• Tuberculosis and Respiratory Diseases
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• 제78권3호
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• pp.210-217
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• 2015

Background: Adenophora triphylla var. japonica is empirically used for controlling airway inflammatory diseases in folk medicine. We evaluated the gene expression and production of mucin from airway epithelial cells in response to lupenone, lupeol and taraxerol derived from Adenophora triphylla var. japonica. Methods: Confluent NCI-H292 cells were pretreated with lupenone, lupeol or taraxerol for 30 minutes and then stimulated with tumor necrosis factor ${\alpha}$ (TNF-${\alpha}$) for 24 hours. The MUC5AC mucin gene expression and production were measured by reverse transcription-polymerase chain reaction and enzyme-linked immunosorbent assay, respectively. Additionally, we examined whether lupenone, lupeol or taraxerol affects MUC5AC mucin production induced by epidermal growth factor (EGF) and phorbol 12-myristate 13-acetate (PMA), the other 2 stimulators of airway mucin production. Results: Lupenone, lupeol, and taraxerol inhibited the gene expression and production of MUC5AC mucin induced by TNF-${\alpha}$ from NCI-H292 cells, respectively. The 3 compounds inhibited the EGF or PMA-induced production of MUC5AC mucin in NCI-H292 cells. Conclusion: These results indicated that lupenone, lupeol and taraxerol derived from Adenophora triphylla var. japonica regulates the production and gene expression of mucin, by directly acting on airway epithelial cells. In addition, the results partly explain the mechanism of of Adenophora triphylla var. japonica as a traditional remedy for diverse inflammatory pulmonary diseases.

• Archives of Pharmacal Research
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• 제15권4호
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• pp.322-327
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• 1992

From the stem bark of Catalpa ovata, lupeol, 2(4-hydroxyphenyl)ethyl triacotanoate, a mixture of 9-hydroxy .alpha.-lapachone, 9-methoxy $\alpha$-lapachone, ferulic acid, 6-feruloyl catalpol, catalposide and 6'-feruloyl sucrose were isolated and identified.

• Natural Product Sciences
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• 제10권2호
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• pp.59-62
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• 2004

A novel chlorinated diterpene quinone methide; chlorosmaridione (7-chloro-11-hydroxy-abeita-7,9(11),13-triene-6,12-diode) was isolated from petroleum ether extract of the stems of Rosemarinus officinalis L. growing in Egypt. In addition, ${\beta}-sitosterol$, stigmasterol, lupeol acetate, ${\alpha}-amyrin,\;{\beta}-amyrin$, lupeol, acetyloleanolic acid, acetylursolic acid taxodione, horminone, and cryptotanshinone were also identified. Chemical structures of the isolated compounds have been elucidated on the bases of physical, chemical, and spectral data including IR, UV, MS, 1D-and 2D-NMR spectra.

• Journal of Applied Biological Chemistry
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• 제57권4호
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• pp.295-299
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• 2014

뽕나무(Morus alba L.) 뿌리껍질을 실온에서 80% MeOH 수용액으로 추출하고 이 추출물을 EtOAC 분획, n-BuOH 분획, $H_2O$ 분획으로 나누었다. EtOAc 분획에 대하여 silica gel과 ODS column chromatography를 반복 실시하여 5종의 triterpenoid를 분리, 정제하였다. NMR, IR, 및 EI/MS 등을 해석하여, ${\alpha}$-amyrin (1), ${\alpha}$-acetyl amyrin (2), lupeol (3), betulinic acid (4) 그리고 glutinol (5)로 구조동정 하였다. 화합물 중 a-amyrin (1), lupeol (3) 그리고 glutinol (5)은 상백피로부터는 이번 실험에서 처음으로 분리되었다.

• 생명과학회지
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• 제33권11호
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• pp.859-867
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• 2023

루페올은 5환성 트리테르펜의 일종으로 많은 질병에 치료 효과가 있는 것으로 보고되었으나, 인슐린 저항성에 미치는 영향은 명확하지 않다. 본 연구에서는 3T3-L1 지방세포에서 루페올의 IRS-1 인산화 억제능을 통해 인슐린 저항성 개선효과를 조사하였다. 3T3-L1 세포를 배양하고 TNF-α를 24시간 동안 처리하여 인슐린 저항성을 유도하였다. 서로 다른 농도의 루페올(15, 30 μM) 또는 100 nM의 rosiglitazone을 처리한 세포를 배양한 후, 용해된 세포를 이용하여 western blotting을 시행하였다. 실험결과 루페올은 지방세포에서 TNF-α에 의해 유발되는 인슐린 신호전달의 음성 조절자와 염증 활성화 단백질 kinase에 대한 개선 효과를 나타냈다. 인슐린 신호전달의 음성 조절자인 PTP-1B와 JNK의 활성 및 IKK와 염증활성화 단백질키나아제의 활성을 억제하였다. 또한, 루페올은 IRS-1의 serine 인산화는 하향 조절하고 tyrosine 인산화는 상향 조절하였다. 그 후, 하향 조절된 PI3K/AKT 경로가 활성화되고, GLUT 4의 세포막 전위가 자극되어, 결과적으로 인슐린 저항성이 유도된 3T3-L1 지방세포에서에서 세포내 포도당 흡수가 증가하였다. 본 연구결과, 루페올은 3T3-L1 지방세포에서 인슐린 신호전달 및 염증 활성화 단백질 kinsase들의 음성 조절인자를 억제하여, IRS-1의 serine 인산화를 하향 조절함으로써 TNF-α 유발 인슐린 저항성을 개선할 수 있을 것으로 사료된다.

