• Proceedings of the Korean Society of Applied Pharmacology
• /
• 1994.04a
• /
• pp.245-245
• /
• 1994

From the active fraction, cytotoxic constituents 1-5 were isolated and identified to be 2(S)-5,7-dihydroxy-8,2'-dimethoxyflavanone (1), wogonin (5,7-dihydroxy-8-methoxyflavone, 2), 5,7-dihydruxy-8,2'-dimethoxyflavone (3), 2(5) -5,7,2'-trihydroxy-8-methoxyflavanone (4), 2(S) - 5,2',5'-trihydroxy-7,8-dimethoxyflavanone (5), respectively, with those of specimens$\^$1-2)/

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

• Korean Journal of Pharmacognosy
• /
• v.23 no.4
• /
• pp.234-239
• /
• 1992

Seven flavonoid components were isolated from fr. C of Scutellariae radix which showed antagonistic effects against bradykinin(BK). The results indicated that two oxygen functions (either -OH or $-OCH_3$) at 2'- and 6'-positions and/or an oxygen function at 6-position of flavone seemed to be favored for the BK inhibitory activities. Skullcapflavone-II(IV) which contains $6-OCH_3$, 2'-OH and $6-OCH_3$ in the structure was the most active among the flavones tested.

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

• Archives of Pharmacal Research
• /
• v.18 no.6
• /
• pp.440-448
• /
• 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%)

• Journal of Nutrition and Health
• /
• v.42 no.3
• /
• pp.278-290
• /
• 2009

This study aims to evaluate the changes of flavonoid contents and antioxidants activity of Jeju native citrus fruits juice according to the harvest date. Flavonoids such as quercatagetin, narirutin, hesperidin and neohesperidin were contained most plentifully in the juice of Jigak (Citrus aur-antium) by 573.73 mg/100 mL, Sadoogam (C. pseudogulgul) by 393.99 mg /100 mL, Soyooja by 29.63 mg/100 mL and Jigak (C. aurantium) by 201.23 mg/100 mL in the late August, respectively. The highest contents of nob-iletin, sinensetin and tangeretin among polymethoxyflavones were found in the juice of Hongkyool (C. tachibana) by 7.39 mg/100 mL, 2.24 mg/100 mL, 0.63 mg/100 mL in the late August, respectively. 3,5,6,7,8,3',4'- Heptamet- hoxyflavone recorded the highest amount in Punkyool (C. tangerina) by 0.27 mg/100 mL in the late August, but the other polymethoxyflavones including 3',4',7,8-tetramethoxyflavone, 3',4'-dimethoxyflavone, 4'-methoxyflavone, 5,6,7,3',4',5'-hexamethoxyflavone, scutellarein tetramethylether were observed only trace amount in all the citrus fruits. Flavonoid contents in the citrus fruit juices were the highest during early maturation and decreased rapidly while ripening. Total polyphenol contents were the highest in the late August and decreased with ripening. However from the late December, the contents were increased again. Antioxidant activities of the fruits were evaluated as electron donating ability and were the lowest in the late September and increased with the fruit ripening. These results suggest that quercetagetin among all the flavonoids was most plentiful in Jigak and Dangyooja (C. grandis), so that the fruits could be used for industrial material of flavonoids and antioxidant agents.