• Title/Summary/Keyword: Plant sterols

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Phytochemical Studies on Astragalus Root (3);Triterpenoids and Sterols (황기의 성분연구 (3);Triterpenoids and Sterols)

  • Jung, Hye-Sil;Lee, Eun-Ju;Lee, Je-Hyun;Kim, Ju-Sun;Kang, Sam-Sik
    • Korean Journal of Pharmacognosy
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    • v.39 no.3
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    • pp.186-193
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    • 2008
  • Astragali Radix, known as Huangqi, is the most important tonic in the traditional oriental medicine. It reinforces 'qi' (vital energy), strengthens the superficial resistance and promotes the discharge of pus and the growth of new tissue. It has long been used as an anti-perspirant, anti-diuretic or a tonic. Eleven compounds were isolated from the hexane and EtOAc fractions from the roots of Astragalus membranaceus (Leguminosae) and their structures were identified as four triterpenoids [lupenone (1), friedelin (2), lupeol (3), soyasapogenol E (9)] and seven sterols [${\beta}-sitosterol$ (4), stigmastane-3,6-dione (5), $7{\alpha}-hydroxysitosterol$ (6), $5{\alpha},6{\beta}-dihydroxysitosterol$ (7), $7-oxo-{\beta}-sitosterol$ (8), ${\beta}-sitosterol$ glucoside 6'-O-palmitate (10), ${\beta}-sitosterol$ glucoside (11)]. The chemical structures of these compounds were identified on the basis of spectroscopic methods and comparison with literature values. Among these compounds, lupenone (1), friedelin (2), lupeol (3), stigmastane-3,6-dione (5), $7{\alpha}-hydroxysitosterol$ (6), $5{\alpha},6{\beta}-dihydroxysitosterol$ (7), $7-oxo-{\beta}-sitosterol$ (8), soyasapogenol E (9), and ${\beta}-sitosterol$ glucoside 6'-O-palmitate (10) were isolated from this plant for the first time.

Stigmasterol isolated from marine microalgae Navicula incerta induces apoptosis in human hepatoma HepG2 cells

  • Kim, Young-Sang;Li, Xi-Feng;Kang, Kyong-Hwa;Ryu, BoMi;Kim, Se Kwon
    • 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.

Antioxidative Activities of Phenolic Compounds Isolated from Inonotus obliquus (차가버섯으로부터 분리한 페놀성 화합물의 항산화효과)

  • Kim, Hyoung-Ja;Jin, Chang-Bae;Lee, Yong-Sup
    • Korean Journal of Pharmacognosy
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    • v.38 no.2 s.149
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    • pp.164-169
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    • 2007
  • ln our continued search for biologically active compounds from traditional medicine, we found that ethyl acetate fraction from Inonotus obliquus showed potent antioxidant activities on three different cell-free bioassay systems. Bioassay-directed chromatographic fractionation of the ethyl acetate fraction from Inonotus obliquus afforded four phenolic compounds, 4-(3,4-dihydroxyphenyl)-(E)-3-buten-2-one (1) , 3,4-dihydroxybenzaldehyde (2), protocatechuic acid (3) and caffeic acid (4) along with three sterols such as lanosterol (5), ergosterol peroxide (6) and 9,11-dehydroergosterol peroxide (7). Among isolates, phenolic compounds (1-4) were assessed for antioxidant activities. Almost phenolic compounds showed potent DPPH and superoxide anion radicals scavenging and lipid peroxidation inhibitory activities indicating that these phenolic compounds contribute to the antioxidative activities of I. obliquus. Compounds 2-3 and 7 were isolated for the first time from this plant.

