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

Tutkimustuotos: ArtikkelijulkaisuArtikkeliTieteellinenvertaisarvioitu

Kuvaus

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 ug/mL against Nattrassia mangiferae and Fusarium verticillioides, and 500 ug/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-b-galloylglucoside (4), were identified for the first time in T. brownii. Moreover,
methyl-(S)-flavogallonate (5), quercetin-7-b-O-di-glucoside (8), quercetin-7-O-galloyl-glucoside (10), naringenin-40-methoxy-7-pyranoside (7), 5,6-dihydroxy-30,40,7-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.
Alkuperäiskielienglanti
Artikkeli37
LehtiAntibiotics
Vuosikerta6
Sivumäärä18
ISSN2079-6382
DOI - pysyväislinkit
TilaJulkaistu - joulukuuta 2017
OKM-julkaisutyyppiA1 Alkuperäisartikkeli tieteellisessä aikakauslehdessä, vertaisarvioitu

Tieteenalat

  • 317 Farmasia

Lainaa tätä

@article{942155cf675a41c795165e23f2111a21,
title = "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 causingfruit, 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 ug/mL against Nattrassia mangiferae and Fusarium verticillioides, and 500 ug/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 andtriterpenoids, but differed quantitatively from each other. The stilbene derivatives, cis- (3) and trans- resveratrol-3-O-b-galloylglucoside (4), were identified for the first time in T. brownii. Moreover,methyl-(S)-flavogallonate (5), quercetin-7-b-O-di-glucoside (8), quercetin-7-O-galloyl-glucoside (10), naringenin-40-methoxy-7-pyranoside (7), 5,6-dihydroxy-30,40,7-tri-methoxy flavone (12), gallagic aciddilactone (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 causedby filamentous fungi.",
keywords = "317 Pharmacy, Africa , Terminalia brownii , antifungal stem wood and bark extracts , Aspergillus , Nattrassia , Fusarium, LC-MC/MS, flavonoids, ellagitannins, stilbenes, triterpenes",
author = "Salih, {Enass Yousif Abdelkarium} and Fyhrqvist, {Pia Johanna} and Abdalla, {Ashraf M. A.} and Abdelgadir, {Abdelazim Y.} and Kanninen, {Markku Tapani} and Sipi, {Marketta Hannele} and Luukkanen, {Martti Olavi} and Mustafa Fahmi and Elamin, {Mai H.} and Ali, {Hiba A.}",
year = "2017",
month = "12",
doi = "10.3390/antibiotics6040037",
language = "English",
volume = "6",
journal = "Antibiotics",
issn = "2079-6382",
publisher = "MDPI",

}

LC-MS/MS Tandem Mass Spectrometry for Analysis of Phenolic Compounds and Pentacyclic Triterpenes in Antifungal Extracts of Terminalia brownii (Fresen). / Salih, Enass Yousif Abdelkarium; Fyhrqvist, Pia Johanna; Abdalla, Ashraf M. A.; Abdelgadir, Abdelazim Y.; Kanninen, Markku Tapani; Sipi, Marketta Hannele; Luukkanen, Martti Olavi; Fahmi, Mustafa; Elamin, Mai H.; Ali, Hiba A.

julkaisussa: Antibiotics, Vuosikerta 6 , 37, 12.2017.

Tutkimustuotos: ArtikkelijulkaisuArtikkeliTieteellinenvertaisarvioitu

TY - JOUR

T1 - LC-MS/MS Tandem Mass Spectrometry for Analysis of Phenolic Compounds and Pentacyclic Triterpenes in Antifungal Extracts of Terminalia brownii (Fresen)

AU - Salih, Enass Yousif Abdelkarium

AU - Fyhrqvist, Pia Johanna

AU - Abdalla, Ashraf M. A.

AU - Abdelgadir, Abdelazim Y.

AU - Kanninen, Markku Tapani

AU - Sipi, Marketta Hannele

AU - Luukkanen, Martti Olavi

AU - Fahmi, Mustafa

AU - Elamin, Mai H.

AU - Ali, Hiba A.

PY - 2017/12

Y1 - 2017/12

N2 - 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 causingfruit, 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 ug/mL against Nattrassia mangiferae and Fusarium verticillioides, and 500 ug/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 andtriterpenoids, but differed quantitatively from each other. The stilbene derivatives, cis- (3) and trans- resveratrol-3-O-b-galloylglucoside (4), were identified for the first time in T. brownii. Moreover,methyl-(S)-flavogallonate (5), quercetin-7-b-O-di-glucoside (8), quercetin-7-O-galloyl-glucoside (10), naringenin-40-methoxy-7-pyranoside (7), 5,6-dihydroxy-30,40,7-tri-methoxy flavone (12), gallagic aciddilactone (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 causedby filamentous fungi.

AB - 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 causingfruit, 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 ug/mL against Nattrassia mangiferae and Fusarium verticillioides, and 500 ug/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 andtriterpenoids, but differed quantitatively from each other. The stilbene derivatives, cis- (3) and trans- resveratrol-3-O-b-galloylglucoside (4), were identified for the first time in T. brownii. Moreover,methyl-(S)-flavogallonate (5), quercetin-7-b-O-di-glucoside (8), quercetin-7-O-galloyl-glucoside (10), naringenin-40-methoxy-7-pyranoside (7), 5,6-dihydroxy-30,40,7-tri-methoxy flavone (12), gallagic aciddilactone (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 causedby filamentous fungi.

KW - 317 Pharmacy

KW - Africa

KW - Terminalia brownii

KW - antifungal stem wood and bark extracts

KW - Aspergillus

KW - Nattrassia

KW - Fusarium

KW - LC-MC/MS

KW - flavonoids

KW - ellagitannins

KW - stilbenes

KW - triterpenes

U2 - 10.3390/antibiotics6040037

DO - 10.3390/antibiotics6040037

M3 - Article

VL - 6

JO - Antibiotics

JF - Antibiotics

SN - 2079-6382

M1 - 37

ER -