• Natural Product Sciences
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• 제2권1호
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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.

• 약학회지
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• 제44권4호
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• pp.334-339
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• 2000

The present study was carried out to evaluate biologically active components of the rhizomes of Sparganium stoloniferum and to supply the preliminary data for the chemotaxonomy and the medicinal application. Extraction and systematic fractionation of the rhizomes by column chromatography led to the isolation of six compounds from ethylacetate and n-butanol soluble fractions. Elucidation of the chemical structures of these compounds by physicochemical and apectral analysis demonstrated that compound I,II ,III,IV,V and Ⅵ were $\beta$-sitosterol, $\beta$-sitosterol-3-$\beta$-D-glucuronopyranoside, 3- (4-hydroxyphenyl)-2-propenoic acid, sorbose, 1-O-$\beta$-D-glucopyranosyl-(2S, 3R, 4E, 8Z)-2-[(2(R)-hydroxyeicosanoyl)amido]-4,8-octadecadiene-1,3-diol, and $\beta$-sitosterol-3-O-$\beta$-D-glucopyranoside, respectively.

• 한국식품과학회지
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• 제45권5호
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• pp.557-564
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• 2013

본 연구에서는 배의 유용성 증명을 위한 일환으로 배의 화학성분을 분자수준에서 밝히고자 하였다. 이에 배 과피 MeOH 추출물을 용매분획하여 얻은 EtOAc-산성 분획과 EtOAc-중성분획을 대상으로 Sephadex LH-20, silica gel, 그리고 ODS colmn chromatography와 HPLC를 이용하여 정제 및 단리하였다. 그 결과, EtOAc-산성 분획과 EtOAc-중성 분획으로부터 각각 2종씩의 화합물을 단리하였다. 단리된 화합물 1-4는 $^1H$- 및 $^{13}C$-NMR 분석을 통하여 각각 (S)-(+)-2-cis-abscisic acid O-${\beta}$-D-glucopyranosyl ester (화합물 1), 1-[4-O-${\beta}$-D-glucopyranosyl]phenyl ethanone (piceoside, 화합물 2), ${\beta}$-sitosterol (화합물 3), 그리고 ${\beta}$-sitosteryl 3-O-${\beta}$-D-glucopyranoside (화합물 4)로 동정되었다. 단리된 3종의 배당체 화합물(화합물 1, 2, 4)들은 본 연구에 의해 배로부터 처음 동정되었으며, 화합물 3은 추황배로부터 처음 동정되었다. 본 연구결과가 배 함유 성분연구는 물론 배의 기능성 해명 연구에도 추후 중요한 기초자료로 활용되길 기대한다.

• Archives of Pharmacal Research
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• 제16권2호
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• pp.104-108
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• 1993

From the root barks of Araila elata Seem.(Araliaceae) three known saponins together with oleanolic acid and $\beta$-sitosterol $3-O-\beta$-D-glucoside were isolated. The saponins were identified as oleanolic acid $28-O-\beta$-D-glucoside were isolated. The saponins were identified as oleanolic acid $28-O-\beta$-D-glucopyranosyl ester, oleanolic acid $3-O-\beta$-D-glucuronopyranoside and oleanolic acid $3-O-\alpha$-L-arabinofuranoysyl-(1$\rightarrow$4)-$\beta$-D-glucuronopyranoside(narcissiflo on the basis of chemical and spectra data. The latter two saponins were isolated as their dimethylesters as well as monomethylesters.

• Natural Product Sciences
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• 제14권3호
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• pp.161-166
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• 2008

