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Structure and biosynthesis of fungal secondary metabolites

studies of the root rot pathogen Heterobasidion annosum s.l. and the biocontrol fungus Phlebiopsis gigantea

Hansson, David (2013). Structure and biosynthesis of fungal secondary metabolites. Diss. (sammanfattning/summary) Uppsala : Sveriges lantbruksuniv., Acta Universitatis Agriculturae Sueciae, 1652-6880 ; 2013:63
ISBN 978-91-576-7864-5
eISBN 978-91-576-7865-2
[Doctoral thesis]

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The root rot pathogen Heterobasidion annosum s.l., i.e. H. abietinum, H. parviporum, H. annosum s.s., H. irregulare and H. occidentale, and the biocontrol fungus Phlebiopsis gigantea were investigated regarding their secondary metabolites.

Thirty-three compounds, in total, were identified from H. annosum s.l. by HRMS and NMR, including six new fomannosin related sesquiterpenes (illudolone A and B, illudolactone A and B and deoxyfomannosin A and B), one new fomajorin-type compound and seven previously unreported natural products with fomannoxin related structures. The new fomannosin related compounds were proposed to be intermediates in the biosynthesis of the known phytoxin fomannosin.

Fomannoxin is a benzohydrofuran that previously has been suggested to be involved in the pathogenicity of H. annosum s.l. The biosynthesis of fomannoxin was investigated through an isotopic enrichment study utilizing [1-13C]glucose as metabolic tracer. The results showed that fomannoxin is produced by a combination of the MVA pathway and the shikimic acid pathway.

The secondary metabolite production of the species within H. annosum s.l. was analyzed by LC-HRMS. Subsequent principal component analysis showed that the samples from the five species grouped in accord with the respective species, preferred host and previously established phylogeny.

The biocontrol fungus P. gigantea is used to prevent root rot caused by H. annosum s.l. Its mode of action was studied by investigating the production of secondary metabolites. Five secondary metabolites were isolated and identified by HRMS and NMR, out of which three were new compounds (phlebiopsin A-C), one was a new natural product (methyl-terfestatin A) and one was a known compound (o-orsellinaldehyde). Only o-orsellinaldehyde showed growth inhibiting activity against H. occidentale.

Authors/Creators:Hansson, David
Title:Structure and biosynthesis of fungal secondary metabolites
Subtitle:studies of the root rot pathogen Heterobasidion annosum s.l. and the biocontrol fungus Phlebiopsis gigantea
Series Name/Journal:Acta Universitatis Agriculturae Sueciae
Year of publishing :2013
Number of Pages:73
I.Hansson, D., Menkis, A., Himmelstrand, K., Thelander, M., Olson, Å., Stenlid, J. and Broberg, A. (2012). Sesquiterpenes from the conifer root rot pathogen Heterobasidion occidentale. Phytochemistry 82, 158-165.
II.Hansson, D., Menkis, A., Olson, Å., Stenlid, J., Broberg, A. and Karlsson, M. (2012). Biosynthesis of fomannoxin in the root rotting pathogen Heterobasidion occidentale. Phytochemistry 84, 31-39.
III.Hansson, D., Wubshet, S. G., Olson, Å., Karlsson, M., Staerk, D. and Broberg, A. Secondary metabolite comparison of the species within the Heterobasidion annosum s.l. complex (manuscript).
IV.Hansson, D., Menkis, A. and Broberg, A. Secondary metabolites from the root rot biocontrol fungus Phlebiopsis gigantea (submitted to Phytochemistry).
Place of Publication:Uppsala
Publisher:Institutionen för kemi, Sveriges lantbruksuniversitet
ISBN for printed version:978-91-576-7864-5
ISBN for electronic version:978-91-576-7865-2
Publication Type:Doctoral thesis
Full Text Status:Public
Agris subject categories.:F Plant production > F60 Plant physiology and biochemistry
H Protection of plants and stored products > H01 Protection of plants - General aspects
H Protection of plants and stored products > H20 Plant diseases
X Agricola extesions > X50 Chemistry
Subjects:(A) Swedish standard research categories 2011 > 1 Natural sciences > 104 Chemical Sciences > Analytical Chemistry
(A) Swedish standard research categories 2011 > 1 Natural sciences > 104 Chemical Sciences > Organic Chemistry
Agrovoc terms:heterobasidion annosum, phlebia, secondary metabolites, biosynthesis, root rots, biological control, mass spectrometry, nmr spectroscopy, hplc
Keywords:Heterobasidion annosum s.l., Phlebiopsis gigantea, secondary metabolites, biosynthesis, root rot, biocontrol, MS, NMR, HPLC
Permanent URL:
ID Code:10819
Department:(NL, NJ) > Dept. of Chemistry (until 131231)
Deposited By: David Hansson
Deposited On:25 Sep 2013 13:51
Metadata Last Modified:14 Dec 2014 08:16

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