• Bulletin of the Korean Chemical Society
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• v.28 no.5
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• pp.827-831
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• 2007

Bioassay-directed fractionation of Draba nemorosa led to the isolation of two new phenolic glycosides, 1-O- (sinapoyl)-glucitol (2) and 1,3-disinapoylgentiobiose (5) along with five known phenolic glycosides (1, 3, 4, 6, and 7). Their structures were characterized based on spectroscopic methods (2D NMR, HRTOFMS, IR, and UV). The isolated compounds showed antioxidant activities (IC50) in the range of 14-98 mM which were estimated by DPPH radical-scavenging assay.

• Bulletin of the Korean Chemical Society
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• v.32 no.3
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• pp.1027-1029
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• 2011

Two new phenolic glycosides were isolated from the rhizomes of Curculigo orchioides Gaertn.. Based on comprehensive spectroscopic analyses including IR, MS, 1D- and 2D NMR (COSY, HSQC, and HMBC), their structures were elucidated as 3-hydroxyl-5-methyphenol-1-O-[${\beta}$-D-glucopyranosyl-($1{\rightarrow}3$)-${\beta}$-D-glucopyranoside (1) and 1',3'-dimethoxyl-4-hydroxyalangifolioside (2).

• Preventive Nutrition and Food Science
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• v.15 no.1
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• pp.36-43
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• 2010

The purpose of this study was to investigate the phenolic acid, proanthocyanidin (PAs), and flavonol glycoside contents, as well as the antioxidant activities of pine needle extracts from six species of young pine trees. The extracts were prepared from Section Pinus (Diploxylon): P. densiflora, P. sylvestris, P. pinaster and P. pinea, and Section Strobus (Haploxylon): P. koraiensis and P. strobus. Phenolics were extracted from pine needles with 80% acetone to obtain the soluble free fraction, and insoluble residues were digested with 4 M NaOH to obtain bound ethyl acetate and bound water fractions. Phenolics were analyzed by HPLC, and the hydrophilic antioxidant activity was measured using oxygen radical absorbance capacity (ORAC). Total phenolic and flavonoid contents of the soluble free fraction were higher than those of the bound ethyl acetate and bound water fractions. The main phenolics were monomers and polymers of PAs in the soluble free fraction, and phenolic acids and flavonol glycosides in bound ethyl acetate fraction. Flavonol glycosides found in different species of pine needles were qualitatively similar within fractions, but composition varied among Pinus sections. High levels of kaempferol arabinoside and an unknown compound were present in all Strobus species. The soluble free fraction had the highest antioxidant activity, followed by bound ethyl acetate and bound water fractions.

• Natural Product Sciences
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• v.21 no.3
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• pp.162-169
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• 2015

Hamamelis japonica (Hamamelidaceae), widely known as Japanese witch hazel, is a deciduous flowering shrub that produces compact clumps of yellow or orange-red flowers with long and thin petals. As a part of our ongoing search for phenolic constituents from this plant, eleven phenolic constituents including six flavonol glycosides, a chalcone glycoside, two coumaroyl flavonol glycosides and two galloylated compounds were isolated from the flowers. Their structures were elucidated as methyl gallate (1), myricitrin (2), hyperoside (3), isoquercitrin (4), quercitrin (5), spiraeoside (6), kaempferol 4'-O-β-glucopyranoside (7), chalcononaringenin 2'-O-β-glucopyranoside (8), trans-tiliroside (9), cis-tiliroside (10), and pentagalloyl-O-β-D-glucose (11), respectively. These structures of the compounds were identified on the basis of spectroscopic studies including the on-line LCNMR-MS and conventional NMR techniques. Particularly, directly coupled LC-NMR-MS afforded sufficient structural information rapidly to identify three flavonol glycosides (2 - 4) with the same molecular weight in an extract of Hamamelis japonica flowers without laborious fractionation and purification step. Cytotoxic effects of all the isolated phenolic compounds were evaluated on HCT116 human colon cancer cells, and pentagalloyl-O-β-D-glucose (11) was found to be significantly potent in inhibiting cancer cell growth.

