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Molecules 2018, 23(7), 1734; https://doi.org/10.3390/molecules23071734

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

1
Dipartimento di Scienze Chimiche, Università di Napoli “Federico II”, Complesso Universitario Monte S. Angelo, Via Cintia 4, 80126 Napoli, Italy
2
US Forest Service Rocky Mountain Research Station, Shrub Sciences Laboratory, 735 North 500 East, Provo, UT 84606, USA
3
Dipartimento di Chimica e Chimica Industriale, Università di Pisa, Via Moruzzi 13, 56124 Pisa, Italy
4
Institute of Organic Chemistry, Polish Academy of Sciences, ul. Kasprzaka 44/52, 01-224 Warsaw, Poland
*
Author to whom correspondence should be addressed.
Received: 25 June 2018 / Revised: 10 July 2018 / Accepted: 12 July 2018 / Published: 16 July 2018
(This article belongs to the Special Issue Natural Products Used as Foods and Food Ingredients)
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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 immersion bioassay, both 9-O-methylfusarubin and terpestacin proved to be highly toxic at 10−4 M, causing wilting and plant death within 10 days. This finding suggests that these two compounds could play a role in pathogenesis on B. tectorum. View Full-Text
Keywords: Bromus tectorum; Rutstroemia sp.n.; phytotoxic metabolites; immersion bioassay; 9-O-methylfusarubin and terpestacin Bromus tectorum; Rutstroemia sp.n.; phytotoxic metabolites; immersion bioassay; 9-O-methylfusarubin and terpestacin
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Masi, M.; Meyer, S.; Górecki, M.; Pescitelli, G.; Clement, S.; Cimmino, A.; Evidente, A. Phytotoxic Activity of Metabolites Isolated from Rutstroemia sp.n., the Causal Agent of Bleach Blonde Syndrome on Cheatgrass (Bromus tectorum). Molecules 2018, 23, 1734.

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