• Title/Summary/Keyword: 23-hydroxyursolic acid

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In vitro Antiinflammatory Activity of 23-Hydroxyursolic Acid Isolated from Cussonia bancoensis in Murine Macrophage RAW 264.7 Cells

  • Kim, Rung-Gyu;Shin, Kyung-Min;Park, Hee-Juhn;Park, Jong-Won;Lee, Kyung-Tae
    • Proceedings of the PSK Conference
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    • 2002.10a
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    • pp.320.1-320.1
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    • 2002
  • We investigated the effect of various triterpenoids isolated from the Cussonia bancoensis. such as ursolic acid. 23-hydroxyursolic acid. 3-O-${\alpha}$-L -arabinopyranosyl-23 -hydroxyursolic acid. 3-O-${\beta}$-D-glucopyranosyl-23-hydroxy-ursolic acid and 28-O-${\alpha}$-L -rhamnopyranosyl(1-4)-${\beta}$-D-glucopyranosyl( 1-6)-${\beta}$-D-glucopyranosylester of 23-hydroxyursolic acid. have been evaluated on lipopolysaccharide (LPS)-induced nitric oxide (NO) and prostaglandin E2 (PGE2) release by the macrophage cell line RAW 264.7. (omitted)

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23-hydroxyursolic acid Induces Apoptosis of human leukemia HL-60 cells

  • Heon, Won-Jong;Shin, kyung-Min;Rim, Seo-Bo;Park, Hee-Jun;Park, Jong-Won;Lee, Kyung-Tae
    • Proceedings of the PSK Conference
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    • 2002.10a
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    • pp.318.1-318.1
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    • 2002
  • We found that 23-hydroxyursolic acid, triterpenoid was isolated from Cussonia bancoensis have a significant cytotoxic activity against HL -60 human promyelocytic leukemia cells. The IC of 23-hydroxyursolic acid was 32.83 $\mu$M. These anti-proliferative activity was due to induction of apoptosis. The effect of apoptosis was identified by DNA laddering, DAPI assay. PI staining, and Annerxin V-FITC binding assay. (omitted)

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In Vivo Anti-Nociceptive and Anti-Inflammatory Effect of the Two Triterpenes, Ursolic Acid and 23-Hydroxyursolic Acid, from Cussonia bancoensis

  • Tapondjou, L.A.;Lontsi, David;Sondengam, Beiban-Luc;Choi, Jong-Won;Lee, Kyung-Tae;Jung, Hyun-Ju;Park, Hee-Juhn
    • Archives of Pharmacal Research
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    • v.26 no.2
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    • pp.143-146
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    • 2003
  • Triterpenoids, ursolic acid (1) and 23-hydroxyursolic acid (2) were obtained from the hydrolysis of BuOH fraction of Cussonia bancoensis extract to test anti nociceptive and anti-inflammatory effect of C. bancoensis (Araliaceae). Compound 1 and 2 exhibited anti-nociceptive effects, which were determined by acetic acid-induced writhing test and hot plate test. The effect of 2 was much more potent in acetic acid-induced writhing test than in hot plate test. Compound 1 and 2 significantly inhibited 1%-carrageenan-induced edema in the rat. These results suggest that the two triterpenes, ursolic acid and 23-hydroxyursolic acid, are responsible for the antinociceptive and anti-inflammatory effect of C. bancoesnsis.

Studies on Components of Patrinia scabiosaefolia

  • Kim, Young-Hee
    • Korean Journal of Pharmacognosy
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    • v.28 no.2
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    • pp.93-98
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    • 1997
  • Rutin, ${\alpha}-hederin$ and kalopanax saponin B and a mixture of hederagenin and 23-hydroxyursolic acid were isolated from the aerial parts of Patrinia scabiosaefolia Fisch.

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Triterpenoids from the Roots of Rubus parvifolius

  • Choi, Yoon-Soo;Son, Kun-Ho;Do, Jae-Chu
    • Archives of Pharmacal Research
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    • v.14 no.3
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    • pp.225-230
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    • 1991
  • From the roots of Rubus parvifolius L., four triterpenoidal sapogenins, ursolic acid 1. $2\alpha$-hydroxyursolic acid 2. causapic acid 3. $2\alpha$, $3\beta$, $19\alpha$-trihydroxyurs-12-en-23.28-dioic acid 4 and one triterpenoidal glycoside. suavissimoside $R_1$ 5. were isolated. The structures were elucidated by spectroscopic methods and chemical transformations. Compound 4 was first isolated as free form.

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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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Anti-complement Activity of Triterpenoids from the Whole Plant of Patrinia saniculaefolia

  • An, Ren-Bo;Na, Min-Kyun;Min, Byung-Sun;Lee, Hyeong-Kyu;Bae, Ki-Hwan
    • Natural Product Sciences
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    • v.14 no.4
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    • pp.249-253
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    • 2008
  • Two oleanane-type triterpenes (1, 2) and their glycosides (4-6), and one ursane-type triterpene (3) have been isolated from a methanolic extract of Patrinia saniculaefolia Hemsley (Valerianaceae) through repeated silica gel and reversed-phase C-18 column chromatography. Their chemical structures were determined as oleanolic acid (1), oleanonic acid (2), 23-hydroxyursolic acid (3), 3-O-${\alpha}$-L-arabinopyranosyl-oleanolic acid (4), 3-O-${\beta}$-D-glucopyranosyl-oleanolic acid (5), and oleanolic acid 3-O-[${\alpha}$-D-xylopyranosyl-($1{\rightarrow}3$)-${\beta}$-D-glucuronopyranoside-6-O-butyl-ester] (6) on the basis of their MS, $^1H$-, and $^{13}C$-NMR spectral data. All compounds were isolated from the whole plant of the P. saniculaefolia for the first time. These compounds were examined for their anti-complement activity against the classical pathway of the complement system. Among them, compounds 1 - 3 exhibited anti-complement activity with $IC_{50}$ values of 470.1, 212.2, and 121.0 ${\mu}M$, respectively, whereas compounds 4 - 6 were inactive. These results suggest that the carbonyl or hydroxy group at C-3 in the oleananeand/or ursane-triterpenes are important for the anti-complement activity against the classical pathway.

