title: Gene-inspired mycosynthesis of skeletally new indole alkaloids.
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.
authors.affiliation: †State Key Laboratory of Pharmaceutical Biotechnology, Institute of Functional Biomolecules, Nanjing University, Nanjing 210093, China.
authors.forename: Li Ping
authors.initials: LP
authors.lastname: Lin
authors.affiliation: †State Key Laboratory of Pharmaceutical Biotechnology, Institute of Functional Biomolecules, Nanjing University, Nanjing 210093, China.
authors.forename: Peng
authors.initials: P
authors.lastname: Yuan
authors.affiliation: §School of Pharmacy, Nanjing Medical University, Nanjing 210029, China.
authors.forename: Nan
authors.initials: N
authors.lastname: Jiang
authors.affiliation: ∥Department of Clinical Laboratory, the First Affiliated Hospital of Nanjing Medical University, Nanjing 210029, China.
authors.forename: Ya Ning
authors.initials: YN
authors.lastname: Mei
authors.affiliation: †State Key Laboratory of Pharmaceutical Biotechnology, Institute of Functional Biomolecules, Nanjing University, Nanjing 210093, China.
authors.forename: Wen Jing
authors.initials: WJ
authors.lastname: Zhang
authors.affiliation: †State Key Laboratory of Pharmaceutical Biotechnology, Institute of Functional Biomolecules, Nanjing University, Nanjing 210093, China.
authors.forename: Hui Min
authors.initials: HM
authors.lastname: Wu
authors.affiliation: †State Key Laboratory of Pharmaceutical Biotechnology, Institute of Functional Biomolecules, Nanjing University, Nanjing 210093, China.
authors.forename: Ai Hua
authors.initials: AH
authors.lastname: Zhang
authors.affiliation: †State Key Laboratory of Pharmaceutical Biotechnology, Institute of Functional Biomolecules, Nanjing University, Nanjing 210093, China.
authors.forename: Jiang Ming
authors.initials: JM
authors.lastname: Cao
authors.affiliation: §School of Pharmacy, Nanjing Medical University, Nanjing 210029, China.
authors.forename: Zheng Xin
authors.initials: ZX
authors.lastname: Xiong
authors.forename: Ye
authors.initials: Y
authors.lastname: Lu
authors.affiliation: †State Key Laboratory of Pharmaceutical Biotechnology, Institute of Functional Biomolecules, Nanjing University, Nanjing 210093, China.
authors.forename: Ren Xiang
authors.initials: RX
authors.lastname: Tan
mesh_terms: D002867:Chromones / Q000737:chemistry / Q000378:metabolism*; D026121:Indole Alkaloids / Q000737:chemistry / Q000378:metabolism*; D008958:Models, Molecular; D015394:Molecular Structure
chemical_list: D002867:Chromones; D026121:Indole Alkaloids; C000601932:dalesindole