• 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.

• Natural Product Sciences
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• v.27 no.4
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• pp.284-292
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• 2021

Recently, a phytoestrogenic functional food has been developed using the fruits of Sophora japonica. Phytochemical investigation of fruits of S. japonica led to the isolation of eight flavonoid glycosides using various chromatographic techniques. The isolated compounds were identified as genistin (1), sophoricoside (2), genistein 7,4'-di-O-β-D-glucopyransoide (3), sophorabioside (4), genistein-7-O-β-D-glucopyranoside-4'-O-[(α-L-rhamnopyranosyl)-(1→2)-β-D-glucopyranoside] (5), sophoraflavonoloside (6), nicotiflorin (7) and kaempferol-3-O-α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranosyl-(1→3)-β-D-glucopyranoside (8), respectively, by comparison of their spectroscopic data with those reported in the literature. In addition, a new HPLC-DAD method for simultaneous determination of the isolated compounds was developed to quantitate the contents of flavonoids in S. japonica and S. flavescens. The method was validated in terms of limit of detection, limit of quantitation, specificity, linearity, precision and accuracy. The validated method was successfully applied to determine eight flavonoids in two Sophora species. The contents of eight flavonoids varied according to the parts and species. Particularly, it was found that only the fruits of S. japonica contained sophoricoside, a phytoestrogenic isoflavone.

• Journal of Applied Biological Chemistry
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• v.50 no.3
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• pp.175-178
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• 2007

• KSBB Journal
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• v.13 no.3
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• pp.251-258
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• 1998

A structured kinetic model is proposed to describe cell growth and secondary metabolite, flavone glycosides, synthesis in batch suspension culture of Scutellaria baicalensis G. The model has been developed by representing the physiological state of cell described as the activity and viability which can be estimated based on the culture fluorescence. In the model, three type of cells are considered; active-viable, nonactive-viable and dead cells. Viable cell weight could be determined based on the relative fluorescence intensity. The flavone glycosides could be produced by both active-viable and non-active viable cells with a different production rate. And the model includes the cell expansion due to glucose concentration and death phase which accounts for the release of intracellular secondary metabolite into medium. Dependent variables include substrate concentration(glucose), cell mass(dry cell weight and fresh cell weight), product concentration(flavone glycosides), activity and viability. Satisfactory agreement between the model and experimental data is obtained from shake flask culture of Scutellaria baicalensis G. The proposed model can predict the cell growth and flavone glycosides synthesis as well as intermediate materials.

• 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.

• YAKHAK HOEJI
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• v.40 no.3
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• pp.335-339
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• 1996

Optimal medium for growth and glycosidases production of Bacteroides JY-6, an human intestinal bacterium, was general anaerobic medium or tryptic soy broth containing sod ium thioglycolate and ascorbic acid. By cocultivation of Staphylococcus R-48, Bacteroides JY-6 could be cultured in LB broth unable to culture JY-6. Heated Staphylococcus R-48 was also the inducer of the production of Bacteroides JY-6 glycosidases. These glycosidases were induced well by natural flavonoid glycosides, such as poncirin, naringin and rutin, but were not by synthetic substrates, p-nitrophenyl ${\beta$-D-glucopyranoside and p-nitrophenyl ${\alpha}$-L-rhanmopyranoside.

• Korean Journal of Pharmacognosy
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• v.23 no.4
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• pp.201-210
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• 1992

