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Updated: Oct 20, 2026

A Customizable Approach for the Enzymatic Production and Purification of Diterpenoid Natural Products
Published on: October 4, 2019
Tryptamine-triggered chemodiversity expansion of polyketides produced by Daldinia eschscholzii
Xiao Jing Lv1, Xue Yang1, Jing Wang1
1Synthetic Biology Center for Chinese Medicine, Nanjing University of Chinese Medicine, Nanjing 210023, China.
Abstract:
To expand the chemical space of small-molecule metabolites, we cultured the prolific fungal polyketide producer Daldinia eschscholzii in the presence of tryptamine-a substrate bearing an indole moiety widely found in marketed drugs and bioactive compounds. Six unprecedented indole-polyketides, named (±)-dalestrymanes A-F (1-6), were isolated and structurally characterized using chromatographic and spectroscopic methods. Each indole-polyketide underwent chiral resolution to yield pairs of enantiomers (1a/1b-6a/6b). The absolute configurations of separated enantiomers were determined by electronic circular dichroism (ECD) calculations. (±)-Dalestrymanes DF (4-6) are the first heterotrimers of tryptophol with two molecules of a fungal polyketide-1-(2,6-dihydroxyphenyl)butan-1-one, which can dimerize into nodulisporin F. Compounds 4b and 6a showed cytotoxicity against A549 cells (IC₅₀: 2.2 μM and 2.9 μM, respectively), while 5a was active against A375 cells (IC₅₀: 1.6 μM).
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