• Title/Summary/Keyword: Tormentic acid

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Inhibitory Effect of Euscaphic Acid and Tormentic Acid from the Roots of Rosa rugosa on High Fat Diet-Induced Obesity in the Rat (고지방 식이로 유도된 비만 흰쥐에서 해당근에서 분리된 Euscaphic Acid 및 Tormentic Acid의 효과)

  • Park, Hee-Juhn;Nam, Jung-Hwan;Jung, Hyun-Ju;Lee, Myung-Sun;Lee, Kyung-Tae;Jung, Min-Hwa;Choi, Jong-Won
    • Korean Journal of Pharmacognosy
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    • v.36 no.4 s.143
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    • pp.324-331
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    • 2005
  • The roots of Rosa rugosa have been used to treat diabetes mellitus in the folkloric society of Korea. To demonstrate the active component for the rat obesity induced by high fat diet for 6 weeks, the phytochemical fractionation and the pharmacological activity test were performed on this crude drug. It was shown that the methanolic extract and its EtOAc fraction inhibited the weight increase of the rat body, abdominal fat pad and hyperlipidemia at 200 mg/kg dose. Further, the triterpenoids, euscaphic acid and tormentic acid, isolated from R. rugosa roots were active at 30 mg/kg in the same assay. The two components shifted serum total-, HDL, and LDL-cholesterol levels toward the values of the unteated group, suggesting that the active compounds has hypolipidemic effects. The rats fad euscaphic acid and tormentic acid also reduced thiobarbituric acid-reactive substance (TBARS) and hydroxyl radical in the rat blood and increased superoxide dismutase activity compared to the control. TBARS values and carbonyl contest of the hepatic protein were reduced by treatment with the two triterpenoids. Antioxidative enzyme (SOD, glutathione peroxidase, and catalase) activities in hepatic were increased by treatment of rats with the triterpenoids, which suggests that triterpenoids inhibited the reduction of hepatic antioxidative activity caused by high fat diet. Taken together, these results support that euscaphic acid and tormentic acid improve a high fat diet-induced hyperlipidemia via the activation of antioxidative mechanism.

Triterpenoid glycosides from rosa rugosa

  • Young, Han-Suk;Park, Jong-Cheol;Choi, Jae-Sue
    • Archives of Pharmacal Research
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    • v.10 no.4
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    • pp.219-222
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    • 1987
  • From the underground parts of Rosa rugosa(Rosaceae), 28-0-glucosides of euscaphic acid, tormentic acid and arjunic acid were isolated and characterized by spectral data.

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Isolation and Characterization of Acidic Triterpenes from the Fruits of Chaenomeles sinensis (모과로부터 산성 트리테르펜의 분리 및 동정)

  • 노승배;장은하;임광식
    • YAKHAK HOEJI
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    • v.39 no.6
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    • pp.610-615
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    • 1995
  • Three acidic triterpense were isolated from the ethyl acetate soluble fraction of the fruits of Chenomeles sinensis (Rosaceae) together with previously reported oleanolic acid and ursolic acid by repeated silica gel colunm chromatography. Their structures have been elucidated as $2{\alpha},{\;}3{\betha}-dihydroxyolean-l2-en-28-oic$ acid(l. maslinic acid), $2{\alpha},{\;}3{\alpha},{\;}19{\alpha}-trihydroxy-urs-12-en-28-oic$ acid (2, euscaphic acid), and $2{\alpha},{\;}3{\betha}-dihydroxyolean-l2-en-28-oic$ acid (3,tormentic acid), respectively, on the basis of chemical and spectral evidence.

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Structure Determination of a New Lupane-type Triterpene, Tiarellic Acid, Isolated from Tiarella polyphylla

  • Lee, Hyeong-Kyu;Park, Si-Hyung;Oh, Sei-Ryang;Ahn, Kyung-Seop;Kim, Jae-Gil
    • Archives of Pharmacal Research
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    • v.25 no.1
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    • pp.57-60
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    • 2002
  • A new 27-carboxylic lupane-type triterpene, tiarellic acid (1), was isolated from Tiarella polyphylla together with corosolic acid (2) and tormentic acid (3). Tiarellic acid was characterized as 3,23-dihydroxy-20(29)-lupen-27-oic acid and its NMR data were unambiguously assigned using 2-D NMR techniques.