Ursane-Type Triterpenoids from the Aerial Parts of Potentilla discolor

  • Jang, Dae-Sik;Kim, Jong-Min;Lee, Ga-Young;Kim, Joo-Hwan;Kim, Jin-Sook
    • Journal of Applied Biological Chemistry
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    • v.49 no.2
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    • pp.48-50
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    • 2006
  • Four ursane-type triterpenoids, ursolic acid (1), 23-hydroxyursolic acid (2), corosolic acid (3), and tormentic acid (4), and a phytosterol, ${\beta}-sitosterol-3-O-{\beta}-D-glucoside$, were isolated from an EtOAcsoluble extract of the aerial parts of Potentilla discolor. The structures of 1-4 were identified by spectroscopic methods, particularly by extensive NMR studies. This is the first report on the isolation of compounds 1-4 from this plant.

Triterpenoids from the Flower of Campsis grandiflora K. Schum. As Human Acyl-CoA: Cholesterol Acyltransferase Inhibitors

  • Kim, Dong-Hyun;Han, Kyung-Min;Chung, In-Sik;Kim, Dae-Keun;Kim, Sung-Hoon;Kwon, Byoung-Mog;Jeong, Tae-Sook;Park, Mi-Hyun;Ahn, Eun-Mi;Baek, Nam-In
    • Archives of Pharmacal Research
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    • v.28 no.5
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    • pp.550-556
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    • 2005
  • The flower of Campsis grandiflora K. Schum. Was extracted with 80% aqueous MeOH, and the concentrated extract was partitioned with EtOAc, n-BuOH and H$_2$O. From the EtO Ac fraction, seven triterpenoids were isolated through the repeated silica gel, ODS column chromatographies and preparative HPLC. From the result of physico- chemical data including NMR, MS and IR, the chemical structures of the compounds were determined as 3${\beta}$-hydroxyolean-12-en-28-oic acid (oleanolic acid, 1), 3${\beta}$-hydroxyurs-12-en-28-oic acid (ursolic acid, 2), 3${\beta}$-hydroxyurs-12-en-28-al (ursolic aldehyde, 3), 2${\alpha}$,3${\beta}$-dihydroxyolean-12-en-28-oic acid (maslinic acid, 4), 2${\alpha}$,3${\beta}$-dihydroxyurs-12-en-28-oic acid (corosolic acid, 5), 3${\beta}$,23-dihydroxyurs-12- en-28-oic acid (23-hydroxyursolic acid ,6) and 2${\alpha}$,3${\beta}$,23-trihydroxyolean-12-en-28- oic acid (arjunolic acid, 7). These teriterpenoids were isolated for the first time from this plant. Also, compounds 4, 5, 6, and 7 revealed relatively high hACAT-1 inhibitory activity with the value of 46.2${\pm}$1.1, 46.7${\pm}$0.9, 41.5${\pm}$1.3 and 60.8${\pm}$1.1% at the concentration of 100${\mu}$g/mL, respectively.

Anti-Inflammatory Activity of Compounds from the Whole Plant of Patrinia saniculaefolia

  • An, Ren-Bo;Na, Min-Kyun;Min, Byung-Sun;Chang, Hyeun-Wook;Bae, Ki-Hwan
    • Natural Product Sciences
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    • v.17 no.2
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    • pp.90-94
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    • 2011
  • An in vitro bioassay-guide revealed that the methanol (MeOH) extract of the whole plant of Patrinia saniculaefolia (Valerianaceae) showed cyclooxygenase-2 (COX-2) and 5-lipoxygenase (5-LOX) dual inhibitory activity by assessing their effects on the production of prostaglandin $D_2$ ($PGD_2$) and leukotriene $C_4$ ($LTC_4$) in mouse bone marrow-derived mast cells (BMMCs). Phytochemical study of the MeOH extract of this plant led to the isolation of twelve compounds; ${\beta}$-farnesene (1), squalene (2), nardostachin (3), patridoid I (4), patridoid II (5), patridoid II-A (6), oleanolic acid (7), oleanonic acid (8), 23-hydroxyursolic acid (9), oleanolic acid 3-O-${\alpha}$-L-arabinopyranoside (10), oleanolic acid 3-O-${\beta}$-D-glucopyranoside (11), oleanolic acid 3-O-[${\beta}$-D-xylopyranosyl-(1${\rightarrow}$3)-${\beta}$-D-(6-O-butyl)glucuronopyranoside] (12). Among the compounds, 4 and 5 strongly inhibited both the COX-2-dependent $PGD_2$ generation with $IC_{50}$ values of 8.7 and 13.6 ${\mu}M$, respectively, and the generation of $LTC_4$ in the 5-LOX dependent phase with $IC_{50}$ values of 41.7 and 46.9 ${\mu}M$, respectively, which suggest that the anti-inflammatory activity of P. saniculaefolia might occur in part via the inhibition of both $PGD_2$ and $LTC_4$ generation by 4 and 5.