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 | |
| Publication status | Published - 5 Oct 2018 |
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Chemical Ecogenomics-Guided Discovery of Phytotoxic α-Pyrones from the Fungal Wheat Pathogen Parastagonospora nodorum. / Li, Hang; Hu, Jinyu; Wei, Haochen; Solomon, Peter S.; Vuong, Daniel; Lacey, Ernest; Stubbs, Keith A.; Piggott, Andrew M.; Chooi, Yit Heng.
In: Organic Letters, Vol. 20, No. 19, 05.10.2018, p. 6148-6152.Research output: Contribution to journal › Article
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
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
VL - 20
SP - 6148
EP - 6152
JO - Organic Letters
JF - Organic Letters
SN - 1523-7052
IS - 19
ER -