• Tuberculosis and Respiratory Diseases
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• v.78 no.3
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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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• v.15 no.4
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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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• v.10 no.2
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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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• v.57 no.4
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• pp.295-299
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• 2014

The mulberry (Morus alba L.) root barks were extracted with 80% aqueous methanol at room temperature. The concentrated extract was partitioned as ethyl acetate (EtOAc), n-BuOH, and $H_2O$ fractions. From the EtOAc fraction, five triterpenoids were isolated through the repeated silica gel and octadecyl $SiO_2$ column chromatographies. According to the results of physico-chemical and spectroscopic data including nuclear magnetic resonance, mass spectrometry, and infrared, the chemical structures of the triterpenoids were respectively determined as ${\alpha}$-amyrin (1), ${\alpha}$-acetyl amyrin (2), lupeol (3), betulinic acid (4), and glutinol (5). Compounds 1, 3, and 5 were isolated for the first time from the mulberry root bark.

• Journal of Life Science
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• v.33 no.11
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• pp.859-867
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• 2023

Lupeol is a type of pentacyclic triterpene that has been reported to have therapeutic effects for treating many diseases; however, its effect on insulin resistance is unclear clear. This study examined the inhibitory effect of lupeol on the serine phosphorylation of insulin receptor substrate-1 in insulin resistance-induced 3T3-L1 adipocytes. 3T3-L1 cells were cultured and treated with tumor necrosis factor-α (TNF-α) for 24 hours to induce insulin resistance. Cells treated with different concentrations of lupeol (15 μM or 30 μM) or 100 nM of rosiglitazone were incubated. Then, lysed cells underwent western blotting. Lupeol exhibited a positive effect on the negative regulator of insulin signaling and inflammation-activated protein kinase caused by TNF-α in adipocytes. Lupeol inhibited the activation of protein tyrosine phosphatase-1B (PTP-1B)-a negative regulator of insulin signaling-and c-Jun N-terminal kinase (JNK); it was also an inhibitor of nuclear factor kappa-B kinase (IKK) and inflammation-activated protein kinases. In addition, Lupeol downregulated serine phosphorylation and upregulated tyrosine phosphorylation in insulin receptor substrate-1. Then, the downregulated phosphatidylinositol 3-kinase (PI3K)/protein kinase B (AKT) pathway was activated, the translocation of glucose transporter type 4 was stimulated to the cell membrane, and intracellular glucose uptake increased in the insulin resistance-induced 3T3-L1 adipocytes. Lupeol may improve TNF-α-induced insulin resistance by downregulating the serine phosphorylation of insulin receptor substrate 1 by inhibiting negative regulators of insulin signaling and inflammation-activated protein kinases in 3T3-L1 adipocytes.

• YAKHAK HOEJI
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• v.45 no.6
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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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• v.13 no.5
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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.

• Korean Journal of Medicinal Crop Science
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• v.3 no.2
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• pp.151-155
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• 1995

Chromatographic separation of Laduca raddeana extract afforded a mixture of fatty acyl triterpene, triterpene acetates and primary long chain alcohol. The kind of triterpene moieties in these two triter­penoids was six, i.e., ${\beta}-amyrin,\;{\alpha}-amyrin$, lupeol, pseudotaraxasterol, taraxasterol and germanicol on the basis of chemical and spectroscopic methods. The acyl moieties in the corresponding acyl mixture were characterized as acetates, myristate, palmitate, stearate and arachidate. And a mixture of primary long chain alcohol were composed of teracosanol and hexacosanol.

• 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.

• Biomolecules & Therapeutics
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• v.11 no.1
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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.