A mixture of sixteen cerebrosides, which comprised four cerebroside molecular species (PL-1 ${\sim}$ PL-4) was separated from the roots of Paeonia lactiflora. The structures of cerebrosides were characterized as $1-O-{\beta}$-D-glucopyranosides of phytosphingosines, which comprised a common long-chain base, (2S,3S,4R,8E/Z)-2-amino-8-octadecene-1,3,4-triol with eight fatty acids or 2-hydroxy fatty acids of varying chain lengths ($C_{16}$, $C_{18}$, $C_{20-26}$) linked to the amino group. Aralia cerebroside and its 8Z isomer (PL-1), $1-O-{\beta}$-D-glucopyranosyl-(2S,3S, 4R,8E/Z)-2-[(2'R)-2'-hydroxytetracosanoylamino]-8-octadecene-1,3,4-triol (PL-2), $1-O-{\beta}$-D-glucopyranosyl-(2S,3S,4R, 8E/Z)-2-[(2'R)-2'-hydroxydocosanoylamino]-8-octadecene-1,3,4-triol (PL-3), and $1-O-{\beta}$-D-glucopyranosyl-(2S,3S,4R, 8E/Z)-2-[(2'R)-2'-hydroxytricosanoylamino]-8-octadecene-1,3,4-triol (PL-4) were identified as major components of these cerebroside molecular species. All the major cerebrosides were shown to be a mixture of geometrical isomers (8E and 8Z) of phytosphingosine-type glucocerebrosides possessing 2R-hydroxy fatty acids. In addition, three ${\beta}-sitosterol$ derivatives and adenosine were also separated. The structures of these isolates have been determined on the basis of chemical and spectroscopic evidence.

• Natural Product Sciences
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• 제17권4호
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• pp.350-353
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• 2011

A new daucosteryl derivative, verticilloside (1), was isolated from the seeds of Malva verticillata L. (Malvaceae). The structure was determined to be 3-O-[${\beta}$-D-(6'-linoleoyl)glucopyranosyl]-${\beta}$-sitosterol based on spectroscopic analyses ($^1H$ and $^{13}C$-NMR, DEPT, COSY, HMQC, and HMBC) and chemical reactions.

• 생약학회지
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• 제26권2호
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• pp.130-138
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• 1995

Phytochemical study on the aerial parts of Solanum lyratum (Solanaceae) was carried out. On the basis of phytochemical and spectroscopic evidences, compound I was identified as mixtures of hexadecanoic acid methyl ester, 2,6,10,15-tetramethyl heptadecane, tricosane, tetracosane, pentacosane, docosanoic acid methyl ester, docosane, tricosanoic acid methyl ester, 8-hexyl pentadecane, tetracosanoic acid methyl ester, pentatriacontane, hexatriacontane, eicosane, hexacosane, hentriacontane and stigmasta-5,23-dien $3-{\beta}-ol$, and compound II, III, IV and V were identified as hexacosanoic acid methyl ester, ${\beta}-sitosterol-{\beta}-{_D}-glucoside$, $3-O-{\alpha}-{_L}-rhamnopyranosyl-(1->2)-{\beta}-{_D}-glucuronopyranosyl$ diosgenin and $3-O-{\alpha}-{_L}-rhamnopyranosyl-(1->6)-{\beta}-{_D}-glucopyranosyl$ quercetin (rutin), respectively. Rutin was identified as one of the active principles having antioxidative effect from S. lyratum.

• Natural Product Sciences
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• 제24권2호
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• pp.132-138
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• 2018

Phytochemical investigation of 80% MeOH extract of the aerial parts of Capsella bursa-pastoris yielded fourteen compounds (1 - 14). The structures of the compounds were elucidated by spectroscopic methods to be methyl-1-thio-${\beta}$-D-glucopyranosyl disulfide (1), 10-methylsulphinyl-decanenitrile (2), 11-methyl-sulphinyl-undecanenitrile (3), 1-O-(lauroyl)glycerol (4), phytene-1, 2-diol (5), (3S,5R,6S,7E)-5,6-epoxy-3-hydroxy-7-megastigmen-9-one (6), loliolide (7), ${\beta}$-sitosterol (8), 3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-1-propanone (9), 1-feruloyl-${\beta}$-D-glucopyranoside (10), pinoresinol-4'-O-${\beta}$-D-glucopyranoside (11), luteolin (12), quercetin-3-O-${\beta}$-D-glucopyranoside (13), and luteolin 6-C-${\beta}$-glucopyranoside (14). Although compound 1 was reported as synthetic compound, 1 was first isolated from natural source. NMR spectral data assignments of 1, 2 and 3 were reported for the first time, and compounds 1 - 14 were for the first time reported from this plant source. The anti-inflammatory effects of 1 - 14 were evaluated in lipopolysaccharide (LPS)-stimulated murine microglia BV-2 cells. Compounds 12 exhibited strong inhibitory effects on nitric oxide production in LPS-activated BV-2 cells with $IC_{50}$ values of $9.70{\mu}M$.

