- Pentacyclic triterpenes and naphthoquinones from Euclea divinorum
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Phytochemical studies on Euclea divinorum have resulted in the isolation of lupeol, lupene, betulin, 7-methyljuglone, isodiospyrin, shinalone, catechin and 3β-(5-hydroxyferuloyl)lup-20(30)-ene. The structures were assigned on the basis spectral and chemical studies and the compounds were evaluated for their cytotoxic activity.
- Mebe, Paul P.,Cordell, Geoffrey A.,Pezzuto, John M.
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- TRITERPENOIDS OF AMSONIA GRANDIFLORA
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Stems and leaves of Amsonia grandiflora yielded lupeol β-hydroxyoctadecanoate, betulinic acid, oleanolic acid, lupeol, lupeol acetate and 1-O-methyl-myo-inositol. - Key Word Index: Amsonia grandiflora; Apocynaceae; stems; leaves; triterpenoids; lupeol β-hydroxyoctadecanoate.
- Wahyuono, Subagus,Hoffmann, Joseph J.,Jolad, Shivanand D.,Dentali, Steven J.
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- Antibacterial activity of naphthoquinones and triterpenoids from Euclea natalensis root bark
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Phytochemical studies of an ethanolic extract of Euclea natalensis root bark afforded two new compounds, octahydroeuclein (1) and 20(29)-lupene-3β- isoferulate (2), in addition to three known compounds, shinanolone (3), lupeol, and betulin. The chemical structures of 1 and 2 were determined by spectroscopic means. Shinanolone (3) showed inhibitory activity against Gram-positive bacterial strains and a drug-sensitive strain of Mycobacterium tuberculosis at a concentration of 0.1 mg/mL.
- Weigenand, Oliver,Hussein, Ahmed A.,Lall, Namrita,Meyer, Jacobus J. M.
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- Practical Synthesis of α-Amyrin, β-Amyrin, and Lupeol: The Potential Natural Inhibitors of Human Oxidosqualene Cyclase
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A practical synthesis of α-amyrin (1), β-amyrin (2), and lupeol (3) was accomplished in total yields of 32, 42, and 40% starting from easily available ursolic acid (4), oleanolic acid (5), and betulin (6), respectively. Remarkably, these three natural pentacyclic triterpenes exhibited potential inhibitory activity against human oxidosqualene cyclase.
- Chen, Dongyin,Xu, Fengguo,Zhang, Pu,Deng, Jie,Sun, Hongbin,Wen, Xiaoan,Liu, Jun
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- And reclaims to clean rough synthesis method
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The invention belongs to the research field of bioactive substance preparation processes, and provides a synthesis method of lupeol. The lupeol is prepared by reduction reaction in the presence of a reducer and strong alkaline by taking betulinaldehyde or a 3-ester derivative thereof as raw materials. The method is less in experimental steps, simple to operate and high in yield, and the production cost of the lupeol is remarkably reduced.
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Paragraph 0011
(2017/08/25)
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- Lupeol-3-O-decanoate, a new triterpene ester from Cadaba farinosa Forssk. growing in Saudi Arabia
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A new triterpene ester (1) together with eight known compounds (2-9) were isolated from the leaves of Cadaba farinosa Forssk. Their chemical structures were established on the basis of physical, chemical, and spectroscopic methods (IR, 1D and 2D NMR, and mass spectral analyses) to be: lupeol-3-O-decanoate (1), lupeol (2), β-sitosterol (3), ursolic acid (4), 12-aminododecanoic (5), dillenetin-3-O-β-d-glucopyranoside (6), stachydrine (7), 3-hydroxy-stachydrine (8), and quercetin-3-O-β-d-glucopyranoside (9). That is the first report for the isolation of compound 5 from a plant source. Compounds 5, 6, and 9 were evaluated for their antioxidant activity.
- Al-Musayeib, Nawal M.,Mohamed, Gamal A.,Ibrahim, Sabrin R. M.,Ross, Samir A.
