• Natural Product Sciences
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• 제26권4호
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• pp.326-333
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• 2020

The aerial parts of Eclipta prostrata is used as a traditional medicine and vegetable. In traditional folk medicine, it is used for treatment of hemorrhages, hepatic, disease, renal injuries, hair loss, tooth mobility, and viper bites. In this study, ten compounds (1 - 10) were isolated from the aerial parts of E. prostrata. A reliable high performance liquid chromatography equipped with photometric diode array detector (HPLC-PDA) method was developed to simultaneously quantitate 10 marker compounds [chlorogenic acid (1), paratensein 7-O-��-ᴅ-glucoside (2), quercetin 7-O-��-ᴅ-glucoside (3), luteolin 7-O-��-ᴅ-glucoside (4), apigenin 7-O-��-ᴅ-glucoside (5), apigenin 4'-O-��-ᴅ-glucoside (6), apigenin (7), luteolin (8), wedelolactone (9), and paratensein (10)]. In addition, compounds 5 and 6 showed considerable inhibitory effects against protein-tyrosine phosphatase 1B (PTP1B) enzyme. Moreover, compounds 6 - 8, and 10 exhibited potent α-glucosidase inhibitory effects with IC50 values of 24.5 ± 1.9, 33.0 ± 0.5, 45.5 ± 0.1, and 23.8 ± 1.0 µM, respectively. All compounds (1 - 10) showed considerable acetylcholinesterase (AChE) inhibitory effects with IC50 ranging from 30.1 to 75.2 µM.

• Journal of Applied Biological Chemistry
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• 제51권2호
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• pp.57-60
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• 2008

Eight compounds, including 2 flavones, luteolin (1) and apigenin (2), 2 flavonols, kaempferol (3) and quercetin (4), and 4 flavonoid glucosides, luteolin-7-O-${\beta}$-D-glucoside (5), apigetrin (6), astragalin (7), and isoquercitrin (8), isolated from the whole herb of Sonchus oleraceus L. were analyzed on the basis of chemical and spectroscopic evidence. This was the first time to report compounds 3, 4, 6, 7 and 8 from the Sonchus oleraceus L. The antioxidant activities of the isolated flavonoids and their glucoside derivatives were evaluated by DPPH free radical-scavenging assay, showing that compounds 1, 3, 4 and 8 exhibited stronger antioxidant activities compared with ${\alpha}$, tocopherol and curcumin. Flavonoids containing more hydroxyl groups exhibited better antioxidant activities. The antioxidant activity of flavonols was superior to their corresponding flavones, and that of aglycone are more potent than their glucoside derivatives.

• Journal of Applied Biological Chemistry
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• 제51권1호
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• pp.13-16
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• 2008

Five anthraquinones, emodin (1), ${\omega}$-hydroxyemodin (2), chrysophanol-8-O-${\beta}$-D-glucoside (3), emodin-8-O-${\beta}$-D-glucoside (4), and physcion-8-O-${\beta}$-D-glucoside (5), and five flavonoids, kaempferol-3-O-${\beta}$-D-glucoside (6), quercetin (7), quercitrin (8), isoquercitrin (9), and (+)-catechin (10), were isolated from the EtOAc-soluble extract of the fruits of Rumex japonicus. The structures of 1-10 were identified by spectroscopic methods including NMR studies. This is the first report on the isolation of compounds 3-5 from this plant. The isolates were subjected to in vitro bioassays to evaluate their inhibitory activities on the rat lens aldose reductase (RLAR), among which two anthraquinones (1 and 4), and five flavonols (5-9) showed significant activities on RLAR.

• 대한화장품학회지
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• 제34권3호
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• pp.157-165
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• 2008

