• Archives of Pharmacal Research
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• v.18 no.6
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• pp.440-448
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• 1995

Fitty two flavones were synthesized from polyoxygenated dibenzoylmethanes which were obtained by a modified Baker-Venkatarman rearrangement, of 2-benzoyl oxyacetophenones. The following flavones among them showed good cytotoxic activities against L1210 and HL60 cells ; 2'-benzoyloxy-5,7-dimethoxyflavone $(8.2{\mu}g/ml,{\;}5.0 {\mu}g/ml)$, 2'-benzyloxy-5,7,8-trimethoxyflavone $(5,9 {\mu}g/ml,{\;}11.0{\mu}g/ml,{\;}2.7{\mu}g/ml)$, 2'-hydroxy-5,7,8-trimethoxyflavone $(9.8{\mu}/ml,{\;}6.2{\mu}g/ml)$, 2'-benzyloxy-5-hydroxyflavone $(5.2 {\mu}g/ml,{\;}3.6{\mu}g/ml)$, and 5,2'-dihydroxyflavone $(5.1{\mu}g/ml,{\;}4.0{\mu}g/ml)$. Presence of 5-methoxy group potentiated the cytotoxic activity, while the existence of 7-methoxy group decreased the activity. 5-Hydroxy or methoxy activates 4-carbonyl group, while 7-methoxy group deactivates the acrbonyl group. From these observation it was concluded that the activation of carbonyl group at C-4 of a flavone is important for the enahncement of the cytotoxic activity. The presence of both 5-hydroxy and 2-benzyloxy-or 2-hydroxy group enhanced the antitumor activity; 2'-benzyloxy-5-hydroxy-7-methoxyflaone 9T/C=144%), 5.2'-dihydroxy-7-methoxyflavone (T/C=132%) and 5,2'-dihydroxy-6,78,6' trtramethoxyflvone (T/C = 172%) 2'hexanolytion of 5,2'-dihydroxy-flavones did not improve the natitumor activity; 2' hexanoyloxy-5-hydroxy-7-methoxyflavone showed T/C = 132%, about the same as that of 5,2'-dihydroxy-7-methoxyflvone (T/C=130%)

• Proceedings of the PSK Conference
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• 2003.04a
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• pp.235.2-235.2
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• 2003

To decipher the structure-activity relationships of flavones for the inhibition of cyclooxygenase-2 catalyzed prostaglandin production, we synthesized 7-methxoyflavones, 7-hydroxyflavones, 5-methxoyflavones, 5-hydroxyflavones and flavones without any phenol group on A ring. Methoxyflavones were prepared from 2.6- and 2,4-dihydroxyacetophenones in 3 steps. Most of the methxoyflavones were converted to the corresponding hydroxyflavones by the reaction with BBr3 in good yields. (omitted)

• Journal of Microbiology and Biotechnology
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• v.19 no.4
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• pp.387-390
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• 2009

Microbial UDP-glycosyltransferases can convert many small lipophilic compounds into glycons using uridine-diphosphate-activated sugars. The glycosylation of flavonoids affects solubility, stability, and bioavailability. The gene encoding the UDP-glycosyltransferase from Bacillus cereus, BcGT-3, was cloned by PCR and sequenced. BcGT-3 was expressed in Escherichia coli BL21(DE3) with a glutathione S-transferase tag and purified using a glutathione S-transferase affinity column. BcGT-3 was tested for activity on several substrates including genistein, kaempferol, luteolin, naringenin, and quercetin. Flavonols were the best substrates for BcGT-3. The enzyme dominantly glycosylated the 3-hydroxyl group, but the 7-hydroxyl group was glycosylated when the 3-hydroxyl group was not available. The kaempferol reaction products were identified as kaempferol-3-O-glucoside and kaempferol-3,7-O-diglucoside. Kaempferol was the most effective substrate tested. Based on HPLC, LC/MS, and NMR analyses of the reaction products, we conclude that BcGT-3 can be used for the synthesis of kaempferol 3,7-O-diglucose.

• Journal of the Korean Applied Science and Technology
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• v.19 no.3
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• pp.167-173
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• 2002

The isoflavone as a derivatives of flavone is colorless crystalline compounds. It acts on synthesis of fibronectine, collagen III, collagen I in human normal fibroblast by same biological activity to animal hormone. In this study, we tried to search and demonstrate system content rate of dermal translocation system for cosmetics using microemulsion containing isoflavone. The results of microemulsion stability test by centrifugation, storage in incubator and circulation chamber showed that separation of phase did not appear after 30 days. By the skin flexibility test, it has confirmed efficiency and effect as cosmetics materials. As the result, the microemulsion showed that skin flexibility factor improved up to 7.6%. We could confirm that O/W type microemulsion was stable system.

• Korean Journal of Food Science and Technology
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• v.38 no.2
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• pp.279-283
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• 2006

This study was conducted to examine the effect of polyphenols from safflower seed on HMG-CoA reductase (HMGR) activity, LDL oxidation and Apo A1 secretion from Hep3B cell. The safflower seed polyphenols were matairesinol (Iignan), enterolactone (lignan metabolite), acacetin (flavone) and serotonin derivative. In addition to safflower polyphenols, mevastatin, ${\alpha}-estradiol,\;{\alpha}-tocopherol$ and soy genistein were tested as reference compounds depending on the type of the test. HMGR source was liver microsome obtained from rat fed 2% cholestyramine for 10 days. Inhibition of HMGR activity was greater with mevastatin (53%) than safflower serotonin derivatives (45%), followed by genistein (35%), but was very small with matairesinol, enterolactone and acacetin. LDL oxidation induced by $CuSO_4$ was suppressed by all the test material used in the present study and in the order of safflower serotonin derivatives> matairesinol > ${\beta}-estradiol$ > genistein > acacetin > enterolactone. Apo A1 secretion from Hep3B cell was significantly stimulated by mevastatin, but moderately (p<0.1) by ${\beta}-estradiol$ and genistein as well as enterolactone. These results suggest that the safflower polyphenols improve body lipid status via inhibition of cholesterol synthesis and suppression of LDL oxidation.