• Journal of Physiology & Pathology in Korean Medicine
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• v.21 no.1
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• pp.70-75
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• 2007

In the present study, we has been isolated the anti-cariogenic component, stigmasterol, from Aralia continentalis (A. continentalis) and identified by MS, $^1$H-NMR and $^{13}$C-NMR and also investigated the anti-cariogenic properties of stigmasterol. The methanol extract of ,A. continentalis showed concentration-dependent inhibitory activity against the growth and acid production of S. mutans. The MeOH extract was suspended in H$_2$O and sequentially partitioned with n-hexane, CHCl$_3$, EtOAc, and n-BuOH. The CHCl$_3$ fraction showed remarkable antibacterial activity against S. mutans. The anti-cariogenic compound, stigmasterol, has been isolated successively through the screening system and various chromatography methods. Anti-cariogenic properties of stigmasterol were also investigated. From this active chloroform subfraction, isolation and identification finally gave (24E)-stigmasta-5,22-dien-3${\beta}$-ol (stigmasterol) {[a]$_D\;^{25}$ -48.33$^{\circ}C$(C 0.28, CHCl$_3$)} by spectroscopic methods (MS, $^1$H-NMR and $^{13}$C-NMR) as an active principle. The compound, stigmasterol, showed significant growth, acid production, adhesion and water-insoluble glucan synthesis inhibitory effect against S. mutans. These results suggest that stigmasterol from ,A. continentalis may inhibit cariogenic properties of S. mutans and these properties may provide some scientific rationales that the local inhabitants used the extracts for treatment of dental diseases.

• BMB Reports
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• v.47 no.8
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• pp.433-438
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• 2014

Plant sterols have shown potent anti-proliferative effects and apoptosis induction against breast and prostate cancers. However, the effect of sterols against hepatic cancer has not been investigated. In the present study, we assessed whether the stigmasterol isolated from Navicula incerta possesses apoptosis inductive effect in hepatocarcimona (HepG2) cells. According to the results, Stigmasterol has up-regulated the expression of pro-apoptotic gene expressions (Bax, p53) while down-regulating the anti-apoptotic genes (Bcl-2). Probably via mitochondrial apoptosis signaling pathway. With the induction of apoptosis caspase-8, 9 were activated. The DNA damage and increase in apoptotic cell numbers were observed through Hoechst staining, annexin V staining and cell cycle analysis. According to these results, we can suggest that the stigmasterol shows potent apoptosis inductive effects and has the potential to be tested as an anti-cancer therapeutic against liver cancer.

• Natural Product Sciences
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• v.2 no.1
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• pp.19-23
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• 1996

A mixture of sterols containing ${\beta}-sitosterol$ and stigmasterol (1), and sterol glycosides containing $3-O-{\beta}-D-glucopyranosyl$ ${\beta}-sitosterol$ and $3-O-{\beta}-D-glucopyranosyl$ stigmasterol (2) were isolated from the leaves of Gynura procumbens. After acetylation of 2 with pyridine-acetic anhydride, $3-0-{\beta}-D-tetra-O-acetylglucopyranosyl$ ${\beta}>-sitosterol$ (3) was isolated.

• KSBB Journal
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• v.16 no.1
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• pp.76-81
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• 2001

Stigmastanol, a functional agent of cholesterol-lowering in humans, was synthesized from stigmasterol. To investigate the usability as a raw material, the contents of sterol in vegetable oils and extract of soybean chaff were analyzed. The total sterol contents showed high values of 213.7 and 209.8 mg/100g in corn and soybean oils respectively. The extract of soybean chaff has played a good role as a raw material with high sterol contents. The kinetics of hydrogenation of stigmasterol was studied using a 5% Pd/AC catalyst in the temperature range of 30~$60^{\circ}$C. Increasing temperature showed a prominent decrease in conversion. The optimum temperature was $40^{\circ}$C for high yield of stigmastanol. The effects of $H_2$ pressure, agitation speed, catalyst loading, and stigmasterol concentration on reaction rate profile were also examined. From the power law model analysis using the initial rates of reaction, the reaction order was calculated as 0.705 for stigmasterol concentration and 0.147 for hydrogen pressure.

• Applied Biological Chemistry
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• v.51 no.1
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• pp.60-64
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• 2008

The aerial parts of Spathiphyllum cannifolium were extracted with 80% aqueous MeOH and the concentrated extract was partitioned with EtOAc, n-BuOH and $H_2O$, successively. From the EtOAc fraction, three compounds were isolated through the repeated silica gel, ODS, Sephadex LH-20 column chromatographies. From the results of physico-chemical data including NMR, MS and IR, the chemical structures of the compounds were determined as stigmasterol (1), $(2S)1-O-linolenoyl-2-0-myristoyl-3-0-{\beta}-D-galactopyranosyl-sn-glycerol$ (2) and stigmasterol glucoside (3). They were the first to be isolated from Spathiphyllum cannifolium.

• Journal of Applied Biological Chemistry
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• v.53 no.2
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• pp.77-81
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• 2010

The seed of cowpea (Vigna sinensis K.) was extracted with 80% aqueous methanol (MeOH). And the concentrated extract was partitioned with ethyl acetate (EtOAc), n-butanol (n-BuOH) and $H_2O$, successively. The repeated silica gel and octadecyl silica gel (ODS) column chromatographic separations for the EtOAc and n-BuOH fractions led to isolation of four sterols. And the chemical structures of the compounds were determined as a mixture of stigmasterol and $\beta$-sitosterol with the ratio of 4 to 3 (1), 7-ketositosterol (2), and stigmasterol 3-O-$\beta$D-glucopyranoside (3) from the interpretation of spectroscopic data including nuclear magnetic resonance (NMR) spectrum metric, mass (MS) spectrum metric and infrared (IR) spectroscope. This study reports the first isolation of $\beta$-sitosterol, 7-ketositosterol, and stigmasterol 3-O-$\beta$-D-glucopyranoside from the seed of Vigna sinensis K. In addition, compound 2, 7-ketositosterol, is rarely occurred in natural source including plant.