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p. 5297 - 5302
(2013/12/04)
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- Long-chain alkanoic acid esters of lupeol from Dorstenia harmsiana Engl. (Moraceae)
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In addition to lupeol (1a), three long-chain alkanoic acid esters of lupeol, in which two were new, were isolated from the hexane and ethyl acetate twigs extract of Dorstenia harmsiana Engl. (Moraceae). The structures of the new compounds were elucidated
- Poumale, Herve Martial P.,Awoussong, Kenzo Patrice,Randrianasolo, Rivoarison,Simo, Christophe Colombe F.,Ngadjui, Bonaventure Tchaleu,Shiono, Yoshihito
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experimental part
p. 749 - 755
(2012/10/08)
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- Isolation, identification, and biological evaluation of HIF-1-modulating compounds from Brazilian green propolis
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The tumor microenvironment is characterized by hypoxia, low-nutrient levels, and acidosis. A natural product chemistry-based approach was used to discover small molecules that modulate adaptive responses to a hypoxic microenvironment through the hypoxia-inducible factor (HIF)-1 signaling pathways. Five compounds, such as baccharin (3), beturetol (4), kaempferide (5), isosakuranetin (6), and drupanin (9), that modulate HIF-1-dependent luciferase activity were identified from Brazilian green propolis using reporter assay. Compounds 3, 9 and 5 reduced HIF-1-dependent luciferase activity. The cinnamic acid derivatives 3 and 9 significantly inhibited expression of the HIF-1α protein and HIF-1 downstream target genes such as glucose transporter 1, hexokinase 2, and vascular endothelial growth factor A. They also exhibited significant anti-angiogenic effects in the chick chorioallantoic membrane (CAM) assay at doses of 300 ng/CAM. On the other hand, flavonoids 4 and 6 induced HIF-1-dependent luciferase activity and expression of HIF-1 target genes under hypoxia. The contents (g/100 g extract) of the HIF-1-modulating compounds in whole propolis ethanol extracts were also determined based on liquid chromatography-electrospray ionization mass spectrometry as 1.6 (3), 14.2 (4), 4.0 (5), 0.7 (6), and 0.7 (9), respectively. These small molecules screened from Brazilian green propolis may be useful as lead compounds for the development of novel therapies against ischemic cardiovascular disease and cancer based on their ability to induce or inhibit HIF-1 activity, respectively.
- Hattori, Hisanori,Okuda, Kensuke,Murase, Tetsuji,Shigetsura, Yuki,Narise, Kosuke,Semenza, Gregg L.,Nagasawa, Hideko
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supporting information; experimental part
p. 5392 - 5401
(2011/10/31)
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- SACCHARIDE LUPANE DERIVATIVES, THEIR USE AND PHARMACEUTICAL COMPOSITIONS CONTAINING THESE DERIVATIVES
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This invention relates to saccharide lupane derivatives of general formula (I), wherein R denotes substituent independently selected from the group comprising hydrogen, hydroxy, amino, mercapto, alkyloxy, alkyl and saccharide group, R′ denotes substituent independently selected from the group comprising hydrogen, hydroxy, alkyl, carboxyl, acyl and saccharide group, wherein at least one of R and R′ contains a saccharide group. A further object relates to these compounds for use as medicaments and growth regulators. This invention further includes pharmaceutical compositions containing said derivatives.
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Page/Page column 16
(2009/09/05)
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- A short enantioselective total synthesis of the fundamental pentacyclic triterpene lupeol
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(Chemical Equation Presented) The first enantioselective synthesis of lupeol has been developed by applying two carefully crafted cation-π cyclization stages to generate the pentacyclic structure with complete stereocontrol. The synthesis (Scheme 1) is no
- Surendra, Karavadhi,Corey
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supporting information; experimental part
p. 13928 - 13929
(2009/12/25)
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- Synthesis of lupane-type saponins bearing mannosyl and 3,6-branched trimannosyl residues and their evaluation as anticancer agents
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The saponins modified with mono- or trimannosyl residues can provide a convenient means of delivering drugs to certain human cells via interactions with mannose receptors. In the study reported therein, we developed a convenient approach for the synthesis of 3-O-mannoside and branched trimannoside derivatives of the saponin lupeol and of C-28 acyl esters of 3-O-acetyl-betulinic acid bearing the same mannosyl entities. Lupeol and 3-O-acetyl-betulinic acid were mannosylated with tetra-O-benzoyl- or tetra-O-acetyl-α-d-mannopyranosyl trichloroacetimidates. De-esterification followed by regioselective dimannosylation of the unprotected monosaccharide derivatives with 2 equiv of tetra-O-benzoyl-α-d-mannopyranosyl trichloroacetimidate selectively yielded O-3,O-6-linked trimannosides. The cytotoxic activity of selected lupane-type saponins (derivatives of lupeol, betulinic acid, and betulin) toward normal human fibroblasts and various cancer cell lines was also compared.
- Cmoch, Piotr,Pakulski, Zbigniew,Swaczynova, Jana,Strnad, Miroslav
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p. 995 - 1003
(2008/09/20)
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- Lupeol ester from Clerodendrum phlomidis L.
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A new triterpene ester, together with tetratriacontanol and 24β-ethylcholesta-5,22E,25-triene-3β-ol, has been isolated from the aerial parts of Clerodendrum phlomidis L. Occurrence of a triterpene fatty acid ester lup-20(29)-en-3-triacontanoate in this plant is of taxonomic importance. Structures of all the isolated compounds have been established by spectroscopic and chemical studies.
- Pandey,Kaur,Malasoni,Gupta
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p. 470 - 472
(2008/09/21)
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- Methods of treating fungal infections using lupeol
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The invention is directed to methods of treating fungal and yeast infections using lupeol or solvates, hydrates, or clathrates thereof. The method also encompasses methods of treating fungal and yeast infections by administering to a mammal in need of such treatment a therapeutically effective amount of lupeol. Among the methods used include topical formulations for the improvement of skin appearance.
