Biotransformation of the fungal toxin fomannoxin by conifer cell cultures

Manuela Zweimüller, S. Antus, Tibor Kovács, Johann Sonnenbichler

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

Fomannoxin [(±)-5-Formyl-2-isopropenyl-2,3-dihydrobenzofurane] is a phytotoxic secondary metabolite, which is produced by the forest pathogenic basidiomycete Heterobasidion annosum during the infection process. Fomannoxin shows growth-inhibiting effects on callus and suspension cultures of conifer cells. By investigating the interaction of the phytotoxin with Pinus sylvestris cells a detoxification of fomannoxin was detected, presumably as a defense reaction of the plant cells. Undifferentiated green cell lines of Pinus sylvestris were used as target cells. To provide rac-fomannoxin as a substrate a simple method for the chemical synthesis was developed. It was found that the aromatic aldehyde group is reduced by the plant cells producing the non-toxic fomannoxin alcohol which was isolated and identified by spectroscopy. After longer incubation times, also fomannoxin acid-β-glucoside could be isolated as another detoxification metabolite. For comparison this glucoside was also synthesized.

Original languageEnglish
Pages (from-to)915-921
Number of pages7
JournalBiological Chemistry
Volume378
Issue number8
Publication statusPublished - Aug 1997

Fingerprint

Coniferophyta
Mycotoxins
Biotransformation
Cell culture
Cell Culture Techniques
Pinus sylvestris
Detoxification
Glucosides
Plant Cells
Metabolites
Basidiomycota
Bony Callus
Aldehydes
fomannoxin
Spectrum Analysis
Suspensions
Cells
Alcohols
Spectroscopy
Cell Line

Keywords

  • Conifer cell cultures
  • Detoxification
  • Fomannoxin acid glucoside
  • Fomannoxin alcohol
  • Heterobasidion annosum
  • Pinus sylvestris

ASJC Scopus subject areas

  • Biochemistry

Cite this

Zweimüller, M., Antus, S., Kovács, T., & Sonnenbichler, J. (1997). Biotransformation of the fungal toxin fomannoxin by conifer cell cultures. Biological Chemistry, 378(8), 915-921.

Biotransformation of the fungal toxin fomannoxin by conifer cell cultures. / Zweimüller, Manuela; Antus, S.; Kovács, Tibor; Sonnenbichler, Johann.

In: Biological Chemistry, Vol. 378, No. 8, 08.1997, p. 915-921.

Research output: Contribution to journalArticle

Zweimüller, M, Antus, S, Kovács, T & Sonnenbichler, J 1997, 'Biotransformation of the fungal toxin fomannoxin by conifer cell cultures', Biological Chemistry, vol. 378, no. 8, pp. 915-921.
Zweimüller M, Antus S, Kovács T, Sonnenbichler J. Biotransformation of the fungal toxin fomannoxin by conifer cell cultures. Biological Chemistry. 1997 Aug;378(8):915-921.
Zweimüller, Manuela ; Antus, S. ; Kovács, Tibor ; Sonnenbichler, Johann. / Biotransformation of the fungal toxin fomannoxin by conifer cell cultures. In: Biological Chemistry. 1997 ; Vol. 378, No. 8. pp. 915-921.
@article{363ca4475eb8432f92535b2ddc17cd63,
title = "Biotransformation of the fungal toxin fomannoxin by conifer cell cultures",
abstract = "Fomannoxin [(±)-5-Formyl-2-isopropenyl-2,3-dihydrobenzofurane] is a phytotoxic secondary metabolite, which is produced by the forest pathogenic basidiomycete Heterobasidion annosum during the infection process. Fomannoxin shows growth-inhibiting effects on callus and suspension cultures of conifer cells. By investigating the interaction of the phytotoxin with Pinus sylvestris cells a detoxification of fomannoxin was detected, presumably as a defense reaction of the plant cells. Undifferentiated green cell lines of Pinus sylvestris were used as target cells. To provide rac-fomannoxin as a substrate a simple method for the chemical synthesis was developed. It was found that the aromatic aldehyde group is reduced by the plant cells producing the non-toxic fomannoxin alcohol which was isolated and identified by spectroscopy. After longer incubation times, also fomannoxin acid-β-glucoside could be isolated as another detoxification metabolite. For comparison this glucoside was also synthesized.",
keywords = "Conifer cell cultures, Detoxification, Fomannoxin acid glucoside, Fomannoxin alcohol, Heterobasidion annosum, Pinus sylvestris",
author = "Manuela Zweim{\"u}ller and S. Antus and Tibor Kov{\'a}cs and Johann Sonnenbichler",
year = "1997",
month = "8",
language = "English",
volume = "378",
pages = "915--921",
journal = "Biological Chemistry",
issn = "1431-6730",
publisher = "Walter de Gruyter GmbH & Co. KG",
number = "8",

}

TY - JOUR

T1 - Biotransformation of the fungal toxin fomannoxin by conifer cell cultures

AU - Zweimüller, Manuela

AU - Antus, S.

AU - Kovács, Tibor

AU - Sonnenbichler, Johann

PY - 1997/8

Y1 - 1997/8

N2 - Fomannoxin [(±)-5-Formyl-2-isopropenyl-2,3-dihydrobenzofurane] is a phytotoxic secondary metabolite, which is produced by the forest pathogenic basidiomycete Heterobasidion annosum during the infection process. Fomannoxin shows growth-inhibiting effects on callus and suspension cultures of conifer cells. By investigating the interaction of the phytotoxin with Pinus sylvestris cells a detoxification of fomannoxin was detected, presumably as a defense reaction of the plant cells. Undifferentiated green cell lines of Pinus sylvestris were used as target cells. To provide rac-fomannoxin as a substrate a simple method for the chemical synthesis was developed. It was found that the aromatic aldehyde group is reduced by the plant cells producing the non-toxic fomannoxin alcohol which was isolated and identified by spectroscopy. After longer incubation times, also fomannoxin acid-β-glucoside could be isolated as another detoxification metabolite. For comparison this glucoside was also synthesized.

AB - Fomannoxin [(±)-5-Formyl-2-isopropenyl-2,3-dihydrobenzofurane] is a phytotoxic secondary metabolite, which is produced by the forest pathogenic basidiomycete Heterobasidion annosum during the infection process. Fomannoxin shows growth-inhibiting effects on callus and suspension cultures of conifer cells. By investigating the interaction of the phytotoxin with Pinus sylvestris cells a detoxification of fomannoxin was detected, presumably as a defense reaction of the plant cells. Undifferentiated green cell lines of Pinus sylvestris were used as target cells. To provide rac-fomannoxin as a substrate a simple method for the chemical synthesis was developed. It was found that the aromatic aldehyde group is reduced by the plant cells producing the non-toxic fomannoxin alcohol which was isolated and identified by spectroscopy. After longer incubation times, also fomannoxin acid-β-glucoside could be isolated as another detoxification metabolite. For comparison this glucoside was also synthesized.

KW - Conifer cell cultures

KW - Detoxification

KW - Fomannoxin acid glucoside

KW - Fomannoxin alcohol

KW - Heterobasidion annosum

KW - Pinus sylvestris

UR - http://www.scopus.com/inward/record.url?scp=1842376281&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=1842376281&partnerID=8YFLogxK

M3 - Article

C2 - 9377489

AN - SCOPUS:1842376281

VL - 378

SP - 915

EP - 921

JO - Biological Chemistry

JF - Biological Chemistry

SN - 1431-6730

IS - 8

ER -