Binding of the pepper alkaloid piperine to bovine beta-lactoglobulin: circular dichroism spectroscopy and molecular modeling study.
28 Dec 2005-Journal of Agricultural and Food Chemistry (American Chemical Society)-Vol. 53, Iss: 26, pp 10179-10185
TL;DR: This work demonstrated reversible, non-covalent association of piperine with bovine beta-lactoglobulin (BLG), the major whey protein in milk, in the first demonstration of its interaction with a mammalian protein.
Abstract: The pepper alkaloid piperine is a nontoxic, natural dietary compound with a broad range of physiological activity. The present work is the first demonstration of its interaction with a mammalian protein. Circular dichroism (CD) spectroscopy was used to reveal and analyze the binding of piperine to a lipocalin protein. Induced CD spectra measured in pH 7.7 phosphate buffer at 37 degrees C demonstrated reversible, non-covalent association of piperine with bovine beta-lactoglobulin (BLG), the major whey protein in milk. The binding parameters (K(a) approximately 8 x 10(4) M(-1), n = 0.8) determined from the CD titration data showed no significant differences between the piperine binding properties of the two main genetic variants of BLG (A and B). The vanishing extrinsic CD signal obtained upon acidification of the piperine-BLG sample solution (Tanford transition) suggested that the ligand binds in the central hydrophobic cavity of the beta-barrel. The cavity binding concept was further supported by a CD displacement experiment using palmitic acid, the well-known hydrophobic ligand of BLG. Molecular docking calculations showed that piperine can be efficiently accommodated within the calyx of BLG. Additional molecular modeling calculations indicated that the beta-barrel of human tear lipocalin, human serum retinol binding protein, and human neutrophil gelatinase associated lipocalin might also accommodate a piperine molecule.
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TL;DR: An overview of various bioactive ingredients which act as nutraceuticals (carbohydrates, lipids, edible flowers, alkaloids, medicinal plants, etc.) and their role in health benefits has been discussed and further application of nutr pharmaceuticals in various diseases prevention has been also discussed.
Abstract: Nutraceuticals are dietary supplements, utilized to ameliorate health, delay senescence, prevent diseases, and support the proper functioning of the human body. Currently, nutraceuticals are gaining substantial attention due to nutrition and therapeutic potentials. Based on their sources, they are categorized as dietary supplements and herbal bioactive compounds. The global market for nutraceutical is huge i.e. approximately USD 117 billion. Herbal nutraceutical helps in maintaining health and promoting optimal health, longevity, and quality of life. Studies have shown promising results of nutraceuticals to treat several diseases, such as cancer, neurodegenerative diseases, cardiovascular diseases, etc. In the present review, an overview of various bioactive ingredients that act as nutraceuticals (carbohydrates, lipids, edible flowers, alkaloids, medicinal plants, etc.) and their role in health benefits, has been discussed. Further application of nutraceuticals in the prevention of various diseases has also been discussed.
102 citations
TL;DR: It is shown that lactoglobulin binds also 8‐ and 10‐carbon caprylic and capric acids, however with lower affinity, and different location of ligands in the binding site indicates that competition between polar and hydrophobic interactions is an important factor determining position of the ligand in β‐barrel.
Abstract: Lactoglobulin is a natural protein present in bovine milk and common component of human diet, known for binding with high affinity wide range of hydrophobic compounds, among them fatty acids 12–20 carbon atoms long. Shorter fatty acids were reported as not binding to β-lactoglobulin. We used X-ray crystallography and fluorescence spectroscopy to show that lactoglobulin binds also 8- and 10-carbon caprylic and capric acids, however with lower affinity. The determined apparent association constant for lactoglobulin complex with caprylic acid is 10.8 ± 1.7 × 103 M−1, while for capric acid is 6.0 ± 0.5 × 103 M−1. In crystal structures determined with resolution 1.9 A the caprylic acid is bound in upper part of central calyx near polar residues located at CD loop, while the capric acid is buried deeper in the calyx bottom and does not interact with polar residues at CD loop. In both structures, water molecule hydrogen-bonded to carboxyl group of fatty acid is observed. Different location of ligands in the binding site indicates that competition between polar and hydrophobic interactions is an important factor determining position of the ligand in β-barrel. Copyright © 2010 John Wiley & Sons, Ltd.
102 citations
Cites background from "Binding of the pepper alkaloid pipe..."
...LGB for many years has been considered as a potential carrier protein for different hydrophobic ligands (Muresan et al., 2001; Zsila et al., 2005; Mohammadi et al., 2009)....