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- Methods of treating antifungal infections using lupeol
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The invention is directed to methods of treating fungal and yeast infections using lupeol or solvates, hydrates, or clathrates thereof. The method also encompasses methods of treating fungal and yeast infections by administering to a mammal in need of such treatment a therapeutically effective amount of lupeol. Among the methods used include topical formulations for the improvement of skin appearance.
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- Microwave assisted acetylation and deacetylation studies on the triterpenes isolated from Dysoxylum malabaricum and Dysoxylum beddomei
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Phytochemical investigations on the leaves of Dysoxylum malabaricum and Dysoxylum beddomei result in the isolation of a number of triterpenes. Acetylation and deacetylation studies on some of the representative triterpenes show appreciable rate enhancement and increase of yield in the presence of microwave radiation. Details of isolation of triterpenes, acetylation and deacetylation procedures and their results form the subject of the paper. Triterpenes of three skeletal types namely lupane, tirucallane and cycloartane are examined. All the triterpenes examined indicate an increase of cytotoxicity with acetylation.
- Jayakumar,Ajithabai,Santhosh,Veena,Nairt, Mangalam S.
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p. 429 - 431
(2007/10/03)
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- Synthesis of betulin derivatives and their protective effects against the cytotoxicity of cadmium
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The protecting effect of betulin against cadmium toxicity was investigated using 11 inds of analogues. It was elucidated by analyzing the analogue activities that both hydroxyl groups on C-3 and C-28 and the isopropenyl group on C-19 played important roles for expressing efficient activities. In addition, the cytotoxicity of betulin was also reduced by being functionalized using the above functional group. Copyright
- Hiroya, Kou,Takahashi, Taisuke,Miura, Nobuhiko,Naganuma, Akira,Sakamoto, Takao
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p. 3229 - 3236
(2007/10/03)
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- Triterpenes having human antifungal and antiyeast activity
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Methods of treating a fungal or yeast infection and of killing or inhibiting fungi or yeast are disclosed. The methods use derivatives of triterpenes that are abundant in birch bark and other plants. The triterpenes include betulin, allobetulin, and lupeol.
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- Triterpenes having antibacterial activity
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Methods of treating a bacterial infection and of killing or inhibiting bacteria are disclosed. The methods use derivatives of triterpenes that are abundant in birch bark and other plants. The triterpenes include betulin, allobetulin, and lupeol.
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- Arabidopsis thaliana LUP1 converts oxidosqualene to multiple triterpene alcohols and a triterpene diol
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lupeol lupeol, germanicol, synthase β-amyrin, taxasterol, oxidosqualene → ψ-taraxasterol, and 3,20-dihydroxylupane The Arabidopsis thaliana LUP1 gene encodes an enzyme that converts oxidosqualene to pentacyclic triterpenes. Lupeol and β-amyrin were previously reported as LUP1 products. Further investigation described here uncovered the additional products germanicol, taraxasterol, ψ-taraxasterol, and 3,20-dihydroxylupane. These results suggest that the 80 known C30H50O compounds that are structurally consistent with being oxidosqualene cyclase products may be derived from fewer than 80 enzymes and that some C30H52O2 compounds may be direct cyclization products of oxidosqualene.
- Segura, Michael J. R.,Meyer, Michelle M.,Matsuda, Seiichi P. T.
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p. 2257 - 2259
(2007/10/03)
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- Lichens and Fungi. XVIII. Extractives from Pseudocyphellaria rubella
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Twenty lupane triterpenoids including five (20RS)-epimeric pairs have been isolated from the chloroform extractives of the lichen Pseudocyphellaria rubella.The utility of g.c.-m.s. procedures in the structural elucidation of the extractives, some of which were complex mixtures is discussed.
- Corbett, R. Edward,Cong, Aimy N. T.,Holland, Patrick T.,Wilkins, Alistair L.
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p. 461 - 468
(2007/10/02)
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- REDUCTION OF KETONES TO EPIMERIC ALCOHOLS WITH POTASSIUM HYDROXIDE-DIETHYLENE GLYCOL
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Triterpenoid ketones have been reduced to epimeric alcohols on boiling with potassium hydroxide in diethylene glycol. α,β-unsaturated ketone furnished saturated epimeric alcohols.
- Pradhan, B. P.,Hassan, A.,Ray, T.
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p. 2513 - 2516
(2007/10/02)
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- A TRITERPENOIDAL SAPONIN FROM ROOTS OF ACANTHUS ILLICIFOLIUS
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Key Word Index - Acanthus illicifolius; Acanthaceae; saponin; 4)-β-D-glucuronopyranosyl(1-->3)>-3β-hydroxy-lup-20(29)-ene. A new triterpenoidal saponin has been isolated from the ethanolic extract of Acanthus illicifolius.It was shown to be 4)-β-D-glucuronopyranosyl(1-->3)>-3β-hydroxy-lup-20(29)-ene.
- Minocha, P. K.,Tiwari, K. P.
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p. 135 - 138
(2007/10/02)
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