title: Modifications of the chemical structure of phenolics differentially affect physiological activities in pulvinar cells of Mimosa pudica L. II. Influence of various molecular properties in relation to membrane transport.
abstract: Early prediction of compound absorption by cells is of considerable importance in the building of an integrated scheme describing the impact of a compound on intracellular biological processes. In this scope, we study the structure-activity relationships of several benzoic acid-related phenolics which are involved in many plant biological phenomena (growth, flowering, allelopathy, defense processes). Using the partial least squares (PLS) regression method, the impact of molecular descriptors that have been shown to play an important role concerning the uptake of pharmacologically active compounds by animal cells was analyzed in terms of the modification of membrane potential, variations in proton flux, and inhibition of the osmocontractile reaction of pulvinar cells of Mimosa pudica leaves. The hydrogen bond donors (HBD) and hydrogen bond acceptors (HBA), polar surface area (PSA), halogen ratio (Hal ratio), number of rotatable bonds (FRB), molar volume (MV), molecular weight (MW), and molar refractivity (MR) were considered in addition to two physicochemical properties (logD and the amount of non-dissociated form in relation to pKa). HBD + HBA and PSA predominantly impacted the three biological processes compared to the other descriptors. The coefficient of determination in the quantitative structure-activity relationship (QSAR) models indicated that a major part of the observed seismonasty inhibition and proton flux modification can be explained by the impact of these descriptors, whereas this was not the case for membrane potential variations. These results indicate that the transmembrane transport of the compounds is a predominant component. An increasing number of implicated descriptors as the biological processes become more complex may reflect their impacts on an increasing number of sites in the cell. The determination of the most efficient effectors may lead to a practical use to improve drugs in the control of microbial attacks on plants.
authors.affiliation: IC2MP (Institut de Chimie des Milieux et des Matériaux de Poitiers), UMR CNRS 7285, Université de Poitiers, 4 rue Michel Brunet, TSA 51106, F-86073, Poitiers cedex 9, France.
authors.forename: Françoise
authors.initials: F
authors.lastname: Rocher
authors.affiliation: Laboratoire EBI (Écologie et Biologie des Interactions), UMR CNRS 7267, Équipe SEVE (Sucres, Échanges Végétaux, Environnement), Université de Poitiers, 3 rue Jacques Fort, TSA 51106, F-86073, Poitiers cedex 9, France.
authors.forename: Gabriel
authors.initials: G
authors.lastname: Roblin
authors.affiliation: IC2MP (Institut de Chimie des Milieux et des Matériaux de Poitiers), UMR CNRS 7285, Université de Poitiers, 4 rue Michel Brunet, TSA 51106, F-86073, Poitiers cedex 9, France. jfcholle@univ-poitiers.fr.
authors.forename: Jean-François
authors.initials: JF
authors.lastname: Chollet
mesh_terms: D000818:Animals; D001686:Biological Phenomena; D001692:Biological Transport; D002462:Cell Membrane / Q000187:drug effects / Q000502:physiology*; D006860:Hydrogen Bonding; D016018:Least-Squares Analysis; D008564:Membrane Potentials / Q000187:drug effects / Q000502:physiology; D031298:Mimosa / Q000166:cytology / Q000187:drug effects / Q000378:metabolism / Q000502:physiology*; D008962:Models, Theoretical; D010636:Phenols / Q000737:chemistry* / Q000378:metabolism; D011522:Protons; D018516:Pulvinus / Q000166:cytology / Q000187:drug effects / Q000378:metabolism / Q000502:physiology*; D021281:Quantitative Structure-Activity Relationship; D020156:Salicylic Acid / Q000494:pharmacology
