Phytotoxic Activity of Metabolites Isolated from Rutstroemia sp.n , the Causal Agent of Bleach Blonde Syndrome on Cheatgrass (Bromus tectorum )

Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry
Marco MasiAntonio Evidente

Abstract

A fungal pathogen soon to be described as Rutstroemia capillus-albis (Rutstroemiaceae, Helotiales, Leotiomycetes) has been identified as the causal agent of 'bleach blonde syndrome' on the invasive annual grass weed Bromus tectorum (cheatgrass) in western North America. This apparently common but previously undescribed disease causes premature senescence and sterility, but does not affect seed germination or seedling emergence and growth. This study investigated whether the new species produces phytotoxins that could be implicated in pathogenesis. The compounds 9-O-methylfusarubin, 9-O-methylbostrycoidin, 5-O-methylnectriafurone, trans-methyl-p-coumarate and terpestacin were isolated from the solid culture of this fungus. The undescribed absolute stereochemistry at C-3 of 9-O-methylfusarubin and at C-1' of 5-O-methylnectriafurone were assigned by applying electronic and vibrational circular dichroism (ECD and VCD) combined with computational methods and the advanced Mosher's method, respectively. The first three listed compounds are naphtoquinone pigments, while terpestacin is a sesterterpene, and trans-methyl-p-coumarate could be the product of an unusual fungal phenylpropanoid biosynthesis pathway. In a juvenile plant immersi...Continue Reading

References

Jul 1, 1990·Mycopathologia·R A BakerS Nemec
May 7, 2004·Applied and Environmental Microbiology·Stephane GrazianiMarie-Josee Daboussi
Jun 21, 2005·Phytochemistry·Subramanium GopalakrishnanRichard N Strange
Sep 26, 2009·The Journal of Antibiotics·Junko HashimotoKazuo Shin-ya
Apr 12, 2012·Applied and Environmental Microbiology·Lena StudtBettina Tudzynski
Sep 30, 2014·Journal of Agricultural and Food Chemistry·Marco MasiAntonio Evidente
Jul 15, 2015·Natural Product Research·Zerihun T DameTeunis van Ree
Oct 8, 2015·Natural Product Reports·Alessio CimminoAntonio Evidente
Mar 16, 2017·Journal of Pharmaceutical and Biomedical Analysis·Alessio CimminoAntonio Evidente
Mar 25, 2017·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Daniela RossiSimona Collina

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Methods Mentioned

BETA
column chromatography
circular dichroism

Software Mentioned

SpecDis
SAS Proc Mixed
Gaussian
Spartan

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