1. Gene-inspired mycosynthesis of skeletally new indole alkaloids.
- Author
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Lin LP, Yuan P, Jiang N, Mei YN, Zhang WJ, Wu HM, Zhang AH, Cao JM, Xiong ZX, Lu Y, and Tan RX
- Subjects
- Chromones chemistry, Indole Alkaloids chemistry, Models, Molecular, Molecular Structure, Chromones metabolism, Indole Alkaloids metabolism
- 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.
- Published
- 2015
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