• 한국약용작물학회:학술대회논문집
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• 2011.09a
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• pp.332-333
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• 2011

• 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.

• Journal of Applied Biological Chemistry
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• v.51 no.2
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• pp.61-65
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• 2008

Three phenolic glycosides, gastrodin (1), parishin (2), and parishin B (3) were isolated from the n-BuOH fraction of Gastrodia elata (Orchidaseae) by medium pressure liquid chromatography. Their chemical structures were identified by the interpretation of their spectral data and direct comparison with literature values. Gastrodin and parishin were isolated as the major constituents in G. elata. Gastrodin may be a suitable index component for quality control of G. elata.

• Journal of the Korean Wood Science and Technology
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• v.35 no.5
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• pp.93-99
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• 2007

Paulownia coreana inner bark was collected, extracted in 70% acetone, concentrated under reduced pressure and sequentially fractionated using n-hexane, $CH_2Cl_2$, EtOAc and $H_2O$, then freeze dried to give brown powders. A portion of the EtOAc soluble powder was chromatographed on a Sephadex LH-20 column using a serious of aqueous methanol and ethanol-hexane mixture as eluting solvents. Two phenolic acid, $\rho$-courmaric acid and caffeic acid, two isomeric phenylethanoid glycosides, verbascoside and iso-verbascoside, and one epimeric phenylpropanoid glycoside, cistanoside F, were isolated and their structures were elucidated by spectroscopic analysis such as NMR and MS.

• Proceedings of the PSK Conference
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• 2003.04a
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• pp.256.2-256.1
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• 2003

Six known phenolic glycosides. hyperin(2), androsin(3), homoarbutin(4), isohomoarbutin(4a), pirolatin(7) and monotropein(6), together with two new compounds, (1)[mp. 215 - 217$^{\circ}C$, C$\sub$23/H$\sub$32/O$\sub$11/] and (5)[mp. 121 -123$^{\circ}C$, C$\sub$18/H$\sub$26/O$\sub$8/] were isolated from the BuOH fraction of Pyrola japonica(Pyrolaceae). The structures of the known compounds were determined by chemical and spectroscopic methods. (omitted)

• Natural Product Sciences
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• v.17 no.2
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• pp.65-79
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• 2011

Reactive oxygen species potentially cause damage to cellular components including lipids, protein and DNA; this oxidative damage plays a key role in the pathogenesis of neurodegenerative disease, cardiovascular disease, metabolic disease and cancer. On the basis of the oxidative stress hypothesis, a number of studies have been performed to search for an efficient and safe antioxidant. Although in vitro studies have provided promising results, only a limited number of natural and synthetic antioxidants have been developed for clinical application due to their low efficacy and side-effects. Thus, the discovery of new antioxidants with marked efficacy and safety has attracted worldwide attention in recent decades. Since plants are recognized as important sources of natural antioxidants, our research has focused on the discovery of new naturally occurring antioxidants from medicinal plants. The purpose of this review is to open a new prospect in the field of search for natural antioxidants from medicinal plants by summarizing our recent findings. Using in vitro bioassay systems such as 2,2-diphenyl-1-picrylhydrazyl, superoxide radical scavenging tests and lipid peroxidation models, we have tested over than 350 species of medicinal plants for their antioxidant activity and selected several of them for further investigation. During the research on the discovery of effective natural antioxidants from the medicinal plants selected, we have isolated several new and known antioxidant compounds that include stilbene glycosides, phenolic glycosides, flavonoids, oligostilbenes, and coumarins. Our results suggest that the presence of antioxidant compounds in the medicinal plants might be associated with the traditional use to treat inflammation, cardiovascular disease and various chronic diseases.