• Archives of Pharmacal Research
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• v.10 no.4
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• pp.260-261
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• 1987

The UV-pattern of several flavones, theier cytotoxicities against L1210 cell and their Inhibiting effects on ATPase from the cell seem to be correlated. 5.2'-Dihydroxy 6, 7, 8, 6'-tetramethoxyflavone ($ED_{50}$ = 2.3 ug/ml) and 5,2',6'-trihydroxy-6, 7, 8 trimethoxy flavone ($ED_{50}$ = 4.5 ug/ml), the most active flavones studied, have shown a narrow range of the absorbance ratio, Log $\varepsilon$ II/Log $\varepsilon$ I = 1.073 -1.109. They have inhibited the ATPase-activity to the greatest extent. These finding ssuggest that a certain angle between the flavone rings B and C plays an important role for the inhibition of the enzyme activity and thus the cytotoxicity.

• Bulletin of the Korean Chemical Society
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• v.28 no.10
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• pp.1827-1830
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• 2007

• Journal of Photoscience
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• v.8 no.3_4
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• pp.119-121
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• 2001

Three-Dimensional Quantitative Structure-Activity Relationship(QSAR) has been investigated over 67 flavonoids to correlate and predict GI$\sub$50/ values. The partial least-squares(PLS) model was performed to calculate the activity of each derivatives, and this was compared with the actual value. The results of the cross-validated(${\gamma}$$^2$=0.997) values show that cytotoxic activities play an important role which is in good agreement with the observed GI$\sub$50/ values.

• Bulletin of the Korean Chemical Society
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• v.28 no.8
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• pp.1261-1264
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• 2007

Bioassay-directed fractionations of the seed extracts of Trichosanthes kirilowii, have resulted in the isolation of two new compounds, 2-(4-hydroxy-3-methoxyphenyl)-3-(2-hydroxy-5-methoxyphenyl)-3-oxo-1-propanol (2) and isoetin 5'-methyl ether (5,7,2',4'-tetrahydroxy-5'-methoxyflavone) (3), together with two known compounds, 7-hydroxychromone (1) and 5,7,4'-trihydroxy-3',5'-dimethoxyflavone (tricin, 4). Their structures were characterized by spectroscopic analysis such as 2D-NMR, HRTOFMS, and UV. Compound 3 showed cytotoxicity against human lung cancer cell line A549, human skin melanoma SK-Mel-2, and mouse melanoma B16F1, with IC50 of 0.92, 8.0, and 7.23 μg/mL, respectively.

• Journal of Forest and Environmental Science
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• v.23 no.2
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• pp.87-91
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• 2007

The needles of L. kaempferi was extracted with 95% ethanol and successively partitioned with n-hexane, $CH_2Cl_2$ and EtOAc. Repeated column chromatography on the EtOAc and $H_2O$ soluble fractions gave three flavan-3-ols, one flavone glycoside, six flavonol glycosides and one lignan derivative. Their structures were elucidated on the basis of chemical and spectroscopic evidences. The antioxidant activities of the isolated compounds were evaluated by DPPH (1,1-diphenyl-2-picrylhydrazyl) radical scavenging method. Flavan compounds indicated good antioxidative potentials compared with BHT (butylated hydroxytoluene) and ${\alpha}$-tocopherol as controls. In the anti-inflammatory test on most of the isolated compounds, NO (nitric oxide) assay against the RAW 264.7 (Mouse Macrophage) showed similar inhibitory potentials to NO production of the control. The cytotoxicity was determined by MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) assay and most of the isolated compounds indicated no toxicity in various concentration.

• Korean Journal of Pharmacognosy
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• v.17 no.2
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• pp.168-177
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• 1986

