• Title/Summary/Keyword: stigmasterol 3-O-$\beta$-D-glucopyranoside

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Sterols from the Seed of Cowpea (Vigna sinensis K.) (동부로부터 sterol의 분리 동정)

  • Cui, En-Ji;Park, Hee-Jung;Wu, Qian;Chung, In-Sik;Kim, Ji-Young;Baek, Nam-In
    • 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.

Constituents of the Halophyte Salicornia herbacea

  • Lee, Yeon-Sil;Lee, Hye-Seung;Shin, Kuk-Hyun;Kim, Bak-Kwang;Lee , Sang-Hyun
    • Archives of Pharmacal Research
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    • v.27 no.10
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    • pp.1034-1036
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    • 2004
  • Four compounds were isolated from Salicornia herbacea by repeated column chromatography. Their structures were identified as ${\beta}$-sitosterol (1), stigmasterol (2), uracil (3), and isorhamnetin-3-O-${\beta}$-D-glucopyranoside (4) by spectral analysis and comparison with the published data.

Chemical Constituents of Gomphrena globosa. II

  • Dinda, Biswanath;Ghosh, Biplab;Achari, Basudev;Arima, Shiho;Sato, Nariko;Harigaya, Yoshihiro
    • Natural Product Sciences
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    • v.12 no.2
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    • pp.89-93
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    • 2006
  • One new sterol glucoside, $gomphsterol\;{\beta}-D-glucoside$ 1 along with known compounds, ${\beta}-sitosterol$, stigmasterol, campesterol, $stigmasterol-{\beta}-D-glucoside$, friedelin, 3-epi-friedelinol, allantoin, and $chrysoeriol-7-O-{\beta}-D-glucoside$ have been isolated from the aerial parts of Gomphrena globosa (Amaranthaceae). On the basis of spectroscopic (including 2D NMR) and chemical studies, the structure of 1 was elucidated as $(22E,24S)-24-ethylcholesta-7,9(11),22-trien-3{\beta}-ol-3-O-{\beta}-D-glucopyranoside$. Known compounds are reported for the first time from this plant species.

Chemical constituents of Synurus deltoides (Aiton)Nakai

  • Lee, Hyun-Yong;Jin, Wen-Yi;An, Ren-Bo;Na, Min-Kyun;Bae, Ki-Hwan
    • Proceedings of the PSK Conference
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    • 2002.10a
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    • pp.375.2-375.2
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    • 2002
  • S.deltoides (Compositae) distributed widely in Korea. China. It is edible as a food additive. but there has been no study on chemical constituents. Therefore. we isolated nine compounds from S.deltoldes. On the basis of spectroscopic evidence. the structure of these compounds were characterized as lupeol( 1), $\alpha$-amyrin(2).$\beta$-amyrin (3), ursolic acid(4), nonacosanol(5), nonacosanoic acid(6). mixture of $\beta$-sitosterol. stigmasterol and campesterol (7), $\beta$-sitosteryl-3-O-$\beta$-D-glucopyranoside(8), stigmasteryI-3-O-$\beta$-D-glucopyranoside(9). (omitted)

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Steroids from the Aerial Parts of Artemisia princeps Pampanini

  • Yoo, Jong-Su;Ahn, Eun-Mi;Bang, Myun-Ho;Song, Myoung-Chong;Yang, Hye-Joung;Kim, Dong-Hyun;Lee, Dae-Young;Chung, Hae-Gon;Jeong, Tae-Sook;Lee, Kyung-Tae;Choi, Myung-Sook;Baek, Nam-In
    • Korean Journal of Medicinal Crop Science
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    • v.14 no.5
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    • pp.273-277
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    • 2006
  • Three stigmastane-type sterols and one ergostane-type sterol were isolated from the ethyl acetate soluble fraction of the aerial parts of Artemisia princeps Pampanini (Sajuarissuk). From the results of physico-chemical data including NMR, MS and IR, the chemical structures of the compounds were determined as $stigmasta-5,22-dien-3,{\beta}-ol (stigmasterol, 1),stigmast-5-en-3{\beta}-ol({\beta}-sitosterol,2), 5{\beta},8{\beta}-epidioxy-5{\beta},8{\beta}-ergosta-6,22-dien-3{\beta}-ol(ergosterol peroxide, 3),\;and\;{\beta}-sitosterol\;3-O-{\beta}D-glucopyranoside(daucosterol,4)$.