Phytochemical Studies on Lonicera Caulis (1) - Sterols and Triterpenoids (인동의 성분연구 (1) - Sterol 및 Triterpenoid 화합물)

  • Kim, Ju-Sun;Yean, Min-Hye;Lee, So-Young;Lee, Je-Hyun;Kang, Sam-Sik
    • Korean Journal of Pharmacognosy
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    • v.40 no.4
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    • pp.319-325
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    • 2009
  • Twelve compounds were isolated from the 70% ethanol extract of Lonicera Caulis (Caprifoliaceae) and their structures were identified as six triterpenoids [(24S)-cycloart-25-en-$3{\beta}$,24-diol (1), pomolic acid (7), ursolic acid (8), euscaphic acid (9), hederagenin (10), and 23-hydroxytormentic acid (12)] and six sterols [obtusifoliol (2), gramisterol (3), citrostadienol (4), ${\beta}$-sitosterol (5), ergosterol peroxide (6) and ${\beta}$-sitosterol glucoside (11)]. The chemical structures of these compounds were identified on the basis of spectroscopic methods and comparison with literature values. All the compounds were isolated from this plant parts for the first time.

Inhibitory Effect on TNF-${\alpha}$-Induced IL-8 Production in the HT29 Cell of Constituents from the Leaf and Stem of Weigela subsessilis

  • Thuong Phuong Thien;Jin WenYi;Lee JongPill;Seong RackSeon;Lee Young-Mi;Seong YeonHee;Song KyungSik;Bae KiHwan
    • Archives of Pharmacal Research
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    • v.28 no.10
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    • pp.1135-1141
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    • 2005
  • Twelve compounds were isolated from the MeOH extract of the leaf and stem of the Korean endemic plant Weigela subsessilis L. H. Bailey. Their chemical structures were elucidated on the basis of physicochemical and spectroscopic data and by comparison with those of published literatures. These compounds were identified as three sterols, ${\beta}$-sitosterol acetate (2), ${\beta}$-sitosterol (3), daucosterol (11), eight triterpenoids, squalene (1), ursolic acid (4), ilekudinol A (5), corosolic acid (6), ilekudinol B (7), esculentic acid (8), pomolic acid (9), asiatic acid (10), and one iridoid glycoside, alboside I (12). This is the first report pertaining to the isolation of these compounds from Weigela subsessilis L. H. Bailey. In addition, three compounds 7, 9, and 12 were found to display a strong inhibitory effect on the production of IL-8 in the HT29 cells stimulated by TNF-${\alpha}$.

Chemical Components of Dendrobium polyanthum

  • Hu, Jiang-Miao;Zhao, You-Xing;Miao, Ze-Hong;Zhou, Jun
    • Bulletin of the Korean Chemical Society
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    • v.30 no.9
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    • pp.2098-2100
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    • 2009
  • A new tetrahydroanthracene, 3,6,9-trihydroxy-3,4-dihydroanthracen-1(2H)-one (1), six phenolics, moscatilin (2), gigantol (3), batatasin (4), moscatin (5), 9,10-dihydromoscatin (6), 10-dihydrophenanthrene-2,4,7-triol (7), and a sesquiterpenoid, corchoionoside C (8), together with two sterols $\beta$-sitosterol (9) and daucosterol (10), were isolated from the stems of Dendrobium polyanthum. Compounds 1 and 2 were assessed for cytotoxic activity against two human tumor cell lines (A549 and HL-60).

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.

Development of Biologically Active Compounds from Edible Plant Sources XVIII. Isolation of Derivatives of Ergosterol from the Fruit Body of Phellinus linteus (식용 식물자원으로부터 활성물질의 탐색-XVIII. 상황버섯 (Phellinus linteus) 자실체로부터 Ergosterol 유도체의 분리)