• Archives of Pharmacal Research
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• 제29권12호
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• pp.1074-1079
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• 2006

As part of our research on phytochemicals that exert protective effects against diseases related to reactive nitrogen species, we have evaluated the scavenging activity of the yellow leaves of Ginkgo biloba on $ONOO^{-}$. The methanol extract and ethyl acetate fraction obtained from yellow leaves of G. biloba evidenced a marked scavenging activity on authentic $ONOO^{-}$. Repeated column chromatography of the active ethyl acetate soluble fraction on silica gel, Sephadex LH-20, and RP-18, resulted in the purification of 15 known compounds, including sciadopitysin (1), ginkgolide B (2), bilobalide (3), isoginkgetin (4), kaempferol (5), luteolin (6), protocatechuic acid (7), bilobetin (8), amentoflavone (9), ${\beta}-sitosterol$ glucopyranoside (10), kaempferol 3-O-rhamnopyranoside (11), kaempferol 3-O-glucopyranoside (12), kaempferol $3-O-[{6^{'}-O-p-coumaroyl-{\beta}-D-glucopyranosyl(1{\rightarrow}2)-{\alpha}-L-rhamnopyranoside]$ (13), kaempferol 3-O-rutinoside (14), and 6-hydroxykynurenic acid (15). Among the compounds isolated, flavonoids (5, 6 and 11-14), protocatechuic acid (7), and 6-hydroxykynurenic acid (15) all exhibited marked scavenging activities on authentic $ONOO^{-}$. The $IC_{50}$ values of 5-7, 11-14 and 15 were as follows: $2.86{\pm}0.70,\;2.30{\pm}0.04,\;2.85{\pm}0.10,\;5.60{\pm}0.47,\;4.16{\pm}1.65,\;2.47{\pm}0.15,\;3.02{\pm}0.48,\;and\;6.24{\pm}0.27\;{\mu}M$, respectively. DL-Penicillamine ($IC_{50}=4.98{\pm}0.27\;{\mu}M$) was utilized as a positive control. However, the other compounds (1-4, 8-10) exerted no effects against $ONOO^{-}$.

• Natural Product Sciences
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• 제26권3호
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• pp.214-220
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• 2020

Brassica oleracea var. gongylodes (red kohlrabi) is a biennial herbaceous vegetable whose edible bulbotuber-like stem and leaves are consumed globally. Sliced red kohlrabi tubers were extracted using methanol and the concentrated extract was partitioned successively with dichloromethane (CH₂Cl₂), ethyl acetate (EtOAc), n-butanol (n-BuOH) and water (H₂O). Repeated column chromatography of EtOAc fraction through silica, sephadex LH-20 and RP-18 gel led to isolation of eleven compounds of which compound 1 was a new glycosylated indole alkaloid derivative, 1-methoxyindole 3-carboxylic acid 6-O-β-D-glucopyranoside. Others were known compounds namely, β-sitosterol glucoside (4), 5-hydroxymethyl-2-furaldehyde (5), methyl-1-thio-β-D-glucopyranosyl disulfide (6), 5-hydroxy-2-pyridinemethanol (7), (3S,4R)-2-deoxyribonolactone (8), n-butyl-β-D-fructopyranoside (9), uridine (10) and three fructose derivatives, D-tagatose (11), β-D-fructofuranose (12) and β-D-fructopyranose (13). Similarly, isolation from CH₂Cl₂ fraction gave two known indole alkaloids, indole 3-acetonitrile (2) and N-methoxyindole 3-acetonitrile (3). The structure elucidation and identification of these compounds were conducted with the help of ¹³C and ¹H NMR, HMBC, HMQC, EIMS, HR-ESIMS and IR spectroscopic data, and TLC plate spots visualization. Compounds 2, 3, 4, 5, 6, 7, 8 and 9 are noted to occur in kohlrabi for the first time. Different bioactivities of these isolated compounds have been reported in literature.