이전 연구에서 저자들은 나문재 추출물의 항산화 작용과 추출물 함유 크림의 유화 안정성에 대한 결과를 보고한 바 있다[1,2]. 본 연구에서는 thin layer chromatography(TLC), high performance liquid chromatography (HPLC)와 liquid chromatography/Electrospray Tandem mass spectrometry (LC/ESI/MS/MS), $^1H$-NMR을 이용하여 나문재 추출물에 대한 성분 분석을 수행하였다. 나문재 추출물 중 ethyl acetate분획의 TLC는 5개의 띠($SA1{\sim}SA5$)로 분리되었다. Ethyl acetate 분획의 당 제거반응 후 얻어진 aglycone 분획에 대한 HPLC 크로마토그램은 2개의 피이크(SAA 2 및 SAA 1)를 나타냈고, 각각 그 용리 순서는 quercetin, kaempferol이었으며 조성비는 quercetin 16.88%, kaempferol 83.12%로 kaempferol의 함량이 큰 것으로 나타났다. 또한 LC/ESI-MS/MS를 통해서 SA 2는 kaempferol-3-O-gluco-side로 SA 3는 quercetin-e-O-glucoside, SA 4는 kaempferol-3-O-rutinoside, SA 5는 quercetin-3-O-rutinoside로 확인되었다. LC/ESI-MS/MS의 스펙트럼에서 SAA 1은 탈양성자화된 aglycone 분획에 상용하는 분자이온 $[M-H]^$-(m/z285) 피이크를 나타냈으며, $^1$v 분석을 실시한 결과 [${\delta}$ 6.19 (1H, d, J=1.8Hz, H-6), ${\delta}$ 6.44 (1H, d, J=1.8Hz, H-8), ${\delta}$ 6.92 (2H, d, J=9.0Hz, H-3',5'), ${\delta}$ 8.04 (2H, d, J=9.0Hz, H-2',6')]에서 피이크들이 나타났다. 따라서 SAA 1은 kaempferol임이 확인되었다. SAA 2는 aglycone 분획에 상응하는 분자이온 $[M-H]^-$ (m/z 301)을 생성하였고, $^1H$-NMR 스펙트럼은 [${\delta}$ 6.20 (1H, d, J=2.0Hz, H-6), ${\delta}$ 6.42 (1H, d, J=2.0Hz, H-8), ${\delta}$ 6.90 (1H, d, J=8.6Hz, H-5'), ${\delta}$ 7.55 (1H, dd, J=8.6, 2.2Hz, H-6'), ${\delta}$ 7.69 (1H, d, J=2.2Hz, H-2')]에서 피이크들을 나타냈고, 따라서 SAA 2는 quercetin으로 확인되었다. 결론적으로, 이미 보고된 나문재 추출물의 항산화 작용 그리고 안정성 실험과 더불어 나문재 추출물의 성분분석은 새로운 기능성 화장품원료로서 응용이 가능함을 시사한다.

• Natural Product Sciences
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• 제19권2호
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• pp.137-144
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• 2013

Phytochemical constituents were isolated from the seeds of tartary buckwheat (Fagopyrum tataricum) by open column chromatography. Their structures were elucidated as ${\beta}$-sitosterol (1), ${\beta}$-sitosterol-3-O-glucoside (2), oleanolic acid (3), kaempferol (4), quercetin (5), kaempferol-3-O-rutinoside (6), and quercetin-3-O-rutinoside (7) on the basis of spectroscopic analysis including $^1H$-, $^{13}C$-NMR, and MS. To our knowledge, oleanolic acid (3) has been isolated for the first time from the seeds of Fagopyrum species. The total contents of compounds 4 - 7 were 0.500 mg/g in Daesan maemil, 0.312 mg/g in Yangjul maemil, and 2.185 mg/g in tartary buckwheat.

• Natural Product Sciences
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• 제17권3호
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• pp.221-224
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• 2011

A $CH_3Cl$ extract from the flower of Lonicera japonica (Lauraceae) significantly protected primary cultures of rat cortical cells injured by the excitotoxic amino acid, L-glutamate. Loganin (1), secoxyloganin (2), caffeic acid (3) rutin (4), hyperoside (5), quercetin-3-O-glucoside (6), lonicerin (7), kaempferol-3-O-rutinoside (8), luteolin-7-O-b-D-glucopyranoside (9), quercetin (10) and luteolin (11) were isolated by bioactivity-guided fractionation from the $CH_3Cl$ fraction and further separated using chromatographic techniques. Caffeic acid, lonicerin, kaempferol-3-O-rutinoside, quercetin and luteolin had significant neuroprotective activities against glutamate-induced neurotoxicity in primary cultures of rat cortical cells at concentrations ranging from $0.1{\mu}M$ to $10.0\;{\mu}M$.

• International Journal of Advanced Culture Technology
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• 제7권3호
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• pp.120-125
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• 2019

In this paper, we have isolated six phenolic compounds, such as (+)-catechin (1), taxifolin (2), taxifolin-3-O-${\beta}$-D-(+)-xylose (3), quercetin (4), quercetin-3-O-${\alpha}$-L(+)-rhamnose (quercitrin) (5), apigenin-8-C-rhamnosyl-(1'''${\rightarrow}$2'')-glucoside (2''-O-rhamnosylvitexin) (6) from the EtOAc(Ethyl Acetate) and $H_2O$ soluble fractions of Japanese anise(Illicium anisatum L) leaves and twigs. Also, we have evaluated antioxidative and antiviral activity for each isolated compound. The antioxidative test was DPPH (1,1-diphenyl-2-picrylhydrazyl) radical scavenging activity. According to the experimental results, all of the isolated compounds indicated the increased radical scavenging activities as the concentration increases and most of the isolated compounds indicated generally good antioxidative values compare to the controls, ascorbic acid and ${\alpha}$-tocopherol. In the antiviral activities, all of the isolated compounds had no potentials in rhinovirus 1B (HRV 1B). But in enterovirus 71 (EV 71) and Influenza virus A/PR/8 (Influenza PR8), only quercetin (4) indicated the good antiviral activity compare to the control. Based on the above results, we found that the phenolic compounds of Japanese anise may be applied for one of the natural biomass sources that can be used as an antioxidant and an antiviral substance.