• 약학회지
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• 제45권6호
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• pp.591-598
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• 2001

The photochemical study of Viscum album (Loranthaceae) led to the isolation of twelve compounds, lupeol (1), betulonic acid (2), betulinic acid (3), terminic acid (4), ursolic acid (5), $\beta$-sitosterol (6), $\alpha$- spinasterol (7), oleanolic acid (8) , 5-hydroxy-1- (4′-hydoxyphenyl) -7- (4"-hydroxyphenyl) -hepta-1- en-3-on (9), 2′-hydroxy -4′, 6′- dimethoxychalcone -4-O-glycoside (10) ,2′-hydroxy-4′, 6′-dimethoxychalcone -4-O- [apiosal(1longrightarrow12)]glucoside (11) and syringin (12). Their structures were established by chemical and spectroscopic methods. The cytotoxicity of the isolated compounds was evaluated by sulforhodamine B assay against five cultured human tumor cell lines.

• Journal of Microbiology and Biotechnology
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• 제13권5호
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• pp.778-782
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• 2003

In the course of screening anti-influenza agents from natural products, four neuraminidase inhibitors were isolated from the methanol extract of mushroom Microphorus affinis by purification using solvent partition, silica gel column chromatography, Sephadex LH-20, and semi-preparative HPLC. The chemical structures of these compounds were identified as ${\alpha}-lupeol$, methyl linoleate, methyl palmitate, and methyl oleate by means of spectral data including GC-MS, $^1H-,\;and\;^{13}C-NMR\;with\;IC_{50}$ values of 5.65, 7.07, 7.12, and $7.52\;\mu\textrm{M}$, respectively. They did not inhibit other glycosidases such as glucosidase, mannosidase, and galactosidase, indicating that they were relatively specific inhibitors of neuraminidase. The relationship between the fatty acid structure and inhibitory activity was investigated. The result showed that, in the case of an aliphatic linear hydrocarbon skeleton, at least one carboxyl (presumably any carbonyl) moiety and sixteen carbons were the necessary requirements for potent inhibition, whereas saturated, unsaturated, free, and ester forms did not have any significant effect on the activity.

• 한국약용작물학회지
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• 제3권2호
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• pp.151-155
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• 1995

국화과 식물인 산씀바귀(Lactuca raddeana)를 식물화학적 방법에 의하여 연구한 바 primaylong chain alcohol인 1-hexacosanol과 1-tetracosa not을, triterpene acetate로 ${\beta}-amyrin\;acetate,\;{\alpha}-amyrin acetate$, lupeol acetate, pseudotaraxasterol acetate, taraxasterol acetate 및 germanicol acetate등을, fatty acyl triterpene은 이들의 구성 triter pone alcohol이 triterpone acetate의 경우와 같았으며 acyl moiety는 myristate, palmitate, stearate및 arachidate로 각각 나타났다.

• 생약학회지
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• 제39권3호
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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.

• Biomolecules & Therapeutics
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• 제11권1호
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• pp.1-4
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• 2003

Plants are known as important source in the search for new drugs. The twelve compounds from Viscum album (Loranthaceae), lupeol (1), betulonic acid (2), betulinic acid (3), terminic acid (4), ursolic acid (5), $\beta$-sitosterol (6), $\alpha$-spinasterol (7), oleanolic acid (8), 5-hydroxy-1-(4′-hydoxyphenyl)-7-(4"-hydroxyphenyl)-hepta-1-en-3-on (9), 2′-hydroxy-4′,6′-dimethoxychalcone-4-O-glucoside (10), 2′-hydroxy-4′,6′-dimethoxychalcone-4-O-[apiosyl(l$\longrightarrow$2)]glucoside (11) and syringin (12) were evaluated for their immunomodulatory properties. Compounds 6 and 11 induced the macrophage tumoricidal activity and the lymphocyte blastogenesis. In addition, these compounds stimulated the macrophages to induce the production of TNF-$\alpha$ and NO. These findings suggest that compounds 6 and 11 are modulating various elements of the host immune response.