• Applied Biological Chemistry
• /
• v.48 no.1
• /
• pp.98-102
• /
• 2005

The MeOH extracts obtained from whole plant of Trigonotis peduncularis Benth. were solvent fractionated using EtOAc, n-BuOH and water, successively. The EtOAc and n-BuOH fractions gave four flavonol glycosides through application of silica gel and octadecyl silica gel (ODS) column chromatographies. The chemical structures of the flavonol glycosides were determined by the interpretation of several spectral data including 2D-NMR as $kaempferol-3-O-{\beta}-{D}-glucopyranoside\;(astragalin,\;1),\;kaempferol-3-O-{\alpha}-{L}-rhamnopyranosyl\;(1{\rightarrow}6)-{\beta}-{D}-glucopyranoside\;(nicotiflorin,\;2),\;quercetin-3-O-{\alpha}-{L}-rhamnopyranosyl(1{\rightarrow}6)-{\beta}-{D}-glucopyranoside\;(rutin,\;3),\;quercetin-3-O-{\beta}-{D}-glucopyranoside\;(isoquercitrin,\;4)$. The flavonoids have been first isolated from this plant. Nicotiflorin $(100\;{\mu}g/ml)$ showed $68.3{\pm}1.2%$ of the inhibitory effect on hACAT1(human Acyl CoA: cholesterol transferase 1) activity.

• Journal of Applied Biological Chemistry
• /
• v.54 no.1
• /
• pp.63-66
• /
• 2011

The bark of Machilus thunbergii was extracted with 80% aqueous methanol (MeOH), and the concentrated extract was partitioned using ethyl acetate (EtOAc), butanol (n-BuOH), and $H_2O$, successively. From the EtOAc fraction, five lignans were isolated through the repeated silica gel, octadecyl silica gel (ODS) and, Sephadex LH-20 column chromatography. Based on nuclear magnetic resonance (NMR), mass spectroscopy (MS), and infrared spectroscopy (IR) spectroscopic data, the chemical structures of the compounds were determined to be machilin A (1), machilin F (2), licarin A (3), nectandrin A (4), and nectandrin B, (5). This study presents comparative account of five lignans from M. thunbergii bark contributing inhibition of low density lipoprotein (LDL), ACAT-1, and ACAT-2. Compounds 2-5 showed varied degree of antioxidant activity on LDL with $IC_{50}$ values of 2.1, 11.8, 15.3, and $4.1{\mu}M$. Compounds 1, 2, and 3 showed inhibition activity on ACAT-1 with values $63.4{\pm}6.9%$ ($IC_{50}=66.8{\mu}M$), $53.7{\pm}0.9%$ ($IC_{50}=109.2{\mu}M$), and $78.7{\pm}0.2%$ ($IC_{50}=40.6{\mu}M$), respectively, at a concentration of 50 mg/mL, and on ACAT-2 with values $47.3{\pm}1.5%$ ($IC_{50}=149.7{\mu}M$), $39.2{\pm}0.2%$ ($IC_{50}=165.2{\mu}M$), and $52.1{\pm}1.0%$ ($IC_{50}=131.0{\mu}M$, respectively, at a concentration of 50 mg/mL.

• Applied Biological Chemistry
• /
• v.51 no.3
• /
• pp.223-227
• /
• 2008

The aerial parts of Sajabalssuk (Artemisia princeps PAMPANINI, Sajabalssuk) was extracted with 80% aqueous MeOH, and the concentrated extract was partitioned with EtOAc, n-BuOH and $H_2O$, successively. From the EtOAc fraction, three cycloartane-type triterpnoids and one ursane-type triterpenoid were isolated through the repeated silica gel, ODS and Sephadex LH-20 column chromatographies. From the results of physico-chemical data including NMR, MS and IR, the chemical structures of the triterpenoids were determined as wrightial (1), wrightial acetate (2), 27-norcycloart-20(21)-ene-25-al-3${\beta}$-ol acetate (3) and ursolic acid (4). No report has been found for isolation of compound 3 in the literature so far, and compounds 1, 2 and 3 were the first to be isolated from Sajabalssuk (Artemisia princeps PAMPANINI, Sajabalssuk). Also, compound 1 showed Acyl-CoA:Cholesterol acyltransferase (hACAT-1) and hACAT-2 inhibitory activity with the $IC_{50}$ values of 33.0 and 45.0 ${\mu}g/ml$, respectively. Compounds 2 and 3 inhibited hACAT-1 activity with the $IC_{50}$ values of 12.0 and 16.0 ${\mu}g/ml$, respectively.