chemical_list: D010636:Phenols; D011522:Protons; D020156:Salicylic Acid
keywords: H+ fluxes; Membrane potential; Mimosa pudica; Phenolics; Salicylic acid; Seismonasty; Transmembrane transport
references.citation: FEBS Lett. 2007 May 25;581(12):2337-47
references.pmid: 17434488
references.citation: Bioorg Med Chem. 2011 Apr 15;19(8):2615-24
references.pmid: 21458999
references.citation: Eur J Med Chem. 2011 Jan;46(1):218-28
references.pmid: 21112128
references.citation: Pharm Res. 2014 Apr;31(4):1002-14
references.pmid: 24306326
references.citation: Annu Rev Phytopathol. 2009;47:177-206
references.pmid: 19400653
references.citation: Plant Physiol. 1988 Mar;86(3):803-10
references.pmid: 16665992
references.citation: J Pharm Biomed Anal. 2007 Jan 4;43(1):119-30
references.pmid: 16859855
references.citation: J Med Chem. 1998 Dec 3;41(25):4939-49
references.pmid: 9836611
references.citation: Plant Physiol Biochem. 2013 Nov;72:1-20
references.pmid: 23774057
references.citation: J Appl Bacteriol. 1985 Oct;59(4):299-302
references.pmid: 3905741
references.citation: Tsitologiia. 2010;52(3):211-8
references.pmid: 20429298
references.citation: J Membr Biol. 2013 Apr;246(4):287-96
references.pmid: 23417063
references.citation: Plant Cell Physiol. 2014 Aug;55(8):1511-9
references.pmid: 24928219
references.citation: Proc Natl Acad Sci U S A. 1989 Apr;86(7):2214-8
references.pmid: 16594020
references.citation: J Pharm Pharm Sci. 2002 Sep-Dec;5(3):258-66
references.pmid: 12553894
references.citation: J Exp Bot. 2013 Apr;64(7):1829-36
references.pmid: 23487303
references.citation: J Exp Bot. 2008;59(9):2317-24
references.pmid: 18515832
references.citation: Mol Pharm. 2007 Jul-Aug;4(4):556-60
references.pmid: 17530776
references.citation: Pest Manag Sci. 2004 Nov;60(11):1063-72
references.pmid: 15532679
references.citation: Adv Appl Bioinform Chem. 2009;2:57-70
references.pmid: 21918616
references.citation: Front Plant Sci. 2015 Oct 16;6:859
references.pmid: 26528317
references.citation: Plant Cell Environ. 2007 Mar;30(3):249-57
references.pmid: 17263772
references.citation: Curr Opin Plant Biol. 2004 Aug;7(4):472-9
references.pmid: 15231272
references.citation: Plant Cell Environ. 2010 Feb;33(2):163-73
references.pmid: 19895396
references.citation: J Med Chem. 2002 Jun 6;45(12):2615-23
references.pmid: 12036371
references.citation: J Invertebr Pathol. 1997 Nov;70(3):209-13
references.pmid: 9367728
references.citation: Plant Physiol Biochem. 2014 Nov;84:240-250
references.pmid: 25306527
references.citation: Planta. 2007 Jun;226(1):203-14
references.pmid: 17226028
references.citation: Pest Manag Sci. 2005 Apr;61(4):377-82
references.pmid: 15751009
references.citation: Science. 1972 Oct 6;178(4056):63-4
references.pmid: 5070517
references.citation: Adv Drug Deliv Rev. 2001 Mar 1;46(1-3):3-26
references.pmid: 11259830
references.citation: Plant Physiol. 2006 Aug;141(4):1684-93
references.pmid: 16778012
references.citation: Chembiochem. 2004 May 3;5(5):571-89
references.pmid: 15122630
references.citation: Eur J Pharm Sci. 2014 Jun 16;57:173-99
references.pmid: 24215735
references.citation: Pharm Res. 1997 May;14 (5):568-71
references.pmid: 9165525
references.citation: Plant Physiol. 2009 Aug;150(4):2081-91
references.pmid: 19493970
references.citation: J Med Chem. 2000 Oct 5;43(20):3714-7
references.pmid: 11020286
references.citation: J Mol Graph Model. 2003 Jan;21(4):273-87
references.pmid: 12479927
references.citation: Plant Physiol Biochem. 2014 Jan;74:125-32
references.pmid: 24292275