• Title/Summary/Keyword: cerebroside

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Phytochemical Studies on Paeoniae Radix (4);Cerebrosides and Other Constituents

  • Kim, Yoon-Jung;Yean, Min-Hye;Lee, Eun-Ju;Kim, Ju-Sun;Lee, Je-Hyun;Kang, Sam-Sik
    • Natural Product Sciences
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    • v.14 no.3
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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.

Some Peroxysterols and Ceramides from "Phellinus ribis", a Korean Wild Mushroom

  • Moon, Dongcheul;Hwang, Kyunghwa;Choi, Kyuyeol;Choi, Dongcheol;Kim, Changsoo;Kim, Jaegil;Lee, Yongmoon;Zee, Okpyo
    • Analytical Science and Technology
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    • v.8 no.4
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    • pp.901-906
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    • 1995
  • Studies on the chemical constituents from a Korean wild mushroom, Phellinus ribis, were carried out. A triterpenoid, two peroxysterols, and a chlorobenzene compound were isolated from the hexane soluble fraction of the methanol extract of dried fruiting bodies of the basidomycetes. Those compounds identifed were 3-hydroxy-20(29)-lupen-28-oic acid (betulinic acid), 5,8-epidioxyergosta-6,22-dien-3-ol(ergosterol peroxide), 5,8-epidioxyergosta-6,9(11),22-trien-3-ol (dehydroperoxyergosterol), and 1,2,4,5-tetrachloro-3,6-dimethoxybenzene. Structural studies were carried out on molecular species of a ceramide and cerebroside isolated from the chloroform soluble fraction of the methanol extract. For ceramide, the major component fatty acids were a-hydroxy fatty acid isomers of $C_{22:00}{\sim}C_{25:00};$ the predominant long-chain bases were trihydroxy sphinganine of $C_{17}{\sim}C_{18}$. The structure of a cerebroside containing mono-sugar was assumed that the long-chain base was $C_{19:2}$ sphingadienine; the major fatty acids were $C_{16}{\sim}C_{15}$ ${\alpha}$-hydroxy fatty acid isomers.

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Comparative Studies on the Composition of Polar Lipids in Japonica and Indica Rice Bran Oils (일반계 및 다수계 미강유의 극성지방질 조성)

  • 권경순;최광수;김현구
    • Journal of the Korean Society of Food Science and Nutrition
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    • v.25 no.5
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    • pp.735-740
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    • 1996
  • This study was carried out to determine the composition of glycolipids and phospholipids in Japonica and Indica rice bran oils. The ratio of glycolipids and phospholipids was 4.1 : 6.5% in Japonica rice bran oils and 2.6 : 3.7% in Indica rice bran oils. Polar lipid content was significantly higher in Japonica rice bran oils. The main components of glycolipids were esterified steryl glycoside, monogalactosyl diglyceride steryl glycoside, cerebroside and digalactosyl diglyceride. The content of esterified steryl glycoside was the highest, resulting in 48.8~52.1% of total glycolipids. Phospholipids in rice bran oils consisted of diphosphatidyl glycerol, phosphatidyl ethanolamines, phosphatidyl inositol, phosphatidyl serines, phosphatidyl choline and lysophosphotidyl choline. Major fatty acids of the glycolipids and phospholipids fractions were oleic, linoleic and palmitic acids in Japonica and Indica rice bran oils.

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A Sphingolipid and Tyrosinase Inhibitors from the Fruiting Body of Phellinus linteus