  • Lyu, Ha-Na;Yoo, Jong-Su;Song, Myoung-Chong;Lee, Dae-Young;Kim, Dong-Hyun;Rho, Young-Duk;Kim, In-Ho;Baek, Nam-In
    • Applied Biological Chemistry
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    • v.50 no.1
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    • pp.57-62
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    • 2007
  • The fruiting body of Phellinus linteus was extracted with 80% aqueous MeOH, and the concentrated extract was partitioned with EtOAc, n-BuOH and $H_2$O. The repeated silica gel and ODS column chromatographies of the EtOAc fraction led to isolation of four sterols. From the result of spectral data including NMR, MS and IR, the chemical structures of the sterols were determined as ergosta-7,24(28)-dien-3${\beta}$-ol (episterol, 1), 5${\alpha}$,8${\alpha}$-epidioxyergosta-6,9(11),22-trien-3${\beta}$-ol (dehydrop-eroxyergosterol, 2), 5${\alpha}$,8${\alpha}$-epidioxyergosta-6,22-dien-3${\beta}$-ol (ergoterol peroxide, 3), and $3{\beta}$,$5{\alpha}$-dihydroxy-6${\beta}$-methoxyergosta-7,22-diene (6-O-methylcerevisterol, 4). The ergosterols have been first isolated from this mushroom in this study.

Chemical Constituents of Saposhnikovia divaricata (방풍의 화학 성분)

  • Kim, So-Jun;Chin, Young-Won;Yoon, Kee-Dong;Ryu, Min-Youl;Yang, Min-Hye;Lee, Je-Hyun;Kim, Jin-Woong
    • Korean Journal of Pharmacognosy
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    • v.39 no.4
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    • pp.357-364
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    • 2008
  • The roots of Saposhnikovia divaricata Schischk. (Umbelliferae) have been known to possess analgesic, anti-inflammatory, anti-parasitic and anti-bacterial activities, and used for curing headaches, fever and arthralgia. In this study, we aimed to isolate active constituents to provide phytochemical data for the quality control of this plant. Nine coumarins, eight chromones, three sterols and a coumarolignan were isolated from EtOAc-soluble fraction of the roots of S. divaricata through repetive column chromatography method using silica gel, ODS gel, Sephadex-LH 20, MPLC and HPLC. By analyses of spectroscopic data and comparison of their data with those of published values, the compounds were identified as 3'-O-angeloylhamaudol (1), ${\beta}$-sitosterol (2), marmesin (3), phellopterin (4), anomalin (5), imperatorin (6), xanthotoxin (7), deltoin (8), bergapten (9), stigmasterol (10), ledebouriellol (11), hamaudol (12), 8'-epicleomiscosin A (13), xanthoarnol (14), cimifugin (15), 5-O-methylvisamminol (16), daucosterol (17), 4'-O-${\beta}$-D-glucosyl-5-O-methylvisamminol (18), nodakenin (19), sec-O-glucosylhamaudol (20), prim-O-glucosylcimifugin (21). Among them, 8'-epicleomiscosin (13) was firstly reported from Umbelliferae family and xanthoarnol (14) and nodakenin (19) were isolated from this plant for the first time.

Isolation and Identification of Sterol Compounds from the Red Kohlrabi (Brassica oleracea var. gongylodes) Sprouts (적콜라비 (Brassica oleracea var. gongylodes) 새싹으로부터 sterol 화합물의 분리 및 동정)

  • Lee, Jae-Woong;Lee, Dae-Young;Cho, Jin-Gyeong;Baek, Nam-In;Lee, Youn-Hyung
    • Journal of Applied Biological Chemistry
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    • v.53 no.4
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    • pp.207-211
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    • 2010
  • The sprouts of Brassica oleracea var. gongylodes were extracted with 100% MeOH and the concentrated extract was partitioned with EtOAc, n-BuOH and $H_2O$, successively. From the EtOAc fraction, three sterols were isolated through the repeated silica gel and ODS column chromatographies. On the basis of physico-chemical and spectroscopic data including NMR, MS, and IR, the chemical structures of the sterols were determined as ${\beta}$-sitosterol (1), brassicasterol (2), and 7-ketobrassicasterol (3). Compound 1 is usually observed in plant. Compounds 2 is observed in Brassica sp., and compounds 3 have very rarely occurred in natural source including plant.