• Archives of Pharmacal Research
• /
• v.28 no.5
• /
• pp.541-545
• /
• 2005

Flowers of Erigeron annuus L. were extracted with 80% aqueous MeOH, and the concentrated extract was partitioned with EtOAc, n-BuOH, and H$_2$O. Repeated silica gel and OD S column chromatography of the EtOAc fraction led to the isolation of a sterol, through activityguided fractionation, using ACAT inhibitory activity measurements. From the physico-chemical data, including NMR, MS, and IR, the chemical structure of the compound was determined to be an ergosterol peroxide (1), which has been isolated for the first time from this plant. This compound exhibited hACAT-1 and Lp-PLA$_2$ inhibitory effects, with inhibitory values of 51.6 ${\pm}$ 0.9 and 51 .7 ${\pm}$ 1.2%, at a treatment concentration of 0.23 mM.

• Food Science and Biotechnology
• /
• v.18 no.1
• /
• pp.95-102
• /
• 2009

The aerial parts of garland (Chrysanthemum coronarium L.) were extracted in 80% aqueous methanol (MeOH) and the concentrated extract was then partitioned using ethyl acetate (EtOAc), n-butanol (n-BuOH), and $H_2O$, successively. EtOAc and n-BuOH fractions resulted in 4 glycerides with the application of octadecyl silica gel and silica gel column chromatography. The chemical structures of the glycerides were determined using several spectroscopic methods, including nuclear magnetic resonance (NMR) and mass spectrometry (MS) as (2S)-1-O-palmitoyl-sn-glycerol (1), (2S)-1-O-oleoyl-2-O-oleoyl- 3-O-$\beta$-D-galactopyranosyl-sn-glycerol (2), (2S)-1-O-palmitoyl-2-O-linoleoyl-3-O-phosphorouscholine-sn-glycerol (3), and (2S)-1-O-linolenoyl-2-O-palmitoyl-3-O-[$\alpha$-D-galactopyrasyl-($1{\rightarrow}6$)-$\beta$-D-galactopyranosyl]-sn-glycerol (4). The free fatty acids of these glycerides were determined with gas chromatography (GC)-MS analysis following alkaline hydrolysis and methylation. These glycerides demonstrated an inhibitory effect on acyl-CoA: cholesterol acyltransferase (ACAT, compound 1: $45.6{\pm}0.2%$ at $100{\mu}g/mL$), diacylglycerol acyltransferase (DGAT, compound 1: $59.1{\pm}0.1%$ at $25{\mu}g/mL$), farnesyl protein transferase (FPTase, compound 2: $98.0{\pm}0.1%$; compound 3: $55.2{\pm}0.1%$ at $100{\mu}g/mL$), and $\beta$-secretase ($IC_{50}$, compound 4: $2.6{\mu}g/mL$) activity. This paper is the first report on the isolation of these glycerides from garland and their inhibitory activity on ACAT, DGAT, FPTase, and $\beta$-secretase.

• Archives of Pharmacal Research
• /
• v.28 no.5
• /
• pp.550-556
• /
• 2005

The flower of Campsis grandiflora K. Schum. Was extracted with 80% aqueous MeOH, and the concentrated extract was partitioned with EtOAc, n-BuOH and H$_2$O. From the EtO Ac fraction, seven triterpenoids were isolated through the repeated silica gel, ODS column chromatographies and preparative HPLC. From the result of physico- chemical data including NMR, MS and IR, the chemical structures of the compounds were determined as 3${\beta}$-hydroxyolean-12-en-28-oic acid (oleanolic acid, 1), 3${\beta}$-hydroxyurs-12-en-28-oic acid (ursolic acid, 2), 3${\beta}$-hydroxyurs-12-en-28-al (ursolic aldehyde, 3), 2${\alpha}$,3${\beta}$-dihydroxyolean-12-en-28-oic acid (maslinic acid, 4), 2${\alpha}$,3${\beta}$-dihydroxyurs-12-en-28-oic acid (corosolic acid, 5), 3${\beta}$,23-dihydroxyurs-12- en-28-oic acid (23-hydroxyursolic acid ,6) and 2${\alpha}$,3${\beta}$,23-trihydroxyolean-12-en-28- oic acid (arjunolic acid, 7). These teriterpenoids were isolated for the first time from this plant. Also, compounds 4, 5, 6, and 7 revealed relatively high hACAT-1 inhibitory activity with the value of 46.2${\pm}$1.1, 46.7${\pm}$0.9, 41.5${\pm}$1.3 and 60.8${\pm}$1.1% at the concentration of 100${\mu}$g/mL, respectively.

