Membrane-related effects underlying the biological activity of the anthraquinones emodin and barbaloin

Experimental and theoretical studies of emodin interacting with a lipid bilayer of DMPC

“…Therefore, although both species of Emodin, EMH and EM − , locate inside the bilayer in the same region, near the glycerol group, the lipid bilayer is more affected by the EM − compared with the EMH. These disorders caused by Emodin should cause distinct effects on lipid bilayer including the disruptive effects that have been previously reported in some phospholipid bilayer (Alves et al 2004;Huang et al 2006). Further, the diversity of biological activities attributed to Emodin, such as antibacterial, anti-inflammatory, antiviral and anticancer cell migration and invasion may be also related to its disruptive effect on biological membranes.…”

“…In previous studies, UV/Visible absorption and fluorescence spectroscopy have been applied as analytical tools to study the interaction of Emodin with solvents (Pal and Jana 1993;Nguyen et al 2008;Sevilla et al 2009;da Cunha et al 2014), with biological environments like human serum albumin (HSA) (Fabriciova et al 2004;Vargas et al 2004), DNA (Wang et al 2006;Saito et al 2012;Bi et al 2008), phospholipid bilayer (Alves et al 2004) and with other environments Fig. 1 Chemical structure and atomic numbering of Emodin in its neutral form (EMH) like porous silicon (Hernandez et al 2012), silver nanoparticles (Sevilla et al 2009(Sevilla et al , 2010 and some metal ions (Pal and Jana 1993).…”

“…However, only one study has investigated the properties of neutral Emodin in phospholipid membranes (Alves et al 2004). Much of what is known about the behavior of Emodin in lipid membranes comes from an experimental study by Alves et al (2004), reporting an extensive and detailed spectroscopic and thermoanalytical study of its neutral form in model membranes.…”

“…However, only one study has investigated the properties of neutral Emodin in phospholipid membranes (Alves et al 2004). Much of what is known about the behavior of Emodin in lipid membranes comes from an experimental study by Alves et al (2004), reporting an extensive and detailed spectroscopic and thermoanalytical study of its neutral form in model membranes. In this work, the authors used fluorescence spectroscopy to determine a phospholipid/water partition coefficient, K p of (14 ± 2) × 10 3 for neutral Emodin in the DMPC bilayer, indicating that this molecule exhibits high affinity for phospholipid membranes.…”

Barbaloin: A concise report of its pharmacological and analytical aspects

“…Barbaloin showed affinity for phospholipid membranes whereas barbaloin stabilized lamellar structures. Barbaloin showed antiviral activity and may be used as a potential candidate for an alternative for antimicrobial, pharmaceutical or cosmetic applications [4] . …”