• Archives of Pharmacal Research
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• 제27권7호
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• pp.738-741
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• 2004

Three lignans isolated from the roots of A. koreanum (Araliaceae), namely eleutheroside E(1), tortoside A(2), and hemiariensin(4), were evaluated for their ability to inhibit NFAT transcription factor. Of these compounds, compound 4, possessing a diarylbutane skeleton, exhibited potent inhibitory activity against NFAT transcription factor (($IC_{50}$ ： 36.3${\pm}2.5{\mu}\textrm{M}$). However, the activities of 1 (($IC_{50}$：＞500 11M) and 2 (($IC_{50}$： 136.1 ${\pm}9.4\mu\textrm{M}$), which possess bisaryldioxabicy-clooctane skeletons, were lower. As the lignan derivatives of the same skeletons, hinokinin (5) and (-)-yatein (6) with diarylbutane skeletons and(＋)-syringaresinol (3) with a bisaryldioxabicy-clooctane skeleton were also studied for their inhibitory effects on NFAT transcription factor.

• 대한약학회:학술대회논문집
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• 대한약학회 2002년도 Proceedings of the Convention of the Pharmaceutical Society of Korea Vol.2
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• pp.382.2-382.2
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• 2002

Melanin biosynthesis inhibitors are useful not only for the materials used in cosmetics as skin-whitening agents but also for the remedy of hyperpigmentation. In order to find the new skin-whitening compounds from the natural products. screening of tyrosinase and melanin biosynthesis inhibitory activities in vitro has been carried out. The MeOH extracts and/or fractions of Polygoni multiflori Radix, Dalbergiae odoriferae Lignum. Solnani nigri Herba. Polygoni cuspidati Radix. POlygoni multiflori Ramulus. Salviae Radix showed tyrosinase inhibitory effects. Four methanolic extracts also showed melanin biosynthesis inhibitory effects in B-16 melanoma cell line.

• Bulletin of the Korean Chemical Society
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• 제27권7호
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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.

• Applied Biological Chemistry
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• 제45권3호
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• pp.168-172
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• 2002

한국산 옻나무의 메탄올추출물과 유기용매 분획의 항산화 효과를 조사하였다. 항산화 효과는 수소공여 억제능, 과산화지질 형성 억제능, xanthine oxidase저해 활성과 아질산염 소거능으로 측정한 결과, ethyl acetate 분획이 가장 뛰어난 효과를 나타내었다. 이 분획의 생리활성 물질을 분리하기 위하여, rotatory locular counter current chromatography(RLCCC), Sephadex LH-20 column chromatograpy와 HPLC등의 방법을 사용하여, 1,2,3-trihydroxybenzene, methyl 3,4,5-trihydroxybenzoat와 3,4,5-trihydroxybenzoic acid를 분리하였다. 이중 methyl 3,4,5-trihydroxybenzoate는 butylated hydroxyanisole(BHA)이나 butylated hydroxytoluene(BHT)보다도 강한 항산화 효과를 나타내었다. 그러나 세포독성 실험에서는 이들 물질들이 암세포주에 대하여 활성이 높지 않았다. 이상의 결과로 methyl 3,4,5-trihydroxybenzoate은 뛰어난 항산화 효과를 지닌 식품첨가물로서의 이용 가능성을 제시할 수 있다.

• 한국환경과학회지
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• 제26권11호
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• pp.1275-1284
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• 2017

