18172-67-3Relevant articles and documents
Isotopically Sensitive Branching as a Tool for Evaluating Multiple Product Formation by Monoterpene Cyclases
Wagschal, Kurt,Savage, Thomas J.,Croteau, Rodney
, p. 5933 - 5944 (1991)
The deuterated substrates geranyl pyrophosphate and geranyl pyrophosphate were employed to examine isotopically sensitive branching in the biosynthesis of monoterpene olefin isomers.By this method, (-)-α-pinene and (-)-β-pinene were shown to be synthesized via a common intermediate by a single cyclization enzyme from grand fir (Abies grandis), as were (-)-α-phellandrene and (-)-β-phellandrene by a single cyclase from lodgepole pine (Pinus contorta).Kinetic isotope effects were determined for the various deprotonations leading to the pinenes and phellandrenes.Key Words: Isotopically sensitive branching, monoterpene biosynthesis, monoterpene cyclase, resin biosynthesis, kinetic isotope effect.
Acorenone B: AChE and BChE inhibitor as a major compound of the essential oil distilled from the ecuadorian species niphogeton dissecta (Benth.) J.F. macbr
Calva, James,Bec, Nicole,Gilardoni, Gianluca,Larroque, Christian,Cartuche, Luis,Bicchi, Carlo,Montesinos, José Vinicio
, (2017/11/16)
This study investigated the chemical composition, physical proprieties, biological activity, and enantiomeric analysis of the essential oil from the aerial parts of Niphogeton dissecta (culantrillo del cerro) from Ecuador, obtained by steam distillation. The qualitative and quantitative analysis of the essential oil was realized by gas chromatographic and spectroscopic techniques (GC-MS and GC-FID). Acorenone B was identified by GC-MS and NMR experiments. The enantiomeric distribution of some constituents has been assessed by enantio-GC through the use of a chiral cyclodextrin-based capillary column. We identified 41 components that accounted for 96.46% of the total analyzed, the major components were acorenone B (41.01%) and (E)-β-ocimene (29.64%). The enantiomeric ratio of (+)/(-)-β-pinene was 86.9:13.1, while the one of (+)/(-)-sabinene was 80.9:19.1. The essential oil showed a weak inhibitory activity, expressed as Minimal Inhibitory Concentration (MIC), against Enterococcus faecalis (MIC 10 mg/mL) and Staphylococcus aureus (MIC 5 mg/mL). Furthermore, it inhibited butyrylcholinesterase with an IC50 value of 11.5 μg/mL. Pure acorenone B showed inhibitory activity against both acetylcholinesterase and butyrylcholinesterase, with IC50 values of 40.8 μg/mL and 10.9 μg/mL, respectively.
The first regio- and diastereoselective synthesis of homochiral perhydroimidazoisoxazoles via the 1,3-dipolar cycloaddition of imidazoline 3-oxides with (1S)-(-)-β-pinene
Coskun, Necdet,Tat, Fatma Tirli,Gueven, Oezden Oezel
, p. 1463 - 1467 (2007/10/03)
The 1,3-dipolar cycloaddition of imidazoline 3-oxides 1 with (1S)-(-)-β-pinene proceeds regio- and diastereoselectively to give homochiral perhydroimidazoisoxazole derivatives 3 in high yields in the cases of imidazoline 3-oxides 1a-e but in low yields in