A natural undecaprenol and its influence on the biochemical reactions of cotton seedling nuclei

Abstract

UDC 631.523A method has been developed for isolating polyprenolsfrom the leaves of cotton plants of lines L-463, L-501, and L-4. The influence of an undecaprenol on the level of biosynthesis of the proteins of the nuclei of cotton seedlings has been studied in vivo and in vitro. It has been found that they double the level of biosynthesis nuclear proteins when the seeds are first wetted in a O. 1% solution.Polyprenols, which belong to the class of natural polyisoprenoids, are distributed in the green parts of many plants. They have the general formula H-(CH2-C(CH 3) = CH-CH2)n-OH, where the number of isoprenoid residues (n) varies from one plant family to another (for example, n = 11-13 for the cotton plant).In the leaves of various species of trees polyprenol is found in the form of esters with acetic acid [1] and with higher fatty acids [2]. Plants of different families have different compositions of their polyprenols: in broad-leaved species of trees the number of isoprene units in the molecular chain ranges from 6 to 12 [3, 41 and in conifers from 10 to 20 [1, 5]. The amount of polyprenols varies according to the phase of development of the leaves, from 0.08% (in June) to 1.25% (in September).The interest in polyprenols that has arisen in recent years is due mainly to the important role that they play as lipophilic precursors of sugars in the biosynthesis of bacterial polysaccharides and glycoproteins [7]. We have recently discovered a capacity of polyprenols for opening the Ca 2+ channels of bilayer membranes [8].The synthesis of polyprenols is a multistage process [4, 5]. The finding of new natural sources will open up prospects for the creation from them of drugs and other agents with a high penetrating capacity --for example, plant-protecting agents with improved membrane properties.It must be mentioned that the biological function of endogenous polyprenols still remains unclear, although reviews have appeared both on their synthesis [9] and on their biological activity [10].In the present paper we give results on the isolation of polyprenols from the leaves of cotton plants of lines L-463, L-501, and L-4, in which their level amounts to 1-3% of the air-dry mass, and also on the influence of undecaprenol on the biochemical reactions of cotton seedling nuclei.Undecaprenol predominated in all the cotton plant lines (Table 1). The undecaprenol:dodecaprenol ratio was 2:1 for L-501 and L-4 and almost 3:1 for L-463.From the leaves of an L-4 cotton plant we succeeded in isolating undecaprenol with a purity greater than 98 %, as was confirmed by the results of physical methods of analysis. Its mass spectrum included the peaks of the molecular ion with m/z 766 (C55H900) and fragments with m/z 748 (M + -H20) and 698 (M + -68).The following signals were observed in the PMR spectrum: two singlets at 1.62 and 1.54 ppm from cis-and transmethyl groups in a ratio of 2:1, a multiplet in the 1.90-2.05 ppm region with its center at 1.96 ppm from the methylene groups of the isoprenoid chain, a doublet with its center at 3....

Acylation of Grape Leaves Polyprenols

“…Condition of HPLC analysis for determining ratio of polyprenyl homologues was as in [9], eluent -mixture of methanol with acetone (1:3 volume). Polyprenols which were isolated from Cotton leaves used as standard samples [12].…”

“…Molar ratio of acylating agents a little exceed of polyprenols in these cases. A reaction course checked on ТLC (each 1 minute) in solvent system: benzene -ethyl acetate 24:1, on plates Sorbfil (10x10) by comprising with standard sample of polyprenols, which was isolated from cotton leaves [12]. Corresponding spots were determined for identify.…”

Polyprenols from Althaea armeniaca leaves

“…The PP were identified chemically by comparing results of physicochemical analysis (IR and PMR spectra) with the literature [7,8] and TLC (benzene:ethylacetate 24:1) with iodine vapor as the detector. Ground leaves of various particle size (0.5-1.0, 2.0-3.0, 4.0-5.0, and 6.0-7.0 mm) were extracted in order to determine the optimum conditions for extracting compounds from A. armeniaca leaves as a function of extraction time and particle size of raw material.…”

Polyisoprenoids from leaves of Althaea armeniaca

“…Polyprenols were identified chemically by comparing physical chemical properties (IR and PMR spectra) with those in the literature [4,5] and TLC mobilities (AL SIL G/UV plates, Germany) using benzene:ethylacetate (24:1, R f 0.53) with those of standard samples of polyprenols isolated from cotton line L-4 leaves. Iodine vapor and vanillin-H 2 SO 4 were used as developers.…”