• Natural Product Sciences
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• v.18 no.1
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• pp.32-38
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• 2012

The herbs of Orostachys japonicus (Crassulaceae) have been used to treat gastric cancer, gastric ulcer or hemorrhage. Flavonoid glycosides, mainly kaempferol (Kp)- and quercetin (Qc) glycosides, have been isolated from O. japonicus; however, no quantitative information on those flavonol glycosides and no peroxynitritescavenging activity of the Orostachys extracts have been reported. In this study, Kp- and Qc glycosides were qualitatively and quantitatively analyzed by high-performance liquid chromatography (HPLC) in eight Orostachys and a Meterostachys species including O. japonicas, O. margaritifolius, O. chongsunensis, O. minuta, O. ramosus, O. malacophylla, O. latiellipticus, O. iwarenge, O. iwarenge for. magnus, and Meterostachys sikokiana distributed or cultivated in Korea. Distinctively, O. margaritifolius contained two flavonol 3,7-di-O-glycosides of Kp 3,7-di-O-glucoside and Kp 3-rhamnosyl-7-glucoside, but O. japonicus had two flavonol 3-O-rutinosides, Kp 3-rutinoside and Qc 3-rutinoside. The three species of O. margaritifolius (24.36 mg/g MeOH extract), O. japonicus (21.28 mg/g), and O. minuta (19.50 mg/g) showed relatively higher flavonoid contents. The flavonol glycosides were analyzed using eight standard compounds (Kp, Qc, Qc 3-O-rhamnoside, Qc 3-O-glucoside, Kp 3- O-rutinoside, Qc 3-O-rutinoside, Kp 3-O-rhamnosyl-7-O-glucoside, Kp 3,7-di-O-glucoside). The present HPLC method was validated to verify the linearity, precision, and accuracy. In addition, the peroxynitrite-scavenging activity was also discussed.

• Applied Biological Chemistry
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• v.48 no.1
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• pp.98-102
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• 2005

The MeOH extracts obtained from whole plant of Trigonotis peduncularis Benth. were solvent fractionated using EtOAc, n-BuOH and water, successively. The EtOAc and n-BuOH fractions gave four flavonol glycosides through application of silica gel and octadecyl silica gel (ODS) column chromatographies. The chemical structures of the flavonol glycosides were determined by the interpretation of several spectral data including 2D-NMR as $kaempferol-3-O-{\beta}-{D}-glucopyranoside\;(astragalin,\;1),\;kaempferol-3-O-{\alpha}-{L}-rhamnopyranosyl\;(1{\rightarrow}6)-{\beta}-{D}-glucopyranoside\;(nicotiflorin,\;2),\;quercetin-3-O-{\alpha}-{L}-rhamnopyranosyl(1{\rightarrow}6)-{\beta}-{D}-glucopyranoside\;(rutin,\;3),\;quercetin-3-O-{\beta}-{D}-glucopyranoside\;(isoquercitrin,\;4)$. The flavonoids have been first isolated from this plant. Nicotiflorin $(100\;{\mu}g/ml)$ showed $68.3{\pm}1.2%$ of the inhibitory effect on hACAT1(human Acyl CoA: cholesterol transferase 1) activity.

• Journal of Korean Society of Forest Science
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• v.96 no.4
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• pp.408-413
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• 2007

The dried bark of Platycarya strobilacea were ground, extracted with 95% EtOH, concentrated, and one of EtOH extracts was fractionated with a series of n-hexane, dichloromethane and another was fractionated with a series of petroleumether, $Et_2O$, ethyl acetate on a separatory funnel. A portion of dichloromethane soluble was chromatographed on a Sephadex LH-20 column ($72.0{\times}5.0cm$) using EtOH-$CHCl_3$ (7:3, v/v) as eluent and A portion of $Et_2O$ soluble was chromatographed on a silica gel column ($42.0{\times}3.5cm$) using $CHCl_3$-MeOH (9:3, v/v) as eluent. The isolated compounds were identified by TLC, $^1H$-, $^{13}C$-NMR, HMBC and EI-MS. Two flavonoids and three flavonoid glycosides were isolated from the bark of P strobilacea. The structures were determined to quercetin (compound 1), myricetin (compound 2) as flavonol compounds and afzelin (compound 3), quercitrin (compound 4), myricitrin (compound 5) as flavonol glycosides, respectively, on the basis of spectrosopic data.

