• Journal of the Korean Society of Food Science and Nutrition
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• v.43 no.1
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• pp.93-101
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• 2014

Asymmetric 1,2-distearoyl-3-oleoyl-rac-glycerol (SSO) triacylglycerol (TAG) is used as a cocoa butter replacer (CBR). In this study, it was produced by lipase-catalyzed interesterification of fully hydrogenated soybean oil (FHSBO) and oleic ethyl ester (OEE) in a batch type reactor at $75^{\circ}C$, 250 rpm. Different molar ratios (FHSBO : OEE=1:1, 1:2 and 1:3, w/w) and various reaction times (1, 2, 3, 4, and 5 hr) were also tested. The optimized condition for SSO was a FHSBO : OEE molar ratio of =1:1 at reaction times of 2, 3, 4, and 5 hr. Enzymatic synthesis generated SSO/SOS, as well as the other TAGs (e.g., PSO/POS, SOO/OSO, SSS), ethyl esters, monoacylglycerol (MAG), and diacylglycerol (DAG). After scale-up, fractionation by solvent (methanol and acetone) fractionation and column chromatography was applied. To reduce ethyl esters, high-melting TAGs (e.g., SSS), and SOO/OSO in reactants, solvent fractionation was applied. Using a silica gel column (sample : silica gel=2:1, wt%), MAG and DAG were removed at $25^{\circ}C$. The major fatty acid composition of the final products (with a high SSO/SOS content) was palmitic acid (C16:0, 10.9~12.9 area%), stearic acid (C18:0, 52.2~54.9 area%), and oleic acid (C18:1, 34.2~35.5 area%). In reversed-phase HPLC analysis, the major TAG species of the final product (FHSBO : OEE=1:1, 2 hr) were SSO/SOS (82.31 area%) and PSO/POS (14.51 area%). Based on the $[SS]^+$ : $[SO]^+$ ratio obtained by RP-HPLC/APCI-MS, the final product had a higher SSO (AAB type TAG) content than cocoa butter (CB). The solid fat index (SFI) of CB and the final product obtained were similar with a narrow melting point range around ~32 to $35^{\circ}C$.

• Journal of Life Science
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• v.19 no.5
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• pp.671-675
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• 2009

Prostate cancer has been a critical health problem due to an increase of prostate cancer-related deaths worldwide. Also, a frequent treatment option for prostate cancer is androgen ablation, but this treatment has a limited scope, especially for hormone-refractory cancer. There is an urgent need for the identification of alternative therapeutic strategies for prostate cancer. Previously, over one hundred species of dried-plant methanol extracts were tested for inhibitory effects on proliferation. One of them, Piper longum Linn. was selected based on its potent anti-proliferation effect. The dried root of P. longum Linn. was extracted with 100% methanol for 2-3 days and its extract was fractionated using chloroform. The chloroform layer was then subjected to column chromatography on silica gel, reverse phase-18 (RP-18) and Sephadex LH-20, in turn. Finally, the pure compound was obtained and identified as pipernonaline by NMR spectroscopic and physico-chemical analysis. In this study, anti-proliferation and cell cycle arrest effects of pipernonaline on human prostate cancer PC-3 cells were investigated using the MTT and PI staining, respectively. Our findings suggest that pipernonaline represents a dose-dependent growth inhibition pattern on PC-3 cells and, moreover, its growth inhibition is associated with sub-G1 and G0/G1 cell cycle accumulation in PC-3 cells. Also, these results provide an anticancer candidate for human prostate cancer.

• Korean Journal of Food Science and Technology
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• v.44 no.5
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• pp.621-627
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• 2012

Assessment was made of the effects of Aralia cordata Thunb (DH) on the cell proliferation, inducible nitric oxide synthase (iNOS) mRNA gene expression and nitric oxide (NO) production in RAW 264.7 macrophage cells. For the screening of anti-inflammatory activities, ethanolic extracts of 55 species of traditional herbal medicines were examined for inhibitory effects, and it was confirmed that DH possessed inhibitory effects on NO production. As a result, DH significantly decreased the production of NO and iNOS gene expression at a concentration of $250{\mu}g/mL$. The chloroformsoluble fractionates have the strongest No synthesis inhibitory effect. It is presumed that the inhibition of NO production in LPS-stimulated RAW 264.7 cells by DH components occurred via the modulation of iNOS and DH, and that the active compound from DH may be useful for therapeutic management of inflammatory-associate diseases.

