounds into glycons using uridine-diphosphate-activated sugars. The glycosylation of flavonoids affects solubility, stability, and bioavailability. The gene encoding the UDP-glycosyltransferase from Bacillus cereus, BcGT-3, was cloned by PCR and sequenced. BcGT-3 was expressed in Escherichia coli BL21(DE3) with a glutathione S-transferase tag and purified using a glutathione S-transferase affinity column. BcGT-3 was tested for activity on several substrates including genistein, kaempferol, luteolin, naringenin, and quercetin. Flavonols were the best substrates for BcGT-3. The enzyme dominantly glycosylated the 3-hydroxyl group, but the 7-hydroxyl group was glycosylated when the 3-hydroxyl group was not available. The kaempferol reaction products were identified as kaempferol-3-O-glucoside and kaempferol-3,7-O-diglucoside. Kaempferol was the most effective substrate tested. Based on HPLC, LC/MS, and NMR analyses of the reaction products, we conclude that BcGT-3 can be used for the synthesis of kaempferol 3,7-O-diglucose.

• Journal of the Korean Wood Science and Technology
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• 제38권2호
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• pp.159-164
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• 2010

Nine compounds, caffeic acid, naringenin, apigenin, luteolin, kaempferol, verbascoside, isoverbascoside, isocampneoside II, and cistanoside F, were isolated from the EtOAc and n-BuOH fractions of P. coreana bark. The structures of these compounds (1-9) were elucidated by spectroscopic methods and literature data. All the isolates were subjected to in vitro bioassay to evaluate their inhibitory activity against rat lens aldose reductase. Among these, compounds 6 and 8 indicated the significant inhibitory activity on rat lens aldose reductase with $IC_{50}$ values of 2.67 and 5.59 ${\mu}M$, respectively. Especially, The inhibition activity of acteoside was 3.9 times better than that of quercetin as a positive control (10.6 ${\mu}M$). These results suggested that phenylethanoid glycosides are likely to be the potential compounds for the prevention and/or treatment of diabetic complications.

• 대한암한의학회지
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• 제11권1호
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• pp.95-103
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• 2006

Objective: Gami-Samhwang-San, a herbal prescription for obesity treatment, is composed of seven crude herbs such as Ephedrae Herba, Scutellariae Radix, Acori Gramineri Rhizoma, Polygalae Radix, Typhae Pollen, Armeniacae Semen, Nelumbo Folium. This study was aimed to evaluate marker substances in n-butanol fraction (SH-21-B) from Gami-Samhwang-San by high performance liquid chromatography (HPLC). And we predicted inhibition activity of major compounds of Gami-Samhwang-San using Quantitative Structure Activity Relationships (QSAR) Methods: The separation was performed on a YMC J,sphere-H80 CI8(250${\times}$4.6 mm I.D) column by gradient elution with $H_3PO_4$ buffers in acetonitrile as the moblie phase at a flow-rate of 1.0ml/min. Results: HPLC was employed to determine the quantities and the qualities of several marker substances such as ephedrine, pseudoephedirne, baicalin, ${\beta}-asarone$, tenuifoliside, naringenin, amygdalin and hyperoside in the SH-21-B. Conclusion: We suggest this results could be a useful evidence for quality control of SH-21-B.

• Journal of Microbiology and Biotechnology
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• 제16권7호
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• pp.1090-1096
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• 2006

O-Methylation is a common modification reaction found in nature, and is mediated by an O-methyltransferase (OMT). OMTs have been mainly studied in plants, whereas only a few OMTs have been studied in microbes. When searching the Bacillus cereus genome, four putative small molecular OMTs were identified, among which BcOMT-1 was cloned and expressed in E. coli as a his-tag fusion protein. The whole cell expressing BcOMT-1 was used to methylate several flavonoids. Eriodictyol, luteolin, quercetin, and taxifolin, all of which contain 3' and 4' hydroxyl groups, served as methyl group acceptors for BcOMT-1, whereas naringenin, apigenin, 3,3'-dihydroxyflavone, and 3,4'-dihydroxyflavone did not function as substrates. Analysis of the reaction products using HPLC showed two different peaks, and NMR revealed that the methylation position was at the hydroxyl group of either carbon 3' or 4'. Therefore, this showed that BcOMT-1 used flavonoids containing ortho hydroxyl groups and transferred a methyl group to either of two hydroxyl groups.

