Chemical ecogenomics-guided discovery of phytotoxic α-pyrones from the fungal wheat pathogen Parastagonospora nodorum

Hang Li; Jinyu Hu; Haochen Wei; Peter S. Solomon; Daniel Vuong; Ernest Lacey; Keith A. Stubbs; Andrew M. Piggott; Yit Heng Chooi

doi:10.1021/acs.orglett.8b02617

Chemical ecogenomics-guided discovery of phytotoxic α-pyrones from the fungal wheat pathogen Parastagonospora nodorum

Hang Li, Jinyu Hu, Haochen Wei, Peter S. Solomon, Daniel Vuong, Ernest Lacey, Keith A. Stubbs, Andrew M. Piggott, Yit Heng Chooi^*

^*Corresponding author for this work

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

35 Citations (Scopus)

96 Downloads (Pure)

Abstract

A biosynthetic gene cluster that is significantly upregulated in the fungal wheat pathogen Parastagonospora nodorum during plant infection was reconstructed heterologously in Aspergillus nidulans. This led to the discovery of five new α-pyrone polyketides, alternapyrones B-F (2-6). Compounds 5 and 6, which contain a highly substituted dihydrofuran, exhibited phytotoxicity on wheat seed germination. It is demonstrated that only three enzymes, one highly reducing polyketide synthase and two multifunctional P450 oxygenases, are needed to synthesize the structurally complex products.

Original language	English
Pages (from-to)	6148–6152
Number of pages	5
Journal	Organic Letters
Volume	20
Issue number	19
DOIs	https://doi.org/10.1021/acs.orglett.8b02617
Publication status	Published - 5 Oct 2018

Bibliographical note

Copyright the Publisher 2018. Version archived for private and non-commercial use with the permission of the author/s and according to publisher conditions. For further rights please contact the publisher.

Access to Document

10.1021/acs.orglett.8b02617

Accepted author manuscriptAccepted author manuscript, 6.95 MB

Cite this

@article{24ac8817d19146f182cb98dab491fbe0,

title = "Chemical ecogenomics-guided discovery of phytotoxic α-pyrones from the fungal wheat pathogen Parastagonospora nodorum",

abstract = "A biosynthetic gene cluster that is significantly upregulated in the fungal wheat pathogen Parastagonospora nodorum during plant infection was reconstructed heterologously in Aspergillus nidulans. This led to the discovery of five new α-pyrone polyketides, alternapyrones B-F (2-6). Compounds 5 and 6, which contain a highly substituted dihydrofuran, exhibited phytotoxicity on wheat seed germination. It is demonstrated that only three enzymes, one highly reducing polyketide synthase and two multifunctional P450 oxygenases, are needed to synthesize the structurally complex products.",

author = "Hang Li and Jinyu Hu and Haochen Wei and Solomon, {Peter S.} and Daniel Vuong and Ernest Lacey and Stubbs, {Keith A.} and Piggott, {Andrew M.} and Chooi, {Yit Heng}",

note = "Copyright the Publisher 2018. Version archived for private and non-commercial use with the permission of the author/s and according to publisher conditions. For further rights please contact the publisher. ",

year = "2018",

month = oct,

day = "5",

doi = "10.1021/acs.orglett.8b02617",

language = "English",

volume = "20",

pages = "6148–6152",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "19",

}

TY - JOUR

T1 - Chemical ecogenomics-guided discovery of phytotoxic α-pyrones from the fungal wheat pathogen Parastagonospora nodorum

AU - Li, Hang

AU - Hu, Jinyu

AU - Wei, Haochen

AU - Solomon, Peter S.

AU - Vuong, Daniel

AU - Lacey, Ernest

AU - Stubbs, Keith A.

AU - Piggott, Andrew M.

AU - Chooi, Yit Heng

N1 - Copyright the Publisher 2018. Version archived for private and non-commercial use with the permission of the author/s and according to publisher conditions. For further rights please contact the publisher.

PY - 2018/10/5

Y1 - 2018/10/5

N2 - A biosynthetic gene cluster that is significantly upregulated in the fungal wheat pathogen Parastagonospora nodorum during plant infection was reconstructed heterologously in Aspergillus nidulans. This led to the discovery of five new α-pyrone polyketides, alternapyrones B-F (2-6). Compounds 5 and 6, which contain a highly substituted dihydrofuran, exhibited phytotoxicity on wheat seed germination. It is demonstrated that only three enzymes, one highly reducing polyketide synthase and two multifunctional P450 oxygenases, are needed to synthesize the structurally complex products.

AB - A biosynthetic gene cluster that is significantly upregulated in the fungal wheat pathogen Parastagonospora nodorum during plant infection was reconstructed heterologously in Aspergillus nidulans. This led to the discovery of five new α-pyrone polyketides, alternapyrones B-F (2-6). Compounds 5 and 6, which contain a highly substituted dihydrofuran, exhibited phytotoxicity on wheat seed germination. It is demonstrated that only three enzymes, one highly reducing polyketide synthase and two multifunctional P450 oxygenases, are needed to synthesize the structurally complex products.

UR - http://www.scopus.com/inward/record.url?scp=85053687329&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.8b02617

DO - 10.1021/acs.orglett.8b02617

M3 - Article

C2 - 30226784

AN - SCOPUS:85053687329

SN - 1523-7060

VL - 20

SP - 6148

EP - 6152

JO - Organic Letters

JF - Organic Letters

IS - 19

ER -

Chemical ecogenomics-guided discovery of phytotoxic α-pyrones from the fungal wheat pathogen Parastagonospora nodorum

Abstract

Bibliographical note

Access to Document

Other files and links

Fingerprint

Cite this