Interaction of plant alkaloid, berberine, with zwitterionic and negatively charged phospholipid bilayers
Berberine exhibits many pharmacological activities e.g. antibacterial, anti-inflammatory, antiproliferative and apoptosis-inducing. Interaction of berberine with model membranes was studied for the first time using differential scanning calorimetry, fluorescence spectroscopy and turbidity measurements. Influence of berberine on thermotropic properties of bilayers formed from zwitterionic DMPC was insignificant, whereas in bilayers formed from negatively charged DMPG berberine reduced the temperature and cooperativity of main phospholipid phase transition. In higher concentrations berberine induced complex double-peak transition, with the new peak appearing in temperature higher than the original one. It suggested the interaction of the alkaloid with lipid headgroup region of the bilayer. Additionally, berberine quenched fluorescence of Prodan to a higher extent than Laurdan that pointed to stronger interaction with membrane segments close to its surface. Berberine-induced fluorescence quenching of both probes was more pronounced in DPPG than in DPPC bilayers. It was concluded that electrostatic interactions governed berberine association with model membrane.
If the inline PDF is not rendering correctly, you can download the PDF file here.
Bagatolli L. A. Parasassi T. Fidelio G. D. & Gratton E. (1999). A model for the interaction of 6-lauroyl-2-(N N-dimethylamino)naphthalene with lipid environments: implications for spectral properties. Photochem. Photobiol.70 557-564.
Budai M. Szabo Z. Szogyi M. & Grof P. (2003). Molecular interactions between DPPC and morphine derivatives: a DSC and EPR study. Int. J. Pharm.250 239-250.
Cao M. Liu M. Cao C. Xia Y. Bao L. Jin Y. Yang S. & Zhu C. (2010). A simple fluorescence quenching method for berberine determination using water-soluble CdTe quantum dots as probes. Spectrochim. Acta A75 1043-1046.
Freile M. L. Giannini F. Pucci G. Sturniolo A. Rodero L. Pucci O. Balzareti V. & Enriz R. D. (2003). Antimicrobial activity of aqueous extracts and of berberine isolated from Berberis heterophylla. Fitoterapia74 702-705.
Giri P. & Kumar G. S. (2010). Isoquinoline alkaloids and their binding with polyadenylic acid: potential basis of therapeutic action. Mini Rev. Med. Chem.10 568-577.
Gupta S. C. Kim J. H. Prasad S. & Aggarwal B. B. (2010). Regulation of survival proliferation invasion angiogenesis and metastasis of tumor cells through modulation of inflammatory pathways by nutraceuticals. Cancer Metastasis Rev.29 405-434.
Howes M-J. R. & Houghton P. J. (2003). Plants used in Chinese and Indian traditional medicine for improvement of memory and cognitive function. Pharmacol. Biochem. Behav.75 513-527.
Hu Y. J. Ou-Yang Y. Dai C. M. Liu Y. & Xiao X. H. (2010). Binding of berberine to bovine serum albumin: spectroscopic approach. Mol. Biol. Rep.37 3827-3832.
Huang C. Z. Feng P. Li Y. F. Tan K. J. & Wang H. Y. (2005). Adsorption of penicillin-berberine ion associates at a water/tetrachloromethane interface and determination of penicillin based on total internal-reflected resonance light scattering measurements. Anal. Chim. Acta538 337-343.
Imanshahidi M. & Hosseinzadeh H. (2008). Pharmacological and Therapeutic Effects of Berberis vulgaris and its Active Constituent Berberine. Phytother. Res.22 999-1012.
Ivanovska N. & Philipov S. (1996). Study on the anti-inflammatory action of Berberis vulgaris root extract alkaloid fractions and pure alkaloid. Int. J. lmmunopharm.8 553-561.
Iwazaki R. S. Endo E. H. Ueda-Nakamura T. Nakamura C. V. Garcia L. B. & Filho B. P. (2010). In vitro antifungal activity of the berberine and its synergism with fluconazole. Antonie Van Leeuwenhoek97 201-205.
Jain M. K. & Wu N. M. (1977). Effect of small molecules on the dipalmitoyl lecithin liposomal bilayer: III. Phase transition in lipid bilayer J. Membr. Biol.34 157-201.
Jantova S. Cipak L. & Letasiova S. (2007). Berberine induces apoptosis through a mitochondrial/caspase pathway in human promonocytic U937 cells. Toxicol. In Vitro21 25-31.
Krasnowska E. K. Gratton E. & Parasassi T. (1998). Prodan as a Membrane Surface Fluorescence Probe: Partitioning between Water and Phospholipid Phases. Biophys. J.74 1984-1993.
Kulkarni S. K. & Dhir A. (2010). Berberine: a plant alkaloid with therapeutic potential for central nervous system disorders. Phytother. Res.24 317-324.
Kuo C. Chi C. & Liu T. (2004). The anti-inflammatory potential of berberine in vitro and in vivo. Cancer Lett.203 127-137.
Liu Z. Liu Q. Xu B. Wu J. Guo C. Zhu F. Yang Q. Gao G. Gong Y. & Shao C. (2009). Berberine induces p53-dependent cell cycle arrest and apoptosis of human osteosarcoma cells by inflicting DNA damage. Mutat. Res.662 75-83.
Morrow M. R. Huschilt J. C. & Davis J. H. (1985). Simultaneous modeling of phase and calorimetric behavior in an amphiphilic peptide/phospholipid model membrane. Biochemistry24 5396-5406.
Parasassi T. De Stasio G. d'Ubaldo A. & Gratton E. (1990). Phase fluctuation in phospholipid membranes revealed by Laurdan fluorescence Biophys. J.57 1179-1186.
Rackova L. Majekova M. Kostalova D. & Stefek M. (2004). Antiradical and antioxidant activities of alkaloids isolated from Mahonia aquifolium. Structural aspects. Bioorg. Med. Chem.12 4709-4715.
Scazzocchio F. Cometa M. F. Tomassini L. & Palmery M. (2001). Antibacterial activity of Hydrastis canadensis extract and its major isolated alkaloids. Planta Med.67 561-564.
Walrant A. Correia I. Jiao C. Y. Lequin O. Bent E. H. Goasdoue N. Lacombe C. Chassaing G. Sagan S. & Alves I. D. (2011). Different membrane behaviour and cellular uptake of three basic arginine-rich peptides. Biochim. Biophys. Acta1808 382-393.
Wang N. Feng J. Zhu M. Tsang C-M. Man K. Tong Y. & Tsao S-W. (2010). Berberine induces autophagic cell death and mitochondrial apoptosis in liver cancer cells: The cellular mechanism. J. Cell. Biochem.111 1426-1436.
Yadav R. C. Kumar G. S. Bhadra K. Giri P. Sinha R. Pal S. & Maiti M. (2005). Berberine a strong polyriboadenylic acid binding plant alkaloid: spectroscopic viscometric and thermodynamic study. Bioorg. Med. Chem.13 165-174.