Isolation and structural elucidation of a novel brunnein-type antioxidant β-carboline alkaloid from Cyclocybe cylindracea

Dániel Krüzselyi, J. Vetter, P. Ott, András Darcsi, S. Béni, A. Gömöry, L. Drahos, F. Zsila, A. Móricz

Research output: Contribution to journalArticle

Abstract

Effect-directed isolation of free radical scavengers from the methanol extract of the freeze-dried fruiting bodies of the cultivated basidiomycetous mushroom, black poplar (Cyclocybe cylindracea), yielded a β-carboline alkaloid. Its structure was determined based on ESI-TOF-MS/MS, NMR and circular dichroism spectra by comparison with published data. The compound, identified as the C1-S diastereomer of brunnein B, exhibited explicit radical scavenging activity (EC50 = 119.1 ± 1.2 μg/mL). The quantity of the active component was determined with HPLC-MS in the fruiting body (36.2 ± 2.8 ng/g DW, dry weight) and its different tissues such as peel (94.7 ± 1.9 ng/g DW), inner cap (90.5 ± 1.3 ng/g DW), gills (71.5 ± 0.6 ng/g DW), and stipe (162.2 ± 1.7 ng/g DW). It is a β-carboline alkaloid that was not reported previously.

Original languageEnglish
Article number104180
JournalFitoterapia
Volume137
DOIs
Publication statusPublished - Sep 1 2019

Fingerprint

Carbolines
Alkaloids
Antioxidants
Populus
Free Radical Scavengers
Agaricales
Circular Dichroism
Methanol
High Pressure Liquid Chromatography
Weights and Measures
brunnein B

Keywords

  • Antioxidant
  • Black poplar (Cyclocybe cylindracea)
  • C1-S diastereomer of brunnein B
  • Effect-directed isolation
  • Mushroom

ASJC Scopus subject areas

  • Pharmacology
  • Drug Discovery

Cite this

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title = "Isolation and structural elucidation of a novel brunnein-type antioxidant β-carboline alkaloid from Cyclocybe cylindracea",
abstract = "Effect-directed isolation of free radical scavengers from the methanol extract of the freeze-dried fruiting bodies of the cultivated basidiomycetous mushroom, black poplar (Cyclocybe cylindracea), yielded a β-carboline alkaloid. Its structure was determined based on ESI-TOF-MS/MS, NMR and circular dichroism spectra by comparison with published data. The compound, identified as the C1-S diastereomer of brunnein B, exhibited explicit radical scavenging activity (EC50 = 119.1 ± 1.2 μg/mL). The quantity of the active component was determined with HPLC-MS in the fruiting body (36.2 ± 2.8 ng/g DW, dry weight) and its different tissues such as peel (94.7 ± 1.9 ng/g DW), inner cap (90.5 ± 1.3 ng/g DW), gills (71.5 ± 0.6 ng/g DW), and stipe (162.2 ± 1.7 ng/g DW). It is a β-carboline alkaloid that was not reported previously.",
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AU - Krüzselyi, Dániel

AU - Vetter, J.

AU - Ott, P.

AU - Darcsi, András

AU - Béni, S.

AU - Gömöry, A.

AU - Drahos, L.

AU - Zsila, F.

AU - Móricz, A.

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