• Archives of Pharmacal Research
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• 제19권3호
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• pp.240-242
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• 1996

We have reported the convenient biomimetic methodology for the synthesis of all kinds of substituent pattern benzo[c]phenanthridine alkaloids (Hanaoka et al., 1990; Hanaoka et al., 1991). Regioselective demethylation of C-8 position on oxyfagaridine (5), an intermediate for the synthesis of Fagaridine (4), would afford the precursor for the synthesis of Isofagaridine because the strong hydrogen bonding between amide and hydroxyl group of C-7 position probably resists to be reacted with week base and electrophiles. Thus, a selective alkylation of dihydroxy compound supposed to be possible and be lead to the target compound, Isofagaridine.

• Food Science and Biotechnology
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• 제16권6호
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• pp.963-966
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• 2007

The objectives of this study were to identity antioxidant substance in heated garlic juice (HGJ). We evaluated the antioxidant activities of heated garlic juice exposed to 120, 130, and $140^{\circ}C$ for 2 hr. The HGJ was partitioned using the solvents of hexane, chloroform, ethyl acetate, butanol, and water. The ethyl acetate fraction of HGJ treated at $130^{\circ}C$ for 2 hr showed strong antioxidant activity; this extract was isolated and purified using silica gel column chromatography and semi-preparative high-performance liquid chromatography. The structure of the purified compound was determined using spectroscopic methods, i.e., ultraviolet, mass spectrometry, infrared, $^1H$ NMR, $^{13}C$ NMR, DEPT, HMBC, and HMQC. The isolated compound was identified as thiacremonone (2,4-dihydroxy-2,5-dimethyl-thiophene-3-one). Thiacremonone showed strong 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical-scavenging activity, with a 50% inhibition concentration ($IC_{50}$) of $22.25{\pm}0.44\;{\mu}g/mL$, which is much higher than that of the antioxidants ascorbic acid ($30.06{\pm}0.42\;{\mu}g/mL$), ${\alpha}$-tocopherol ($71.30{\pm}0.97\;{\mu}g/mL$), and butylated hydroxyanisole ($50.54{\pm}0.94\;{\mu}g/mL$).

• 대한화학회지
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• 제40권9호
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• pp.623-629
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• 1996

지의류에 속하는 Umbiliciaria vellea 중 에탄올 분획의 항균활성 물질을 규명하기 위하여 silica겔 컬럼 크로마토그래피 및 재결정법으로 화합물 I과 II를 순수히 분리정제하여 그 구조와 항균활성을 측정하였다. 정제된 화합물I은 Cryptococcus neoformance 등의 균에 대한 항진균활성과, Pseudomonas aeruginosa등의 균에 대한 항세균 활성이 있었다. 이 물질의 녹는점은 129~132$^{\circ}C$였고, 217, 265 및 330 nm의 UV 최대흡광을 보였다. 그리고 EI-mass에서 측정된 분자이온은 m/z 196이었고, 원소분석 결과 분자식은 $C_{10}H_{12}O_4$였으며 IR 및 NMR 스펙트라로부터 이 물질이 ethyl 2,4-dihydroxy-6-methyl benzoate임을 확인하였다. 화합물 II의 녹는점은 58~59$^{\circ}C$였고, 212, 276 및 282 nm의 UV 최대흡광을 보였다. 이 물질의 분자이온은 m/z 124였고, $C_7H_8O_2$의 분자식을 갖는 5-methyl-1,3-benzenediol임을 확인하였다.

• 대한의생명과학회지
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• 제18권3호
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• pp.307-309
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• 2012

(S)-(+)-3(3,4-dihydroxy-phenyl)-acrylic acid 2,2-dimethyl-8-oxo3,4-dihydro-2H,8H-pyrano[3,2-g]Chromen-3-yl-ester (Compound 6, C6) is synthesized from (S)-(+)-decursin and attenuates the pathophysiologic progression of asthma in a ovalbumin-induced asthmatic mouse model. In the present study, we examined the effect of C6 on spontaneous apoptosis of eosinophils and neutrophils of normal and asthmatic subjects. C6 increased the apoptosis of asthmatic eosinophils in a dose-dependent manner, but it inhibited neutrophil apoptosis. C6 has no effect on apoptosis of normal eosinophils and neutrophils. LY294002, an inhibitor of PI3K, rottlerin, an inhibitor of $PKC{\delta}$, Ro-31-8425, an inhibitor of classical PKC inhibitor, PD98059, an inhibitor of MEK, and BAY 11-7085, an inhibitor of NF-${\kappa}B$, blocked the inhibitory effect on apoptosis of asthmatic neutrophils due to C6. These results indicate that C6 may be valuable as a therapeutic agent for the treatment of asthma.

• 생약학회지
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• 제33권3호통권130호
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• pp.173-176
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• 2002

In search for the plant-derived antioxidant compound, it was found that the EtOAc, BuOH extracts obtained from the leaves parts of Oryza sativa L. which exhibited a significant antioxidant activity from 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical cleavage. Activity-guided fractionation on the basis of the inhibitory activity upon the 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical cleavage. and repeated column chromatography afforded several antioxidant compounds from Oryza sativa L. The structures and stereochemistry of these compounds were established on the basis of analysis of spectra and some chemical transformations as follows: 5,7-dihydroxy- 8-methoxyflavone, $acacetin-7-O-{\beta}-rutinoside$, $pectolinarigenin-7-O-{\beta}-rutinoside$. At antioxidant activity test for isolated three compounds, antioxidant activity was showed too.

