LC-MS/MS Tandem Mass Spectrometry for Analysis of Phenolic Compounds and Pentacyclic Triterpenes in Antifungal Extracts of Terminalia brownii (Fresen)

Abstract

Decoctions and macerations of the stem bark and wood of Terminalia brownii Fresen. are used in traditional medicine for fungal infections and as fungicides on field crops and in traditional granaries in Sudan. In addition, T. brownii water extracts are commonly used as sprays for protecting wooden houses and furniture. Therefore, using agar disc diffusion and macrodilution methods, eight extracts of various polarities from the stem wood and bark were screened for their growth-inhibitory effects against filamentous fungi commonly causing fruit, vegetable, grain and wood decay, as well as infections in the immunocompromised host. Ethyl acetate extracts of the stem wood and bark gave the best antifungal activities, with MIC values of 250 µg/mL against Nattrassia mangiferae and Fusarium verticillioides, and 500 µg/mL against Aspergillus niger and Aspergillus flavus. Aqueous extracts gave almost as potent effects as the ethyl acetate extracts against the Aspergillus and Fusarium strains, and were slightly more active than the ethyl acetate extracts against Nattrassia mangiferae. Thin layer chromatography, RP-HPLC-DAD and tandem mass spectrometry (LC-MS/MS), were employed to identify the chemical constituents in the ethyl acetate fractions of the stem bark and wood. The stem bark and wood were found to have a similar qualitative composition of polyphenols and triterpenoids, but differed quantitatively from each other. The stilbene derivatives, cis- (3) and trans- resveratrol-3-O-β-galloylglucoside (4), were identified for the first time in T. brownii. Moreover, methyl-(S)-flavogallonate (5), quercetin-7-β-O-di-glucoside (8), quercetin-7-O-galloyl-glucoside (10), naringenin-4′-methoxy-7-pyranoside (7), 5,6-dihydroxy-3′,4′,7-tri-methoxy flavone (12), gallagic acid dilactone (terminalin) (6), a corilagin derivative (9) and two oleanane type triterpenoids (1) and (2) were characterized. The flavonoids, a corilagin derivative and terminalin, have not been identified before in T. brownii. We reported earlier on the occurrence of methyl-S-flavogallonate and its isomer in the roots of T. brownii, but this is the first report on their occurrence in the stem wood as well. Our results justify the traditional uses of macerations and decoctions of T. brownii stem wood and bark for crop and wood protection and demonstrate that standardized extracts could have uses for the eco-friendly control of plant pathogenic fungi in African agroforestry systems. Likewise, our results justify the traditional uses of these preparations for the treatment of skin infections caused by filamentous fungi.

Chitosan Film Containing Mansoa hirsuta Fraction for Wound Healing

“…The neutral losses of H 2 O, HCOOH, and CH 4 are observed from all structures. The loss of H 2 O is characteristic of an OH group, whereas the loss of HCOOH is a characteristic of fragmentation of pentacyclic triterpenes [28,29]. Pentacyclic triterpenes are secondary metabolites widely found in a variety of organisms such as bacteria, fungi, plants, and mammals [30].…”

Phenolic profiling and antibacterial potential of Saudi Arabian native date palm (Phoenix dactylifera) cultivars

“…The analysis was based on the literature with some modifications. [8,9,28] In brief, AB Sciex 3200QTrap Liquid Chromatography-tandem Mass Spectrometer (LCMS/MS) (AB Sciex, Toronto, Canada) coupled to Perkin Elmer Flexar FX15 ultra-high performance liquid chromatography (UHPLC) system (Massachusetts, USA), operated using electrospray (ESI) ionization in negative ion mode, with AB Sciex Analyst software for data acquisition and equipped with a Perkin Elmer ultra-high performance flexar binary pump, with column oven and an autosampler with a 20 µL loop was used. The mobile phases used were A (water with 0.1% formic acid and 5 mM ammonium formate) and B (acetonitrile with 0.1% formic acid and 5 mM ammonium formate) under the following conditions: flow rate interchanging from 800 µL/min to 1 mL/min, temperature at 40ºC, rapid screening at 15 min run time, linear gradients from 10% B to 90% B from 0.01 min to 8 min, hold 90% B for 2 min were applied, followed by a return to the initial conditions (10% B) in 5 min and reequilibration of the column.…”

Plants of the Genus Terminalia: An Insight on Its Biological Potentials, Pre-Clinical and Clinical Studies

“… Some of the common Terminalia sp. Reproduced under the Creative Commons Attribution License ( Afshari et al., 2016 ; Marjenah and Putri, 2017 ; Salih et al., 2017 ). …”