Tryptamine-triggered chemodiversity expansion of polyketides produced by Daldinia eschscholzii.

Authors

Xiao Jing Lv, Xue Yang, Jing Wang, Fei Ding, Ren Xiang Tan

Published in

Fitoterapia. Pages 107520. Oct 18, 2026. Epub Oct 18, 2026.

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).

PMID:
42893755
Bibliographic data and abstract were imported from PubMed on 19 Oct 2026.

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