• Molecules and Cells
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• 제25권2호
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• pp.247-252
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• 2008

There are several branch points in the flavonoid synthesis pathway starting from chalcone. Among them, the hydroxylation of flavanone is a key step leading to flavonol and anthocyanin. The flavanone 3-${\beta}$-hydroxylase (GmF3H) gene was cloned from soybean (Glycine max cultivar Sinpaldal) and shown to convert eriodictyol and naringenin into taxifolin and dihydrokaempferol, respectively. The major flavonoids in this soybean cultivar were found by LC-MS/MS to be kamepferol O-triglycosides and O-diglycosides. Expression of GmF3H and flavonol synthase (GmFLS) was induced by ultraviolet-B (UV-B) irradiation and their expression stimulated accumulation of kaempferol glycones. Thus, GmF3H and GmFLS appear to be key enzymes in the biosynthesis of the UV-protectant, kaempferol.

• Archives of Pharmacal Research
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• 제29권12호
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• pp.1102-1108
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• 2006

An in vitro bioassay-guide revealed that the methanol (MeOH) extract of the stem bark of Populus davidiana showed considerable inhibitory activity against cyclooxygenase (COX-1, COX-2). Continuous phytochemical study of the MeOH extract of this plant led to the isolation of ten flavonoids; sakuranetin (1), rhamnocitrin (2), 7-O-methylaromadendrin (3), naringenin (4), eriodictyol (5), aromadendrin (6), kaempferol (7), neosakuranin (8), sakuranin (9) and sakurenetin-5,4'-di-${\beta}$-D-glucopyranoside (10). Their structures were identified on the basis of their physicochemical and spectroscopic analyses. The isolated compounds, 1-10, were tested for their inhibitory activities against COX-1 and COX-2. Compound 7 was found to have potent inhibitory effect on COX-1 and a moderate effect on COX-2, meanwhile, compounds 1-6 showed moderate inhibition against COX-1 only. Moreover, compounds 5-8 exhibited suppressive effects on xanthine oxidase (XO). These results may explain, in part, the traditional uses of P. davidiana in ethnomedicine.

• Food Science and Biotechnology
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• 제18권5호
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• pp.1224-1229
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• 2009

The main objective of this study was to investigate possible application of citron (Citrus junos Sieb. ex TANAKA) seeds, which are massively produced as by-products during citron tea process, into functional food materials. First of all, citron seeds were germinated and produced citron shoots were examined for their functional properties. When contents of flavonoids in citron seeds and their germinated shoots were compared, naringenin, neohesperitin, and hesperitin were remarkably increased in shoots after germination while naringin and didymin were decreased. Concentrations of limonin and nomilin were decreased by germination otherwise their unidentified derivatives were newly formed. A methanol extract of citron shoot had lower $IC_{50}$ values [0.13 and 0.07 mg/mL for 2,2-diphenyl-1-picryl-hydrazyl (DPPH) and ABTS, respectively] than citron seed extract in radical scavenging activities. Addition of 500 mg/mL of citron shoot extract suppressed fat accumulation in 3T3-L1 adipocytes by 36.9%. Oral administration of olive oil along with citron shoot extract (33 mg/kg body weight) to Sprague Dawley rats effectively inhibited absorption of lipid into a body by decreasing blood triglyceride levels from 105.1 to 74.9 mg/dL 2 hr after olive oil administration. According to these results, citron shoot extract as a rich source of flavonoids can be utilized for functional food ingredients with effective antioxidant and anti-adipogenic properties.

• Archives of Pharmacal Research
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• 제17권2호
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• pp.71-75
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• 1994

The antimutagenic effects of 27 kinds of plant flavonoids on the mutagenicity of aflatoxin $B_1(AFB_1)$ and N-methyl-N'-nitro-N-nitrosoguanidine(MANG) in Salmonella typhimurium TA 100 were investigated. In the mixed applications of $AFB_1\;(1\;\mu{g/plate)}$ with the flavonoids $(300\;\mu{g/plate)}$ in the presence of a mammalian metabolic activation system (S9 mix), chrysin, apigenin, luteolin and its glucoside, kaempferol, fisetin, morin, naringenin, hesperetin, persicogenin, (+)-catechin and (-)epicatechin showed the antimutagenic effect against $AFB_1$ with more than 70% inhibition rate. A little or no antimutagenicities except flavone against MNNG $(0.5\;\mu{g/plate)}$ were observed. For the antimutagencity of the flavonoids on $AFB_1$, the flavonoid structure that contains the free 5, 7-hydroxyl gorup seemed to be essential. However, saturation of the 2, 3-double bond of elimination of the 4-keto group did not affect the activity.