Gene-inspired mycosynthesis of skeletally new indole alkaloids
Li Ping Lin1, Peng Yuan1, Nan Jiang2
1†State Key Laboratory of Pharmaceutical Biotechnology, Institute of Functional Biomolecules, Nanjing University, Nanjing 210093, China.
Abstract:
Dalesindole, an antibacterial and anti-inflammatory indole alkaloid with an undescribed carbon skeleton, was stereoselectively constructed by Daldinia eschscholzii through class II aldolase catalyzed Michael addition of fungal chromone with 3,3'-diindolylmethane (DIM) formed in situ from indole-3-carbinol (I3C) under catalyses of monooxygenase and 8-amino-7-oxononanoate synthase (AONS). Dalesindole isomerizes via a retro-Michael reaction to give stereoisomers with bioactivities. The work provides an access to new bioactive hybrids of fungal oligoketide with microbially decorated exogenous chemistry.
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