Bioassay-directed isolation has yielded some cytotoxic substances against L1210 cell from the Korean traditional medicine. These include 5,2'-dihydroxy-6,7,8,6'-teramethoxyflavone $(IV,\;scutellaria\;root,\;ED_{50}\;=\;1.7\;{mu}g/ml)$, 7-geranyloxycoumarin $(XXXII,\;poncirus\;fruit,\;10.2\;{mu}g/ml) $and panaxydol $(I,\;white\;ginseng,\;0.03\;{mu}g/ml)$. IV, XXXII and their derivatives were synthesized in the purpose of in vivo tests and for observation of structure-activity relations. Among the flavone derivatives, 5,2',6'-trihydroxy-6,7,8-trimethoxy flavone (XVIII), 5-hydroxy-6,7,8-trimethoxy-6'-benzyloxyflavone (XVII) and 5,8-dihydroxy-6,7-dimethoxyflavone (X) showed the cytotoxicity which has no correlation to the flavone structures. Of the coumarins synthesized, 7,8-dihydroxycoumarin (XXVI), 6-7-dihydroxycoumarin (XXIX) and 6-hydroxy-5,7-dimethoxycoumarin (XXXI) showed considerable activities. Acetylated XXXI has moderate activity $(ED_{50}=17.2\;{mu}g/ml)$. Monobydroxycoumarins or their methyl and allyl ether were inactive. IV inhibits the growth of the solid form of S-180 by 70% at 40 mg/kg and shows T/C of 166% on the ascitic S-180 at 40 mg/kg. It strongly inhibits the activity of the membrane bounded ATPase from L1210 cell. The most cytotoxic fraction of the antitumor materials studied is the one from the trichosanthes root showing $ED_{50}=0. 0003\;{mu}g/ml$ against L1210 cell. This fraction, obtained from ethyl acetate extract, showed T/C of 130 and 135%, on ICR mice bearing S-180 and $BDF_1$ mice bearing L1210 at 10 mg/kg and 7.5 mg/kg, respectively.

• Natural Product Sciences
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• v.13 no.4
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• pp.300-303
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• 2007

Gossypin, a naturally occurring polyhydroxy flavonoid, when subjected to in vitro cytotoxic screening against vero cell lines exhibited 68.75% inhibition at a concentration of $1000{\mu}g$. When tested against five bacteria and five fungi, the flavone derivative showed a moderate activity against Staphylococcus aureus and Escherichia coli, mild inhibition against Pseudomonas aerugenosa and Salmonella typhi and no activity against any of the tested fungi, in the concentrations studied.

• Archives of Pharmacal Research
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• v.29 no.12
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• pp.1086-1090
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• 2006

The chromatographic separation of the MeOH extract from the twigs of Acer tegmentosum led to the isolation of ten phenolic compounds. The structures of these compounds were determined using spectroscopic methods as 3,7,3',4'-tetramethyl-quercetin (1), 5,3'-dihydroxy-3,7,4'-trimethoxy flavone (2), 2,6-dimethoxy-p-hydroquinone (3), (-)-catechin (4), morin-3-O-${\alpha}$-L-lyxoside (5), p-hydroxy phenylethyl-O-${\beta}$-D-glucopyranoside (6), 3,5-dimethoxy-4-hydroxy phenyl-1-O-${\beta}$-D-glucoside (7), fraxin (8), 3,5-dimethoxy-benzyl alcohol 4-O-${\beta}$-D-glucopyranoside (9) and 4-(2,3-dihydroxy propyl)-2,6-dimethoxy phenyl ${\beta}$-D-glucopyranoside (10). The compounds were examined for their cytotoxic activity against five cancer cell lines. Compound 3 exhibited good cytotoxic activity against five human cancer cell lines with $ED_{50}$ values ranging from $1.32\;to\;3.85\;{\mu}M$.

• Journal of Life Science
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• v.28 no.1
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• pp.43-49
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• 2018

Chrysoeriol is a widespread flavone, and it is usually found in alfalfa, which has been used as a traditional medicine to treat dyspepsia, asthma, and urinary system disorders. Recently, analysis has been conducted on the anti-inflammatory activity of chrysoeriol, but information on its antioxidative capacity is limited. In this study, the antioxidative potential of chrysoeriol against oxidative damage and its molecular mechanisms were evaluated by analysis of the cell viability, reactive oxygen species (ROS) formation, and Western blots in the RAW 264.7 cell line. Chrysoeriol significantly scavenged lipopolysaccharide (LPS)-induced intracellular ROS formation in a dose-dependent manner, without any cytotoxicity. Heme oxygenase-1 (HO-1), a phase II enzyme that exerts antioxidative activity, was also potently induced by chrysoeriol treatment, which corresponded to the translocation of nuclear factor-erythroid 2 p45-related factor 2 (Nrf2) into the nucleus. Moreover, mitogen-activated protein kinase (MAPK) and phosphoinositide 3-kinase (PI3K) were analyzed due to their important role in maintaining cellular redox homeostasis against oxidative stress. As a result, chrysoeriol-induced HO-1 upregulation was mediated by extracellular signal - regulated kinase (ERK), c-Jun $NH_2$-terminal kinase (JNK), and p38 phosphorylation. To identify the antioxidative potential exerted by HO-1, tert-butyl hydroperoxide (t-BHP)-induced oxidative damage was applied and mitigated by chrysoeriol treatment, which was confirmed by the HO-1 selective inhibitor and inducer, respectively. Consequently, chrysoeriol strongly strengthened the HO-1-mediated antioxidative potential through the regulation of the Nrf2/MAPK signaling pathways.