• Preventive Nutrition and Food Science
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• 제8권4호
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• pp.365-371
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• 2003

The potential of seven flavonoid glycosides to induce quinone reductase (QR), an anticarcinogenic marker enzyme, in murine hepatoma cells (hepalc1c7) and its mutant cells (BPRc1) was evaluated. Among test compounds, kaempferol-3-O-glucoside, luteolin-6-c-glucoside, and quercetin-3-O-glucoside (Q-3-G) induced QR in hepalc1c7 cells in a dose-dependent manner. However, in BPRc1 cells lacking arylhydrocarbon receptor nuclear translocator (ARNT), only Q-3-G caused a significant induction of quinone reductase at the concentration range of 0.5 to 8 ug/mL, suggesting that it is a monofunctional inducer. Q-3-G induced not only phase 2 enzymes, including QR and glutathione-S-transferase, but also nitroblue tetrazolium reduction activity in HL-60 cells, a biochemical marker for cell differentiation promoting agents. In conclusion, Q-3-G merits further study to evaluate its cancer chemopreventive potential.

• 생약학회지
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• 제54권2호
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• pp.53-60
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• 2023

Athyrium acutipinnulum, called as Ulleungdo ladyfern (Seom-go-sa-ri), is a native plant of South Korea. A. acutipinnulum has been consumed as foods and also traditionally used for the treatment of epilepsy, gonorrhea and nerve disorder. The methanolic extract and EtOAc soluble fraction of A. acutipinnulum showed the antioxidant activity. Fractionation using various chromatographic techniques resulted in the isolation of 13 compounds. The structures were elucidated on the basis of spectroscopic methods as seven phenolic compounds, methyl 2-hydroxy-3-phenylpropanoate (1), protocatechualdehyde (2), caffeic acid (3), trans-p-coumaric acid (4), (-)-4-E-caffeoyl-L-threonic acid (5), 5-O-caffeoyl shikimic acid (6) and 5-O-caffeoyl quinic acid (7), three flavonoids, quercetin 3-O-β-glucoside (8), naringenin-7-O-β-glucoside (9) and sutchenoside A (10), two steroids, ponasterone A (11) and ecdysone (12) and a coumarin, esculetin (13). Among them, compounds 5 and 10 were first reported from Athyrium spp and compounds 2, 5, 6 and 7 showed the antioxidant activity.

• Archives of Pharmacal Research
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• 제28권7호
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• pp.791-798
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• 2005

The hepatoprotective activity of flavonol glycosides rich fraction (F-2), prepared from 70% alcohol extract of the aerial parts of V calcarata Desf., was evaluated in a rat model with a liver injury induced by daily oral administration of $CCl_4$ (100 mg/kg, b.w) for four weeks. Treatment of the animals with F-2 using a dose of (25 mg/kg, b.w) during the induction of hepatic damage by $CCl_4$ significantly reduced the indices of liver injuries. The hepatoprotective effects of F-2 significantly reduced the elevated levels of the following serum enzymes: alanine aminotransferase (ALT), aspartate aminotransferase (AST), alkaline phosphatase (ALP) and lactate dehydrogenase (LDH). The antioxidant activity of F-2 markedly ameliorated the antioxidant parameters including glutathione (GSH) content, glutathione peroxidase (GSH-Px), superoxide dismutase (SOD), plasma catalase (CAT) and packed erythrocytes glucose-6-phosphate dehydrogenase (G6PDH) to be comparable with normal control levels. In addition, it normalized liver malondialdehyde (MDA) levels and creatinine concentration. Chromatographic purification of F-2 resulted in the isolation of two flavonol glycosides that rarely occur in the plant kingdom, identified as quercetin-3,5-di-O-$\beta$-D-diglucoside (5) and kaempferol-3,5-di-O-$\beta$-D-diglucoside (4) in addition to the three known compounds identified as quercetin-3-O-$\alpha$-L-rhamnosyl- (${\rightarrow}6$)-$\beta$-D-glucoside [rutin, 3], quercetin-3-O-$\beta$-D-glucoside [isoquercitrin, 2] and kaempferol-3-O-$\beta$-D-glucoside [astragalin, 1]. These compounds were identified based on interpretation of their physical, chemical, and spectral data. Moreover, the spectrophotometric estimation of the flavonoids content revealed that the aerial parts of the plant contain an appreciable amount of flavonoids (0.89%) calculated as rutin. The data obtained from this study revealed that the flavonol glycosides of F-2 protect the rat liver from hepatic damage induced by $CCl_4$ through inhibition of lipid peroxidation caused by $CCl_4$ reactive free radicals.