Constituents of the Aerial Parts of Agrimonia pilosa

  • An, Ren-Bo;Kim, Hyun-Chul;Jeong, Gil-Saeng;Oh, Seung-Hwan;Oh, Hyun-Cheol;Kim, Youn-Chul
    • Natural Product Sciences
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    • v.11 no.4
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    • pp.196-198
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    • 2005
  • Four ursane type triterpenes have been isolated from the methanolic extract of the aerial parts of Agrimonia pilosa Ledeb. (Rosaceae) through repeated silica gel and reverse-phase C-18 column chromatography. Their chemical structures were elucidated as ursolic acid (1), pomolic acid (2), tormentic acid (3), and corosolic acid (4) on the basis of their MS, $^1H-$, and $^{13}C-NMR$ spectral data. Compounds 2 and 4 were isolated from the genes of Agrimonia for the first time.

In vivo Antinociceptive and Anti-inflammatory Effect of the Two Triterpenes. Ursolic Acid and 23- Hydroxyursolic Acid. of Cussonia bancoensis

  • Tapondjou L.A;Choi, Jong-Won;Lee, Kyung-Tae;Jung, Hyun-Ju;Park, Hee-Juhn
    • Proceedings of the PSK Conference
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    • 2002.10a
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    • pp.371.1-371.1
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    • 2002
  • Triterpenoids. Ursolic acid (1). 23-hydroxyursolic acid (2). and tormentic acid (3) were obtained by the hydrolysis of BuOH fraction of Cussonia bancoensis extract and further chromatographic isolation to test antinociceptive and anti-inflammatory effect of C. bancoensis (Aratiaceae). Compound 1 and 2 exhibited anti-nociceptive effects, which were determined by acetic acid-induced writhing test and hot plate test. However. the effect of tormentic acid was not significant (omitted)

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Comparison of Triterpenoid Contents of the Four Rubus Plants in Korea Using TLC-DM (TLC-DM을 이용한 Rubus속 4종 식물의 Triterpenoid 함량 비교)

  • Nam, Jung-Hwan;Jung, Hyun-Ju;Choi, Jong-Won;Kim, Won-Bae;Park, Hee-Juhn
    • Korean Journal of Pharmacognosy
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    • v.38 no.2 s.149
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    • pp.187-191
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    • 2007
  • The extraction yield of the methanolic extracts and 19${\alpha}$-hydroxyursane-type triterpenoid (19${\alpha}$-HUT) fraction were investigated in the unripe and ripe fruits and the leaves of the four Rubus plants (Rubus coreanus, R. crataegifolius, R. phoenicolasius, R. pungens var. oldhami) to develop the biomaterial 19${\alpha}$-HUT mixture as functional foods. Thin layer chromatogaphy-Densitometer (TLC-DM) was used to analyze the individual quantity of 19${\alpha}$-HUTs using standard compounds (euscaphic acid, tormentic acid, 23-hydroxytormentic acid, kaji-ichigoside F$_1$, rosamultin, niga-ichigoside F$_1$). The content of methanolic extract of the fruits were higher in the ripe stage than in the unripe stage whereas the content of 19${\alpha}$-HUT mixture varied with each Rubus species. The Rubus plants containing the highest amount of 19${\alpha}$-HUTs in the leaves were R. coreanus, R. phoenicolasius and R. pungens var. oldhami while only R. cratagefolius showed the highest content in the ripe fruits. The mean of total genin content of 19${\alpha}$-HUTs was 0.94 mg/g; that of the glycosides was 0.60 mg/g. The genin quantity was found in the order of 23-hydroxytormentic acid> euscaphic acid> tormentic acid; the glycoside was observed in the order of niga-ichig-oside F$_1$> kaji-ichigoside F$_1$> rosmaultin, by which the biosynthetic pathway of 23-hydroxytormentic acid and its glucoside niga-ichigoside F$_1$ via the intermediates tormentic acid and/or rosamultin was presumed. It is also suggested that the ripe fruits of R. crataegifolius will be desirable to use as functional foods rather than unripe fruits.

