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Antibiotics 2017, 6(4), 37; doi:10.3390/antibiotics6040037

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

1
Department of Forest Products and Industries, Faculty of Forestry, PO Box 13314, University of Khartoum, Khartoum 11111, Sudan
2
Commission for Biotechnology and Genetic Engineering, PO Box 2404, National Centre for Research, Khartoum, Sudan
3
Faculty of Pharmacy, Division of Pharmaceutical Biosciences, PO Box 56, University of Helsinki, FIN-00014 Helsinki, Finland
4
Viikki Tropical Resources Institute (VITRI), Department of Forest Sciences, PO Box 27, University of Helsinki, FIN-00014 Helsinki, Finland
5
Department of Phytochemistry, Faculty of Pharmacy, PO Box 477, University of Sciences and Technology, Omdurman, Sudan
With this paper we would like to honor our colleague, Dr. Hiba Ali, who passed away the 29.4.2016.
*
Author to whom correspondence should be addressed.
Academic Editor: Leonard Amaral
Received: 30 October 2017 / Revised: 29 November 2017 / Accepted: 7 December 2017 / Published: 13 December 2017
(This article belongs to the Special Issue Top 35 of Antibiotics Travel Awards 2017)
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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. View Full-Text
Keywords: Africa; Terminalia brownii; antifungal stem wood and bark extracts; Aspergillus; Nattrassia; Fusarium; LC-MS/MS; flavonoids; ellagitannins; stilbenes; triterpenes Africa; Terminalia brownii; antifungal stem wood and bark extracts; Aspergillus; Nattrassia; Fusarium; LC-MS/MS; flavonoids; ellagitannins; stilbenes; triterpenes
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Salih, E.Y.A.; Fyhrquist, P.; Abdalla, A.M.A.; Abdelgadir, A.Y.; Kanninen, M.; Sipi, M.; Luukkanen, O.; Fahmi, M.K.M.; Elamin, M.H.; Ali, H.A. LC-MS/MS Tandem Mass Spectrometry for Analysis of Phenolic Compounds and Pentacyclic Triterpenes in Antifungal Extracts of Terminalia brownii (Fresen). Antibiotics 2017, 6, 37.

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