• Applied Biological Chemistry
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• v.50 no.4
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• pp.344-347
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• 2007

The aerial parts of Lespedeza cuneata were collected, air-dried and extracted with 95% aqueous EtOH. Then it was successively partitioned with n-hexane, $CH_2Cl_2$, EtOAc and $H_2O$. Repeated Sephadex LH-20 column chromatography on the EtOAc- and $H_2O-soluble$ fractions gave four compounds. Their structures were elucidated as quercetin (1), kaempferol (2), desmodin (3) and homoadonivernith (4) on the basis of spectroscopic evidences such as $^{1}H-NMR$, $^{13}C-NMR$, 2D-NMR and MS spectrum. Desmodin (3) and homoadonivernith (4) have not been reported from this plant so far.

• Archives of Pharmacal Research
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• v.27 no.4
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• pp.390-395
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• 2004

The methanol extract obtained from the aerial parts of Aceriphyllum rossii (Saxifragaceae) was fractionated into ethyl acetate (EtOAc), n-BuOH and $H_2O$ layers through solvent fractionation. Repeated silica gel column chromatography of EtOAc and n-BuOH layers afforded six flavonol glycosides. They were identified as kaempferol 3-O-$\beta$-D-glucopyranoside (astragalin, 1), quercetin 3-O-$\beta$-D-glucopyranoside (isoquercitrin, 2), kaempferol 3-O-$\alpha$-L-rhamnopyranosyl $(1{\to}6)-\beta$-D-glucopyranoside (3), quercetin 3-O$\alpha$-L-rharnnopyranosyl $(1{\to}6)-\beta$-D-qlucopyrano-side (rutin, 4), kaempferol 3-O-[$\alpha$-L-rharnnopyranosyl $(1{\to}4)-\alpha$-L-rhamnopyranosyl $(1{\to}6)-\beta$-D-glucopyranoside] (5) and quercetin 3-O-[$\alpha$-L-rhamnopyranosyl $(1{\to}4)\alpha$-L-rhamnopyranosyl $(1{\to}6)\beta$-D-glucopyranoside] (6) on the basis of several spectral data. The antioxidant activity of the six compounds was investigated using two free radicals such as the ABTS free radical and superoxide anion radical. Compound 1 exhibited the highest antioxidant activity in the ABTS $\{2,2-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid)\}$ radical scavenging method. 100 mg/L of compound 1 was equivalent to $72.1\pm1.4\;mg/L$ of vitamin C, and those of compounds 3 and 5 were equivalent to $62.7\pm0.5\;mg/L$ and $54.3\pm1.3\;mg/L$ of vitamin C, respectively. And in the superoxide anion radical scavenging method, compound 5 exhibited the highest activity with an $IC_{50}$ value of $17.6{\pm}0.3{\mu}M$. In addition, some physical and spectral data of the flavonoids were confirmed.

• Food Engineering Progress
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• v.13 no.2
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• pp.147-153
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• 2009

Quercetin is one of the main flavonoids from onion. To use quercetin as a functional component for onion food products, the effects of various extraction assisting methods such as juicing methods, microwave, ultrasound and enzyme treatments on the yield of quercetin and its glucosides were investigated. For conventional solvent extraction, the highest yield of quercetin and its glycosides was achieved with 0.8 mL/g of 60% methanol at 50$^{\circ}C$ for 15 min. The juicing methods using mixer and screw showed no influence on the yield. Microwave and ultrasound treatments showed 2.14 times and 2.06 times more quercetin yields than non-treated extraction, respectively. For cellulase and viscozyme treatments, the highest yields of quercetin were achieved with 0.5 mL/g of 1% enzyme-0.1M sodium acetate (pH 5.2) buffer solution. Cellulase and viscozyme treatment improved quercetin yield 1.65 times and 2.29 times more than non-treated one, respectively.