• Korean Journal of Medicinal Crop Science
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• v.12 no.3
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• pp.255-261
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• 2004

The MeOH extracts from 21 species were tested for their cytotoxicity against SK-MEL-28 melanoma cell line and HaCat normal cell line in 5 g/ml by sulforrhodamine-B (SRB) method. Among them, the MeOH extract from Moutan Cortex Radicis showed the moderate activity with the growth rate of 74.3% in SK-MEL-28 cells and the high activity with the growth rate of 207.8% in HaCat cells. Activity-guided fractionation was performed and five compounds, paeonol (1), benzoylpaeoniflorin (2), benzoic acid (3), 2,5-dihydroxy-4-methoxy- acetophenone (4), paeonfliorin (5) were isolated from hexane and EtOAc fraction. The structures were established by physicochemical and spectrometric methods $(mp,\;UV,\;IR,\;^1H-NMR,\;^{13}C-NMR,\;spectram)$. All compounds were evaluated for their cytotoxicity, compound 4 showed the significant cytotoxic activity with $ED_50$ value of $5.92\;{\mu}g/ml$, but the other compounds no activity. These results suggest that compound 4 is a novel anticancer candidate against SK-MEL-28 melanoma cells.

• Korean Journal of Food Science and Technology
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• v.43 no.1
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• pp.51-57
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• 2011

From the total methanolic extract of Gardenia jasminoides (Rubiaceae), various antioxidative characteristics were identified in terms of nitrite scavenging ability, 2,2'-azino-bis (3-ethylbenzthiazoline-6-sulphonic acid) (ABTS) radical cation inhibition, superoxide dismutase (SOD)-like activity, and elongation effect of lipid peroxidation using Rancimat. After successive partitioning with n-hexane, chloroform, n-butanol, and water, potent nitrite scavenging abilities were shown in the n-butanol fraction and water fraction, and $IC_{50}$ values were 183 ppm and 194 ppm, respectively. As for ABTS radical cation inhibition, the chloroform fraction was most potent and its $IC_{50}$ was 159 ppm. SOD-like activity was slightly low in all of the fractions. The elongation effect of lipid peroxidation also increased dose-dependently and the antioxidative index (AI) of the total methanolic extract was 2.93 in 1000 ppm, which was more effective than 1.66 of butylated hydroxy anisol in the same concentration. The compounds I and II were isolated through silica gel column chromatography of the active fractions, and identified as geniposide and crocin, respectively, by $^1H-NMR$ spectral data. The $IC_{50}$ values for the nitrite scavenging abilities of geniposide and crocin were 940 ppm and 77 ppm, respectively. In ABTS radical cation inhibition, the $IC_{50}$ values of geniposide and crocin were 684 ppm and 549 ppm, respectively. And the $EC_{50}$ value for SOD-like activity of crocin was 259 ppm, which was much smaller than 453 ppm by the positive control, chlorogenic acid. The $EC_{50}$ value of geniposide could not be identified.

• Journal of the Korean Society of Food Science and Nutrition
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• v.26 no.2
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• pp.236-241
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• 1997

Inhibitory effects of several edible plant extracts against 3-hydroxy-3-methylglutaryl coenzyme A(HMG-CoA) reductase, a rate-limiting enzyme in the biosynthesis of cholesterol, were screened. Inhibition rates of $10{\sim}15%$ were observed with hot water extracts of Allium fistulosum, Allium sativum and Cucurbita maxima. Methanol extracts of Aster scaber, Allium sativum, Zingiber officinale, Oenanthe javanica and Angelica keiskei effectively reduced the enzyme activity with inhibition rates of $29{\sim}51%$. The methanol extract of Angelica keiskei was fractionated sequentially with chloroform, ethyl acetate and n-butanol. Of the fractions ethyl acetate fraction showed the highest inhibition against the enzyme. $Luteolin-7-O-{\beta}-D-glucoside$ and hyperoside isolated from the ethyl acetate fraction of Angelica keiskei inhibited the enzyme activity by 65.5% and 14.8%, respectively, at the concentration of $30{\mu}M$.