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10 Dec 2013
TL;DR: Alkaloid--secrets of life , Alkaloids--sec secrets of life, کتابخانه دیجیتال جندی شاپور اهواز
Abstract: Alkaloids--secrets of life , Alkaloids--secrets of life , کتابخانه دیجیتال جندی شاپور اهواز
99 citations
TL;DR: The binding of the aglycones of phenolic compounds to bovine and reindeer beta-lactoglobulins using fluorescence quenching implicated that betaLG could act as a binder or carrier for Phenolic compounds in acidic, basic, or neutral conditions and that the ligand/betaLG complex can remain stable during storage.
Abstract: In plant-based food, phenolic compounds usually do not exist in their native form, but as esters, glycosides, or polymers. The native forms, however, require deglycosylation for their intestinal absorption, and aglycone has been considered to be the potential health-protecting/promoting form. The binding of the aglycones of phenolic compounds to bovine and reindeer β-lactoglobulins (βLG) using fluorescence quenching was studied. The effects of pH and storage were also studied. Of the compounds investigated, the majority of flavones, flavonols, flavanones, and isoflavones were bound to βLG. In the pH studies, no significant effects were found. The fact that the phenolic compounds were not released at pH 2 might indicate that they bind to an external part rather than to the central cavity. Studies implicated that βLG could act as a binder or carrier for phenolic compounds in acidic, basic, or neutral conditions and that the ligand/βLG complex can remain stable during storage.
97 citations
TL;DR: Systematic changes of entropic component indicate important role of water in binding process and lauric, myristic and palmitic acid complexes revealing systematic decrease of enthalpic and increase of entropy component of ΔG with elongation of aliphatic chain.
78 citations
References
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TL;DR: The lipocalins are part of a larger protein superfamily: the calycins, which includes the fatty acid binding proteins, avidins, a group of metalloproteinase inhibitors, and triabin, and are characterised by a similar structure and by the conservation of a remarkable structural signature.
832 citations
TL;DR: It is proposed that β -LG, over-expressed in the lactating mammary gland of many, but not all, species, is primarily an important source of amino acids for the offspring of those animals that produce it, but that this function arose by gene duplication from the physiologically essential glycodelin.
639 citations
TL;DR: This chapter presents computation and analysis of protein circular dichroism (CD) spectra, and it is found that the CD spectrum of the typical β sheet has a negative band near 215-nm and a positive band near 198 nm.
Abstract: Publisher Summary This chapter presents computation and analysis of protein circular dichroism (CD) spectra. The origins of electronic CD in proteins, theoretical methods for computing protein CD, and empirical analysis of CD for estimating structural composition of proteins are described. The phenomenon of CD involves the absorption of light and it can be considered as a special type of absorption spectroscopy. The CD spectra of proteins are generally divided into three wavelength ranges, based on the energy of the electronic transitions that dominate in the given range. The basic approach used to compute the CD of complex systems, such as proteins and nucleic acids, is the divide and conquer approach. In addition to the isotropic atomic polarizabilities, the anisotropic polarizability of the first electrically allowed peptide transition was included in the dipole interaction model for protein CD calculations. Polarizability anisotropy data for simple amides were used for obtaining polarizability parameters. It is found that the CD spectrum of the typical β sheet has a negative band near 215-nm and a positive band near 198 nm.
481 citations
TL;DR: The structures of the trigonal crystal form of bovine beta-lactoglobulin variant A at pH 6.2, 7.1, and 8.2 have been determined by X-ray diffraction methods and provide a structural basis for a variety of pH-dependent chemical, physical, and spectroscopic phenomena, collectively known as the Tanford transition.
Abstract: The structures of the trigonal crystal form of bovine β-lactoglobulin variant A at pH 6.2, 7.1, and 8.2 have been determined by X-ray diffraction methods at a resolution of 2.56, 2.24, and 2.49 A, respectively. The corresponding values for R (Rfree) are 0.192 (0.240), 0.234 (0.279), and 0.232 (0.277). The C and N termini as well as two disulfide bonds are clearly defined in these models. The glutamate side chain of residue 89 is buried at pH 6.2 and becomes exposed at pH 7.1 and 8.2. This conformational change, involving the loop 85−90, provides a structural basis for a variety of pH-dependent chemical, physical, and spectroscopic phenomena, collectively known as the Tanford transition.
457 citations
TL;DR: Administration of alcoholic extract of Piper longum as well as piperine could inhibit the solid tumor development in mice induced with DLA cells and increase the life span of mice bearing Ehrlich ascites carcinoma tumor to 37.3 and 58.8%, respectively.
442 citations