• Bulletin of the Korean Chemical Society
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• v.30 no.8
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• pp.1729-1732
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• 2009

Bioactivity-guided fractionation led to the isolation of two new phenylpropanoids, 3-O-p-coumaroyl-1-(4-hydroxy- 3,5-dimethoxyphenyl)-1-propanone (1) and 3-O-p-coumaroyl-1-(4-hydroxy-3,5-dimethoxyphenyl)-1-O-$\beta$-gulcopyranosylpropanol (2), together with three known compounds, N-p-coumaroylserotonin (3), N-feruloylserotonin (4) and p-coumaric acid (5) from the leaves of Sasa quelpaertensis Nakai. Their structures were elucidated by spectroscopic methods including 1D and 2D-NMR. Compared to arbutin (I$C_{50}$ 0.048 mM) as a control, compounds 3 and 4 exhibited stronger tyrosinase inhibition activities with an I$C_{50}$ values of 0.027 mM and 0.026 mM, respectively. Compounds 1 (I$C_{50}$ 0.055 mM) and 2 (I$C_{50}$ 0.053 mM) also showed strong activities.

• Korean Journal of Pharmacognosy
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• v.4 no.2
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• pp.63-65
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• 1973

A component, $C_{20}H_{32}O_3$, m.p. $207.5^{\circ}$, was isolated from Siegesbeckia pubescens $M_{AKINO}$. This compound was identified as $17-hydroxy-16{\beta}-(-)-kauran-19-oic\;acid$, using spectroscopies and synthesizing various derivatives of the compound.

• YAKHAK HOEJI
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• v.44 no.2
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• pp.128-134
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• 2000

The synthesis of new 6-exomethylene penams with triazole ring was described. The 6,6-dibromopenam 5 was treated with $CH_3$MgBr and carbaldehyde 4 to afford the 6-bromo-6-(1-hydroxy-1-methyl)penicillanate 6, which was reacted with acetic anhydride to give acetoxy compound 7. The deacetobromination of 7 with zinc and acetic acid gave 6-exomethylenpenams, Z-isomer 8 and E-isomer 9, which were oxidized to sulfones 10 and 11 by m-CPBA. The p-methoxybenzyl compounds 6~11 were deprotected by AlCl$_3$ and neutralized to give the sodium salts 12~17.

• Archives of Pharmacal Research
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• v.26 no.1
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• pp.24-27
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• 2003

A furanofuranoid lignan glycoside, with radical scavenging on peroxynitrite, total reactive oxygen species (ROS) and 1, 1-diphenyl-2-picrylhydrazyl (DPPH) radical, was isolated from the rhizome of Salvia miltiorrhiza and characterized as (+)-1-hydroxypinoresinol-1-Ο-$\beta$-D-glucoside based on spectroscopic evidence. The compound exhibited peroxynitrite, total ROS and DPPH radical scavenging activities with $IC_{50}$ values of 3.23$\pm$0.04, 2.26$\pm$0.07 and 32.3$\pm$0.13 $\mu$M, respectively. Penicillamine, Trolox (6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid) and L-ascorbic acid, acting as positive controls, showed radical scavenging activities with $IC_{50}$ values of 6.72$\pm$0.25, 1.43$\pm$0.04 and 11.4$\pm$0.07 $\mu$M, respectively.

• Asian-Australasian Journal of Animal Sciences
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• v.12 no.5
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• pp.682-688
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• 1999

Thirty nine pregnant Javanese thin-tail ewes (20 and 19 carried a single and multiple [2 to 3] fetuses, respectively), and six nonpregnant ewes as controls were used to measure maternal serum hormone and blood metabolite concentrations as predictors of number of fetuses carried during pregnancy. Serum hormones (progesterone, estradiol, triiodothyronine, and cortisol) and blood metabolites (b-hydroxy butyric acid [BHBA], and blood urea nitrogen [BUN]) were determined every four weeks during pregnancy and were used to predict litter size by discriminant analysis. The results of data analysis indicated that serum progesterone and estradiol concentrations at weeks 8, 12, 16 of pregnancy could be used to predict the number of fetuses carried with precision of 86.7 to 95.6%. Serum triiodothyronine, cortisol, BHBA, and BUN concentrations during pregnancy, however, were not good predictors of the number of fetuses carried. Serum progesterone and estradiol concentrations as early as 8 weeks of pregnancy in sheep could predict the number of fetuses carried with 86.7% precision.

• Journal of Life Science
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• v.27 no.3
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• pp.325-333
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• 2017

High level of plasma cholesterol is strongly associated with the development of atherosclerosis and coronary heart disease. Clinical trials designed to reduce plasma cholesterol level by diet or pharmacological intervention have resulted in marked reduction of disease incidence. The enzyme 3-hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) reductase which reduces cholesterol biosynthesis in the liver is the key enzyme of the mevalonate pathway that produces cholesterol. In this study, 71 naturally occurring phenolic compounds were tested for inhibitory activities against HMG-CoA reductase. Eleven compounds out of 71 showed inhibitory activities: three hydrolyzable tannin (geraniin, acetonyl geraniin and pentagalloyl ${\beta}-D-glucose$), four benzoic acid derivatives (benzoic acid, trans-cinnamic acid, 2,4-dihydroxybenzoic acid and 2,5-dihydroxybenzoic acid), and four naphthoquinone derivatives (1,2-naphthoquinone, 1,4-naphthoquinone, plumbagin and shikonin). At the concentration of $10{\mu}g/ml$, 1,4-naphthoquinone inhibited HMG-CoA reductase by 99.4%, and then plumbagin 91.4%, pentagalloyl ${\beta}-D-glucose$ 46.6%, 2,4-dihydroxybenzoic acid 40.9%, shikonin 37.7%, 1,2-naphthoquinone 36.6%, trans-cinnamic acid 32.0%, acetonyl geraniin 30.2%, benzoic acid 28.5%, geraniin 28.3% and 2,5-dihydroxybenzoic acid 22.3%, respectively. $IC_{50}$ values of 1,4-naphthoquinone and plumbagin was $2.1{\mu}g/ml$ and $5.8{\mu}g/ml$, respectively.