Scutellariae plants contain a large number of flavonoids and in addition, many of them are with unusual A- and/or B-ring substitutions. The total number of flavonoids reported up to the middle of 1991 are 137 including 89 of flavones, flavonols and their glycosides including 3 C-glycosides$(1{\sim}89)$, 39 of flavanones, dihydroflavonols and their glycosides $(90{\sim}128)$, 8 of chalcones $(129{\sim}136)$ and one biflavonoid, 8, 8'-bibaicalein(137). More than half of the flavonoids are with either unusual 5-metboxy(2'-methoxy in case of chalcones) in A-ring and/or 2'-oxygenation(2-oxygenation in case of chalcones) in B-ring substitutions. Four flavones, four flavanones and two chalcones are with methylation at 5-OH(2'-OH in case of chalcones) and six of them also have 2'-oxygenations(2- in case of chalcones). Sixtyeight out of total 137 flavonoids have oxygenated substitution at 2'-(2- in case of chalcones) position of B-ring and in addition, 27 of them have another oxygen function at 6'-(6- in case of chalcones) and 18 of them have additional oxygen substitutions either at 3'-, 5'-,3',6'-or 3', 4', 5'-(3, 4, 5- in case of chalcones) positions. The distribution and isolation of flavonoid components of Scutellariae plants are tabulated with references.

• Natural Product Sciences
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• v.8 no.2
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• pp.35-43
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• 2002

Glycosides of herbal medicines, such as glycyrrhizin, ginsenosides, kalopanaxsaponins, rutin and ponicirin, were studied regarding their metabolic fates and pharmacological actions in relation to intestinal bacteria using germ-free, gnotobiotic and conventional animals. When glycyrrhizin (GL) was orally administered, $18{\beta}-glycyrrhetinic\;acid\;(GA)$, not GL, was detected in plasma and intestinal contents of gnotobiotic and conventional rats. However, GA could not be detected in germ-free rats. When GL was incubated with human intestinal bacteria, it was directly metabolized to GA (>95%) or via $18{\beta}-glycyrrhetinic\;acid-3-{\beta}-D-glucuronide$(>5%). Orally administered GL was effective in gnotobiotic and conventional rats for liver injury induced by carbon tetrachloride, but was not effective in germ-free rats. When ginseng saponins were orally administered to human beings, compound K in the plasma was detected, but the other protopanxadiol saponins were not detected. The compound K was active for tumor metastasis and allergy. When kalopanaxsaponins were incubated with human intestinal microflora, they were metabolized to kalopanaxsaponin A, kalopanaxsaponin I and hederagenin. These metabolites were active for rheumatoid arthritis and diabetic mellitus while the other kalopanxsaponins were not. When flavonoid glycosides were orally administered to animals, aglycones and/or phenolic acids were detected in the urine. The metabolic pathways proceeded by intestinal bacteria rather than by liver or blood enzymes. These metabolites, aglycones and phenolic acids, showed antitumor, antiinflammatory and antiplatelet aggregation activities. These findings suggest that glycosides of herbal medicines are prodrugs.

• 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.

• Natural Product Sciences
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• v.24 no.4
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• pp.259-265
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• 2018

The three flavone glycosides, 4'-O-methylisoscutellarein 7-O-(6'''-O-acetyl)-${\beta}$-D-allopyranosyl(1${\rightarrow}$2)-${\beta}$-D-glucopyranoside (1), isoscutellarein 7-O-(6'''-O-acetyl)-${\beta}$-D-allopyranosyl(1${\rightarrow}$2)-${\beta}$-D-glucopyranoside (3), and isoscutellarein 7-O-${\beta}$-D-allopyranosyl(1${\rightarrow}$2)-${\beta}$-D-glucopyranoside (4) in addition to a flavonol glycoside, kaempferol 3-O-${\beta}$-D-glucopyranoside (astragalin, 2), were isolated from Stachys japonica (Lamiaceae). In cholinesterase inhibition assay, compound 1 significantly inhibited aceylcholinesterase (AChE) and butyrylcholinesterase (BChE) activities ($IC_{50}s$, $39.94{\mu}g/ml$ for AChE and $86.98{\mu}g/ml$ for BChE). The content of isolated compounds were evaluated in this plant extract by HPLC analysis. Our experimental results suggest that the flavonoid glycosides of S. japonica could prevent the memory impairment of Alzheimer's disease.