Journal
ORGANIC CHEMISTRY FRONTIERS
Volume 6, Issue 5, Pages 571-578Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c8qo01124a
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Funding
- National Natural Science Foundation of China [31760096, 81660717]
- Yunnan Innovative Research Team for Discovery and Comprehensive Utilization of Functional Small Molecules in Medicinal Plants
- Science Foundation of Yunnan
- National Natural Science Foundation of Yunnan provinces [2017FB133]
- Union Special Fund of Yunnan Provincial Science and Technology Department
- Yunnan University of Traditional Chinese Medicine [2015FB205(-025)]
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A biosynthetic gene cluster for chevalone E (1) and its oxidized derivatives have been identified within the genome of the endophytic fungus Aspergillus versicolor 0312, by a mining strategy targeting a polyketide- diterpenoid hybrid molecule. The biosynthetic pathway has been successfully reconstituted in the heterologous fungus Aspergillus oryzae. Interestingly, two P450 monooxygenases, Cle2 and Cle4, were found to transform 1 into seven new analogues including 7 and 8 that possess a unique five- membered lactone ring. Furthermore, the replacement of the terpene cyclase gene with that from another fungus led to the production of sartorypyrone D (11), which has a monocyclic terpenoid moiety. Finally, some of the compounds obtained in this study synergistically enhanced the cytotoxicity of doxorubicin (DOX) in breast cancer cells.
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