• YAKHAK HOEJI
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• v.48 no.6
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• pp.328-334
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• 2004

Cervical cancer is one of the leading causes of female death. Viral oncoproteins E6 and E7 are selectively retained and expressed in carcinoma cells infected with HPV (Human pa pilloma virus) type 16 and cooperated in immotalization and transformation of primary keratinocyte. E6 and E7 oncoproteins interfere the functions of tumor suppressor proteins p53 and retinoblasoma protein (pRb), respectively. Among a lots of natural products, Mentha arvensis Linne var.piperascens have inhibitory effects on bindings between E6 oncoprotein and tumor suppressor p53, E3 ubiqutin- protein ligase (E6AP). HPV oncoprotein inhibitors from Mentha piperita L. were isolated by solvent partition and column chromatography (Silica gel, RP-18) and inhibitory compounds were finally purified by HPLC using an ELISA screening system based on binding between E6 and E6AP. The aim of this study is to identify the structure of inhibitory compounds and to investigate whether these compounds have inhibitory effects on functions of E6 oncoprotein. We investigated whether caffeic acid methyl ester (CAM) extracted from Mentha piperita L. could inhibit the function of E6 oncoprotein. CAM inhibited the in vitro binding of E6 and E6AP which are essential for the binding and degradation of the tumor suppressor p53 and also inhibited the proliferation of human cervical cancer cell lines (SiHa and CaSKi) in a dose response manner. These results suggest that CAM inhibited the function of E6 oncoprotein, suggesting that it can be used as a potential drug for the treatment of cervical cancers infected with HPV.

• Korean Chemical Engineering Research
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• v.44 no.5
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• pp.453-459
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• 2006

D-tryptophan and N-CBZ-D-phenylalanine were separated using ionic liquid as additives for the mobile phase in high performance liquid chromatography (HPLC). The ionic liquid of 1-butyl-3- methylimidazolium tetrafluoroborate (${[BMIm]}^+{[BF_4]}^-$) was used. Mobile phases were 65％, 70％, and 80％ methanol in water with addition of different concentrations (0.5, 1.0, 1.5, 2.0, 4.0, 6.0, 8.0, 10.0, 12.0, and 15.0 mmol/L) of the ionic liquid. The experiments were performed on stainless steel column, $3.9{\times}300mm$ i.d., packed with $15{\mu}m$ octadecyl-bonded silica gel at laboratory.The retention factor of D-tryptophan was not negligibly changed while that of N-CBZ-D-phenylalanine was decreased. The resolution between the two components were affected by the contents of methanol and ionic liquid in the mobile phase. With the small content of methanol and the high concentration of ionic liquid, the resolution was improved.

• YAKHAK HOEJI
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• v.54 no.6
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• pp.441-448
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• 2010

In present study, classification and quality control of Genus Polygonatum were developed using the isolated from Polygonati Odorati Rhizoma and Polygonati Rhizoma. 3 components were isolated from Butanol fractions of Polygonati Rhizoma, and 2 components were isolated from Hexane and Butanol fractions of Polygonati Odorati Rhizoma. All the components were obtained using silica gel and ODS column chromatography. The compounds were identified as adenosine, 14-hydroxylfurost-5-ene-3-O-${\beta}$-D-glucopyranosyl-($1{\rightarrow}2$)-O-${\beta}$-D-glucopyranosyl-($1{\rightarrow}4$)-O-${\beta}$-D-galactopyranosyl-26-O-${\beta}$-D-glucopyranoside, 22-O-methyl-14-hydrocxyfurost-5-ene-3-O-${\beta}$-D-glucopyranosyl-($1{\rightarrow}2$)-O-${\beta}$-D-glucopyranosyl-($1{\rightarrow}4$)-O-${\beta}$-Dgalactopyranosyl-26-O-${\beta}$-D-glucopyranoside, ${\beta}$-Sitosteryl-3-O-${\beta}$-D-D-glucopyranoside, 14-hydoxylfurost-5-ene-3-O-${\beta}$-Dglucopyranosyl-($1{\rightarrow}2$)-O-[${\beta}$-D-xylopyranosyl-($1{\rightarrow}3$)]-O-${\beta}$-D-glucopyranosyl-($1{\rightarrow}4$)-O-${\beta}$-D-galactopyranoside through physicochemical data, spectroscopic methods ($^1H$-NMR, $^{13}C$-NMR, Mass) according references. The quality control of genus Polygonatum were conducted using HPLC quantitative analysis of 14-hydroxylfurost-5-ene-3-O-${\beta}$-D-glucopyranosyl-($1{\rightarrow}2$)-O-${\beta}$-D-glucopyranosyl-($1{\beta}4$)-O-${\beta}$-D-galactopyranosyl-26-O-${\beta}$-D-glucopyranoside, 14-hydoxylfurost-5-ene-3-O-${\beta}$-D-glucopyranosyl-($1{\rightarrow}2$)-O-[${\beta}$-D-xylopyranosyl-($1{\rightarrow}3$)]-O-${\beta}$-D-glucopyranosyl-($1{\rightarrow}4$)-O-${\beta}$-D-galactopyranoside in 30 samples collected throughout Korea and China. This method provided a tool for standardization of mix or misusing the commercial Odorati Rhizoma and Polygonati Rhizoma. As a result, contained quantity of 14-hydroxylfurost-5-ene-3-O-${\beta}$-D-glucopyranosyl-($1{\rightarrow}2$)-O-${\beta}$-D-glucopyranosyl-($1{\rightarrow}4$)-O-${\beta}$-D-galactopyranosyl-26-O-${\beta}$-D-glucopyranoside was measured $0.008{\pm}0.006%$ and 14-hydoxylfurost-5-ene-3-O-${\beta}$-D-glucopyranosyl-($1{\rightarrow}2$)-O-[${\beta}$-D-xylopyranosyl-(13)]-O-${\beta}$-D-glucopyranosyl-($1{\rightarrow}4$)-O-${\beta}$-Dgalactopyranoside was measured $0.026{\pm}0.012%$.

