Tannins and related compounds. Part 5. Isolation and characterization of polygalloylglucoses from Chinese gallotannin

Two New Acylated Flavanone Glycosides from the Leaves and Branches of Phyllanthus emblica.

“…The Et 2 O layer was partitioned between hexane and MeOH, and the MeOH layer was further chromatographed successively over Sephadex LH-20, silica gel, MCI-gel CHP 20P and Chromatorex ODS to afford 1 and 2, as well as 17 known compounds. The known ones were identified as naringenin, 6) eriodictyol, 6) kaempferol, 7) dihydrokaempferol, 8,9) quercetin, 7) naringenin 7-O-glucoside (prunin), 10) naringenin 7-O-(6Љ-O-galloyl)-glucoside, 10) naringenin 7-O-(6Љ-O-trans-p-coumaroyl)-glucoside, 11) kaempferol 3-O-rhamnoside, 7) quercetin 3-O-rhamnoside, 7) myricetin 3-O-rhamnoside, 7) 2-(2-methylbutyryl)-phloroglucinol 1-O-b-D-glucopyranoside (multifidol glucoside) (5), 12) (Ϫ)-epigallocatechin 3-O-gallate, 13) 1,2,3,6-tetra-O-, 14) 1,2,4,6-tetra-O-, 15) and 1,2,3,4,5-penta-O-galloyl-b-Dglucose, 16) and decarboxyellagic acid 17) by comparison of the physical and spectral data with literature values.…”

Antiproliferative Constituents in the Plant 8. Seeds of Rhynchosia volubilis.

“…Since the latter three fractions showed antiproliferative activity, they were further purified by the same resin chromatography using different solvent systems. 1,6-di-O-galloylglucose, 6) 1-O-galloylglucose, 8) and trigalloylgallic acid, 9) respectively, by comparison of their physical data with those reported.…”

ent-Eudesmane sesquiterpenoids, galloyl esters of the oak lactone precursor, and a 3-O-methylellagic acid glycoside from the wood of Platycarya strobilacea

“…6) (Nishizawa et al, 1982). Production of 15 was deduced to be via acyl migration of galloyl groups or dehydrative dimerization of gallic acid.…”

“…Three new terpenoids, 8,11-dihydroxy-2,4-cycloeudesmane (1), 11-hydroxy-2,4-cycloeudesman-8-one (2) and 2,4-cyclo-7(11)-eudesmen-8-one (3), were isolated along with 3-hydroxy-α-calacorene (4) from the n-hexane extract. The EtOAc fraction primarily contained phenolic compounds, and the 6'-O-galloyl oak lactone precursor (5) (Tanaka et al, 1996), gallic acid, ellagic acid, 1,2,3,4,6-penta-O-galloyl-β-D-glucose (6) (Nishizawa et al, 1982), eugeniin (7) (Nonaka et al, 1980), pedunculagin (8) (Schmidt et al, 1965), 1(β)-galloylpedunculagin (9) (Gupta et al, 1980), casuariin (10) and casuarinin (11) (Okuda et al, 1983) were isolated by a combination of column chromatography steps using Sephadex LH-20, MCI-gel CHP20P, Diaion HP20P and Chromatorex ODS materials, respectively (Fig. 1).…”