Interconverting flavanone glucosides and other phenolic compounds in Lippia salviaefolia Cham. ethanol extracts

Abstract

Four interconverting flavanone glycosides [(2R)- and (2S)-3',4',5,6-tetrahydroxyflavanone 7-O-beta-D-glucopyranoside, and (2R)- and (2S)-3',4',5,8-tetrahydroxyflavanone 7-O-beta-D-glucopyranoside], in addition to eight known flavonoids [naringenin, asebogenin, sakuranetin, 6-hydroxyluteolin 7-O-beta-D-glucoside, (2R)- and (25)-eriodictyol 7-O-beta-D-glucopyranoside, aromadendrin and phloretin], three phenylpropanoid glycosides [forsythoside B. alyssonoside and verbascoside] and the epoxylignan lariciresinol 4'-O-beta-D-glucopyranoside were isolated and identified in the EtOH extract of the aerial parts of Lippia salviaefolia Cham. The phytochemical study herein was guided by preliminary antioxidant tests, namely, beta-carotene protection and 2,2-diphenyl-1-picrylhydrazyl (DPPH) free radical scavenging activity. The crude extracts, their active fractions and the isolated compounds were assayed against intracellular reactive oxygen species (ROS) and human embryonic kidney HEK-293 and human melanoma M14 cancer cell growth. Aromadendrin and phloretin were able to counteract elevation of ROS induced by the oxidant t-butylhydroperoxide (t-BOOH) in HEK-293 cells, whereas phloretin strongly protected HEK-293 cells from ROS damage at 1 mu M. Additionally, phloretin exhibited a significant growth inhibitory effect at 20-40 mu M in both HEK-293 and M14 cells and induced a concentration dependent apoptosis at 20 mu M in M14 cells, suggesting a selective action towards malignant cells. Due to their equilibria, the four interconverting flavanone glycosides were studied using 10 and 2D NMR, HPLC-CD-PDA and HRMS analyses. (C) 2011 Elsevier Ltd. All rights reserved.