Acyltransferase (AT) catalyzes the transfer of an acyl moiety from acyl-coenzyme A (acyl-CoA) to an acceptor. ATs play important roles in the maintenance of homeostasis in the human body and have been linked to various diseases; therefore, several ATs have been proposed as potential targets for the treatment or prevention of such diseases. The AT family includes acyl-CoA:cholesterol AT (ACAT), diacylglycerol AT, and monoacylglycerol AT for the metabolism of lipids. Furthermore, recent molecular biological studies revealed the existence of their isozymes with distinct functions in the body. ACAT plays a critical role in the formation of cholesteryl esters from cholesterol and fatty acids, and is a potential target for treating hypercholesterolemia. During an experiment designed to discover biologically active compounds from herbal medicines, we isolated two known guaianolide sesquiterpene lactones from Chrysanthemum boreale Makino (Compositae). The lactones were characterized from their spectroscopic data (NMR, IR, MASS). These compounds were subjected to ACAT inhibition assay. Here, we report the isolation and structural elucidation of the compounds 8-o-acetyl-2-methoxy-10-hydroxy-3,11(13)-guaiadiene-12,6-olide and 8-acetyl-3,10-hydroxy-4(15),11(13)-guaiadiene-12,6-olide. In the ACAT inhibition assay, compound 1 showed strong inhibitory activity, with an $IC_{50}$ value $45{\mu}g/mL$, whereas compound 2 did not exhibit significant inhibitory activity with an over $100{\mu}g/mL$.

• Bulletin of the Korean Chemical Society
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• 제32권6호
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• pp.2015-2020
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• 2011

A series of isoxazol-indolin-2-one was designed for GSK-3${\beta}$ inhibitors as novel anticancer agents based on their binding mode analysis in GSK-3${\beta}$ crystal structure. Total 21 compounds were synthesized and evaluated for their inhibitory activity against two tumor cell lines (DU145 and HT29). Most of the synthesized compounds were potent with above 80% inhibitory activity at 100 ${\mu}M$, and several compounds were examined for inhibitory activity against GSK-3${\beta}$. Among them, 15(Z) ($R_1$=H, $R_2$=3-Cl-phenyl) was most active with 78% inhibition of tumor cell line (HT29) at 20 ${\mu}M$ and 72% inhibition of GSK-3${\beta}$ at 20 ${\mu}M$.

• Applied Biological Chemistry
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• 제41권1호
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• pp.99-103
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• 1998

Triazolopyrimidine sulfonanilide (TP) 유도체는 널리 사용되고 있는 제초제 중의 하나이다. 우리는 TP 유도체 화합물의 골격을 이루고 있는 벤젠 고리를 pyrimidine 고리로 치환시킨 새로운 3 종류의 sulfonamide 유도체(TPP)를 합성하고, 보리에서 추출한 acetolactate synthase (ALS)의 저해 활성도를 측정한 결과 0.005 부터 2 mM 사이의$I_{50}$값을 얻었다. $I_{50}$ 값의 비교에서 pyrimidine 고리에 methyl기가 치환된 TPP 유도체는 methoxy기가 치환된 유도체 보다 높은 저해 활성도를 나타내었다. 또한 triazolopyrimidine 고리에 cyclopentano 고리로 치환된 TPP 유도체는 methyl- 및 phenyl가 치환된 유도체보다 우수한 저해 활성도를 보였다. 따라서 새로운 TPP 유도체의 제초 효력은 치환기에 의한 분자내 전자 분포 변화와 밀접한 관계가 있으나 치환기의 크기에 따른 입체적 장애 요인은 저해 활성도에 전혀 영향이 없음을 알 수 있었다.

• Natural Product Sciences
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• 제25권4호
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• pp.348-353
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• 2019

Soluble epoxide hydrolases (sEH) are enzymes present in all living organisms, metabolize epoxy fatty acids to 1,2-diols. sEH in the metabolism of polyunsaturated fatty acids plays a key role in inflammation. In addition, the endogenous lipid mediators in cardiovascular disease are also broken down to diols by the action of sEH that enhanced cardiovascular protection. In this study, sEH inhibitory guided fractionation led to the isolation of five phenolic compounds trans-resveratrol (1), trans-piceatannol (2), sulfuretin (3), (+)-balanophonin (4), and cassigarol E (5) from the ethanol extract of the seeds of Passiflora edulis Sims cultivated in Vietnam. The chemical structures of isolated compounds were determined by the interpretation of NMR spectral data, mass spectra, and comparison with data from the literature. The soluble epoxide hydrolase (sEH) inhibitory activity of isolated compounds was evaluated. Among them, trans-piceatannol (2) showed the most potent inhibitory activity on sEH with an IC₅₀ value of 3.4 μM. This study marks the first time that sulfuretin (3) was isolated from Passiflora edulis as well as (+)-balanophonin (4), and cassigarol E (5) were isolated from Passiflora genus.

