• 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.

• 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.

• 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.

• Journal of the Korean Chemical Society
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• v.32 no.6
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• pp.575-580
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• 1988

$({\pm})-{\gamma}$-Rhodomycinone(4) and 10-Deoxy-${\gamma}$-rhodomycinone(5), late-stage Precursors of the alglycone of antitumor antibiotic Rhodomycin(2) were prepared from the cleavage of epoxide ring of 9-ethyl-9,10-epoxy-4,6, 11-trihydroxy-7,8,9,10-tetrahydronaphthacene-5,12-dione(10). The epoxide 10 was furnished from 9-acetyl-4,5,6,11,12-pentamethoxy-7,8-dihydronaphthacene(6), which was assembled utilizing ring annelation methodology developed by Hauser-Rhee.

• Journal of the Korean Wood Science and Technology
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• v.34 no.2
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• pp.88-94
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• 2006

The purpose of this study is to examine the relationship between antioxidant activities and chemical structures of various chalcones. Twenty-two chalcones were assessed for their radical scavenging activity using the 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay. Of 22 compounds tested, the most active on DPPH radical was 2',4-dihydroxy-3,3'5-trimethoxy-5'-propylchacone (4) (72.6% at 100 ppm). It was followed by 3',4'-dihydroxy-3,4,5-trimethoxy-6'-methylchalcone (6), 2',4,4'-trihydroxy-3-methoxy-5-propenylchalcone (7) and 2',4,4'-trihydroxy-3,5-dimethoxychalcone (13). Based on the results, we concluded that the scavenging activity is controlled by the number and the position of the substitution in the compound.

• Natural Product Sciences
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• v.16 no.2
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• pp.75-79
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• 2010

Two new benzylated flavonoids, 5,7,4'-trihydroxy-6-p-hydroxybenzylflavanone (1) and 5,7,4'-trihydroxy-6,8-di-p-hydroxybenzylflavanone (2) together with six known flavonoids, kaempferol (3), artocarpesin (4), cycloartocarpesin (5), cudraflavone D (6), gericudranin E (7), and leachianone G (8) have been isolated from the root bark of Cudrania tricuspidata. The structures of 1 and 2 were characterized based on spectroscopic data including 1D- and 2D-NMR. All the isolates were evaluated for their inhibitory effects of monoamine oxidase (MAO). Among them, kaempferol (3), artocarpesin (4), and cudraflavone D (6) showed moderate inhibitory effects with $IC_{50}$ values of 82.3, 30.8, and $71.8\;{\mu}M$, respectively.

• Natural Product Sciences
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• v.11 no.4
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• pp.220-224
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• 2005

Extensive chemical studies on the stem bark extracts of two Guttifereous plants namely Mesua daphnifolia and Garcinia nitida have led to the isolation of eight xanthones. Mesua daphnifolia gave cudraxanthone G (1), ananixanthone (2), 1,3,5-trihydroxy-4-methoxyxanthone (3) and euxanthone (4) while Garcinia nitida gave inophyllin B (5), 1,3,7-trihydroxy-2,4-bis (3-methylbut-2-enyl)xanthone (6), 3-isomangostin (7) and rubraxanthone (8). All these compounds were assayed against the MDA-MB-231 (human estrogen receptor negative breast cancer) cells. A structure-activity relationship study showed that structurally, all the 1, 3-oxygenated xanthones which carried unsaturated prenyl side chains (either 3-methylbut-2-enyl or 1,1-dimethyl-2-propenyl) at carbones C-2 and C-4 in the xanthone ring A are essential for the outstanding activities in the assay.

