Phenolic compounds from Plantago major and P. lanceolata

Abstract

We studied the polyphenol compositions of the plantains Plantago major L. and P. lanceolata L. in order to find new sources of drug raw material. For this, the total polyphenols were isolated from the aerial parts of the plants (yields of 4.6% and 5.4, respectively, of the air-dried raw material mass). Paper chromatography using system 1 (n-BuOH:AcOH:H 2 O, 40:12:28) found that polyphenols from P. major contained 11 compounds. Column chromatography over hide powder using Et 2 O (1), H 2 O (2), and aqueous acetone (60%) (3) separated the total polyphenols into three fractions [1].The first fraction contained a single compound (compound 1), R f 0.51 (system 2, n-BuOH:AcOH:H 2 O, 4:1:5, upper phase). The second fraction had five compounds with R f 0.45, 0.58, 0.53, 0.35, and 0.64 (system 3, n-BuOH:AcOH:H 2 O, 4:1:2). Rechromatography of it over a column of polyamide with elution by aqueous EtOH of various concentrations separated the pure compounds (compounds 2-6). The third fraction was rechromatographed over a column of silica gel with elution by a gradient of Et 2 O:EtOAc with increasing EtOAc content to isolate five pure compounds with R f 0.68, 0.36, 0.31, 0.22, and 0.14 (system 1) that were tannins (compounds 7-11).Compounds 1-9 were identified from the physicochemical properties as gallic acid (1), quercetin-3-rutinoside (rutin) (2), 5,7,3c,4c-tetrahydroxyflavone (luteolin) (3), 3,5,7,4c-tetrahydroxy-3c-methoxyflavone (isorhamnetin) (4), quercetin-3-O-E-D-galactopyranoside (hyperoside) (5), 3,5,7,3c,4c-pentahydroxyflavone (quercetin) (6) [2, 3], 1,2,3,4,6-penta-O-galloyl-E-D-glucose (7), 1,2,3-tri-O-galloyl-E-D-glucose (8), and 1,3,4,6-tetra-O-galloyl-E-D-glucose (9) [2, 3]. Hexahydroxydiphenoyl-1-(O-2-O-galloyl-E-D-glucopyranoside)-1-(O-E-D-xylopyranoside) Diester (10).C 32 H 32 O 23 , white amorphous powder, R f 0.22 (system 1). The acid hydrolysis products (HCl, 5%) were xylose, glucose, gallic and ellagic acids. UV spectrum (EtOH, O max , nm): 265, 283. IR spectrum (KBr, Q, cm -1 ): 3350-3345 (OH), 1730-1710 (ester), 1620-1510 (Ar), 1020-1010 (sugar). PMR spectrum (200 MHz, acetone-d 6 , G, ppm, J/Hz): 4.24 (1H, d, J = 7.7, xyl-1), 3.03 (1H, m, J = 9.3, xyl-2), 3.11 (1H, m, J = 6.2, xyl-3), 3.26 (1H, m, J = 9.3, xyl-4), 3.63 (1H, m, J = 8.5, xyl-5), 4.01 (1H, t, J = 8, Glu

Determination of theIn VitroandIn VivoAntimicrobial Activity on Salivary Streptococci and Lactobacilli and Chemical Characterisation of the Phenolic Content of aPlantago lanceolataInfusion

“…Quercetin-3-rutinoside (rutin, 2 ), quercetin-3- O -D-galactopyranoside (hyperoside, 3 ), 3,5,7,4-tetrahydroxyflavonol (kaempferol, 4 ), 3,5,7,3,4-pentahydroxyflavone (quercetin, 5 ), and 3,5,3,4-tetrahydroxy-7-methoxyflavonol (rhamnetin, 6 ) were also present, while naringenin ( 17 ) was present only in trace amounts, in agreement with the data that Beara et al (2012) reported for methanol extracts ( Figure 1 ) [ 11 ]. Other phenolic compounds with lower molecular weights were identified as vanillic ( 10 ) and gallic ( 1 ) acids, and three derivatives of the latter: 3- O -galloyl-4,6-hexahydroxydiphenoyl-D-glucose ( 7 ), 2,3-di- O -galloyl-D-glucose ( 8 ), and 1,2,3-tri- O -galloyl-D-glucose ( 9 ), which was the most abundant [ 23 ]. Furthermore, a significant amount of cinnamic acids including cinnamic ( 11 ), caffeic ( 12 ) [ 11 ], and chlorogenic ( 13 ) acids was measured ( Figure 2 ).…”

Prebiotic Activity of Poly- and Oligosaccharides Obtained from Plantago major L. Leaves

“…The chemical composition (carbohydrates, proteins, phenolic compounds, chlorophyll) and extraction yield of PWPs were shown in Table 1. P. major L. leaves are generally considered as a rich source of polyphenols and chlorophyll [21,22,[38][39][40]. The initial purification of leaf mass using a series of different solvents (ethanol, chloroform/methanol and acetone) allowed producing a colorless polysaccharide with chlorophyll and polyphenol content less than 0.5%.…”

Effect of Polyphenols Isolated from Plantago major L. and Plantago lanceolata L. on Mitochondrial Permeability Transition Pore in Rat Liver

“…The data of the studied polyphenols on isolation and identification from plants Plantago major L and Plantago lanceolata L are presented in the literature by [10]. These polyphenols are 90 -95 % pure, and they were kindly represented by Makhmudov et al from the Institute of Bioorganic Chemistry of the Academy of Sciences of the Republic of Uzbekistan.…”