1724-19-2Relevant academic research and scientific papers
ISOLATION OF LANOSTA-8,25-DIEN-3β-OL FROM THE FUNGUS FOMES FASTUOSUS
Jain, Amolak C.,Gupta, Sushil K.
, p. 2392 - 2394 (1984)
A new lanostane triterpene has been isolated from the fungus Fomes fastuosus which causes wood-rotting of Emblica officinalis.The compound is assigned the structure lanosta-8,25-dien-3β-ol on the basis of spectral data and correlation with lanosterol. - Key Word Index: Fomes fastuosus; Polyporaceae; wood-rotting fungus on Emblica officinalis; lanosta-8,25-dien-3β-ol.
Synthesis and antimicrobial activity of novel oxysterols from lanosterol
Shingate, Bapurao B.,Hazra, Braja G.,Salunke, Deepak B.,Pore, Vandana S.,Shirazi, Fazal,Deshpande, Mukund V.
, p. 11155 - 11163 (2014/01/06)
Chemically diverse oxysterols and their synthetic manipulations were carried out from variety of Δ8(9)-lanosterol derivatives and evaluated for their in vitro antimicrobial activities. Most of the synthesized oxysterols exhibited significant antifungal activity against the tested strains.
Approach for expanding triterpenoid complexity via divergent Norrish-Yang photocyclization
Ignatenko, Vasily A.,Tochtrop, Gregory P.
, p. 3821 - 3831 (2013/06/26)
Triterpenoids comprise a very diverse family of polycyclic molecules that is well-known to possess a myriad of medicinal properties. Therefore, triterpenoids constitute an attractive target for medicinal chemistry and diversity-oriented synthesis. Photochemical transformations provide a promising tool for the rapid, green, and inexpensive generation of skeletal diversity in the construction of natural product-like libraries. With this in mind, we have developed a diversity-oriented strategy, whereby the parent triterpenoids bryonolic acid and lanosterol are converted to the pseudosymmetrical polyketones by sequential allylic oxidation and oxidative cleavage of the bridging double bond at the B/C ring fusion. The resultant polyketones were hypothesized to undergo divergent Norrish-Yang cyclization to produce unique 6/4/8-fused triterpenoid analogues. The subtle differences between parent triterpenoids led to dramatically different spatial arrangements of reactive functionalities. This finding was rationalized through conformational analysis to explain unanticipated photoinduced pinacolization, as well as the regio- and stereochemical outcome of the desired Norrish-Yang cyclization.
1H and 13C NMR Assignments for Lanostan-3β-ol Derivatives: Revised Assignments for Lanosterol
Emmons, Gary T.,Wilson, William K.,Schroepfer, George J. Jr
, p. 1012 - 1024 (2007/10/02)
1H and 13C NMR assignments are presented for 30 oxygenated lanostane derivatives, including lanosterol, dihydrolanosterol, 7-ketolanosterol, agnosterol, 24,25-epoxylanosterol, 8α,9α-epoxylanostan-3β-ol, three 15-oxygenated derivatives of lanost-7-en-3β-ol, lanostane-3β,7α-diol, lanostane-3B,9α-diol and their acetates.These assignments, which were largely determined by a combination of DEPT, one-bond and long-range 13C-1H chemical shift correlation and lanthanide-induced shift experiments, are not dependent on previously reported assignments, several of which were found to be incorrect. 1H and 13C acetylation shifts for lanostan-3β-ols were sufficiently invariant among the sterols studied that they were useful for assigning carbons in rings A and B.The acetylation shifts reported for lanostan-3β-ols were extended and partially revised.-- Key Words 1H and 13C NMR Oxygenated lanostane derivatives Spectral assignment Lanthanide-induced shifts Long-range HECTOR Acetylation shifts
CYCLOROYLENOL, A CYCLOPROPANE CONTAINING EUPHOID FROM EUPHORBIA ROYLEANA
Vijaya, S. Bhat,Vimal, S. Joshi,Dwipin, D. Nanavati
, p. 5207 - 5210 (2007/10/02)
Cycloroylenol, a new tetracyclictriterpene in the latex of Euphorbia royleana Boiss is shown to have structure (1a)
