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Antibiotics (Basel). 2017 Dec 13;6(4). pii: E37. 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).

Author information

1
Department of Forest Products and Industries, Faculty of Forestry, PO Box 13314, University of Khartoum, Khartoum 11111, Sudan. enass.salih@helsinki.fi.
2
Faculty of Pharmacy, Division of Pharmaceutical Biosciences, PO Box 56, University of Helsinki, FIN-00014 Helsinki, Finland. enass.salih@helsinki.fi.
3
Viikki Tropical Resources Institute (VITRI), Department of Forest Sciences, PO Box 27, University of Helsinki, FIN-00014 Helsinki, Finland. enass.salih@helsinki.fi.
4
Faculty of Pharmacy, Division of Pharmaceutical Biosciences, PO Box 56, University of Helsinki, FIN-00014 Helsinki, Finland. pia.fyhrquist@helsinki.fi.
5
Department of Forest Products and Industries, Faculty of Forestry, PO Box 13314, University of Khartoum, Khartoum 11111, Sudan. amahmed@uofk.edu.
6
Department of Forest Products and Industries, Faculty of Forestry, PO Box 13314, University of Khartoum, Khartoum 11111, Sudan. ayabdelgadir@uofk.edu.
7
Viikki Tropical Resources Institute (VITRI), Department of Forest Sciences, PO Box 27, University of Helsinki, FIN-00014 Helsinki, Finland. markku.kanninen@helsinki.fi.
8
Viikki Tropical Resources Institute (VITRI), Department of Forest Sciences, PO Box 27, University of Helsinki, FIN-00014 Helsinki, Finland. Marketta.Sipi@helsinki.fi.
9
Viikki Tropical Resources Institute (VITRI), Department of Forest Sciences, PO Box 27, University of Helsinki, FIN-00014 Helsinki, Finland. olavi.luukkanen@helsinki.fi.
10
Department of Forest Products and Industries, Faculty of Forestry, PO Box 13314, University of Khartoum, Khartoum 11111, Sudan. mkfahmi@uofk.edu.
11
Viikki Tropical Resources Institute (VITRI), Department of Forest Sciences, PO Box 27, University of Helsinki, FIN-00014 Helsinki, Finland. mkfahmi@uofk.edu.
12
Department of Phytochemistry, Faculty of Pharmacy, PO Box 477, University of Sciences and Technology, Omdurman, Sudan. maielamin15@gmail.com.
13
Commission for Biotechnology and Genetic Engineering, PO Box 2404, National Centre for Research, Khartoum, Sudan. hibaali@hotmail.com.

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 Nattrassiamangiferae. 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.

KEYWORDS:

Africa; Aspergillus; Fusarium; LC-MS/MS; Nattrassia; Terminalia brownii; antifungal stem wood and bark extracts; ellagitannins; flavonoids; stilbenes; triterpenes

Conflict of interest statement

The authors declare no conflict of interest. The founding sponsors had no role in the design of the study; in the collection, analyses, or interpretation of data; in the writing of the manuscript, and in the decision to publish the results.

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