64090-86-4Relevant articles and documents
Arabidopsis thaliana LUP1 converts oxidosqualene to multiple triterpene alcohols and a triterpene diol
Segura, Michael J. R.,Meyer, Michelle M.,Matsuda, Seiichi P. T.
, p. 2257 - 2259 (2000)
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.
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
Preventive effect of taraxasteryl acetate from Inula britannica subsp. japonica on experimental hepatitis in vivo
Iijima,Kiyohara,Tanaka,Matsumoto,Cyong,Yamada
, p. 50 - 53 (2007/10/02)
The survival rate for acute hepatic failure induced by Propionibacterium acnes and lipopolysaccharide (LPS) was increased when a hot water extract from the flowers of Inula britannica h. subsp. japonica Kitam. was injected into the experimental hepatitis mice, and anti-hepatitis substances could be extracted with CHCl3. The CHCl3 extract from I. britannica was fractionated and anti-hepatitis fractions IB-3-2 and IB3-3 were obtained. IB-3-3 had the most potent antihepatitis activity among the fractions but further purification of the active compound was not achieved because of the low yield. IB-3-2 contained only one substance which was identified to be taraxasteryl acetate by 1H- and 13C-NMR and MS. Taraxasteryl acetate showed potent preventive activity against acute hepatic failure induced by P. acnes and LPS in a dose-dependent manner, however deacetylation and modification of the olefinic bonds significantly decreased the anti-hepatitis activity of taraxasteryl acetate. Taraxasteryl acetate also inhibited the increment of plasma transaminase on acute hepatic failure induced by carbon tetrachloride (CCl4) or D-galactosamine. From a histological study it appeared that degeneration and necrosis, which were observed in the liver from CCl4 mice, were not found in the liver cells from taraxasteryl acetate treated mice. These results indicates that taraxasteryl acetate shows preventive effects on experimental hepatitis caused by either immunologically induced injuries or hepatotoxic chemicals.