• Korean Journal of Food Science and Technology
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• v.52 no.2
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• pp.200-203
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• 2020

The effect of stigmasterol (SS), a phytosterol, in the liposome bilayer on the stability of encapsulated ascorbic acid (ASA) was evaluated. Liposomes, consisting of phosphatidylcholine (PC) and SS, and ASA were encapsulated by the dehydration/rehydration method. The average particle size of the liposome increased with increasing SS content. SS significantly increased the stability of encapsulated ASA. For example, ASA remaining in the liposomes of 100:0, 90:10, and 70:30 (PC:SS, w/w) ratios was 34.12%, 49.88%, and 58.58%, respectively, after storage for 8 days at 4℃, while only 7.66% ASA remained in the buffer under the same conditions. These results indicated that SS in liposomes increased the stability of encapsulated ASA.

• KOREAN JOURNAL OF CROP SCIENCE
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• v.64 no.1
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• pp.25-32
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• 2019

This study was carried out to investigate the changes in fatty acid composition and phytosterol content of the autumn sowing waxy corn during its ripening period for the production of high quality and value-added fresh ears. The content of crude oil in the waxy corn kernels steadily increased with days after pollination(DAP); the crude oil content in Heukjinjuchal (HC) was higher than that in Ilmichal (IC). The composition of fatty acids according to DAP showed a statistically significant change; palmitic and linoleic acid composition gradually decreased, but oleic acid increased, and the composition of unsaturated fatty acids in HC was higher than that in IC. The phytosterol content was increased until 33 DAP, and was 937.7 mg/100g and 867.9 mg/100g in IC and HC, respectively, but there was no statistically significant difference between the varieties. The phytosterol contents in IC varied in the following order: ${\beta}-sitosterol$ > stigmasterol > campesterol, but that in HC varied in the order ${\beta}-sitosterol$ > campesterol > stigmasterol. The campesterol content did not show significant differences between the varieties, but the stigmasterol and ${\beta}-sitosterol$ content was significantly higher in HC than in IC. Palmitic, linolieic, and linolenic acid were significantly correlated with campesterol and ${\beta}-sitosterol$, and stearic acid was positively correlated with stigmasterol. Oleic acid was positively correlated with campesterol and ${\beta}-sitosterol$ but negatively correlated with stigmasterol. As a result, it was suggested that fatty acids may affect the variation in phytosterol contents during the ripening period in waxy corn.

• KOREAN JOURNAL OF CROP SCIENCE
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• v.63 no.2
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• pp.131-139
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• 2018

Unsaponifiables in the kernel and the cob of 7 maize varieties were analyzed by using thin-layer chromatography (TLC) and gas chromatography (GC) for the identification of phytosterols and their concentrations. The unsaponifiables of the kernel were clearly separated into band I (campesterol, stigmasterol, and ${\beta}$-sitosterol), band II (${\Delta}^5$-avenasterol), band III (${\Delta}^7$- stigmastenol), and band IV (${\Delta}^7$-avenasterol). In the cob, on the other hand, three or more bands were separated in addition to bands. The GC analysis of unsaponifiables showed good separation of campesterol, stigmasterol and ${\beta}$-sitosterol, but the mixture of ${\Delta}^7$-avenasterol (retention time[RT] 22.846), ${\Delta}^7$-stigmastenol (RT 22.852), and ${\Delta}^5$-avenasterol (RT 22.862) showed poor separation. Phytosterol content of the maize kernel was 635.9 mg/100 g, and that of the cob was 273.0 mg/100 g, respectively. The phytosterol content of the kernel was 2.4-fold higher than that of the cob. The phytosterol content of the kernel was higher in the order ${\beta}$sitosterol 80.05% > campesterol 10.5% > stigmasterol 9.46%, but that of the cob was higher in the order ${\beta}$-sitosterol 59.43% > stigmasterol 31.72% > campesterol 10.98%. Based on these results, it appears that the phytosterols of the maize kernel are synthesized in the maize cob and are transferred to the kernel, because the precursors (${\Delta}^7$-avenasterol, ${\Delta}^7$-stigmastenol, and ${\Delta}^5$-avenasterol) of major phytosterols were detected in maize cobs.

• Analytical Science and Technology
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• v.22 no.3
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• pp.219-227
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• 2009

The steroid compounds in Rhodiola sachalinensis were determined with adsorption column chromatographic purification and GC/MS. Sterols were extracted by sonication and Soxhlet with ethanol and dichloromethane, respectively. The extract was partitioned with chloroform and water using liquid-liquid extraction, and purified with a silica column after the sterols had been converted to the corresponding silyl derivatives with BSTFA. Eighteen free sterols, including $\beta$-sitosterol, stigmasterol and cycloartenol, and nine sterol conjugates were found from Rhodiola sachalinensis by GC/MS. Among them, cholest-5-ene-3-ol, cholesterol, stigmasterol, $\beta$-sitosterol were confirmed and quantified with sterol standards. Most sterols were presented in the chloroform part, with $C_{29}$ being the most abundant group in this sterol group. $\beta$-sitosterol was the most abundant compound with a relative content of 45.94% followed by ergost-7-ene-3-ol (11.33%), 4,14-dimethyl-ergosta-8,24(28)-diene-3-ol (7.07%), stigmasterol (6.09%), cycloartenol (5.43%) and 4-methyl-cholest-5-ene-3-ol (5.39%).