Xyolide, a bioactive nonenolide from an Amazonian endophytic fungus, Xylaria feejeensis

Ezra G. Baraban; Jesse B. Morin; Gillian M. Phillips; Andrew J. Phillips; Scott A. Strobel; Jo Handelsman

doi:10.1016/j.tetlet.2013.05.093

Xyolide, a bioactive nonenolide from an Amazonian endophytic fungus, Xylaria feejeensis

Ezra G. Baraban, Jesse B. Morin, Gillian M. Phillips, Andrew J. Phillips, Scott A. Strobel, Jo Handelsman

Research output: Contribution to journal › Article › peer-review

28 Scopus citations

Abstract

Endophytes isolated from tropical plants represent a largely untapped reservoir of bioactive secondary metabolites. We screened a library of fungal endophyte extracts for inhibition of the plant pathogen, Pythium ultimum, and purified an active compound using bioassay-guided fractionation. A new nonenolide, (4S,7S,8S,9R)-4-O-succinyl-7,8-dihydroxy-9-heptyl-nonen-9-olide, was isolated and named xyolide. The structure was elucidated by a combination of 1D and 2D NMR methods and the absolute configuration was determined by exciton-coupled circular dichroism. The MIC of xyolide against P. ultimum was 425 μM.

Original language	English (US)
Pages (from-to)	4058-4060
Number of pages	3
Journal	Tetrahedron Letters
Volume	54
Issue number	31
DOIs	https://doi.org/10.1016/j.tetlet.2013.05.093
State	Published - Jul 31 2013
Externally published	Yes

Keywords

Fungal endophyte
Natural product
Nonenolide
Pythium ultimum

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2013.05.093

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title = "Xyolide, a bioactive nonenolide from an Amazonian endophytic fungus, Xylaria feejeensis",

abstract = "Endophytes isolated from tropical plants represent a largely untapped reservoir of bioactive secondary metabolites. We screened a library of fungal endophyte extracts for inhibition of the plant pathogen, Pythium ultimum, and purified an active compound using bioassay-guided fractionation. A new nonenolide, (4S,7S,8S,9R)-4-O-succinyl-7,8-dihydroxy-9-heptyl-nonen-9-olide, was isolated and named xyolide. The structure was elucidated by a combination of 1D and 2D NMR methods and the absolute configuration was determined by exciton-coupled circular dichroism. The MIC of xyolide against P. ultimum was 425 μM.",

keywords = "Fungal endophyte, Natural product, Nonenolide, Pythium ultimum",

author = "Baraban, {Ezra G.} and Morin, {Jesse B.} and Phillips, {Gillian M.} and Phillips, {Andrew J.} and Strobel, {Scott A.} and Jo Handelsman",

note = "Funding Information: The authors acknowledge Daniel C. Cooper, Percy Nu{\~n}ez Vargas, and Candice A. Baird for their assistance with molecular modeling, plant identification, and mass spectrometry, respectively. This work was supported by the Howard Hughes Medical Institute Professors Program . ",

year = "2013",

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doi = "10.1016/j.tetlet.2013.05.093",

language = "English (US)",

volume = "54",

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T1 - Xyolide, a bioactive nonenolide from an Amazonian endophytic fungus, Xylaria feejeensis

AU - Baraban, Ezra G.

AU - Morin, Jesse B.

AU - Phillips, Gillian M.

AU - Phillips, Andrew J.

AU - Strobel, Scott A.

AU - Handelsman, Jo

N1 - Funding Information: The authors acknowledge Daniel C. Cooper, Percy Nuñez Vargas, and Candice A. Baird for their assistance with molecular modeling, plant identification, and mass spectrometry, respectively. This work was supported by the Howard Hughes Medical Institute Professors Program .

PY - 2013/7/31

Y1 - 2013/7/31

N2 - Endophytes isolated from tropical plants represent a largely untapped reservoir of bioactive secondary metabolites. We screened a library of fungal endophyte extracts for inhibition of the plant pathogen, Pythium ultimum, and purified an active compound using bioassay-guided fractionation. A new nonenolide, (4S,7S,8S,9R)-4-O-succinyl-7,8-dihydroxy-9-heptyl-nonen-9-olide, was isolated and named xyolide. The structure was elucidated by a combination of 1D and 2D NMR methods and the absolute configuration was determined by exciton-coupled circular dichroism. The MIC of xyolide against P. ultimum was 425 μM.

AB - Endophytes isolated from tropical plants represent a largely untapped reservoir of bioactive secondary metabolites. We screened a library of fungal endophyte extracts for inhibition of the plant pathogen, Pythium ultimum, and purified an active compound using bioassay-guided fractionation. A new nonenolide, (4S,7S,8S,9R)-4-O-succinyl-7,8-dihydroxy-9-heptyl-nonen-9-olide, was isolated and named xyolide. The structure was elucidated by a combination of 1D and 2D NMR methods and the absolute configuration was determined by exciton-coupled circular dichroism. The MIC of xyolide against P. ultimum was 425 μM.

KW - Fungal endophyte

KW - Natural product

KW - Nonenolide

KW - Pythium ultimum

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

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ER -

Xyolide, a bioactive nonenolide from an Amazonian endophytic fungus, Xylaria feejeensis

Abstract

Keywords

ASJC Scopus subject areas

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