545-47-1Relevant articles and documents
Pentacyclic triterpenes and naphthoquinones from Euclea divinorum
Mebe, Paul P.,Cordell, Geoffrey A.,Pezzuto, John M.
, p. 311 - 313 (1998)
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.
TRITERPENOIDS OF AMSONIA GRANDIFLORA
Wahyuono, Subagus,Hoffmann, Joseph J.,Jolad, Shivanand D.,Dentali, Steven J.
, p. 1213 (1987)
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.
Antibacterial activity of naphthoquinones and triterpenoids from Euclea natalensis root bark
Weigenand, Oliver,Hussein, Ahmed A.,Lall, Namrita,Meyer, Jacobus J. M.
, p. 1936 - 1938 (2004)
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.
Practical Synthesis of α-Amyrin, β-Amyrin, and Lupeol: The Potential Natural Inhibitors of Human Oxidosqualene Cyclase
Chen, Dongyin,Xu, Fengguo,Zhang, Pu,Deng, Jie,Sun, Hongbin,Wen, Xiaoan,Liu, Jun
, (2017/10/20)
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.
And reclaims to clean rough synthesis method
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Paragraph 0036-0041; 0053-0055, (2017/08/25)
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.
Lupeol-3-O-decanoate, a new triterpene ester from Cadaba farinosa Forssk. growing in Saudi Arabia
Al-Musayeib, Nawal M.,Mohamed, Gamal A.,Ibrahim, Sabrin R. M.,Ross, Samir A.
, p. 5297 - 5302 (2013/12/04)
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.
Long-chain alkanoic acid esters of lupeol from Dorstenia harmsiana Engl. (Moraceae)
Poumale, Herve Martial P.,Awoussong, Kenzo Patrice,Randrianasolo, Rivoarison,Simo, Christophe Colombe F.,Ngadjui, Bonaventure Tchaleu,Shiono, Yoshihito
experimental part, p. 749 - 755 (2012/10/08)
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
Isolation, identification, and biological evaluation of HIF-1-modulating compounds from Brazilian green propolis
Hattori, Hisanori,Okuda, Kensuke,Murase, Tetsuji,Shigetsura, Yuki,Narise, Kosuke,Semenza, Gregg L.,Nagasawa, Hideko
supporting information; experimental part, p. 5392 - 5401 (2011/10/31)
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.
SACCHARIDE LUPANE DERIVATIVES, THEIR USE AND PHARMACEUTICAL COMPOSITIONS CONTAINING THESE DERIVATIVES
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Page/Page column 16, (2009/09/05)
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.
A short enantioselective total synthesis of the fundamental pentacyclic triterpene lupeol
Surendra, Karavadhi,Corey
supporting information; experimental part, p. 13928 - 13929 (2009/12/25)
(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
