• Archives of Pharmacal Research
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• v.19 no.6
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• pp.543-550
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• 1996

Analogues of $2(S)-5, 2^{l}, 5^{l}$-trihydroxy-7, 8-dimethoxyflavanone, a naturally-occurring compound, which had been reported to have potent antitumor activity, were synthesized and examined for the cytotoxicity against three cancer cell lines. Among the intermediate chalcones and synthetic 5-hydroxy-7, 8-dimethoxyflavanone analogues, $({\pm})2^{l}, 5^{l}-dibenzyloxy-5, 7, 8-trimethoxyflavanone$ exhibited about 2-8 times stronger activity than $2(S)-5, 2^{l}, 5^{l}$-trihydroxy-7, 8-dimethoxyflavanone against L1210, K562 and A549 cancer cell lines. In the structure-activity relationship, it is suggested that among analogues of 5-hydroxy-7, 8-dimethoxyflavanone, the existence of two oxygenated groups of para-relation at $C-2^{I} and C-5^{I}$ positions on flavanone B-ring, may be necessary to exhibit effective cytotoxic activity.

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

• Journal of the Korean Society of Food Science and Nutrition
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• v.20 no.4
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• pp.369-375
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• 1991

Carotenoid pigments from muscle of mussel, Mytilus coruscus, and blue mussel edulis, were separated by thin layer and column chromatography. The isolated carotenoids were identified by comparative test with reference carotenoids, reduction with sodium borohydride, isomerization with iodine and absorption spectrophotometry. The carotenoid content in the muscle of mussel were 0.4mg% in male and 2.7mg% in female, and the carotenoids were composed of 23.4%, 33.4% mytiloxanthin, 26.3%, 22.5% 3, 4, 3'-trihydroxy-7', $8'-didehydro-{\beta}-carotene$, 24.8%, 22.8% pectenoxanthin, 14.0%, 9.9% pectenolone and 5.1%, 6.1% diatoxanthin in male and female, respectively. While, the carotenoid contents in the muscle of blue mussel were 1.1mg% in male and 3.2mg% in female, and the carotenoids were composed of 33.8%, 35.6% mytiloxanthin, 28.4%, 44.7% pectenoxanthin, 18.1%, 5.0% diatoxanthin, 9.7%, 8.7% pectenolone and 5.5%, 3.1%, 3, 4, 3'-trihydroxy-7', $8'-didehydro-{\beta}-carotene$ in male and female, respectively.

• Archives of Pharmacal Research
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• v.20 no.4
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• pp.368-371
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• 1997

In an effort to increase of the antitumor activity of 2(S)-$2^{I}$,$5^{I}$-trihydroxy-7, 8-dimethoxyflavanone isolated from Scutellaria indica, we synthesized its analogues, II, III and IV. They showed potent cytotoxicity in vitro against cancer cell lines, L1210, K562 and A549. On the basis of $ED_50$ values against the cancer cell lines, III exhibited about 2-7 times stronger activity than I against various cell lines. We tested the antitumor activity of the analogues against Sarcoma 180 cells in vivo and evaluated the structure-activity relationship. The antitumor activity appeared to be related to the hydrogen bond between carbonyl group at C-4 and hydroxyl group at C-5, in contrast to cytotoxic action.

• Bulletin of the Korean Chemical Society
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• v.27 no.7
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• pp.995-1000
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• 2006

Three new compounds orizaanthracenol (1-methoxyanthracen-2-ol, 1), 1-hydroxy-7-((2S,3R,4R,5S)-2'',3'',4''-trihydroxy-5''-(hydroxymethyl)tetrahydro-2H-pyran-1-yloxy)anthracen- 2-yl 3',7'-dimethyloctanoate (2) and 1-hydroxy-7-((2S,3R,4R,5S)-2'',3'',4''-trihydroxy-5''-(hydroxymethyl)tetrahydro-2H-pyran-1-yloxy)anthracen- 2-yl 3',7',11',15',19'-pentamethyltricosanoate (3) have been isolated and determined from the rice hulls of Oryza sativa. The structures of the compounds were elucidated using 1D and 2D NMR spectral methods, viz: 1H-NMR, 13C-NMR, DEPT, COSY and HSQC, and HMBC aided by IR, EIMS and FAB-MS. These isolated compounds were tested in bioassay on germination of radish to detect their inhibitory activities, in which compound 1 exhibited the most inhibition at the concentration of 40 ppm was 50.96% of total dry weight. Furthermore, germination and growth of radish were reduced by 27 to 48%, and dry weight of shoot and root were arranged from 50 to 52%, whilst compounds 2 and 3 exhibited weak inhibition than 1.