  • Kang, Hye-Sook;Park, Jin-Ho;Cho, Won-Ki;Park, Jong-Cheal;Choi, Jae-Sue
    • Archives of Pharmacal Research
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    • v.27 no.7
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    • pp.742-750
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    • 2004
  • This paper for the first time reports the isolation of 5 compounds from Phellinus linteus. A sphingolipid (1) and two tyrosinase inhibitory compounds (2, 3) along with two carboxylic acids (4, 5), were isolated from the fruiting body of Phellinus linteus (Berk & Curt) Aoshima. The structure of compound 1 was identified as 1-O-$\beta$-D-glucopyranosyl-(2S, 3R, 4E, 8E)-2-[(2R)-2-hydroxyhexadecanoylamino]-9-methyl-4,8-octadecadiene-1,3-diol, known as cerebroside B, based on spectroscopic methods such as 1D and 2D NMR as well as by acid hydrolysis. Compounds 2-5 were identified as protocatechualdehyde (2), 5-hydroxymethyl-2-furaldehyde (HMF) (3), succinic acid (4), and fumaric acid (5) based on the spectroscopic evidence. Compounds 2 and 3 inhibited the oxidation of L-tyrosine catalyzed by mushroom tyrosinase with an $IC_{50}$ of 0.40 and 90.8 $\mu\textrm{g}$/mL, respectively. The inhibitory kinetics, which were analyzed by the Lineweaver-Burk plots, were found to be competitive and noncompetitive inhibitors with a $K_{j}$ of 1.1 $\mu\textrm{m}$ and 1.4 mM, respectively.

Effects of Sparganii Rhizoma Processed on Rat Lens Aldose Reductase and Anti-oxidant Activities (흑삼릉의 수치에 따른 Aldose Reductase 및 항산화활성에 미치는 영향)

  • 정상훈;신국현;신현경;임순성
    • YAKHAK HOEJI
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    • v.48 no.5
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    • pp.291-296
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    • 2004
  • Sparganium stoloniferum Buch.-Ham. (Sparganiaceae) is a perennial herb which has been used as treatments for menstrual disorder, galactagogue and endometriosis in folk remedies. The Sparganii Rhizoma processed, heated with vinegar, used to different purpose compared with origin in medicine. In order to estimate the different effects between processed (PSR) and unprocessed (USR) Sparganii Rhizoma, extraction and systemic fractionation of the rhizomes were archived. Inhibitory effects of the extracts as well as the fractions of PSR and USR on rat lens aldose reductase and on rat platelet aggregation were investigated for the prevention or the treatment of chronic diabetic complications. Their antioxidant effects, measured using lipid peroxidation of liver tissue and radical scavenging activities on 1,1-diphenyl-picrylhydrazyl in vitro, were evaluated. The most of biological activities tested except rat platelet aggregation, fractions from PSR were shown to exhibit stronger activities than those from USR. It seems that caused by changing of the chemical components by heating process in conditioned with acetic acid. Compounds isolated were shown to significant inhibitory activity on rat lens aldose reductase. Inhibitory activity of compounds isolated on rat lens aldose reductase have been tested in vitro. $IC_{50}$/ (6.31 $\mu$M) of cerebroside I (V) was nearly equal to that (6.32 $\mu$M) of a reference compound, tetrametbylene glutaric acid (TMG).

Cytotoxic and COX-2 Inhibitory Constituents from the Aerial Parts of Aralia cordata

  • Lee, Ik-Soo;Jin, Wen-Yi;Zhang, Xin-Feng;Hung, Tran-Manh;Song, Kyung-Sik;Seong, Yeon-Hee;Bae, Ki-Hwan
    • Archives of Pharmacal Research
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    • v.29 no.7
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    • pp.548-555
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    • 2006
  • Three diterpenes (1, 8, and 9), three triterpenes (3, 4, and 7), one saponin (11), four sterols (2, 5, 6, and 12), and one cerebroside (10) were isolated from the EtOH extract of the aerial parts of Aralia cordata by repeated silica gel column chromatography. Their chemical structures were identified by comparing their physicochemical and spectral data with those published in literatures. All isolated compounds were evaluated for their cytotoxicity against L1210, K562, and LLC tumor cell lines using MTT assay. Of which, $3{\beta},5{\alpha}-dihydroxy-6{\beta}-methoxyergosta-7,22-diene$ (6) showed a potent cytotoxicity against all cell lines with $IC_{50}$ values of 11.7, 11.9, and $15.1\;{\mu}M$, respectively, while compounds 1, 5, and 11 showed a moderate or weak cytotoxicity. These isolates were also examined for their inhibitory activity against COX-1 and COX-2. Although most compounds, except for 2, 10, and 12, showed a strong inhibitory activity against COX-1, they exhibited a moderate or weak inhibitory activity against COX-2.