Abstract
A rational and selective method using on-line high-performance liquid chromatography (HPLC) coupled with electrospray quadrupole time-of-flight tandem mass spectrometry (ESI-QToF-MS/MS) was established for the dereplication of phenolic derivatives from Qualea grandiflora and Qualea cordata. The selection of the extracts was based on the antioxidant capacity measured by in vitro DPPH assay. The HPLC-ESI-QToF-MS/MS analysis was conducted by on-flow detection, using high-resolution mass/ratio ions as well as collision induced MS/MS experiments for selected protonated ions. The dereplication of the EtOAc fraction from the hydro-alcohol extract from the stem bark of Q. grandiflora allowed the detection of the flavonoids: 3',4',5',5,6,7-hexahydroxy-8-methylflavanone, 8-methyl-naringenine and 3',7-dimethoxy-8-methyl-4',5,7-trihydroxyflavanone, as well as a benzophenone derivatives: bis(4,6-dimethoxy-2-hydroxy-3-methylphenyl)-metanone, 3',4'-dimethoxy-8-methyl-5,6,7-trihydroxyflavanone, 7-methoxy-6-methyl-3',4',5-trihydroxyflavanone, 6,8-dimethyl-3'-methoxy-4',5,7-trihydroxyflavanone and 3',5'-dimethoxy-6,8-dimethyl-4',5,7-trihydroxyflavanone were detected in the EtOAc fraction from the hydro-alcohol extract from the leaves of Q. cordata.
Highlights
Vochysiaceae is composed of two tribes, eight genera and approximately 200 species of trees and shrubs, distributed in the tropical regions of Central and South America and Western Africa.[1,2,3,4]Many Vochysiaceae species, in special those belonging to Qualea and Vochysia, are used in traditional medicine to treat diarrhea, intestinal pain, gastric ulcer, inflammations and wounds.[5,6,7,8]Previous phytochemical analysis of some species of this family led to the identification of lupane, oleanane and ursane triterpenes, steroids, flavonoids as well as ellagic acid derivatives (EAD).[9]Vol 24, No 5, 2013Pharmacological studies focused on the gastroprotective and anti-inflammatory actions of some Qualea species indicated a relationship between the pharmacological effects and the presence of EAD and polyphenolic compounds.[10]Since the therapeutic effects reported for Qualea are a result of their use as complex herbal preparations, avant garde analytical techniques are necessary to identify and detect the bioactive constituents of the crude mixture without performing any time consuming isolation
Pharmacological studies focused on the gastroprotective and anti-inflammatory actions of some Qualea species indicated a relationship between the pharmacological effects and the presence of ellagic acid derivatives (EAD) and polyphenolic compounds.[10]
In order to evaluate the radical scavenging activity of the metabolites dereplicated by high-performance liquid chromatography (HPLC)-ESI-QToF-MS/MS, the EtOAc fraction from the stem bark of Q. grandiflora and the EtOAc fraction from the leaves of Q. cordata were analyzed on a Shimadzu LC-20A HPLC apparatus controlled by the software CLASS-VP 6.14 coupled with a Gilson F203 fraction collector (Gilson, Middleton, WI, USA)
Summary
Vochysiaceae is composed of two tribes, eight genera and approximately 200 species of trees and shrubs, distributed in the tropical regions of Central and South America and Western Africa.[1,2,3,4]Many Vochysiaceae species, in special those belonging to Qualea and Vochysia, are used in traditional medicine to treat diarrhea, intestinal pain, gastric ulcer, inflammations and wounds.[5,6,7,8]Previous phytochemical analysis of some species of this family led to the identification of lupane, oleanane and ursane triterpenes, steroids, flavonoids as well as ellagic acid derivatives (EAD).[9]Vol 24, No 5, 2013Pharmacological studies focused on the gastroprotective and anti-inflammatory actions of some Qualea species indicated a relationship between the pharmacological effects and the presence of EAD and polyphenolic compounds.[10]Since the therapeutic effects reported for Qualea are a result of their use as complex herbal preparations, avant garde analytical techniques are necessary to identify and detect the bioactive constituents of the crude mixture without performing any time consuming isolation. Qualea grandiflora and Qualea cordata, two Brazilian Vochysiaceae species, were analyzed by means of HPLC-ESI-QToF-MS/MS guided by the in vitro DPPH (2,2-diphenyl-1-picrylhydrazyl) scavenging capacity aiming at the detection of bioactive polyphenolic molecules.
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