100016-94-2Relevant academic research and scientific papers
Sesamolinol glucoside, disaminyl ether, and other lignans from sesame seeds
Grougnet, Raphael,Magiatis, Prokopios,Laborie, Helene,Lazarou, Despina,Papadopoulos, Athanasios,Skaltsounis, Alexios-Leandros
, p. 108 - 111 (2012)
The application of a procedure based on XAD-4 adsorption resin permitted the obtainment of an enriched polyphenolic extract from Sesamum indicum seeds. Chemical analysis of the obtained extract led to the identification of 12 lignans. Among them, 2 lignans, (+)-sesamolinol-4′-O-β-d-glucoside and disaminyl ether, are reported for the first time as natural compounds. Their structure has been determined by spectroscopic methods, mainly by the application of one-dimensional (1D) and two-dimensional (2D) nuclear magnetic resonance (NMR) techniques [heteronuclear multiple-quantum coherence (HMQC), heteronuclear multiple-bond correlation (HMBC), and nuclear Overhauser effect spectrometry (NOESY)] and mass spectroscopy. The isolated compounds were evaluated for their antimutagenic activity. Among the tested lignans, the most active lignan was found to be sesamolin, followed by sesamolinol and samin, against H2O2. Additionally, some of the tested lignans showed desmutagenic activity against benzo[a]pyrene (BaP).
Oxygen insertion in Sesamum indicum furanofuran lignans. Diastereoselective syntheses of enzyme substrate analogues
Marchand, Patrice A.,Zajicek, Jaroslav,Lewis, Norman G.
, p. 840 - 849 (2007/10/03)
The furofuran lignans in sesame seed have an unusual oxygen insertion between their furan and aryl rings. In our continuing investigations on the isolation and characterization of the enzyme(s) involved, the diastereoselective syntheses of various substrate analogues for the oxygen insertion step were developed for future substrate specificity and inhibitor studies. This synthetic strategy also provided entry to so-called furofuranone epoxy-lignans, such as salicifoliol from Bupleurum sp., and acuminatolide from Helichrysum sp.
