High resolution UHPLC-MS characterization and isolation of main compounds from the antioxidant medicinal plant Parastrephia lucida (Meyen)

Abstract

High-resolution mass spectrometry is currently used to determine the mass of biologically active compounds in medicinal plants and food and UHPLC-Orbitrap is a relatively new technology that allows fast fingerprinting and metabolomics analysis. Forty-two metabolites including several phenolic acids, flavonoids, coumarines, tremetones and ent-clerodane diterpenes were accurately identified for the first time in the resin of the medicinal plant (Asteraceae) a Chilean native species, commonly called umatola, collected in the pre-cordillera and altiplano regions of northern Chile, by means of UHPLC-PDA-HR-MS. This could be possible by the state of the art technology employed, which allowed well resolved total ion current peaks and the proposal of some biosynthetic relationships between the compounds detected. Some mayor compounds were also isolated using HSCCC. The ethanolic extract showed high total polyphenols content and significant antioxidant capacity. Furthermore, several biological assays were performed that determined the high antioxidant capacity found for the mayor compound isolated from the plant, 11--coumaroyloxyltremetone.

Crystal structure of 5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3,7,8-trimethoxy-4H-chromen-4-one, C19H18O8

“…The title compound was isolated using medium pressure column chromatography (MPCC) from Parastrephia quadrangularis, a medicinal plant used by the Aymara Amerindians [6,7], a known producer of several flavonoids and benzoic acid derivatives with antioxidant activity [8][9][10][11]. Following our program to isolate interesting metabolites from the Atacama Desert Flora, Northern Chile [12][13][14][15][16][17][18], dried aerial parts of P. quadrangularis (1622 g) collected in april 2015 in "El Tatio", Andean mountain range of the of Atacama Desert, II Region, Northern Chile, were defatted with hexane (3 liters, 3 times in the dark, 24 hours each time) and 54.82 g were obtained after evaporation of the solvent.…”

“…The title compound was isolated using medium pressure column chromatography (MPCC) from Parastrephia quadrangularis, a medicinal plant used by the Aymara Amerindians [6,7], a known producer of several flavonoids and benzoic acid derivatives with antioxidant activity [8][9][10][11] . These data, together with ESI-MS/MS and correlations observed in the HSQC and HMBC spectra, are consistent with the structure of the title compound (cf.…”

Antifungal activity ofParastrephia quadrangularis(Meyen) Cabrera extracts againstFusarium verticillioides

“…Another peak (5), at 17 min, 285 m / z , was present in DCM fractions and subextracts; this compound was identified as kaempferol, a flavonol also reported in P. lucida (Echiburu‐Chau et al . ).…”

“…Some phytochemical studies conducted in Parastrephia lucida identified 42 metabolites including several phenolic acids, flavonoids, coumarins, tremetones and entclerodane diterpenes (Echiburu‐Chau et al . ). Bohlmann et al .…”

“…; Echiburu‐Chau et al . ), as well as antifungal activity (Salvat ; Sayago et al . ; Palavecino Ruiz et al .…”