Radicinin from Cochliobolus sp. inhibits Xylella fastidiosa, the causal agent of Pierce’s Disease of grapevine

Radicinin (1) produced by a strain of Cochliobolus sp. isolated from grapevine inhibits Xylella fastidiosa in vitro, suggesting a possible mechanism for tolerance of Pierce’s Disease. [Display omitted] •Endophytes may confer grapevine with non-genetic tolerance of Pierce’s Disease.•A Cochliobolus sp...

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Published in:	Phytochemistry (Oxford) Vol. 116; pp. 130 - 137
Main Authors:	Aldrich, Thomas J., Rolshausen, Philippe E., Roper, M. Caroline, Reader, Jordan M., Steinhaus, Matthew J., Rapicavoli, Jeannette, Vosburg, David A., Maloney, Katherine N.
Format:	Journal Article
Language:	English
Published:	England Elsevier Ltd 01-08-2015
Subjects:	Antibiotic Ascomycota - chemistry Cochliobolus sp Endophytic fungus Grapevine Molecular Structure Nuclear Magnetic Resonance, Biomolecular Pierce’s Disease Plant Diseases - microbiology Pyrones - chemistry Pyrones - isolation & purification Pyrones - pharmacology Radicinin Semisynthesis Structure-Activity Relationship Structure–activity relationships Vitaceae Vitis - microbiology Vitis vinifera Xylella - drug effects Xylella fastidiosa Antibiotic Semisynthesis Endophytic fungus Xylella fastidiosa Grapevine Radicinin Pierce’s Disease Vitaceae Vitis vinifera Cochliobolus sp Structure–activity relationships
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Summary:	Radicinin (1) produced by a strain of Cochliobolus sp. isolated from grapevine inhibits Xylella fastidiosa in vitro, suggesting a possible mechanism for tolerance of Pierce’s Disease. [Display omitted] •Endophytes may confer grapevine with non-genetic tolerance of Pierce’s Disease.•A Cochliobolus sp. isolated from grapevine inhibits Xylella fastidiosa in vitro.•Radicinin from Cochliobolus sp. shows dose-dependent inhibition of X. fastidiosa.•Three radicinin derivatives were prepared to assess structure–activity relationships.•Enzyme inhibition may occur via conjugate addition to carbon-10 of radicinin. The fastidious phytopathogenic bacterium, Xylella fastidiosa, poses a substantial threat to many economically important crops, causing devastating diseases including Pierce’s Disease of grapevine. Grapevines (Vitis vinifera L.) planted in an area under Pierce’s Disease pressure often display differences in disease severity and symptom expression, with apparently healthy vines growing alongside the dying ones, despite the fact that all the vines are genetic clones of one another. Under the hypothesis that endophytic microbes might be responsible for this non-genetic resistance to X. fastidiosa, endophytic fungi were isolated from vineyard cvs. ‘Chardonnay’ and ‘Cabernet Sauvignon’ grown under high Pierce’s Disease pressure. A Cochliobolus sp. isolated from a Cabernet Sauvignon grapevine inhibited the growth of X. fastidiosa in vitro. Bioassay-guided isolation of an organic extract of Cochliobolus sp. yielded the natural product radicinin as the major active compound. Radicinin also inhibited proteases isolated from the culture supernatant of X. fastidiosa. In order to assess structure–activity relationships, three semi-synthetic derivatives of radicinin were prepared and tested for activity against X. fastidiosa in vitro. Assay results of these derivatives are consistent with enzyme inactivation by conjugate addition to carbon-10 of radicinin, as proposed previously.
Bibliography:	ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	0031-9422 1873-3700
DOI:	10.1016/j.phytochem.2015.03.015