Chemical Constituents from the Aerial Parts of Abutilon theophrasti (어저귀 지상부의 화학성분)

  • Jin, Qinglong;Ko, Hae Ju;Chang, Young-Su;Woo, Eun-Rhan
    • Korean Journal of Pharmacognosy
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    • v.46 no.2
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    • pp.93-98
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    • 2015
  • Eleven compounds, lupenone (1), lupeol (2), stigmasterol (3), β-sitosterol (4), 24-methylene-3,4-seco-cycloart-4(28)-en-3-oic acid (5), 24-methylene-3,4-seco-cycloart-4(28)-en-3-methyl ester (6), (+)-(1S,4R)-7-hydroxycalamenene (7), hibicuslide C (8), isopropyl-${\beta}$-D-glucopyranoside (9), syringaresinol-4'-O-${\beta}$-D-glucoside (10), and rutin (11) were isolated from the aerial parts of Abutilon theophrasti. The chemical structures of compounds 1-11 were determined by the basis of physicochemical properties and spectroscopic methods such as 1D and 2D NMR. These compounds were isolated from this plant for the first time. In addition, compounds 6 and 9 were obtained for the first time as natural products not as synthetics.

Phytochemical Constituents from the Leaves of Soybean [Glycine max (L.) Merr.]

  • Lee, Jin-Hwan;Baek, In-Youl;Choung, Myoung-Gun;Ha, Tae-Joung;Han, Won-Young;Cho, Kye-Man;Ko, Jong-Min;Jeong, Seong-Hun;Oh, Ki-Won;Park, Keum-Yong;Park, Ki-Hun
    • Food Science and Biotechnology
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    • v.17 no.3
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    • pp.578-586
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    • 2008
  • Phytochemicals study from the leaves of soybean [Glycine max (L.) Merr.], one of Korean edible plant materials were investigated through various chromatographic procedures. The methanolic leaves extracts of soybean yielded 16 phytochemicals, including 5 isoflavones 1-5, 3 flavones 6-8, 1 flavonol 9, 2 pterocarpans 10 and 11, 2 phenolic compounds 12 and 13, 2 phytosterols 14 and 15, and 1 sugar alcohol 16. The structures were fully characterized by analysis of physical and spectral data and were defined clearly as 4,5,7-trihydroxyisoflavone (1), 4,5,7-trihydroxyisoflavone-7-O-$\beta$-D-glucopyranoside (2), 4,7-dihydroxy-6-methoxyisoflavone (3), 4,7-dihydroxyisoflavone (4), 4,7-dihydroxyisoflavone-7-O-$\beta$-D-glucopyranoside (5), 5,7,4'-trihydroxyflavone (6), 3',4',5,7-tetrahydroxyflavone (7), 3',4',5-trihydroxyflavone-7-O-$\beta$-D-glucopyranoside (8), 3,4',5,7-tetrahydroxyflavonol (9), coumestrol (10), glyceofuran (11), 4-hydroxybenzoic acid (12), methyl-4-hydroxybenzoate (13), soyasapogenol B (14), stigmasterol (15), and D-mannitol (16), respectively. Among them, phytochemicals 7-16 were reported for the first time on the isolation and confirmation from the leaves of this species. These results suggest that the leaves extracts of soybean may possess possible health related benefits to human due to the isolated phytochemicals 1-16 which have been well known potential effects on various chronic diseases.