• Preventive Nutrition and Food Science
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• 제22권2호
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• pp.107-117
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• 2017

The purpose of this study was to evaluate the antioxidant and anticholinesterase activities of yellow and white bitter yams from South Western Nigeria using methanolic extraction and simulated gastrointestinal digestion models. The phenolic compounds in the bitter yam varieties were evaluated by high performance liquid chromatography with a diode array detector (HPLC-DAD). The total phenolic content of the bitter yams was measured by the Folin-Ciocalteu method, reductive potential by assessing the ability of the bitter yam to reduce $FeCl_3$ solution, and the antioxidant activities were determined by the 2,2-diphenyl-1-picrylhydrazyl radical ($DPPH^{\cdot}$) scavenging activity, 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) radical cation ($ABTS^{{\cdot}+}$) scavenging activity, nitric oxide radical ($NO^{\cdot}$) scavenging ability, hydroxyl radical scavenging ability, and ability to inhibit $Fe^{2+}$-induced lipid oxidation. The HPLC-DAD analysis revealed the presence of some phenolic compounds in the studied bitter yam varieties, with varying degree of quantitative changes after cooking. The antioxidant indices (total phenolic content, total flavonoid content, reducing power, $DPPH^{\cdot}$ scavenging activity, $ABTS^{{\cdot}+}$ scavenging activity, and $NO^{\cdot}$ scavenging activity) were higher in the simulated gastrointestinal digestion model compared to the methanolic extract, with the in vitro digested cooked white bitter yam ranking higher. Similarly, the in vitro digested yams had a higher inhibitory action against lipid oxidation compared to the methanolic extracts, with the cooked white bitter yam ranking high. The methanolic extracts and in vitro enzyme digests showed no acetylcholinesterase inhibitory abilities, while methanolic extracts and the in vitro enzyme digest displayed some level of butyrylcholinesterase inhibitory activities. Therefore the studied bitter yams could be considered as possible health supplements.

• 한국환경과학회지
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• 제28권11호
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• pp.993-1004
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• 2019

Chrysanthemum boreale Makino (C. boreale) is widely distributed in Asian countries, and has traditionally been used to treat various inflammatory diseases including bronchitis. In this study, we aimed to isolate biologically active compounds from leaves and stems of C. boreale. Chemical components were purified by column chromatograpy and recyclic HPLC, and characterized from their spectral data (IR, MS, NMR). Biological activity experiments were conducted for Farnesyl-protein transferase (FPTase) activity, apoptosis and nitirc oxide (NO) release. As a results, three sesquiterpene lactones were isolated. Compound 1 (4-methoxy-8-O-acetyl-10-hydroxy-2,11(13)-guaiadiene-12,6-olide) showed strong cytotoxic activities having an average growth inhibition of 50% ($GI_{50}$) value of $1.89{\mu}g/m{\ell}$ against human colon adenocarcinoma cells. Compound 1 also showed a low half maximal inhibitory concentration ($IC_{50}$) value of $10{\mu}g/m{\ell}$ for NO release. In the caspase 3 activity, compound 1 and compound 2 (8-O-(2-carbonyl-2-butyl)-3,10-dihydroxy-4,11(13) -guaiadiene-12,6-olide) exhibited 94% and 90% apoptosis inhibition activity, respectively. Compound 3 (4,8-O-diacetyl -10-hydroxy-2(3),11(13)-guaiadiene-12,6-olide) showed a strong inhibitory effect on FPTase activity with 90% inhibitory activity at a concentration of $100{\mu}g/m{\ell}$. These results clearly show the presence of lactone compounds in the leaves and stems, which may partially contribute to the pharmacological activity of C. boreale.