• Proceedings of the Plant Resources Society of Korea Conference
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• 2018.04a
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• pp.13-13
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• 2018

The anti-inflammatory (INF) compounds (1-15) were isolated from Agrimonia pilosa Ledeb. (APL) by activity-guided isolation technique. The isolated compounds (1-15) were identified as quercetin-7-O-rhanmoside (1), apigenin-7-O-glycoside (2), kaempferol-7-O-glycoside (3), apigenin-7-O-[6"-(butyl)-glycoside] (4), querceitn (5), kaempferol (6), apigenin (7), apigenin-7-O-[6"-(pentyl)-glycoside] (8), agrimonolide (9), agrimonolide-6-O-glucoside (10), desmethylagrimonolide (11), desmethylagrimonolide-6-O-glucoside (12), luteolin (13), vitexin (14) and isovitexin (15). Flavonoids, compound 2, 3, 11, and 14-15 have been found in APL for the first time. Furthermore, two novel flavone derivatives, compound 4 and 8, have been isolated inceptively in plant. In the no cytotoxicity concentration ranges of $0-20{\mu}M$, nitric oxide (NO) production level of 1-15 was estimated in LPS-treated Raw 264.7 macrophage cells. The flavone aglycones, 7 (apigenin, $IC_{50}=3.69{\pm}0.34{\mu}M$), 13 (luteolin, $IC_{50}=4.62{\pm}0.43{\mu}M$), 6 (kaempferol, $IC_{50}=14.43{\pm}0.23{\mu}M$) and 5 (quercetin, $IC_{50}=19.50{\pm}1.71{\mu}M$), exhibited excellent NO inhibitory (NOI) activity in dose-dependent manner. In the structure activity relationship (SAR) study of apigenin-derivatives (APD), apigenin; Api, apigenin-7-O-glucoside; Api-G, apignenin-7-O-[6"-(butyl)-glycoside]; Api-BG and apignenin-7-O-[6"-(pentyl)-glycoside]; Api-P, from APL on INF activity was investigated. The INF mediators level such as NO, INF-cytokines, NF-KB proteins, iNOS and COX-2 were sharply increased in Raw 264.7 cells by LPS. When pretreatment with APD in INF induced macrophages, NOI activity of Api was most effective than other APD with $IC_{50}$ values of $3.69{\pm}0.77{\mu}M$. And the NOI activity was declined in the following order: Api-BG ($IC_{50}=8.91{\pm}1.18{\mu}M$), Api-PG ($IC_{50}=13.52{\pm}0.85{\mu}M$) and API-G ($IC_{50}=17.30{\pm}0.66{\mu}M$). The NOI activity of two novel compounds, Api-PG and Api-BG were lower than their aglycone; Api, but more effective than Api-G (NOI: Api-PG and Api-BG). And their suppression ability on INF cytokines such as $TNF-{\alpha}$, $IL-1{\beta}$ and IL-6 mRNA showed the similar tendency. Therefore, the anti-INF mechanism study of Api-PG and Api-BG on nuclear factor-kappa B ($NF-{\kappa}B$) pathway, representative INF mechanism, was investigated and Api was used as positive control. Api-BF was more effectively prevent the than phosphorylation of $pI{\kappa}B$ kinase (p-IKK) and p65 than Api-PG in Raw 264.7 cells. In contrast, Api-PG and Api-BG were not reduced the phosphorylation of inhibitor of kappa B alpha ($I{\kappa}B{\alpha}$). Moreover, pretreatment with Api-PG and Api-BG, dose-dependently inhibited LPS-induced expression of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) mRNAs and proteins in macrophage cells, and their expression were correlated with their NOI activity. Therefore, APL can be utilized to health promote agent associated with their AIN metabolites.