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