• Archives of Pharmacal Research
• /
• v.29 no.11
• /
• pp.937-941
• /
• 2006

Ixeris dentata forma albiflora was extracted with 80% aqueous MeOH, and the concentrated extract was partitioned with EtOAc, n-BuOH and $H_{2}O$. Eight sesquiterpenes were isolated through repeated silica gel and octadecyl silica gel ($C_{18},\;ODS$) column chromatography of the EtOAc and n-BuOH fractions. Physicochemical analysis using NMR, MS and IR revealed the chemical structures of the sesquiterpenes, which were zaluzanin (1), 9a-hydroxyguaian-4(15), 10(14), 11 (13)-triene-6, 12-olide(2), $3{\beta}-O-{\beta}-D-glucopyranosyl-8{\beta}-hydroxyguaian$-4(15), 10(14)-diene-6, 12-olide (3), $3-O-{\beta}-D-glucopyranosyl-8{\beta}-hydroxyguauan$-10(14)-ene-6, 12-olide (4), ixerin M (5), glucozaluzanin C (6), crepiside I (7), and ixerin D (8). This is the first time that these sesquiterpene lactones have been isolated from this plant. Compounds 1, 2 and 7 revealed relatively high cytotoxicities on human colon carcinoma cell and lung adeno-carcinoma cell, while compounds 5 and 7 showed acyl-CoA: cholesterol acyltransferase (ACAT) inhibitory activity.

• Applied Biological Chemistry
• /
• v.47 no.2
• /
• pp.251-257
• /
• 2004

The root of lxeris dentata forma albiflora was extracted with 80% aqueous MeOH and solvent fractionated with EtOAc, n-BuOH and water, successively. From the EtOAc and n-BuOH fractions, four sesquiterpene compounds were isolated through the repeated silica gel and ODS column chromatographies. The chemical structures were determined as zaluzanin C (1), $9{\alpha}-hydroxyguaian-4(l5),10(14),11(13)-triene-6,12-olide$ (2), $3{\beta}-O-{\beta}-D-glucopyranosyl-8{\alpha}-hydroxyguaian-4(15),10(14 )-diene-6,12-olide$ (3), and $3{\beta}-O-{\beta}- D-glucopyranosyl-8{\beta}hydroxyguaian-10(14)-ene-6,12-olide$ (4) through the interpretation of several spectral data including 2D-NMR. Some showed the inhibitory effects on DGAT (Diacylglycerol acyltransferase), ($IC_{50}$ values of 1, 2: 0.13, 0.10 mM), the catalyzing enzymes of the intracellular esterification of diacylglycerol and FPTase (Famesyl-protein transferase), ($IC_{50}$ values of 1, 2: 0.15, 0.18 mM), the farnesylation enzyme for Ras protein charge of cancer promotion.

• Food Science and Biotechnology
• /
• v.18 no.1
• /
• pp.223-227
• /
• 2009

The fruits of Cornus kousa Burg. were extracted with 80% aqueous methanol (MeOH) and the concentrated extract was partitioned with ethyl acetate (EtOAc), n-butanol (n-BuOH), and $H_2O$. From the EtOAc traction, 5 triterpenoids were isolated through repeated silica gel ($SiO_2$), octadecyl silica gel (ODS), and Sephadex LH-20 column chromatography (c.c.). These compounds were determined to be ursolic acid (1), corosolic acid (2), taraxasterol (3), betulinic acid (4), and betulinic aldehyde (5) on the basis of their spectroscopic data including electronic ionization mass spectrometry, ultraviolet spectroscopy, infrared spectroscopy, and nuclear magnetic resonance. This is the first reported isolation of these compounds from this plant. Also, compounds 1, 3, 4, and 5 show a relatively high inhibitory activity against human acyl-CoA: cholesterol acyltransferase-1 (hACAT-1) with inhibition values of $52.8{\pm}0.7$, $91.1{\pm}0.4$, $93.0{\pm}0.7$, and $96.2{\pm}0.2%$ at a concentration of $100{\mu}M$, respectively.