• Archives of Pharmacal Research
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• v.23 no.3
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• pp.243-245
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• 2000

The diethyl ether extract of isodon excisus var. coreanus exhibited significant inhibitory activity in aromatase assay. Bioactivity-guided fractionation of the extract led to the isolation of three active compounds: inflexin(ent-1${\alpha}$-hydroxy-3${\beta}$,6a-diacetoxykau r-16-en-11,15-dione) (1), ursolic acid (2), and ursolic acid 3-O-acetate (3).

• Archives of Pharmacal Research
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• v.28 no.5
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• pp.534-540
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• 2005

Activity-guided fractionation of the CH$_2Cl_2$-soluble fraction of the roots of Sophora flavescens furnished five 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical scaveng ers: trans-hexadecyl ferulic acid (1) cis-octadecyl ferulic acid (2), trans-hexadecyl sinapic acid (3), (-)-4-hydroxy-3-methoxy-(6aR,11aR)-8, 9-methylenedioxypterocarpan (4) and desmethylanhydroicaritin (8), along with nine known inactive compounds: (-)-maackiain (5), xanthohumol (6), formononetin (7), (2S)-2'-methoxykurarinone (9), (2S)-3${\beta}$,7,4'-trihydroxy-5-methoxy-8-(${\gamma},{\gamma}$- imethylallyl )-flavanone (10), (2S)-7,4'-dihydroxy-5-methoxy-8- (${\gamma},{\gamma}$-dimethylallyl ) -flavanone (11), umbelliferone (12), kuraridin (13), and trifolirhizin (14). Compounds 1-4 and 8 exhibited DPPH free radical scavenging effects at IC$_{50}$ values of 33.01 ${\pm}$ 0.20, 57.06 ${\pm}$ 0.16, 39.84 ${\pm}$ 0.36, 35.83 ${\pm}$ 0.47, and 18.11 ${\pm}$ 0.04${\mu}$M, respectively. L-Ascorbic acid, when used as a positive control, exhibited an IC$_{50}$ value of 7.39 ${\pm}$ 0.01 ${\mu}$M. Compounds 1-4 and 8 also appeared to exert significant scavenging effects on authentic ONOO-, with IC$_{50}$ values of 5.76 ${\pm}$ 1.19, 15.06 ${\pm}$ 1.64, 8.17 ${\pm}$ 4.97, 1.95 ${\pm}$ 0.29 and 4.06 ${\pm}$ 2.41 ${\mu}$M, respectively. Penicillamine (IC$_{50}$= 2.36 ${\pm}$ 0.79${\mu}$M) was used as a positive control. In addition, compounds 2,4,6,8, and 10 were isolated from this plant for the first time.

• Natural Product Sciences
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• v.14 no.1
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• pp.56-61
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• 2008

Bioactivity guided phytochemical study of the petroleum ether and butanol extracts of Clematis hirsuta resulted in the isolation of 12 compounds. Rat paw edema as a model of acute inflammation was used to evaluate the anti-inflammatory activity of the extracts and the chromatographic fractions. Five known sterols and triterpenes namely: ${\beta}-amyrin$ (1), lupeol (2), ${\beta}-sitosterol$ (3), oleanolic acid (4) and stigmasterol glycoside (5) were isolated from the petroleum ether extract. The n-butanol extract afforded two compounds reported for the first time from natural source: (S)-(+)-dihydro-5-(hydroxymethyl)-2(3H)-furanone (7) and (s)-(-)-5-hydroxymethyl-2(5H)-furanone (8). In addition, anemonin (6), dihydro-4-hydroxy-5-(hydroxymethyl)-2(3H)-furanone (2-deoxy-D-ribono-1,4-lactone) (9), biophenol (cimidahurin) (10), glucose (11) and sucrose (12) were also identified. The structures were determined from spectroscopic data including 1D- and 2D-NMR experiments.

• Proceedings of the Korean Society of Applied Pharmacology
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• 1993.04a
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• pp.117-117
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• 1993

3. 연구결과 출발물질로 L-tyrosine을 사용하여 요오드화, 에스테르화, N-CBZ 및 0-Bn보호기화 및 N-methyl화를 행하여 5단계에 걸쳐 41%의 수율로 N-CBZ-N-methyl-0-Bn-3-iodo-tyrosine을 합성하였다. Ullmann coupling의 반응성 검토를 위해 t-bromophenylala-nine에 반응시킬 3-hydroxytyrosine 유도체를 합성하고자 L-tyrosine에 Friedel-Craft acyl화, 에스테르화, 아민의 보호기화 및 Baeyer-Villiger 반응들을 행하였다. 또한 특이한 아미노산인 $\beta$-hydroxytyrosine의 합성을 위해 출발물질로 p-hydroxybenzalde-hyde를 사용하여 6단계에 28%의 수율로 oxazolidinoe acid를 합성하였다. 이로부터 4단계 반응을 행하여 보호된 $\beta$-hydroxy-tyrosine을 52%의 수율로 합성하였다.