• Natural Product Sciences
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• v.12 no.4
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• pp.205-209
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• 2006

The structures of flavonoids, 2(S)-5,7-dihydroxy-8,2'-dimethoxyflavanone (1), wogonin (2), 2(S)-5,7, 2'-trihydroxy-8-methoxyflavanone (3), and 2(S)-5,2',5'-trihydroxy-7,8-dimethoxyflavanone (4), isolated from Scutellaria indica were revised on the basis of 2D NMR spectroscopy, including to gCOSY, gHSQC, and gHMBC. Compounds 1-4 were tested in vitro protein tyrosine phosphatase 1B (PTP1B) inhibitory activity. Compounds 2 and 4 exhibited weak PTP1B inhibitory activity with $IC_{50}$ values of 208 and $337{\mu}M$, respectively.

• Journal of the Society of Cosmetic Scientists of Korea
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• v.43 no.1
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• pp.11-18
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• 2017

An anti-aging compound ethyl (4-(2,3-dihydro-1H-indene-5-carboxyamido) benzoate) rapidly crystallizes in emulsion systems, and a flavonoid 3,5,7-trihydroxy-4'-methoxy-8-prenylflavone bearing a whitening function causes coloration of cosmetic compounds when mixed with metal oxides. In this study, an electrospray method was used to encapsulate water-insoluble bioactive compounds in polymeric microparticles. Poly (methyl methacrylate) and polycaprolactone were used to encapsulate ethyl (4-(2,3-dihydro-1H-indene-5-carboxyamido) benzoate) and 3,5,7-trihydroxy-4'-methoxy-8-prenylflavone, respectively. It was found that polymer concentration, the structure of electrospray nozzle, and compatibility between polymers and bioactive compounds were important factors in the preparation of the particles. Polycaprolactone particles encapsulating 3,5,7-trihydroxy-4'-methoxy-8-prenylflavone was effective in preventing coloration of a cosmetic compound when mixed with metal oxides.

• Preventive Nutrition and Food Science
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• v.3 no.4
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• pp.315-319
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• 1998

Previously, the methanolic extract of Paeonia moutan seeds was found to potently inhibit soybean lipoxy-genase (SLO). Hence to isolate SLO inhibitor, the defattd methaniolic extract of the seeds was consecutively partitioned wiht ether, ethyl acetate,n-butanol ,adn water. The ether souble fraction showing strong inhibitory activity against SLO was further fractionated into a strongly acidic, a weakly acidic, and a neutral fractions. The strongly acidic components of the ether extract were successively subjected to chromatography on a silica gel, Sephadex LH-20, and preparative HPLC. Four phenolic compounds were isolated , and twio of them showing a strong SLO inhibition activity were identified as luteolin (IC50=2.32$\mu\textrm{g}$/ml) and 5,6,4'-trihydroxy-7,3'- dimethoxylflavone (IC50=0.31$\mu\textrm{g}$/ml) by UV, IR, 1H-& 13C-NMR, and MS spectroscopy. In addition, two flavonoids showed significantly antioxidative activity as strong as that of of $\alpha$-tocopherol (p<0.05) in the autoxidation system of linoleic acid. These results suggest that luteolin and 5,6,4'-trihydroxy-7,3'-dimethoxy-flavone may be used as a potential source of anti-inflammatory agents with antioxidative activity.

• Korean Journal of Plant Tissue Culture
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• v.24 no.3
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• pp.149-152
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• 1997

To search for a compound inhibiting the petunia callus growth from Streptomyces sp., we investigated the activity in the culture broth of 400 strains. The active compound was successively purified with solvent fractionation, silica gel column chromatography from Streptomyces sp. 9602 strain, and identified as 2, 5, 7-trihydroxy-3-(5'-hydroxyhexyl)-1, 4-naphthoquinone by 1H-NMR, EI-MS, IR and UV. It inhibited the callus growth of petunia by 50% at $32\mu\textrm{g}$/mL.

• Korean Journal of Medicinal Crop Science
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• v.14 no.4
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• pp.212-216
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• 2006

Root of Scutellaria baicalensis G. was extracted with methanol and water to give the yield of 30.0% in order to find the antioxidant substance. The extract was fractionated with diethyl ether, n-butanol and water to test the inhibitive activity against xanthine oxidase. Three fractions inhibited the activities of xanthine oxidase by 48.2%, 10.2% and 2.8%, respectively, at the amount of $0.1\;{\mu}g$. A component that exhibited strong inhibition of xanthine oxidase was isolated from diethyl ether fraction (SE Fr.) by silica gel column chromatography and HPLC, and then identified by $^1H-NMR$, $^{13}C-NMR$ and MS spectrophotometry. EDA (Electron Donating ability) of the compound was 28.5% at the concentration $100\;{\mu}g/3\;ml$. That was identified to be 3,5,7-trihydroxy-2'-methoxyflavanone by spectrophotometric analysis using $^1H-NMR,\;^{13}C-NMR$ and Mass spectrophotometry.