• Proceedings of the Korean Society of Postharvest Science and Technology of Agricultural Products Conference
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• 2003.04a
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• pp.22-39
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• 2003

Biological activity of phenolic compounds in seeds and leaves of safflower (Carthamu tinctorius L.) were evaluated using several in vitro and in vivo assays. Six phenolic constituents were isolated from the seeds and identified as N-feruloylserotonia, N- (p-coumaroyl)serotonin, matairesinol, 8′-hydroxyarctigenin, acacetin 7-O-$\beta$-D-glucoside (tilianine) and acacetin. Six phenolic compounds exhibited considerable antioxidative activity, and especially two serotonins showed potent DPPH radical scavenging activity and antiperoxidative activity against rat liver microsomal lipid peroxidation induced by the hydroxyl radical generated via a Fenton-type reaction. Additionally, six phenolic compounds possessed comparable cytotoxicity against three cancer cells, Hela cell, MCF-7 and HepG2 cell, and particularly acacetin and its glycosides had the most potent cytotoxicity. Moreover, we found that feeding safflower seeds attenuated bone loss, and lowered levels of plasma and liver lipids in ovariectomized rats. Serotonins, lignans and flavones stimulated proliferation of the osteoblast-like cells in a dose-dependent manner (10$^{-15}$ ~10$^{-6}$ M), as potently as E$_2$ (17$\beta$-estradiol). Particularly, serotonins were mainly responsible for bone-protecting and lipid lowering effects in ovariectomized rats. Meanwhile, eight flavonoids, including a novel quercetin-7-O-(6"-O-acetyl)-$\beta$-D-glucopyranoside and seven kown flavonoids, luteolin quercetin, luteolin 7-O-$\beta$-D-glucopyranoside, luteolin-7-O-(6"-O-acetyl)-$\beta$-D-gluco-pyranoside, quercetin 7-O- -glucopyranoside, acacetin 7-O-$\beta$-D-glucuronide and apigenin-6-C-$\beta$-D-glucopyranosyl-8-C-$\beta$-D-glucopyranoside were first isolated and identified from safflower leaf. Among these flavonoids, luteolin-acetyl-glucoside and $\beta$quercetin- acetyl-glucoside showed potent antioxidative activities against 2-deoxyribose degradation and lipid peroxidation in rat liver microsomes. Luteolin, quercetin and their corresponding glycosides also exhibited strong antioxidative activity, while acacetin glucuronide and apigenin-6, 8-di-C-glucoside were relatively less active. Finally, changes in phenolic compositions were also determined by HPLC in the safflower seed and leaf during growth stages and roasting process to produce standardized supplement powerds. These results suggest that phenolic compounds in the roasted safflower seed and leaf may be useful as potential sources of therapeutic agents against several pathological disorders such as carcinogenesis, atherosclerosis and osteoporosis.

• Natural Product Sciences
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• v.12 no.3
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• pp.122-124
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• 2006

Three flavonoid glycosides, $kaempferol-3-O-{\alpha}-L-rhamnopyranosyl-(1\;{\rightarrow}\;6)-{\beta}$-D-glucopyranoside$ or kaempferol-3-O-rutinoside (1), $isorhamnetic-3-O-{\alpha}-L-rhamnopyranosyl-(16)-{\beta}-D-glucopyranoside$ or isorhamnetin-3-O-rutinoside (2), and $quercetin-3-O-{\beta}-D-glucopyranosyl-(1 ${\rightarrow}\;2)-{\beta}-L-arabinopyranoside$ 3, the latter one being a new compound, were isolated from the methanolic extract of the aerial parts of Carrichtera annua. Mass spectrometry and 1D and 2D NMR spectroscopy allowed establishing the structure of these compounds.

• Korean Journal of Pharmacognosy
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• v.47 no.4
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• pp.295-300
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• 2016

Flavonoids are widely reported to be beneficial to human health. Among flavonoids, in general, flavonoid aglycons have better biological activities than flavonoid glycosides, in that aglycons can easily penetrate through cell membrane because of their low polarity. Therefore, kaempferol, quercetin and various their glycosides were evaluated for their abilities to inhibit NO and $PGE_2$ productions in LPS-induced RAW 264.7 cells. Of these flavonoids and flavonoid glycosides, kaempferol-7-O-${\beta}$-D-glucoside(kp-7-glu) which possesses a glycoside at C-7 position of the A ring in kaempferol, potently inhibited NO, $PGE_2$ and $TNF-{\alpha}$, $IL-1{\beta}$, IL-6 productions in LPS-induced RAW 264.7 macrophages.

• Preventive Nutrition and Food Science
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• v.8 no.4
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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.