• Applied Biological Chemistry
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• v.42 no.2
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• pp.162-165
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• 1999

Effects of compounds isolated from Ainsliaea acerifolia on alcohol metabolism in rats were examined and the results were as follows: Apigenin $7-O-{\beta}-D-glucoside$, after a single oral administration to rats, was found to cause a significant decrease in the serum ethanol concentration as well as enhancement of liver cytosolic alcohol dehydrogenase(ADH) activity.

• Archives of Pharmacal Research
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• v.25 no.3
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• pp.313-319
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• 2002

A total of eight flavonoids (1-8), including a novel $quercetin-7-o-(6"-o-acetyl)-{\beta}-D-glucopyranoside$ (6) and seven known flavonoids, luteolin (1), quercetin (2), luteolin $7-o-{\beta}-D-glucopyranoside$ (3), $luteolin-7-o-(6"-Ο-acetyl)-{\beta}-D-glucopyranoside$ (4) quercetin $7-o-{\beta}-D-glucopyranoside$ (5), acacetin 7-o-{\beta}-D-glucuronide (7) and apigenin-6-C-{\beta}-D-glucopyrano $syl-8-C-{\beta}-D-glucopyranoside$ (8), have been isolated from the leaves of the safflower (Carthamus tinctorius L.) and identified on the basis of spectroscopic and chemical studies. The antioxidative activity of these flavonoids was evaluated against 2-deoxyribose degradation and rat liver microsomal lipid peroxidation induced by hydroxyl radicals generated via a Fenton-type reaction. Among these flavonoids, luteolin-acetyl-glucoside (4) and quercetin-acetyl-glucoside (6) showed potent antioxidative activities against 2-deoxyribose degradation and lipid peroxidation in rat liver microsomes. Luteolin (1), quercetin (2), and their corresponding glycosides (3 & 5) also exhibited strong antioxidative activity, while acacetin glucuronide (7) and apigenin-6,8-di-C-glucoside (8) were relatively less active.

• Natural Product Sciences
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• v.26 no.4
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• pp.289-294
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• 2020

Eclipta prostrata is an annual herb, belonging to Asteraceae family, and has been traditionally used to improve immunity and treat hepatitis and bacterial disease in Korea. In this study, a new coumestan glucoside (1) along with ten known compounds (2 - 11) was isolated from E. prostrata. The chemical structures of isolates were elucidated to be wedelolactone-9-O-β-D-glucopyranoside (1), wedelolactone (2), demethylwedelolactone (3), apigenin (4), apigenin-7-sulfate (5), luteolin (6), luteolin-7-sulfate (7), luteolin-7-O-β-D-glucopyranoside (8), pratensein-7-O-β-D-glucopyranoside (9), 3,4-di-O-caffeoylquinic acid (10) and 3,5-di-O-caffeoylquinic acid (11) based on the spectroscopic evidence.

• Journal of Applied Biological Chemistry
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• v.59 no.4
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• pp.357-360
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• 2016

Chrysanthemum morifolium flowers were extracted with 80 % aqueous MeOH, and the concentrated extract was partitioned into EtOAc, n-butyl alcohol (n-BuOH), and water fractions. The repeated silica gel and octadecyl silica gel column chromatographies for the EtOAc and n-BuOH fractions led to isolation of four flavonoids. The chemical structures of the compounds were determined as acacetin (1), apigenin (2), apigenin-7-O-${\beta}$-$\small{D}$-glucopyanoside (3), acacetin-7-O-${\beta}$-$\small{D}$-glucopyranoside (4) based on spectroscopic data analyses including nuclear magnetic resonance, mass spectrometry, and infrared spectrometry.

• 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.

• Applied Biological Chemistry
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• v.51 no.4
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• pp.305-308
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• 2008

Seven compounds (1-7) were isolated from n-hexane and EtOAc-soluble fractions of the roots of Erigeron annuus by repeated silica gel column chromatography. They were identified as simiarenol (1), ${\beta}$-sitosterol (2), daidzein (3), apigenin (4), apigenin 7-O-${\beta}$-D-glucuronide (5), 3-hydroxy-pyran- 4-one (6), and ${\beta}$-sitosterol glucoside (7) on the basis of physical and spectroscopic data. Compounds 1 and 3 were isolated for the first time from the Erigeron species.

• Natural Product Sciences
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• v.7 no.2
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• pp.49-52
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• 2001

Anti-lipid peroxidative activity and phytochemical study on the leaves of Glycine max Meer. were investigated. The methanol extract of the leaves of G. max reduced the level of lipid peroxides induced by bromobenzene in vitro. From the leaves of this plant, apigenin, genistein $7-O-{\beta}-D-glucopyranoside$, kaempferol $3-O-{\beta}-D-glucopyranoside$, and kaempferol 3-O-sophoroside were isolated and characterized by spectral data.

• Archives of Pharmacal Research
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• v.27 no.2
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• pp.177-183
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• 2004

In order to develop new anti-photoaging agents, we examined the antioxidative activity and the inhibition effect of matrix metalloproteinase-1 (MMP-1) on the extracts of a marine product, Zostera marina L., which is known for its potent activity. Three compounds (compounds 1, 2, and 3) were isolated from an ethyl acetate (EtOAc) soluble fraction of the product; they were identified as apigenin-7 -O-$\beta$-D-glucoside (1), chrysoeriol (2), and luteolin (3). These compounds were found to scavenge radicals and reactive oxygen species (ROS) and were measured to have $SC_{50}$/ values of 0.18 mM, 0.68 mM, and 0.01 mM against the 1, 1-diphenyl-2-picrylhydrazyl (DPPH) radical and 0.04 mM, 0.03 mM, and 0.01 mM against the superoxide radical in the xanthine/xanthine oxidase system, respectively. Compound 3 suppressed the expression of MMP-1 by up to 44％ at 4.0 $\mu$M and inhibited the production of interleukin 6 (IL-6), which is known as a cytokine that induces MMP-1 expression. From these results, compound 3 and the other compounds were determined to have antioxidative activity and to inhibit MMP-1 expression. Thus, the three compounds are expected to be useful for preventing the photoaging of skin.

• Journal of Applied Biological Chemistry
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• v.51 no.2
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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.

• Natural Product Sciences
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• v.14 no.2
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• pp.100-106
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• 2008

Column chromatographic separation of the MeOH extract from the aerial parts of Schizonepeta tenuifolia Briquet led to the isolation of twelve terpenes (1 - 11 and 17), four phenolics (13 - 16) and a hexenyl glucoside (12). Their structures were determined by spectroscopic means to be (-)-pulegone (1), piperitenone (2), p-cymene-3,8-diol (3), schizonepetoside A (4), schizonepetoside C (5), (+)-spatulenol (6), ursolic acid (7), $2{\alpha}$,$3{\alpha}$,$24{\alpha}$,-trihydroxyolean-12en-28oic acid (8), $5{\alpha}$,$8{\alpha}$-epidioxyergosta-6,22-diol-$3{\beta}$-ol (9), stigmast-4-en-3-one (10), ${\beta}-sitosterol$ (11), (Z)-3-hexenyl-1-O-${\beta}$-D-glucopyranoside (12), rosmarinic acid (13), apigenin-7-O-${\beta}$-D-glucopyranoside (14), luteolin-7-O-${\beta}$-D-glucuronopyranoside (15), hesperidin (16) and trans-phytol (17). Compounds 2, 3, 8, 9 and 12 were for the first time isolated from S. tenuifolia Briq.