• Archives of Pharmacal Research
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• 제29권12호
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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 $1.32\;to\;3.85\;{\mu}M$.

• Natural Product Sciences
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• 제26권2호
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• pp.151-157
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• 2020

Extensive column chromatography separation of the MeOH extract from the aerial parts of Phyllanthus urinaria afforded seventeen compounds (1 - 17). The structures of the compounds were elucidated by physicochemical and spectroscopic methods to be 5'-β-D-glucopyranosyloxyjasmonic butyl ester (1), (+)-cucurbic acid (2), dendranthemoside B (3), boscialin 4'-O-β-D-glucoside (4), 4,5-dihydroblumenol A (5), (6R,9R)-megastigman-4-ene-9,13-diol (6), (3S,5R,6S,9R)-3,6-dihydroxy-5,6-dihydro-β-ionol (7), (6S,9R)-roseoside (8), mallophenol B (9), icariside B₅ (10), corchoinoside B (11), canangaionoside (12), 5,6-epoxy-3-hydroxy-7-megastigmen-9-one (13), icariside B₂ (14), (7E)-2β,3β-dihydroxy-megastigm-7-en-9-one (15), betulalbuside A (16), and loliolide (17). The compounds 1, and 3 - 16 were isolated for the first time from this plant. The absolute stereochemistry of compound 1 was newly determined. The isolated compounds were tested for cytotoxic activity against four human tumor cell lines in vitro using a Sulforhodamin B bioassay, but all the compounds showed weak cytotoxic activities.

• Archives of Pharmacal Research
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• 제28권12호
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• pp.1345-1349
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• 2005

Six phenolic constituents, 2-methoxybenzyl benzoate (1), negletein (2), 2',3'-dihydroxy-4',6'­dimethoxydihydrochalcone (3), 5,6-dihydroxy-7-methoxy-dihydroflavone (4), astilbin (5), and quercitrin (6) were isolated from the methanol extract of the dried leaves of Desmos chinensis. Their structures were elucidated from spectral and chemical data. Of these constituents, compounds 2 ($IC_{50}$: 3.89 $\pm$ 0.39 $\mu$M) and 3 ($IC_{50}$: 9.77 $\pm$ 0.26 $\mu$M) exhibited potent inhibitory activity against nuclear factor of activated T cells (NFAT) transcription factor, and compound 1 ($IC_{50}$: 28.4 $\pm$ 2.62 $\mu$M) exhibited moderate inhibitory activity.

• 한국환경과학회지
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• 제26권11호
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• pp.1285-1295
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• 2017

Chrysanthemum boreale Makino is widely distributed in Korea, China, Japan and Southeast Asian countries. C. boreale is one of the herbs used for treating various inflammatory diseases in oriental medicine. The present study was conducted to identify biologically active compounds from the leaves and stems of C. boreale. We isolated two sesquiterpene sactones from the leaves and stems of C. boreale using silica gel column chromatography and recyclic high perfomance liquid chromatography. The lactones were characterized by their spectroscopic data (NMR, IR, MASS). These compounds were subjected to Farnesyl Protein Transferase (FPTase) inhibition, Nitric Oxide (NO) release inhibition and apoptosis inhibition. The structur of the following isolated compound were elucidated 8,10-${\small{O}$-Acetyl-2-methoxy-10-hydroxy-3,11(13)-guaiadiene-12,6-olide and 4,10-dihydroxy-8-${\small{O}$-Acetyl-2,11(13)-guaiadiene-12,6-olide. In the NO release inhibition assay, compound 2 showed strong activities, with an $IC_{50}$ value of $7{\mu}g/mL$, whereas compound 1 did not exhibit significant activity with an $IC_{50}$ value of over $14{\mu}g/mL$ against murine macrophage.

• 생약학회지
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• 제25권3호
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• pp.209-213
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• 1994

For the investigation of medicinal resources from Taraxacum species, the studies were carried out to evaluate the pharmaco-constituents in the aerial part of Taroxacum hallaisanensis, an endemic plant of Korea. From BuOH fraction of the MeOH extract, compound 1 (protocatechuic acid, $C_7H_6O_4,\;3,4-dihydroxy\;benzoic\;acid)$, compound 2 $[C_{22}H_{31}O_6,\;luteolin-7-O-{\alpha}-_L-rhamnopyranosyl(1{\rightarrow}6)-{\beta}-_D-glucopyranoside]$, and compound 3 $[C_{15}H_{20}O_6,\;luteolin-7-O-{\beta}-_D-glucopyranoside]$ were isolated by column chromatographic separation using polyamide and ODS-gel. The structures were elucidated by means of physico-chemical evidences($^1H-NMR,\;{12}^C-NMR$, IR, EI-Mass, FAB-Mass and GC).