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

Citation

Funari, CS and Passalacqua, TG and Rinaldo, D and Napolitano, A and Festa, M and Capasso, A and Piacente, S and Pizza, C and Young, MCM and Durigan, G and Silva, DHS, Interconverting flavanone glucosides and other phenolic compounds in Lippia salviaefolia Cham. ethanol extracts, Phytochemistry, 72, (16) pp. 2052-2061. ISSN 0031-9422 (2011) [Refereed Article]

Copyright Statement

Copyright 2011 Elsevier Ltd.

DOI: doi:10.1016/j.phytochem.2011.07.004

Abstract

Four interconverting flavanone glycosides [(2R)- and (2S)-3′,4′,5,6-tetrahydroxyflavanone 7-O-β-d-glucopyranoside, and (2R)- and (2S)-3′,4′,5,8-tetrahydroxyflavanone 7-O-β-d-glucopyranoside], in addition to eight known flavonoids [naringenin, asebogenin, sakuranetin, 6-hydroxyluteolin 7-O-β-d-glucoside, (2R)- and (2S)-eriodictyol 7-O-β-d-glucopyranoside, aromadendrin and phloretin], three phenylpropanoid glycosides [forsythoside B, alyssonoside and verbascoside] and the epoxylignan lariciresinol 4′-O-β-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, β-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 μM. Additionally, phloretin exhibited a significant growth inhibitory effect at 20–40 μM in both HEK-293 and M14 cells and induced a concentration dependent apoptosis at 20 μM in M14 cells, suggesting a selective action towards malignant cells. Due to their equilibria, the four interconverting flavanone glycosides were studied using 1D and 2D NMR, HPLC–CD–PDA and HRMS analyses.

Item Details

Item Type:Refereed Article
Keywords:Lippia salviaefolia Cham., verbenaceae, antioxidant, cell growth inhibition, flavonoids, phenylpropanoid glycosides, epoxylignan, reactive oxygen species, cancer cells, circular dichroism
Research Division:Chemical Sciences
Research Group:Analytical Chemistry
Research Field:Separation Science
Objective Division:Expanding Knowledge
Objective Group:Expanding Knowledge
Objective Field:Expanding Knowledge in the Chemical Sciences
Author:Funari, CS (Dr Cristiano Funari)
ID Code:91089
Year Published:2011
Web of Science® Times Cited:17
Deposited By:Austn Centre for Research in Separation Science
Deposited On:2014-05-07
Last Modified:2014-06-06
Downloads:0

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