30300-37-9Relevant academic research and scientific papers
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
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 (2007/10/03)
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.