• Natural Product Sciences
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• v.5 no.3
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• pp.113-120
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• 1999

Nitric oxide (NO) is a free radical synthesized from L-arginine by nitric oxide synthase (NOS). It is believed that NO is an important mediator in numerous physiological and inflammatory responses. Particularly, a large amount of NO released from the inducible nitric oxide synthase (iNOS) is mostly associated with inflammatory processes. Overproduction of NO in these processes including sepsis and autoimmune diseases can have deleterious consequences and pathophysiologic relevance. Therefore, for the discovery of new inhibitory agents against iNOS activity, we have evaluated about 100 kinds of natural products after partition into three layers (n-hexane, ethyl acetate and aqueous) from 100% methanol extracts to study inhibitory effects on iNOS activity induced by lipopolysaccharide (LPS) in RAW264.7 cells culture system. As a positive control, curcumin, which is known as an anti-tumor promoter, anti-inflammatory agent as an iNOS inhibitor, was used and showed the dose-dependent inhibitory effect $(IC_{50},\;2.5\;{\mu}g/ml)$. Among tested fractions, the n-hexane fraction of Cimicifuga heracleifolia $(IC_{50}:\;9.65\;{\mu}g/ml)$, Forsythiae fructus $(IC_{50}:\;6.36\;{\mu}g/ml)$, Saposhnikovia divaricata $(IC_{50}:\;5.92\;{\mu}g/ml)$, and the ethyl acetate fraction of Chrysanthemum sibiricum $(IC_{50}:\;2.56\;{\mu}g/ml)$, Gastrodia elata $(IC_{50}:\;3.46\;{\mu}g/ml)$, and the aqueous fraction of Dianthus chinensis $(IC_{50}:\;6.73\;{\mu}g/ml)$, Euonymus alatus $(IC_{50}:\;6.78\;{\mu}g/ml)$, Mechania urticifoloria $(IC_{50}:\;8.01\;{\mu}g/ml)$ showed strong inhibitory activity against LPS-stimulated iNOS. Especially, the ethyl acetate fraction of Chrysanthemum sibiricum $(IC_{50}:\;2.56\;{\mu}g/ml)$, which exhibited the strongest inhibition against iNOS, was fractionated with silica-gel column chromatography. These subfractions exhibited dose-dependent inhibition against iNOS activity in the range of $2.59-5.6\;{\mu}g/ml$ except for fraction No. 3, 4, 5, 6, 8, 9, and 16. Our study shows that Chrysanthemum sibiricum has the strongest inhibitory effect against iNOS activity and has similar effect to curcumin. Therefore, further studies for the identification of active principles from Chrysanthemum sibiricum and investigation for the mechanism of the inhibition of iNOS by active principles will be performed.