Chemical Characterization and Utilization of $19{\alpha}-Hydroxyursane-type$ Triterpenoids in Rubus species (Rubus속 식물에 존재하는 $19{\alpha}-Hydroxyursane-type$ Triterpenoid의 특성과 이용)

  • Jung, Hyun-Ju;Nam, Jung-Hwan;Lim, Sang-Cheol;Kim, Won-Bae;Park, Hee-Juhn
    • Korean Journal of Plant Resources
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    • v.19 no.5
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    • pp.563-572
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    • 2006
  • The plant Rubus species (Rosaceae) mainly contains $19{\alpha}-hydroxyurane-type$ triterpenoids $(19{\alpha}-HUT)$ as bioactive components. Available functional food includes blackberry (the fruit of thornless Rubus sp.), red raspberry (R. idaeus) and black raspberry (R. occidentalis). However, the fruit of R. coreanus, which is used in Korea as a functional food, substitutes black raspberry. Rubi Fructus, which has been traditionally used as an oriental medicinal drug, designates only unripe fruit of R. coreanus but not its ripe fruit which indicates that it needs high content of $19{\alpha}-HUT$ as a crude drug. Throughout our experiment, we found that ripe fruits contain very little amount of $19{\alpha}-HUT$ when compared to unripe fruits. In addition, various and rich $19{\alpha}-HUT$ has been reported from Rubus species. The most common structure of $19{\alpha}-HUT$ of Rubus species, euscaphic acid or tormentic acid with $3{\alpha}-OH$ or $3{\beta}-OH$, respectively, can be glycosylated or oxidized to produce a number of $19{\alpha}-HUTs $as euscaphic acid and tormentic acid derivatives and even esterified to form dimeric triterpenoids. In this review, the bioactivity and biosynthetic pathway and chemical characterization of $19{\alpha}-HUTs$ found in Rubus species are discussed.

Phytochemical Constituents Isolated from the Stems of Chaenomeles sinensis Koehne (모과나무 줄기의 화학성분)

  • Shin, Ji-Eun;Jin, Qing-Long;Jin, Hong-Guang;Woo, Eun-Rhan
    • Korean Journal of Pharmacognosy
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    • v.42 no.3
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    • pp.223-228
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    • 2011
  • Chaenomeles sinensis Koehne (Rosaceae) is a deciduous tree and is distributed in China, Korea and Japan. In previous studies on the fruits of C. sinensis, some triterpenoid compouds such as oleanolic acid, tormentic acid were reported. In an ongoing investigation into biologically active compounds from natural products, the methanol extract of the stems of C. sinensis was investigated. By means of the repeated column chromatography using silica gel, Sephadex LH-20, LiChroprep RP-18, betulin (1), tormentic acid (2), 1-${\beta}$-D-glucopyranosyl-3,4,5-trimethoxybenzene (3), lyoniresinol-2a-O-${\alpha}$-L-rhamnopyranoside (4) were isolated. The chemical structures of compounds 1-4 were determined by the basis of physico-chemical properties and spectroscopic methods such as 1D and 2D NMR. For the isolated compounds (1-4), the inhibitory activity of IL-6 production in TNF-${\alpha}$ stimulated MG-63 cell was examined. Among the isolates, betulin (1), 1-${\beta}$-D-glucopyranosyl-3,4,5-trimethoxybenzene (3), lyoniresinol-2a-O-${\alpha}$-L-rhamnopyranoside (4) showed inhibitory effects on IL-6 production in TNF-${\alpha}$ stimulated MG-63 cell.