• Archives of Pharmacal Research
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• v.28 no.2
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• pp.172-176
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• 2005

Phytochemical investigation of the whole plant of Amberboa ramosa led to the isolation of six sesquiterpene lactones which could be identified as $8{\alpha}$-hydroxy-$11{\beta}$-methyl-$1{\alpha}H,\;5{\alpha}H,\;6{\beta}H,\;7{\alpha}H,\;11{\alpha}H-guai-10(14)$, 4(15)-dien-6, 12-olide(2), $3{\beta},\;8{\alpha}-dihydroxy-11{\alpha}-methyl-1{\alpha}H,\;5{\alpha}H,\;6{\beta}H,\;7{\alpha}H,\;11{\beta}H-guai-10(14)$, 4(15)-dien-6, 12-olide (2), $3{\beta},\;4{\alpha},\;8{\alpha}-trihydroxy-4{\beta}(hydroxymethyl)-1{\alpha}H,\;5{\alpha}H,\;6{\beta}H,\;7{\alpha}H-guai-10(14)$, 11(13)-dien-6, 12-olide (3), $3{\beta},\;4{\alpha},\;8{\alpha}-trihydroxy-4{\beta}-(chloromethyl)-1{\alpha}H,\;5{\alpha}H,\;6{\beta}H,\;7{\alpha}H-guai-10(14)$, 11(13)-dien-6, 12-olide(4), $3{\beta},\;4{\alpha},\;dihydroxy-4{\beta}-(hydroxymethyl)-1{\alpha}H,\;5{\alpha}H,\;6{\beta}H,\;7{\alpha}H-guai-10(14)$, 11(13)-dien-6, 12-olide(5), $3{\beta},\;4{\alpha}-dihydroxy-4{\beta}-(chloromethyl)-8{\alpha}-(4-hydroxymethacrylate)-1{\alpha}H,\;5{\alpha}H,\;6{\beta}H,\;7{\alpha}H-guai-10(14)$, 11(13)-dien-6, 12-olide (6) by spectroscopic methods. All of them showed inhibitory potential against butyrylcholinesterase.

• Advances in Traditional Medicine
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• v.10 no.4
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• pp.319-321
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• 2010

Plant saponins are widely distributed amongst plants and have a wide range of biological properties. Icosahydropicenic acid, $C_{51}H_{80}O_{19}$ ((4S,6bS)-8a-((4,5-dihydroxy-6-methyl-3-((3R)-3,4,5-trihydroxy-6-methyl-tetrahydro-2H-pyran-2-yloxy)-tetrahydro-2H-pyran-2-yloxy)carbonyl)-2-hydroxy-4, 6a, 6b, 11, 14b-pentamethyl-11-(2-methylprop-1-enyl)-3-(3,4,5-trihydroxy-6-(hydroxymethyl) - tetrahydro-2Hpyran-2-yloxy)-1, 2, 3, 4, 4a, 5, 6, 6a, 6b, 7, 8, 8a, 9, 10, 11, 12, 12a, 14, 14a, 14b-icosahydropicene-4-carboxylic acid), a new saponin was first time isolated from the roots of Clerodendrum Serratum (L) Moon (Verbenaceae). The structure elucidation of the compound was carried out by $^1H$ NMR and DART-MS studies.

• YAKHAK HOEJI
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• v.32 no.2
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• pp.125-128
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• 1988

Geranylation of some synthetic and natural flavones have yielded cytotoxic products against L1210 coll; 5,2´-dihydroxy-6,7,8-trimethoxy-6´-geranyloxyflavone 4$(8.5{\mu}g/ml)$, 5,6-dihydroxy-7-gerenyloxyflavone 9$(2.3{\mu}g/ml)$. 2 has showed the same range of cytotoxicity as the starting material, 5,2´-dihydroxy-6,7,8-trimethoxy-6´-benzyloxyflavone$(17.0{\mu}g/ml)$. The cytotoxicity of 4 was lower than its starting substance, 5,2´,6´-trihydroxy-6,7,8-trimethoxyflavone $(4.5{\mu}g/ml)$. On geranylating 5,6,7-trihydroxyflavone(baicalein, $15.0{\mu}g/ml$) the cytotoxic activity has been strongly potentiated($2.3{\mu}g/ml$ of 9). The presence of at least a free hydroxy group in B-ring of Skullkapflavone II-type flavones. was essential for a high activity. A larger RD-group than methoxy in the B-ring has weakened the activity. The cytotoxicities of baicalein series could not be correlated to their structures.